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Ask HN: How do you start a startup in your 30s when you have wife/kids/mortgage?
237 points by atzero 15 days ago | hide | past | favorite | 327 comments
I want to start my own company, but Im not sure how to pay my bills while looking for product-market-fit.

I have a well paying job now, and I am pretty sure I would throw my marriage into chaos if I told my wife I was leaving my job to pursue a start up. Shes not stupid, she knows start ups have like a 90% failure rate.

So the question is: how do I continue my current standard of living for my family while working on a startup?

Are all startups at my age generally side hustles that become profitable enough to quit my day job?

Does anyone here have experience with this?




My very concrete feelings on this is that you probably don't.

Asking folks how to do this is a bit like asking billionaires how to get rich. It's a fun story but it's overfitting. The individual narrative that made a billionaire is unlikely to be available for you. If you ask some millionaires they may be more likely to give you some useful advice around sound investment strategies, living within your means, and identifying great opportunities.

You signed up for a bunch of responsibilities. You are always going to be your kids parent. You are only going to have this one opportunity to get this marriage and this family right. If you have a solid job that allows you to be there for them, take it and be amazing in this potentially incredibly rewarding role.

Then do an awesome startup when your kids are out of the house, you have a solid nest egg, and you can take risks again in your 50s.


Agreed 100%. When people ask me what the best time is to work on a startup, it's always when you have no dependents, living with parents, and perhaps no significant other. It's quite amazing just how much you can skim down your expenses at that point in life.

Minimizing expenses, maximizing runway. The rest is luck. Just blind luck.


> Minimizing expenses, maximizing runway.

If you're in the US, and not living with your parents (and or don't want to do that), one of the best ways to do it is to live in a university town. They're wired for fast Internet, the cost of living (including rent) is often very reasonable, they're among the safest areas in the US on average, and you can work at mundane jobs to pay your bills (30-36 hours per week; telemetry tech at a hospital; cashier or lead in retail making $15-$20/hr; etc). In the typical university town you can rent for $650-$1000 for a 1 or 2 bed + 1 bath apartment in a safe area. Working for a hospital you'll also usually get solid health insurance. The jobs are not difficult, they're relatively easy to get, although they will grind on you when combined with doing a startup (it's part of the trade you're making). Also in these types of jobs you won't have much if anything to worry about regarding intellectual property issues, conflicts of interest, et al.

Source: have done this, it works quite well. It can be exhausting working 80-100 hours per week obviously. The income/job becomes a permanent stream of venture capital, you can just endlessly fund your own way and keep 100% of the pie. I've often chosen to not do tech contracting work while working on a startup and self-funding with outside income, because I don't like the potential IP risks/conflicts and the burnout factor of always working on software/services/sites/whatever.


Have you lived in a university town recently? I do, and your rent estimate is low by a factor of about 2.


Yeah, I'm living in one now. My rent is $700 for around 750 sq ft of space in a rather typical apartment complex; one bed, one bath, very safe area (it's a safe city in general), access to 1.2 gbps Comcast (I'm paying $30x for 300mbps). That rent will climb to $750 when my lease renews in 2023, but it's still quite reasonable.

Picked a random university city: Tallahassee, FL (Florida State University). Tons of apartments available across the city for $750-$1000. It'll also work for Gainesville, FL (University of Florida; although it's more expensive than Tallahassee).

You can do it in Blacksburg, VA (Virginia Tech). Although it'll push you closer to $900-$1100 on rent. Charlottesville, VA (University Virginia) is at the edge of affordable for this scenario, although that is also doable.

Lubbock, TX is pretty easy (Texas Tech). It'll work for College Station, TX (Texas A&M). Waco, TX (Baylor) is a bit of a mixed bag on crime, however it also works.

It'll work in Champaign, IL (University of Illinois Urbana-Champaign).

It'll work in Iowa City, IA (Iowa University). Also in Ames, IA (Iowa St).

It'll even work in Pittsburgh, PA. Which is both a mid-size city and a university city (Pitt, Carnegie).

The same goes for Madison, WI (mid-size city, with University Wisconsin). Although it'll push you closer to $900-$1,100.

It'll work in Athens, GA (University of Georgia).

It'll work in Manhattan, KS (Kansas State).

It'll work in Norman, OK (University Oklahoma).

It'll work in West Lafayette / Lafayette, IN (Purdue).

It'll work in Fayetteville, AR (University Arkansas).

It'll work in Las Cruces, NM (New Mexico St University).

It'll work in Morgantown, WV (West Virginia University).

It'll work in Columbia, SC (University South Carolina). Although the crime is more elevated. The same goes for Tuscaloosa, AL (University Alabama).

It even gets you pretty close for Ann Arbor, MI (University of Michigan). Rent will be closer to $1,100 to $1,200.

There are a lot more options, and that's just among the more prominent university list.

The only ones that typically won't work at all are high cost of living states like MA or CA, particularly affluent universities (getting anywhere near them in location), or smaller towns with few apartments (availability).


It’s also invigorating being around young people all the time, just don’t get sucked into too much partying :D


I would say it's not JUST luck. You're not going to sell a startup if you haven't created one. So there's requisite work that is then followed by luck.


Right. "The rest is luck."

I would say "chance", since there's no such thing as luck.


Lots of indie hackers defeat blind luck and exit as much as the small percentage founders receive in a funded startup.

Lots of good reading out there


Right it's a lottery, with very expensive tickets. You may have to pay with years of your life for each one, possibly significant others.


Not if you consult and find the business needs and only build wher people want and are willing to pay for.

Hitting the startup funding lottery to go on an expedition to find and build something people want is a different matter and maybe what you’re referring to, and if so, I totally agree with.


> Not if you consult and find the business needs and only build wher people want and are willing to pay for.

That's only one part of the challenge. Market research is vital, yet alone is a not guaranteed success. Even if a valuable untapped market is discovered, there's more to success than just building a solution. Sales and marketing have to execute well too. A competitor from an adjacent industry could swoop in. Etc.


This is “obvious” advice but also statistically a huge number of startups are founded by older people with families, houses, etc.


I've actually worked at a handful of startups founded by middle aged men with families. I would kill to have coffee with one of their wives or older kids though because there's no fucking way those guys contribute meaningfully to the family life. I know how much they work because I was right there.

Also in every case they were already wealthy, either from early career success or just the traditional path of inheriting it. That takes a lot of the risk out and lets you outsource the domestic labor, reducing some of the burden you're asking your family to carry.

Anyway I've seen that up close and it's not necessarily inspiring.


"The harder I work, the luckier I get."


Alternatively, maybe your dad owns an emerald mine? Always an option!


Elon founded two companies Zip2 and X.com which merged with PayPal, was mega rich and didn’t need to work ever again on his own efforts, before even doing SpaceX and his other ventures


Even if entirely accurate, he also had a safety net in his father. Few get into Stanford, even fewer can afford to drop out to bet on some new market.


How is this "safety net" relevant? Literally millions of people in America have same or better "safety net". Are they some kind of lazy losers because they haven't earned billions like Elon had?


Consciously or not, having rich parents makes taking big risks in life easier. Even estranged and rich parents could be a lifeline if a crazy plan goes sideways.

Very few in the USA have parents who own emerald mines or an equivalent amount of wealth. So they're not losers. They're just not as fortunate and--understandably--more risk averse.

I'm saying that Elon deserves a modest amount of credit for busting his ass in the early days. But not so much fawning praise since luck and birth also played a outsized role in his successes.


This isn't true (since 89)

https://www.snopes.com/news/2022/11/17/elon-musk-emerald-min...

Keeps coming up, even though it's a pretty easy google.


> You signed up for a bunch of responsibilities. You are always going to be your kids parent. You are only going to have this one opportunity to get this marriage and this family right.

I think this is a bit of a depressing take. Even committed parents and spouses take alone time for themselves and have hobbies. Just treat your side project as your hobby and you can still have a healthy family.

Also, think about how much time the average person wastes day-to-day. Total up all the time watching television, reading articles, browsing online. Outsource your chores and improve the efficiency of your day job (e.g., work remotely to eliminate a commute) and you'll have plenty of time left over for a side project.

You might say — how can a side project be successful on 5 hours a day in the early morning? — but consider that someone pursuing a startup for 10 hours a day isn't going to have a significantly higher probability of success relative to other factors that make a larger difference (ability to interact well with other people, product-market fit, etc.) Sure, you might reduce your probability of success a bit, but you are essentially buying a lottery ticket anyway when you decide to start your own company, so would it really bother you much if your already small odds of success are 60% of what they would have been if you committed to the startup full-time?


> Even committed parents and spouses take alone time for themselves and have hobbies.

The parents I know with kids younger than 7 have no time for themselves or their hobbies. They're lucky if they can scrape together a few hours a week for basic self-care. In the mornings the kids demand full attention and after the kids go to bed there's maybe time for a single TV show which one person falls asleep during.

> how can a side project be successful on 5 hours a day in the early morning?

So from 4am-9am a person is grinding away on their side project or startup while their spouse takes care of getting their kids ready. And then at 9am they just slide right into work for a cool 8 hours, eating lunch at their desk and then checking out at 5pm for a nice family dinner.

This sounds like a robot's advice to a human to how to organize their life. Completely not feasibly and devoid of lived experience.


Are you speaking from personal experience? I am a parent and have a younger daughter and I have many other parent friends, we all had kids within a similar age range. I have plenty of time to spend with my family and I am also the founder of a successful company.

If anything, being a parent taught me how to be very efficient with my time and how to cut things out that were meaningless. The arrangement I have with my spouse is that on weekdays I take care of the morning, and she takes care of the night. That means I'm responsible for getting breakfast ready, getting my daughter ready and sent to school, and my wife is responsible for dinner and putting my daughter to bed. On weekends our arrangement is usually that Saturday morning I get to sleep in and my wife mostly handles the day, and on Sunday it's the opposite.

I can't speak for everyone, but as I said before when I became a dad I realized there are just soooo many little things that consume 10 minutes here, 10 minutes there, some procrastination here and there and I could cut them all out and add on the order of an additional 120 minutes per day, which is not at all trivial. It used to take me 40 minutes to an hour in the morning to shower, use the bathroom, brush my teeth, get dressed... now all of that is done in about 20 minutes. I used to do various daily errands during busier times of the day and get stuck in lines, now I do them during less busy times of the day.

Finally, changing my life in this way not only has given me more time, it also makes me a much more organized person and a more effective business leader.


As a counter-balance: I have 3 children, twins who are 3 (and I am the twin parent) and a 1 year old. My wife is still in recovery and on partial (she works 20 hours / week right now) disability from the birth of our youngest.

I've reduced my hobbies down to: 1) reading before I fall asleep at night, 2) exercising during my lunch hour on work days. That's it. I managed to change jobs earlier this year but it was challenging and it remains a challenge to remain ahead with my current role due to my family obligations.

My situation is somewhat unique but is certainly not an outlier.


I’m a twin parent as well. Similar situation for a bit.

Becoming a parent during the pandemic or shortly before is no joke on its own. Wish there was a way to connect with them at scale lol. Maybe we can start up a discourse forum together.

Hang in there.

It was nice to see another parent here identify as a twin parent.


The chain you are responding to is talking about working full time, and working a startup on the side, and still having a family life. Forgive me if I’m wrong, but it sounds like you are able to focus on working your company.

My experience is that with two parents, both working full time at demanding jobs, challenging kids under 7, there is hardly time for even the necessities. That said, we do know one-earner families with easy kids, and they do seem to have time for it all.

There’s a theoretically spare hour or two in the evening after bedtime, but at that point both parents have been going flat-out for about fourteen hours, so exercise and passion projects are only going to happen through sheer grit- which both parents have pretty much used up over the last half decade.


Congrats to you that you've made this work. I've made attempts at the "super efficient optimise every moment" thing and it always eventually collapses for me with severe mental exhaustion. I cannot be "on" that much. It just isn't in me.


Yep absolutely, it's not for everyone. One question I'd ask of you is do you exercise regularly? The one thing I'd say that gave me the kind of energy to be "on" all the time is having a daily exercise/cardio routine and changing my eating habits. Not saying this works for everyone, but the effect that doing that had on my life was enormous.


I lift weights. Not too big on cardio, after many attempts at doing it (running, cycling, swimming). Lifting weights is the one thing that I finally found I can stick with. My diet is decent, mostly cook for myself and avoid highly processed foods and a lot of sugar. I am not strictly following any dietary program though.

I like the effect the weightlifting has on my body. It's nice that I have some definition and strength. But honestly cannot say it's had a big effect on my energy, motivation, outlook, etc.

I have tried enough things that other people say have made a tremendous difference in their life, from exercise to supplements to diet to reading philosophical books and they just... don't. I still feel like the same person. I don't think there are any secret tricks. People are who they are, fundamentally. Accepting that feels like giving up sometimes, but also brings some peace and freedom.


Kranar, with all due respect, you are lucky to have a partner who shares the responsibilities equally. All it takes is for one 1/2 not to contribute equally - or to be a single parent - and your plan would simply not work.


I am very lucky and never said otherwise. I am lucky to have an amazing daughter, to live in an amazing country, an amazing wife, to have had all of the opportunities afforded to me.

Not that you explicitly state it, but don't assume that because someone is successful or is giving advice to people about potential paths they can pursue, that they are ungrateful or don't appreciate their life circumstances. One of the other things I'm grateful for are the mentors and role models who have shared their knowledge with me and I'm happy they did so without being drowned out by people dismissing their success as simply due to luck.


Thanks for the flippant comment. You completely missed my point, but that’s ok, this is the internet.


Didn't miss your point at all, just informing you that on the whole it's superficial and implied from my post. There is a myriad of things that many of us posting on Hacker News are lucky for, and it's not necessary to point them all out since it can be assumed from context.

To the extent that your reply telling me that I'm lucky to have the wife I have could possibly serve a purpose, it's to be dismissive and to make huge assumptions about me personally that you're frankly not in a position to make. It presumes that my marriage is the result of luck and happenstance and ignores the incredibly hard work and amount of effort that successful marriages require in order to make sure both partners are respected and satisfied.

To be honest, it's not at all uncommon for people who fail to find meaningful relationships, whether it's strong friendships or love to think that they just happen on their own through chance, instead of being something that actually requires putting in effort, compromise, communication, sacrifice, and yes it's true... it also involves luck as well.

Given the context and the general audience of people on this website in a position to meaningfully talk about starting a business, it is likely that said audience is very lucky for many many things; we don't need to point those out, what we need to do is determine how to best put that luck and the opportunities afforded to us towards a meaningful and productive life instead of squandering that luck away.

And finally, when someone prefaces a post with "with all due respect", that's usually a passive aggressive way of telling them off, so if you want people to afford you some degree of respect in the future then think about cutting that out.


Me too on falling at it.

The answers to do that is not in our current selves. Had to read a lot to learn ways.


Can second this. My arrangement with my spouse is the opposite. She takes care of the mornings and me the evenings, and then I take weekends. It gives me a lot of free time.


I’m a parent and I know a lot of parents. The amount of time available for self-care and hobbies varies dramatically, based on type of job, whether you work remotely, whether both parents work, whether you have childcare, number and temperament of children, etc. Some can pull off a side business, some can’t.

And even if you can, you very likely won’t get five hours of productive time in every morning. But you can get one or two on most days, and that might be enough to build something that’s making enough to take a leap and go full-time. If you’re lucky. It’s hard, but not impossible.


Agreed. My impression is that most parents are already overworked at their day jobs, and then proceed to not even workout. Lots of people don't even have hobbies.


I’ve heard a recommendation to can get a job that pays a little less for way less effort and save the energy for what I really want.

A lot of people want to eat their cake and have it too though though.

Hopefully building a money printing startup is enough of a hobby :)


The cake is always eaten, but what the cake is might not be apparent until it's too late


Haha touché.


I have young kids very close in age. Doing a startup. Life doesn’t get easier, you just have to get better kids or not. Besides todays the youngest you’ll ever be, if both now, then when?

tldr; You can get funding and have balanced pursuit and resources. For the 98% of founders who can’t, won’t or don’t get funding, self-funding and bootstrapping is a way to build the thing to free your time to then swing for the fences - same transferable startup skills required.

With kids, I realized I traded a lot of time wasting for two amazing beings and it’s optimizing my time with and ultimately for them. People make expensive decisions that lock them in to cost time in addition to kids. Minimizing those has been a blessing. You can get back many hours. I’m going to share here so other parents can share with me here and I can learn from them.

On to trying to paint an alternative picture:

One thing missing in this post is it’s more about the effectiveness with your time than the quantity of it as you get older. When starting out, few are effective with their time but we have lots to waste. If we can admit it’s needed we can become more effective quicker.

Today, every minute matters. I’m not perfect, but nothing gets easier, you just get better. Everything’s a grind.

Kids can help prioritize in a big way for some. If you think you have an idea based in hearing from parents it’s not super accurate because everyone’s life situation is different.

- 4-9 am isn’t a guarantee. Kids will be sick. Late nights can be tiring. I find I can just go to bed at 8 or 9 most nights and wake up at 2 or 3. Works great if I have a few devs overseas helping because am in my 30s and probably have a few thousand to get help with. When I slip in my schedule I start over.

- Being hyper organized with every little step that needs to be done next helps make the most of small pockets of time. This was hard for me and I’m still learning to get better every day. If I don’t casually get 4-8 hours straight on the weekends to work on something I still am able to find ways to be more effective.

- Startups are a business not coding alone: Time away from the keyboard can actually be valuable to stop and get perspective. Often I don’t need hours anymore to do something where it can be done in 60 minutes while thinking about it away from the keyboard. Thinking can actually be a lot of the work to be done in some steps. I never would have designed and simplified a great deal in my startup if it wasn’t for those late nights.

- Face yourself. Generally ppl who weren’t the best with their time before kids might have a hard time after. Everyone Has run to improve but not everyone realizes discipline leads to improvement and freedom.

- Learn to change better than you are: A lot of people aren’t as good with change as they imagined themselves to be too. It’s why advice sucks sometimes. If you’re good with changes and improvements you’ll love meeting the next version of you on the other side of kids.

Things I’ve done against the grain as a entrepreneur and new parent..

- Big problems and opportunities often attract to small problems that get solved: the initial idea should be strategic, disciplined and calculated enough to be successful. This means small enough and able to win $ and be part of the big picture to grow into. Buy my time back with a small team that I pay for or get tinyseed type funding for. Maximize return, lower risk, build momentum, failure is not an option.

To pursue this in my personal life:

- Don’t buy things that I’m buying a ton of maintenance time with. Cars, houses, pets (pets usually becomes dads pets) should all be thought about a little more. Buying boring things or none at all saves your time. Let your friends have fun taking their Audis to the shop all the time. But boring so you can spend your time on interesting things.

- Eliminate commuting as much as possible. Actually most driving. But have a car. 2 hours a day driving is 10 a week, ~40 a month. Imagine getting 1 extra week per month back. Get a vehicle with room to get more stuff done near by. Batch. Save time wasting for a planned times of fun.

- Social Invitations- it can be hard to imagine but people do end up in their lives just over times. if they won’t come to you sometimes you don’t always have to go to them.

- Setup an above average remote work setup and build the space it into your home life. Get multiple ergonomic proper work setups, put gaming stuff in its own dedicated space. Two 2k monitors minimum if not 3. Slightly better screen resolution gives more working pixels which helps work much faster. Buy different keyboards including economic and cycle them through. Every little thing saves your energy a bit longer for work or family. Every desk should be a standing desk they are super inexpensive now. Our home has multiple spaces with multiple monitors that can plug in a mac or surface pro. If it’s the open room there’s a noise cancelling headset so people hear kids less if they were ever home sick. ready to go. Keeps everyone calm and cool. One workspace is the room between mine and kids. If someone’s up at night they can be super close by. It’s a sound proofed room so calls can even happen. All to say it takes seconds to plug in and get going instead of minutes. Adds up too. Buy extra power adapters.

- Improve mobility: Carry a big screen phone + iPad mini in a sling, or ideally a MacBook 12” in your baby bag. So much down time in vehicles or appointments can be easily recaptured. Again if you want it all your might have to be creative to get at it. My 12” MacBook is the best for unexpected waits or delays time. Wish I had it as a 2nd laptop when it just came out. Priceless.

- Location should create free time; we left the burbs and came back closer to downtown. Pick up times our kids now has an extra hour or two of flexibility for work (!), And most days we’re done and drive home in 8 minutes. Dinner is cooked served and done before rush hour is over. Most of my friends are usually still driving home. Doing this sooner in the day helps wind down for kids with quality time and energy easier, and there’s still energy to start back up on work. The alternative is I could go do the things I’m supposed to and get a house far in a suburb and kids are under pressure to sleep. Not always a good feeling not a possibility for everyone.

- food. Your energy is what you eat. Meal prep until you have enough meals in fridge and meals prepped in the freezer before cooking any nightly meals. Buy 2 instant pots to do rice and food at the same time or 2 meals at the same time. Did prep Sundays and Wednesdays if needed. Eat out less and feel sluggish less.

- ask for and take help and pay for it if you need: if you can live closer to your family, work and startup it can be life changing. One of my friends lives next to their parents. Siunds crazy but no vehicles to load or unload. Kids can be kicked out to grandparents for last minute night out. Kids are also standing outside to help grandma/pa to load and unload groceries. It doesn’t matter if something isn’t packed or forgotten. I understand this isn’t possible for many of us but I am happy for those who it works for.

- have everything you can delivered on subscription, spend the saved shopping time to adjust frequency of times.

Message for above poster / in general: Please, don’t tell or imply people they aren’t capable of something. Innovation can only happen in a mindset of possibility and the world isn’t a toilet for doubt worshippers wanting to externally validate their doubts by painting them on others.

Everything has opportunity cost. I try to remember what kind of example and memory I want to be for my kids and let it balance and inform my presence with them. My spouse reminds me the only ppl who will care long term that I’m dead is my kids and hopefully her lol. It gives some a focus to live and achieve for that can magnify and accelerates a lot.

I’m not telling you to have kids or not.

Be open to seeing the good and you will. If you want to see the bad and worries you’ll see it too. You might just discover most things are like lifting weights at the gym, you get stronger the more you do it and not from the sidelines.


This is great specific advice that you don’t see often. Thanks for taking your valuable time to share that!


I actually agree with a lot here. If the question had been "how can I have a fulfilling hobby while also working full time", i think I'd agree with a lot of the advice you gave. It's very good advice about time boxing, having realistic goals, and looking for a well rounded life. Having hobbies is something that can be really rewarding, and hobbies can be many kinds of things, from deeply technical to purely relational and social.

However, I will admit my bias here, the OP explicitly talked about "a startup", and I don't believe I know of too many hobbies that allowed someone to replace their income and retain their standard of living. The people I know who have done this have, regularly, done so with significant risk, commitment, and single-mindedness of purpose. I'm sure there are exceptions as those you listed, but I personally haven't experienced them.


To me, it's not the time - but the energy. I have about 4 solid "mentally productive" hours in a day that use up the majority of my mental brain energy. Trying to cultivate that energy to do a side hustle after kids are asleep is the real challenge.

Source: 2 kids, 4 and 6.


For sure, you're only going to have a few hours of 10x productivity, but you can still get something done outside of that optimal time interval.

I've been kinda weaseling lately and just working on my startup during my best hours before work. Mr. Fangman will be satisfied even if I just "meet expectations", and I'd rather put my best efforts into something that can pay off bigger than a 5-6 figure yearly bonus


I agree with the premise of this, but want to point out a normal job doesn’t necessarily lead to fulfilling those responsibilities adequately even though maybe they should. People still get stressed, overwork, have ambition, dislike home life, etc.

I think OP should talk with his wife and make a decision based on milestones


I agree with you on both points:

1. If it's a bad job that pays well but makes you miserable, that's a different situation. I assumed that was not the case but I may have been hasty.

2. No matter what, discussing with your partner is absolutely the right thing. But really discussing and coming together to try to come to a shared understanding. You never know, their tolerance for risk may be even higher than yours!


I agree partly.

Millionaire bootstrapper here.

The part I agree with is to just ask people who have done what you want to do and get an idea of the sacrifice and time commitments involved.

The part I DISAGREE with is to wait to do a startup until you’re in your 50’s. This is really horrible advice that can lead to resentment for you and negative outcomes for your family. You CAN start a business and have a family but you’ll need to be STRATEGIC.

A couple of personal tips for bootstrapping…

1. Communicate and commit to joint goal setting with your family. What are you all working towards together and why? None of us build companies alone.

2. Make your day job your first customer and biggest supporter. If you can’t then join an organization that is not threatened by entrepreneurship.

3. Identify a family friendly business model that you can test with minimal effort. I’ve always started my own businesses with my own money (Seed ~100k USD). My largest business does high seven figures and I started it with ~25k USD. This means getting in bed with a customer(s) early and charging upfront. Again see (2).

4. Set reasonable timelines for yourself. While your LinkedIn feed has friends pumping out VC propaganda remind yourself that you’re focused on actually building a sustainable business so take your time where you can. This might mean working with your wife to create a schedule for yourself where you work on the business TOGETHER a couple of hours every evening and weekends. When you bootstrap, you decide your own timeline.

5. Pivot and budget. Sometimes it’s not going to work so be prepared to put your business on autopilot (if stable), rework it or just kill it early. Cattle not pets. Businesses are tools; nothing more.

6. You will have to sacrifice something so work with your family to know what those things will be… less going out with friends, less TV/gaming/music festivals, less vacations, less spending, etc (See #1)

Best of luck


I would throw in one caveat - at least consider delaying launch until your youngest is in kindergarten. You probably won’t be fifty, it’s not that long. Certainly do some legwork ahead of time, but in my experience the earliest years have the least wiggle room. I seriously burned myself out trying like hell to do it all, and in retrospect wish I’d have paused several ambitions for just a few years. In so doing, I’d have been fresh & ready the moment wiggle room returned.


I also took this path and have yet to really succeed. I am now 45 and an empty nester. I wrote about some of my failed businesses in this blog post titled, "How to Lose Money with 25-Years of Failed Businesses".

https://joeldare.com/how-to-lose-money-with-25-years-of-fail...


I disagree with your advice, because it amounts to "sit around and do nothing, give up on your goals."

I know someone who has a family who stated a side business in their spare time in their 30's.

It started extremely modestly using just some spare time, and I think a lot of people have at least some spare time. The average person spends, what, 4 hours a day watching TV? If OP has an hour a day they can make at least some progress.

This person also uses freelancers to help achieve chunks of work where they aren't experts. A modest amount of savings can pay for some of these deliverables.

I know someone else who sells baked goods at farmers markets. They put some time into baking and posting to social media but it's a side gig. Another person I know got together with a group to help share the effort and they're working on a hummus business (again, selling at farmers markets). These are all people with families and day jobs.

Instead of that fatalist do-nothing advice of "wait until you're an empty nester," I'd say "start small." Don't expect to be a massively scaling SaaS thing. Don't expect to replace your income, certainly not within ~5 years. Don't try to build some wildly complicated product. Budget your time, don't neglect your personal life. Focus on solving a simple pain point for a specific type of customer.

The other thing I'd warn OP about: don't start a business for the wrong reason. The wrong reason is dreaming of a lottery ticket out of wage slavery. The right reason is that you've identified an area that you think has potential to help someone else achieve a positive outcome, especially an area where you have some kind of expertise.


I agree with a lot of the sentiment of your comment, particularly about introspecting and understanding what your reason for doing a startup is. I think that's very good advice.

However I don't feel that "being a solid professional making a solid wage, and be a good parent and partner" amounts to "sit around and do nothing, give up on your goals." I feel like the advice I gave is "wait until the time is right", which is different from fatalist nothing-doing!


I still think your original comment was way closer to "don't bother trying " than that.


> Then do an awesome startup when your kids are out of the house, you have a solid nest egg, and you can take risks again in your 50s.

Then figure you have 10-20 active years left, and do you really want to spend 5-10 of them on a startup?


A lot of people do! The average age of a successful startup founder in 2020 was 45: https://economica.org.uk/research-the-average-age-of-a-succe...


Successful != typical, or even average in this context when referring to folks that start.

If you’re looking at starting, it’s helpful, but it’s important to not delude ourselves either.

Having more life experience helps, but when the funnel has a > 90% overall attrition rate, it’s still far from a sure bet.

Part of the reason why the older folks tend to do better IMO, is it’s more likely at that age that they know their own capabilities better and are less likely to launch down a path they’ll definitely not succeed on, and the numbers reflect that more.

It doesn’t mean automatically everyone once they hit that age will have those odds.

There is a lot of self-selection bias going on.


Possibly some but not that much. The linked research states that the age is still up at 42 when you remove "successful", and still 40 if you then add "software".


Interesting, thanks for the correction. Apologies for not RTFM’ng first.


I'm not sure I understand. But I think my answer is, "yes, I would!"

By that point, hopefully I have enough self knowledge to understand what motivates me and what my true competitive advantages are. I also hopefully have a strong network I can leverage to help me with any blind spots I may still carry. And to spend 5-10 years working on something that I truly am passionate about, which I've worked hard to have the resources to do without encumbering others, sounds rather nice!


As someone close to 50 in this boat it a great question.

The fact is I wanted to build a startup to get rich. That's it really. Now that I am much more finically secure (but not rich by a long shot) I'm not sure I will want to roll the dice or just keep my job as an IC.


This underestimates longevity a bit: a 55-year-old in the US has a life expectancy of ~26-29 years (male and female, respectively).[1] Granted, this may hinge on what you mean by "active" years.

[1]: https://www.ssa.gov/oact/STATS/table4c6.html


For some people, spending 5-10 years on their dreams in their 50s is totally worth it.


I’m curious, do you have kids?

My perspective changed when I had kids. And I had kids close together, Matter than friends to boot.

Mostly I realized how’s much time I was wasting to that point in life and I stopped.

It’s perfectly possible to do a startup at any age. Know many people who do and have.

Kids were a perfect prioritization and decision aid in my case. It makes you perfectly serious about doing what needs to be done. Innovation can happen just fine with constraints.

Leading up to it if you don’t have good adult habits and skills you probably some be a lasting successful entrepreneur anyways.

Doing a startup is a lot like being responsible for a baby. Some things need to be done whether you like them or not. Status aren’t just about working on the fun parts.

Getting it right also means making sure you are the kind of example you want to be for them to take their own shots. Sacrificing parents can better a sense of sacrifice in kids and it might be a cycle someone is looking to break.

Would there be more time before kids? Sure. But hard to find people in their 20s a made the most of their time beyond chasing every shiny thing. Generally our standards for how we spend our time are lost in our 20s and improves as we become more well rounded.

You only start getting good and dangerous in your 30s and 40s. It’s why so many vcs are older, they buy the years of young people and are ok if it goes no where.

If you don’t want to be a statistic, you can look at bootstrapping smaller and then growing. There are funds like tinyseed and others that specialize in it.

In your CV 30s you probably have insight in an industry need that you could bang out and have making money per easily to transfer to the next thing. HN might not be the place for this kind of thought especially if it’s orthogonal to the vc echo chamber that attracts a following and needs a decade to see in balance with other options.

If success is freedom of time, attention and resources where you want to put them, the path of startups as you are implying (likely funded) might not be compatible with you.

Todays the youngest you’ll ever be. If not now, then when?


I do, thanks for asking! I am the proud dad of a 22 year old son :-)

I definitely agree that having a child can be a spectacular forcing function for focus for some. I unfortunately also know folks for whom having a child was the proverbial straw, and whose life fell apart afterwards.

I was running my own company (RFID and industrial automation startup) before him. When I became a dad I found a corporate job. The worry around healthcare costs for a family as an independent were simply too much for me, even back then. All in all, I feel very fortunate in how it all worked out for my family.


I completely understand and see where you’re referring to with having kids being the proverbial straw for some.

It will shake the trees and see if we’re as solid as we think you we lol.

The thought of a cushy corporate job and what it pays compared to the average payout from equity in a startup isn’t too far apart pretty often. I have done stints of consulting when I needed to do market research and it was a nice way to deep dive to find the no brainer things a business would pay for.

Healthcare is no joke. I’m very lucky to be based in Canada from that perspective, even if it’s geospatial further from some tech things that interest me - travel is a fair compromise.

In my case the dip and test didn’t hit until they were 15 months, and it was interesting that I made it over 2 years including the pregnancy before wanting to check in.

I rezzo you have hand keep the itch alive to work on hobby projects. RFID and industrial automation is a cool area that I got to experience alongside someone on a project.

Last but not least happy to receive any parenting advice


If only anyone knew what that one awesome startup was.

Its the market that drives businesses. If I wait too long to even start trying, chances are slim that I ever will try, markets change you know

On the other hand, if I wait, building a business off the network and skills and reputation and market knowledge I've built, has a higher chance of survival.

My philosophy is to be non-dogmatic but probabilistic and opportunistic. If you see an opportunity, try it out, take a loss maybe, and learn and try again.

Like a good gamble, you need to spend most of the time at the table, in the game before betting big, not working in the shop next door waiting to get in.


My situation isn't quite the same, but it is leaving a well paid job when I have two kids and a mortgage in order to work in some to-be-determined field where I have no experience, with no opportunity (after a short window) to return to my former field if I change my mind.

First, have some savings and a plan to minimize burn rate if things get tough. More importantly, there needs to be a compelling answer to what you're accomplishing for your family, or what you as a family are accomplishing, by making the change away from your present comfortable arrangement.


Disagree. Not every startup has to be a massive success, not every founder needs to be a billionaire, and not everyone has to work like Elon Musk - you’re probably not sending rockets to Mars.

OP might be very happy with a company with no employees that makes 200k a year.

To the OP: save up for 6 months of working on your own thing, OR, launch loads of little experiment MVPs that don’t need lots of work to get _something_ out quickly.


totally agree, you just DONT

I sold mine and waited 10+ years until kids are in the last two years of high schools, I also saved a bit during these years so I have some cushion to restart my startup dream. Maybe it's why there are a group of entrepreneurs in their late 40s and early 50s just like what I had?


The upside to waiting is also gaining experience. There's something to be said to learning in environments that work before taking a stab yourself. I'm sure many founders over 40 avoid many mistakes this way


Only problem is when you are 50s you are likely to have the time and money but not the energy. Surely it is not the case with everyone but enough to have this cliche pass around for quite some time.


And that is why it is rare that it happens. Which is fine, it’s not a ride many people would even want once they have the rest of their life stabilized.


> you are 50s you are likely to have the time and money but not the energy

who do you think initiated these "startup" patterns post-2000 ? It was boomer+ investors using vast investment pool money, in the last 20 years.. now they are dying off and it is on auto-play via "don't get creative" money builders.


Thanks for writing this comment. It is actionable, excellent advice.


> My very concrete feelings on this is that you probably don't.

The ones that do - and usually the few in this age group that succeed - are already independently wealthy from a combination of having a highly successful career and making good investments.

People that have $1M+ to fall back on - and can easily land another job making $400k+ - if things don't work out.

You don't see too many 35 year-olds with 3 kids and no savings starting Ubers.

Every once in a while you find an Elon Musk who already had plenty of money, and decided to start another business.

People with insignificant amounts of savings starting successful companies are almost exclusively in their teens or 20s.


Well, you definitely don’t see any smart ones doing that, and for good reasons.

Is it impossible with a stressful job, a bunch of kids, etc. and not being independently wealthy to do it?

Not necessarily, I guess?

It is definitely not a good idea, however, and it’s highly likely to implode one of those other areas of their life.

And frankly, it isn’t a good idea for the vast majority of independently wealthy folks either. The types of pressure and lack of structure in the environment can and does mess with peoples minds, and can encourage them to end up a lot less wealthy at the end. If they’re particularly unlucky or mess up, even with expensive legal issues following them around.


VC here. If you're building a bootstrapped business, then starting as a side project and building up revenue until you can go full time is probably the way to go.

If you're going the venture-backed route, I think there's a misconception that there's no salary or minimal salary at early stages when you're funded, but this is not true. Most founders take a reasonable salary, where reasonably is defined more by your personal needs than anything else. $100k-$150k salaries are pretty common at seed. That's not Google level, but it's not bad. Here's a thread on that: https://twitter.com/lpolovets/status/1365123608905879555


If you're not a FAANG engineer, and like 95% of people work somewhere that doesn't give you a ton of stock or RSUs, and you don't live in a super expensive metro, $100-150k is basically strong mid/weak senior money. I know plenty of places hiring with no stock, no bonuses, and seniors top out at $160k or so. They hire capable engineers no problem.

With that in mind, taking a pay cut into the middle of that range to do your own thing and potentially make a lot more isn't as drastic as going from a $400k FAANG job to a $35k ramen-every-meal situation.


I think the problem is not the paycut, so much as you suddenly work 80 hour weeks and never see your kids.


If it's your startup, choose a location to work that's close to home, and have the kids come over.

I fondly remember running around the overly large halls of various companies my dad worked for which were startup or startup adjacent.


This brings back fond memories of playing tag with my brothers through the cubicles where my dad worked when he had weekend work to do, complete with a vending machine room and some desks that had bowls of M&Ms. It was great fun!


Would love to hear more haha, sounds like your dad did a good job juggling it all if you look fondly back on it


Well, my three brothers and I ranged from ages 5 to 10, so that's a good starting point. Then figure it's a bunch of long narrow hallways, which were wide enough for kids to run in, but narrow enough that you feel fast running along the walls. Low-pile office park carpet turns out to be perfect for traction when running in your socks at that age. And then M&Ms and vending machine stuff is the perfect treat for kids who mostly ate homemade meals.

I'm sure the two most uncommon enablers of the good experience were 1, there being four kids in the family to play together and, 2, my dad not worrying that we were going to cause a bunch of problems when left to run around the office.


I'm doing this by starting an all remote start up. I can hear my son playing downstairs or outside, while I get to dedicate myself for a while. I'm actually able to make it to more of the important times, now that I'm not commuting, even though I work long hours.


Yeah, the when of long hours can be much more important than the long hours themselves, especially depending on kid ages.


This. My son is only 4 months old and between all the naps and feeding, it's maybe only a few hours of actual time actively spent doing things with him. But I do have the luxury of being home all day so I work during his downtime.


Or better yet recognize that it's 2022 and just work from home.


Work-from-home can work great until you have a group that is working together; but even then you may be able to arrange something (house with outbuilding, etc).


> work 80 hour weeks

Hasn't really been my experience. There can be the odd extra evenings or even weekends, but nothing drastic.

The big difference in hours is probably how effective those 40 hours a week need to be compared to a big company.


Are we even allowed to do side projects? What if our employer claims ownership or even conflicts of interest with what we are building? How will i even present it into hn or producthunt with my name and all my credentials while i am still working somewhere else? Any employer would fire us on the spot if they found out, wouldn’t they?


Here [1] is a story that shows a possible scenario of what might happen if your boss fears your side/open source project and believes it directly competes with his company's main mission. Fortunately, the story ends in favor of the engineer.

1. https://news.ycombinator.com/item?id=27424195


Depends on the employer and where you live... you may have to get permission or specific exclusion when you start a job. As long as there isn't overlap with the business in question, I haven't experienced an issue working on the side.

Note: working on the side is not drawing multiple FTE salaries... but actual work outside business hours.


I don’t know, the conflict of interest especially in saas is tricky. Let’s assume that I build some niche etl tool, my employer deals with data etl for a certain market, how can i safely determine that my side project doesn’t interfere with their business? Not even lawyers can determine this. And what about the working hours overlap? Who knows except my commits to my repo and myself? I don’t know, side projects seem like a bad advice as they probably increase current job insecurity imo..


I specifically called out "outside business hours"... there should be no overlap. I also don't tend to work on anything near what I work on at my day job. Same for side work to main job.

Again, it depends on the work environment. I haven't had trouble getting permission when I've wanted/needed it. It's generally if your job performance is suffering, or if you are working in an adjacent or competing market.

You've specifically mentioned two things I believe I excluded in my statement.


You claim it as IP that is previously developed when you start the new job or you submit it to your current employer and get an IP exclusion.

I’ve done both with no issues.


The answer is, it depends. Different states have different laws etc...


Also check what your contract says. About non-compete clauses and exclusivity clauses.

If it’s green lights everywhere I will advise you to have another GitHub account than your professional one. And makes everything as separate as possible.


unless you have registered your invention with the employer during the hiring process, it belongs to them


Not true. If your project does not compete with your employer, you do not use their resources, and you do not build it on their time, it is yours. This it the case in California. That doesn't work well at a FAANG because they have their hand in so many pots it is easy to compete with them. Anywhere else, just work on something not related to your work. I'm in security and build in AI.


Incorrect. Without going into all the nitty gritty, even a lot of FAANG companies have explicit moonlighting policies that are fairly permissible.

At the one I am at now, you can get a written sign off from legal before you even start your side project, where they agree that all rights to the side project belong to you. You have to apply for each project individually, but the form is online, just a few fields, and is commonly approved (as long as it isnt a legitimate conflict of interest). I don't mind the process, because each time it nets me an official signed paper that explicitly states that my employer has no rights to my side project.


This is only situationally true, both in terms of employment contract and jurisdiction.

Rule #1: don't listen to sweeping statements about law on HN.


I think I understand what you mean. Bootstrap = use your current salary. VC = use startup funds to pay yourself but it gets touchy real quick.

I currently make 140k in MCOL, so to hear that taking a 140k salary isnt out of the question, eventually, is reassuring.


I think the toughest part ends up being the time between when you leave your job and when you raise your first funding round. That could be a 1-2 month gap, or it could be a year. Best advice there is that you can probably do some of the initial startup work while working somewhere (e.g. customer interviews, spec'ing out a product, recruiting a cofounder, maybe even launching something), so that when you leave your job you can do a fundraise soon and have decent confidence in the company you want to build.


My startup CEO takes home like $500k. lol!


lol founders taking a salary... I got 5 startups for you to fund!

Founders need to show a lot of work done / churn to get VC backed.


right. as if seed rounds grow on trees


yeah dude just "take" a salary from your seed round. lmao


Very rare for an investor to want a founder they invest in to be constantly worrying about money. Very good signal you shouldn’t be working with them if they don’t get that.


the point is getting a seed is hard


As someone who tried and ended up broke and divorced...

You have to really know the business you are trying to break into and make your goals really attainable. Think in terms of figuring out how to generate even enough to pay your phone bill each month, then move up to a car payment, then to a mortgage. Build in micro-steps, making sure that you have stability at each level before you move up. Can you do parts of the business without building anything, IE: via spreadsheet or email, or a simple Wordpress site rather than something more elaborate? Partners are complicated - on one hand they lift the burden of doing it all yourself, but now you have a business relationship to manage; there's got to be a lot of trust there.

On the other hand - there's never a good time to do anything. There will always be a reason why now isn't the right time to pursue whatever you are considering. And, your spouse matters a lot. Whether they are supportive of who you are and what you want to pursue in life is one of the key ingredients of potential success. I'm not suggesting you trade one for the other, but you'll need to be very candid with each other about your goals and needs. Don't try to parent and spouse and career at the same time - dedicate time to each and be very clear with each other about which "mode" you are in, IE: spend Saturday completely with the family. Make sure you are supporting your spouse and their career / personal needs, but also set a rule 5-10 M-W-F is your business time (IE: whatever it is that works for your life schedule and needs)


I agree with all of this. Fortunately my spouse is very supportive, she just doesnt want to become destitute, and I cant blame her.

Also fortunately, we are both boring homebodys and she wouldnt really have a problem with me working on this every night.


I think that's the key - you do it via bootstrapping, and you DON'T kid yourself that you're building the next Apple Computer in your garage. As long as you keep your goals reasonable, it's hard to tell yourself that stupid sacrifices are worth it. (Most people would spend a year in Antartica with no phone for $AppleFounder, but would likely not do it for $moderate income, for an exaggerated example).

But be constantly aware that your main "customer" in your life is your spouse, and then kids. People put up with a lot without making it clear, often.

Someone as an outside observer who can tell you that you're starting to screw things up and you will listen can be incredibly valuable, both for the startup and for the family.


Hi OP,

I was thinking about what you are asking as well, but now I solved my problem other way - I employed myself in the company I identify with, I mean I believe in what they are doing and want them to succeed. This allowed me to get the feeling like I am part of the company; it's not exactly like "this is my startup", but similar. I already do not crave to create my own startup.


My friend and I started it as a side job, working nights and weekends. We also downsized and cut all our expenses to about $1,000/month (mortgages were smaller back in 2005).

We quit our full-time jobs when 1Password revenues were close to $80,000/year.


You mean 1password.com?! That's amazing great work. Huge Canadian success story [1]. You're definitely underselling the achievement here but guess it's funny to look back and were probably super excited about that first 80k. I imagine there is probably a books worth of war stories about this.

[1] https://financialpost.com/fp-finance/toronto-based-1password...


Thank you so much! It was certainly a new chapter for us, working directly for our customers and being able to live on the product we made.

Great story. Did you have a family with kids at that time as well?


Thank you! Yes, Natalia and I had two little kids and Dave and Sara just had a newborn at the same time

This is a good point - reading up on FIRE https://en.wikipedia.org/wiki/FIRE_movement can be useful - perhaps with some intelligent allocation of resources and time you can start bootstrapping today and five years later have the mortgage payment eliminated.

And if you're serious about doing a startup, do consider moving to an area that will have what you need but is cheaper.


This is inspiring and what I'd like to do, too.

I'm working on downsizing and reducing expenses. I'll have repaid a credit fully next year, that allows me to increase savings etc. Slowly those things come together.

Also trying to create small side hustles, bootstrap them, hope that something sticks and try to scale that up till I can quit the corporate job and focus on things I'd love to do.

It's probably a longer journey than expected if you've got no money advantage.


This is awesome, great to hear! You are absolutely right at trying different things. Best of luck!

Kudos! Long time user here! Love 1password.


Thank you <3

I'm the founder of a venture-backed company in my 30s with two young kids under five. My co-founder is also in the same boat. A few points:

1. My wife works in a well paying field (nothing crazy, but comfortable), and we were financially stable enough to be able to live without my salary for a couple years.

2. We were very customer focused from day one, even before we incorporated. We signed up several customers (using LOIs) with just a deck, before we wrote any software.

3. We discovered a very clearly defined problem, a payer and clear willingness to pay.

4. I don't work like I used to. I feel much wiser about how I spend my time rather than brute forcing it with hours. Because of the two kids, I effectively work 9-5, M-F. I don't work weekends. During 9-5 though, I am dialed-in (I don't spend time reading the news or checking instagram). I delegate much more aggressively than I used to. I don't think I'm actually outputting much less than I used to, I'm just more efficient and focus on the more important things.

5. Venture - this is what it's for. There is still a bunch of venture out there for seed/pre-seed. We raised money early on and that allowed us to take small salaries (and hire folks to delegate things to).

100% it's definitely not as easy to start up in this stage of life, but it's also not impossible. Happy to connect with folks who want to connect (commiserate?) about this situation.


> 2. We were very customer focused from day one, even before we incorporated. We signed up several customers (using LOIs) with just a deck, before we wrote any software.

How did you find these customers? Existing network or fanatical prospecting? Did you, your co-founder, or both close the deal?


We called them and asked if we could come visit in person and learn more about their business. I think you’ll be surprised how open people are to help - especially if you’re curious and let them talk about themselves.


Do you feel like that because you were once a professional, that it helps with the startup? As in, does it help you avoid useless nonsense that doesnt add to the bottom line?

Also the time management piece is ultra important here I think. Its like Leetcode for time management. Theres leetcode easy which is just brute force working hours, then theres more efficient ways of working that become more obvious in a professional setting. Its the one thing I have over myself when I was 24. I know how to manage time more effectively.

Do you feel the same way?


There are two aspects here:

- being efficient with your time: not wasting time on distractions, keeping meetings short etc.

- knowing what to spend time on: doing the activities that will actually drive to your goals rather than feel like you are.


Hey, I'm Jens. I'm 34, married, with two kids (1 and 3), and I'm also the founder of WunderGraph (https://wundergraph.com).

I've done exactly what you're trying to do. Let me give you the playbook.

In preparation, I've done years of research in the field I'm working on (APIs, Integrations, developer experience). So you need a clear advantage.

Next, choose a topic that you're thrilled to be working on for many years. Doing this means you have to eat a lot of glass. It's crazy.

Commitment. Be ready to work through weekends and nights. You will feel bad because you won't have time for kids and wife. Your wife must 100% support your endeavour. It will be tough. Don't kill the relationship.

You need co-founders. Don't try this alone, it sucks. Build a small team around you. I found 3 amazing co-founders, a COO, a marketing genius, and a hacker. You can use tools like YC cofounder match. A lot of people will be a bad match. Meet a lot of them and try out things.

Build whatever you can to get one single customer, that's a person who pays you money. For us, this was enterprise support from the first customer at $2k/month. This changed everything.

How do you do this? Fuck everything. Stop building. Talk to potential buyers. Get someone to give you money for what you're doing. No money, no value. Whatever it is, get some MRR.

The last one was my biggest issue. I kept building because I loved building so much. But I was just coding, not creating Business value. If you're able to ship any kind of MVP with your co-founders, you're able to get some MRR, that will give you angels, and finally you can raise a seed.

All of this can be done on the side. Keep your job as long as possible. Get that one customer, get the angels and a SAFE for 6-12 months and then double down on that first customer, improve the tool, get a second customer maybe and raise the SEED.

It's possible. It's going to be tough. But you can do it. If you need my help, I can mentor and give you the right intros. Best of luck.


Hey OP here, thanks for all the advice and the offer at the end. However I am nowhere near ready to start down this path so maybe way down the line ill send you a DM haha.


Way back in the year 2000, when you and I were kids, Joel Spolsky had just finished managing the addition of VBA into Excel 5.0 and was quitting Microsoft to start his own companies like StackOverflow, FogBugz, and Trello, and wrote this illuminating blog post:

https://www.joelonsoftware.com/2000/05/12/strategy-letter-i-...

> Building a company? You’ve got one very important decision to make, because it affects everything else you do ... Whether to grow slowly, organically, and profitably, or whether to have a big bang with very fast growth and lots of capital.

Unless you have a trust fund to fall back on - and it sounds like you don't, with the mortgage and job and all - you can't gamble with your responsibility to your family. Your answer to the question above must be "slow, organic, and profitable," you have to abandon the dream of becoming a gazillionaire with the next big risky "Tinder but for carpooling" idea. Even if you think you have a 10% chance of becoming a billionaire and a 90% chance of losing your house and destroying your family in the next 10 years, versus a 100% chance of holding a boring $100k/year job, the former is not 1000x better than the latter even though the estimated iterated return is $100M/year.

You should either learn to be content at your ordinary job, or you should slowly build yourself enough of an emergency fund/runway to be unprofitable for 6 months to a year, and give a safe, organic, slow-growth business a try. You can call it a "startup" if you want, but you can't burn VC money like it's going out of style. I have no idea what you do, but perhaps building a network of contacts during your current employment, and starting an independent consulting business could work?


At 34 (but with no kids) I agreed with my wife that I could have 4 years with a sanity check at the end of year 2.

I also agreed that it would be an ABSOLUTE rule that I could not put any of my own money into the company. This included the $10 for buying the first domain.

I ended up selling 20% of my company to a friend for $5k when it was just weekend hacking with him getting diluted to a $2.5m valuation once I've been full time for 40 months.

[Edit] It massively helps that my wife is a partner at a law firm so we can pay bills etc, without having to have saved the cushion in advance. I also arranged to leave my previous employer with a 6-figure exit payment.


> It massively helps that my wife is a partner at a law firm so we can pay bills etc, without having to have saved the cushion in advance. I also arranged to leave my previous employer with a 6-figure exit payment.

I'm happy for your success, but I feel like this should have been mentioned up front. This kind of massive leg up almost certainly does not apply to OP.


Fair, but there's lots of other things that get missed when trying to give short feedback.

I have a degree from a prestigious university and I've built relationships in the area I'm now trying to do business. I joined a golf club and a yacht club, I made friends with a former CEO of an NYSE listed company, I watched all the start-up school curriculum videos, I've been repeatedly rejected by YC (though we got an interview one time) which means I think through what we're doing every 6 months. I made friends with a journalist.

There are a lot of things I've done that wouldn't be available to someone with low social or financial capital.


At which point is YC not worth the effort. You come off as being well enough connected to organically contact VCs.

I've largely given up on the business side. I make small games I hope people enjoy.

Not that there's tons of VC money going into video games anyway...


Hey, what's your gaming niche?

I've been trying to hunt down decent iPhone/Android games with decent polish/production values and no sinister monetization, but it just isn't working out.. Not counting Apple/Google/Netflix subscription options, I've only found maybe half a dozen games that are high enough quality that they could make it on a game console or PC.

I feel like this is an untapped market again, since some of the most successful and most popular games out there treat their customers with respect. Or at least, did at one point. The issue is that there's no way to discover games like that for customers, and no funding from publishers to make them.

(I wish I had some clever idea about what to do to re-energize that market.. I was thinking to make a review site a la TouchArcade, but I have no idea how to get it to take off and there aren't enough games to fully populate a site like that)


I'm making ultra small games like infinite runners, and other procedurally generated generated games.

The problem is risk vs reward. Even a modestly sized game will cost millions since you need to compete with some of the biggest names in the industry.I really tried to make a graphically intense game with Unity's HDRP, but I'm still not able to match the polish of a AAA game.

Aside from that, there's too many games being put out right now. People only have so much time and money after all.


> I'm making ultra small games (...)

Hey, many of us like small/ultra small games!

I used to play a lot when I was younger (back in ZX Spectrum times), but now don't have the patient (or time) for big games that require any kind of commitment. For instance, I played occasionally sudoku on my tablet/phone and when I started to play a little bit more I bought this sudoku [1] for both Android and iPhone. I also play occasionally some games from these guys [2], namely "Smash Hit" and "Pin Out".

What are your games? Share a link, maybe one or two of us may get curious and play with it a little bit!

[1] http://www.enjoysudoku.com/

[2] https://www.mediocre.se/


That's what really kills me. There are so many great devs out there making awesome stuff, and I can't **ing find any of it to play because I'm constantly being bombarded with terrible big corporate shovelware casino crap

ah well, I hope you strike it big!


I'm open to ideas on monetization.

I don't need to strike it big, 500$ a month would be more than enough to motivate me. Hell, 500 plays per month would be enough.


> I also arranged to leave my previous employer with a 6-figure exit payment.

How does that even work?


Throughout my career I'd survived 7 redundancy rounds. One time I chose not to survive. When management raised the idea of moving my team to Ireland I negotiated for exit payment rather than making the usual case about how important my role was.


Were you in fintech or other highly classified work? I've only heard of employers paying (former?) employees for basically a year of their salary on "garden leave", where the employee is kept on the payroll without doing any work in order to prevent them being able to bring trade secrets to a competitor


I was a data scientist at an insurance company. Was a fairly standard redundancy based payment but with a little bit extra to avoid it being a redundancy and to get a mutual non-disparagement agreement. Basically the bonus for the year, 3 months garden leave, 8 weeks redundancy pay, taxes, pension contribution, and share scheme buyout etc.

When I'd avoided redundancies at previous employer (large bank) some really great terms had been offered.


I just did this. I had 2 very important things that helped me succeed in starting.

1. A supportive wife 2. A wife that can pay the bills while I take 0 salary to build something.

Without those 2 things I wouldn’t have been able to start.

As I’m sure you realize now that you have a wife and a child your free time is limited and at bad times. So if you want to actually be able to accomplish something you have to pull real time away from something else.

Your choices are 1. Your family 2. Your job.

You could try going part time and asking if your wife is willing to do an outsized portion of the family work but that goes back to (1) being critical. First and foremost you need a wife that will support you.

I know this probably isn’t helpful but it adds a datapoint for you.


I'm currently experiencing this with a 3 month old startup (I'm the CTO) Two years into a marriage with a 6 month old kid,

My experience:

- It's hard, if your playing a video game it would be in `very hard` mode

- Talk to your wife beforehand, she was okay with the opportunity

- Had a LOT of savings

- Have a co-founder (highly recommend it)

- We've raised preseed money (co-founder handled all of that)

- I hired an ex-coworker that I worked with previously (that's why you raise money)

- I'm remote so I get to spend more time with my baby (if I'm not productive during that day I try to code long nights and usually feed the baby during the night so my wife rests)

Overall it's been super hard but gratifying :)

PS: I also try to exercise for an hour a day to keep me sane


Hi there! I'm someone currently doing this. I'm CTO at a small startup in Oakland, am married, have a 4-month-old, have a mortgage. CEO just turned 40, also has a mortgage, is married, and has two kids.

Like everything, there's tradeoffs in time and money. Will you move faster if you're spending all of your time hustling on the startup? Maybe! Not every business and not every startup requires 24/7 hustle. Does this force ruthless prioritization? Yes. That's a good thing!

It also means my cofounder and I are very cautious in hiring, using offshore contractors anywhere we can, because we know that the pool we're dipping into is legitimately our own salaries. This is also a good thing! Paying yourself enough to live on without stress and keeping all other expenses low and tight is still "running lean" in my book.

Ok, so how: We got lucky of course, but some of that luck can be replicated. My CEO already knew some VCs from previous networking; those VCs gave us some pre-seed working capital, which allowed us to build enough to get more VCs on board, which gave us a year+ of runway to keep building. We did a _lot_ of pre-vetting with our target market before building, and the nice thing about pre-vetting is you can do it while you still have a job working for someone else.

The thing to remember as a founder is that part of why tech companies provide great salaries and so many perks is so their employees can be at work and fully focus on the work. You should treat yourself like a valued employee as a founder, and create the conditions for you to do your best work, which probably means not stressing about paying the mortgage.

The hustle and drive should come from your passion for the business and the approaching zero cash day, not forcing your family to live on ramen.


The right time to work on a startup is any time when you have identified a real problem to solve through your overall work and personal experience. When something occurs to you that seems clearly obvious as a need, backed up hopefully by some data from potential customers.

The wrong time to work on a startup is when you just have a vague desire to work on a startup but don't have the passion for solving a specific problem but just feel a vague pull towards startups. In that case, you are much better off joining someone else's startup.

You can make long hours work out with family life and having kids, people do it all the time who are not involved with startups but work multiple jobs, lawyers who work long hours, etc.

Long hours per se is not the issue, spending those hours on the right, productive thing is the issue.


> if I told my wife I was leaving my job to pursue a start up

Maybe I'm reading too much into this, but is the plan to make a decision and then telling your wife your about it? If no, then you can skip the next part.

If you answered yes, then I have one suggestion for you: ask your wife how she would feel about you perusing a startup. If a startup means dealing with financial risk, more work, less free time, have an idea about how you would handle that. Many founders' startups are built on the sacrifice of their partners' labor, time, and careers. This often goes unacknowledged.

Think about how you would feel if she decided to found a business and told you that you would have to start making sacrifices? If you are thinking, "That is something I would like to have input on," do right by her by asking her before making a decision. You signed up to have a partnership, right? That means meeting her as an equal in the decision making process. This isn't an opportunity to convince her either, it's an opportunity to explore the second and third order effects together and decide together if this is the right move or not.


Where in the world do you live and what social security systems are in place? What savings do you have?

Why do you want to start your own company? Is it because you’re sick of answering to people, or because you believe you have a genuine solution to a genuine need.

Aside from all of these points, the brutal reality of starting businesses is that it can be very risky and capital intensive, if you have doubts, you should consider why.

Over in the UK, many in the startup scene appear to be from upper middle class backgrounds or ex-bankers/finance. These people have security through assets they have inherited or earned.

Aside from that, you can be a contractor and grow your customer base from there, this is likely to be less risky.


Rob Walling coined the "Stair Step Approach" as a way to get yourself into startups in a lower risk way:

https://robwalling.com/2015/03/26/the-stair-step-method-of-b...

He has also talked about it on his "Startups for the Rest of Us" podcast:

https://www.startupsfortherestofus.com/episodes/episode-222-...

Might be worth trying Rob's approach before leaving your job and betting the farm on a startup idea...


Definitely listen to StartUpsForTheRestofUs.

Do not leave your job! There are lots of ways to begin your journey to having your own company/startup.

Being employed is a great source of bootstrap funding.

I also highly recommend @DHH startup school talk. https://www.youtube.com/watch?v=0CDXJ6bMkMY

You have plenty of time. Save up and use your 'extra time' wisely.

Rob's stair step approach is a great way to get started.


Went through this with my SAHM wife and one (and then two) kids. It was difficult but rewarding.

First, make sure your partner is onboard and is supportive first. Have the discussion about the sacrifices needed to make it happen (time, money, lifestyle shift, etc.) Something that helped us was to set a goal of what we wanted when things eventually worked out. This kept us sane and helped me continue to be motivated during hard times. We lived in a pretty low cost area (NC) and managed to get our expenses down a lot.

I also made sure to spend my weekends with my family and my wife. I took over a lot of the chores on the weekends. Communication was key for us and when issues came up, I tried to resolve them ASAP.

Start working on your startup between 5 PM to midnight. Bootstrap it as much as you can until you can make ends meet, then quit your full-time job. Apply for YC and others while still growing your business if you think it has the scale. Eventually, it either works out well or poorly.


From my experience founding companies, you've gotta commit 100% to it to have any chance of success. That doesn't mean working on an idea in your free time. Consider the fact that someone, or even a funded team of someones, are out there putting in 100% effort to solve the same problem. How are you going to outcompete if you're working on this problem in your spare time (which I imagine is quite limited having a wife and kids)?

You should also consider what success looks like for you. Do you want to start a company to gain creative freedom? Do you want a better lifestyle for your family? Are you prepared to spend the next 7 years on this endeavor? How will you balance the high workload (I'm talking non-stop work for a month at a time) with spending quality time with your family?

You should think through all of these questions, then have an honest conversation about it with your wife, and don't sugar-coat it. She might surprise you.

As far as funding goes... You'll want to put away a fund to pay your salary for at least the first 6 months. Your goal in those first 6 months will be to create a believable story you can sell to investors about your vision. If they like it, you'll be able to raise funds to continue working on it and to deliver that vision.


> "As far as funding goes..."

An alternative version would be to spend the first months trying to sell the product to customers even before it exists. Try to validate as soon as possible, then build and deliver the product.


From my experience founding companies, this is only true for high growth companies. There are loads of lifestyle businesses that make six or seven figures that were started on the side. It’s super hard if you have kids and a full-time job, but many have done it.


Just my $0.02: start a side project and work on it evenings/weekends, while keeping your day job. Yes, it will be tough, but delaying it is not the best idea, since working overtime without burnout gets harder and harder as you get older. Make sure NOT to make the mistake of focusing only on the more enjoyable, technical side of the undertaking (read: exciting technologies and software development), but pay a lot of attention to the more boring, business side of your project (read: educating yourself on product/market fit, initial marketing strategies, growth hacking, etc.) Find out whether you are going to even enjoy the non-technical, business side of a startup. Realize that since you do not have a lot of money to burn and/or a lot of time to clock in, you will have to avoid huge mistakes and develop a very good business idea and a very good Minimal Value Product that will let you FEEL at least SOME startup traction early on; otherwise, if your side project never gets at least a bit exciting relatively early on, you will just get tired of it all and dump it. (Or not, which would be a valuable lesson as well: the one that you get addicted to running your own businesses.)


Maybe you don't. I'm not sure you can have it all: security, high salary, start up, huge upside, free time for self and family, oh and sleep and sanity.

At least, if you assume you could have it all, there's a good chance you'll come short notice n a few categories.


Can you educate on why the existence of wife and children is such a burden? Is it social committments? Children don't take up 8+ hours a day after 1yro+ And wives... get one that understands stuff like this?

I ask because I know multiple talented people using this as an excuse to not use their abilities as they claim they want to.

My ignorant guess would be people these days think you need to spend a ton of time with your family because other people blame their problems on absent parents? That's why I'm asking to be educated so I can be less ignorant about the burden of parents. Naively, if I had a kid (not that I plan to, don't worry lol) I wouldn't care about spending time, just feed, clean and transport, not that much worse than pets burdenwise. I would expect kids and spouses to understand the nature of the real world (when they grow older for kids).


> I wouldn't care about spending time, just feed, clean and transport, not that much worse than pets burdenwise

This stuck out to me. I'm not sure if you're serious, but I'll bite.

Kids need more than pets. They're people, not a puppy. You can't just leave them to figure it out on their own, nor can you lock them in a box with a tablet and some Cheerios, although I'm sure most parents have wished they could from time to time.

They're still pretty useless after 1 as well. Barely walking, still not talking, can't read or write, definitely can't call up and order a pizza.

What will they eat? Good home cooked meals, or out of a box? There's no kiddie-kibble...

Who will clean up the mess and spills from that meal? Cleaning with kids around is like brushing your teeth while you eat an Oreo. There's about a 6 foot blast radius to every snack. Do you just let the place get filthy?

Who will help wipe their butt for that first five years? Lots of kids don't potty train until 3-4. Some are still having accidents after that. Now they need a shower too. And how's your laundry pile looking?

What if your kid has health problems? An appointment a week, maybe more? The appointment is 30 minutes away. An hour for the appointment. How's that day looking?

I could ramble on, but having little people around is absolutely time consuming.


What can I say, thanks for educating me on that. If I may ask a follow up, I know one guy whose wife doesn't work, if your spouse (man or woman) is willing to stay home until they are 5-6, how can they still use the family excuse?

You have changed my mind about the burdens of parents but I wonder how people were able to raise 10-15 kids, sometimes 5 of them will be toddlers at the same time.

I look at what you said and I see why people are having less kids these days as well, maybe stay at home parents are not supported or encouraged enough?


Have you ever had a job where you're on call 24x7x365, and nobody else can do it if you're not available? That's parenting.

Every relationship is different, but your spouse is also a person, with person needs. The stay at home parent still wants time to shower in peace, or a day where they don't feel like they play chauffeur, maid, nurse, and chef. It's a lot of work. Sometimes you need help. It is easy for it to feel one sided, and for a partner to feel like it's not much of a partnership.

If you make it through a day where they're just hungry, grumpy, and screaming as they sometimes do, and you haven't had 5 minutes to yourself that day, would you be happy your spouse was "just running a little late at the office" and arrived home 2 hours later than normal? Or maybe just after bedtime, so you did it all that day?

Numbers wise, if you have fifteen children, and five are toddlers, it's likely some are old enough to babysit. One thing I've realized about a lot of those old school big families is that the older kids spent a fair amount of time doing things parents do - walking the younger ones to school, keeping an eye on them at the park, cleaning the house, helping with cooking, etc.


I'm currently going through this process with a very supportive spouse. I quit my job last year and have been burning through my savings to develop prototypes. This is obviously very stressful, especially as, in this economy, it's no longer guaranteed that if I give up I could find a job in my area that pays the bills.

She accepts the risks and wants to see me try to follow my dreams rather than give up. We've moved back in with my parents to save money and help with childcare.

Once I can secure some investment, it should get easier -- at least financially, if not in terms of work hours. That's also difficult these days but we'll see how it goes.


I made the mistake of opening a startup with two small kids, another on the way, and a hefty mortgage. I left my well paying job to do so.

It was a nightmare. I living hell that eventually broke me and almost ended my marriage.

Don't do it.


I hope things are better for you now. It is tough.


> Are all startups at my age generally side hustles that become profitable enough to quit my day job?

Maybe yes. But that's only the first step.

40yo here, married, 3 kids (5yo, 3yo, 1yo), and a mortgage. I am more in the risk-averse side.

I was a CIO ('I' as in 'investment') in a family office. In 2019 I started building a document processing service (eg merge, encrypt PDFs) as a side hustle. It grew slowly and steadly, until, in May 2022 I got enough recurring revenue to ask my employer to reduce my load to half-time, taking a paycheck cut.

In the other half of the day, I am working in a more ambitious idea. I expect that at the time I am ready to launch, the income from my document processing service will be near 100% of my full-time FO paycheck, so I am taking very little financial risk.

Two resources that would have helped me a lot when I was having the same questions as you are:

- Rob Walling's "Stair Step Method" https://robwalling.com/2015/03/26/the-stair-step-method-of-b...

- Dan Hulton's "Evaluating Modest SaaS Business Ideas" https://greaterdanorequalto.com/evaluating-modest-saas-busin...


I would start with understanding how assets work. Buy Rich Dad Poor Dad - it's going to be extremely boring and annoying to read, but it's essential because most people truly don't understand how this works. Build up your assets so you have enough recurring income outside of salary to support your standard of living - then do a startup.

A couple of concrete examples of what an asset strategy is:

* An options strategy that helps you yield every so often (example - buying tobacco and alcohol options going into the recession hoping they will yield higher when people tend to drink and smoke more) * A real estate strategy that minimizes money exchanged in-hand (example, looking at housing markets that are starting to become distressed, buying a foreclosed property, and then flipping it to someone else who would buy it for more but doesn't check the foreclosures listings)

^ There are many examples. It won't be quick money, but you need to get to a point where your assets are generating enough money for your marriage to not fall apart in the very likely scenario that you will fail starting your own company multiple times.

I want to say, I have no idea if this is actually the right sequencing of events for you, but it seems to be if quality of living is a top concern (which makes sense). If you want to maintain a standard of living while taking on massive risk, you need to hedge with a diversified asset portfolio that generates income for you outside of your job.


I co-founded Howdy.com (YC W21) about 3 years ago. It's a platform for building your own dev teams in Latin America; automate vetting, payroll, offices, equipment, etc. We're profitable and just closed a series-A.

Here's the kicker: My co-founder and I both have kids, family, mortgages. Here's how I did it in the years leading up to and during:

- I saved for years with the idea that I was going to use that money for entrepreneurship

- I was upfront with my spouse and kids about the amount of effort, risk and potential rewards; i could point to a successful dev/PM career as evidence that I could succeed

- Keeping the same standard of living was impossible, we had to budget for a new level of comfort

- We had runway timetable in mind to show some progress

- Our business approach had to be profitable from the start

Your business failure rate doesn't need to be 90% if you're flexible about the problem you're pursuing. We chose an idea that allowed us to bring in at least a little money to lengthen our personal runway. Once we had a sustainable business, it was easier to approach investors and pivot slightly to the market dominating, high risk/high reward version of our idea.

Hope this helps! Happy to chat about this with anyone who's interested in doing the same! f at howdy.com


Be wary of advice you get and remember the money spigots were turned off this year and the funding environment today is wayyyyyyyy different than even a year ago.


I started my company in my late 30s, married with a kid. I'm sure everyone has a different strategy based on their circumstances, but this is what has worked for me:

1. Saved money through normal tech job and paid off obligations where possible, so expenses weren't too high and savings were good. So the risk of trying something on my own was manageable.

2. Left my tech job, but did consulting first for a few years. Easy to go back to a normal job if consulting doesn't work. Used savings to get through the initial period of figuring out how to do consulting. Really nice to have some kind of side income in this period - like teaching online courses or whatever fits into your skillset.

3. Built up money through consulting, but also built up contacts and partners in the target industry.

4. Pivoted from consulting over to the start-up in the same industry when the timing was right. Could have fallen back on consulting if the company failed. The nice part about consulting is you can split your time between paid work and your own work in whatever ratio you want, so you aren't ever jumping off a financial ledge.

It's not like this was some master plan. But it is how it worked out for me and we were thankfully relatively stable at each step.

As far as the company itself, my advice would be (1) Find really good partners you trust that are good at what you aren't good at. Being good at programming is maybe 20% of starting a tech company. (2) Don't up-end your life to start a solo side-hustle SaaS where you are convincing people to pay you $19.00 - find a real industry with real money to spend. Or alternately, keep a side hustle as a side job until it actually gets some traction.


I'm really curious, where did you find your consulting opportunities? And what did you precisely consult on?


> Are all startups at my age generally side hustles that become profitable enough to quit my day job?

They’re either side hustles that succeed enough to go full time, or they’re fully VC-funded so that you don’t have worry about paying the bills while you build it (VCs are explicit about that, they want their founders to pay themselves well enough to focus 110% on the startup and not on niggling distractions like bills and chores and whatnot).

There was a data point floating around a while back showing that most successful startups are actually done by people 40+ yrs old. They have connections in their industry and beyond, and deep domain expertise and knowledge of the problem they’re trying to solve, which gives them an edge. They’re just not in the news as much. Don’t recall where I saw it though, maybe here, maybe google.

You could start networking on Angel List (https://www.angellist.com/) and see what feedback you get on your idea. If you can build a very basic prototype that would help too.


33 year old CTO here with a fiancee and mortgage (no kids yet, but planning in the next year). When my cofounder and I started, we did it as a side project, nights and weekends, while making sure we were still working on other things to pay the bills. Once we got it to a point we could raise VC, we did and started taking salaries. We each make less than we were before, but not incredibly lower. We're in healthcare, so our primary income comes from health plans. Personally, I wouldn't have started this if it was a strictly B2C company. Our route to profitability is a lot more clear being B2B in my opinion, which helps both my stress and my partner's stress. She also has a decent job and we've always been relatively frugal, so we could probably get by on just her salary for a bit if things got really bad.

My cofounder previously started and failed at another startup, while taking bare minimum salary. It almost ruined his marriage and was terrible for his mental health. We're also just over a year into this, so we'll see if the higher salaries works out or not.


If you look at statistics of successful founders, the average age is like 45+. Why? Because you now have time to start a startup and you went through all the lessons in your 20s.

The answer is simple. You keep building on the side part time until it can become your full time thing. There are plenty of success stories from people in their 30s with families who made the transition (rare, but there's plenty).


I'm 44 and starting a few small startups; individual SaaS products that are small enough to be able to complete to market in a reasonable amount of time in between responsibilities. Unfortunately that's been a year in the making now. Fortunately it continues to progress. There's an old saying; "progress is better than perfection" and I feel it applies to this phase of life trying to accomplish this sort of thing.

The biggest thing for me was mitigating risk. I have a full time job that I'm keeping while doing this, and I've leveraged things like using Wyoming for an LLC to reduce fees and cost of having the business entity, and startup credits on cloud providers to kick off the business at minimal cost. If I fail, I probably won't be out much other than the time I've invested and about $1000. Worth the risk of another income stream, and a better bet than the casino.

Also want to add that my top and first priorities are my children and financial responsibilities. The startup comes second.


Why you choose Wyoming and not Nevada for example for your LLC?


I did this. Founded a bootstrapped startup with wife, kids, mortgage, that eventually and unexpectedly led to a life-changing exit.

The key is that I didn't jump into it full-time right away. I first transitioned from a full-time job to a successful freelancer/consultant where I continued to get paid for writing code, but controlled my time and commitments. At first, I did this full-time and out-earned my previous employment income. As the startup itch grew stronger, I started spending more (unpaid) time on the startup and less on clients. My income dropped significantly (to about 30-40% of peak earning - ouch!) and it was a big sacrifice and gamble. My wife had some part-time income and maternity leave income during these times, but nothing too crazy - I was always the major breadwinner.

My wife and I also were on the same page about living within or below our means. We always earned significantly more than we spent and could tolerate major reductions in earnings and still not dig into savings. That's not to say we earned a lot, but that we were smart & frugal with money and did not have $$$ lifestyle preferences.

Also helpful that I live in a country with universal healthcare. If my family's health insurance was tied to my job, I would never have become an entrepreneur as I am very risk-averse. Keep in mind, all that happened above was a gamble that I took. I got lucky with the outcome (through a combination of skill, luck, and timing). There are many scenarios that could have played out, some that would not lead to success where I would still be bitter to this day about the career and financial sacrifices I made. I took the gamble and won, but it could have easily gone the opposite way. What I do know is that my wife would have supported me in any scenario. How I myself would have handled the mental impacts of "failure", I'm glad that I don't have to find that out...


As I’ve become encumbered by life’s responsibilities, the main pivot I’ve made is to outsource a bunch of it. I spend money on this so may not be feasible for everyone but, I can project manage a small async remote team on top of everything else. Finding the team is a challenge but pulling back from the hands on technical stuff helps 1) minimize time away from home 2) I don’t end up with a hobby instead of a business and 3) I am forced to spend most of my time selling, which had always been my weakness (I’d build for the fun of it then have no plan for what to do to grow it).

I’m a night owl so I usually spend time after kids are in bed working on it. A lot of people say they find success waking earlier and getting in a couple hours before their job/family routine takes over. I think the main thing is to make a plan and talk to your spouse and ensure you’re aligned.


Yep, walked out of a tech lead role at a large corporate to start a new business with my wife, two weeks after the birth of our first child.

We wanted to work on wildlife/animal tracking and identification through technology. It was very hard, the limits are physical and geography and weather hate tech.

You can do projects for other people to fund it. We gave up on the animal tracking idea and pivoted and found a lot of the tech transplanted to other sectors.

You say you want to start your own company but also pursue a start-up. Those are very different models.

Do you want a business that you can work at or are you looking at fast growth and sell-out?

"The majority of businesses, on average, do not start turning a profit until as late as the third year. Some can take up to five"

I think you need to be clear on your goals first and then how to achieve them. Starting a company isn't a goal, it's a by-product.


As someone who started a company in my 30's and is considering another one in my 40's, my advice to you is that you just have to be more pragmatic. I have a wife, kids, mortgage, etc and I spend more time vetting the idea than I did in years past. I talk to more people about the idea to see if I'm onto something or if this is just an idea destined for failure. By spending a lot more time ensuring that the idea has legs I'm giving myself more data and also laying the groundwork if it is something worth pursuing. I would never quit my job unless I knew the startup could sustain my livelihood for at least one year.

So the short answer is that you can absolutely do this. It's about how you approach it and ensuring the people close to you are on board for the ride as well.


A few paths for you in my mind:

1. Bootstrap a side hustle

IMO starting a side hustle that becomes profitable enough to quit your day job is the best strategy here.

There are very few SaaS ideas that will produce $B returns in <10 years. They're all highly competitive with well-funded competitors.

However, there are easily thousands of SaaS ideas that will produce $10k/mo (with 90% margins) in the next 1-2 years. Take pretty much any existing SaaS product (eg. Segment, Zapier, Intercom, Jira, etc) and build a simpler version with nicer design for lower pricing, and you can get paying customers.

Once you're making $10k/mo (or even less) and growing you can probably quit your job and then that frees up a ton of time to invest in the existing business or a new business.

2. Buy someone's side hustle

Check our Microacquire. Tons of people are buying and selling SaaS companies on there.

If you have some money saved up, and some risk tolerance, you could consider buying a very small SaaS business (eg. $1k-2k/mo revenue) and growing it from there.

Even if this isn't an option for you, it's probably a good idea to check out Microacquire anyway to get inspiration for ideas for SaaS companies for #1.

3. Raise a pre-seed round

Try to find a VC firm who is willing to give you some money to spend time starting a company. This will be easier if you have a) a good background, b) a good co-founder, c) a good idea/big market and ideally an MVP.

That's kind of what the pre-seed round is all about. It gives VCs exposure to get into your company early at a great price, and it gives you a way to work on your idea while still making a salary.

4. Apply to be an entrepreneur in residence

A lot of VC firms have EIR positions where you basically get paid a salary while you're trying to decide what startup you want to start. The idea is that when you start a company you'll raise your first round from that VC firm.


You would be stupid if you quit in order to start something with a 90% failure rate. Don't be stupid.

Instead, figure out what business idea you can accomplish that would have a 10% failure rate -- a 90% chance of success.

While you're doing that, accumulate capital, so that you have at two years of complete living expenses in the bank.

When you have both of those things, you can discuss taking a year to do a startup, with a one year ramp. At the end of the year, you evaluate:

- is this close enough to success that you should definitely continue?

- is this almost ready, and you are no more than 3 months away from a go/no-go?

- is it time to end it, take a couple of months off to be with your family, and then have 10 months to look for a new job?


If read through nearly all comments but can’t see where you say « why » you want this?

To become a billionaire? To leave your job that makes you sick? To have a more exciting job?

I am mid-30s 2kids good, not crazy paying job (think 160-200k$ range TCO) and spend time with kids and travel 1-2x amazing trips a year with them. I decided not to give up that precious time and don’t regret it so far. But what I did is change companies until I could find that dynamic startup vibe with a good salary. I would even take the risk to go to a smaller company slightly less money but with shares/options. Up to you, but answer the « why » truly honest is my advice…


Because I have an idea I cant stop thinking about and I feel like ill regret it the rest of my life if I dont try it.


You really don't have to put you or your family at risk to have a profitable business that is a benefit to you and the people around you. You also don't have to work long hours or get no sleep to get there. There is no doubt that you probably won't be the next unicorn trying to go this path, but I honestly don't think those people are really as happy as everyone thinks they are. You can have a sustainable business that is profitable in several different ways that adds true value to the economy and to your customers and clients. You can even create a job or two that can provide a good opportunity down the line for someone else.

Take a look at some ideas that can be done as a solopreneur, parallel entrepreneur, or with a self sustaining small business that doesn't require a ton of capital or reoccurring expenses. Don't overcomplicate things or add a ton of stress to your life and build a product or service that you simply can put out there to see if anyone responds. It's important to note that not all startups have to be technology based or what everyone calls a "startup" here. You can be an urban farmer, or sell simple products that you, yourself have been wanting to find in the market. Talking to your local SBA office doesn't make you less of an entrepreneur than launching on HN either.

If you're unsure if an idea is worth it, put out a landing page to see if anyone cares about the idea or what you already have to offer. Spend a weekend or a few nights here and there and make something you're nearly ashamed of, then go try to sell it. You'll learn along the way what works and what doesn't. You'll also learn who you truly are and what you can do and handle. The only thing you need to know is whether or not people are buying what you're selling, and you can live with what it takes to make that happen.

I'm a huge fan of the advice that is contained in the 37 Signals / Basecamp books, so feel free to check those out to learn more about the themes I've suggested here in a better, more articulated package. There is also a book titled "The Parallel Entrepreneur" by Ryan Buckley that I've found useful too.

Good luck on whatever you find yourself working on!


Being older has its advantages. You have a lot more "common" sense, but not all older people do, some have kept emotional debt, trauma, various things that can hold them up from getting product market fit, leading teams and organizations, dealing with having a lot or not a lot of money, etc. If I recall, uncited, from my evening, later-in-life MBA program, the more successful startup founders/cofounders/etc are all in their late 30's and 40's. Weeds out the kids, you're serious. Staring at a seed round of VC's with life partners, spouses, kids, whatever you have in life that you're trying to maintain and help support, those are good things. VC that want to weed you out are definitely not worth it.

Leaving work to pursue a startup should only happen when you can prove well enough to VC's you're accreting revenues just barely worth investing in (to very worth investing in). If you're sane, I would wait until you can't move forward without some seed/VC and then look around for it- starting with people you know, and familiarize yourself with how funding/ownership/etc works.

You don't need to go through ycombinator, although its very worthwhile, you can just run a startup on the side or quit your job once its up and running.

If your startup is a unicorn, maybe wait a year before quitting your job, so the job market is ripping again when you fail :)


I've done exactly that in my early 30s. Bootstrapped, then raised a couple of rounds, couldn't raise again so went back to bootstrap mode, but ultimately failed. It was a rough period, but I survived to thrive as a senior in a FAANG nowadays. My marriage survived too and is better than ever.

Before I started my wife and I calculated by how much we can reduce our spending and figured that between her salary and our savings we could go on for about a year while maintaining an acceptable quality of life (for us) and not going into debt. While I was going through this her pay went up significantly (and unexpectedly), which allowed me to extend my personal runway. In the end, after ~four years, we were left with no savings at all and I had to take a job I didn't like because I had to start bringing money in. That was fine - I quit after a short while for a much better job. So the key was planning ahead financially and agreeing in advance on the limits: minimum standard of living we won't go below, and not going into debt. This proved very important in hindsight because it marked when I had to stop trying - I never wanted to give up, but had I continued, I would have jeopardized the most important things in life.

Another point about the marriage: my wife and I are together in this journey called life and support each other's hopes and dreams. I paid most of our bills while she was going through her PhD, then she did (plus we spent our savings) while I was doing the startup. Now I'm doing well, so she took a partial leave while she's pursuing hobbies and trying to figure out the next step in her career.


> So the question is: how do I continue my current standard of living for my family while working on a startup?

If it was known how to make money right away, everybody would start a start-up right away. But there are so many brilliant ideas, you just never know if they are going to work. Sure you can try, but the risk is there - as you said yourself.

If I were you, I would sit down with my wife, discuss pros and cons and also make clear why this matters so much to you. Hopefully you'll find a solution together!


You know everything is possible but a situation like this makes it a lot harder.

First off, young kids (<6) need parenting attention. If you want to go hardcore working side-projects and a fulltime job OR more than fulltime without income then that's going to push a lot of the work to your wife. Even if she's fine with it, usually your kids aren't. After 6 it gets easier.

Second, founders that have investment do get a salary so it's not impossible. However, the fundraising climate just collapsed and it is harder to fundraise today.

Third, it's not really necessary to build technology to fundraise though.. what's more important is to convince the investor that there is a genuine need for what you are building and that you have a team that can get it in the customers hands.

The best way to do that is with data from potential user interviews backed up by clickable prototypes of the product.

You don't actually have to quit your job to work with designers and conduct user research to figure out what you're thinking of building makes sense and it's trivially cheap to hire user testers online.

Talking to potential users and building out the prototypes is not a fulltime job. From there the insights alone should be enough to convince your wife, angels or accelerators to take a risk on you to build it. VC's will only come when you have graphs going up into the right.

So yes, keep it a side hustle but don't program anything... iterate on prototypes instead.


You have 3 main options:

1. Do it on the side, while working.

2. Save up and then go full time.

3. Borrow money and go full time.

None of them are easy or stress free.

I went for option 2. I worked like crazy and was making roughly my old income after a year or so, so I never burnt too far into my savings. There is a bit about my journey here:

https://successfulsoftware.net/2013/11/06/lifestyle-programm...


Also it helps if you live in a country with socialized healthcare.


Here's my take:

1) Salary: you should get some seed funding (500k / 1M), leave your job, and then immediately pay yourself a salary. Your seed investors should know about this.

2) Marriage: economic uncertainty will play a mayor role in this. Make sure you discuss your intentions with your wife before doing anyting. Try to understand what her biggest concern is. Try to address it. (e.g. show her you can easily get another corporate well-paying jobs if this doesn't work out; show her you have savings to not feel too anxious about this).

3) Do you want to start a company, or do you want to solve a problem? Important difference here. Meaning: do you dream of lots of money, glory, keynote at Techcrunch Disrupt, etc, or do you really feel an urgent need to solve a particular problem, and starting a company is simply the easiest way for you to scratch that itch?

4) Being in your 30s is not a negative. In my experience, it's actually a positive (you know more about life, work, tech, etc, and you still have a ton of energy to spend on it).

Edit: I should have added: I started two companies, I (still) have a wife with no kids, I also had a corporate job for a dozen years, I advise and advised many startups in general, and a few times in regards to an issue like this.


I think this will be an unpopular opinion to some; but I have a pretty firm belief that when you do the family thing and decide to have kids and the like; you’d better have established, or at least started / somewhat put in motion your goals as an individual.

As soon as you’ve crossed that line and had said kid, you have just made a conscious choice to significantly reduced your own time, finances; and flexibility available to chase after personal goals.

Before anyone immediately @‘s me; this is not always the case…but usually the people who can do both are 1) the exception to the rule, not the average; and/or 2) were relatively wealthy. maybe you can afford a caretaker for your child.

But that begs the question - so you had said kid, and want to give said kid the best life they can. Cool. We need people.

Probably adopting is the more sensible option; since there are tons of kids in awful, hopeless situations that can use your help, and we also have an overpopulation issue; but honestly, some people just want to have the experience of having kids. Okay, cool.

So…Does starting your own business right now, rather than investing into your kid’s development, really make sense?

By having a kid; did you not agree to set aside a lot of your personal time and finances to them?

Shouldn’t you do this sort of thing before you have a kid or after they move out? What if it takes off and your kid loses a parent being present because the career took over? :/

Asking from the perspective of a 33-year-old woman who sees having kids in your early 30’s; or, God forbid, your 20’s, as suicide of independence.


> I want to start my own company, but Im not sure how to pay my bills while looking for product-market-fit.

Not sure how much this applies in 2022, but in 2020 I started a company with a wife and one kid. Since then I've had another kid.

Here's how I did it.

- First, and most importantly, I didn't leave my previous job until I could draw a salary from my new company. This meant waiting until we raised a round of funding.

- Second, to raise a round of funding without a product, you need at least one of the following. 1.) some semblance of traction. For B2B this could be letters of intent from potential customers, a waitlist, etc. Anything showing that people actually want the thing. You would build this while employed elsewhere. 2.) previous success building and selling a startup.

- Third, to justify drawing a salary as a founder, you really need to be doing things that otherwise you'd hire people to do. This means working insane hours (80+ per week). I'm never really not working. Luckily I enjoy my work, and I still find time for my family. It just means I'm working randomly in 2-4 hour chunks pretty much 24 hours per day. If you're not ready to do this, or your family isn't, then don't start a startup.


I have started my startup at 30 when I was engaged (now married).

Every path is different but I think there are a couple of guidelines that I recommend: - Talk with your partner and set expectations from the beginning. Please do not romanticise the journey - it's damn hard and full of sacrifices. Others have suggested a deadline - I also did that but find it a bit unrealistic because you'll have excuses to continue devoting an unhealthy amount of time to your company. Be kind to your partner and acknowledge that they will take more load in family duties and you'll have less time to spend with them.

- Find a co-founder that is complementary to you and that you trust. Being a solo founder in your 30s with a family is super hardcore even if you already have found product market fit.

- Do not invest your own money. Finding an early champion of your project and your founder team that could be an angel investor to kickstart things is a must. The alternative is to do it as a side gig until you can reach some kind of Ramen profitability scenario - I'm not a big fan of this because you'll likely focus on revenue too early on.

Happy to chat about my experience if you think it'll be valuable (just DM)


>Are all startups at my age generally side hustles that become profitable enough to quit my day job?

Pretty much yes. There is nothing wrong with it. Don't leave your job and don't forget your responsibilities. I am too doing this between kids sleeps etc whenever I find half-a-hour free to work on my projects. Yes it's slow and overwhelming but still a progress. I hope as kids grow, there will be more free time available.


and its also the same at other ages with less encumbrances

they're all side hustles that become profitable enough to support, or its too big of a risk or too big of an opportunity cost, or there's worry about the "gap in your experience" etc, it doesn't matter what the "excuse" is, that's the responsible way


I built and sold my first startup in my 20s and building another in my 30s with family and mortgage - I suppose I'm qualified to answer this question

Short answer: yes, its possible

1. Find your niche and work 1-2 hours every day to create a strong pitch (a prototype and ideally a few early customers) - consistency is the key - EVERY DAY. Act with urgency here. 2. Raise a pre-seed round - this is when you quit your job. Yes, you are selling equity in your sweat. But there is no free lunch - you want to keep the living standards and also, stop working full-time for someone else - you need cash flow. There is a probability that you identify a really good problem and you grow customer base really quickly - that is very less likely in my opinion.

Once you have some capital, you'll have a larger canvas to paint - it changes the mindset to be faithful to people who trusted you with their money and also, brings in so much of focus.

There is the whole weekend hustler concept - I am not a big fan (I made more progress in 2 months full-time compared to what I could make in 2 years working on weekends)

What's the worst that could happen? Just do it.

Two mantras for you: Focus on intent; Always measure impact


I did this seven years ago as the sole provider for the family. We did not have any savings, so it turned out to be a very busy time for me. I had two years of overlap of the paying job and startup. I am opposed to the common advice of waiting until the children move out to pursue the dream of owning your own company. My father did this and bought a small startup that already had some traction when he was 55. He spent the next eight years working extremely hard under a lot of stress to come out in a good financial position, but his health worsened significantly from that. So, he fulfilled his startup dreams, but it was through witnessing this that I decided "the sooner the better" and pursued my dreams without waiting for the "right time." The two years of overlap I had with the job and startup was worth it. I have plenty of freedom now to spend time and take vacations with my family. I kept this post general because I do not think the details matter. As someone who has done exactly what you want to do, I say 'go for it. The sooner the better. Tomorrow is not guaranteed!'


Is there any non obvious pitfalls that I should know about? I mean theres the general pitfalls about starting a company that everyone on HN knows, but anything about starting a company in your 30s?


Depends on -

1. Your skills - Why? - How much you need to spend on Human resource? to reach PMF

2. Real dependancy on you of your family - Is your wife working/side passive income etc so you can ditch your job

3. Your Startup/Product Idea & how much time will it take to reach MVP and ramen profitable -

4. Your family's willingness to *sacrifice social pressure*. - Scarifying lifestyle/current standard of living is hard, more harder is to get rid of "What other people/social circle of your family will tell/think" of the new lifestyle,

5. Opportunity cost of doing job (or leaving job).

Most of people have hesitation of leaving job, so exact decision you only need to take (or not take).

Advice - Don't regret on whatever decision you take.

Let's say if you stick to job and same idea/product someone else become big big, No need to regret and vice versa.

Context about me 1. I left Software job after 7Yrs and bootstrapping since 10+ yr. Ups and Downs are part of life. COVID has made life bit worsen (as we are in daily commute!) 2. I am 35+ yo single, My parents don't depends on me, No-Unwanted-expense, from India


Talk. Get an idea. Talk to people that would use it. Don't build anything. Try to find two people that would hand you cash or better yet get cash now. IF, this works, and you are ready, hire two people on upwork to build it. IF, you get more customers, build out the features that helps you get more customers. If you do anything else than this, you are setup for relationship and financial doom.


The typical response (for example, I've seen Patio11 say this) is: don't make your life harder than necessary by including big life changes in your startup journey. Running a company is hard, do it the easy way.

That said, I did this with the love and support of my wife -- she wanted (and wants) to help me Live The Dream (tm). We got married, bought property, and had a kid while she worked full time and I started my company.

Even with her support it's been brutally difficult. My entire life runs on hard mode.

I recommend thinking less about maintaining a standard of living and more about acceptable tradeoffs.

A perfectly acceptable tradeoff to most people is to NOT start a company. If closing that door causes you grief, my condolences -- you'll have to do it the hard way too.

And: side hustles are, IMO, procrastination traps. They're a linear attempt to solve an exponential problem. Work will feel like progress but actual traction is hard, family life will always be a pleasant distraction, and investors will rarely take you seriously (it's literally the first question most investors ask newbies).


> it's literally the first question most investors ask newbies

What's the first question, "is this a side hustle"?


Yes, essentially: "are you full time?"


I feel compelled to provide a counter-point to all of the "you can't" comments here.

It's possible. I started a company with my co-founder three years ago. We both were mid-thirties with kids when we started. We've since went through YC, raised a seed-round, and the company has been growing ever since.

What worked for me:

- I saved up money and drew from that while we were getting the company off the ground. My co-founder and I went close to a year without a salary. Having a spouse that works also helps.

- Having a relatively low cost-of-living helped. It never felt like we were reducing our quality of life, although this was in the middle of the pandemic so we weren't able to go on vacations etc even if we wanted to.

Building a company is a lot of work, but that's true regardless if it you're married with children or not. I think parents have the advantage of being forced to be efficient with their time. It did require a lot of work after-hours coding to get things off the ground, but I probably would've been coding on something anyway.


Similar story here. I saved some money, reduced burn and had a girlfriend in work. I also bootstrapped in spare time.

It also worked out OK for me.

Not trying would have been soul destroying for me even if it was a bit of a measured gamble.


1. The first thing you do should be discussing this with your wife, not HN. If she's not on board with it, that's probably the first thing you're going to want to work on. If it doesn't seem like she's ever going to be on board, you have an uphill battle that you are going to lose in all likelihood.

2. Have you done market research? Needed startup capital? Have enough connections that in the case of failure you can just go back to a similar job in the industry?

> Im not sure how to pay my bills while looking for product-market-fit.

Yeah, you're going to want to test this before quitting your job. I think realistically if you can't get at least 2-3 paying customers for your product without quitting your day job, your chances of making it are pretty slim.

> Are all startups at my age generally side hustles that become profitable enough to quit my day job?

For someone like you, most likely yes. For someone who's a serial entrepreneur, probably not, because they can rely on their prior businesses to test out new ideas.


Very good question. I am literally in the same shoes as you OP and have been beating myself with confusion over the last 6 months or so. I am a new dad, but I have always loved buildings things and wanted to start a company as I have quite a few ideas, some of which I feel have good potential. In the pandemic we built a product and tried to start a company (as a side project), but it failed because of not being able to figure out monetization. While the experience part of it was invaluable to me, the enormous time I had spent juggling between both my full-time job and this side-project ended up affecting a lot of my family time as well. There were times where I hated my situation.

Now I am back being a passive, full-time employee that gets to spend some family time and not really getting into side-projects now because I know I can't - I do not have the time now - not with a kid. What I have come to terms with is that I need to arrange some financial safety for my family if I wanted to explore building companies. This is 100% possible. You can explore opportunities or get someone to join you as a co-founder and once you have funding, you can get paid a base salary that you and your family are comfortable with, along with an agreed-upon equity. In SF Bay Area, it's quite common for founder base salaries to be close to $180k or so, so it's more practical than you think.

My advice to you OP is that, if you have a kid, do not consider engaging in side-projects, but rather go all-in and pursue something as a full-time effort. You'll know if things are going north or south within 6 months. If no kids yet, you can make the side-project thing happen, but make sure to have cofounders and split the work. Focus on getting your MVP out the door real fast so you can acquire funding and make your side-project a full-time project. Considering these learnings, I am just holding off for now but I'll make a leap into entrepreneurship again.


My own advice as a 41 year old w/ two young kids who co-founded a SaaS biz at 36 while working a full-time job and didn't sacrifice income (but certainly quality of life). Your milage may vary.

- Don't start a company to start a company. You will be miserable. Find a space you like and start to explore it for fun (at first).

- DO NOT quit your day job. Nights and weekends to start. Have your partner pick up more kid/life duty if they is can. Quit when it hurts or when the path of your business lowers the risk sufficiently.

- Focus relentlessly on business model fit and real customer problems. B2B is fertile territory. Niche ignored industries with high painkiller need (vs vitamin) are fertile territory.

- Work with a team. Work with a team with no kids. Probably the most important part. :)

- Treat the work time a normal part of your life (like going camping or exercising)

- Ignore all hustle porn start-up mythology nonsense. Build the business around how you want to work that still achieves your goals.

- Its never easy, but its not impossible.


I started my first company in my early 30's. Here is what worked for me.

1. Found a business partner who bought into my vision for the company.

2. We BOTH sold our houses to get equity out for the business and also so we were not stuck with a large mortgage. We then rented less expensive homes.

3. Business partner stayed working at his job and he split his income between our families 50/50. We considered our value equal, so I worked the startup full-time and he worked his job full time. His income was not enough to cover all of our living expenses, but it certainly extended our runway.

4. We met every Saturday for about 4 hours to work together.

5. This lasted for 3 years until we finally make the company profitable.

6. Business partner then left his job and joined company full time.

FWIW, I always tried to start something on the side but never had enough time to fully bring it fruition. When you go "all-in" like we did, you have a lot more pressure to make it work (which is good). Most of my side projects were always kind of "half-alive".


There are all sorts of paths. Knowing nothing about you I would council holding your powder. Put time into the kids and partner and keep the side hustles to hobbies/participating as a chicken (see Chicken vs Pig fable) at most in the community. Much much more important on any timescale for both your and their happiness and health to keep attention focused on them.

It can be very frustrating/challenging to the part of you that wants to do the startup to do this, of course- that frustration in itself is valuable experience. The reason so many have successful startups in their 40s and 50s is not because they tried and failed at startups in their 30s. They didn't, and instead found ways to improve their impulse regulation, decision making, relationship management- and their financial standing. Speaking very much from personal experience, so much about new ventures becomes easier when equipped with strengths in these areas.

Manage the dopamine. Don't let it manage you.

Best wishes.


I did exactly this. I worked 2 hours per night after the kids went to bed on week nights, and for about 3 hours early on Saturday morning. It took about 10 years until I went full time, and I now been doing it full time for 10ish years. It’s possible, but you do have to be patient. In my case I was risk averse so I liked not giving up a good job.


My optimistic take as someone with zero experience in parenting, but lots of experience failing give myself breathing room and who is 30, is that you don't. I'm personally not that satisfied with my day to day work, but don't have any dependents or a mortgage or really any possessions or much responsibility, but I have hobbies and things I enjoy doing. A startup would probably grind me down and take away the bit of sustainable breathing room I need to be happy in other areas, all for what is probably a gamble.

The optimistic part is that you could theoretically work up to doing this when your kids are a bit older. Not necessarily full adults, but maybe.

For me personally I'd reduce the choice to "Would I rather have a good relationship with my family and self or sit in front of a computer even more, to possibly compromise everyone's well-being or come out with more money?" and that choice would be obvious.


Don't do this with kids under 5, they need your time and energy.


Sounds like you are in the US, so my answer won't be helpful for you, but in case some Europeans are reading the comments:

Check if your government can help you start your own business.

For instance in France, you can sign up for a program called "Aide à la création d'entreprise" [1], which gives you the rights to access like 1 year of your unemployment insurance compensation ("indemnisation d'assurance chômage"). If your income was 2 or 3 times above your spendings, it should be way enough to maintain your standard of living during 1 year, while working full time on your project. Then after this period, if you project didn't succeed, you can move on and look for a job. You basically take 0 risks.

[1] https://entreprendre.service-public.fr/vosdroits/N16153


Yes, been there, done that a number of times.

The first thing you have to do is make sure your finances are stable. That means make and follow a family budget, cut what is unnecessary, bank everything you can, and build 3-6 months of living expenses.

If you aren't willing or able do that as a family, you are not ready to go out on your own.

BUT during that time, you're not sitting still. You should be sketching out ideas, talking to prospective customers, getting feedback, and adjusting as you go. You may even be able to build UIs or potentially an MVP, do it. You're still in a VERY low risk stage.

If you aren't willing or able do that as an entrepreneur, you are not ready to go out on your own.

If you can accomplish BOTH of the above, you should have: a better conceived idea with real feedback, a list of prospective customers, a family on board with what you're doing, and the savings to give it a shot.

THEN you're ready.


Do you really have a significant idea or just frustrated with the monotony in the current job? Startups have a high failure rate. You will also have issues attracting funding in the current economy. Even is your wife didn’t know hiding this fact from her isn’t healthy for a good relationship.

If you do one just make sure you’ve got enough financial independence and most importantly an idea that folks think is significant. Are people willing to pay for what you plan to develop? How much time will that take away from family? Can you get funding through an accelerator? What sort of a financial hit are you going to take? Is your family onboard with it?

If your wife has a well paying job and is secure in her work she may be on onboard with limping on a single salary until you hit pmf (or get to a point where you understand there isn’t one).

In the end it’s about financial independence and time your family demands from you.


If you are accustomed to a 40-hour workweek, just skip the startup until your kids are grown. You likely won't be able to do that at a startup.

If you can push to 50-55 hours a week by e.g. working a few evenings a week, you may be able to make it work through a combination of contracting, outsourcing, and grit. (If you do not do a B2C startup. Those are harder!) There's no hard formula, but the basic idea is you can likely earn enough to survive through contracting for ~50% of the hours in a year. Relentlessly triage your MVP and launch quickly to paying customers. Then either reinvest the proceeds into labor in lower-cost countries to iterate on the product, or take a hit to your billable time to do so yourself.

If you get to $X,000 MRR, remember you can likely sell the business for a decent amount of money and start again from a more solid base.


I don't have experience doing so, but logically... don't quit your job and grind away for hours on a startup! You'll likely really regret it.

Some entrepreneurs start a side hustle, work on it in their spare time, and if it starts making good enough traction, then pour more into it. Have you considered this path?


You need to raise money and pay yourself a salary. It takes a village to make a successful company and going solo is very difficult.

Seed funding is still quite active although growth rounds are depressed. Hit up all your contacts, everyone you know, you might be surprised at who knows who. Worst case try crowd funding.


Just to add some inspiring notes to the thread — I've personally known several successful entrepreneurs who started tech companies while having kids (often 1+ kids).

Ranging from humble "providing okay level of life for the family" to ~1B valuation company (it's not 1password mentioned here, but comparably known company in its niche).

2 key insights I've got from those cases:

1) you'd better have a rock solid healthy relationships in your family

2) you have to become a god of time management and work prioritization

Most of them followed "classical" startup path of building a prototype while living on savings -> raising first money to survive death valley -> raising next rounds to scale found market fit.

Though I'm sure there are plenty of "side hustle solopreneurship" examples too.

TL;DR for me — it's doable? Yes. It's easy — hell no!


I think what you’re really asking is how do I pursue my dreams, of starting a business, without putting my family in a tough spot and especially how can I convince my wife who doesn’t believe in startups (risks etc) that it’s worth a try because it’s important to me!

I think you personally know the lifestyle will dramatically change - even if you take the money / income out of consideration by raising a lot of money from the jump. The time commitment alone will change things!

It’s an incredibly difficult and personal and even somewhat selfish decision that requires you to get the family onboard to somehow support you since it will effect everyone.

This is in fact your first sale task, that you must try and focus on.

—-

Here’s my experience-

About two decade ago I was in your exact position- but luckily for me I had a side project that was showing promise but nonetheless it was a risky and consequential decision to make with a young family.

My wife at the time (hint) didn’t believe in entrepreneurship or startups for that matter. She was raised that a corporate/stable job meant success (which it does in may respects), whereas I was raised a hustler and I knew from age of 9 that I would be an entrepreneur. We couldn’t be more different…

The options were - 1) hold on to a job forever and live a missable / depressed existence (not good for everyone) 2) Somehow convince her and family (yes in-laws included!!) that it was worth the risk or 3) pursue my life’s calling without approval anyhow and risk everything.

Obviously, options #2 is ideal but for me it ended being #3 (after almost 9 years of trying) - which effectively ended our marriage. Regardless of the choice , it would indeed doubly suck if business doesn’t make it - so keep that in mind (failure is not an option mindset)

I’m not saying that’s all the options you should consider… but since you asked for experiences I thought my experience might help put things in perspective for you.


Worked two jobs. I didn't want to take any financial risk whatsoever, or have my family feel that financial pressure just because of my desire to do something that would likely be more unstable.

Since we bootstrapped, I basically built the app on the subway ride there and back, and a few late nights. There were very few weekends because I didn't want to miss out on time with my young kids.

I will say though, that the company was basically dead before we were able to pivot our product and use it in pandemic response that provided a lifeline.

All in all, financially, I'm probably now breaking even on what I would've earned just doing hourly consulting for clients the last 5 years, vs starting the company.

But now we have a company with 12 people, a ton of great knowledge, and are on the path of growth. Hopefully this wasn't for naught!


>how do I continue my current standard of living for my family while working on a startup? You can't

You either have to save up for a year's worth of expenses and also downgrade the lifestyle and make sacrifices or convince a VC and raise a decent seed round but that too will come with conditions and you will probably not be able to pay yourself your market salary.

Entrepreneurship is hard. Very hard. Survivorship bias ensures that we only hear about successful ones where everything worked out. But as you already know, that happens in a tiny number of cases and that too after a lot of hardships.

Starting up something as a side hustle is the only viable option. You will have to put in after work hours and sacrifice some family time to fulfill your dream if you don't want to upset your marriage and lifestyle.


Every person is different and vary in time and concentration management.

If you have a single income stream with a lot of dependencies, it's extremely risky to even distract yourself with wishful startup ideas. The most useful advice would be to get your life/money/time in order first. The worst thing that could happen to a side project is when wife/kids/bills start complaining nonstop for attention!

Google has a 20% rule which could work for those who have managed to find clean time gaps in weekly schedule to work on side projects. But never commit full-time to an idea or half baked product until it matches most of your previous income with an upside potential that truly requires your dedication. ie. don't quit your job until you can fully pay yourself from the new business!


The short answer is that you can't.

The longer answer is that maintaining your current standard of living is not something you can do. You would need to make some sacrifices to get off the ground (roughly 18 months), even if you have a windfall of cash to take the time off you'd be sacrificing that windfall.

I have kids/wife/mortgages (plural), have started three companies, and worked in FAANG companies. I've never had a stellar exit but made some sustainable businesses. The cycle is basically feast and famine; 5 years at corporate job building up reserves and getting ideas, then 5 years of cutting back and getting a company off the ground. My wife doesn't really like the lean times, but she knows that is who I am (and dreams of big exits)


I was in the same situation when I left a comfortable job to do a startup. What sounds different is that it's unimaginable to me that anyone would do this without their spouse being onboard. My wife and I talked about this and prepped for months, saving money and going the bootstrap route. We pivoted along the way in different directions that we thought were the right way to go, but always kept our heads above water because we did it together. After crashing and burning in 2008, I went into consulting and have been doing fine. I'll probably do it again before long, using lessons learned from earlier mistakes. The thing is, we have no regrets of saying "What if" because we gave it our best shot.


Creating a startup is a huge risk taking endeavour, if there are factors in your life that might distract you from this like how you are going to pay mortgage or will I have time to be with my kids/wife, probably you shouldn't do it. Also, keep in mind that there are few possible outcomes to a startup - 1) it succeeds and you get rich, 2) it fails miserably and you are left with a huge debt that you might never be able to pay in a lifetime (this risk is real, I've seen it), 3) it fails, but you get away no debt, 4) it kind of succeeds, but it becomes a boring existential company that barely pays your bills and no one is interested in buying it.


I think you have a few options. One is the side hustle that slowly becomes profitable.

Another path is having a unique story that you can raise money on. A significantly sized problem that you are passionate about and have unique domain experience with. You can potentially acquire this unique experience via strategically picking where to work prior to starting the company. Such as taking a smaller salary specifically to get said experience.

The other path is just busting your ass working for someone else for awhile and building your war chest before going out on your own. Save up at least 1 year of living expenses.

For reference, I've done a blend of #1 and #3. Though in hindsight I wish I did more of #2. Having unique domain expertise gives you a competitive edge.


Effective wife selection is key here.


LC: very hard


I did good here, but it took me two tries ;)


Wow so many negative comments.

It is easy to start a startup in your 30s. In fact that is the only time you should start one. You finally have some life experiences to build a startup around.

By 30 you should have enough money saved to run for a year or two.

Your startup idea total addressable market should be clear. If it is close to a billion, go VC funded.

If it is in the 10s of millions to a few hundred, bootstrap.

Next, you have kids. You cannot faff around with company name, logo and such nonsense.

You need to focus on getting money in the door. So then where is your first customer? Hopefully with your 30 year of experience you have spotted someone already. Go to them and tell them that whatever they are looking for, your startup provides. Doesn't matter what they ask for, tell them yes it does that, the best in the industry. Take their money to book a spot as you are doing "revolving entries."

Do at least 5 of these. Tell them some nonsense about the price being a lot more but you are charging much less etc for them to be part of the existing cohort. This is important. Nobody wants to enter the train first. They want to be part of a journey where there are existing passengers.

Once you have money in your business account that is when you can start hiring someone to build a really scrappy version of your product. While all of this is happening make sure to always keep on getting new customers and getting money into the account. Business is about getting money into the business account. Never lose sight of that.

Now, you should have a huge dream about what your business can be. The larger the dream the better. If you can promise the moon and the stars and you have a total addressable market of about a $1 billion reach out to VCs, and ask for millions of dollars.

The larger amount you ask the more it'll seem to them that you have some special sauce. Once again make sure that you lie through your teeth because VCs don't understand anything and they're really easy to fool. Talk about changing the world and network meshes and AI and all those things. Get a good pitch deck designer.

Your only loyalty is to your customers and your problems space. Everybody else is a goose that needs to be squeezed. Once you reach your series B and Cs, losing is no longer an option. Make sure you sell secondaries and get at least $5 million in your personal bank account to derisk any future problems. From then on the world is your oyster.


Love your comment. However, remember that those ideas and practices for success were born in a demand market, and we’ve tipped into a market that is short on the supply chain side. The role of an entrepreneur is to gauge probabilities and be where it’s most needed in 3 years.


Universal needs will always be a demand market.


This is a great comment, thanks for posting


> Are all startups at my age generally side hustles that become profitable enough to quit my day job?

Kinda, successes will generally be:

1) Ascended side-hustle (soooooo much luck involved on this one),

2) You basically already have minimal FIRE money or better (for whatever reason—saved well while earning high, family is rich, whatever) and can afford to take a couple years without an employer with negligible risk to your financial stability, or

3) You have a high-earning spouse to cover the bills while you give your dream a try

1 is easily the hardest and least-likely to succeed—so much less time to put into it, and you're having to steal free and family time to do it rather than working during... work hours.

(see also: getting started with a career in the arts, especially 2 and 3)


"Are all startups at my age generally side hustles that become profitable enough to quit my day job?"

Mostly that is the way BUT not the only way. Have you saved any money to take this risk ? Can you work for say 12-18 months and not worry about paying bills if you quit your high paying job ? If yes, then by all means you should consider it. If you don't have anything saved and you don't live below your means, tough luck. You have to give up somewhere if this is important to you.

Another option is to use your money and buy a small project/business that has some cashflow coming in already. This may not be a hockey stick high growth startup but may be you don't need/want that ?


Kinda in a similar position myself. Would love to create something of my own but the house and car won't pay themselves.

I imagine it could be done but you'd have to cut down your expenses to a minimum which in my opinion comes with too much of an opportunity cost. By which I mean missing out on experiences and fun things with the children. In 10 years time they'll be busy with friends or video games. At that point I could consider it again.

If I was really determined to make it work I'd aim towards contracting in a field you have experience in. If you have enough success with that you should hopefully be able to pay the bills from that and squeeze in work on your own thing between paid gigs.


If you want to maintain your current standard of living and start a business you need customers, investors, or savings. If you want to start any business, startup or lawncare and all points in between, you need customers, investors or savings.

So start by solving that problem.

P.S. the "90% of startups fail" is inaccurate and moronic. It gives no context on the type of business or the outcome. Starting a 1 million dollar / year lifestyle business is incredibly simple (not easy, but simple). Starting a fifty billion dollar pharma company is incredible difficult. Anyone saying "well I want to start the latter, not the former!" has never had a 1 million / year lifestyle business.


Any pointers on how it's simple to start a lifestyle company? I've always been venture backed so breaking into a market for a lifestyle business seems just as hard to me


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