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Ask HN: How to know if you should stop doing startups?
39 points by throwaway127890 2 days ago | hide | past | favorite | 41 comments
I've been doing the startup thing for a decade now. Founded my first company and we raised a few million and had an OK exit - that is to say, I can scrape by without working too hard for the rest of my life, but this would be a mediocre result and career, at best.

So it's been a few years since then and I've been trying to start new things. Nothing seems to stick -- there's no excitement from other people, and I can't seem to stay focused on an idea for more than a few months.

The hype around startups now is also a drag, tbh... It was fun when it was geeky nerds building stuff, and now it's like everyone and their mother is a marketing machine. On top of that, I can't help but wonder if the world really needs another Canva or Airtable or whatever... Yet this is where everyone seems to want to be.

So... I spend more time debating ideas and giving up on them than I do actually building anything.

So now I'm wondering: should I just get a job? Part of my knows I will regret doing that but I also feel like I'm getting stale and useless.

Anyone else been in this situation? How'd you get out of it?

> I can't help but wonder if the world really needs another Canva or Airtable or whatever

it probably doesn't and a business venture is a means to an end. I always thought the idea of 'doing startups' is kind of silly. Business as a recreational lifestyle produces mediocre entrepreneurship and probably stuff nobody needs.

there's nothing wrong with getting a job somewhere and working on something interesting that needs fixing, there's enough of it to go around.

Yes, I agree on business not being a recreational pursuit. I definitely am missing the drive now.

I also agree that there’s nothing wrong with getting a job. I think it’s more about coming to terms with not being good at entrepreneurship.

You are clearly modestly competent at entrepreneurship and to the point where it's worth pursuing because of the high opportunity cost. I think it would be wise to take some time as a salaried employee while identifying and correcting the gaps in your skillset.

Thank you, both for the feedback and kind words.

I'd suggest to get a job in a field you most passionate about. The role doesn't matter. Work there for 3-6 month to identify the problem that industry has. Then leave and build a company that solves it.

Thank you! That’s a great idea; I like not closing the door on startups so this is awesome.

Get curious find something you're actually interested in. The Airtable people, bless them, were probably really curious about organizing data. But that's not you, ok.....in 50 years, what will be obvious in retrospect but you're curious about today? Crypto, VR, biotech, Siri, satellites, cars, solar panels, something else? You decide!

You know, I'd love to tell you, but this is the challenge. I don't know if any of these excite me -- not sure if it's burnout or just pressure or something else.

> I don't know if any of these excite me -- not sure if it's burnout or just pressure or something else.

Well, what does excite you?

Keep in mind that excite can be almost any strong emotion, including things like anger, fear, or frustration, not just "it would be really cool if..."

Motivation can come from anything that gets your juices flowing, from "I can't believe they're actually charging money for this shit" to "dammit, why won't my gizmo talk to my gadget" or "oh no, $PROBLEM affecting $MY_COMMUNITY is terrible, what can I do", etc.

It's totally fine if they don't those are just examples. And "you decide" was the wrong term. Your curiosity itself takes the wheel, you're along for the ride really. Instead of bitcoin maybe your curiosity will choose sock design, cooking, or collecting leaves. Just know that eventually curiosity will come. And yeah, burnout is real, good stuff written about it.

If you have 'solved' the money problem for your personal life and seems looking for 'purpose' and 'positive feeling reward' have you considered giving time to charity/community (specificaly 'local' ones near you live) ?

I think a common lacking in those (smale scale) organisations is sometime basic event/communication/money management, with often more enthousiasm than skills.

I don't know on the USA (I assume your from here) but hackerspaces and derivatives can allow you to keep in touch with the startup world while helping a lot of enthousiast people and being emotionaly rewarded.

Of course that mean taking a standard job to live. In Europe (dont know for USA) it can even help you land a real part time job after some time.

You should stop once your aspiration to continue is eclipsed by burnout. In other words, you've reached your final plateau, and are so stifled that you must descend.

Note that I am not saying that burnout alone should be cause for quits, far from it, but that you've reached a level of burnout where you are not assimilating what you've learned up to the point of that burnout to help you move past it.

Burnout is always telling us something, that there needs to be some change in our processes.

what is it that you like? building stuff? talking to people? money? power? I asked these questions when i was semi retired and what i found out is that i like building stuff. So now i build stuff, it doesn't matter to me if it is another canva, if it gets me some money i am happy, if i release it for free and someone uses it, i am happy. If no one uses it i am still...happy because i enjoyed the journey. Concentrate on journey and not the outcome.

It sounds to me as if you need gift yourself some mental time off. You're clearly an entrepreneur, so I'd caution against getting a job, but you've not had a follow up hit and may have lost a little confidence in yourself and can't see the joy in trying to build something new.

You're in a fortunate position financially so I suggest you use that freedom to detach and replenish. Ask yourself, if I allow myself to do absolutely anything (or nothing) for the next 6 months what would it be? That's a pretty exciting thought right? Not only will you break the cycle of intellectualizing your situation, the process of self-permission will open up new ways of getting out of these ruts in the future.

If it were me, I'd switch off every device and read the Guardian's 100 best novels of all time.

I would read philosophy on the subject of sublimation. There are many profound writings and writers that have explored the idea. Nietzsche is one, Emerson another. I expect you will discover an agon that challenges your present value system, and this will become curiously interesting. Lead a hidden life with a private good in mind that runs in parallel to the life that is expected of you. But perhaps you are already well versed in these matters.

Definitely not well-versed in this. Reading the Wikipedia article now, but if you have specific references you'd recommend, I'll check them out. Thank you!

This might do. Keep in mind that, although Emerson was religious, it is not at all a prerequisite for the reader of Emerson to believe as Emerson believed.

"There is a third silent party to all our bargains. The nature and soul of things takes on itself the guaranty of the fulfilment of every contract, so that honest service cannot come to loss. If you serve an ungrateful master, serve him the more. Put God in your debt. Every stroke shall be repaid. The longer the payment is withholden, the better for you; for compound interest on compound interest is the rate and usage of this exchequer."

from https://emersoncentral.com/texts/essays-first-series/compens...

Take a job if that feels like the right next step. As someone suggested join an earlier stage startup that has cracked product-market-fit, and you have an opportunity to create a strong relationship with the founders. You may start by leading engineering at such a company based on your experience here, that can transform into leading engineering+product into engineering+product+technical sales into COO etc. I know friends who have gone through similar journeys, and have achieved immense success both financially and spiritually by joining a caravan that is already on the road.

"Doing Startups" is not a thing. A startup should just be an outcome of something that you enjoy doing. If you are frustrated with the process, stop doing it. You seem to be in a very privileged position in which you have financial freedom. Don't restrict yourself by following what others define as "mediocre result and career". Do what you love and you'll see it will turn into a success.

I’d recommend getting a job or at least starting the process. As you go through the motions you’ll be deciding if it’s something you actually want to do or if you want to keep pushing.

Thanks! I think this thread is definitely convincing me to at least search and explore employment opportunities.

Perhaps you should find someone that does have a good idea that you and others are excited about.

Yes! I am definitely looking for people to start things with too, if that's what you mean.

Do you have an email address? You can make a new account on proton. Will send an initial message there.

What do you care about? Which problems would you most like to see solved? By whose measure is "not having to work hard for the rest of your life" a mediocre result?

Your last question is a good one and I do want to say that I count my blessings regularly!

What scares me about my current position is that I definitely see myself atrophying. I am at a local maximum at best, and there are so many other hills and mountains to climb.

You can also use this as an opportunity to start over/ try something new.

Consider getting in to hardware. Far more interesting.

Every time, I’ve seen someone ask about doing a hardware startup here on HN the general advice is do not do it, almost like anyone wanting to do a PhD.

Currently at a hardware-inclusive startup: most certainly is a different beast and requires a whole host of other engineering skill sets.. plus you are at the mercy of supply chains, long lead times in iteration, slimmer margins…. Time to market is immensely slow by comparison to a SaaS product and if you don’t get it right, there’s no remote hotfix to a bug at the hw level.. you need cash to burn, and time to burn it

HN is a bit of an echo-chamber for SF/SaaS/ML/FAANG.

Are there specific subsets of the hardware space you recommend exploring?

Not really, it's all pretty much ripe for software-based redefinition. Supply chain, electronics, production, design, assembly, inventory, testing... standard efficiency levels are low and trends toward distributed manufacturing, JIT, redundant supply chains and high mix / low volume mean software based process definition and management become critical and the days of the old ways are numbered.

have you considered joining an early stage startup?

I am definitely considering this -- when I say 'job' I often think I'd be better suited for a smaller company because I'm a pretty big generalist. I can sell technical stuff, I can write code, I can manage people, but I am by no means an expert on any of these things.

I guess you'd recommend early stage startups as the opportunity to explore?


Thanks for the response + help. :)

Given that description, you might want to consider consulting or technical sales/architecture as well. I did it for years in the services arm of a big tech company. The bureaucracy is going to be a lot higher, but a broad skill set with “softer “ skills is valued and rewarded that domain, at least once you are in the door.

Oooh, this is interesting. I started my career as a consultant before doing startups. It's one area I've debated quite a bit mainly because it doesn't focus on product or sales (unless you're a partner, and even then, "sales" != "client development"). This is helping me think of criteria, so thank you.

Re: technical sales, this is actually a really good idea as it fits my social + technical interests. Curious if you've done this? Curious about your experience.

Not as a profession, but I worked with our sale/pre-sales side people a fair amount. I can say, generally, they liked the pace, challenge, compensation, and that they constantly got to do new things. Quota was complained about, as was paperwork, tooling, and internal politics/bureaucratic in fighting. Travel was common.

The titles at my company (Microsoft) are generally some sort of “architect” or “specialist” for straight up technical pre sales / sales or “account manager” for a more straight business and relationship side of the house.

lol, im a bit similar. I can code pretty well, but i like being able to jump around and do different things, talk to stake holders etc.

I think you might be able to easily get a job at an early stage startup, and have a pretty deep impact with how things are done.

Happy to help

if you are US based, and know the MERN stack, email me(profile). A startup i work with is searching for a CTO, its an early stage. in case you are interested

Thank you for the kind offer! I really appreciate that, though I am not a MERN stack expert + wouldn't want to waste the startup's time. I will reach out if this changes.

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