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Ask HN: Founders, what's your lifestyle like?
116 points by dereking on Feb 21, 2015 | hide | past | web | favorite | 94 comments

Mostly free time. Probably not much different than most retirees with money in the bank.

I always wanted independence. I never wanted employees. SaaS is a wonderful business model for that. It took 10 years and a dozen ideas to find 2 businesses I could run on my own, be low-touch enough that I'd not have to be hands-on with every customer, and pay enough to be a viable alternative to employment. Most of my web app ideas didn't go anywhere, nothing happened overnight, but eventually I had the right mix of learned skills, experience, and luck to do something right.

I spent 10 years living like a broke college student. I was a broke college student in the beginning, but I didn't move past the one-bedroom apartments and cheap home cooked dinners until I had some solid business and a good runway in the bank. I was never a risk taker.

Now I pay myself a $30K/month salary. I saved enough to buy a house, rather than mortgage a house. Met an awesome girl and moved her, and her pets, in with me. She's always hated the work she originally trained for, and has gone back to school for a career she's passionate about -- working with large animals. I've been working every other day, a few hours at a time, recently. I work more in the summers than the winters, just because I prefer working outside in my sunroom with the fresh air, but it's not heated. We spend most of our time together, taking day trips, eating out, visiting friends, and don't worry much about money.

This is really awesome, thanks for posting it! If you don't mind me asking, have the 2 businesses you have active always been low touch or is that largely a factor of their success? Eg at this point it seems you could let someone demanding loads of support just opt out and go elsewhere - but did you initially have to be significantly more hands on?

$30k a month? - Incredible

I read it as per year. I went back and double checked. Per month it is!

How many relationships did you have before you found someone that was compatible with the lifestyle you had built up? I found it really hard to maintain a long-distance relationship while a CS undergrad, and I'm curious how that side of your life worked out.

I find it interesting that you found it harder to maintain a long-distance while an undergrad, especially because from personal experience, it would be easier that way (IMO of course).

I'm also an undergrad and what I largely find is that it would be easier to be in an LDR with regards to your workload because you don't have as many daily "commitments" if you want to call them that, i.e. you're not trying to balance your projects with going out to eat a few times a week. The expectation is that you're not going to be seeing each other all the time, so theoretically you would have more time to spend on your work. I'd be interested to hear why you've found the opposite to be true (aside from CS, I think my true passion is relationships ;-) ). Now, give me a non-LDR relationship any day and I'll find a way to make time.

On further thought, you're right that a non-LDR is harder in terms of balancing on the day-to-day and that's part of what made me comfortable with remaining in it for so long despite the discomfort of being apart so much - I could more easily do what I needed to, but consider this: frequently I felt guilty for not Skyping for a little longer, or having longer phone calls, or always keeping in touch with text messages, iMessages, FB, Couple.me, etc... and it felt really asphyxiating. I constantly worried I wasn't doing enough, and I frequently felt guilted with respect to "not putting enough into the relationship" which is probably my fault for not establishing boundaries early on. When we saw each other on bi-monthly trips, I still had to get work done (CS, other classes) and I was constantly guilted into "you should've done it before the trip!"

Originally the plan was for me to go down to go to her after I graduated (to Florida) but I got an interview for an internship in NYC, which I performed well in, which was converted into my receiving a full-time offer in Manhattan. I accepted since it is at a firm I wanted to work for since I was in high school. Literally my dream job. She was open to the idea of moving up with me but she enrolled in an academic program that would have added another 2 years of an LDR after already 1.5 years. She was perpetually sad over the summer when I interned in NYC (she was living with me for a month) because we couldn't spend time together even though my working hours were quite good compared to my friends in Seattle and Palo Alto, and I realized my ambitions were met with ambiguity and a slow-growing resentment.

The pushing back of an "end date" for longer and longer eventually led to my feeling that overall it would be healthier to end it, additionally considering the changes that happened in our lives over the course of the relationship. That being said our goals had also diverged significantly.

I knew what was important to me so I decided that it was best to move on since our long-term goals were no longer aligned, but it was an incredible experience that I'm lucky to have had. Not everyone gets to meet someone that, for a time, they connect with so well. I look at it as a learning experience that has made me a better person which I'm told is the best perspective to have.

How did you go about gathering customers? Also, what are the 3 main lessons you learned from the other failed startups?

These lessons won't apply to 99% of startups, but they're what I've learned work for me:

Sell to small businesses. Not consumers (too hard to convince them to spend money), not enterprise (too much work for me; I hate sales).

Make something that will earn the customer money, or save them money. If it can earn or save them more than you charge, it's easy to sell, and they'll be happy to pay for it. That covers a surprisingly large number of potential business ideas any developer could create on their own. One of my first successful ones was just a WordPress plugin to add Amazon-style review/rating capabilities to any site, before anyone else had commoditized that. It saved money (versus hiring a developer) and earned money (most of the customers were affiliate marketers building product review/comparison sites, and their sites earned them more commissions when they had good-looking user reviews on the product pages). I made $250K from that plugin before selling the business on Flippa.

Make it easy to get that value out of your product as soon as possible. I do a free trial. I expect users to at least "get" how they can earn or save money using the product before that trial's over. The most important aspect to that is to get onboarding right: good lifecycle e-mails, a good first-login experience, and walkthroughs or something else that guides new users through the product. That's also what minimizes the customer service load.

If you have a good product, the customers will come. Well, maybe you'll need some AdWords ads to get the first ones; that's what I did. Now there's 2-3 signups a day that are just referrals from existing customers. It's enough to stay ahead of subscription churn.

Oh, and pricing is important. I doubled W3Counter's MRR by changing the plans around and adding annual billing. Improvely's MRR grows as the customers' businesses grow since pricing is tied to the level of traffic their sites get. The value they get out of the product grows with that too, so everyone's growing together and happy about it.

Out of curiosity, and I don't mean this at all in a negative way: Why do people pay for W3Counter when Google Analytics is free and seemingly a lot more powerful? Do people really find GA that intimidating?

W3Counter's more fun. It's bright, colorful, nothing's buried multiple menus deep. Whole classrooms sign up for it every year while learning to build webpages. It gives your site a hit counter so you can watch the visit count go up every time someone new checks out your site. You can "spy" on those new visitors, seeing where they came from, watch them move page-to-page, stuff GA doesn't do with its aggregate-level batch-updated reporting. New site owners love that stuff. I also first created it years before Google bought Urchin and made GA.

Unless I'm misunderstanding, I am fairly certain GA does everything you just describe. They have a real-time menu option and I can see my users going from page to page. I can see the number of people on my website right now (21).

I guess the bottom line is your platform is much more approachable and easier to understand. Thanks for the response.

Following individual users around (something W3Counter lets you do) is fundamentally different than a real-time aggregate dashboard of the same users (something both sites have). A dashboard is interesting to a business. Friend-watching is interesting to ordinary people. "Oh, I just got a new visitor from Facebook in Camden. I have a friend in Camden, that's probably Jessica! I wonder what she's looking at? Oh, she just opened the guestbook page and has started writing something!" is fun for someone running their first blog.

Thanks for the responses, this sounds cheesy but you're an inspiration for the goals that I'm working towards right now (making SaaS products for small businesses). I will start working on it full time in about 4 months (with ~2 years of living expenses saved up). You give me hope that it's not just a pipe dream :)

Thanks a lot man! I'm currently in the brainstorming phase for my dream startup/business and your advice came at the right moment, especially the comment about targeting small businesses!

Hey Dan,

Got a ton of value out of your post. Just wondering one thing, how much of Improvely did you build before you started running ads?

Thanks buddy great advice!

I have a new saas product and I'm trying to figure out whether to sell to SMB or larger. Do you acquire customers via ads? What's your cost per acquisition? What's your CLV? I'm doing consumer stuff right now and the low CLV is driving me nuts because it gives me zero ad budget.

That's really awesome to hear. Thanks for sharing. I'm curious, how is your tax structure set up? Are you an LLC, C-corp, etc...?

Your Zendesk link on the Awio site does not work.

Throw away for obvious reasons.

My partner kidnapped my children to different country.Three week granparent visit for "trial" will be soon two years. I dont have much options, so I followed. Now I am at country with zero friends and unknown language. I can not order in shop, my children just started talking in foreign language and I need translator.

This brings lot of stress, but it is also (sort of) distraction free. There is basically a truce with my partner. I am lucky to work from home and spend lot of time with my children.

I work about 2 hours/day to pay our bills. For another 5 hours I work on my "PROJECT". Very niche programming library in good field. Next year it will be ready, I am planning to divorce and scale up the business.

I am 10x programmer in very narrow field, all this reduces my productivity to third, so still doable.

Which country is it? Maybe one of us can help with daily problems (language, communication etc.) I'm in Turkey.


If you need help with spanish or are in Spain just drop me a line!

Sorry to hear that man, I hope things will pickup for you mate.

How do you know you are 10x programmer? ;)

Bad: I work 10 hours a day, 6 days a week. Good: On something I like to do.

Bad: Have to keep most customers happy. Good: Can tell that one customer who is genuinely being an asshat, to go fuck himself.

that one customer who is genuinely being an asshat

Tarsnap sometimes has "problem customers", but I have yet to see one who is trying to be a problem. It's not really the customer's fault if they don't know how to install a compiler, think that uploading 100 GB over a 512 kbps cable modem will only take a few hours, or can't figure out how to enter a valid tar command (cue xkcd).

I do my best to help such customers, which usually involves refunding their money and pointing them in the direction of dropbox, spideroak, or duplicity.

"Can tell that one customer who is genuinely being an asshat, to go fuck himself."

Working in customer support I can tell that you Sir, are living the dream.

So it sounds like every corporate job I'be ever had. Except more upside. The downside is you might have to get a corporate job if you fail.

Although I would love to be able to fire a few customers but I'm sure my benefits are probably better if you are early stage. I actually had better healthcare before acquisition. Which suprised me.

How big is your team?

Three people full time (me and two others), around a dozen collaborating while they do other stuff.

That's about as big as I can manage it, so that works out. Not looking to expand at the moment. Some people may work for us full time when they wrap up their day job.

Exactly right.

I'm in the 2-person weeks-away-from-launch phase of a startup, and it can be fairly hectic. There are so many little things to do (make email templates, fix this bug, make that feature), that I use trello to keep track of a weekly plan. I split things up into a weekly to-do/doing/done and only keep on the board what I think I can accomplish throughout the week (and revisit it daily). It helps a lot with lining up tasks in the order I need to do them in.

The lifestyle part of it is that 7 days out of the week, I wake up whenever my body wakes up and pretty much roll over to the computer desk and start working. I'm married (with no children), and although it took her a bit to really buy in on giving me uninterrupted development time, I finally have that for most of the day. I pretty much do this until 9-10pm, and then my wife and I catch up on TV shows or watch a movie or two.

There are, of course, minor distractions throughout the day like reading HN, or playing a few iphone games. In order to combat that, I hold off on doing anything like that until I hit micro milestones on my current task.

As far as money goes, I left my full-time job in order to work on this idea, so there's absolutely no income until I start generating it from customers. I'm borrowing against my house to pay the bills, but that's how much I really believe in what I'm working on, and I've intentionally forced myself into this position because it makes me prioritize everything as if my life depended on it (which it does).

Basically I work all the time but I really enjoy it. Company is at the 10 person/just started shipping phase and we are busy trying to change it from a "just get something working" to "organized chaos for growth" company.

What makes it hard is I am a single parent; fortunately he's old enough that he can get to and from school on his own. But it's tremendously tough to give him the time he needs. Luckily if I manage that it gives me the "off time" I need too. Which is great since I've abandoned, for a time, all the other stuff I used to like to do (camping, playing tennis, reading, biking, writing code for fun...). I sit with him while he's doing homework and can answer mail and do other interruptible tasks and still talk to him about his homework, help him write something etc.

I figure there are another couple of years in this nozzle and then the pressure will drop. But at the same time: I wake up in the morning and that's when I want to read HN or my RSS feed simply because the rest of the time I'm having waay too much fun working.

Constant running 10 hours a day 7 days a week for 1.5 to two years until we had the first real product launch and enough market traction to hire a bigger team. Then shifted back to 5 days + some reading etc on Sunday morning.

Now (1.5 year later) busy with international roll out (we're in Europe) so working a few 12 hour days + flying when abroad, then taking regular "no phone, no email, just girlfriend" weekends to relax and make up for not seeing her for a few days a week.

The reality is that hours don't mean that much if you get energy from your work instead of spending energy on it like I would when I was working in a "normal" job. But even then I feel it is important to keep time for sports and enough focused "offline" time with your boy/girlfriend or kids. Otherwise it becomes unhealthy over the long term even though you feel a lot of accomplishment / enthusiasm.

All in all, I love it.

I am living off what I made with my last startup and work fulltime on my new startup. Most days I jump out of the bed and start working 7am in the morning. And often I am still working at midnight.

The one thing that bugs me: I decided to not travel until my current venture is making 5 figures per month. I miss traveling. I am looking forward to the time when money is pouring in again and I can take a one way flight to wherever I like. And stay in some comfortable airbnb apartment or upper class hotel room for as long as I like. That's what I was doing when my last startup was flourishing. Now that I am living off my savings it would feel somehow wrong to do that.

I can relate to bionic's description "living in a dimension outside of space, time, matter, mass and gravity". It's all my own rules. My own goals. My own story that nobody around me can relate to.

Are you working alone?

How long (from the start) do you think it will take until you do 5 figures per month?

You're telling me you even get to sleep in?

What does that mean?

It was just a poor joke about 7am being considered early in the bay. Mostly because I loath my 5am wakups for my corporate job. Sorry.

Throwaway due to paranoia about visa status [1].

We both applied to YC summer 2014, were turned down. As the "business" founder (although I make a few commits every week as well) I sought clients out, and we found a medium sized retailer who had some backend issues almost by accident. We became their DBA for 100k USD a year each [2] (something we have a collective decade experience in) plus a work permit so we could live there, working half time. We spend the other half working on our idea, which turned out to be a good thing because the two AI problems core to our success took a bit longer than planned to be solved (our 40+ competitors all use humans).

I save around 50-60% of my salary, fly to exotic countries at least monthly (typing this from Australia, going to Japan in 3 weeks) without having to take leave, I live in a nice flat in the centre of town (next to the President's house) in a first world city with nice weather, I never have to wear a suit, and best of all, we don't answer to anybody because the client treats us as expert consultants, not an employee (there is a significant difference!) and we don't have investors and won't need any. The chilled out nature of an easy DBA job with good (enough) money means we can do research properly and build a good quality product. I have to say, whilst I understand PG's dislike of bootstrapping vs taking investor money (and it makes sense when your idea is new and first mover advantage is important)... well, it's a really nice way to start up I think. YMMV. I think financial freedom, and freedom from irrational management techniques designed to control you and not just your output, is by far the highest quality of life improvement I ever made.

[1] There is some fuzziness here about the terms of the visa from the gov. Technically, you're supposed to work for only one employer; that is, you can't just work part time and build your own business with the other half, nor have a split company visa. In practice, a lot of people do it and the government is very pro-entrepreneurship; but I'm not leaving a paper trail just in case.

[2] Cost of living and taxes are quite low here, so in SF terms that's probably equivalent to 200k.

(Solo-founder in the middle of a last pre-launch crunch): all the emotions I had (excitement, fear, doubt, fun, confusion) seem to have been dialled out to white noise and I find myself in a moment of almost zen like tranquillity. I know what I need to do and am just doing it. I get up, go to my computer, work and go to bed. I do this 6 days a week and spend day 7 re-assuring my girlfriend she's not in love with a robot.

It's not sustainable, the end's in sight but perversely it's quite liberating. I feel like I've finally achieved complete internal acceptance of what I'm doing.

Sounds like you are approaching burnout my friend. Beware the unsustainability of this approach. Launch is simply the start of a long journey. If the launch fails to get traction, will you have the energy to continue?

We work 6 days a week with sabbath off No fixed hours but try and keep sleep, exercise and weekly update meetings regular. As most people say we either work "all the time" or "not at all". I like it no matter how hard. My partner suffers because the uncertainty eats at him a bit. We're at that stage where people think we are a) nuts to leave high paying jobs or b) deluded that we can actually do this ourselves... So the family/social support is kind of 50/50 which impacts lifestyle a lot. Example: we get free rent at home and our friends have preordered because I think they worry for us and want it to work. I noticed I have less tolerance/ time for mates other than my closest friends who know me best and accept that sometimes the only time to chat is via Skype while waiting at an airport.

Overall, and I'm embarrassed to say this but this is the best lifestyle I could ever imagine. To be successful while living free like this feels almost like its unfairly good, though I'm not sure yet if I'll ever experience that.

We try and do volunteer stuff as when you're a founder it's so easy to be self centred. This helps us look outward and be less wingy bitches when the shit hits the fan.

I sleep in, wake up, and work till about 7pm depending on time zones I am in (right now most of my calls are 3pm to 7pm since I am in Europe for a few months). I've scaled the late nights back a bit since I got married, but occasionally I'll work through midnight, and occasionally a day on the weekend. I love my work so it takes a lot of work to make sure the balance is there. Before I got married I worked a much more flexible schedule, I worked when I felt like it, and when I didn't I didn't. I usually ended up working around 50 to 60 hours a week.

I never minded the stress prior to this last year, generally if I get burned out I take a vacation and I'm good after 10 days on the beach. But, this last year has been very stressful and it has taken a full year to find a solution to that. Stress management is key to maintaining a good lifestyle, I exercise a ton, and working to add meditation to my daily habits (you need both).

I love the flexible time, if I need to take a day off I take it off, and I put it back in somewhere else. As the company has grown in size it is a little more rigid in structure, I've got meetings on Monday/Tuesday that I usually can't skip. But usually that leaves Wed/Thur/Fri free for project work and no meetings.

I love to travel and this lifestyle. Since the entire company is remote it doesn't matter where I am. I traveled for all of 2012 and 2013, I spent a year in Australia, 6 months in europe/UK, and 6 months in South America. I am typing this from Nice France where my wife and I will be for a month, and then Croatia for a few months. I use AirBNB to find places to stay and it has worked out brilliantly so far.

I go to 3 to 4 conferences a year, sometimes more, I really enjoy the industry I am in and have a fair number of friends through that network + work meetups. Given the nomadic nature of my life for the last 5 years, and the higher hours I don't have a ton of close close friends. Just a few from college and it is hard to maintain those friendships when we are all different places in the world. I am looking forward to being a bit more settled as I've gotten older :).

The hardest part? It is hard to shut down, it is a constant battle to make sure my life has balance, both for hobbies, and for my wife/family. I would imagine that once kids are added to the mix that will really adjust some of my priorities and time :)

If i may ask, what is your strategy for long term airbnbn rental? My wife and I are thinking of doing the very exact same thing that you and your wife are doing, and would appreciate the info.

Yep, basically I pick out the ones I like and email them that I am looking for a place for around 2 months and if they can give me a better price. I generally do that with 3 to 5 of them and see who comes back with a competitive rate and price drop over weekly. Usually asking nicely is great and they love long stays as they don't have to mess with turn over.

If I can help in anyway my email is bwbbwb@gmail.com, Thanks, Ben

I work in a small country in Asia on an early stage startup (raised seed), before starting this I was told to have a work-life balance. Go to work, spend 8-10 hours, come back and offload your mind for a few hours. I tried that for a few days, it was horrible.

I wake up at 6am for a morning run, do some meditation, get a quick breakfast and am in the office by 8am. Time moves too quickly (startup relativity?), the next thing I know it's 10pm and everyone has left the office, by 10/11pm i'm out the door, back home and asleep by 12. This is Mon-Sat.

On Sunday a few of my colleagues and I would find a cafe and work there from 10am-7pm then head for dinner or back home.

I haven't seen my bestfriend in 3 months, it didn't work out with my girlfriend because of the working hours and i've missed too many birthday parties to count.

It's not ideal but I found if I really wanted something, I have to be willing to give up something of equal importance to focus. If I could go back I wouldn't change anything about this.

What's struck me is how much it's changed over the last 6 (!) years of building CloudFlare.

2009: "Student Life" / CloudFlare started as a student project. First year felt very academic. Worked irregular hours. Weren't sure what we were supposed to be doing. Lots of research. Lots of change (relocated from Boston to the Bay Area). The whole time we didn't really think we were building a company, we thought we were researching an interesting problem and seeing if we could come up with solutions for it.

Pre-October 2010: "Playing Company" / We'd raised money at the end of 2009 and hired our first employees and moved into our first office in Palo Alto in Jan 2010. I'd take the train from SF every morning answering emails on my iPad on the way down and playing Angry Birds (for a stint I was among the top ranked players in the US) on the return. We struggled to get our first 100 beta users and took the whole team to Vegas when we did. We weren't sure exactly what we were building and sometimes the uncertainty made me anxious but generally this was a fun time. The 60 days before we launched at TechCrunch Disrupt on Sept 27th were stressful but fun and incredibly productive. Everyone had a clear goal and date it needed to be done by.

Personally, I was wearing many hats (occasional coder, biz dev, and primary customer support) and nearly 100% of my time was dedicated to obsessing about CloudFlare. There was still a lot of uncertainty and throughout the course of 2010 there was increasing sense that we had a big opportunity and it was ours to take or screw up.

During this time I tried all kinds of tricks to manage my own psyche. Most effective was going to Suchadda Thai Massage near my house every weekend and getting a 90 minute really deep tissue massage that was hard enough that it took my mind off anything other than the knee or elbow being jabbed into my back. I'd been dating a woman who was an academic for the last two years but had become a pretty terrible boyfriend. Not a surprise that we broke up just after this period.

October 2010-December 2011: "Chaos" / We launched. We didn't get around to putting on any limits on who could sign up so anyone and everyone did. Thousands signed up in the first few days. Every signup increased the traffic across our network. There were only 8 of us and we were running a 24x7 network. I lost the ability to sleep for more than about 2 hours at a time. My phone would buzz with every network issue. At the same time, it was fun to see that things were generally working. Customer attention lead to investor attention and the relationship with investors shifted from us pitching them to them pitching us. I wasn't doing any more coding and spent much more of my time managing potential investors and trying to recruit. We moved the office to San Francisco within a few blocks of my house. Being closer removed the regular routine of the train and, somewhat counter-intuitively, meant I worked longer hours because the last bullet train leaving Palo Alto didn't define the end of work anymore.

With the lack of predictability came a feeling that every day held a new crisis. One afternoon in the spring of 2010 we got word some group called Lulz Security had signed up. Then the media started calling. We had no idea who Lulzsec was. I stayed in the office well past midnight reading Twitter and articles on the group and trying to figure out what to do. I only went home when I got spooked sitting in our dark office and thought I heard someone. I headed home only to be awakened by a call from my co-founder. Turned out someone had broken in and four laptops had been stolen. I raced back to the office and a bunch of us holed up on a conference room and debated (seriously) whether it was the hackers, law enforcement, or some corporate espionage agent who had broken into the office. That's how crazy life felt. Turned out the truth held fall less intrigue: it was a simple burglar who had broken into several other offices and was caught several months later.

I started dating a cancer surgeon. She lived on the other side of San Francisco and had a similarly chaotic schedule. We'd find time to get dinner a couple nights a week and exchange stories about the chaos in each others' lives. Having nothing in common almost felt like a virtue for a time as we could both provide each other an escape.

2012 - 2013: "Growing" / We built up the start of a competent team and things began to feel more stable. I started to attend more external events and spend more time outside the office. Started attending more conferences. Telling the CloudFlare story more broadly. I started writing regularly for our blog, largely telling stories about technical challenges we'd faced and how we solved them.

Being more of a public figure made me more of a target. Some of our less savory users, or the hackers trying to take down the sites we protected, decided to mess with me from time to time. I'd been pretty casual with the personal details of my life. It wasn't hard to find my cell phone number or home address. One night at 4:00am I had the SWAT team called on my home. Thankfully they rang the buzzer rather than breaking down the door. At the office, we regularly had bomb threats phoned in. We became pretty good friends with Maggie the bomb sniffing dog. Our Board suggested that I should have personal security, especially when traveling, which seemed absurd given how small a company we were. It also didn't thrill my quite private physician girlfriend. Having nothing in common started to be more of a liability and we broke up.

2014 - Today: "Real CEO" / Today I have three jobs: recruiting, external affairs, internal affairs. I spend about equal time on each. We're hiring about 3 people a week at this point and I still talk with all of them to answer their questions and try and judge whether they'll be a cultural fit. External affairs involves speaking to customers, investors, analysts, bankers, media, etc. Internal affairs involves a bit of product strategy but mostly managing people and team dynamics. Talking with CEOs of public companies that are far ahead of where we are today, my sense is this will be my role for the rest of my time leading CloudFlare.

My work day is pretty tightly scheduled but I have quite a bit of control of that schedule. I don't have a lot of downtime during the day which has made it harder to find time to do things at work I used to really enjoy, like writing technical blog posts. I find myself much more playing what Jeff Bezos, CEO of Amazon, described as "switchboard operator": taking some input of an idea and routing it to the right person on our team. It's rare that I write an email that's more than a couple sentences anymore. It surprises me every day to walk into the office and see so many people. We've passed the Dunbar Number of employees and it's hard that I don't have a personal relationship with everyone on the team. Soon I won't know everyone's name. We've tried to keep the organization very flat, in order to ensure that we're the kind of place where the best idea will win, and I am surprised whenever I hear someone hesitates to "waste my time" with something because I'm "the CEO." I try to stay approachable but see how that inherently gets more difficult over time.

I'm getting better at taking time for myself, secure in knowing there's a great team handling things better than I could myself. As a fellow founder said recently, the job of CEO is to fire yourself from every job within the company -- and replace yourself with someone more competent. I like that and think it's right.

I'm proud of the fact that the three of us that co-founded the company are all still at the company and are all still friends who respect each other. That's very rare. Our story would make for a very boring book. Other personal relationships are sometimes difficult. You lose a lot of friends along the process of starting a company -- largely because I haven't made time to keep up the relationships. At the same time, I've met a lot of great new people who I think will develop into meaningful, long-term friends. Dating presents a real puzzle -- but that's a whole other topic for another time.

Looking ahead we're likely on the path to being a public company and I'm trying to spend as much time talking with other newly public CEOs about how that changes their lifestyle. For now, I count myself fortunate that I can take a few hours on a sunny Saturday morning in San Francisco and, on a whim, sit down and write an answer to this question and not have to send it my our compliance department to ensure it doesn't contain any forward-looking statements.

Great story thanks for sharing. The parts about your personal and business security problems was surprising. I would think Cloudflare is a pretty niche product with a rational customer base. But I guess if you really piss off some developers they can think of clever ways to make life miserable.

Thanks for posting this, it's amazing that HN attracts users and content like this.

You seem really positive about your work, like you enjoy all aspects of it. Is that true, or are there parts you hate?

wow amazing story, thanks for all the detail. Very enjoyable to read. Quick question, whats most influential book you read? (in terms of decisions or directions you took with CloudFlare)

YC reject here, Winter '14. Started 11/12 as a side-project while working at another YC backed startup. Applied to YC after establishing baseline product market fit. Worked 10hrs M-F at job and another 4-6hrs on startup when home. 10+hrs on Saturday & Sunday on startup.

Went full time 3/14 after getting into another accelerator. Since then work about 10+ hrs 6-7 days a week, sometimes taking the occasional weekend off. Started charging 5/14 and have been profitable since day 1. Pay myself and cofounder a nominal salary (~2k/m). By early '15 have grossed over 100k and still profitable.

We have about 5 consistent contractors that we pay for different parts of the business and work harder than ever managing time and people. I don't code as much as I like to anymore (still ~40 hrs per week), but I work just as hard. Only ever have more things to do, never less.

I have a very small consulting firm. I spend 20 hours a week on a gig that I picked up 3 years ago, and I have two part-time people working for me about 10 hours a week each. I have a hands-off business partner who handles the billing. It's my mother, actually. She has her own consulting gigs, so about a year ago we just decided to combine our billing.

It pays pretty well--even though I'm nowhere near charging what I've been told would be the going rate for my skill set--well enough that my wife and I took three camping trips and three international trips last year, and took the entire December holiday season off.

I don't own a car anymore; we are a one-car household now. Well, I do own one, but it hasn't ran for three months now and I'm probably just going to donate it. I exclusively work remotely. I'll occasionally walk to a coffee shop or co-working space (I live just outside of DC in the Old Town district of Alexandria). It's kind of lonely, but it's a hell of a lot better than having a boss.

The rest of the time, I (try to) make things that interest me and try to develop them into salable products. But, I'm having some issues with self-doubt. I've had tons of side projects over the years and none of them have led to anything, mostly because I've never managed to put any of them up for sale, because I believed they weren't good enough to sell, because I tend to focus on big chunks of interesting, technical work rather than the long-tail of chore issues, both technical and non-technical.

But finally, after 10 years, I got one project up and running on its own site with a "buy" button. Nobody has bought it, and I still don't really feel like it's worth buying, but at least I've gotten over that one particular hangup.

I'm hoping I can just keep whittling away at the hangups and skill deficiencies, one by one, until I've got something with all the right parts and all the right moves. I'd just like to know how close I am, though.

I think "manic" describes things well. The highs are very high and the lows are very low. And if you're just floating along in the middle, you're always wanting more. It's one of the reasons trying to do this on your own is so hard. Ideally when you're having an off day your cofounder is there to pick you back up. In this sense, being in sync with your cofounder isn't always a good thing.

On any given day, it's difficult to manage everything. When you have customer service, outreach, growth, and development to do, something gets dropped. There's never quite enough time.

Then there's the difficulty in taking time off. When you try to make time for other parts of your life, you're always looking at the things that you didn't get to and thinking about when you're going to do them. I don't go to as many happy hours as I used to; I certainly don't organize them. I'm not playing volleyball right now. I try to workout, but it's hard to tear yourself away from the computer when it'll just take another hour to finish your current task. It affects your conversations, your relationships, your health, everything. It is consuming.

On any given weekday, I work at least 10 hours. Generally it's about 12-14. I make sure to take a night or two off to spend time with my fiancee. On the weekend, I try to fit in time with her as well but I'll still get in at least 4 hours each day, sometimes more like 8.

I get stressed about money a lot. We're bootstrapped so not everyone is in this situations. In any case, everything is framed in terms of how many months we have left. That 12 dollar sandwich? That's a couple days of server time. An expensive car repair? That's a whole month of our runway.

And yet, it's the most rewarding thing you can ever do. You get to build something from nothing. People use it. They talk to you about it. You are making the decisions. And it isn't going to last forever. It'll last for a long time, but it'll get better. But most importantly, I wake up every morning without an alarm and am eager to get back to work.

I can attest to this. it's like a roller coaster. for me the lows are when nothing happens. it feels like eternity. the highs are when you make sales and everything goes well. it's something I am working on, trying to separate emotion from the business like a robot would. It's expectation management.

Simply put. I need a vacation but can't take one.

seeing this makes me laugh.

of course you can take a vacation, you just don't want to. your ego is bound up in a workaholic identity and you've lost grip on reality.

every small business owner or co-founder i've ever known takes at least a week off every year and most government holidays, because it's the responsible thing to do when you work with other humans.

I am in year two of my startup and it's basically:

Wake up at 7am, work out, work until 7pm, rush home to eat quickly for 20 minutes (on the walk to and from work listening to podcasts about startups and business), and working until midnight.

Weekends, spend the afternoons working. Paying ourselves (two founders) $36k/year until we reach certain milestones.

I make tradeoffs - there is only really time for work, working out, and occasionally going out. This means not a lot of time with friends, going back to China to see extended family, and constantly feeling stressed.

But getting to work full-time on something you believe in and having the opportunity to build a great business and achieve financial independence is totally worth it.

5:30am - 6:30am: wake up, coffee, meditate 6:30am - 7:30am: customer support from overnight 7:30am - 9:30am: breakast with family, kids to school 10:00am - 4:30pm: work, office, lunch 4:45pm - 5:30pm: beer with coworing space coworkers 6:00pm - 10:00pm: Dinner with Family with support sprinkled in throughout the night. Yoga class sometimes. 10:00pm - 5:30am: Sleep

(Of course in the real world there are lots of deviations from this, but this is the goal schedule.)

I bet it's no more than ten minutes on a busy day, between 6:30 and 7:30, between coffee and thinking about work. Meditation is hard when you have something to do and must do it. Meditation is an Eastern thing and it doesn't play well with the Western values.

Yeah I do about 10 or 15 minutes with the headspace app. It's not a lot of time but it's quite nice and even that little bit of time is very impactful.

I try to work on my startup on the side between a job and studying for a masters. I spend time on my company (an ecommerce based wearable startup) developing and shipping product.

The free time I have I use to run around Hong Kong Island where I live and elsewhere, in the university library reading various books.

My wife and I are co-founders and we have a 3 year-old daughter. Our startup is also still in its early stages, so things are pretty busy and often chaotic. I can definitely say that, as a necessity, we've become much better at time management than we ever were before.

Our days are fairly planned and we try to keep things routine as much as possible, consistency helps immensely. Also we've managed to ensure everything we need is fairly close by. We live about 10-15 minutes from work and our daycare and gym are both in close proximity to our office. We each typically have two scheduled mornings a week to hit the gym, one of us goes to the gym and the other deals with daycare. We also occasionally hand off daycare pick-up to allow the other to work a bit later. In fact, we hand-off on a lot of things to make everything work, particularly meetings, typically only one of us will go so the other can stay at work and grind on other things. As a software developer this is pretty important, I can skip out of a lot of meetings and keep working on product and we can catch up on what happened in the evening.

Having a child means our days need to be somewhat time-boxed so there's little room for severely late work hours. I actually believe this to be a good thing, as I'm forced to get the most out of my work time and continue to improve on my time management skills. That said, we're often catching up on things during downtime, weekends, evenings and since we live together, we have the advantage (or disadvantage depending on how you look at it) of being able to discuss work whenever we need to. To make things even more interesting my brother and father work in a related business, so family dinners can be... interesting.

Outside of that we try to keep everything pretty normal and we enjoy our downtime. We like to cook a lot, we make a regular trip to the market most Saturdays with our daughter. We cook dinner with our daughter often and eat at home often which provides valuable family time. The grandparents usually watch our daughter on Friday nights so we can hang out of with friends once a week as well, and we occasionally sneak out to have a drink together, after her bed-time, while they stay and watch her.

Almost all of our family lives nearby, so my parents and her parents help out a lot. It really starts to become a team effort to make everything work out without an excessive level of stress. I can't stress enough how important family is when things get to this level of "busy".

Like most people here, we love what we do. We don't mind being somewhat "always on" and we try to plan our lives in a way the reminds us to do other things too and not to neglect family and friends. That's the bigger challenge I think, not figuring out how to work hard at something you love, but remembering to live your life too.

Overall, we are very fortunate things have worked out as well as they have.

I'm also married to my cofounder and the experience is a lot like yours... Startup families are very tight:) Some people say "startup is a contact sport" but we prefer "startup is a team sport". Keep being grateful and good luck!

Roughly the same hours as when I worked for someone else, but I care a whole lot more.

Early stage?

Just over three years, about 27 employees.

Clinical addiction to creating, with associated negative quality of life effects.

Working remotely from a house with 5 kids in Florida.

Developers are working remotely abroad.

I work probably around 60 hours/week, but it is hard to say exactly since work and fun intertwine.

All on postjobfree?

Yes, all on postjobfree.com 4+ years part-time + 3+ years full time.

Very similar lifestyle as when I was a student - small apartment, eat in most days... but couldn't be more satisfied with my "job" :=)

What stage are you in? early days?

My lifestyle is pretty great right now, but it has changed and improved remarkably throughout the years.

I have found that at about $30K a month in spending money, is more money than I need, even in the most expensive cities (as long as I’m hanging out with normal people with normal jobs and don’t do anything to crazy that month).

Currently, I live between Aspen, CO and San Juan, PR. I live in Aspen, because it is my favorite place in the world. There are so many amazing outdoor activities and the girls there are the best in the world (for me, I'm kind-of and extreme sports person and there are a lot of girls like that up there). The party scene is hard to beat up in Aspen, in both the summer and the winter.

Mostly though, I dirt bike all summer in the mountains and ski and snowmobile all winter.

I just recently moved to Puerto Rico for a percentage of the year for the great tax benefits of living here. So far it has been really good. I live in Old San Juan, which is somewhat like living in the Mission in SF. Dirty, grimy, hispstery and fun.

I walk or get driven everywhere I go. I don't like driving at all and don't really need to either place I live. I am in walking distance to 20 great bars and restaurants in both places.

I try to work every weekday from 8am-4pm EST no matter what timezone I’m in. That doesn’t always happen, but the more I work, the better, more stable and more profitable my business gets.

What I have found to be most important, is to make sure that I get up and get emails out early, so that no matter what is really going on in my life, it signals to everyone who interacts with my business that, I’m up early and working hard every day, which is often the case anyway.

However, for example, on Friday me my employee and a girl from down here, took the day off and had an awesome drunken brunch on the beach.

My number one employee and best friend, lives and travels around with me. We are an awesome team together and get shit done in all parts of our lives. We eat out every meal and I literally pay for everything for him when we are together. It feels a lot like he is my kid in a lot of ways, lol.

I’ve had girlfriends throughout the years, but almost every one of them has been unemployed or working on something like acting or trying to start a business. It is really hard for me to date someone with a 9-5, I think because my lifestyle is so flexible (I also require a lot of attention). My last girlfriend was a consultant and worked at home, which was the best set up so far. We would just work next to each other from each others apartments.

It took a good amount of time to get here. I’ve been founding companies for about 6-7 years. This is my third entity. Back in the day I was living on the floor in the ghetto of Berkeley, CA without an extra dime to spend on anything other than Ramen.

I’m looking to the future right now. Hoping to grow my business, save some money, spend a lot of money and have a lot of fun.

My next big plan, is to get a harem of girls to simultaneously be my girlfriends and travel with me between Aspen, Puerto Rico and the rest of the world. I’ve been working on it, getting apartments set up in both places that will work for this. Also, I’ve been looking for super smart, super hot girls who would be down for this.

So far, you’d be surprised at the reactions of most of the girls who I tell my plan to. Very few have been negative about it. Most have been at minimum supportive and they think it is cool.

I know it is a ridiculous “goal” for the future, but there are no real rules and boundaries in my life and I am going to do my best to take full advantage of this one awesome life :)

So far I think I’m on a good track.

I will admit I actually double-checked the font colour for this in Chrome's Developer Tools, so surprised was I that a post containing the phrase "My next big plan is to get a harem of girls to simultaneously be my girlfriends" hadn't received any downvotes.

Haha, like I said, I too have been surprised at the general lack of negative feedback this has been getting when I have brought it up to family, friends, acquaintances, etc.

How do you make $30k per month?

I buy and sell traffic to media companies on Facebook.

I assume the traffic is generated in the form of ads from the people who are selling you the traffic? So you're sort of like an advertising company?

I build and sell an enterprise software product. First 12 months--sales were low. Eventually, I saw sales in the $10-50K/mo range. I'm now seeing $50K-100K/mo. I work alone, I have no investors, and my overhead is minimal.

My main luxury is eating out. I don't sweat ordering what I want. I get that appetizer when I want it. I don't wince when a waiter reminds me that refills cost.

I live in a modest city apartment.

Last year, I took a few short vacations. Nothing extravagant. They were the same types of vacations I might take if I were employed as a developer.

I travel a lot to promote my business. When I travel on business, I make sure I'm in a nice hotel, eat nice meals, and I travel comfortably.

When I'm home, I wake up around 10am. I go through email and whatever other distractions I come up with . I go eat lunch and then I head to my office. I usually work until dinner time. Some days I work after dinner until I go to bed. Other days I don’t. I slow down, here and there, to avoid burn out.

My personal financial goal is to build a retirement account capable of supporting a modest life style. I don't know what the rest of this ride looks like, so I'm trying to capitalize on it and build some personal security.

I don’t have much of a social life right now. When I’m in a mental state to produce, I get quite stressed when I have to attend a party or otherwise disrupt my productive work to “hang out”. I have friends though and I get to spend some time with them. Usually it’s when we cross paths on our work travel or volunteer activities.

I'm pretty happy with my situation and have a lot of satisfaction from my work. Some of the things that I like the most:

1. I don't have to ask anyone for permission for anything. If I want to do something, I go and do it.

2. I don't have constant reminders about my low place in the organization's hierarchy. My customers and I enter into a business transaction as peers. This mutual respect is very important to me.

3. I have absolute control over my work. I like the freedom to pursue my product's vision without having to stop and justify it to others.

4. I like succeeding at business development. I’ve met a lot of “pure business” people who would like me to believe there’s something special to what they do. There isn’t. As a programmer, I find this very empowering.

5. I also like succeeding without investors. I started my entrepreneurial journey on HN and for a time believed I needed someone else's blessing to succeed. While I have friends who have done well with investors, I like knowing that my two hands made something from nothing and got me here.

This was highly inspirational and I loved it, especially "My customers and I enter into a business transaction as peers. This mutual respect is very important to me".

If I might ask, what kind of enterprise software can generate that much profit from a one-man shop?


My business is in the IT security realm.

When did you start your business?

Why do you work alone? You can definitely afford an employee now.

When did you start your business?


Why do you work alone? You can definitely afford an employee now.

Those who know my situation ask this. Right now, I'm able to manage the business side without too much trouble. I like building the technology and working with my customers.

If I "grow" my business, my role will change, and I have little interest in this.

Eat, Sleep, Conquer, Repeat.

Playing CS:GO most of the time until a customer needs help or a bug needs to be fixed. I'd like to get a second monitor so I don't have to alt-tab all the time.

Heh, that reminds me of this video: http://youtu.be/uRGljemfwUE

awesome!! thanks internet!!

my god what series is this. its hilarious!

this video is accurate except im talking to customers.

what type of startup is it? SaaS?

yeah saas

Brute, austere, spartan on one side and counter-tempered with persistence, determination and long-term grit. On the other side, it's like living in a dimension outside of space, time, matter, mass and gravity.

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