Working Alongside of Your Bootstrap

I’ve been reading the books Quitter and Start by Jon Acuff on starting a bootstrapped company while working at your day job. I wanted to get your opinions on this technique?

From a few of the introductions I see that some of you have gone this route, so I’d love to get insight from you.

Also, I’d appreciate feedback from people like @andrey who have gone back to sub-contracting or part-time after bootstrapping to keep things going (this is something I’m looking to do as the SaaS product base builds).


I haven’t read those books, so I can’t comment on any of the techniques in there.

I’m more of a pragmatist when it comes to these things. There are some people who insist that you put a fire under your seat by quitting your job and going full-steam with the startup; I’m not one of those people.

I’m tempted to attribute this to being a bit older than the stereotypical early-20s company founder, and thus, having a family to take care of, etc. But in reality, I was of the same mindset back when I was starting out, before the family responsibilities.

I spent the first few months (years? … don’t remember), with Antair, working for a single client (technically a consultancy, but in practice, just a full-time employee), and eventually did products in my spare time, and then eventually quit and went full-time.

I don’t think I have any techniques. It was always more of a “right feel” for me. Working on Wall Street sucked, so I leaned toward my own products until I was able to go full time. If I had a job that I liked, it would have probably taken me much longer to go full-time, since I wouldn’t have had the motivation to minimize my time as an employee.

I totally got that vibe from the podcast. I lucked out in having the ability to try the startup by myself since January, but I think that I am at the point where I am looking at subcontracting to a consultancy firm.

I like the ability to do new things like in a consultancy but at the same time, I don’t have the marketing gusto to break out myself to just do it on my own, plus many of the consultancies I talk to are in the phase of “we have more work than we can accomplish with our current team” so I think it may be a fit to part-time for a team in that situation.

I haven’t read any of those books either, so take this with a grain of salt.

I quit my job just over a year ago incredibly ill prepared for starting a business. So now, a year later, I’m still Really Close to releasing (this time for sure!) Now I’m feeling pretty good. I think the product is awesome. If I can work out this whole “marketing” thing, I think it’ll be a good business.

On the other hand, if it bombs out, I think I will be OK with that. I don’t relish the idea of having to find a day job, but the regret wouldn’t be having tried and failed… just having failed :wink:

I’m in a lucky situation though. I had decent savings to start with, and my girlfriend doesn’t mind me mooching a bit seeing as how she mooched off me for three years while she finished her PHD, plus I can get some pretty good contractor dollars when I want to (which is incredibly rarely, and thankfully I don’t need to… yet.)

So for me, quitting was the right call. That said, I do look with great admiration at people who create tight, focussed businesses in a few hours a night, execute on a solid marketing strategy, and replace their salary before they ever do quit. If you can do that, why the heck wouldn’t you?

I’ve built a few different apps while working full-time jobs. It can be a slow route to go but it does reduce the risk a lot. You also end up trading your free time for your side business. In a lot of ways it feels like working two jobs.

Ultimately it probably depends on a combination of your risk tolerance and your other options such as contracting / consulting.

For me personally, I’ve found that it is not possible to really give a concerted focus on my side business while working for others full-time. I’ve been doing consulting / contract work for a few different clients since September last year and I really like the flexibility it provides me to focus a percent on my own business and a percent on consulting. Right now the split is 60 (consulting) / 40 (business) but my goal is to slowly tip the ratio until consulting is no longer a part of the equation.


I’m working alongside building my business at the moment. I think a lot of it depends on the relationship you have with your employer. In my case mine have been extremely supportive, offering time to fix things or answer the odd support request should I need it.

It can be quite stressful at times and there have been times when I’ve felt like things aren’t moving fast enough but ultimately it means less risk.

I suggest getting into a routine. In the past when I was working and bootstrapping I set a time of day where I worked on my own things. Normally it was 9pm until I crashed.

I also discovered that sometimes after a long day at your normal job you don’t have the mindset to keep going. You just want to relax. What I often did was sat on the couch with the tv on, a whiskey next to me, and my laptop on my lap and coded away. I sort of brought my bootstrapping work into my relaxation time. Worked well for me.

Just don’t let your bootstrapped company slip in terms of time. Make progress every day / week.


This is a great thread, and I hope it stays going for a while. It’s always such a big question.

I’ve recently done both: Jump in whole hog with a string of products, as well as work on my side project/products along side a full time contracting gig.

The biggest problem I face is that I love programming and engineering challenges. I get paid more than I thought I ever would when I got into software development, and I get paid to do something I love. But at the same time, I quickly get tired of working on other people’s products.

At the end of 2011 I quit the best contracting gig I had ever had at that point to go full time on a product. The product didn’t work out, and my partner and I jumped through two more before running out of money in early 2013. Through a long series of unfortunate events, including two deaths in my family, and litigation from a past client (the only time that has ever happened to me), we just never got the momentum you’re supposed to get when you go full time on your project.

Now I have a great job, with an awesome team of people, but I’m so engrossed in it, that all my work on my own products has ground to a halt. I keep telling myself that I’ll get ahead and ease back my hours, but can’t seem to pull myself away from it. I need to set some limits on the time I spend working on other people’s products, so that I can spend time with my family and my own products.

I’ve decided, for a developer/entrepreneur, working on a product is like an investment. You have to discipline yourself to keep putting those dimes and nickles into the bank, and making good trading decisions for the stocks you own, admitting to yourself when you’re wrong, change course when need be, so that you have some sizable assets to work from in the future.

@patio11 does this better than just about anybody I’ve ever seen on the interwebs.


I bootstrapped what eventually became my company – though I didn’t know I was doing that at the time – from June 2006 through March 2010, while working at a succession of two day jobs in Japan. It was a good thing, too, because I think if I had waited another 3 months to quit I might have died. That isn’t much of an exaggeration – I was having stress-induced blackouts by the end of my tenure at the final company.

What really helped me:

  • A product which could be shipped and supported with the time constraints of the day job. The first version of BCC plus all the assorted “set up a website, learn to take payments, etc” cruft took 8 days to get out the door.
  • Learning how to make progress on the business during the typical workweek, with only 5 hours or less allocatable to the project. This generally mean either shipping an A/B test or working in a very constrained fashion on e.g. features for the marketing site, such as shipping improvements to the CMS which was getting me most of my SEO gains.
  • Earning actual money, even in small amounts. BCC made only $1k or $2k a month for most of that time, but I squirreled that away, either in savings or by paying down my student loans.
  • Having a Plan B when quitting. While BCC was day-job profitable by the time I left, due to seasonality in my market it wouldn’t have been during that summer. I had a variety of Plan B’s in the event of not being able to make the rent: tapping savings (see squirrelling, above), using credit cards until fall, or doing consulting. The consulting ended up happening in a major way.

I too did not read either of the originally referenced books, but here is my 2 cents…

There is no true one answer here. It really depends on the founder(s).

The KickoffLabs mini short list:

  • While my co-founder and I didn’t plan on building a company together, we both decided a couple of years before we started KickoffLabs to get our finances in order to make a run at something in the future. This meant avoiding/eliminating almost all debt, minimizing expenses, etc. This enabled us to still live comfortably and with minimum stress while building and marketing our first version of KickoffLabs
  • We were able to do all development in house which eliminated a major expense for us
  • We kept our V1 requirements to a minimum and shipped pretty early (with in 3 months)
  • We didn’t waste time on a free/demo/beta. We let friends and family try things out for a week and then let others sign up and actually pay us to use the product.
  • Signups were slow, but this was OK since we were still figuring things out. As we learned more we made the product better, increased prices/etc. They key here is asking for money at the start since this let us really focus on actual customers.

Too many people overly focus on perfection and delay actually asking for money. This leads to a lot of guess work (what do people actually want) and makes it hard to know who is actually going to be a customer.

In full disclosure, it took us about 9 months to start paying ourselves (revenue > expenses) and likely another 6 months before wives would agree that we were actually paying ourselves. :smiley:


This is one place a partner can really help. If you are working + bootstrapping, your time is so limited. Sometimes you feel like you are treading water. GitHub is obviously the big bootstrapping success story, and they were able to get it done because there was three of them.

Both Tobias and I worked alongside the business when we started (well, Tobias was completing his CS studies when we founded the company). I had a full time developer position back then and luckily my employer was very supportive and even allowed me to switch to working part-time when it made sense after a couple months. I know some people prefer to focus exclusively on their new projects when they start their company, but for us it would have been a bad move. It would have put a lot of pressure on us to get profitable more quickly and this way we had more time to try various things to slowly grow the company instead.

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My story is probably fairly unique. I was in the corporate finance world for a couple of years. Emigrated to London with my wife, worked here in corporate finance for a few years and made some good money. We went travelling for a few months (overland trip through Africa) and came back to London. I started consulting in corporate finance for a few months. Shit happened and I needed to be home to help care for my wife.

I found a app idea that I thought I could make work, and hired an offshore development company to execute it. This is before the word SaaS was even mainstream. Total waste of time and money, albeit an interesting story in its own right, After that I found someone else to help me execute, and we built a prototype. I still had no idea what I was really doing.

But, I plugged away, mostly because I did not have a choice. In the end, I taught myself how to programme and built the thing from scratch (again). A couple of iterations later and we have a great product that is actually doing quite well.

Its been a colourful journey. Its been a painful journey in a lot of different ways and I would not recommend anyone do things the way that I did. I look back and shudder at some of the things that I did or that happened. In the end, however, its actually worked out quite well, and the product is going ok.

Strangely enough, I’ve stumbled across consulting (Laravel) in the past few months and that has taken off. So, I’ve got this SaaS income from the app coming in every month, and I can build the consulting business. Oh, and I’ve got more products that we’re building (ps - we’re hiring - if you know Laravel get in touch).

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I’m pretty risk-averse (family/kids to support) so I’m plugging away at about 2 hours a day to get something going on the side.

Working on the side can be exhausting, but I think that needs to be compared to the stress of quitting a day job/depleting savings.

It can be difficult to find even 2 hours of “fresh mind” time. I tried different work times (late at night, halfway home from commute at the coffee shop, etc) until I found what works best for me (first thing in the morning, before the day job).

You may also be able to find some extra time, when you are normally tired, by being conscious of your energy level and mentally pacing yourself. Essentially reserving energy for the side business.


I lean on the side of juggling both at least for the first 3-6 months, if you go at it full-time at the get go and don’t have any previous experience in the domain you will probably waste allot of time researching and getting things started. If you are consulting/contracting on the side you can get paid during the initial learning/researching phase of your development. Having a steady income can also help you experience with promoting your app via paid sources.

I am not a proponent of the “burn your ships” approach. The idea that quitting your day job will light a fire under your ass is…well, duh. That doesn’t mean it’s a good idea.

There’s a lot of mythologizing the heroic effort in software development, for some reason. This has always struck me as tiresome and foolish. Putting yourself in a bind doesn’t necessarily make it more likely that you’ll do good work; it only means you’ll do enough to survive.

Me, I’d prefer to plan the startup. Save some money. Make some contacts. Try some things and feel free to fail and learn from them without being held back by the fear of not knowing where my next meal/rent payment is coming from.

I do know the difference - I started my consulting firm in the wake of a sudden layoff, because I had no other real options at the time. Sure, I made it work, and sure, I’m still here, but the experience has been way, way more difficult and labor-intensive than it would have been if I had put in some prep time and launched on my own terms instead of scrambling to get myself out from behind the 8-ball.

If you have the luxury of pocketing a paycheck as you build your startup, it seems foolish not to do so. Yes, it’s going to require discipline and a lot of energy. Anything worthwhile does.

Side note: check your employment contract and make sure your employer cannot reasonably lay claim to anything you create for your startup in your personal time.


@Christopher, I definitely went with the “burn your ships” approach. It got me to develop quickly and really got me to do things right instead of it being a hobby.

I think that there is an argument for part-time work. This being said, it’s very hard to find a fit for a company that will embrace you starting your own business and take you seriously. Many companies are in desperate need for devs and want only full-timers. Others in my experience said that they valued entrepreneurship and then busted out saying they would no longer be flexible. It’s tough finding a fit.

This makes a lot of sense to me. I do my best work in the morning when I’m fresh. If I’m going to trade my time for cash, I’d rather trade the lowest-value time I’ve got (just makes sense, right?)


I envy people like @patio11 or Peldi from Balsamiq who have been able to start a bootstrapped company while working at a day job. I think I just don’t have the needed discipline. It would take me forever (I am not a great multitasker).

I think you have to know yourself. How much risk-averse are you? How disciplined are you? For me… I have always taken the “burn your ships” approach and it works for me. I am very risk tolerant and still don’t have kids (something I believe that makes a huge difference).

I’ve done the “burn the ships” approach, and it really really wasn’t a great move for me. I learned a lot, but mostly what I learned was just how far my savings and family life could stretch before it got to a breaking point.

The big risk in burning the ships is that you spend a good chunk of your time, nest-egg, and relationship-capital building something noone wants (or wants, but isn’t willing to pay enough for to make the economics work out.) My advice is to eliminate that risk before you think of jumping ship. Spend your off-hours time learning how to market the product and collecting email addresses. Once that’s reasonalby figured out, it’s a simple burn-rate calculation where you say at $X in monthly burn and $Y in savings, I have $Y/$X months to build and launch the product. Is that reasonable?

(Allow fudge factor for build-time, and consider the amount of time it will take to get enough customers to reach cash flow break-even).