December 20, 2019

What's it like to bootstrap a business before it can financially support you?

Founders lose sleep over all kinds of nightmare scenarios, but running out of cash probably tops the list. A business can survive the comings and goings of personal motivation, positive press, even co-founders. But depleting your money is like depleting your drinking water. It's existential.

Enter Indie Hackers: a community largely (but not exclusively!) made up of bootstrappers who shoulder this huge financial burden personally. You'll find a lot of discussions here about how to grow a business without outside capital, but not many about what bootstrapping is actually like — personally and emotionally — in the months or years before earnings finally cover living expenses.

So I asked a number of bootstrapped founders about this. They've generally taken one of three approaches to bootstrapping:

  1. opt only for business ideas that can generate good revenue upfront
  2. jump into bootstrapping full time while relying on personal savings
  3. bootstrap on the side while working a day job

Check out their full answers below.

Generating revenue immediately

👤 Rob Fitzpatrick, author of 🇪🇸 The Mom Test ($10,000/mo)

I've tried a bunch of options:

  • Cross-subsidy, where you have a high-earning, part-time profession and limit yourself to working X days per week.
  • Save and burn, where you accumulate a pile of cash to buy yourself X months of runway.
  • Idea selection, where you only agree to work on ideas which have the potential to deliver rapid profits.

I quite enjoyed this last one, and we had $50K in committed sales within the first week, before we had really done anything other than ask folks if they wanted to give us money. This was fun and easy and paid the bills from day zero. I'd do it again if paying the bills was a top concern. The hard part is rejecting lots of wonderfully "good" ideas just because they don't fit the constraints that you happen to be enduring at this particular moment.

Bootstrapping is only stressful before you have a working business, so the "strategy" should be in either creating enough free finances to allow yourself to casually survive that stage regardless of how long it takes, or in picking ideas with an extremely quick and reliable payback period. Once the business is working, then it's no more or less stressful than having any other job.

P.S. You also need to be willing to fail gracefully, for example by admitting it early enough that you're able to give your employees fair warning, help them find excellent new jobs, and transition your customers onto a competitor's product. If you aren't able to acknowledge your own failure, then you're going to have a pretty miserable time through much of the bootstrapping process, and will end up causing a lot of preventable damage to both yourself and the people you care about. I did a bad job of this in my first company and have tried to handle it better since then.

Using personal savings to fund your business

👤 Slav Ivanov, co-founder of 🇧🇬 Encharge ($140/mo)

I've supported myself with savings while bootstrapping Encharge. Also, there's a bit of passive income that takes care of about 1/3 of my monthly expenses. I still have enough cash for another year and a half. Hopefully, we'll get to profitability by that point.

However, I underestimated the time it would take for a startup to get going (based on previous experience). That's taking a toll emotionally. We've pivoted several times, and we're still looking for product-market fit.

My co-founder does consulting to pay his own bills at the moment.

👤 Amir Rajan, founder of 🇺🇸 A Dark Room iOS ($7,500/mo)

My company financially supports me full time. It was established "accidentally" in 2014 when a mobile game I built hit the number one spot in the App Store (A Dark Room). With the extra runway, I developed four more games, and just a few months ago released ADR to the Nintendo Switch. I am now working on a game engine based off of everything I've learned over the past five years (DragonRuby Game Toolkit).

Financially and emotionally it continues to be a rollercoaster. Primarily because I can't "forget" what it feels like to work on something you enjoy and find meaningful. Sure, I have enough money for, say, the next five years. But what about the next forty years? This is kind of what keeps me up at night: there is no guarantee that I'll be able to keep doing this "forever" (given how quickly technology changes).

Ignorance is indeed bliss at times.

👤 Rodolphe Dutel, founder of 🇫🇷 Remotive.io ($15,000/mo)

I always loved side projects. Tumblrs, newsletters, blogs, startup weekends, etc. None of my projects gained significant traction or made good money, but I learned a ton. That is, until the day I started Remotive.io and people started tuning in. Launched in 2014 as a side project; went part time in 2017; then full time in 2019. And I'm still at it.

I started it while working at Buffer. (They publish salaries; I made over $100K/yr.) At the end of 2016, I realized I'd probably be able to make over $50k in 2017 through Remotive + consulting + severance. That covered my expenses, so I left my job at Buffer to work on Remotive… PART TIME!

Why part time? The reason I bootstrapped was to control my time. As soon as I covered my living expenses, growth didn't matter. I wrote a novel in French. It's on Amazon. Took me a year and a half. Every morning, I wrote; every afternoon, I worked on Remotive. I'd rather live with less money and no strings attached!

Remotive is more of a service business than a SaaS company, and less than 15% of the revenue is recurring. For the stressful bad months, I'd always tell myself I could do some consulting.

I finally went full time in early 2019. I also welcomed a CTO. And even though Remotive is now my main gig, I still run side projects! :)

Working a day job until business profits support you

👤 Matt Verlaque, co-founder of 🇺🇸 UpLaunch ($103,000/mo)

My co-founder and I worked part-time as firefighters while bootstrapping our business for over a year before it got serious enough to consider leaving. The trigger point for both of us was that our CTO went full time before we did. As a leader, that felt wrong and didn't sit well with me. If we couldn't bet on ourselves, how could we ask anyone else to bet on us?

Jake and I were still making precisely zero dollars at that point. It was still a gamble, but it was one that we had to make. We planned out ahead of time to tighten our belts, but also set a hard deadline: if we weren't personally making at least $40K a full year after leaving the fire department, we would figure out the next move.

Shocker, we didn't hit that mark — but luckily, the momentum was heading in the right direction and we decided to keep pushing. Everyone always says things like "people quit right before they're about to succeed." There are two sides to that, because I also think people will keep doing things that don't work forever because they're blind to the fact that it's not working. However, in this case, we just needed a little more time and a few more adjustments and we started to hit our stride.

There was a decent amount of surprise from the fire department. Jake and I were both company officers with bright futures, and no one really expected us to go another direction.

Oh well… SURPRISE!

👤 Matt Sencenbaugh, founder of 🇺🇸 WrestlingIQ ($250/mo)

I'm in the midst of it now. I'm mostly happy with my progress, but continually struggle with maintaining my patience. I also struggle mentally with the molds and wisdom of the bootstrapping community.

In the spring of 2016 I worked backwards from my anticipated monthly expenses, then set out to find freelance work that would cover it. One of the first conversations I had was with a friend of mine who was looking for his first engineering hire at the local office. I accepted a three-day-a-week job. That has turned out to be infinitely better and something I'd recommend to others.

Based on my low expenses (a situation I know not everyone has) I've been able to live a fairly comfortable life, continue to sock away money in my IRA, and save for a down payment for a modest house in about three years. My partner and I don't live extravagantly. We cook all of our meals and trend fairly hard toward hermit-like introversion on the weekends, which helps keep the bills down.

The steady job is an infinite runway since I have a software- and mobile-engineering background to bring to the table. Since incorporating the LLC, I have probably put $15K in cash into the business. I expect to make a small profit for the first time since I broke ground on the code in November 2016.

Financially, I think this strategy has been the right fit. In many ways, though, I feel like a fraud, as if "indie hacker" or "bootstrapper" means you need to be some sort of starving artist (which is also a harmful self-identity, I think). Emotionally, though I've had a lot of ups and downs, I've been relatively even keel.

👤 Paul Joseph Cox, founder of 🇺🇸 The Church Co. ($28,000/mo)

The hardest part about bootstrapping is being patient. If you don't quit your day job you have an infinite runway to work with. At over $16K MRR I still haven't gone full time, but not because I couldn't. I've just chosen to bring on other people to run other parts of the business.

When I started The Church Co, the expenses were relatively low. I paid $30 a month for AWS and $50 a month for Intercom. That and my time were the only investment. The Church Co is a do-it-yourself website builder for churches and nonprofits. I ran it in beta for a year for free before turning on payments in July 2017. I sent out the email letting my 17 customers know that they needed to put in their credit card, and eight of them quit right away.

It's been two and a half years since turning on payments. I'm at $16,300 MRR and I'm still working full time at my day job. Discipline has been key during this time. Every morning I would wake up at 5am and work from a cafe until 9. After work, I would walk home and answer my customer support tickets. Each weekend I would do around 10 hours on bugs and new features. It was honestly the hardest few years of my life. Just this month I decided to bring on some support. I hired five contractors and distributed all of the work between them. It's another delay in going full time, but it sets the company up to scale more efficiently.

I'll likely go full time on The Church Co eventually. I don't regret the way I've done it. When I finally take the leap I'll have all of our systems in place to allow me to run the business effectively.

Check out these related questions we've posed to experienced founders:

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  1. 4

    Thanks for sharing all those stories. I'm sure many of us here can relate. Particularly the ups and downs.

    In my first business I decided to quit my day job and start up the next day. My wife also said that she didn't want to work ever again. So I was the only income. My original co-founder and I bootstrapped but when we grew we had to borrow money to support our growing staff and very long cash-flow forecasts.

    In 2007 we parted ways when the businesses went from bad to worse. As part of getting him out of the business I said I would take on all the debt and responsibility. It took me 2 years to get things back on track then the financial crisis hit in 2009.

    In 2010 I started Hunter with a new co-founder. I carried the debt. We grew again and I needed more cash to keep things moving so borrowed again. Mind you when we started Hunter, we were offered $250k from an investor for 20%. He would also mentor us. Because of various reasons we declined. In hindsight that was a huge mistake.

    In 2017, we lost our biggest client and all these other clients due to corporate restructuring. From 2017 - 2019 I learned more about finance and business in general than I had in the past. I read a book called Profit First (amongst many many others). We then started to implement the Profit First principles and for the first time I feel we're taking back control. Slowly getting rid of tax debts, credit card debts and having reserves in the different bank accounts we've opened. I still hold the big scary debt, however over the next 5 years my goal is to pay this down and then have 100% financial freedom.

  2. 2

    Great series of interviews! Definitely helps morale to hear the different approaches that people made work.

    I worked for 4 years at a company that I had a good sense would go public, intending to use that as my seed capital. It worked out and IPO / Vesting / Leaving all happened in a 60 day window! But, building the product took longer and more cash than I expected, so after a year I've taken a FT job for a while until it can support me. It's definitely rough but I'm motivated to get my co-founders paid first. I've organized things so I'm not mission-critical to much except product and strategy, so it's doable for a while.

  3. 2

    A nice thread! Personally I dived in and after 5 months I'm making $2k/m (and hopefully a lot more in January!) It does depend on personal circumstances though and I had a pretty extreme reason to quit my last job as the IH podcast will tell you!