We did both 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 leaders, 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 either?
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 in 1 year after we left 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 were 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!! (lol)
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 & 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 3 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 downpayment for a modest house in about 3 years. My partner and I don't live extravagantly, cook all of our meals and trend fairly hard to hermit like introversion on the weekends, which helps keep the bills down.
The steady job is an infinite runway since I have a software/mobile engineering background to bring to the table. Since incorporating the LLC, I have probably put in $15k to the business in cash. I expect to make a small profit for the first time since I broke ground on the code in Nov of 2016.
Financially I think the above strategy has been the right fit. There is opportunity cost; however, our combined income still puts us above average compared to all US households. In many ways I feel like a fraud because of this, as if 'indiehacker' or 'bootstrapper' means you need to be some sort of starving artist (which is also a harmful self-identity I think).
Emotionally, the journey has been a lot of ups and downs, but relatively even keel. One thing I did not expect is how much I struggle with 'should I keep going'.
Lots of the conversations revolve around real time, such as 'if you aren't profitable in x years, pull the plug'. I think that is a wise thing to think about, but that we are using the wrong measurement. Particularly in a B2B setting, I think you should measure in possible sales cycles rather than months or years. With WrestlingIQ I basically have 2–4 months of a sales window per year due to the annualized nature of sports seasons. I wasn't willing to pull the plug after two years because I essentially had only two seasons of selling the thing. The counterbalance to that of course is that in a highly seasonal sales cycle, I can't quit my part time job in the off season and expect to increase my MRR that same month.
Sorry for the ramble, but it felt good to write :)
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. I enjoyed this approach during early stages, but it can be tricky when the business is succeeding well enough to require all your time, but not so well that it can pay the bills. If I was doing this again, I would choose ideas which can survive without any winner-take-all dynamics, allowing myself to make progress as slowly as is needed while still preserving my finances.
Save and burn, where you accumulate a pile of cash to buy yourself X months of runway. I had a hard time when I tried this because things always take longer than expected, and the right decision (like shutting down and trying something different) can be hard to do if you know you've only got one more month to work on your own ideas.
Idea selection, where you only agree to work on ideas which have the potential to deliver rapid profits. I quite enjoyed this 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. Would do 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.
PS. 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.
I always loved side-projects. Tumblrs, newsletters, blogs, startup weekends… None of my projects had significant traction nor made good money. But I learned a ton.
...Until one day, I started Remotive.io and people started tuning in. Launched in 2014 as a side project, I went part-time in 2017, then full-time in 2019 - I’m still at it.
I started it while working at Buffer (they publish salaries, I made over $100k/yr). I balanced my job and Remotive as a side project for two years before quitting to do my own thing. There was a lot of interest but no explosive growth. Very gradual. I was making enough at my job to run Remotive as a media that didn’t turn a profit.
Took me 1.5yr to start charging. My first invoice felt like the best money I ever made!
When Remotive started to make over $20k/yr, I part-time hired a friend to help me run it as a GM so that I wouldn’t go crazy at my job. I came very close to a burn-out situation, trying to excel at my job and running my side-project.
2014-2016: Remotive is my side gig, I work full time. Remotive made little money
2017-2018: Remotive is my part-time gig. Remotive made around $60k/yr
2019-today: On Remotive full-time, getting paid! 💰
At the end of 2016, I realised I could probably make over $50k in 2017 through Remotive + consulting + severance. That covered my expenses, so I left.
Financially, quitting made no sense. Career-wise, that was plain stupid. Three years after quitting, I still don’t make nearly as much as I use to. Earlier in my journey, I had resigned from Google cold-turkey without any income prospect in mind. This time, I wanted to ensure I’ll make some money.
So I quitted and went on Remotive… PART-TIME! 😍
Why part-time? The reason I bootstrapped is 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 1.5 years working part-time: Every morning, I wrote. Every afternoon, I worked on Remotive! I’d rather live with less money and no strings attached!
I don't run a SaaS, it's more of service biz. Less than 15% is recurring, the rest is merely predictible. Yet bad months do happen, even today. That's stressful at times, so I always tell myself that I can do consulting if things go bad.
I finally went full-time early 2019, Remotive supports me. I also welcomed a CTO. Remotive is now my main gig, I also run side-projects :)
Learnings on bootstrapping ⚗️🧪
Know your burn. 🔥
Meaning, know what your living expenses are. You may not make that much through ramen-profitability but consulting/freelancing helps (esp. recurring gigs with limited involvement). Remember, that’s how 37Signals/Basecamp started! If you don’t know that figure in mind, it’s unlikely you’ll ever quit. Getting a handle on your finance (perso & pro) is key here.
Monetize early. 💵
I passed on several monetisation opportunities because I wasn’t mature/comfortable enough to take people’s money. Monetize early if you can!
Pay yourself first. 🤑
You may want to do paid Ads, or get fancy SaaS or logo. If you can’t pay yourself first, don’t do it! You’re your best investment. Find workarounds and be resourceful, always pay yourself first.
Invest your best hours in yourself. ⏰
I invest my best hours in the project I enjoy most. I’m a morning person, so I worked on my project first before clocking in at work.
Team up selectively. 🤝
Find others who work on a project with similar ambition and time commitment, going as a team makes it fun. Don’t lose sleep comparing yourself to teams who raised $40m. They have a boss, you don’t. TechCrunch is the GQ/Vogue of Tech. They position themselves as aspirational, in reality, they are setting unrealistic standards.
Celebrate milestones. 🎉
Made your first $1k as an IH? Go to the restaurant, treat yourself and your loved ones. IH'ers always look to improve, which is great, but we don't celebrate enough. You don’t know what tomorrow may bring: when you can, treat yourself. Make your journey special :)
Financially, I had some savings that still support me while bootstrapping. Also, there is a bit of passive income that takes care of about a 3rd of monthly expenses. I still have enough cash for 1.5 years ahead. Hopefully, we 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, because of my expectations. We have pivoted several times, and are still looking for product-market fit.
My co-founder does consulting to pay the bills at the moment.
My company financially supports me fulltime. 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 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/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 at times, bliss indeed.
I started bootstrapping Image-Charts https://www.image-charts.com/ back in 2016. Back then, its main competitor, Google Image Charts, was already in deprecation phase since 2012. It could be shutdown at any moment. I needed to build a replacement tool to generate beautiful charts that load fast (under 500 ms wherever you are in the world) with high availability for another of my bootstrapped SaaS (Redsmin https://www.redsmin.com/).
satisfy your own pains and needs 😵
Building products I need is my regular approach to bootstrapping. It’s always easier to find a way to satisfy your own pains and needs, and not someone else’s. I usually start with a pain I have and I try to explore ways to tackle it. The Lean methodology is the most relevant to me when creating a new SaaS. Combining it with Pareto’s law allows me to focus on what matters most — 80% of the effects come from 20% of the causes.
test it as soon as possible with real customers 💵
Once you have your proof of concept or MVP, It’s best to test it as soon as possible with real customers. It will help determine product market fit. For Image-Charts, it meant developing enough backward-compatible features with Google Image Charts to make the switch from it easier. Try not to have too many things before making your first dollar. Limiting your expenses will help ensure financial health from the first or second customer.
reduce risk of money loss & use what you know ⛳️
Using some free tools helped me reduce risk of money loss if the project goes sour. A lot of stress and bad decisions can come from this fear. I have a selection of tools I use with all my SaaS (see list here). It’s best to reuse the tools and frameworks you are comfortable with when bootstrapping your first SaaS. Don’t reinvent the wheel everytime you build something new. Focus on your stack and outsource actions you’re not good at. Avoid recurring fees like plague while bootstrapping — most tools offer freemium plans now anyway.
Momentum is everything. It’s key to be steady and patient at working on the project. Rome hasn’t been built overnight. It’s always a matter of focusing on what matters most at a specific moment. Baby steps…
outsource when necessary 🏖
Currently, I’m fortunate enough to be able to choose the areas I want to invest my time and money in. If I can significantly add value to a topic, I’ll work on it personally. If I don’t think I’m the best at a specific action, I outsource it to the best person I know.
I’m now investing substantially in Image-Charts to make it best of breed in its niche. The plan is to make it ready for the big wave of new users that will come when Google Image Charts is fully deprecated. It’s going to happen eventually—and most likely in 2020. 4 years after the first line of code... Did I tell you about being steady and patient? :)
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 do other parts of the business.
The hardest part about bootstrapping is being patient. If you don't quit your day job you have an infinite runway to work with.
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 of 2017. I sent out the email letting my 17 customers know that they needed to put in their credit card and 8 of them quit right away.
It's been 2.5 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.
Emotionally, I fall into all the traps. With each new customer, I'm the king of the world and with every churn I'm in the trough of sorrows. It hasn't gotten any easier with any amount of MRR. I'm learning to look at averages. We have our high months and our low months. A customer leaving isn't the end of the world.
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.