I've had a similar journey to yours. Started January 1st 2019, early 30s, had a second kid. Loving every minute of it, though I do wonder when the fun is going to end. Every year I'm surprised the business keeps growing. This year my goal is to diversify to try and ease that gnawing anxiety, but every time I try working on something else I feel guilty about ignoring what's already been working for me. Tempted to just sell so I can have a bigger cushion and less distraction on my next venture, but not sure how the current climate would affect the valuation.
My eighth year as a bootstrapped founder
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Re: My eighth year as a bootstrapped founder
#22Thanks for being so transparent. As a fellow solo bootstrapper, I think the thing people most often misunderstand is the relative inconsistency (income, "wins", the camaraderie, etc.) so it's nice for you to bare all. That being said, you do get the consistency of independence and autonomy. As I watch my peers deal with crappy work environments, losing their jobs, and other bullshit, I just keep chugging along: self-…
This is the path I want to take too. Do you find it difficult to focus on the marketing and sales side of the business rather than the building part?
It really depends on what you want to do. By the nature of being self-directed, you elect what roles you want to play. I personally don't love the marketing and sales cycles, so my current business is B2C and I don't do any marketing.
Almost all growth was done via word of mouth. There are business models whose network effects lean in this direction. In order to use my product, you must bring along peers so it's inherently 'viral'. I fell into this by accident rather than by some grand design, but it became obvious to me after I saw it happen. Design a business in which the flywheel can spin without you, if you don't want to spend your time marketing.
My next business that I'm working on is B2B, so I'll have to have a much stronger handle on marketing and sales. But I'm more ready for that now, after a decade of running a B2C business.
Re: My eighth year as a bootstrapped founder
#23I like these kind of stories. Insight into these situation is inspiring. When I hang up the gloves in my current role I'll probably do something similar.
But, come on ... isn't it just a touch disingenuous to call this a bootstrap situation?
I assume an ex-Google developer jettisoned with a decent safety net. Perhaps I'm wrong. But I have a very different idea of what bootstrapping is.
Anyway, kudos to you ... making your own move is brave and commendable.
Re: My eighth year as a bootstrapped founder
#24Thanks for being so transparent. As a fellow solo bootstrapper, I think the thing people most often misunderstand is the relative inconsistency (income, "wins", the camaraderie, etc.) so it's nice for you to bare all. That being said, you do get the consistency of independence and autonomy. As I watch my peers deal with crappy work environments, losing their jobs, and other bullshit, I just keep chugging along: self-…
> Thanks for being so transparent. As a fellow solo bootstrapper, I think the thing people most often misunderstand is the relative inconsistency (income, "wins", the camaraderie, etc.) so it's nice for you to bare all. > That being said, you do get the consistency of independence and autonomy. As I watch my peers deal with crappy work environments, losing their jobs, and other bullshit, I just keep chugging along: s…
Yup, I always say – the hardest part of my job is that if I don't do it, nothing gets done. That copy error on the website. That minor bug. We take for granted the velocity we get by having colleagues. If I get lazy, everything grinds to a halt. And those little nits add up. But I strongly agree it's all worth it.
Re: My eighth year as a bootstrapped founder
#25I've had a similar journey to yours. Started January 1st 2019, early 30s, had a second kid. Loving every minute of it, though I do wonder when the fun is going to end. Every year I'm surprised the business keeps growing. This year my goal is to diversify to try and ease that gnawing anxiety, but every time I try working on something else I feel guilty about ignoring what's already been working for me. Tempted to just…
I recommend having an initial talk with a broker if you're thinking about it at all.
The brokers I've met are happy to talk if you have a profitable business, even if you don't plan on selling anytime soon, and you don't have to sign anything to commit to them. They can talk to you about what you can do to prepare for an exit even if you don't expect that to happen for several years (and it might take you several years to manage yourself out of the business).
I personally liked the broker I worked with and recommend him.[0]
Re: My eighth year as a bootstrapped founder
#26Earlier quoted context omitted.
Yep, the place where I've talked about it the most has been The Software Misadventures Podcast .[0, 1] [0] https://softwaremisadventures.com/p/michael-lynch-on-quittin... (2022, two years into the business) [1] https://softwaremisadventures.com/p/michael-lynch-indie-hack... (2024, just after I sold)
I think scalemaxx is offering to interview you.
Oh, I'm open to that!
Re: My eighth year as a bootstrapped founder
#27I think that "align your business with your passion" is a really important factor that divides the succesful from the not. When I look at Pieter Levels, he doesn't really seem to build ideas to make money. His projects seem to start off as play, and eventually they evolve into something new he can charge for.
Re: My eighth year as a bootstrapped founder
#28Maybe it's just me, but it seems kind of weird to say you earned $8,200 in "profit" when there was no salary. Profit is typically the excess a business earns above its costs. For a solo founder, it can be a little tricky because the more you pay yourself in salary, the less you have in profit (and vice versa). But here, there was no salary. Maybe "earnings" or "income" would be a better term to use? Otherwise someone might (particularly for other years) think that the business earned $PROFIT dollars beyond all other costs, including presumably some sort of salary for all employees/contractors.
Re: My eighth year as a bootstrapped founder
#29Thanks for being so transparent. As a fellow solo bootstrapper, I think the thing people most often misunderstand is the relative inconsistency (income, "wins", the camaraderie, etc.) so it's nice for you to bare all. That being said, you do get the consistency of independence and autonomy. As I watch my peers deal with crappy work environments, losing their jobs, and other bullshit, I just keep chugging along: self-…
Most people start side-businesses for tax reasons, and those that seek others to solve their problems for them... usually don't last long in business.
I've witnessed many firms run the gauntlet with varying levels of success, and would suggest the following:
1. sell what the customer already wants, as people with loss aversion stick with what they already know.
2. sell what makes customers feel good buying, and reward them with actual functional utility in their life
3. Never compete, focus on service with a novel niche product. Stupid people by their nature destroy everything around them regardless of long term benefit.
4. Never hire people unless absolutely necessary, and contract with tax responsibility clauses when possible.
5. Never buy equipment unless absolutely necessary, or lease when possible
6. Never enter legal or subscription agreements even with your own legal specialists feedback
7. Never become a poser burning $170k/month on labor in a vestigial office
8. Position your firm to leverage tax and grant programs
9. Stay quiet (especially online in a sea of cons), and only talk about the distant past when people try to goad you into telling them how you make revenue
10. Avoid bums in suits as many are dangerous well practiced thieves. Never let technical staff talk with the customers, or vendors. Some people go crazy when they see a bit of money, and do not behave rationally.
11. There must only be 1 president, and all agreements must be in contract form.
12. Never risk more than 15% of annual revenue on ANY deal. Customers lie and disappear on rare occasion... Large firms can grab your firm like a dog with a rag doll, and may still stiff you on the contract knowing the legal and fiscal power asymmetry
13. Chasing customers means your business model still needs work. If people are happy with what you are providing, than growth should naturally happen every year
14. Go to trade shows to see what other people are selling, and ask yourself what else does the customer need
15. Cash is king, as long as the money flows most other problems are irrelevant
Best of luck, =3
Re: My eighth year as a bootstrapped founder
#30Maybe it's just me, but it seems kind of weird to say you earned $8,200 in "profit" when there was no salary. Profit is typically the excess a business earns above its costs. For a solo founder, it can be a little tricky because the more you pay yourself in salary, the less you have in profit (and vice versa). But here, there was no salary. Maybe "earnings" or "income" would be a better term to use? Otherwise someone…
Yea. Perhaps a better metric to use would be Seller's Discretionary Earnings (SDE) which includes the owner's salary, benefits, and discretionary expenses, after adjusting for non-recurring, non-operating, and non-cash items. This metric is often used when one person wants to acquire another business.