Paying yourself. When, how much, and the guilt.

The messy truth: we funded the product with a second business

The early days were complicated and, frankly, messy — and I think the honest version is more useful than the clean one. To build the product, my business partner and I both needed additional income. We had consulting gigs to cover our mortgages. And we stood up a separate little marketing agency with a client or two that paid some bills in the days when the product had no revenue at all. So there were actually two companies: a consulting/agency business and the product company, PipelineCRM — two LLCs, two bank accounts.

For the first couple of years, the consulting revenue was what kept us fed and what we used to invest in the product. We weren't starving, but the income was only enough to take small distributions and pay our 1099 contractors. It didn't get cleaned up until we landed our first large customer and could finally see real product revenue — not much, but something, and enough to start paying ourselves from the business we were actually building rather than the consulting work propping it up. The moral isn't "do it this way." It's that you do whatever is necessary and legitimate to build and invest in the business, and in the early days that's rarely tidy.

How we set the number: equal, and what we could afford

Once the product could pay us, the "how much" was simpler than people expect. We paid ourselves the same, and we set it based on what the business could afford — full stop. It certainly wasn't market rate; we'd both been in Director and VP-level roles before starting the company, earning considerably more. The number was a function of the business's reality, not our résumés. Paying ourselves equally took a whole category of friction off the table between co-founders, and tying it to affordability rather than ego kept the comp honest.

The guilt the title promises? We didn't really have it.

Here's an honest twist on the premise: we never really agonized over paying ourselves. When things were going well and we had a cash surplus, we'd simply agree to take an additional distribution. We didn't spiral into "but what if we kept it in — how much better off would we be?" We just balanced taking home a fair wage against reinvesting, and accepted that there are real trade-offs either way. I think the reason there was no guilt is that we'd internalized the trade as fair: we were underpaying ourselves relative to market for years, so taking a reasonable wage — and the occasional surplus distribution — wasn't indulgent. It was the deal. If you've set a deliberately below-market salary, you've already earned the right not to feel bad about it.

The later years: harvesting profits

The relationship with money changed in the later years, and this is where bootstrapped profitability really pays the founder. As an exit started looking less likely given our growth, we made a deliberate decision — with our board, who were fine with it — to start harvesting profits. Increasing profitability became an engine for additional distributions, which finally moved our total comp toward something closer to a fair market wage.

That's the optionality a profitable business buys you: you don't only earn by selling someday: you can take money out along the way and reinvest or earn on it. A profitable bootstrapped company means you start meaningfully benefiting from ownership while you're still running it, not just hoping for a payday at the end. The salary keeps you whole; the profits are the actual return on the bet — and you can begin collecting that return years before any exit, if there even is one. (It's the same optionality I'd argue lets you raise or sell from strength rather than need.)

Getting it right is personal — there's no universal formula

I think we got founder comp mostly right, but I'd be wary of anyone offering a clean formula, because it's a deeply personal decision between founders. The right number depends on the founders' actual lives, not a spreadsheet. Are there mortgages? Kids? A sick or elderly parent to care for? Those realities make "do we take $X out or keep it in?" anything but straightforward. Two founders in different life situations may genuinely need different things from the business, and pretending it's a purely financial optimization misses how much of it is personal circumstance. The conversation has to account for that honestly, or the resentment shows up later.

The reframe that makes it all make sense

If I had to give a bootstrapped founder one piece of advice on their own pay, it's this. Agree on a minimum — usually a below-market living wage, somewhere in the neighborhood of $125K–$150K. That's the range that makes sense for most founders: enough to live and not resent the business, low enough to keep fueling it.

And then the mindset, which is the part that matters most. If you go into this expecting to earn the $250K–$350K you made as a VP at a mid-sized company, and you feel wronged that you don't, you need to change how you're thinking about it. You're making a trade and a bet on yourself: you under-earn in the short and medium term in exchange for a large ownership stake, betting that in the long term you'll earn far more from the equity than you gave up in salary. Founder pay isn't a wage you're being cheated on. It's the premium you're paying to own the upside — and if the business works, the equity makes the math look obvious in hindsight. Resent the salary and you've misunderstood the deal you signed up for.