We got our headshots taken today. Kim, Niki, and me, out by the office, the three of us standing around while a photographer we paid to be there told us where to look. I’ve been thinking about that all evening. Not the photos (I hope those turned out). The fact that we hired someone at all, on what is essentially day one of this thing.
I’ve been thinking a lot about how different this business feels from our first one. People might assume Start Small Farms is bootstrapped. It isn’t.
What bootstrapped actually meant for us
Kim and I have done this before. We started Stranger Studios in 2006 and launched Paid Memberships Pro in 2011. That was bootstrapped in the truest sense of the word. There was no cushion. Every dollar counted, and we had to make money on day one, because there wasn’t any other money coming. The business had to feed itself from the very first week or it wasn’t going to exist.
When people say “bootstrapped,” that’s what they usually mean: no outside money, no runway, make it work now. And that was our whole reality for a long time.
What self-funded means
Start Small Farms is different. It’s self-funded. On day one, we’re already spending. We paid a photographer to come to our home base this evening. There’s inventory stacked in the office waiting to become gift boxes. We’re hiring people. We’re building things that won’t pay us back for a while, if they ever do directly.
The money for all of that is coming from us. That’s the distinction I want to make here: bootstrapping is about not having the money and making it anyway. Self-funding is about choosing to put money you already have into something before it’s proven. Those are not the same, and I don’t want to blur them just because “bootstrapped” sounds scrappier.
The part I can actually feel
What I can feel in it is the privilege. And I mean that plainly, not as a humblebrag.
Some of it is the money, sure. But the bigger piece is the permission it buys. Permission to fail. Permission to take longer than we planned. Permission to pivot if the direction we thought we were headed turns out to be wrong. When a business has to make money on day one, it doesn’t get to do any of that. It has to be right, fast. A self-funded business gets to keep going anyway, and keep figuring it out.
That’s a real gift, and a big reason “start small” is even possible for us right now. We get to start small on purpose, not because we’re forced to.
The other thing we’re bringing
There’s another thing we’re carrying into this: experience.
Kim and I have made the mistakes already. Over and over, for almost twenty years, while raising two kids, buying half of another existing business, and more shenanigans only two crazy in love high school sweethearts can weather.
We know what it feels like to overbuild something nobody wanted, to hire at the wrong time, to spend on the wrong thing, to sleep too little and worry too much.
The money we’re putting into Start Small Farms? We do it with a lot more confidence and a lot less fear than we had the first time around.
That confidence is worth as much as the cash, honestly. Maybe more. It’s the difference between spending money and being scared the whole time, and spending money because you’ve seen this movie before and you know roughly how it goes.
Grateful, and saying so
I don’t want to pretend this is harder than it is. A lot of people build businesses with no safety net and no prior experience, and they do it anyway. That’s the truly hard version, and I have enormous respect for it.
We’re in a different spot, and I’d rather name it than dress it up. We’re lucky. We get to start something with a little money behind it and two decades of scar tissue to draw on. That’s worth being grateful for, and it’s worth being honest about.
So that’s where my head is tonight. Feeling grateful. Feeling the privilege of getting to start small on our own terms. And genuinely hoping those photos turned out.
— Jason