This is Bootstrapping (to me)
What exactly do I do each day?
Whether you call your flavor of entrepreneurship "bootstrapping", or "indie hacking", or "side hustling" or just, "starting a business", I bet your job description is pretty different from mine.
Good. It's supposed to be different.
So if "you do you" is all there is to it, then what's the point of even asking myself, "what is it that I do??"
Here's why I spend a lot of time thinking about this:
I need to know that I'm doing a good job. But nobody's here to manage me or give me a performance review. So it's on me to evaluate how I'm doing at my job.
Is my score card is my bottom line? My revenue graph? How many customers I have? For a while, that was my measuring stick.
But that's not it. Financial success is a goal. An outcome. But it doesn't tell me how I'm doing.
Am I doing this right?
So I know that there's no right or wrong way to do my thing as an entrepreneur. But I still want to know if I'm doing my thing well.
Am I improving my batting average? Or just taking more swings?
Am I going somewhere? Or just spinning my wheels?
Am I getting stronger? Or just getting tired?
Measuring my performance
Call me old-school, but I still call my flavor of entrepreneurship, "bootstrapping". The term, Bootstrapping, means different things to different people.
Here's what it means to me. I see it as a cycle:
- Build
- Delegate
- Manage
- Repeat...
That last step—repeat—is my key performance indicator.
If I don't reach that step, then I got stuck somewhere on the first 3. But if I make it past the first 3 stages, then I built something that freed me up to build the next thing.
To me, that's growth. If I'm able to spend most of my time building—then stacking and cycling back to building again—then I'm doing well.
And no, not everything I build has to be a financial success—even if that's the goal. If it doesn't pan out, I can still pocket the byproducts and cycle back to build again. Even the best hitters in the game only reach base 3 times for every 10 at-bats.
Let me break down my work—my cycle—as a bootstrapper:
Build
At my core, I'm a builder.
To bootstrap a business is to build it with my bare hands. Getting deeply involved in every detail. Every decision. Considering every angle.
Designing. Redesigning. Prototyping. Launching. Listening. Learning. Refining. Reworking. Extending. Subtracting. Optimizing.
In the beginning, it requires creative energy. Builder energy. My energy.
Eventually (hopefully) it's successful enough to need less creative energy and more sustainable energy. That's my queue to shift gears and enter stage 2 in my cycle.
Delegate
When the success of my thing depends on repeatable tasks in order to sustain, then my job must change.
My task changes from "how do I build this thing?" to "how can this thing still work when I'm not around?"
It's a challenging puzzle. I like it. Not as much as I like building new. But I still like the complexity of assembling systems to be able to fire and replace myself.
Delegating is hard because it usually means slowing down in order to speed up. Building systems takes time. Training and coaching your replacement takes time.
You could certainly do it faster yourself. But then you'll never get past step one. You won't grow. Bootstrapping, to me, means building and then delegating so that you can get back to building the next thing.
Managing
From what I can tell, the management phase is where I personally feel the most different from other entrepreneurs that I know.
I often feel like I'm missing something or I'm doing it wrong. Maybe that's true...
But if I'm honest? I wouldn't change a thing.
I don't have 1-on-1 calls. No weekly standups. I don't track anyone's time. I don't even spend much time closely examining or monitoring my team's work—until they ask me to.
We communicate and collaborate—deeply and frequently—but we do it 100% async. We ship stuff faster than most other teams I know. We deliver great products. Our trains always run on time. I 100% trust my teammates' judgement. And they trust mine.
Nearly all of my teammates have worked with me for multiple years. Some even returned to with me across multiple businesses. Our headcount never exceeded 25 (it's currently 7). Most are part-time retainers, some full-time. I never missed a payroll or paid late.
But I'm often jealous of my friends' businesses that are financially successful enough to afford to fly out their teams to fun locations for annual team retreats. I'd love to build a small company culture with perks like that. Maybe someday.
For now, I'm happy with my bootstrapped, profitable, calm, and focused management style. We're just a crew of high-caliber, no-nonsense, professionals. Doing what we do, day in, day out.
I've had highs and lows in m journey as a bootstrapper. But I think I'm doing a pretty good job right now, because I'm sticking to doing what I do, how I do it.
Bootstrapping. Building. Cycling.