Bootstrapping vs. Venture: Lessons from My Journey(medium.com)
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Bootstrapping vs. Venture: Lessons from My Journey
https://medium.com/@citizenblr/bootstrapping-vs-venture-lessons-from-my-journey-d383524e57bd
6 comments
I guess my only question is how do you keep yourself from going broke while starting these projects. I've a chance to do some great work now, but it would lower my pay beneath what I can live on.
Oh, that’s a very good and difficult question. I’ve broken down many times myself and still go through tough periods. Maybe over time you just grow a bit thicker-skinned. But I can really imagine how hard it feels when you’re just starting out.
To be fair, though, it’s not necessarily easier in a venture-backed startup — maybe even harder. On top of the project risks and challenges, you also have to deal with investor pressures.
If you’re interested in diving deeper into this topic, I’d be happy to share more — but maybe if your question is a bit more detailed or specific.
To be fair, though, it’s not necessarily easier in a venture-backed startup — maybe even harder. On top of the project risks and challenges, you also have to deal with investor pressures.
If you’re interested in diving deeper into this topic, I’d be happy to share more — but maybe if your question is a bit more detailed or specific.
My position is that I've been in a failing start-up for years. Public company, but has burned through all their investment and has reached its ending days spiral. Small amount of equity has declined to be worth next to nothing, passion for the work has declined, both myself and more broadly.
On a week of vacation leave, I went and helped an extended family member in their home business. It combines the best aspects of my past three jobs. High tech, optics, design and manufacture, it's hard, and it's fascinating. There's a clear path to profit, with demand. Might be weeks, might be months, but in the meantime I can't make enough to cover my costs.
I can't risk my family's security. Having loved out of my car while studying, despite over a decade passing, the memory is fresh.
A pay cut would be fine, worth it, but the risk feels so high.
On a week of vacation leave, I went and helped an extended family member in their home business. It combines the best aspects of my past three jobs. High tech, optics, design and manufacture, it's hard, and it's fascinating. There's a clear path to profit, with demand. Might be weeks, might be months, but in the meantime I can't make enough to cover my costs.
I can't risk my family's security. Having loved out of my car while studying, despite over a decade passing, the memory is fresh.
A pay cut would be fine, worth it, but the risk feels so high.
Let me try to share my story briefly.
None of my ventures ever came with guarantees. I started out working in an IT company, growing quickly in both salary and career, but I didn’t stay long — I soon decided to start something of my own. I was young, without a family or obligations, not yet used to the comfort of a steady job. It was easy to take risks, and I wanted responsibility.
I founded my first company making calls to clients from my car. Instead of an office, I sat in a small room with rags on the windows instead of curtains, cheap computers, and desks that looked more like school tables. I was the manager and the HTML coder, the recruiter and the cleaner — finding projects, fixing mistakes, talking to clients, and handling all the operations. Looking back now, I smile — but it was completely irrational.
Later, when the company was doing well with outsourcing and even serving a large public client, we made another “irrational” decision. We handed a big, profitable project over to their in-house team and switched to building our own product. People thought we were crazy. But we were burned out. We wanted to create something of our own, even if it meant working harder. There was a certain romance in that, and a belief in ourselves. I still remember how we celebrated our first $50 product sale more than a $50k invoice from an outsourcing client. Strange, right?
The product grew — not quickly, but it did. And when growth stopped, we tried again. Another product, and another. If it was interesting, we continued. If not, we shut it down or simply moved on. Each new start was slower and harder!
But the important nuance is that we always had some buffer. We started our first company while still employed, only leaving once we had our first client (for 1–2 months we worked two jobs). We switched to our product only after it could at least cover the minimum salaries (working in parallel for 6–12 months). We launched new products only when the main one could support us, when we could reinvest profits, and when our personal lives were at least somewhat stable. We worked hard, but we always tried to keep a margin of safety. Living in a car was never on the table — worst case, we could always go back to a job or take another outsourcing project. There is a right time for everything.
I’m not giving advice — just sharing my own path. Even now, when something doesn’t work out, I look for the next idea to keep myself busy and moving. I always try to hedge risks with something new, rather than stagnating in one place.
None of my ventures ever came with guarantees. I started out working in an IT company, growing quickly in both salary and career, but I didn’t stay long — I soon decided to start something of my own. I was young, without a family or obligations, not yet used to the comfort of a steady job. It was easy to take risks, and I wanted responsibility.
I founded my first company making calls to clients from my car. Instead of an office, I sat in a small room with rags on the windows instead of curtains, cheap computers, and desks that looked more like school tables. I was the manager and the HTML coder, the recruiter and the cleaner — finding projects, fixing mistakes, talking to clients, and handling all the operations. Looking back now, I smile — but it was completely irrational.
Later, when the company was doing well with outsourcing and even serving a large public client, we made another “irrational” decision. We handed a big, profitable project over to their in-house team and switched to building our own product. People thought we were crazy. But we were burned out. We wanted to create something of our own, even if it meant working harder. There was a certain romance in that, and a belief in ourselves. I still remember how we celebrated our first $50 product sale more than a $50k invoice from an outsourcing client. Strange, right?
The product grew — not quickly, but it did. And when growth stopped, we tried again. Another product, and another. If it was interesting, we continued. If not, we shut it down or simply moved on. Each new start was slower and harder!
But the important nuance is that we always had some buffer. We started our first company while still employed, only leaving once we had our first client (for 1–2 months we worked two jobs). We switched to our product only after it could at least cover the minimum salaries (working in parallel for 6–12 months). We launched new products only when the main one could support us, when we could reinvest profits, and when our personal lives were at least somewhat stable. We worked hard, but we always tried to keep a margin of safety. Living in a car was never on the table — worst case, we could always go back to a job or take another outsourcing project. There is a right time for everything.
I’m not giving advice — just sharing my own path. Even now, when something doesn’t work out, I look for the next idea to keep myself busy and moving. I always try to hedge risks with something new, rather than stagnating in one place.