As I've transitioned out of founder life, I've started to think about what I would want to do next. If I was to start another company, what would it be?
After building a traditional B2B SaaS platform (it was open source so maybe not super traditional, but we did have a cloud offering), I feel pretty confident in saying that I don't want to build another B2B platform.
If we're being honest, building B2B feels a little soulless. The crazy part is that it didn't even really feel like that until we started to shut the company down after we got acquired. I remember telling our customers and they essentially said, "cool, sounds good.".
These were customers that we spent years trying to get (and many of them were insanely demanding) and at the end of all of that they just didn't really care. It was almost like breaking up with your girlfriend and there is a part of you that wants them to fight back and cry just so you can feel wanted, but they never do. They just say "okay."
It was weirdly anti-climactic and sprouted this idea in my mind that, despite what B2B customers say, most just don't really care that much because at the end of the day, for most people, work is just work. Business software is just business software. It's actually as boring as it sounds.
That's all to say that after three years of starting, running and exiting a startup, I still feel a sense of emptiness. Like I didn't really bring any value into the world. Maybe it's ego, maybe it's some deeper psychological issue (it's probably both), but whatever is next, I really want to make an impact in people's lives and do my life's work.
So that got me thinking. If I want to make a positive impact in as many people's lives as possible, I have to do something big. I want to do something big. I think I have an even bigger chip on my shoulder than I did before.
As I started to think of big ideas to work on, I asked myself, "why didn't I just do a big idea in the first place?" After thinking about that for a while, I came to the conclusion that I hadn't earned the right to go after a big idea. As if I had to prove myself with a "traditional" business first before I could take a crazy shot in the dark at something big.
Why did I think this?
A pattern that I've seen is that a founder/founding team will work on a "traditional" startup, usually some sort of B2B SaaS business, and then after an exit will take a moonshot. Something highly improbable but usually fantastic.
Elon did Zip2 then X/Paypal and then went for SpaceX and Tesla. Sam Altman did Loops then Openai. Brett Adcock did Vettery and then Archer and Figure. Travis Kalanick did Red Swoosh and then Uber. The list goes on.
At some point, I think I internalized this and convinced myself that I needed to follow the same playbook. Maybe it was because I didn't go to Stanford or have a PHD, but I think I convinced myself that I wouldn't be able to raise money for a moonshot because, well, why would any VC fund a nobody?
On one hand, there is somewhat of a pattern there and on the other hand, there are certainly many founders that just go for it. But which path has a higher probability of success?
Is there an entry price that you have to pay i.e. starting a traditional business and getting an exit, in order to convince investors that you're capable and that you're more likely to succeed than somebody who hasn't done it before?
Elon likely couldn't have done Tesla and/or SpaceX if he didn't have the Zip2 and Paypal proceeds to invest in those companies. Just given the nature of those companies - hardware, capital intensive, long time horizons, I think it's unlikely any investor would have given him the money he needed if hasn't been a founder and wasn't personally investing.
Could Sam Altman have become the President of YC and then start OpenAI if he wasn't initially a founder? I think so. Sam is widely regarded as charismatic and agentic. He probably would have found himself in the right circles at some point in time. But I do think being a founder and going through YC certainly accelerated the process.
At the same time, I'm not sure if those people ever actually thought of it that way? I think they just did what they wanted to do at that moment in time and then thought about what was next.
Maybe I'm overthinking it.