I have been preparing to become a founder since 2016. In 2021 I co-founded my first startup. In 2024 the company is well on it’s way to $1 million in ARR though whether it succeeds remains to be seen. The company is still in business
My primary objective was to validate myself as a founder and secondary objective was to create a success to lever into the next startup.
Overall, I achieved my primary objective, as for the second, TBD though in Q2 2024 it has 10x’d it’s ARR.
Things I did right
- I became an excellent engineer and manager. A company is merely a diluted extension of you. Your excellence therefore determines the companies excellence.
- I prepared by studying prior founders years in advance — key resources are Steve Blank’s work and YC’s materials.
- I’m glad I focused on execution and reduced product risk by tackling a known market and partnering with a venture studio before going to blue ocean. It let me isolate execution/operation related skills.
- I trained my team to operate without me so that I could help the business where it needed me most or preserve the optionality to depart.
- I relentlessly clarified what winning meant
Things I could improve
- I hired too fast and fired too slow. The first month will tell you how the next six months will go. Don’t wait, don’t do a pip, if you have to repeat yourself that is a red flag. If the founding employees don’t want max equity, that is a red flag.
- I hired for experience (in a few cases) instead of for growth mindset and that was a mistake. Growth mindset and adaptability first — then experience as a bonus.
- I accepted bad deal terms for my equity with the company — primary goal aside, I could have gotten better terms.
- I didn’t give candid enough feedback rapidly enough. While I challenged my team and helped them grow, I could have done more sooner. I did get feedback that no other manager had been so challenging and helped them grow as much but I feel this is a low bar.
- I let core functionality be throttled by a third party. I let the nervousness of others lead me to outsource a piece of core functionality to a third party vendor. This was a huge mistake that slowed our iteration speed, led to outages, and other pain points.
Final Worlds
The experience was validating. When your judgement is sampled hundreds or thousands of times against reality with nowhere to hide — you know it is good (or not).
I was shocked at how The Competition is Weak. Most founders are completely unprepared for the job. The years of deliberate and methodical preparation put me far above first time founders based on:
- solicited feedback from the studio and investors
- indirect observations of hundreds of first time founders through the studio
Even among would-be founders, the ability to act out decade+ plans seem to be less than 1 in 100. It seems many founders don’t read the canonical textbooks or coursework from other successful founders — baffling.
Then again, I am pre-disposed to long term planning — I have yet to meet a single person who estimated their date of death based on epigenetic pace of aging and allocated accordingly.
Regardless, I’m vetted and ready. Full steam ahead for The “Rocketship” Era — Going Big on Startup v2.