I went through an IPO. Joined the company early enough that I made enough for 15ish years if I continue my same lifestyle. Prior, entrepreneurship has been my passion. Founded 3 startups in the past with zero to small success, but nothing life changing until this IPO.
Journey to IPO is not easy. Culture and values are no longer the same. It's not a surprise. Different culture / values is fine, but they declined in my POV. I did manage to survive & adapt, to see it through IPO, as a means to buy financial freedom. It also taught me a lot about perseverance. There is not much left in the company that aligns with my values or principles. Probably I hit the peter principle[1].
Compared to my younger self, now I have 2 daughters. As an immigrant to bay area, never got a chance to truly take a break between the jobs. My passion for entrepreneurship is still there. I truly want to give it enough shot either to build something meaningful or prove to myself that it's the game I no longer enjoy.
Currently my plan is to
- quit the company by figuring out alternate means for immigration
- put aside money for 1.5yrs
- for at least 3 months, be the househusband and nothing else: daily home & kid chores (like a stereotypical housewife); focus on physical fitness
- after 3 months, start scoping out next venture
- keep trying and failing until i land on a financially feasible idea. have a large network and potential co-founders
At a high level I thought I would cap my adventure to 1year. On the other hand, I'm very confident that as long as I fail and learn and evolve, I will be able to start decently successful company (even a $15K per month revenue generating idea like indiehackers), if given enough time. That makes me wonder what is stopping me from giving myself 5 years instead of 1 year.
I know it is going to be a very thrilling journey and also tough at times. My prediction is that it would get very hard at around 6 month mark. But there is something about this journey that keeps driving me forward.
When I think about this startup journey, knowing that it's a financially bad decision, I often think why I' keep getting attracted. I think Michael Seibel summarized it the best[2] about why/who should start a startup: "there is a certain type of person who only works at their peak capacity when there is no predictable path to follow, the odds of success are low, and they have to take personal responsibility for failure (the opposite of most jobs at a large company)". Every time I read it, it feels like he described me. Hopefully all the failures in my pocket, 'wisdom' and lessons learned would come to rescue.
[1] https://en.wikipedia.org/wiki/Peter_principle
[2] https://www.michaelseibel.com/blog/why-should-i-start-a-star...