Most people, including me, would be better off if we gave up on being smart and stuck with a simple approach: long-term holdings of diversified, low-cost index funds, using only money we can afford to tie up for years.
Eventually, I ran out of money and started to seek VC funding. I had a working product, and customers using it, and everyone said no. Meanwhile, I watched other people who fit a different “profile” get money thrown at them for shitty ideas…The only thing I could attribute it to was that I was black…The whole experience made me hate raising money. But it forced me to become resourceful, scrappy, and maniacally focused. I learned how to stretch each dollar. Today, I’m very grateful. The business is approaching $30 million in recurring revenue, and growing more than 100 percent year-over-year. It’s been profitable since 2016. And I’m the majority owner.< Calendly founder Tope Awotona>
I am learning a new skill this summer aka driving (don’t ask me why it has taken me so long to learn driving) and I have never felt more of a fool at something like I have these days. It reminded me of this quote by Mortimer Adler in How to Read a Book on how learning a new skill (driving for me and skiing in his example) can make you feel like a fool: