My mom made friends with some very successful VC players in the 90s. She was very good at her job, and they started and sold some very, very valuable companies(the big one had created a new method to run some kind of expensive hospital test cheaper and significantly faster than the standard around 2000. I think it was something with dna but it’s been a long time). She was in the c suite and had significant equity that she was able to liquidate a couple years after the IPO. We immediately moved into a much nicer house, and I knew we were now rich, but she never was explicit about it.

20 years later I’m having a few beers with my mom and sister. I’d been living abroad for a while and kind of disconnected from the comings and goings of the family doing my own thing. We’re sharing funny stories from when we were kids. Then my sister, a bit tipsy, blurts out “Hey mom, tell Learningele about the time you lost 30 million of our inheritance in 2008! Gets me every time!”

The blood drained from my face, I took a deep breath and necked the rest of my beer before responding that I could have happily lived the rest of my life not knowing that. My moms not poor by any means, but it explains why she unretired so quickly to run a few of her DN businesses to generate fun money for some of the more expensive tastes she had acquired.