1/We’re thrilled to share the news that @Riskalyze has been recapitalized by @HgCapital, one of the world’s leading software investors with $37B under management. This is a huge step forward for the Fearless Investing Movement. https://t.co/yOVEbmDDqP

— Aaron Klein (@AaronKlein) August 25, 2021

Aaron announced this today on Twitter so I guess it is okay to blog about it. I was an early investor in Riskalyze. As I was trying to build my street cred as a solo investor, I built a syndicate for Riskalyze and we invested. It paid off.

The whole story isn’t so simple. I met Aaron in NYC at Fred Wilson’s beer blast. It was Fred’s 10th anniversary party of his blog, and he invited some people who interacted with his blog. I met Andy Swan there, who became a Riskalyze board member. I met Donna Brewington White there, who became a talent agent for Riskalyze. I met Arnold Waldstein there who also invested. RIP Arnie, I know you are smiling.  Arnie and I didn’t agree on politics, but we agreed on Riskalyze and Aaron.

For some background, I took Professor Scott Meadow’s class at Chicago Booth on PE/VC. When he teaches that class, he tells a story about passing on Starbucks not once, but twice.  He passed because of valuation, and because he wasn’t getting preferred.  I always remembered the Starbucks story.  It didn’t hit home because of the lost opportunity.  It hit home because in investing, you have to be objective on each (Read more...)