Sunday Reads, Watches and Listens - YouTube The Learning Machine and How To Fumble A Billion Dollar Opportunity

Good morning if you are not a Leafs fan…

That was tough last night watching the Leafs lose again in game 7, in overtime, but it was a great hockey game.

After the game, we watched the two-part Steve Martin documentary on Apple TV and it was fantastic.

I was that young kid that listened to his comedy albums and loved the silliness.

Steve walked away from comedy at the very top of his game in 1980 for a movie career which has not gone too badly 🙂 .

I think silliness and comedy is headed into a massive boom…see ‘Conan O’Brien Needs A Friend’ podcast, ‘Hot Ones’ on YouTube (Conan had a hysterical episode as well).

The boom in comedy is tied to YouTube and I am hoping to be accelerated by our own Social Leverage investment in Punchup.live.

Speaking of YouTube, my friend Trung Phan has an awesome Saturday post up titled ‘YouTube: The Learning Machine’. Trung offers up many examples of how the best athletes in the world across almost every sport are both learning and educating on YouTube.

I have seen it in golf and I know if I had the time or inclination I could rapidly improve my game.

YouTube has been great to me from day ONE, inspiring me to leave the hedge fund world to start Wallstrip in 2006 (which CBS acquired). Sadly CBS has pulled all 500 episodes from YouTube which is very upsetting. I get emails all the time from people asking me what happened to episodes they want to share including my own kids Rachel and Max.

I am personally investing my time once again on YouTube building ‘Trends With Friends’ …please subscribe… and of course also thinking through a strategy for Stocktwits.

Trung’s Saturday newsletter is always great. He also linked to a 2020 Danny Meyer interview on Invest Like The Best where Danny talks about the ‘power of hospitality’. Danny started Shake Shack whose stock is still doing pretty pretty good.

One more today, but a good one for both entrepreneurs and investors. It is titled ‘How Substack Fumbled a Billion Dollar Opportunity. And How To Avoid Doing The Same. Social Leverage was the seed investor in Beehiiv (a competitor) so of course I have a special interest in this story and potential case study. I sit on the board of Beehiiv so I have watched a lot of this go down and strategized many times with Tyler, the founder.

I believe the best way to not fumble ‘billion dollar’ opportunities, is to stop thinking you are building one (at least from day one). It all starts with the cap table which too few founders think about enough at the earliest of stages. I dove deeper into this last week in my newsletter with ‘Momentum Is Fragile’.

Have a great Sunday.