Why Buying More When Odds Shift Wins Big

Chris Sacca is an investor and founder of Lowercarbon Capital and Lowercase Capital.

Prior to becoming an investor, Chris grew up in Buffalo, NY; studied around the world by way of the Georgetown School of Foreign Service; turned his student loans in $12M in the tech bubble of 2000 before losing it all and then some; and broke into Silicon Valley before eventually landing at Google, where he won the founders award. Then Chris started angel investing, which led to his first venture fund, Lowercase I. Lowercase I is one of if not the best performing VC funds ever, by multiple, at 214x, and included Twitter, Uber, Instagram, and more.

Toward the end of Lowercase, I had the pleasure of working with Chris. Around that time, he was also a Guest Shark on Shark Tank. Chris was heavily involved in both Obama campaigns and was a large supporter of Hillary Clinton in 2016. When Trump won, he wound down new investing at Lowercase and "hung up his spurs" to focus on political and democracy related efforts. Then, in 2018, Chris started Lowercarbon Capital to invest in "un-f*cking the planet": carbon removal, climate science, cooling the planet, and eventually nuclear fusion.

We talked about writing and storytelling, keeping people around who keep you honest, having a good taste in "weird," playing rigged games, taking the right kind of risks, and how even billionaires have imposter syndrome. We also get into how great founders embody inevitability, what makes the people at Lowercarbon special, how much Chris thinks about AI, and the many chapters of Chris's life, including whatever might be next.

Authenticity is a moving target for all of us, but one of the things I most admire about Chris is his ability and desire to shamelessly play his own game.
Timestamps:

• (0:00): Open: The Common Thread Amongst The Best Founders
• (1:20): Intro
• (3:42): Coast to Coast
• (12:29): Leaning into Weird & Investing in Fusion
• (24:35): Having People Who Keep You in Check
• (32:00): The Power of Language and Stories
• (1:03:03): Investing, Risk, and Wild Confidence
• (1:27:57): Imposter Syndrome and Making Companies Better
• (1:38:03): Lowercarbon's Team and Culture
• (1:57:47): Chris's Life Chapters, AI, and Creative Outlets
• (2:22:04): Drifting Back Towards Real

All links and transcript available at https://dialectic.fm/chris-sacca

Dialectic with Jackson Dahl is available on all podcast platforms.
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