32: Chris Sacca - Drifting Back to Real
Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
Podcast Summary
In this two-and-a-half-hour conversation, legendary investor Chris Sacca returns to discuss his journey from venture capitalist to climate investor, sharing insights on risk, authenticity, and building companies. (02:30) Sacca, founder of Lowercase Capital (achieving a 214x return) and now Lowercarbon Capital, opens up about his evolution from early-stage investing in companies like Twitter, Uber, and Instagram to focusing on climate technologies including nuclear fusion. The episode explores his philosophy on taking calculated risks, the importance of surrounding yourself with people who challenge you, and why he believes the best founders embody "inevitability" - never considering failure as an option. (39:48) Sacca also discusses his approach to storytelling, the power of language in business, and his thoughts on the current generation's relationship with risk and agency.
- Main themes: Risk management, authentic leadership, climate investing, the power of storytelling in business, and navigating multiple life chapters while staying true to core values.
Speakers
Chris Sacca
Chris Sacca is an investor and founder of Lowercarbon Capital and previously Lowercase Capital. Lowercase I achieved a legendary 214x return and included early investments in Twitter, Uber, Instagram, Docker, and Blue Bottle Coffee. Prior to investing, Sacca worked at Google where he won the founder's award and managed multibillion-dollar budgets including wireless spectrum strategy. He was also a guest shark on Shark Tank and has been heavily involved in political campaigns. After "hanging up his spurs" from traditional venture investing in 2017, he launched Lowercarbon Capital in 2018 to invest in climate technologies including nuclear fusion, geothermal energy, and carbon removal.
Jackson Dahl
Jackson Dahl is the host of Dialectic podcast and previously worked at Lowercase Capital early in his career. He focuses on long-form conversations with founders, investors, and creative professionals, known for his thoughtful questions and ability to draw out authentic stories from his guests.
Key Takeaways
Successful Founders Embody "Inevitability"
The single trait Sacca identified among all his most successful founders is that failure simply wasn't an option in their mental framework. (39:48) When he first met Instagram's Kevin Systrom and Mike Krieger, they casually mentioned features "for when we get to 10 million users" while meeting in a co-working space as a two-person team. Systrom wasn't trying to sell Sacca - he genuinely knew Instagram would reach massive scale. This inevitability mindset separates legendary founders from those who hedge their bets by preparing for failure scenarios.
Surround Yourself with People Who Challenge You
Success creates a dangerous isolation where fewer people are willing to call out your mistakes. (25:35) Sacca credits his wife Crystal as someone who consistently challenges his thinking and calls out his blind spots. He observes that many successful leaders who go "off the rails" invariably have no one around them who can say no - everyone becomes either sycophantic or opportunistic. The Collison brothers maintain their edge by keeping each other honest through constant dialectic debate.
Develop a Taste for "Good Weird"
The biggest alpha in investing comes from backing founders who seem unusually ambitious or unconventional to others. (12:29) When team members reported that Augustus Doricko (Rainmaker) seemed "too big for his britches" with crazy ambitions, Sacca immediately sent them back, recognizing that normal people don't generate extraordinary returns. He's learned that strong negative reactions to founders often signal exactly the kind of contrarian bet that leads to massive success, whether in cloud seeding or nuclear fusion.
Use Language as a Strategic Weapon
Mastering storytelling and metaphor can be more powerful than technical expertise in business. (32:00) Sacca learned this lesson watching a prosecutor destroy his legal case with a simple combination lock metaphor, despite having the technical facts on his side. He studied cowboy language and colloquialisms to become more effective at making complex ideas accessible. Great metaphors and analogies can be "weapons of mass destruction" in shaping how people think about problems and opportunities.
Play Games You Can Control
Focus your energy on areas where you can actually impact outcomes rather than hoping for lucky breaks. (63:02) Sacca describes venture investing as "rigged" in his favor because he can actively make companies more successful through his involvement, unlike public markets where he has no influence. This philosophy extends beyond investing - he only takes calculated risks where his actions can meaningfully improve the probability of success, whether through relationships, expertise, or strategic value-add.
Statistics & Facts
- Lowercase Capital Fund I achieved a 214x return, making it likely the best performing venture fund ever by multiple, with investments in Twitter, Uber, Instagram, and other iconic companies. (01:36)
- By Twitter's IPO, Sacca and his partners owned approximately 15.8% of the company after systematically buying shares from other investors who didn't believe in the platform's monetization potential. (77:41)
- Lowercarbon Capital now manages over $1 billion across eight different nuclear fusion companies, representing four different technological approaches to achieving commercial fusion power. (21:03)
