Jan 20, 2022 · 1h 24m · news
Chris Sacca's True Unfiltered Opinion on Facebook and Softbank | Full Interview · 20VC with Harry Stebbings
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this extensive interview on The 20VC Show, legendary investor Chris Sacca shares hard-earned lessons from his venture capital career, the philosophy behind his climate-focused fund Lowercarbon Capital, and his perspectives on wealth, parenting, and corporate ethics.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 8.1% of the talking time here. How this is scored →
Harry as informed peer 4.1 Guest teaching 5.4 Guest disagreement 3.1 Harry pushing back 3.4
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 1:16:00 Sacca's scathing attack on Mark Zuckerberg
Sacca calls Facebook a cancer and describes directly confronting Zuckerberg to tell him 'the blood is on your hands' after the 2016 election.
Hardest push from Harry ▶ 52:01 Harry challenges Sacca's decision to take LP capitalHarry bluntly asks Sacca why he is taking external LP money when he is wealthy enough to self-fund all of Lowercarbon's investments.
Biggest teaching moment ▶ 59:45 Sacca lectures Harry on venture discipline and formulaSacca systematically outlines his four-step venture investment model and explicitly instructs Harry to adopt it for his own funds.
Harry holds his own ▶ 25:11 Harry attacks VC spinelessness in board meetingsHarry passionately hits back at the venture industry, accusing VCs of being too terrified of founder backlash to speak up in board meetings.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Chris Sacca’s Early Investing Career | 2 | 3 | 1 | 1 | Harry begins with a standard conversational prompt about Sacca's entry into investing. Sacca recounts early deals like Photobucket and Twitter in a warm, collaborative tone. | |
| Mindset Distortion and Public Market Failure | 4 | 5 | 3 | 3 | Harry cites Doug Leone to ask if early hits distorted Sacca's mindset. Sacca reframes the premise, explaining that losing millions day-trading student loans in 2000 humbled him long before venture capital. | |
| Maintaining Optimism and Redefining Wealth | 3 | 5 | 2 | 2 | Harry probes Sacca on maintaining optimism and managing wealth. Sacca educates Harry on probability math using Uber and Walmart crime statistics, and describes interviewing wealthy couples to avoid lifestyle pitfalls. | |
| Raising Balanced Kids and Combating Privilege | 2 | 6 | 3 | 2 | Harry asks broad questions about parenting, prompting Sacca to give an extended commentary against tech monoculture, youth over-specialization, and entitled kids. | |
| Radical Candor and Management Strategies | 5 | 6 | 3 | 5 | Harry offers strong pushback on VC cowardice in board meetings. Sacca re-educates him on tech power dynamics, noting employees hold more sway than VCs, and shares a toddler-inspired management model. | |
| The Obsessive Mindset and Stepping Back | 4 | 5 | 2 | 3 | Harry brings up Max Levchin's hiring philosophy and questions whether Sacca's self-assessment was wrong. Sacca elaborates on the obsessive mindset required for top-tier investing. | |
| The Formation of Lowercarbon Capital | 5 | 6 | 3 | 6 | Harry directly challenges Sacca on why he needs outside LP money given his vast wealth. Sacca explains the unit economics and massive capital requirements of climate scaling. | |
| Investment Discipline and Secret Sauce | 6 | 7 | 3 | 4 | Harry quotes Bill Gurley to question venture deployment discipline. Sacca provides a masterclass on deal selection, explicitly instructing Harry on how to de-risk investments. | |
| Are VCs Helpful and is Success Cyclical? | 6 | 5 | 4 | 6 | Harry aggressively criticizes current transactional VC trends like Tiger Global. Sacca pushes back on total cynicism, pointing out where founder selection and investor value-add still dominate. | |
| Diverse Managers and HBCU Initiatives | 4 | 6 | 2 | 2 | Harry asks about key lessons from 75 LP investments. Sacca breaks down the financial thesis behind funding underrepresented fund managers and his fee-free HBCU initiative. | |
| Quick Fire: Books, Partners, and Big Tech Criticisms | 4 | 5 | 8 | 3 | During quick fire, Sacca launches a fierce attack on Facebook, Mark Zuckerberg, and SoftBank, calling Facebook a cancer and detailing personal confrontations. |
Statements from this episode (34)
Sacca's first angel investment was Photobucket, which sold for $330 million
“The very first one I did on my own was a company called Photobucket, which we ultimately sold for three hundred thirty million dollars, which sounded like all the money in the world at the time.”
Chris Sacca funded his first $50,000 angel investment using credit cards
“But that check I wrote was literally a credit card check for me. I didn't have any cash on hand. I was at Google, and I was vesting, but I hadn't sold any stock yet, and so I literally I went into that one with 50,000 dollars of credit card checks.”
Chris Sacca's second angel investment was a $25,000 check into Twitter
“My second investment was Twitter, and that one was funny because Evan Williams was, I'd already been working with the company and helping him out, but Evan went and circled up investors for the round, and he's like, hey, I've got you down for 25 K, 25 K, good,…”
Chris Sacca day-traded student loans to $12M before losing it all
“So I very famously took my student loan checks for law school, told the school they hadn't shown up, cash them, and use them to day trade in the market. And so this is one of the reasons why I get so nervous about what I see in the Robin Hood phenomenon. You k…”
Chris Sacca: Attribute investment upside to luck and downturns to personal talent deficit
“When things are, without that kind of quote unquote training that came by way of tragedy, when things are going up, you tend to think it's correlated with your genius and talent. And when things are going down, you tend to think it's unlucky. And you learn ove…”
Chris Sacca passed on Airbnb fearing "blood on your hands" from crime
“It was a lack of optimism that cost me some money in the beginning when I met the Airbnb guys and I pulled them aside and was like, look, somebody's going to get raped or murdered and the blood is going to be on your hands.”
Sacca: We actively help elect progressive candidates who raise our taxes
“We're probably some of the most progressive people in technology, and certainly we help elect candidates who are going to raise our taxes.”
Chris Sacca: Computer science graduates are out of touch with reality
“What happens is we have this monoculture of these kids who, in computer science programs now, they've never had a job. Like, the toughest job they've ever had was being a teaching assistant for a class, and so they've never mowed lawns, waited tables, worked i…”
Lowercarbon Capital only hires people who have worked service or manual labor
“We in our organization will only hire people Who have had shitty jobs, who've had service jobs, who've worked extremely hard for some point in their life, and who appreciate that the worst day of being a VC doesn't begin to compare to the worst day of working …”
Travis Kalanick was ousted after 13 senior Uber managers demanded his exit
“In the end, what pushed Travis out was when his team held him accountable. It was when the, you know, his 13 senior managers all wrote a letter that said, dude, you've got to stay out of the company.”
Sacca: Bill Gurley directly confronts founders in board meetings to instil discipline
“I've watched Bill Gurley knuckle up in board meetings and call bullshit, because that's the place it needs to get done, and if you don't build that rigor and discipline early on, you're not setting yourself up to be a world-class company”
Lowercase Capital managed $6 billion in assets with only three employees
“At the height of lowercase, we were managing six billion dollars, and we were three people.”
Chris Sacca pays Lowercarbon employees six to ten times the industry standard
“So by the way, I mean, our comp plan probably runs six to 10 times what the industry standard is because I want everyone to materially, I want this to be a life-changing event.”
Sacca: Successful venture capitalists are obsessive, not balanced
“Look, the people who succeed in this business, and this is not an endorsement, this is an observation, are not normal. Like they don't have incredible balance. And so they may like make good time for family and good time for health and working out and may put …”
Sacca: Shark Tank is completely unscripted with zero advance info on pitches
“Shark Tank's real. Like, just so you know that none of that is scripted. It's the most authentic show on television. They don't tell us what to say or, and we invest our own money. We don't know anything about those companies before they walk in the door.”
Solugen reached a nine-figure run rate with 50% to 60% gross margins
“And so we see this happen with, like, a company, Solugen, who's making industrial chemicals using enzymes instead of petroleum. These guys, like, they're, yes, their first VAT cost a lot of money, but they now are, you know, I don't know if I'allowed to say, b…”
Chris Sacca predicts climate tech will make him richer than early web2
“Absolutely. I'll get way richer from this. I mean, we have, I have multiple companies in the portfolio right now that have the very like they have a trajectory to being multi-trillion dollar market cap.”
Chris Sacca: Commercial nuclear fusion is imminent, far under 30 years away
“You know, I deeply respect all the work you've done in the space, but you sound like someone who hasn't visited the lab in a while, because that's not where it is, and I can't preempt any announcements coming from any of our companies, but I can assure you it'…”
Sacca: Climate adoption requires superior products, not guilt and shame
“Guilt and shame aren't going to change behavior at scale. The only thing that's really going to get us there is offering people something that's better, cheaper, faster, cooler, sexier, easier to use, easier to maintain.”
Chris and Crystal Sacca are LPs in dozens of funds led by diverse GPs
“Crystal and I are LPs in dozens and dozens of funds, Because that was one of the ways we paid it forward, you know, and to help kind of promote diversity in the industry, we backed literally dozens of first-time general partners who are women, people of color,…”
Sacca: Every VC deal must offer single-handed life-changing financial potential
“I say in every deal, we have to give ourselves a chance in that one deal to get rich. And this is because I've done, I did YC deals back in the day where I'd put 25 grand in and I'd sell the company for, you know, fifteen million dollars. My 25 grand became 75…”
Lowercarbon Capital requires every investment to have gigaton carbon removal potential
“We in climate, we specifically make sure every deal has more than a gigaton carbon removal potential.”
Sacca: True VC discipline is picking deals you can personally de-risk
“The discipline is around not just doing every deal that comes your way, but then doing the deals where you personally can de-risk something. Maybe it's moving it from 49 to 51% likelihood, but, you know, maybe you can't add 20% likelihood to the success, but i…”
Bill Gurley presented six vetted public CFO candidates at an Uber meeting
“We were in an early Uber board meeting once, and we needed a CFO. And I kind of, I, They said, okay, we need a CFO. And I stopped and I think, okay, like who could be a CFO? And I'm thinking of like old Google people who were like director of finance and maybe…”
Kevin Systrom specifically targeted Sacca, D'Angelo, and Dorsey for Instagram's angel round
“Instagram came to me, but like Kevin Systrom literally said, I want three angels, you, Adam D'Angelo and Jack Dorsey. And so he pitched me. I literally was not seeking photos. I, it sounds fucking hilarious, but I thought it was spent. I thought it was done. A…”
Sacca: VCs must self-promote to maintain collaborative deal flow
“To investors who are up and coming, I think you need to consistently remind other investors of how you're helpful. So, you know, people are like, you know, Saka, you're self-promotional. I'm like, fuck yeah, I am. Like, that's part of the job is I have to cont…”
Chris Sacca's LP portfolio of diverse venture managers is running at 2.5x
“It turns out right now that our LP portfolio of diverse managers is running about a two and a half X.”
Lowercarbon Capital charges zero fees and zero carry to HBCU investors
“For HBCUs, we would do no fee, no carry.”
Sacca: Four venture firms joining Lowercarbon's HBCU access initiative
“So far, we have four other firms who are going to follow us along and start giving more access, whether it's donated interests or it's or no fee, no carry.”
Chris Sacca calls Facebook a "cancer" and claims its leadership knows it
“Yeah, I think Facebook is a cancer, and they know it.”
Chris Sacca claims he watched Mark Zuckerberg lie to the U.S. President
“And I've been in the room with Zuckerberg. I've watched him fucking lie to the president of the United States about what they know internally versus, like, the claims he spouts out loud.”
Chris Sacca calls SoftBank "value destructive" in the venture capital industry
“But I think SoftBank is just value destructive, and it drives me fucking crazy.”
Chris Sacca claims Lowercarbon Capital's current internal rate of return is 95%
“The multiples are already there. I think IRR is 95% right now, and so so we're already getting fucking rich doing it”
Chris Sacca: Rogue states will unilaterally deploy geoengineering if democracies do not
“And if we don't do it, You know, North Korea is going to do it on their own. Like, some rogue state is going to launch a projectile that explodes a bunch of dust in the atmosphere, and we won't know which dust, which altitude, and the best ways to do it, and w…”
Shorts cut from this episode
▶ Crazy $14M Student Loan Profits 🤑 to Total Bomb 📉 🤯 · 20V (@4:18)
▶ Chris Sacca: How I knew Sundar Pichai would become CEO of Go (@43:12)
▶ You won't believe what this Swedish guy invented 😲 · 20VC w (@48:38)
▶ Billionaire to fix climate change with capitalism · 20VC wit (@55:16)
▶ You won't believe what this Swedish guy invented ✈️ 🇸🇪 #s (@48:38)
▶ Two EPIC Wedding Vows 💍 #shorts · 20VC with Harry Stebbings (@1:14:00)
▶ How long until we achieve Nuclear Fusion ⚛️ #shorts · 20VC w (@54:20)
▶ Convincing Goldman Sachs to invest in Climate Change 🤑 #sho (@1:20:02)
▶ How to fix Climate Change with Capitalism 🌎 #shorts · 20VC (@55:16)
▶ This billionaire wants to fix climate change ♻️ #shorts · 20 (@48:01)
▶ Chris Sacca: I always knew Sundar Pichai would become Google (@43:12)