Oct 11, 2021 · 1h 16m · 20vc
20VC: Chris Sacca on Coming Out of Retirement To Unf**k The Planet with Lowercarbon, How Chris Evaluates His Relationship To Money Today, Why We Have Bred a Generation of Ass**** Kids, Do VCs Provide Any Real Value and The True Unfiltered Opinion on Faceb
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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 episode of 20VC, host Harry Stebbings interviews venture capitalist Chris Sacca about his legendary career, lessons from catastrophic financial loss, grounded parenting amidst wealth, and his return to active investing to back high-margin climate technology startups through Lowercarbon Capital.
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 15.2% of the talking time here. How this is scored →
Harry as informed peer 4.5 Guest teaching 6.2 Guest disagreement 3.1 Harry pushing back 2.2
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 1:06:04 Sacca's blistering critique of Facebook and Zuckerberg
Sacca pulls no punches, describing Facebook as a cancer and sharing direct confrontations where he accused Zuckerberg of lying and causing harm.
Hardest push from Harry ▶ 48:00 Harry asks why Sacca raised outside capital when already wealthyHarry pushes directly on Sacca's motivations by asking bluntly why he would take outside LP money when he has ample personal wealth.
Biggest teaching moment ▶ 52:00 Sacca dismisses conventional LP fund discipline dogmasSacca dismantles conventional venture wisdom around target ownership slides and pacing, teaching Harry his personal four-part formula for deal conviction.
Harry holds his own ▶ 26:16 Harry pushes back on passive VCs losing their voiceHarry strongly articulates his frustration with cowardly venture capitalists refusing to speak up or challenge founders during 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 |
|---|---|---|---|---|---|---|
| Early Days of Investing from Photobucket to Twitter | 4 | 4 | 1 | 1 | Harry sets up the opening by asking about Chris Sacca's earliest investments. Sacca recounts financing Photobucket on credit card checks and entering Twitter early through Evan Williams. | |
| Public Market Crashes, Ego Management, and Maintaining Optimism | 5 | 6 | 2 | 2 | Harry references an interview with Doug Leone about how early hits distort mindset. Sacca shares his experience of losing four million dollars day trading in 2000, which taught him to attribute upside to luck and downside to lack of hustle. | |
| Evolving Relationship to Money, Lifestyle, and Removing Anxiety | 4 | 6 | 1 | 1 | Harry asks about Sacca's changing relationship with wealth. Sacca explains interviewing people whose lives and families were ruined by money to actively avoid those pitfalls. | |
| Parenthood, Fighting Childhood Entitlement, and Modern Culture | 4 | 7 | 4 | 1 | Sacca delivers an extended critique of modern hyper-specialized parenting, childhood entitlement, and the tech monoculture. Harry chimes in to validate Sacca's observations about losing humanity. | |
| Radical Candor, Founder Accountability, and Management Coaching | 5 | 6 | 3 | 4 | Harry challenges the industry standard of VCs staying silent and terrified of founder conflict. Sacca agrees VCs are often timid managers but clarifies that internal employee pressure is the true accountability mechanism in tech. | |
| Building High-Performing Teams, Radical Transparency, and Knowing When to Retire | 4 | 6 | 3 | 2 | Harry asks about hiring thresholds and whether doubt equals a definitive no. Sacca explains his intolerance for 'B-teamers' and details why Lowercase maintained extreme compensation and radical transparency. | |
| Venture Obsession, Limits of Personal Scope, and Shark Tank | 4 | 6 | 2 | 1 | Harry asks Sacca to reflect on his temporary retirement from venture capital. Sacca candidly assesses his inability to stay obsessive about consumer apps or manage large corporate structures like Sundar Pichai. | |
| Lowercarbon Capital, Climate Tech Economics, and Scalable Impact | 5 | 6 | 3 | 4 | Harry directly challenges Sacca on why he raised external capital for Lowercarbon Capital when he already has personal wealth. Sacca explains that catalytic climate tech requires massive scale and changed unit economics. | |
| Market Dynamics, Exponential Returns, and Pragmatic Climate Solutions | 4 | 7 | 4 | 2 | Harry asks if climate investing will yield more returns than classic tech. Sacca asserts that market forces and exponential technological curves, not moral guilt, will transform global procurement. | |
| Venture Capital Discipline and the Four-Part Value-Add Formula | 6 | 7 | 4 | 5 | Harry questions venture deployment velocity and whether true value-add exists. Sacca rejects conventional LP slide constraints, laying out his 4-part formula and citing Bill Gurley's operational value-add. | |
| Backing Diverse Managers and Institutional Access for HBCUs | 4 | 6 | 2 | 1 | Harry asks about insights from writing 75 LP checks into diverse managers. Sacca emphasizes that backing underrepresented GPs delivers superior economic returns rather than charitable outcomes. | |
| Quickfire Round, Corporate Critiques, and the Path Ahead | 5 | 7 | 8 | 2 | In the quickfire round, Harry asks about Sacca's public critiques of Facebook and SoftBank. Sacca launches a fierce condemnation of Mark Zuckerberg and SoftBank's predatory investing practices. |
Statements from this episode (33)
Sacca's first angel check 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. You know, Flickr had sold for like 25 to thirty five million doll…”
Sacca funded his first $50,000 angel check with credit card debt
“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. I went into that one with 50,000 dollars of credit card checks.”
Sacca: Treat market success as luck and failure as a personal flaw
“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. You learn over time to invert that curve. When things are going up, it's lucky, and when things are going d…”
Sacca backed Triller and DubSmash before TikTok took over
“We had two other investments, Triller and DubSmash, that were kind of the same thing, right? And there's no real reason that they didn't succeed. They just didn't.”
Sacca passed on Airbnb in 2008 fearing 'blood on your hands'
“It was a lack of optimism that cost me some money in the beginning when I met the Airbnb guys in 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.”
Evan Williams interviewed wealthy people for tips before earning his fortune
“When Evan Williams saw that he was going to make some money, he went out and started interviewing rich people and asking them for tips.”
Sacca actively supports political candidates who will raise his 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.”
Sacca: Lowercarbon will only hire candidates with service or manual labor experience
“And 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 in…”
Travis Kalanick was ousted by a letter from 13 senior Uber managers
“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 and said, dude, you gotta stay out of the company.”
Lowercase Capital managed $6 billion with just three employees
“I think we're six people now managing, you know, between the outside money and inside money over a billion dollars. At the height of lowercase, we were managing six billion dollars and we were three people.”
Lowercarbon's compensation plan is six to ten times VC industry standards
“Our comp plan probably runs six to 10 times what the industry standard is”
Early Google shared board decks company-wide with zero leaks for four years
“Google taught me that when they would share confidential information, they would share the board deck with the entire company on Fridays. Literally, they'd gather the entire company and show them the same slides they had shown the board on Wednesday. And that …”
Sacca stepped away from VC because he feared becoming a 'B-teamer'
“That's one of the reasons I quit for a while. Was I worried that, you know, the stage of life I was in, I wasn't going to be able to fucking bring it. I wasn't going to be able to as obsessive as you need to be to succeed in this business and this industry and…”
Successful venture capitalists are obsessives lacking intellectual balance
“The people who succeed in this business, and this is not an endorsement, this is an observation, are not normal. 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 vacations o…”
Sacca: Shark Tank is completely unscripted and investors use personal capital
“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.”
Heart Aerospace secured billions in airline orders on single-digit millions spent
“Fast forward a couple years, and not on the billions of dollars of investment it normally takes to develop an aircraft, but on the single digit millions of dollars in this case, and I think we just did a round in the tens of millions, and up until that round, …”
Solugen reached a nine-figure run rate with 50% to 60% margins
“A company, Solugen, industrial chemicals using enzymes instead of petroleum. Yes, their first VAT cost a lot of money, but they now are, you know, I don't know if I'allowed to say, but their run rate is ridiculous. Like, I'll fucking say it, like, nine-figure …”
Sacca: Climate technology is the largest addressable market in human history
“These are the biggest total addressable markets in the history of the fucking world, because it turns out, like, the total addressable market is everyone who eats, and everyone who wants to move their bodies somewhere around the planet, and everyone who wants …”
Lowercarbon Capital has $1 billion invested in climate tech
“We've got basically a billion dollars at work In the field right now”
Sacca predicts Lowercarbon will outperform his legacy software venture investments
“Absolutely. I'll get way richer from this. I have multiple companies in the portfolio right now that have, like, they have a trajectory to being multi-trillion dollar market cap”
Sacca: Commercial nuclear fusion is far closer than 30 years away
“I can assure you it is much, much more near term than 30 years imminent, maybe now, who knows, but it's been fucking fascinating to see these accelerating curves”
Sacca: Climate technology must win on economics and product quality, not guilt
“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 backed dozens of underrepresented first-time 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,…”
Lowercarbon Capital requires every deal to have gigaton-scale carbon removal potential
“In climate, we specifically make sure every deal has more than a gigaton carbon removal potential.”
Kevin Systrom sought only Sacca, Adam D'Angelo, and Jack Dorsey for Instagram
“Instagram came to me. Kevin Systrom literally said, I want three angels, you, Adam D'Angelo, and Jack Dorsey.”
Lowercarbon's LP investments in diverse fund managers are returning 2.5x
“And so it turns out right now, our LP portfolio of diverse managers is running about a two and a half X.”
Sacca: Four VC firms committed to joining Lowercarbon's HBCU access initiative
“And 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 exposure to HBCUs to start participating in this ecosystem more meaningfully.”
Sacca says he watched Mark Zuckerberg lie to the U.S. President
“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.”
Sacca: Uber's IPO would have gone differently without SoftBank's DoorDash funding
“Uber's IPO would have gone very differently if they hadn't funded DoorDash.”
Sacca calls SoftBank value destructive
“I think SoftBank is just value destructive, and it drives me fucking crazy.”