May 18, 2026 · 1h 35m · news
Turning Peter Thiel's $100K into $10M Angel Portfolio & Why VCs Can Be Sharks | Josh Browder · 20VC with Harry Stebbings
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In this episode of 20VC, host Harry Stebbings interviews tech entrepreneur and investor Josh Browder on how he turned a $100,000 Thiel Fellowship grant into a $10 million portfolio, his unique 'Hotel California' founder incubation model, and his profitable, capital-efficient philosophy behind DoNotPay.
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 25.8% of the talking time here. How this is scored →
Harry as informed peer 4.3 Guest teaching 3.1 Guest disagreement 1.9 Harry pushing back 2.4
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 20:20 Josh rejects host's safety net premise
Josh explicitly shuts down Harry's suggestion that family wealth gave him a safety net to drop out, explaining that his father's arrest by Russian operatives created severe paranoia rather than security.
Hardest push from Harry ▶ 1:27:23 Harry challenges San Francisco's startup dominanceHarry directly refuses the consensus framing that San Francisco is ideal, arguing talent cost and poor retention make it the worst place to start a company today.
Biggest teaching moment ▶ 20:20 Reframing safety net as mafia-induced paranoiaJosh corrects Harry's assumption that he had a cozy safety net by revealing his father was targeted by Russian authorities, totally reframing his psychological motivation.
Harry holds his own ▶ 1:16:54 Harry outlines the macro exit bottleneckHarry demonstrates deep venture expertise by detailing the $500M revenue requirement for tech IPOs and pointing to private equity stress like Thoma Bravo and Medallia.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| What Motivates Founders: The Delusional Fear of Losing | 2 | 1 | 1 | 1 | Harry opens by asking whether fear of losing or joy of winning drives founders. Josh explains the fear of losing, and Harry relates by sharing his own early fear of fading away like Macaulay Culkin. | |
| The Reality of Backing Extremely Young Founders | 3 | 3 | 1 | 2 | Harry inquires why Josh aggressively backs very young founders and how he identifies non-obvious founder traits. Josh shares detailed interview tactics and red flags like checking Stripe apps live. | |
| The 'Hotel California' One-Man Accelerator and Why Startups Fail | 3 | 3 | 1 | 2 | Josh describes his spare-room incubator approach, calling it 'Hotel California' where pre-seed founders stay until institutional funding. Harry asks about the top mistakes made during this incubation. | |
| Co-Founder Dynamics and the Rise of Ideological Fraud | 4 | 3 | 2 | 2 | Harry brings up founder pattern-matching indicators like family trauma or early gaming. Josh agrees and describes how pitch-coached founders engage in 'ideological fraud'. | |
| Breakfast with Marc Andreessen: For-Profit Impact and 'Breakfast Clothes' | 3 | 2 | 2 | 2 | Josh recalls meeting Marc Andreessen in Atherton while wearing 'breakfast clothes', where Marc convinced him to build DoNotPay for-profit to scale impact. Harry guides the conversation smoothly. | |
| The Stanford Poker Game and My Father's Arrest by Russians | 3 | 4 | 4 | 2 | Harry suggests Josh's safety net eased his Stanford dropout decision. Josh directly rejects the premise, sharing how receiving a news alert about his father's arrest by Russian operatives during a poker game induced intense paranoia. | |
| Rejection on Sand Hill Road: Three Pitch Changes That Saved Do Not Pay | 3 | 4 | 1 | 1 | Josh recounts his hardest day after endless Sand Hill Road rejections, and how advice from lawyer Damien Weiss to add a demo, big company logos, and a subscription model turned rejections into instant checks. | |
| The Art of Pitching VCs: Poker Rules, Demos, and In-Person Connection | 4 | 3 | 2 | 2 | Harry and Josh discuss VC pitch tactics, with Harry highlighting multi-founder Zoom pitch mistakes and Josh emphasizing in-person meetings and non-disclosure of target prices. | |
| Dropping Out of Stanford and turning $100K into a $10M Portfolio | 3 | 4 | 1 | 2 | Josh recounts dropping out after failing a required social dance class, and turning his $100K Thiel Fellowship grant into an eight-figure angel portfolio by investing in peers like Adam Guild. | |
| The Evolution of Thiel Fellowship Vetting and Why Limitations Reveal Style | 4 | 3 | 2 | 2 | Harry compares the Thiel Fellowship to Y Combinator. Josh contrasts large accelerator dilution with his single-room high-focus approach, while Harry introduces Matthew McConaughey's quote on limitations revealing style. | |
| Scaling the 'Hotel California' Model and the Stanford Facebook House | 3 | 3 | 2 | 3 | Harry humorously pitches a joint media-incubator house, but Josh defends keeping the artificial constraint of a single spare bedroom to maintain intense focus on each startup. | |
| Resilience over Credentials: Why 'Never Give Up' Beats spelling Bees | 6 | 3 | 2 | 3 | Harry presses on why Josh backed Micro 1 when staffing appeared uninteresting. Josh argues grit beats credentials, while Harry cites impressive revenue scaling figures from current AI startups like Lagora and Lovable. | |
| The Kingmaker Effect: Valuation vs. Brand in Venture Capital | 7 | 3 | 2 | 3 | Harry demonstrates strong venture knowledge regarding dilution and fund management, noting he caps single-check allocation at 7% whereas Josh put 15% of fund three into Owner.com. | |
| The Risks of Selling Secondaries Early | 7 | 3 | 2 | 4 | Harry questions whether SAFE stack conversions hurt founders later, citing detailed fund dynamics. Josh warns founders about secondary buyers acting as sharks. | |
| Protecting Founders from VC Shark Tactics | 5 | 3 | 3 | 4 | Harry pushes back on founders collecting term sheets on strict timelines, stating he hates that process. Josh advises founders to give VCs overnight deadlines to force decisiveness. | |
| DoNotPay's Profitability, Lean Team, and Organic Model | 7 | 3 | 2 | 3 | Harry highlights SEO vulnerability by citing Monday.com CEO's 15% SEO traffic drop. Josh explains DoNotPay's organic customer acquisition model, lean 11-person team, and dividend payouts. | |
| How to Hire the Best First 10 Startup Employees | 4 | 3 | 1 | 2 | Harry asks about early team hiring strategy and wealth disparity in San Francisco. Josh critiques strategy hires and outlines how AI wealth concentrates in positional assets. | |
| Why Josh Diversifies His Personal Wealth with Nevada Land | 4 | 4 | 2 | 2 | Josh explains why he invests personal capital into Nevada land to hedge against AI outcomes. He criticizes FTC regulatory overreach, citing blocked biotech acquisitions. | |
| Are Tech Layoffs Driven by AI Efficiency or COVID Overhiring? | 6 | 3 | 2 | 3 | Harry cites market data on Sierra raising at $15.9B to ask about hyper-competitive markets. Josh defends competitive sectors, noting that huge market sizes justify the crowd. | |
| The Constrained Exit Landscape and the Rise of Secondaries | 8 | 3 | 2 | 3 | Harry displays top-tier market expertise by outlining Series A multiple traps, the $500M ARR IPO requirement, and PE buyout challenges like Thoma Bravo and Medallia. | |
| Unsolved Consumer Rip-Offs and DoNotPay's Core Mission | 4 | 4 | 1 | 2 | Josh discusses unresolved consumer pain points like bill negotiation and in-flight Wi-Fi refunds, and recalls making an unofficial Pret A Manger app at age 14. | |
| UK's 'Finetopia' and the US Scale of Ambition | 3 | 3 | 2 | 2 | Josh calls the UK 'finetopia' due to excessive speed cameras and fines, while comparing UK vs US founder ambition scales. | |
| The Serendipity and Social Stratification of San Francisco | 6 | 4 | 4 | 5 | Harry directly challenges San Francisco's dominance, arguing it is the worst place to start a business due to high talent costs and low retention. Josh counters by emphasizing SF's unique serendipity and flat social hierarchy. | |
| Quick Fire: The Kindest Act of Founder Integrity | 2 | 2 | 1 | 1 | In the quick-fire segment, Josh discusses the reality of the AI shift, names Ali Ansari as underrated, and shares a story of founder integrity where lost funds were gifted back as equity. |
Statements from this episode (98)
Browder: Founders not motivated by fear of losing are asleep
“If you're not motivated by the fear of losing, I think you're asleep at the wheel.”
Browder: Tech wealth gap between AI and laid-off workers is unsustainable
“For every anthropic employee who's making 20 to a hundred million, there's 7000 block employees being laid off. It's not sustainable. You can't have 50,000 people with all the money.”
Browder: Growing tech wealth disparity could trigger a revolution in our lifetime
“I think, actually, there could be a revolution in our lifetime.”
Browder reduces summer investing to avoid fake student dropouts
“I'm actually, it's scaled back a bit during the summer, not because I'm in Capri like all the other VCs, but because you have to worry about these fake founders.”
Browder: Proposing late-night meetings filters top founders from mediocre ones
“So a small signal would be let's meet at 11 p.m., and the best founders would say, sure. The mediocre ones would say, oh, no can we meet Tuesday week?”
Browder: Great founders focus on tactical customer sales over vague partnerships
“A D minus answer would be some vague nonsense, like I want to get a partnership with Anthropic. An A plus answer would be I'm going to like fly to Milwaukee to meet with a dentist to get them to sign my 500 dollar a month SaaS plan.”
Browder: Top entrepreneurs demonstrate elite skill in childhood side projects
“Then I look for do they have a top one percent skill in something to achieve their business goals? And you see the best entrepreneurs, they've proved something in their childhood Maybe they were selling Minecraft servers like Adam Guild or John Andrew, the fou…”
Josh Browder: Browder Capital targets sub-$5M valuations for initial checks
“I try and get in sub five million valuation.”
Browder requires pre-seed founders to live with him until raising seed
“It's in California, so it's like Hotel California, where you can't check out until you've raised your institutional seed, and then I, the company is off life support, and I can, like, relax a bit.”
Josh Browder: Pre-seed startups fail due to money, hope, or co-founders
“At the very beginning, there's three reasons why pre-seed companies fail. They run out of money, they run out of hope, and co-founder disputes.”
Browder: High school friendships yield the best young co-founder dynamics
“The best co-founder dynamic that I've seen among young founders is friends from high school.”
Browder: Founders reverse engineer podcast commentary to fake investor alignment
“I've noticed a really worrying trend of people reverse engineering what I say on podcasts and in articles to pitch me exactly what I'm looking for.”
Stebbings: 90% of young founders pitch traits he publicly values
“I would say nine out of 10 young founders that we meet pitch those three exactly, and you're like, wow, this is very aligned.”
Browder: Latest fund median startup valuation cap is $5M across 33 deals
“For my latest fund it's, I've done 33 deals so far. The median across the entire fund is five. The minimum is 1.5. Maximum is 21.”
Browder: Illegal startup fraud is getting harder due to online transparency
“I actually think it's becoming easier and easier. The world is becoming much more transparent. You have Twitter sleuths who Will detect anything as like several companies recently have been taken down because of like someone published an article about SOC two …”
Browder: For-profit companies achieve 10x the impact of non-profits
“And Mark convinced me that the biggest organizations are for-profit entities, and you can have 10 times the impact of a for-profit company because the incentives are aligned.”
Browder: Venture investors at best watch things happen, at worst wonder what happened
“There are three types of people, those who make it happen, those who watch it happen, and those who wonder what happened. And I think at best venture investors are in the second one. Sometimes unfortunately they can be in the third.”
Browder: Conventional 'paint-by-numbers' career paths before founding no longer work
“The problem is the world changes so quickly that the paint by numbers approach doesn't work anymore. And so I would say to any founder who has an idea of what they want to do, they should just go for it, and the world won't wait for them.”
Browder: Dropping out of college just for the sake of it is wrong
“Now dropping out is almost the establishment. So you see people drop out just for the sake of it. And I think that's definitely wrong because there are huge advantages to being in college.”
Browder: Turning to legal counsel for business advice signals extreme trouble
“If you're turning to outside counsel for, like, business advice, then you know things are really bad.”
Browder: Silicon Valley VCs exhibit herd mentality by rescinding rejections
“Silicon Valley is such a kind of herd mentality place. Even the people that previously rejected me, once they found out that this firm wants to invest, everyone starts to, like, rescinding their rejections.”
Browder: Founders should never reveal target valuation when pitching VCs
“Pitching VCs is like a game of poker. You should never reveal too much information about what you're seeking. So every founder I invest in, I say, don't reveal the price that you want. The price is a function of how hot the deal is, which ironically is less ho…”
Browder: Startup pitches should be conducted by the CEO alone
“Also, I think the, I mean, there's a million things, like the CEO should be doing it, not like five founders speaking over each other.”
Browder: Pitching VCs on Zoom is a mistake; founders should meet in person
“Yeah, well, Zoom is the first mistake. They should fly to London. In person, I say you should reject Zoom and always do in person where impossible, where possible.”
Browder: Founders must balance boundless future vision with factual current state accuracy
“It's okay to Be as hyped as possible with your vision and ambition. You should have boundless ambition, but with how you're describing the current state, it should be very accurate.”
Browder: Delusional levels of founder ambition correlate with startup success
“All of the best farmers I've invested in, they, they've had delusional levels of ambition. The more delusional, the better. And unfortunately, it is a sign of success to be delusional.”
Browder: Failing Stanford dance class precipitated dropout, not Thiel Fellowship
“I didn't go to the dance class. I kept Do Not Pay running and failed at the dance class, and that was my precip, kind of precipitated my dropping out, not the Teal Fellowship.”
Browder invested his entire Thiel Fellowship grant in fellow founders
“Yeah, I put all my Teal Fellowship money and I invested it in Adam Guild and other amazing entrepreneurs.”
Browder expects $100K Thiel Fellowship investments to reach eight figures
“I think when it's all said and done, it will be an eight, eight figures.”
Browder: Middling startups are disadvantaged inside startup accelerators
“The problem with any accelerator, not speaking specifically about YC, is you're competing for attention with all the other companies in the accelerator. If you're the top of the accelerator, Then that's incredible. You're the king made or queen made company. B…”
Browder: Browder Capital will limit founder incubation to one company
“In fact, one of my LPs asked me, why don't you start buying a hotel or rent out a hotel and just do 10 at a time? And I said, well, that's, that removes the artificial constraint of one.”
Browder: Venture capital turns into a stampede after top-three firm invests
“Once they get the top three firm, it's like a stampede. It's like Safari stampede. Everyone is trying to invest, and I was thinking, where were all these people just three weeks ago?”
Browder: Micro1 is his best-performing investment at over 1,000x return
“Ali Ansari is a micro one, is objectively my best performing investment in terms of multiple. The founders get upset when I reveal exact valuation numbers, but let's say over a thousand X, well over a thousand X and based on the kind of the scale of the busine…”
Browder: VCs err by scouting high school math Olympiads over grit
“And I think this is actually a mistake a lot of VCs are making. They are focusing too much on, on these credentials. So there's a race right now to back the math Olympiads. VCs are like going to spelling bees and math competitions in high school.”
Browder: Browder Capital avoids investing in crypto, consumer hardware, and biotech
“There's a few things that I'll never touch. I'll never touch crypto. I'm not getting into whether I believe in crypto or not. I think it has huge use cases, but I think it's best left to the crypto funds. Consumer hardware is tough because of various, various …”
Browder: AI infrastructure pitches like agent observability are jargon-filled BS
“Everyone is pitching this AI infrastructure nonsense. Like we're building agent observability, like the jargon levels. I'm British. I think that's all BS. Like they just add on the jargon.”
Browder: Valid startup business models must pass the pub test
“If you can't explain the business to someone at the pub in the UK, like, if you go to a pub and say I'm building observability for AI agents, they'll laugh at you. Like, but if you say I'm building, like, software to automate health insurance claims, that make…”
Browder: Accept Sequoia or Founders Fund Over Double Valuation Term Sheets
“There's like the kingmaker firms that you should accept at any price. One example would be Founders Fund or Sequoia or people like that. And so if you get an offer from them at X and the offer from someone else is at two X, you should take their offer because …”
Browder: Market Noise Causes People to Outsource Judgment to Top VC Brands
“We live in such a noisy world that people outsource their judgment to established brands.”
Browder Capital's fourth fund will allocate zero capital to follow-on reserves
“I decided for my fourth fund, no reserves, just everything up front, Browder Hotel, let's go.”
Browder: Buyers of early startup secondaries are predatory sharks
“I think that the people buying these secondaries are sharks.”
Browder: DoNotPay avoided secondary sales by distributing dividends
“We haven't really had to because of dividends.”
Browder: Long-term seed investors should prefer SAFEs over priced rounds
“So as a pre-seed and seed investor the kind of B minus VC investors will want to get that next round on a priced basis to get that gap markup. But if you actually care about the economics and making money in the long term, you want the next round on a safe bec…”
Browder: VCs' pressure to raise next funds directly hurts founders
“So I think this raising the next fund nonsense really does impact decision making and actually directly hurts founders with some of these things.”
Browder: Predatory VCs act like sharks by demanding 15% seed option pools
“Well, the VCs always win. If they do a price round, some of them are sharks. They say we want a 15% option pool at the seed.”
Browder: VCs make fake customer promises to trick founders into signing SAFEs
“The VCs will say anything to get you to sign right there and then. Anything. They'll say, I, they, so they'll reverse engineer what the founder is looking for and say, oh, I'm friends. I'm buddies with that guy. I know someone at that company with golf buddies…”
Browder: Browder Capital requires overnight consideration and forbids signing on the spot
“And going back to my offers, I don't make them sign on the spot. It's just too much, especially for these young founders. I say, you have the night to think about it. I think decisiveness is a key quality. So I do want to know by the next morning, if not, it's…”
Browder: Browder Capital passes on founders running multi-day term sheet processes
“I say it's probably not a fit, especially given my investing model. I want to, so many ways to win. I'm sure that they might win or not, but that's not a fit for me. I say, good luck.”
Browder: Takes 5% to 7% startup equity and saves founders more over time
“I typically take five to seven percent and I will, I say to them, and I really think this is proven true, I will save them that over the life of the company.”
Browder: DoNotPay acquires over 90% of customers organically
“We get 90% plus of our customers organically through SEO, earned media, like viral stories and referrals.”
Browder: DoNotPay serves hundreds of thousands of customers with 11 people
“We have hundreds of thousands of customers, and it's only a team of 11 people, and it's automated, fully automated, so it's, like, very efficient.”
Browder: DoNotPay competitor spent $300 to acquire $150 customers in 2021
“We had a competitor in the 20, 21 peak. They were spending like 300 dollars to acquire a customer worth 150 dollars and they actually managed to sell at the peak of the market.”
Josh Browder: Founders who run out of cash should manage burn better
“I think this is controversial. I think founders who burn all the money, I think that's not cool. I think it's kind of lame because why did they run out of money? Why didn't they just cut the bun? And obviously some founders fail because of some like black swan…”
Browder: DoNotPay holds more cash than total venture funding raised
“So we have more money than we've raised”
Browder: DoNotPay plans to issue quarterly investor dividends
“We're actually doing another dividend next month, so it's like quarterly. Yeah, we're planning on doing it now quarterly.”
Browder: DoNotPay could have raised $100M during 2021 market peak
“We never, we didn't raise a hundred million. We could have at the peak of twenty-twenty-one.”
Browder: DoNotPay plans to roll up consumer products this year
“I think that we, Are gonna take some big swings this year. We are looking to kind of roll up some different consumer things within Do Not Pay”
Browder: Business school credentials are a counter-signal for startup hires
“I think business score is actually a counter signal.”
Browder: Early-stage startups should stay away from strategy hires
“Stay away from the strategy hires. Strategy is a meaningless hire because what does that even mean? Everything is strategic.”
Browder: Custom AI evaluation specialists will become commonplace within five years
“Custom evals is like evals. So everyone is very excited about foundation models, like called code and all of this stuff. But I think the future of AI will actually be organization specific, specifically around the data that do not pay has where we're doing eva…”
Browder: Niche software companies will thrive while traditional large tech struggles
“I think there'll be a rise of medium sized businesses, like almost do not pays that fill the niche and then these massive companies, but the middle where there's just like a large company, I think they have to be very worried.”
Browder: Prices for positional luxury goods will go off the charts
“And I think that the price of that will stay the same, but then there's like positional goods. There's only like eight seats in Delta first class. There's only eight houses where they want to buy it, like, On the best road in San Francisco, and the positional …”
Browder invests all personal earnings into land instead of stocks or cash
“In terms of like my diversification retirement I take all the money I make and I buy land. I don't put it in the stock market. I don't buy, I don't keep it in cash because I think that the dollar is, it doesn't have a good future. I don't buy bonds or anything…”
Josh Browder: Nevada is unique in US for zero income tax, low property tax, and growth
“There's only three things are true in Nevada. There's no state income tax. There's very low property tax and it has a rising population. And that is not true, in my opinion, anywhere else in the US. So if you compare it to Florida, for example, there is no sta…”
Browder: Trump administration is objectively better for tech ecosystem
“I think that whether you agree or disagree with what's going on right now it's objective that for tech the current administration is a lot better.”
Browder: FTC blocked acquisitions of several portfolio companies
“Several companies I invested in had the acquisitions blocked by the kind of Lena Kahn style approach.”
Browder: Real assets are the only way to stay ahead in an AI economy
“The only way to stay ahead in this AI world is, is to have real assets.”
Browder: Nevada land investments generate 10% to 20% safe IRR
“It's only, like, 10 to 20% but it's very safe.”
Browder: Meta's layoffs are driven by AI-powered engineer productivity
“With Meta, I think it's AI driven. There, it's clear that they're spending so much money on their data centers, and AI has made their engineering more productive. They need fewer engineers.”
Browder: Block's layoffs are due to COVID overhiring, not AI
“But maybe with a company like Block maybe it's controversial, but I think it's more about the COVID overhiring.”
Browder: Companies in the future will be dramatically smaller
“Absolutely. I think that It's objective.”
Browder: DoNotPay's 10 support contractors are becoming redundant via AI
“You don't need, I mean, even with do not pay customer support we're seeing optimizations. Previously, you had to hire, like, three people to do the job of one person. Now, now so we do have, like, 10 extra, like, contractors for customer support. We found that…”
Browder says all his best investments were in competitive markets
“All of my best investments have actually been in very competitive markets.”
Browder: AI labs award data labeling startups up to $1B contracts
“It's not unusual for large labs to throw these companies a hundred million, even close to a billion dollar contracts, and so I think there's a reason everyone is excited about it.”
Stebbings: Series A is the worst stage in venture capital
“I think Series A is the worst place to be in the market. Little PMS, like one to three million of revenue. But the price is 200 X ARR.”
Browder: Late-stage billion-dollar investments can be better than Series A
“Sometimes the best place to be could actually be investing a billion or things like that. Where it's de-risked. You can model the cash flows.”
Stebbings: Startups cannot IPO today with under $500M revenue
“If you look at IPOs today, you can't IPO with less than five hundred million in revenue.”
Browder Capital is actively selling secondary positions in portfolio companies
“We're doing some now, actually.”
Browder: Large VCs selling secondary shares creates fatal signaling risk
“If Menlo Ventures sell secondary in a company, the company is dead because the signaling risk is, is huge or any firm.”
Browder: Selling small secondary stakes carries minimal signaling risk
“No, I think it depends if it's like a small part of one stake. And the good thing is these things can be sizable and you only sell a small portion, then there's not much signaling risk in that. Additionally, it sometimes helps the founders. Oftentimes they're …”
Josh Browder expects to make more money from investing than DoNotPay
“I think unfortunately I'll make more money from the investing.”
Browder: Startup founders hate working with professional money managers
“Founders love to work with other founders. They hate professional money managers.”
Browder: DoNotPay achieves a 100% success rate on in-flight Wi-Fi refunds
“We have a hundred percent success rate with in-flight Wi-Fi refunds because it never works. I guess, so I guess we're no, it works, but it's slow, and it's not what they advertise.”
Josh Browder: Chat interfaces are terrible for travel AI applications
“It's good in some areas, terrible in others. I think for the travel use case, it's terrible.”
Browder: UK offers less competition for talent and media than US
“Starting out in the UK, it's kind of less competitive for talent, less competitive for media even. Like, anyone can get on the front page of the Daily Mail with the right story. The media in the US is much more jaded, so it's a lot more noisy, a lot more compe…”
Browder: US startup ambition and outcomes are 100x larger than UK's
“One huge negative is the scale of ambition in the US is a hundred times bigger. The most successful companies in the UK are in the, like, tens of billions range, like Revolut and great outcomes like that. In the US, it's in the trillions, and it's just an orde…”
Stebbings: San Francisco is the worst place to start a company today
“San Francisco is the worst place to start a company today because it is so expensive and difficult to acquire talent.”
Browder: San Francisco is far less socially stratified than London
“If you're just like moderately interesting, you can become friends with anyone in San Francisco. It's less stratified. In London, the rich keep to themselves in their fancy clubs. In San Francisco, you can play pickleball with anyone.”
Browder: Europe must dismantle ridiculous regulations to compete globally
“You have to get rid of these ridiculous regulations.”
Stebbings: Speedboat notary cost exceeded billionaire's German deal investment
“I tried to bring a billionaire once into a deal in Germany, and I had to send out a notary by speedboat, and it cost more than their investment to get their investment done.”
Josh Browder: Anthropic will reach $1 trillion in revenue
“I think Anthropic will get to a trillion in revenue.”
Browder: Ali Ansari is tech's most underrated CEO
“I would actually say Ali Ansari. I think he's in a very crowded space but he is a force of nature in terms of execution, and watch this space.”
Browder: Having billionaire professors teach small classes is unique to Bay Area
“Just the fact that you can have, like, billionaire professors teaching classes of 20 people is something that wouldn't exist anywhere outside of the Bay Area”
Founder gifted Browder shares in new startup after losing original investment
“They lost, I was a personal investment, one of my earliest investments. They lost my money. They went on to start an absolutely blockbuster company, and they gifted me the shares in the blockbuster company as if I had been an investor at the same price in, in …”
Browder: 75% of VCs invest only because someone else did
“Oftentimes they invest because someone else has invested. Oftentimes that's like, 75% of the time, I would say.”
Shorts cut from this episode
▶ Dropping out of college is overrated · 20VC with Harry Stebb (@19:10)
▶ You Can’t Leave Until You Raise A Seed Round · 20VC with Har (@9:38)
▶ We Turned The Facebook House Into A Growth Hack · 20VC with (@39:35)
▶ Why Most Founders Quit Too Early · 20VC with Harry Stebbings (@3:45)
▶ "I take all the money I make and buy land" · 20VC with Harry (@1:09:33)
▶ The one man accelerator at Four Seasons · 20VC with Harry St (@0:00)