Jun 28, 2024 · 1h 1m · news
Samir Vasavada: The Real Story of Vise: The Regrets, Mistakes and Mis-Hires | E1171 · 20VC with Harry Stebbings
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In this episode of 20VC, Vise co-founder Samir Vasavada candidly shares the lessons, psychological challenges, and operational missteps of scaling a billion-dollar financial technology startup as a teenage founder. He details the dangers of raising capital too quickly, mistakes in corporate executive hiring, and his eventual refounding of the company's culture and long-term vision.
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 11.4% of the talking time here. How this is scored →
Harry as informed peer 4.9 Guest teaching 2.8 Guest disagreement 0.9 Harry pushing back 3.0
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 38:05 Defiant reaction to selling investors
Samir forcefully rejects investors who lose faith and sell secondary shares, stating a blunt 'fuck you' reaction and resolving to make the company ten times more valuable without them.
Hardest push from Harry ▶ 19:15 Direct backchannel investor confrontationHarry aggressively pushes back on Samir's narrative by revealing direct quotes from Vise's own investors identifying hiring as the area where Samir severely messed up.
Biggest teaching moment ▶ 44:05 Preference stack vs valuation reframeSamir educates Harry on downside protection by explaining that preference stacks dictate real capital distribution far more than high headline valuations during downside scenarios.
Harry holds his own ▶ 13:50 Calling out venture 'foie grasing'Harry uses sharp venture terminology to label aggressive funding rounds as irresponsible investor 'foie grasing', forcing the guest to concede the point and adopt his framing.
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 Entrepreneurship and the Origins of Vise | 3 | 2 | 0 | 0 | Harry sets up the interview by asking about early money-making experiences and agrees with Samir's premise that great founders start young. Samir shares his early side hustles and coding apps at age 14. | |
| Securing the First Big 'Yes' | 6 | 2 | 0 | 1 | Harry demonstrates venture expertise by citing Keith Rabois' perspective on avoiding low-tier investors during early fundraising. Samir elaborates on how early angel checks from Nat Turner and Zach Weinberg enabled their Founders Fund seed deal. | |
| Pretzel Stations and Preempting Sequoia | 4 | 3 | 0 | 2 | Samir tells the story of meeting Sequoia at a TechCrunch Disrupt happy hour and taking a preemptive seed extension. Harry gently probes on why they accepted so much dilution across rapid funding rounds. | |
| The Regrets of Raising Too Fast | 4 | 3 | 1 | 2 | Samir admits that raising $130M in 18 months stripped away financial discipline and caused premature scaling. Harry asks directly where discipline was lost most, prompting a story about overpaying AWS. | |
| The Foie Grasing of Startups & Unrealistic Valuations | 6 | 3 | 1 | 4 | Harry strongly criticizes investor behavior, calling rapid consecutive rounds irresponsible 'foie grasing' of a startup. Samir agrees with taking ownership of the mistake while explaining how unrealistically fast growth expectations hurt the culture. | |
| The Psychology of a 20-Year-Old Unicorn Founder | 4 | 2 | 1 | 3 | Harry asks point-blank if becoming a 20-year-old unicorn founder made Samir get 'too big for your boots.' Samir candidly agrees, comparing the sudden status and power dynamic shift to a child-star phenomenon. | |
| The Major Reset & Remote Work Culture Pitfalls | 7 | 2 | 1 | 6 | Harry brings backchannel investor feedback directly to Samir, confronting him on hiring missteps. Samir acknowledges the severe hiring mistakes made during the pandemic boom. | |
| DEI Distractions and Customer Focus | 6 | 1 | 1 | 6 | Harry energetically interrupts Samir's description of corporate DEI and infrastructure discussions to challenge the lack of focus on revenue and customer acquisition. | |
| Board Dynamics and Filtering VC Advice | 7 | 3 | 2 | 6 | Harry challenges Samir's critique of venture capitalists by asking him to analyze VC incentives, while holding Samir strictly accountable for listening to bad advice. | |
| Ruthless Personnel Decisions and Firing Quickly | 4 | 4 | 1 | 2 | Samir outlines his philosophy on firing quickly, using a sports team metaphor instead of a factory model. Harry listens as Samir describes searching for candidates with chips on their shoulders rather than big-tech titles. | |
| The Folly of Burning $3 Million a Month | 5 | 2 | 1 | 4 | Samir details burning $3M monthly before executing a major workforce reset in early 2022. Harry adds a realistic counter-perspective, noting that such pivots only work when a company has a massive cash reserve. | |
| The Pressure to Exit & Sticking for the Long Term | 5 | 4 | 1 | 3 | Harry probes whether Samir was tempted to sell the business for $125M given liquidation preferences. Samir explains why he refused short-term exits in favor of building a platform-driven asset manager. | |
| Secondary Sales & Transfer Restrictions | 5 | 3 | 2 | 2 | Samir expresses a defiant attitude toward investors trying to sell secondary shares without believing in the company. Harry asks how founders should handle transfer restrictions and secondary dynamics. | |
| Founders' Liquidity and Zones of Reasonableness | 6 | 3 | 1 | 5 | Harry repeatedly presses Samir on whether he took personal liquidity during funding rounds. Samir shares taking ~$1M secondary to establish a financial cushion while keeping a chip on his shoulder. | |
| Preference Stacks, Dilution, and Changing Friendships | 5 | 4 | 2 | 3 | Samir educates on liquidation preferences versus valuations, showing why preference stacks matter far more. He also reflects on fair-weather relationships in Silicon Valley when a company cools off. | |
| Underwriting Incentives Over Emotions | 4 | 3 | 0 | 2 | Samir shares lessons on underwriting stakeholder incentives over emotions. He opens up about his lowest emotional point living in the Tenderloin and Crypto Castle while bootstrapping. | |
| Proving the Haters and Therapists Wrong | 6 | 2 | 2 | 5 | Samir reveals his parents hired a therapist to talk him out of dropping out of school. Harry challenges tiger parenting as groupthink and bad parenting, drawing on his own background leaving law school. | |
| Deeply Remembering Those Who Gave Up | 4 | 4 | 1 | 2 | Samir describes deeply remembering allies who gave up on him during hard times. He reflects on learning to internalize operational lessons firsthand rather than copying advice blindly. | |
| Quick Fire: Board Members and Key Advice | 4 | 3 | 1 | 3 | In quick-fire, Samir admits feeling trapped because his personal identity is completely tied to Vise. Harry pushes on whether Samir has separated identity from business, admitting he hasn't either. | |
| Leadership Growth and Team Empathy | 4 | 3 | 0 | 2 | Samir reflects on developing team empathy and transitioning from naive investor optimism to radical operational reality in board updates. | |
| The 10-Year Vision for Platform-Driven Asset Management | 3 | 2 | 0 | 0 | Samir summarizes his 10-year vision to build a platform-driven asset manager replacing traditional mutual funds and ETFs. Harry wraps up the conversation warmly. |
Statements from this episode (44)
Vasavada: Became Youngest Founder of $1B Business at Age 20
“I was like the youngest person in history to have a billion dollar business. I think I just turned 20 when our company was valued at a billion dollars.”
Vasavada: Raising $130M in 18 Months Was Bad for Vise
“So we raised something like a 120, hundred and thirty million dollars in an 18 month period. And that was a bad thing.”
Vasavada Earned $30,000 Building Apps by Age 14
“We made like 30 grand by the time we were 14, which felt like a ton of money.”
Stebbings: No Great Entrepreneurs Made Their First Money at McKinsey
“No great entrepreneurs came out of Harvard, Stanford, Oxford, Cambridge, Went to McKinsey and that's where they made their first money.”
Vasavada Dropped Out of High School to Build Vise
“I had actually dropped out of high school to build this business and moved to the Bay Area.”
Nat Turner and Zach Weinberg Were Vise's First Investors
“And the first investors that actually said yes were these guys, Nat Turner and Zach Weinberg, who started a company called Flatiron Health and sold it For a bunch of money to Roche and they actually went to Penn, and they're like, look, we had a similar story …”
Vasavada: Keith Rabois Would Not Have Responded to Cold Outreach
“I don't think Keith would have responded to a cold message. Maybe he would have, but that was really helpful, having them on board.”
Vise Co-Founders Paid Themselves $20K Annually Before Sequoia's Investment
“My co-founder and I were paying ourselves, like, 20 grand a year”
Vise Raised Seed Extension, Series A, and Series B in Seven Months
“The seed extension was done in October of 2019. Our A was done in March, and our B was done in May.”
Vise Was Sequoia's Last Investment Before the COVID-19 Shutdown
“We were the last investment at Sequoia before everything shut down for the pandemic, like day before the global shutdown.”
Vasavada: Concentrating Board Ownership in One VC Suppresses Healthy Debate
“You want multiple voices in the boardroom, and I think the challenge is when you have One investor that owns 30% of the company and, you know, has piled in, you know, close to fifty million bucks, then you're going to have that investor's perspective as, you k…”
Vasavada: Scaling Headcount From 6 to 100 Slows Startups Down
“We had gone from, like, six people to, like, a hundred people overnight, basically, and A hundred people don't actually make your business move faster. It actually slows you down.”
Vasavada: VCs Maintain Flawed Ethos That Startups Must Scale Quickly
“VCs have built this ethos that if it doesn't get big fast, it's never going to get big.”
Vasavada: Businesses Built Overnight Lack Defensible Competitive Moats
“If a billion dollar business is built overnight, it means someone else can go build that same billion dollar business overnight, and you don't actually have a moat.”
Vasavada: Premature Unicorn Status Attracts Corporate Recruits Over Builders
“The type of people you recruit when they see that you're a billion dollar business aren't focused on, we have a value advice called burn the boats. They're not focused on burning the boats. They're focused on a stable career and growing within an organization …”
Vasavada: Vise Was Among the First Tech Startups to Execute a Reset
“And I ended up being right because when, before the market really took a turn, we were one of the first companies to do a major reset. And it was more painful because other companies weren't doing it, but it ended up positioning ourselves so significantly bett…”
Vasavada: Early-Stage Startups Should Not Be Run Remotely
“I don't think startups should be run remotely. Like, you can't build culture when, you know, people are, you know, all on Zoom all day. Like, you build culture at those water cooler moments and in the team”
Vasavada: Vise's Entire Executive Team Turned Over Within 12 Months
“And we did this, like, five, six, seven times over with the executive team that fully turned over in, like, 12 months.”
Vasavada: Vise Skipped Interviewing Early Execs and Only Pitched Them
“And we weren't, we didn't even interview them. Like, we were just in sell mode the whole time. We got We got our investors in sell mode. We were just trying to convince them to join.”
Vasavada: Vise Leadership Meetings Were Consumed by DEI and Infrastructure
“When we went into our leadership meetings, we weren't talking about we weren't talking about that. We were talking about making infrastructure decisions that will matter in 2026 and rewriting our code to better position ourselves four or five years down the li…”
Vasavada: Big Tech Executives Lack Product-Market Fit Experience
“None of these people had to go out and find product market fit. They came into companies where there was already product market fit, and they just had to operate their little part of that company, or big part of that company, where they were kind of keeping it…”
Vasavada: VC Board Member Sean Acted as a Shadow Co-Founder
“Sean rolled up his sleeves, worked super hard. That guy is a total, like, just grinds. Like, I think he was like a shadow third co-founder.”
Vasavada: 99% of Startup Advice Given to Founders Is Bad
“You don't get enough advice, and then you start getting capital, and you have stakeholders, and you get too much advice, and the problem is a lot of this advice is either bad advice, 99% of the advice is bad advice, and then the rest of the advice is contradic…”
Vasavada: Firing an Employee Was the Right Decision 99.9% of the Time
“Like, I've never once, actually one exception, but I've, most of the, 99.9% of the time, never regretted letting someone go. It was almost always the right decision.”
Vasavada: Big Tech Managers Lack the Ruthlessness Required for Startups
“A lot of managers, especially ones that come from bigger tech companies, where there are these, like, kind of legacy HR policies you know, they're just not as ruthless with headcount and personnel decisions as they should be”
Vasavada: Vise Burned $3 Million a Month at Its Peak
“We were probably burning three million a month.”
Vasavada: All Asset Managers Will Transition to Personalized Software Platforms
“All asset managers will have to become platform companies, right? Investment advice will no longer be delivered through people and investment products. It will be delivered through platform in a personalized way at scale for Every single investor.”
Vasavada: Incumbent Asset Managers Lack the DNA to Build Great Software
“The DNA of these incumbent asset managers is not to build technology. It's not to build great product. It's not to build great software. And I know that because I spent times with these senior leadership teams at every single large asset management company. Th…”
Vasavada: Use Transfer Restrictions to Block Unknown Buyers in Secondary Sales
“Well, you don't want investors, like if an investor wants to sell, you should let them sell, but you need to know who's buying the stock because the worst case scenario is you let the investor sell to some rando and that rando ends up being a pain On your cap …”
Vasavada: Top VC Backing Can Attract Employees Seeking Quick Exits
“So it's a double-edged sword. And the reason why it's a double-edged sword is because on one hand, you've got all this great credibility by association. You have all of this social capital and that social capital allows you to hire people. It allows you to get…”
Vasavada: Modest Secondary Liquidity Is Critical for Founder Decision-Making
“It was, I think, for a founder to get a little bit of liquidity is really, really important in terms of long-term decision-making. Because from an incentives perspective, if you're a founder and you've got a hundred percent of your, you know, net worth in, in …”
Vasavada: Selling More Secondary Stock Would Have Been the Smart Financial Move
“I think it would have been a smart personal financial decision, and it's clear that a lot of other founders took, you know, sometimes a hundred million dollars of secondary. But so maybe from a personal financial decision, it would have been the risk-adjusted …”
Vasavada: Having $10 Million in the Bank Makes It Hard to Stay Hungry
“And I think if you have ten million bucks in the bank, like, it's just hard to be, it's hard to be miserable.”
Vasavada: A Startup's Preference Stack Matters More Than Its Valuation
“What matters more than your valuation is your preference stack, right?”
Vasavada: Investors Pretended to Be Friends Until Vise Stopped Being Hot
“Some investors, I think, pretended to be our friends. And, you know, when incentives were flipped or we weren't as hot, I think they weren't our friends anymore, and I think that hurt because I thought those people were truly our friends.”
Vasavada: Founders Should Underwrite Stakeholders' Incentives, Not Their Emotions
“The mistake I made was underwriting people's emotions, not their incentives. And I was like, oh, this person is saying this particular thing to me. They feel this particular way. I don't want them to feel this particular way. I'm going to say this particular t…”
Vasavada Lived in SF's Crypto Castle With 12 People at Age 16
“So, like, there was a point in time, I was 16 years old. I was living in San Francisco. I was living in the Tenderloin, and then I moved to this house called the Crypto Castle. I was living with 12 people. We shared one bathroom.”
Vasavada: Parents Hired a Therapist to Stop Him From Running Vise
“There's a point in time where they had hired a therapist To talk me out of running the business and just be a normal kid.”
Vasavada: Investors Who Give Up Hurt More Than Initial Rejectors
“I think it's not necessarily the people that gave me no's, it's not the people that, like, didn't believe on me in the beginning. I think it's the people that gave up on me.”
Stebbings: Founder Obsession Is Necessary, Making Detachment Impossible
“It's unhealthy, but I think it's a necessity. It's like obsession is a necessity and it's very difficult to be obsessed and detached at the same time.”
Vasavada Admits He Was Overly Optimistic With Early Investors Due to Naivety
“I think it was too optimistic early on, and I think now I see a deep sense of reality. And part of why I was very optimistic is just because I didn't know any other way to be. Like, I was just very, like, I was naive, and as a result of being naive, I was very…”