The Twenty Minute VCSamir Vasavada: The Real Story of Vise: The Regrets, Mistakes and Mis-Hires | E1171
EVERY SPOKEN WORD
130 min read · 25,917 words- 0:00 – 1:01
Intro
- SVSamir Vasavada
I, I was like the youngest person in history to have a billion-dollar business. I think I'd just turned 20 when our company was valued at a billion dollars. So we raised something like 120, $130 million in an 18-month period. (glass shatters) And that was a bad thing.
- HSHarry Stebbings
Do you regret raising as much money as quickly?
- SVSamir Vasavada
Yes, 100%.
- HSHarry Stebbings
Why? I spoke to some of your investors, and this is one area where Sami fucked up is hiring.
- SVSamir Vasavada
Oh. Big time.
- HSHarry Stebbings
Did you sell secondary?
- SVSamir Vasavada
Of course, a small amount.
- HSHarry Stebbings
Do you regret not selling more? With Lip Graphs, you've got to sell for $125 million.
- SVSamir Vasavada
Yeah. We would have sold for more than that.
- HSHarry Stebbings
Were you tempted to sell for that?
- SVSamir Vasavada
Tempted? Did I think about it? Yeah, of course.
- HSHarry Stebbings
Do you think people stabbed you in the back?
- SVSamir Vasavada
Um... (beeping)
- HSHarry Stebbings
Ready to go? (instrumental music plays) Sami, I'm so excited for this, dude. It's wonderful to have you in the studio in person.
- SVSamir Vasavada
Yeah. Thank you so much for having me.
- HSHarry Stebbings
Not at
- 1:01 – 3:45
Starting Vise
- HSHarry Stebbings
all, my man. But I wanna start with the beginnings of Wise. Like, what was the a-ha moment for you with Wise? And just take me back to that.
- SVSamir Vasavada
So I think it's less the beginning of Wise and more the beginning of our entrepreneurial journey. I think what's unique is, I started my first startup at 12. Um, I was, I was at this summer program at Northwestern. And my parents were like, "You cannot go to traditional summer camp."
- HSHarry Stebbings
(laughs)
- SVSamir Vasavada
"Uh, you must do college courses." So from, like, sixth grade onwards, they sent me to this college summer program at Northwestern. And one year, I think it was the summer of eighth grade, I met this kid Runic. And he was this kid ac- across the hall from me. And we're like, "I'm from Cleveland," he's from Detroit. We're like, "We're so bored in the Midwest. School's, like, pretty easy." And, like, the iOS programming language, Swift, had kinda came out recently and it just started taking off. And we're like, "Let's build apps for small businesses. Let's learn how to code. Let's use Swift, and let's build apps for any small business that wants an app." And that was kinda how we got our start to our entrepreneurial journey. We started with a game, and then we built an app for a chain of car washes. We built a g- uh, an app for a medical conference. All kinds of different apps. We made, like, 30 grand by the time we were 14, which felt like, like a ton of money. Felt like we were rolling in it. And my co-founder got a research opportunity with a prestigious university, um, in AI research, because he was a longtime math researcher. He was doing ra- math research in, I think it was graph theory, and it translated f- quite well over to AI research. And we realized, "Well, what if we could use AI to build apps? What if any small business could type in their app idea in our system and we could use AI to build an app?" And that was our, our first real startup idea. The challenge was the team we got to work with us was the wrong team. It was people we can r- we met on the internet. We blew all the money we built maki- making apps for small businesses on kind of trying to fund the startup, and the technical challenge was way harder than we could have ever imagined it to be. Um, so unfortunately, that was our first failure, but it opened us up to this idea of AI quite early on, and, you know, got us all hyped on the idea of building a startup.
- HSHarry Stebbings
So it's funny, whenever I meet founders today, Sami, I always say, "How did you first make money?" Because I never th- I, I always believe that the best entrepreneurs start early. You know, great entrepreneurs came out of Harvard, Stanford, Oxford, Cambridge, went to McKinsey, and that's where they made their first money. It's always starting something very early. Do you agree with that? Does it...
- SVSamir Vasavada
I... 100%. I think it's just having that, like, motivation, like, the, that passion motivation that's developed early. So I think in our case it was building apps, but even before that, I was, like, obsessed with garage sales.
- HSHarry Stebbings
Nice.
- SVSamir Vasavada
Like, I would go to my grandma's house and, like, find all of her junk and, like, try and sell it at garage sales. And, like, that was the thing I did when I was, like, s- you know, single-digit age.
- HSHarry Stebbings
(clicks tongue) How old were you when you started Wise?
- SVSamir Vasavada
I was 15 and a half
- 3:45 – 7:16
The First Big Yes
- SVSamir Vasavada
when I started Wise.
- HSHarry Stebbings
15 and a half. Okay. Who was the first big yes to you at Wise?
- SVSamir Vasavada
That's actually funny. So I think there's two stories here. I think the first is, our team early on, we didn't have that much money. We were consulting with these financial institutions, which is how we discovered the need, the problem, to deliver personalized portfolio solutions in an automated way to, uh, financial advisors. We were actually consulting with these big financial institutions on AI. And, but we didn't have, like, a ton of money to actually pay people to, like, build us the product. So, you know, outside of us doing it ourselves, we found a team of engineers, um, mostly just through scraping AngelList and cold emailing people and reaching out to people on LinkedIn. Like, if you go through my LinkedIn in 2014, 2015, 2016, it's just, like, hundreds of cold messages. Um, we got the first, like, two engineers to say, "Oh, yeah, I'll, like, work on this on equity nights and weekends." So that was the, that was the first big yes. And that was able to help us build our MVP and, you know, get the first product to market. Um, and then our second big yes was actually, so my co-founder decided to go to college, which was a real challenge for me, because I had actually dropped out of high school to build this business and move to the Bay Area. I was living in the Tenderloin, um, trying to, trying to bootstrap it to then raise capital. And my co-founder decides to go to UPenn. And at UPenn, I'm like, "Well, if, if he doesn't drop out of UPenn, then I don't know how I'm gonna grow this business. I don't know how, how we're going to make this thing work." He's like, "Well, in order for us to do it, we need to raise some capital." And we'd called all these investors and cold emailed a ton of people, and no one wanted to give us money. They're like, "What k- what business do you kids have building wealth management software?" 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. Um, and they actually went to Penn, and they're like, "Look, we had a similar story to you guys." They actually did complete Penn, but that 100K...... an, an investment which, you know, looking back, it's a small investment, but, like, that was the reason why we were able to keep going. It was a-
- HSHarry Stebbings
Was that a big unlock to further money?
- SVSamir Vasavada
... this really meaningful deal.
- HSHarry Stebbings
I think people forget the, the multiplier effect of a yes from an important group of people or person like Nat and Zach. Actually, when people say, "Oh, Nat and Zach are in," it's like, "Oh, well, fuck it, I'll do it."
- SVSamir Vasavada
Yeah.
- HSHarry Stebbings
Yeah.
- SVSamir Vasavada
It was super important. I think having them introduce us to people, like, I didn't know the power of a warm introduction until after that. It helped us get, you know, Founders Fund, who ended up leading that seed round and Keith being one of his first investments at Founders Fund, partially through a warm introduction. Um, I don't think Keith would've responded to a, to a cold message. Maybe he would have, but, um, that was really helpful having them on board. And I think that that, like, aha click of, like, someone in Silicon Valley actually believes in this, was a really helpful motivator for us.
- HSHarry Stebbings
It's funny, Keith always says, actually, "There's no point in going to a load of crappy investors first, 'cause they'll ask very different questions to what, like, a great investor would ask." Have you found that the great investors ask different questions?
- SVSamir Vasavada
It's interesting because all the investors that ended up investing in Vize were all the great investors. Like, I don't think we have any crappy investors on our cap table. And all the crappy investors, for some reason, passed.
- HSHarry Stebbings
Mm-hmm.
- SVSamir Vasavada
Um, so maybe they saw something that the, the, the crappy investors didn't see, but it... For, for the most part, they, they asked better questions, they understood things faster, but I think they were able to pattern match more effectively from successes they had seen, um, and successes they had been a part of, to what we were doing, in a way where, you know, a crappy investor might not have been able to as effectively pattern
- 7:16 – 11:15
How the Sequoia Deal Went
- SVSamir Vasavada
match.
- HSHarry Stebbings
How did the Sequoia deal come about?
- SVSamir Vasavada
This was actually kind of funny. So I... We'd already gotten Founders Fund, and we're like, "Well, we're just gonna build this business. We don't need to raise more money." Like, this is not, this is not really that important to us. Um, we don't need more VCs. We stopped talking to VCs. We're just like, "We're gonna build this business." But I had seen the show Silicon Valley as a kid, and I was like, "I wanna do Startup Battlefield." And, like, Founders Fund was like, "This is like a waste of time. What are you guys doing?" They're like, "Focus on your business." And I'm like, "No, I really wanna do this Startup Battlefield thing. I think it'll be fun." So I apply for Startup Battlefield, I get into Startup Battlefield, um, and to, you know, do the pitch at TechCrunch Disrupt, and they're... The night before the pitch, they're having a happy hour at Sequoia Capital's office, and I'm like, "I don't really know if I'm gonna go or not." But my co-founder and I were paying ourselves like 20 grand a year, and we were looking for free food anywhere we could find it, and there was free food at this happy hour, and it was like a 10-minute walk from our house, so we're like, "Okay, we'll go to this happy hour, we'll eat some free food. We don't really need to talk to Sequoia because we have Founders Fund and we're just gonna keep building our business." So we're sitting at the pretzel station at the Sequoia office. Everyone's like rushing up to Roelof and Mike Moritz and, you know, all these famous partners there, and we're just sitting at the pretzel station chopping up pretzels, and this, like, guy who, like, looks really young walks up to us and he's like, "What are you two schmucks doing?" Like, "How old are you guys?" Like, "Who are you?" And we start talking about Vize and what we're building, and he's like, "Look, like, you know, it's fascinating because I was at this retreat with the Collison brothers, you know, a couple weeks ago, and they were talking about, like, a truth that the mass doesn't necessarily believe to be true, but they believe to be true, and it was that financial advisors will continue to exist, and that the relationship is really important. So, like, this actually makes a lot of sense. Like, I get the story you guys are going after." So then we, we pitch at Disrupt and he's like, "You guys should come in and, like, meet the partnership and, you know, talk about what you're doing." And they'd actually made an investment in a company called FutureAdvisor, which was one of the early robo-advisors at the time, which got acquired for a couple hundred million bucks by BlackRock, and the founder of FutureAdvisor was an investor of ours, and he called the Sequoia partnership separately and was like, "Hey, if I were to have kept building FutureAdvisor, Vize is taking the direction that we could have never gotten to." And having that kind of piece of credibility was really helpful going into the investment process, so, so, uh, they decided to kind of preempt us on a, uh, on a seed, on like a seed extension round, and we're like, "Oh, I guess we'll, I guess we'll take it. Why not?" "It doesn't, doesn't, doesn't hurt." And, uh-
- HSHarry Stebbings
They then doubled down also. I remember-
- SVSamir Vasavada
They tripled down. (laughs)
- HSHarry Stebbings
Tripled down.
- SVSamir Vasavada
Which I don't know if had happened before in Sequoia. Um, maybe, maybe it had, I think in Stripe and a few other instances.
- HSHarry Stebbings
Why did you say yes to that? I know it sounds stupid. Obviously, Sequoia are an incredible firm, but, like, it just means they own a lot of one's business. What was the thinking around the tripling down and...
- SVSamir Vasavada
So, uh, they... I think as we started to build, and like... And they, they tripled down in a short period of time. So the seed extension was done in October of 2019. Our A was done in March and our B was done in May, and it was kind of-
- HSHarry Stebbings
What, what year was this?
- SVSamir Vasavada
This was all... This is 2020, so this is after... This is... Venture deals are not getting done right now. The world shuts down. We were the last investment at Sequoia before everything shut down for the pandemic, like day before the global shutdown, um, happened. And I think that for us, I think for both Sequoia and I, we... And, and Runa, we saw that, you know, this thesis was starting to pan out. We were getting early customer feedback. It was coming in extremely positive. We were getting a lot of positive reception. Um, it, it just started to seem like all of these dynamics that we thought were going to be true started to play out and start to be true, which gave them more conviction. And then for us, we also realized, okay, if we're actually gonna build this and scale this, we need a lot of capital. At least we... At the time, we thought we needed a lot of capital. Um, and-
- 11:15 – 19:15
Does Samir Regret Raising Significant Funds Early On?
- SVSamir Vasavada
- HSHarry Stebbings
Do you regret raising as much money as quickly?
- SVSamir Vasavada
Yes. 100%.
- HSHarry Stebbings
Why?
- SVSamir Vasavada
Um, and I also re- regret raising it all from the same firm, to some of the points. I love Sequoia, I think they're great, but 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 50 million bucks, then you're gonna have that investor's perspective as, you know, the predominant perspective, um, versus having some, you know, healthy debate, which I think is really important. Um, and I think, two, the challenges... So we raised something like a hundred and-... 20, 130 million dollars in an 18-month period. I think we went from a seed stage company to unicorn. It was probably, like, one of the fastest examples at the time in history of that having happened. Um, and that was a bad thing, and the reason why that was a bad thing is because, one, when you have a lot of capital, you lose discipline, right? When y- e- when decisions no longer have, like, you're not, you don't have this, this existential threat of dying in six months, like, you, you lose a little bit more discipline. And I think we grew-
- HSHarry Stebbings
Where did you lose discipline most?
- SVSamir Vasavada
I mean, specifically around spending, like, we hired a lot of people. Um, we, like, I remember, I remember, like, and again, this is to Delian's credit, but we, I call Delian one day, we had lost, like, AWS, we overpaid AWS by $4,000.00. And I'm like, "Delian, do you know anyone at AWS who can get us a refund for this $4,000.00?" And he's like, "Dude, we gave you a seed round so you don't have to, like, worry about these things. Just lose the $4,000.00 and, like, focus on growing really fast." And we're like, "Okay, like, I guess money doesn't really matter. We're gonna just focus on growing really fast." And I think that was, um, I think we learned the w- wrong lesson in that, and I think money does really matter and being financially disciplined really, really matters. And I think even more importantly than that, when you hire, when you lose that discipline and you hire all of these people, like, we had gone from, like, six people to, like, 100 people overnight basically. And 100 people don't actually make your business move faster. It actually slows you down. You have to deal with HR problems. You have to deal with all kinds of different perspectives on how to build. You have to deal with, you know, a whole myriad of different things with more people versus having a strong density of really, really smart people that are all problem-solving and helping you get to that next incremental milestone as opposed to dramatically scaling your organization for the s- scapes- the sake of scaling your organization.
- HSHarry Stebbings
Do you blame the investors? Like, I'm an investor today, and, like, uh, to me, that's irresponsible foie gras-ing of a company is what I would call it.
- SVSamir Vasavada
Uh, yeah, you're foie gras-ing a company. I'm gonna steal that term. Um-
- HSHarry Stebbings
Yeah, uh, you are shoving cash down a company. I mean, three rounds in six months is fucking ridiculous.
- SVSamir Vasavada
(laughs) Yeah, I mean, I guess to a certain extent you can blame the investors, but at the end of the day, like, I'm the one as the founder who made the decision, so I have to take ownership and accountability for it. I think I learned a lot in the process.
- HSHarry Stebbings
Was the valuation a problem?
- SVSamir Vasavada
No.
- HSHarry Stebbings
It wasn't?
- SVSamir Vasavada
The valuation, I think the expectations of the valuation was a problem. I think that-
- HSHarry Stebbings
What was, what was tied to the expectations of the valuation? Mm-hmm.
- SVSamir Vasavada
Just growth that was unrealistic. Like, companies, I think VCs have built this ethos that if it doesn't get big fast, it's never gonna get big. And the problem with that was, and we were getting big p- pretty fast, but, like, uh, to grow into a, you know, a billion-dollar valuation in 18 months from being a, p- from having our founders fund it around at like four million, right, is just, like, not possible. Like, e- d- l- ye- it's, it is un- unrealistic. Um, I think, I, and especially in a market like ours where it is just a slow-to-change market, but billion-dollar businesses aren't built overnight, right? And the m- the bigger problem is that 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. Um, so I- I actually think that the expectations it created for us were- were- were a bad thing. Um, I think 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 and, like, assessing you alongside Google when, you know, you're really, like, this seed series A stage company. You're not Google, and the, there's gonna be a lot of ups and downs and things that need to be figured out that, you know, w- a- a- a true billion-dollar company wouldn't have to figure out.
- HSHarry Stebbings
Did it impact your psychology and did you get too big for your boots?
- SVSamir Vasavada
100%. Like, when I was, I- I- I was, like, the youngest person in history to have a billion-dollar business. Like, at 20 years old. I think I just turned 20 when our company was r- valued at a billion dollars. Like, we had, like, all of these, b- every day would be a different billionaire or celebrity or someone hitting me up saying, like, "I wanna invest in your company." Like, it was just this change, like, it was a change in power dynamic. It was, it was definitely, it's not healthy. It's like, it's like a child star phenomenon. It's, like, not healthy for- for anyone to- to- to go through that.
- HSHarry Stebbings
How did you respond to that?
- SVSamir Vasavada
So, I stayed relatively grounded in the sense, like, I don't drink. I don't do drugs. Like, I- I was able to stay, like, I had a set of core principles that I, you know, fairly well adhered to and stuck to, um, you know, throughout my entire life that I think was important, you know, was maintained. I think the challenge was I really deeply valued money, like, and being very frugal and, you know, you c- you can't really take- take the Indian out of me. Um-
- HSHarry Stebbings
(laughs)
- SVSamir Vasavada
... not to be too politically incorrect, but I think that was a little lost and I had to relearn that. But it was, uh, it was definitely an experience. It was definitely a wild experience.
- HSHarry Stebbings
What brought you back down to Earth?
- SVSamir Vasavada
Seeing all the other founders. This wasn't, like, a unique-to-me thing. I hung out with a bunch of other founders that were also, you know, young-ish that, you know, built decacorns or, you know, billion-dollar businesses, so to speak, overnight. And I think I saw the way they acted and, you know, the way they behaved, and I was just like, okay, like, this just doesn't really make a ton of sense to me. Like, there's something off. Like, if something doesn't necessarily feel quite right, then, like, you kinda re-underwrite your thinking. You re-underwrite your decision-making. Like, it didn't make sense in 2021 for there to be a new unicorn every couple of days-
- HSHarry Stebbings
Mm-hmm.
- SVSamir Vasavada
... you know, reading in Tech Crunch. Um, I just, it, everything felt off. And I think because it felt off, I was like, okay, I think, one, this is gonna come down and there's gonna be a deep major correction, and I think, two, um...I, I don't like this feeling of feeling off. Like I, I, maybe I have to change my actions, the way I'm thinking, the way we're spending our time as a, as a company, um, to re-account for it. 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. Um, and it was more painful because other companies weren't doing it, but it ended up positioning ourselves so significantly better given that we had done it.
- HSHarry Stebbings
What was involved in the major reset?
- SVSamir Vasavada
It was... first, re-underwriting our culture. And I think building a company in the pandemic adds a complete new level of challenges because you are building a company in an all-remote environment. And to be frank, I don't think startups should be run remotely. Like I... 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, and it felt like our entire culture was off. Um, was one. I think the second was we just recruited a lot of people that were mercenaries. They weren't missionaries.
- 19:15 – 38:29
Mistakes & Lessons on Hiring
- SVSamir Vasavada
- HSHarry Stebbings
Well, let's talk about that because I, I, I did speak to some of your... I mean, it's... (laughs) depends, uh, how harsh you want me to be. I spoke to some of your investors and this is the one area where some of it fucked up is hiring.
- SVSamir Vasavada
Oh, big time.
- HSHarry Stebbings
Talk to me about that. Like, what did you get wrong-
- SVSamir Vasavada
But, like, I corrected it.
- HSHarry Stebbings
... and what did you do to correct it?
- SVSamir Vasavada
One, e- every founder early on, like, especially as you raise all this money and you start to scale is like, "I need to scale. Okay, like, who do I need to take... like, who do I need to involve when I scale?" And I think all the investors are like, "Okay, well, you guys are young. You guys need senior executives, and senior executives will give you the leverage to be able to grow your team, to be able to manage more effectively." And those senior executives have usually run a big team before and they've come from a big company. And w- we recruited a lot of senior executives that, one, they didn't understand the financial advisor, the customer-
- HSHarry Stebbings
Who told you to get senior execs?
- SVSamir Vasavada
Other venture capitalists and founders.
- HSHarry Stebbings
Okay.
- SVSamir Vasavada
Um, so people in the Silicon Valley ecosystem. Um, it just... it felt like the thing to do.
- HSHarry Stebbings
Mm-hmm.
- SVSamir Vasavada
So then you bring on an executive recruiter. The executive recruiter puts 20 candidates in front of you. They say, "Hey, all of these 20 candidates have 25 offers. They've got more offers than they know what to do with. You need to sell. You can't even be thinking about interviewing. You need to be selling. And then if you get this person, you'll be super lucky and great." And we did this like five, six, seven times over with a executive team that fully turned over in like 12 months, and it was all people from big tech, all people that ran big orgs at companies like Dropbox, at companies like TripActions, at- at companies that were... you know, they were at Twitter, Meta, places like that, and they run 100, 200, 300-person orgs, and, eh, we- 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. It was such a hot market that we get this whole group of people.
- HSHarry Stebbings
Did it feel wrong in the moment?
- SVSamir Vasavada
Yes, but it felt like the thing to do. It... everyone was telling us that was the thing to do, and our mindset at the time was, "All of these people are so much smarter than we are. They have so much experience. We are gonna do... we are gonna do what they say to do, um, because it feels like that's the right thing to do."
- HSHarry Stebbings
How quickly did it become apparent that it was not the right thing to do?
- SVSamir Vasavada
Pretty quick. Like, I would just come to work every day miserable. (laughs) Um-
- HSHarry Stebbings
Why?
- SVSamir Vasavada
Because we... it felt like, one, we weren't working on the right things. We were talking so much about how to make people feel heard, how to make people feel valued, how to be inclusive, and how to create a super, like... you know, just like things that, like, just quite frankly don't matter. What matters are can we build the best possible product such that our customers, you know, will, will buy it and keep buying it and refer all of their friends to buy it. Um, and we weren't talking about... like, when we went into our leadership meetings, we weren't talking about, uh, 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 line. We were talking about making, you know, different executives or different managers or sub-managers in the company feel better and feel more included. We were talking about, you know, DEI. We were just... we weren't talking about our customers and their problems and how to build our product to better suit our customers and their problems.
- HSHarry Stebbings
Do you understand? We need to get fucking customers. We need to get some revenue. Like what the fuck is this stupid infrastructure discussion that we're having, whether it's, you know, uh, like, the culture of a firm that's got few customers or it's infrastructure problems for 2026. Like, is no one going, "Hang on a minute, what the fuck is going on?"
- SVSamir Vasavada
No-
- HSHarry Stebbings
(laughs)
- SVSamir Vasavada
... because when you raise so much capital so quickly and you have all of these great investors on your cap table and everyone says this company is the shit, like you just think that it works. And like you, you've been at companies where you didn't actually have... 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 status quo. Most of these companies that they came from were just like... th- they haven't grown very much, like they're just there and they're operating and they're running their part, but like none of them had to find product market fit. So they just assume, "Okay, when I come, this company's already got it figured it out. I'm just gonna do the same thing I did at X company. I'm gonna run my playbook that I did at X company and I'm gonna bring it over to Vice." And you've got all these people with playbooks versus first principle thinkers that are trying to actually understand the problem and problem solve with you, um, to actually drive product market fit. So it felt like that was the case, and we, we, we got so much pressure on us at the time that it was like, "M- m- you know, we have to keep these people happy. They're gonna solve our problems." That's why you bring executives in. And it was pretty apparent that that wasn't the case.
- HSHarry Stebbings
When did that start turning? Like when was it apparent? Three months in, six months in, a year in?
- SVSamir Vasavada
Yeah, it was pr- uh, probably three to six months in. We thought it w- I think we were too optimistic at the time. So three months in, we're like, "This is...... a problem. Six months in, we're like, "Okay, this is broken." And like, I think we were optimistic of-
- HSHarry Stebbings
Are you talking to the board about it at this point going, "This is not working"?
- SVSamir Vasavada
I think the board was kind of like, "You got to figure out how to make these people happy and like you," um, at the time.
- HSHarry Stebbings
Mm-hmm.
- SVSamir Vasavada
That changed. I think the board, as the market started to change, I think the board started to realize, "Okay, we actually need to make some changes as a business."
- HSHarry Stebbings
Did you feel that you could talk to the board?
- 38:29 – 39:07
Advising Founders on Transfer Restrictions & Investor Exits
- SVSamir Vasavada
on the cap table.
- HSHarry Stebbings
Okay. So when you think about like advising founders today, what would you advise them on transfer restrictions and how they engage with investors who wanna sell?
- SVSamir Vasavada
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 table. Um, and like they are someone you don't want on the cap table. Like, I wouldn't necessarily want an investor selling to an investor I didn't know and wasn't comfortable having on the cap table. So I think that's where, that's why you have the transfer restrictions in place.
- 39:07 – 45:02
The Dual Impact of High-Profile Investors on Startups
- SVSamir Vasavada
- HSHarry Stebbings
When you think about like the impact of investors, you know, I think people often say an investor doesn't make a company, whatever, whatever. Like the brands of Founders Fund and Sequoia make a big difference. To what extent do they negatively versus positively impact the trajectory of a company?
- SVSamir Vasavada
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 great customers, it allows you to get in the press, it allows you to raise money from other investors. Everyone pattern matches to what is Sequoia f- what is Founders Fund? What are these prominent investors doing? The reason why it's a double-edged sword is a lot of people see it as their, you know, especially prospective employees see it as their get rich quick, you know, like, "This company's a rocket ship. They raised all this money from Sequoia, I'm gonna go join and it's gonna work and I'm gonna be, it's gonna be awesome." Right? And it's an attractor for talent. And oftentimes this is the wrong talent for your business. Um, and you need to be extra mindful of, "Is this person joining my company because of my company and the mission?" And, you know, the, the, you know, some irrational motivator as to why they're gonna be really successful here. Or are they joining my company because they see it as a quick path to an exit, um, because Sequoia backed it. And you don't want those people that are just joining because of Sequoia.
- HSHarry Stebbings
Did you sell secondary?
- SVSamir Vasavada
Of course, a small amount. Um, I think that it's an un- like it was a, it was... I think for a founder to get a little bit of liquidity, um, is really, really important in terms of long-term decision making. Because from an incentives perspective, if you are a founder and you've got 100% of your, you know, net worth in, in this company and you know, you're going through hard times and like you're not sure if you can like afford rent or you are not sure if, you know, you can make it through some th- through some tough time, um, thus you wanna sell or you want to make kind of a personally wrongly incentivized decision, um, that can be dangerous. Like, it can, it can oftentimes force you to not want to take risk because you're just, you're, you're holding onto so much risk in the company. But I think there's a l- a zone of reasonableness, and I think like selling a million dollars of secondary, I think is reasonable for a founder to have a financial cushion. Uh-
- HSHarry Stebbings
Is that what you sold?
- SVSamir Vasavada
Aro- around there.
- HSHarry Stebbings
Do you regret not selling more?
- SVSamir Vasavada
It's crazy because I had offers to s- to, to buy a lot more secondary.
- HSHarry Stebbings
Yeah.
- SVSamir Vasavada
Um, I just, I didn't s- it just didn't make sense to me. Like one, we thought it was a bad look to our investors, um, like founders cash out all of this money in secondary. I think it would've been a, a smart personal financial decision. And it's clear that a lot of other founders took, you know, sometimes $100 million of secondary. Um, but, uh, so maybe from a f- a personal financial decision, it would've been the risk adjusted correct decision to make to have sold more secondary.
- HSHarry Stebbings
Do you think you would be a better leader today if you had taken more cash off the table then?
- SVSamir Vasavada
No.
- HSHarry Stebbings
Huh.
- SVSamir Vasavada
Um, I think the reason why is I don't, I, I met, uh, Jensen from NVIDIA-
- HSHarry Stebbings
Hmm.
- SVSamir Vasavada
... and he's like, "Look, like, y- in order to build like true resilience and to like, you know, continue compounding, y- y- you kind of need to be like, and you need to be comfortable being miserable." And I think if you have 10 million bucks in the bank, like it's just hard to be...... it's hard to be miserable. And like I think there are points in time where I was miserable, and that was like a deeply motivating factor. And I think that if I was just too comfortable, if I h- if I had all this money, if I had, you know, all the things that come with all of that money, maybe I just would have been too comfortable and I would've just not been willing to make the set of hard decisions I did.
- HSHarry Stebbings
That's interesting. Do you think money makes you happy then?
- SVSamir Vasavada
No. And it's funny-
- HSHarry Stebbings
But you said it's hard to be miserable with $10 million.
- SVSamir Vasavada
I think happiness and comfort are two different things.
- HSHarry Stebbings
Hmm.
- SVSamir Vasavada
Comfort can bleed- breed complacency. Right? Like, you're not... Like, and again, I think there's a zone of reasonableness, right? I think having, like, no money in the bank, being, like, borderline broke, um, uh, l- like, which is what- w- was our financial situation before we took a little bit off the table, um, is not good for you. Because you're not willing... Like, I think that, uh, I think having a little bit of money is- is like, is- is healthy, right? It is- it is- it is- it is healthy, it's good, you know you can sleep at night. I think having too much money is- is dangerous. At least too much money early on is dangerous. So I think it's about the- the- the general reasonableness. But I h- I had enough money to the point where I had the chip on my shoulder, I needed to prove, I needed to like prove that it could work, I needed to prove that I could build a big thing, but I didn't have so much money that I was like, "Okay, if this doesn't work, like, I'm comfortable, I'll buy a mansion and I'll screw off."
- HSHarry Stebbings
Do you worry about scaling into the valuation?
- SVSamir Vasavada
No. Because like why- why does it matter, right? It- it would matter if I had a massive preference stack above me. But because we have so much money in the bank and we don't burn very much, um, I don't necessarily have to... Be- what matters more than your valuation is your preference stack, right? If you've got a billion dollar preference stack, not a billion dollar valuation, and you go sell the company for $500 million, then you're still under water, right? If you don't have all that in cash.
- HSHarry Stebbings
Sure.
- SVSamir Vasavada
But if you have, you know, uh, a $120 million preference stack and you sell the company for $100 million, um, and you still have $80 million of cash, that's, you know, what is it? $60 million of value that goes to- that waterfalls to the whole cap table.
- HSHarry Stebbings
And so not worried about scaling into it?
- SVSamir Vasavada
No.
- HSHarry Stebbings
Good.
- 45:02 – 47:46
Losing Friends When the Company Cooled
- SVSamir Vasavada
dilute yourself.
- HSHarry Stebbings
Do you see investor engagement differ when you're not a hot company?
- SVSamir Vasavada
I wouldn't even say it's like investor engagement. I would say it's like, generally speaking, like I've learned a lot about people. Like, it's... And like I further affirmed my belief of like it's really important to have a core group of like close friends that are like your friends regardless, so your friends from when you were, uh, like a- a child, you know, onwards, that like is your true group of friends. Because like a lot of people are gonna come into your life and they're gonna come into your life for the wrong reasons, and I think a lot of people aren't aware of that. And when something starts to change, those people move out of your life, um, and you f- you know, you're like, "Well, like what, uh, did I do something wrong? Like was I a bad person? Was I..." But it's just like you're not- you're not the cool hot thing. They're gonna move on to like, you know, crypto's hot, they're gonna move on to the cool crypto guy. Now AI is hot, they're all gonna move on to the, you know, the- the big AI founders. And they're gonna just keep moving from cycle to cycle to cycle. They're gonna chase the hot thing.
- HSHarry Stebbings
Did that hurt?
- SVSamir Vasavada
I think for- for some people. Some investors, I think, pretended to be our friends, and-
- HSHarry Stebbings
(laughs)
- SVSamir Vasavada
... you know, when incentives were flipped or we weren't as hot, I think they- they weren't our friends anymore, and I think that hurt, because I thought those people were truly our friends. I think there were some set of people where I was like, oh yeah, it's just like, you know, it's the, like, none of this matters, it's just noise, right? At the end of the day, we're gonna compound, we're gonna build a big business. Like, them not liking us or them kind of losing some favor with us doesn't necessarily matter to us. I think people per- pretending to be your friends, pretending to deeply care about you, and then, you know- you know, stabbing you in the back in some way, shape, or form, or- or talking about that, I think really hurts.
- HSHarry Stebbings
Do you think people stabbed you in the back?
- SVSamir Vasavada
I think people definitely tried to at different points in time. Um, I think they just weren't successful.
- HSHarry Stebbings
What was the hardest element of the investor base then?
- SVSamir Vasavada
The mistake I made was underwriting people's emotions, not their incentives. And-
- HSHarry Stebbings
(laughs)
- SVSamir Vasavada
... 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 gonna say this particular thing so they feel happy." And like that's just like the wrong way to think. The right way to think is, "What are my incentives? What are their incentives? How do we get to a shared, you know, outcome to the common good, which is make our- increase our enterprise value of the business?" If it doesn't, right, if their incentives don't line with mine, right, then like I'm cognizant of it, I can replay back why their incentives don't necessarily align with mine, but like I'm gonna do the right thing for the company. I'm not gonna like, I'm not gonna like try and change myself or my emotional state or change something about the business to make that
- 47:46 – 55:40
Samir's Period of Depression
- SVSamir Vasavada
person feel happy.
- HSHarry Stebbings
Did you go through periods of depression?
- SVSamir Vasavada
Yes. But nothing dwarfs... 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. Um, I was living with 12 people, we shared one bathroom, my parents didn't really like me 'cause I dropped out of school, my co-founder was still in high school, um, moving on to college. Like the business was kind of working, it wasn't really working, we were bootstrapping it. Um, I was like pretty much broke, and I'm like, "There's no plan B. Like if this doesn't work, like I'm fucked." And I think that was a... That was the like lowest I'd ever been, and there's no way, like no matter all the ups and downs I went through post, you know, raising capital and being the hot thing, there's no low that's ever gonna be as low as the low that I felt at that point in time.
- HSHarry Stebbings
What did you tell yourself in that moment?
- SVSamir Vasavada
I- I don't know, I just believe in destiny, in some, like it's like sounds kinda cuckoo, but like I just believe like this was the thing when I was... Like I- there's just no way I would like not-... figure out how to be successful, not figure out... Like, this was the only, only path in life for me.
- HSHarry Stebbings
Can I ask, who were you trying to prove it to?
- SVSamir Vasavada
Ugh, I think I tried to prove it to myself at this point in time. Like, I, I, I think in the beginning, it was a lot, a lot of the motivator was, like, you know, my teachers at school were like, "What's this kid doing talking about all of this business stuff? He should be focused on school." My parents were like, "Why, why don't you... You know, the rest of the class is, is, you know, thinking about college applications and getting good grades and extracurricular activities, and you're just so fixated on this." There was a point in time where they had hired a therapist to talk me out of running the business and just be a normal kid. And I think for a long time, that had been... Like, and this was, like, years of my life, it had been, like, a motivating factor of, like, "I'm gonna prove all of these people wrong and I'm gonna be so successful." And I think, like, I did prove those people wrong, I felt like, for a while, um, you know, especially as we started to gain a lot of traction, and then I think it flipped. And I think it flipped, which is everyone's like, "These guys are a foregone conclusion. They're the next Collison brothers. They're the next, you know, next big thing. It's just gonna work. Faiz is gonna be a $10, $20 billion business." And we were like, "This feels weird." Like, for our whole lives, we were trying to prove everyone wrong, and now we're in, like... Now everyone, like, believes in us, and it's like, "Am I proving them right?" And, like, there was something that felt wrong about that. There was something that felt, like, deeply wrong about that. And then when it, like, flipped again, then, like, uh, we just kind of felt like we were back at home. We felt like we were... We, we, we, we, we had our, had our motivating factor.
- HSHarry Stebbings
Do you have a relationship with your parents today?
- SVSamir Vasavada
Yeah. My parents and I are super close. Um, I think the-
- HSHarry Stebbings
Do you not hold it against them that they didn't believe in you?
- SVSamir Vasavada
No, because I think they eventually believed in me.
- HSHarry Stebbings
When the signals were there.
- SVSamir Vasavada
When the signals started to pop up, yeah. Mm-hmm.
- HSHarry Stebbings
But, like... And I, and I'm not by no means comparing. My parents have many flaws, but mine didn't give a shit about me leaving law school. I was a scholar at law school, you know. Perfect way to do a, you know, uh, very kind of corporate life. And I remember calling up my mother, and I was like, "You know what? I'm gonna leave, and I'm gonna do the podcast." She's like, "Great. Good."
- SVSamir Vasavada
I think if you're a parent, I think a couple things happen. I think what the other parents and the other parents' kids say about you, and, you know, that, that kind of breeds some... Like, they see the kid who got into Stanford, who won the debate, who's, you know, debate champion, who's... like, does... you know, a tennis star. Like, they see that kid, and they're like, "You know, like, why can't you be him?" Like, "Why can't you be that person?" And, like, they see... You know, they're at the parent cocktail parties and, you know, they-
- HSHarry Stebbings
I mean this in the nicest way, but do you, do you not think that is bad parenting? Like, one, you are projecting an image of what you should be on your child, which is complete bullshit. Two, it's just group think. Like-
- SVSamir Vasavada
But that's all par-... Like, at least in the US. I don't know what it's like in London, but, and in England, but-
- HSHarry Stebbings
Different. I-
- SVSamir Vasavada
But in, in the US, like, it's, there's so much of this, like, tiger parenting, this group think, this-
- HSHarry Stebbings
But the pressure on you is...
- SVSamir Vasavada
Yeah, there's pressure on all these kids. It's why all these kids are super anxious and depressed, and they have a bunch of... They have expectations they don't know if they can live up to. There's... It's just the United States at this point in time, and I just never... Like, I, I just always assumed I was playing a different game than everyone else was, and I'm gonna win at my game, and they can all play their game and do, do fine on it. And I just always saw the bigger picture. I'm like, "This isn't... None of this fits into my world. It's none- none of this fits into my picture." And I think I... The reason why it didn't, like, cause a lot of damage long term with my relationship with my parents or my family in general is because, like, I think I had the introspection to believe, like, if I was them, right, if I'm a parent, I'm... You know, uh, you know, in the 2010s US, and given the information I know at the time, like, what would I... Like, I don't know anything about this, you know, startups in Silicon Valley and kids going out and starting a company. Like, this just, like, is kind of unprecedented. Like, how am I gonna react as a parent? Um, so I think, like, I just had some empathy for them looking back that at the time I, I didn't have, that, like, they did the best they could.
- HSHarry Stebbings
Do you think you hold vengeance or revenge, or do you think you kind of forget it?
- SVSamir Vasavada
I remember people that, like, gave up on me, and I remember, like... I, I think it's, it's not necessarily the people that gave me nos. 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. I think it's the people that were like, "This kid just doesn't get it. He's not listening to me," or, you know, "I think this about him. You know, I'm just... I'm gonna move on to the, the next thing." Whether that's an investor, whether that's, you know, an executive, whether it's, you know, it's another founder or a peer, right? I think I deeply remember those people that, like, I was friends with at one point in time that I thought believed in me, that I thought... that told me they were along for the journey. They told me that I could call them at any night and at, at any h- any hour of any day of, of the year, and they're gonna be there for me. And those people in the time of need were not there for me.
- HSHarry Stebbings
What piece of advice were you given that you disregarded that you should have taken?
- SVSamir Vasavada
I don't regret a lot. Like, I think I just kind of had to learn. There was a great piece of advice Ravi gave me that I should have internalized. I think there's a difference in terms of advice that... Like, I think, I think there's a world of difference in terms of what you know versus what you've internalized.
- HSHarry Stebbings
Mm-hmm.
- SVSamir Vasavada
So, I think a lot of people can parrot things of like, "You should do this particular thing." And it sounds like, like, "You should have integrity," right? And, like, yeah, it's, like, something you should have. You should have integ- integrity, but, like, oftentimes people know that, but they don't, they don't have integrity, right? So, I think y- you know, there's a difference in terms of what people know and what they do. And I think, you know, one, one piece of advice that I was given is you can't necessarily learn other people's lessons for them. I would spend so much time on trying to, you know, get someone or, you know, some-... you know, whether it's a team member, whether it's a, you know, someone to, to do something, to learn something, and they just... They wouldn't learn it. Then they would go and they would make that set of mistakes on their own, and-... they would, they would learn their lesson. And I think a lot of that applied to me as well, which is, like, you can't... I can't just listen to successful founders and all of their advice, just ad- blindly adopt it. Like, I have to kind of learn for myself to some extent. And I think so much of my ethos early on was, "I'm going to go to the smartest people on Earth, the most powerful, connected, successful people on Earth, and I'm gonna ask them what they did. And I'm gonna just do that because, like, it clearly worked for them, it's gonna work for me." And, like, it just didn't work for me. Their businesses were different than my business. Their... The market was different at that time than it was for m- me. And, like, I didn't learn the lessons for myself when in reality, over time, I... Just the only way to learn was if I learned it
- 55:40 – 1:01:41
Quick-Fire Round
- SVSamir Vasavada
myself.
- HSHarry Stebbings
I do want to move to a quick fire. So, I say a short statement, you give me your immediate thoughts.
- SVSamir Vasavada
Yeah.
- HSHarry Stebbings
That sound okay? So, who do you not have on your board who you would love to have on your board?
- SVSamir Vasavada
I would have loved to have someone with deep domain expertise early on, when we raised our series A round, in our space, who had built a company, you know, similar, similar in, in, in, in, in shape to ours. So... And I think having a perspective like that in the room would have been really valuable.
- HSHarry Stebbings
What do you know now that you wish you had known when you started Vise, above everything else?
- SVSamir Vasavada
Don't overly rely (laughs) on, um, on others' advice. Like, figure it out for yourself, and don't quit until the job is done.
- HSHarry Stebbings
What are you most insecure about today?
- SVSamir Vasavada
I don't know. That it, that it doesn't work. Like, I feel like I've put all of my eggs in this basket, and, like, I, I think there's some sp-
- HSHarry Stebbings
Do you feel a bit trapped?
- SVSamir Vasavada
Yeah. I think trapped is... Maybe not trapped because it's... I, I love what I do. But, like, I don't necessarily... I think there's some worry, there's some concern that, that, uh, you know, it doesn't work.
- HSHarry Stebbings
You know if it doesn't work, it will be okay.
- SVSamir Vasavada
Well, I do. I know it. I think I rationally know it. But I think, you know, when you work on something for, oh, it's been like seven, eight years now, like, since you were 15, 16, like, it becomes your baby. It becomes your identity, it becomes a part of you. And I think that, uh, one, kinda, lesson I'll give to founders is separate yourself and your identity, your personal identity from that of your company. And I think that's important to do, and I think it's hard to do.
- HSHarry Stebbings
Have you done it? I have not done it.
- SVSamir Vasavada
I haven't, but I would really like to.
- HSHarry Stebbings
(laughs)
- SVSamir Vasavada
Like, I am Vise. Vise is me. Like, I'm f- I'm in it, um, and I think that... I think maybe that's a little unhealthy.
- HSHarry Stebbings
It's unhealthy, but I think it's a necessity.
- SVSamir Vasavada
Yeah.
- HSHarry Stebbings
It's like obsession is a necessity, and it's very difficult to be obsessed and detached at the same time.
- SVSamir Vasavada
Yeah.
- HSHarry Stebbings
Um, so I completely get you. What leadership skill do you not have that you would most like to get?
- SVSamir Vasavada
It's something I r- I, I started to learn as we had a, you know, a bigger team and, you know, I had to manage people and managers, but, like, you know, this f- uh, feeling of, like, deep empathy and, you know, uh, you know, the ability to, to, uh, to elevate, to, to, to elevate everyone around me, um, more than just on the vision of the business. Again, it comes with, with time, it comes with experience. But I think so much of my time, I'm just so focused on, you know, the business, on figuring out the dri- the... Solving the problems of the business, and I'm not thinking about elevating everyone around me. And I think that, uh... I think there's some value in doing that. Like, I, I think it's important not to, uh, to overcorrect. I think it's not... It's important not to get too close to Elon. I think, I think there's some... there is some balance where you are... you're really helping support and, and boost those around you in a meaningful way.
- HSHarry Stebbings
Do you think you always did investor communications well?
- SVSamir Vasavada
Investor communications? Yes.
- HSHarry Stebbings
Yeah. Let- letting investors know about the status of the business, the progress of the business?
- SVSamir Vasavada
I think it was too optimistic-
- HSHarry Stebbings
Mm.
- SVSamir Vasavada
... um, 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 naïve, and as, as a result of being naïve, I was very optimistic. And I also knew that in every interaction, that investor was re-underwriting me.
- HSHarry Stebbings
Yeah.
Episode duration: 1:01:41
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