Sheel Mohnot: Lessons from Investing in Flexport and Missing on Robinhood | 20VC #917

1. 0:00 – 0:40

   Intro

   1. HSHarry Stebbings0:00

      (beeping) Three, two, one, zero. You have now arrived at your destination. Sheel, I am excited for this. I have heard so many good things, from, uh, snacking options that you love, to jumping over pools. This is gonna be a unique interview, so thank you so much for joining me today. (laughs)

   2. SMSheel Mohnot0:21

      Thank you for having me. And yeah, I've been, I've been a listener for so many years. Uh, super excited to be on the show.

   3. HSHarry Stebbings0:27

      That is a very kind way of saying of my aging, but, uh, I would love to start today-

   4. SMSheel Mohnot0:32

      (laughs)

   5. HSHarry Stebbings0:33

      ... with, uh, a little bit-

   6. SMSheel Mohnot0:33

      Well, you still can when you're 18, so. (laughs)

   7. HSHarry Stebbings0:35

      This is true, I'm actually-

   8. SMSheel Mohnot0:36

      But, um-

   9. HSHarry Stebbings0:36

      ... Benjamin Muffin in disguise. Um, but, uh-

   10. SMSheel Mohnot0:38

       (laughs) Exactly.

   11. HSHarry Stebbings0:38

       ... I wanna start with a little bit of

2. 0:40 – 3:09

   How did you get into the world of venture?

   1. HSHarry Stebbings0:40

      your context. How did you make your way into the world of venture, and then how did you come to found Better Tomorrow most recently?

   2. SMSheel Mohnot0:46

      Yeah. So, I made my way into venture, uh, I think probably a not unusual path. I was a founder. I, um, first joined on with a friend to start a company, uh, now in 2010, and then that company got acquired in 2012. Ended up starting a company, uh, shortly afterwards. That company got acquired in 2015. And at that point, 500 Startups, who had invested in the first company, asked me, uh, to join them. And originally, I was just joining them as a mentor, and then I found that I loved it. I think, you know, I loved helping founders at the earlier stages, and thought, "Hey, maybe I could make my career doing this." And that's sort of evolved into what it is today. So at 500 Startups, I started a fund, 500 Fintech, and then, um, over the course of a couple of years, I started interviewing at other funds, uh, and I was interviewing alongside this guy Jake Gibson, who was a friend of mine. He had started NerdWallet. I knew him well. He became an EIR of mine at 500 Fintech, and we're both interviewing at other funds. Things are going well, but we're talking to each other on the phone all the time, like, "How did your interview go? What did they ask you? What was difficult? What's the next step?" And so we kinda just became, like, really close during this time. And it's, to some people, it could've been a rivalry, like we were probably competing for the same jobs. Like, there's only gonna be one GP that specializes in fintech at a tier one fund. But we took it as a friendly thing, more than anything else. And any time a fund was interviewing one of us, we'd say, "Oh, hey, have you considered Jake? Have you considered Sheel?" And so we ended up getting offers at- at funds, but decided, during this time that he and I got to know each other a lot better, we decided, "Hey, maybe we should just do our own thing. These funds are maybe not for us. Some of them are too bureaucratic, some of them have different personalities than we like. Let's just do our own thing." So that was, uh, towards the end of 2019, and we haven't looked back. It's been amazing.

   3. HSHarry Stebbings2:54

      I mean, you're singing from my hymn sheet, baby. I'm completely unemployable, so I- I don't think I would've been offered the job.

   4. SMSheel Mohnot2:59

      (laughs)

   5. HSHarry Stebbings2:59

      Uh, but-

   6. SMSheel Mohnot3:00

      I think-

   7. HSHarry Stebbings3:01

      ... I ag- I agree with you on starting your own. The thing I wanna ask is a couple of things, and I go off schedule, but, you know, uh, after years of doing it, as you kindly reminded me, I- I can do what

3. 3:09 – 5:25

   When did you start angel investing?

   1. HSHarry Stebbings3:09

      I want. Um, so I'm starting on the acquisition side. I always wonder with, like, the first bit of money that you get, how much of an unlock is it? Like, when you sold both companies, were you in a position where, for the first time, you were financially independent? And, like, how much of an unlock is that moment actually?

   2. SMSheel Mohnot3:27

      Yeah, so for me, so yes, absolutely. I had, did not have, did not come from money or anything like that, didn't have much money before. Um, so it was a big unlock, and the first thing I did was started investing (laughs) in other companies. Uh, literally, the f- like, literally, like, within a month of, uh, getting the paycheck, I started angel investing. And I think it's- it's a passion of mine, and you know, when I m- I was moving to San Francisco, um, from Chicago, and I thought it would allow me to do a few things. One, um, get to know people. Like, I could (laughs) angel invest and- and meet interesting people through that, maybe be inspired to start my own thing, or maybe be inspired to join one of these companies, was- was my initial thought. Um, in terms of an unlock, I'm a pretty low burn lifestyle guy. Um, one of the things in my past that I think put me on this track is I, um, I lived in India, I did this fellowship, lived in India on a dollar a day. Uh, so very, (laughs) very low burn lifestyle. Um, I- I was working in microfinance, and decided I would live like my borrowers. And my borrowers, you know, lived on a dollar a day, so I decided I would too. And I realized that there are very few monetary things that make me happy. Like, I just don't need any material things to be happy. And so I... it's been- it's been great for me ever since. I think, like, a lot of people get into a trap where they constantly have, desire more mo- material things, and I just, like, am the luckiest guy that I don't have that.

   3. HSHarry Stebbings5:14

      Mate, have you ever been to Loro Piana? (laughs)

   4. SMSheel Mohnot5:18

      (laughs) Yeah. I mean, uh, it- it's beautiful stuff, it's just not, I just, like, I don't care.

   5. HSHarry Stebbings5:22

      It ain't a dollar a day, baby. Uh, I do wanna ask, though-

4. 5:25 – 8:08

   What parts of your history are you running from and towards?

   1. SMSheel Mohnot5:25

      For sure.

   2. HSHarry Stebbings5:25

      Um, Jeremy Lioueche from, uh, Lightspeed asked me this question once, and it was such a good one. It was like, we're all a function of our histories. And with that in mind, what parts of your history are you rebelling from, first, and what parts of your history are you running towards?

   3. SMSheel Mohnot5:44

      Ooh, good question. Okay, so rebelling from, I come from a very conservative Indian family. For those Indians, you- you'll- you'll appreciate, it's a Marwari Jain family. And, um, you know, my mom...Oh, actually, here, here's something I just learned. So I'm 40 years old. My grandmother's, uh, in from, from India, and she... I was talking to her about her age, and I, I realized, when she was 40 years old, I was already born.

   4. HSHarry Stebbings6:14

      (laughs)

   5. SMSheel Mohnot6:15

      She had a grandkid at the (laughs) age that I am. So very conservative family, people get married very early. There's only a few professions that they want you to be in. Uh, you know, my mom probably today, to this day, like, I'm a venture capitalist. She wishes I was a doctor, so much so that... Actually, funny story. Until five years ago, five years ago, I think my mom told me, "Hey, you know, you, you do so well on tests, you could probably still take the MCAT." The MCAT is the Medical College Admission Test.

   6. HSHarry Stebbings6:47

      (laughs)

   7. SMSheel Mohnot6:47

      "Like, why not, why not just find out how well you do?" Like, she still would prefer today that I, like, go back to medical school (laughs) and become a doctor because that's the great profession to be in. Um, so-

   8. HSHarry Stebbings7:00

      And so you're running from that?

   9. SMSheel Mohnot7:01

      ... so very conservative family. Am I running from that? I, uh, to a certain extent, maybe. Um, now, on the other hand, like, the, the other side of the question is, like, what part of your family are you, uh, or, or, or what type, type of, part of your history are you running towards?

   10. HSHarry Stebbings7:18

       Mm-hmm.

   11. SMSheel Mohnot7:19

       And there is this, like, there is this business side to my history as well. So, um, you know, probably because they couldn't do anything else, everyone ended up in business. Um, and it, it w- in very small forms, so, like, you know, they might have run a small store in a village in India. And then ultimately, like, my grandfather, uh, on my mom's side, grew from that into many businesses throughout time. So he, he had a business that was, that made pay phones, he had a business that made TVs, and he got into a bunch of, like, small scale manufacturing that I think is fascinating. And I think that part of, part of him, which is like trying different businesses out, is very much a part of me.

5. 8:08 – 9:50

   What did you learn from working at 500?

   1. SMSheel Mohnot8:08

   2. HSHarry Stebbings8:08

      Can I ask, what did you learn from 500? 500 is a unique experience to go through. You invested in a lot of companies at 500. And it was also your first, like, fund experience. What-

   3. SMSheel Mohnot8:18

      Very much, yeah.

   4. HSHarry Stebbings8:19

      ... d- what did you learn?

   5. SMSheel Mohnot8:22

      So, I mean, number one, it gave me a start and a fund that I could invest out of. I'd done a bunch of angel investing, but I didn't really know what running the fund entailed, because it, as, as you know, it's very different. There's a lot of other things. So 500, I wasn't just investing out of the fund. I started my own fund, distinct LPs, th- you know, fundraising, all that stuff. Um, although I should say (laughs) , um, it was really hard. You know, I had no track record. There's no reason that anyone should give me money, to be honest, um, at that time. And so for the first 18 months, I was basically funding it out of my own pocket, pretending like I had a fund.

   6. HSHarry Stebbings9:03

      (laughs)

   7. SMSheel Mohnot9:03

      And it was most of the money I had at the time. Like, I, I was selling stock to (laughs) invest in startups to pretend like I had a fund. Um, and fortunately, things worked out. But I'd say, like, the things I learned most, you know, you invest in a lot of companies, you learn it takes a long time. You can read about the power law, but actually seeing it, for me, was a big game changer. And you realize actually, like, even though I invested in 70 plus companies, there's only a handful of them that really matter. And the one, the one biggest one represents a 5X on the fund. And I think, like, I'd heard about these things, but you don't internalize it for a long time.

   8. HSHarry Stebbings9:47

      Can I ask what spec-

   9. SMSheel Mohnot9:48

      Um-

   10. HSHarry Stebbings9:48

       ... what specific moment did you realize the

6. 9:50 – 11:08

   The power of the power law

   1. HSHarry Stebbings9:50

      power of the power law? Which company and what moment?

   2. SMSheel Mohnot9:53

      (laughs) . So, uh, it's been, it's actually more recent. I'd say, like, in the past year, I really realized it. Um, I have, there's a, there are three or four, there are three companies that each represent multiple turns on the fund. Um, and I realized, oh, wow, if I just... I had the opportunity to sell secondary earlier this year, or actually late last year, and I realized, wow, I could sell just a small portion of this and return multiples to my LPs. That's a good idea. Um, and I think it really informed how I think about investing, which is, like, these smaller exits are not necessarily gonna get you anything. Even, even like a three, 5X return, it doesn't, unfortunately, it just doesn't move the needle that much when, when you, when you have a 100X return out there. Um, and, and now, by the way, all of this is, like, 2021 crazy valuations. And there's a great chance that that doesn't hold anymore. And so I think you're constantly learning in this environment.

7. 11:08 – 12:05

   Did you take chips off the table?

   1. SMSheel Mohnot11:08

   2. HSHarry Stebbings11:08

      Man, did you take any chips off the table? My biggest regret and my biggest lesson is that I didn't-

   3. SMSheel Mohnot11:13

      (laughs) .

   4. HSHarry Stebbings11:13

      ... because I believed in Sequoia's, "Hold onto your winners, never sell your winners," and I didn't. And I probably could have taken off about $25 million for an $8 million dollar fund.

   5. SMSheel Mohnot11:24

      So I have, unfortunately, the same lesson learned. (laughs)

   6. HSHarry Stebbings11:29

      (laughs) Fuck. Fuck! So annoying.

   7. SMSheel Mohnot11:33

      So I di- I did take off some, um, but not as much as I should have. And it's a lesson I will keep forever. I mean, I, there's, I, I should have, I should have sold more when I had the chance, a- and it was-

   8. HSHarry Stebbings11:51

      This is quite silly, not true.... as long as you take, and my, my lesson is, as long as you take, you know, real learnings from it, it's okay. Um, I mean, it's painful but it's okay. We live and we learn. The question then that I have is like, and it's kind of in the schedule

8. 12:05 – 15:15

   How do you think about diversification?

   1. HSHarry Stebbings12:05

      but I'm just kind of floating around here, if we agree the power law being as powerful as it is, it would make sense to just spray everywhere given how big the winners can be. If you're in Stripe, if you're in you name it, how big they can be, you should just spray. How do you think about the right levels of dri- diversification today with better tomorrow, given the awareness of just being in the winners?

   2. SMSheel Mohnot12:30

      Yeah. So, I think, I, I think like maybe that makes sense, the index approach, and there are funds that do that. Um, out here, Summer Capital, Liquid Too, I think are taking the index approach of writing, I think 100 to 500K checks and they're, uh, in a lot of companies that they see. I think that can work. I think it worked a lot better, um, you know, they, those guys started a decade ago and I think at that time, it made a lot of sense when valuations were still reasonable. They caught the big upswing up until '21, 2021. Now things are probably falling down again, uh, in terms of ultimate valuations. Um, I think the reason it doesn't work for us, we couldn't put money into every company, is we are hands-on investors and we invest in category FinTech. So, we couldn't have invested in Stripe and Braintree and all the other ones out there. Um, we have to choose one because that company is gonna get our time and energy and we're not gonna invest in a competitor. So, for us, um, we still have a relatively less concentrated portfolio than others. We have about 30 companies per fund. And the math is roughly we do 10 investments a year, three-year fund, fund life. And, um, and I think it works really well for us. Um, and, and in Fund One, we had, uh, 50% reserves. In Fund Two, we have actually 60% reserves. So, we're, we're reserving more for follow-ons. And, um, the reason we're doing that, people have asked like, "Why did you make the shift?" Maybe I took the st- thunder from you. Maybe you were gonna ask. (laughs)

   3. HSHarry Stebbings14:07

      No, go for it.

   4. SMSheel Mohnot14:07

      Um, but-

   5. HSHarry Stebbings14:08

      I'll just shut up the whole time. (laughs)

   6. SMSheel Mohnot14:11

      (laughs) Yeah, you just keep talking and there's-

   7. HSHarry Stebbings14:12

      Monologue.

   8. SMSheel Mohnot14:12

      ... no interview whatsoever. Yeah, monologue. Um, so, so what happened was like when we started Fund One, you know, uh, which was only a few, uh, two and a half years ago, Jake and I again had been writing smaller checks. We hadn't been lead investors before. So we asked people like, "When you're leading investments, like what happens?" And people said, "Oh, like get your ownership up front. You're not gonna be able to follow on into companies." And I think our model is a little bit different. We're pretty hands-on. In almost every case, we introduced the founder to their series A and series B investor. So, I think because of that, we haven't gotten, gotten cut out of our parada yet. Um, one ti- you know, one time we had to like take a little bit less than we wanted. But for the most part, we've been getting our parada. And, um, so because of that, like we actually need more follow-on and, and our companies have had a pretty high follow-on rate and we want the ability to, to follow-on into our winners and also be able to support companies

9. 15:15 – 16:31

   How do you think about ownership levels on first check?

   1. SMSheel Mohnot15:15

      that need them-

   2. HSHarry Stebbings15:15

      Okay.

   3. SMSheel Mohnot15:16

      ... that need the money.

   4. HSHarry Stebbings15:16

      So we have a 40% initial check. On the new fund sizes, that's $60 million. 30 companies we're doing $2 million initial check. In a four million round say, three to four million round, we're gonna get like seven to 10% ownership. How do you think about the impo-

   5. SMSheel Mohnot15:34

      Mm.

   6. HSHarry Stebbings15:35

      How do you think about the importance of ownership on that first check and where's the bar for you?

   7. SMSheel Mohnot15:38

      Yeah. Yeah, yeah, yeah. So, um, so our minimum is actually 10. So, we have invested, um... So in Fund One, our rough numbers, our average first check was a million bucks and for about 10% ownership. So we invested on average at a 10 million post in Fund One. Um, despite the mark, and that was 2020, 2021, despite the overall market, you know, theoretically being down, seed valuations in FinTech for some reason haven't really fallen much. And so, our 2022 numbers are actually higher. We're investing at a, at a higher valuation than we were then. So maybe, maybe in this fund we average closer to 15 million post. But, um, we are shooting for 10 to 15% ownership. Right now we're probably, in Fund Two, we're probably averaging

10. 16:31 – 18:37

    Where are you finding your deals?

    1. SMSheel Mohnot16:31

       12, 13%.

    2. HSHarry Stebbings16:32

       I'm gonna sound like a total knob, but I'm gonna go for it anyway. Where are you finding these deals? And are these like then C class deals? Because like I never see-

    3. SMSheel Mohnot16:42

       Yeah, great question.

    4. HSHarry Stebbings16:43

       ... under a $10 million... I mean, if it's a great team out of a great company, you're four on 20 day one.

    5. SMSheel Mohnot16:51

       Okay. Let me, let me just tell you from Fund One, I'll just tell you our top four companies.

    6. HSHarry Stebbings16:58

       Sure.

    7. SMSheel Mohnot16:59

       Their entry point, where we invested, and what they're worth today.

    8. HSHarry Stebbings17:02

       Right.

    9. SMSheel Mohnot17:03

       Number one, uh, we led a deal at 12 and a half million. It's now worth 1.2 billion. Uh, number two, our first check was at... It was either eight or 10 million and it's now 600 million. Uh, number three, first investment was at two million, it's now 600 million. And number four, first investment was at eight and a half million, it's now at 300 million. Um-

    10. HSHarry Stebbings17:29

        Okay. Pre- pretty, pretty good. So my question to you is like, what did you see? Like how were they that priced, bluntly? Because-

    11. SMSheel Mohnot17:38

        So there's a few things to note. One is if you fish in like the, the same pond as everyone else, then like those are the deal, you know, then things may end up getting priced up. The other is there's a difference between a price taker and a price maker. So like oftentimes a founder will say like, "This is what I want."... and we say, "Okay. Like, totally understandable. If you wanna work with us, the price is X. And here's a bunch of folks we can connect you to who have chosen, chosen that, and those are our founders. And they can tell you why they chose to work with us, even though it wasn't the deal they initially wanted. And they can tell you that they would do it again and again, and they refer their friends to us."

    12. HSHarry Stebbings18:26

        Fuck. That's a good entry point, my friend (laughs) . Jesus. Uh, talk, talk to me about, um... That makes me feel terrible at my level as ownership.

    13. SMSheel Mohnot18:34

        (laughs) .

    14. HSHarry Stebbings18:35

        Um, fuck. Um,

11. 18:37 – 20:13

    Reserve allocation for future unknowns

    1. HSHarry Stebbings18:37

       uh, tell me, reserves. You mentioned the pro ratas there. I, I think we're about to see, like, a, a tide change in reserves. Before, in, like, great years, man, if we did reserves or not, no one cared. Like, the big funds would just gobble it up. I think that's gonna change-

    2. SMSheel Mohnot18:51

       Totally.

    3. HSHarry Stebbings18:52

       Uh, how do you think about, first on the reserve allocation side, proactively planning ahead of time for unknowns that are future unknowns? How do you think about that challenge?

    4. SMSheel Mohnot19:05

       Yeah, so there's so, there's so many unknowns. We, uh, a lot of people think about it on a per company basis. We really think about it on a fund basis and kind of, like, we're constantly looking at the spreadsheet of how much money we have, how much money we've deployed, how much into first checks, follow-ons, and subsequent rounds. So, I, I, I think, like, there's no secret math that we're constant- we're doing. It's sort of, like, we're looking at it all the time. There's no, like, there's no absolute math that we need to do.

    5. HSHarry Stebbings19:32

       Is it-

    6. SMSheel Mohnot19:32

       We have, we haven't thought about anything in that detail.

    7. HSHarry Stebbings19:33

       For you, is it not simple, though? I, if I (laughs) , if I was you (laughs) , which I'm not, uh, but we'll play this one anyway. So you want 150 million for the early. You do-

    8. SMSheel Mohnot19:44

       Yeah.

    9. HSHarry Stebbings19:44

       Um, s- I don't know. Fuck it. 52, um, million checks, and then you got a load of other costs and stuff baked in, but 52 million checks.

    10. SMSheel Mohnot19:52

        Yeah, yeah, yeah.

    11. HSHarry Stebbings19:53

        And then you've got the 75 million in the opportunity fund. Double down on-

    12. SMSheel Mohnot19:57

        Yeah.

    13. HSHarry Stebbings19:58

        ... everything there. So initial checks is from the early, and then reserves is for the absolute all-stars. And then bluntly, I-

    14. SMSheel Mohnot20:04

        Exactly.

    15. HSHarry Stebbings20:05

        I believe that the pro rata for your middle tier is never actually a great thing anyway. Like, the messy middle pro rata? You're not

12. 20:13 – 21:20

    Pro rata

    1. HSHarry Stebbings20:13

       gonna regret not doing it. How, how do you feel about that actually? And also, a lot of funds, they say, "Oh, we always do our pro rata." I'm like, "Well, that's moronic."

    2. SMSheel Mohnot20:24

       Yeah, we definitely don't always do our pro rata. I would say we, um, we are choosy, but also, like, you wanna, there, there's a lot of companies which you wanna turn over another card. Like, they've done a good job. They're a great team. They haven't quite cracked it yet. Let's turn over another card. And they need a little bit more money. And we've been there on that side of things, and, and been there to turn over that card.

    3. HSHarry Stebbings20:50

       Can I ask you a tough question? I'm still learning this business. Um, uh, what do you-

    4. SMSheel Mohnot20:54

       As are, as am I (laughs) .

    5. HSHarry Stebbings20:56

       What, what do you do when you don't want to turn over another card and you have just lost face?

    6. SMSheel Mohnot21:01

       Yeah, and i- it happens a lot. Um, I'd say we're always supportive of the companies, and, and they'll probably get a disproportionate amount of our, of our time, the ones that are in trouble that we don't want to support with our money. Um, but, you know, w- w- we're not gonna, we're not gonna

13. 21:20 – 25:17

    Is venture collaborative today?

    1. SMSheel Mohnot21:20

       continue to support companies that we don't believe in.

    2. HSHarry Stebbings21:22

       I, I, I agree, and I think that's right. Um, in terms of, like, getting the ownerships that we spoke about there, uh, a little bit is about collaboration between different players in market. I specifically think that venture's never been quite so sharp-elbowed and has never been as uncollaborative. Do you agree with me? And how do you think about where we are in the sliding scale of collaboration between venture funds?

    3. SMSheel Mohnot21:49

       I don't agree with you, actually.

    4. HSHarry Stebbings21:50

       Well, you're w- you're wrong (laughs) .

    5. SMSheel Mohnot21:51

       I think if you-

    6. HSHarry Stebbings21:52

       (laughs) .

    7. SMSheel Mohnot21:52

       You're wrong (laughs) . Here, I'll, here, Harry, I'll, I'll tell you, tell you, uh, a simple, simple thing to prove it. To pr- prove it, yeah (laughs) . Um, is, uh, a lot of, let's say, a lot of the, like, multi-stage funds, typically, historically leading Series As, they used to have an ownership threshold of 20% minimum. And now, they have a lower ownership threshold, 15. And, um, in part, it's rounds can be less dilutive. In other part though, they make space for the earlier guys because the earlier guys, they need... Like, the folks I introduce deals to, they know they can't cut me out of my pro rata because they're not gonna see the next deal. And there are... So I, I think actually, I think we're less sharp el- elbow than we used to, used to be. There was a time when seed rounds were a bunch of angels coming together and cobbling together a 500K round. That is no longer with the emergence of seed, of seed funds. But in almost every company we've invested in, there are investors alongside us, and we love working with these guys, um, folks who write, you know, one to 500K checks, and then a bunch of other angels, and sometimes a co-lead. So, like, uh, we're very collaborative. Obviously, there are some funds who are lead only, no co-lead, that we can't work with, but we love working with other funds.

    8. HSHarry Stebbings23:19

       So I, uh, so I think, like, bluntly, the reduction in, um, ownership requirements is because the founders wanting less dilution and them having the power to do that, so I think that's why the rounds are 20% and not 25%. And then I think we've seen the rising importance and power of operator angels, getting a Claire Hughes Johnson, getting an Emily Choi from Coinbase can be fantastically needle moving for your business. And so they make more room there.

    9. SMSheel Mohnot23:43

       Totally.

    10. HSHarry Stebbings23:44

        And then you've actually got this emergent class of Josh Buckleys, Harry Stebbings, Lachy Grooms annoying people for funds-

    11. SMSheel Mohnot23:52

        (laughs) .

    12. HSHarry Stebbings23:52

        ... who actually have real money but are, uh, like, you know, we're not like Better Tomorrow Ventures, which is a real fund structure with teams and, like, n- new funds. We're different in that way. I think that's annoying for the funds, and it's much less collaborative.

    13. SMSheel Mohnot24:08

        So I, I guess, like, are you saying collaboration at later stages or at seed?

    14. HSHarry Stebbings24:11

        I'm saying seed and A.

    15. SMSheel Mohnot24:15

        Yeah, I think A, A is the toughest round to get multiple people into, because there's typically a lead investor, a sin- typically a single one. At, at s- although, actually like in our last few deals, even at A, there have been co-leads. Um, and, you know, and, and these are like great funds who chose, chose to take 8% ownership each or 9% ownership each. Um, so I thi- I think it's, it's happening.

    16. HSHarry Stebbings24:45

        Can I ask, can you...

    17. SMSheel Mohnot24:46

        And that never used to happen. You wouldn't have like a tier one fund taking 8% ownership in a series A, but that's happening.

    18. HSHarry Stebbings24:54

        I get you. I get you, totally. Um, and I think at least what fucks me off, like they should be taking 8%, because if you are one of the big multi-stage funds doing a seed, guys, like be more collaborative. Do your 8%. You can jump on the A and get another 10% there. Like, let people in, be more collaborative. Uh, really, I find it astonishing how sometimes short-sighted people are.

14. 25:17 – 26:13

    Have you grown ownership in companies?

    1. HSHarry Stebbings25:17

       I, I do wanna ask, in terms of like growing ownership, do you have the chance to actually grow ownership with Round? I was always taught that you will never be able to grow ownership.

    2. SMSheel Mohnot25:24

       Yeah.

    3. HSHarry Stebbings25:24

       You might protect it, but you can't grow it. Do you find you can?

    4. SMSheel Mohnot25:28

       No, in, we have, yeah. In, in some of our best companies, we've grown ownership over time, so yeah, the one that comes to mind, we started it at around 10, and now we have 13. Um, so over time, we've grown. Another one, um, we did our first investment that was like one at 10, and then we did another investment just like months later at like, uh, 18. And then, uh, and then in the series A that got done recently, um, we've maintained from that. But like we grew between our first check and second check.

    5. HSHarry Stebbings26:06

       Got you. Okay. No, I, I, I always have the question of like just how, how possible is it to grow ownership

15. 26:13 – 29:01

    Price on reinvestments

    1. HSHarry Stebbings26:13

       between rounds? So that's great to hear. Can I ask, one of my biggest mistakes, um, is when rounds get done, and they're good companies, this is not The Tweeners, but they are extraordinarily priced.

    2. SMSheel Mohnot26:24

       Yeah.

    3. HSHarry Stebbings26:24

       And you're going, "What? I, I, I love the company, but I, I don't wanna do my pro rata at that price." I'd love to hear, like when you hear that, how do you think about pricing for reinvestments?

    4. SMSheel Mohnot26:38

       Yeah.

    5. HSHarry Stebbings26:38

       And then are there any times where it stands out to you?

    6. SMSheel Mohnot26:42

       Yeah, so this is, this is a great one. I would say like our strategy is to be, as you know, very sensitive on entry price. And we will, you know, like I said, we, we will negotiate hard on entry price, very hard, and get the price we want and, and the founders we wanna work with. But after that, we are fully committed to the company, and we will do whatever the founder wants, uh, and we will help them raise the best round for them. It may not be the highest price, but if it is, if they choose the highest price, we're in. And if we believe in that founder, we will do our full pro rata. Now, what has happened is, particularly second half of last year, all of the series As in our portfolio, like we were doing 'em at the price that you know we invest at, and then they were getting done at the 100 to 125 range, which was just bonkers. Um, but we still participated in those rounds, because, you know, we said, "Hey, we believe in this founder. We've got our ownership. We've got pretty good ownership up front. We can support them in this, in this next round." And i- supporting them is introducing them to everyone, guiding them through the process, and supporting them financially as well.

    7. HSHarry Stebbings28:03

       Have there been anywhere you haven't done it and you should have done it and it really stands out to you?

    8. SMSheel Mohnot28:12

       There, uh...

    9. HSHarry Stebbings28:13

       Uh, Pomelo.

    10. SMSheel Mohnot28:14

        No-

    11. HSHarry Stebbings28:14

        Do you know Pomelo, the b- banking as a service provider in Latin America?

    12. SMSheel Mohnot28:18

        Know it well, yeah. Know it well. Um, look, that one's too early to say. I think like they've, any of these companies that have raised a bunch of money way ahead of the traction, it's too early to say. Pomelo, great company, outstanding founders, have an insane amount of money in runway right now. But you can't say, oh, like, "I should have invested every cent in it," because it's too early to know whether it's gonna work. And I think that's another learning from like being in venture now for s- six and a half, seven years, like the ones that seem like they're winning early may not be the ones that actually ultimately are winning.

    13. HSHarry Stebbings28:53

        Tot- tot- totally agree with you there. From, well, you mentioned kind of really seeing the power law take effect early. I do wanna get into

16. 29:01 – 32:15

    What were your biggest hits?

    1. HSHarry Stebbings29:01

       like the hits. I think people are wrong when they say you don't learn from success. I think that's bullshit. Um, when you look at like your biggest hit, what, what's your biggest hit been from a cashback perspective and then from a multiple perspective? And what have been some learnings from it?

    2. SMSheel Mohnot29:17

       Yeah. Okay, so personally, my biggest hit from a cashback perspective is Flexport. I think rough numbers when I invested, it was like 15 cents a share, and I sold at $25.40 a share. Um, and then from the fund, my biggest was, uh, a company, actually I'm not allowed to name, but, um, it actually, this is interesting. It was not what you would think of as a screaming success. The company exited for $230 million, so not a success these days by any venture standard. But I had invested at a two and a half million dollar valuation, and the company didn't take much dilution. So for me, it was an outstanding win, um, investing from two and a half to 230 million quickly, and I was able to, um, show DPI immediately in my fund. So it was a huge win for me.Um, so that, that was, that was a good one. And then unrealized, I think my biggest is, uh, a company called Chipper Cash. Um, my first investment in the company was at a two and a half million dollar valuation about three years ago. And the last round was at two, over two billion.

    3. HSHarry Stebbings30:41

       Okay. So when you look at these three, are there learnings that you take from them having had those and having been through that experience?

    4. SMSheel Mohnot30:52

       Yeah. I think, you know, the, the one, the company I didn't name, the learning was if you're a capital efficient business, like there doesn't have to be a lot of dilution, and that can be a way better outcome. So an example is, that company, $230 million outcome, it actually returned more money than another exit that I had invested the same amount of money at the same price and is now worth 900 million. That actually is worth less than the company that, that sold for 230. So that was a huge learning for me, is invest in capital efficient businesses. Businesses that constantly need venture capital dollars to acquire customers just aren't as good businesses. And you've seen it with the likes of Uber, you know, today $50 billion enterprise value, there's $25 billion of venture capital (laughs) money that went into that company. And I think if you contrast that with a bunch of the SaaS businesses that are very capital efficient, there's a way better outcome. And you see that headline number valuation is, like, kind of all people see, but actually, like, I learned from this experience, like, actually, it doesn't matter. Like, I had a great fund return on this, you know, what many people would call a shitty outcome, like a $230 million outcome.

    5. HSHarry Stebbings32:04

       That's, I totally agree. I always think of Veeva Systems with Peter Gassner, which is obviously now, like, you know, multi, multi-billion dollar company-

    6. SMSheel Mohnot32:09

       Totally.

    7. HSHarry Stebbings32:09

       ... with 30 million total raised? Insane. Um, okay. We also have,

17. 32:15 – 34:32

    What were your biggest misses?

    1. HSHarry Stebbings32:15

       um, misses. Um, (laughs) I, I have some misses. Um-

    2. SMSheel Mohnot32:19

       Oh, yeah.

    3. HSHarry Stebbings32:20

       (laughs)

    4. SMSheel Mohnot32:21

       Oh, a lot of them. (laughs)

    5. HSHarry Stebbings32:22

       So, so hit me. What are the, what are the biggest misses for you, one? And what did you learn from those?

    6. SMSheel Mohnot32:28

       Yeah. So I, I think in fintech, there's this, like, wave of companies that came up. The, the most valuable recently, Robinhood obviously has fallen in the public markets quite substantially, but I saw it very early on and I thought, you know, "What's the difference?" There had been other free trading apps before. And I also just, like, frankly, wasn't a huge believer in retail trading, that there would be a lot of retail trading out there. So obviously, I was just completely wrong. Um, but I think what I'd missed is, like, the free trading apps of the past were very different than Robinhood. Robinhood was mobile first, and it was actually bringing a new class of investors on in that these, like, Freetrade and Zecco and others had not done. So I think that was a huge miss. Um, I think Chime was a big miss. Um, I, you know, I, I never looked at it very closely, but I thought, like, at 500 we'd invested in a company called Simple, and Simple had exited. It was a nice exit, but it was in the hundreds of mi- hund- low hundred millions. And, um, we thought, like, they had grown a huge wait list and then people hadn't gotten off the wait list. So we thought, "Okay, it's just tough to make neobanking work in the US." And while Chime at 25 billion is probably very significantly overvalued, they still have had a lot of success, and still I should have tried to invest in that company. Um, and I think what I missed was, like, they did things differently. Um, they had a few different things. And what, uh, I think the biggest miss for me was you look at a model, you've invested in a model that didn't work, and you have the idea that it can't work. And actually, no, that's not true. It's just, like, the founder didn't do the right things to make it work could be what, what's happening.

    7. HSHarry Stebbings34:16

       So do you, so exactly, that was gonna be my question, 'cause I have the same challenge where, you know, you look at, I, I don't know, healthcare. And you'd invested there before, it sucks 'cause of selling to large providers, sales cycles, whatever the problems may be. Um, and then you say, "All healthcare sucks and actually

18. 34:32 – 35:15

    How do you maintain mental plasticity?

    1. HSHarry Stebbings34:32

       it's not gonna work." Super. How do you retain mental plasticity that actually, yeah, Simple had these issues, but actually Chime could be different. Or yeah, Freetrade might have not unlocked this new market segment. But Robin, how do you retain mental plasticity?

    2. SMSheel Mohnot34:47

       You know, it's hard. It's something I stril- still struggle with. But, um, there have been times when I invested in the same model, like once that didn't work, and then I felt like I found the right founder and then invested in that company.

    3. HSHarry Stebbings35:04

       I get you. I agree. Um, it's, it's such a tough one. I find, like-

    4. SMSheel Mohnot35:09

       It's really tough.

    5. HSHarry Stebbings35:10

       ... not being cynical actually can be relatively challenging. Um-

19. 35:15 – 38:07

    Advice to Fund 1 managers

    1. HSHarry Stebbings35:15

    2. SMSheel Mohnot35:15

       For sure.

    3. HSHarry Stebbings35:15

       ... I, I do want to ask you, when we, we heard about some of the great wins, um, when we think about, like, fund ones, you see, and I'm sure you get asked a lot of advice from fund one managers. What do you think are the biggest mistakes you see fund one managers make in the deployment of their fund ones?

    4. SMSheel Mohnot35:31

       I think number one is not being price disciplined. And I think, like, I've learned through my 500 fintech time h- the importance of price discipline. And I think there's a lot of folks out there, a lot of the funds started in the last couple of years. Um, folks have only seen an up market where, like, you know, pretty much anything you invested in the last few years, like, someone else would come along and invest at a higher price.

    5. HSHarry Stebbings35:59

       Sure.

    6. SMSheel Mohnot35:59

       And so you, and then you had the idea, and then, like, series As were getting done in the hundreds of, hundred million dollars. And that's not normal. That was an aberration by cheap money that came and that happened in the last two years, COVID induced. And that's not normal. So you can't invest in a seed company at a $50 million valuation and expect to make money. Like, that's, if you're doing that, it's just gonna be really tough. And so I see a lot of folks doing that today. And fortunately, I...... learned the lesson at 500 Fintech, and so I think I'm not doing as much of that. (laughs) Um, so I, I think that, that's one. Um, I think the other is thinking through portfolio construction reserve strategy, and, you know, how to invest more in your winners.

    7. HSHarry Stebbings36:53

       I, I, I agree totally, especially on the pricing discipline. When you look back at, you know, BTV Fund 1, what would you say your biggest mistakes or regret was in the deployment? You know, very candidly, on mine, I'd probably say, I don't think our ownership levels are high enough. I think we're in great deals, but I don't think our ownership levels are where they need to be.

    8. SMSheel Mohnot37:13

       I don't think our ownership levels (laughs) are where they need to be, either. So, like I, I think our biggest mistake is not, is not buying enough of the companies. Um, you know, we really put in a lot of time with founders, and founders consistently tell us that we're their first call, and some founders have said, like, "I wish you owned more of this company." Like, "I wish I didn't have those other folks at my cap table at seed. I wish I'd given you more." Um, and so, I wish we owned more. We averaged 10%, and in this fund, we're, we're hoping to average closer to 15.

    9. HSHarry Stebbings37:53

       Listen, I, I, I totally get you. Always wonderful to hear from portfolio companies, though. I, I, I do wanna ask one final thing, and then we're gonna move into, uh, something where I have a lot of thoughts, which is geography. Um, having spent time in Pakistan-

    10. SMSheel Mohnot38:05

        Oh, yes.

    11. HSHarry Stebbings38:05

        ... I, I have fucking

20. 38:07 – 40:01

    Overly large GP commits

    1. HSHarry Stebbings38:07

       thoughts on geography

    2. NANarrator38:07

       Go on.

    3. SMSheel Mohnot38:07

       Totally.

    4. HSHarry Stebbings38:08

       Final one is, like, overly large GP commits. Tell me, how do you feel about these overly large GP commits?

    5. SMSheel Mohnot38:16

       So, so I mentioned in 500 Fintech, I had to fake like I had a fund, because for the first 18 months, zero people would give me money. Zero. So, I invested in my own capital, which, you know, is not a huge corpus, but I did the first almost 30 investments from my own pocket. And that was a hu- that was a pretty big chunk of my net worth. So then, as I think about it now, if you, if a huge chunk of your net worth is in the fund, overly large GP commit, then you do things differently, like, "Oh, I wanna buy a house. Maybe I should take secondary in this company," even though that's not (laughs) what's right for, for the fund. Like, you could make those mistakes. And so, when people encourage overly large GP commits, I just think about that and, you know, you might make choices based on your life that you should not be doing, that aren't in the best interest of the fund.

    6. HSHarry Stebbings39:07

       What do you think-

    7. SMSheel Mohnot39:07

       And I think nobody's talking about that.

    8. HSHarry Stebbings39:08

       ... what do you think is overly large?

    9. SMSheel Mohnot39:11

       So, I think, I think it really should be some portion of your net worth.

    10. HSHarry Stebbings39:16

        Yeah.

    11. SMSheel Mohnot39:16

        And maybe it should be, like, up to 10% of your net worth should be in a fund. Um, and that's a significant portion, but not like, it's not like you're gonna need an extra, like, you're not gonna wanna pull out, like, 3% of your net worth for something.

    12. HSHarry Stebbings39:31

        All right.

    13. SMSheel Mohnot39:31

        So, I think 10% of your net worth is a good guide.

    14. HSHarry Stebbings39:33

        I also find it moronic that, because you insist on a certain bar, the managers can't do it out of their own personal capital, and so then they pay for it out of fees, and then that means that they are fundamentally capped from reinvesting in their own teams, platforms, businesses, and prevent-

    15. SMSheel Mohnot39:48

        Totally.

    16. HSHarry Stebbings39:48

        ... quality in the funds. And it's like, "Well, well done. You got 2%, but it's actually coming out of the fees anyway, and it just puts a-

    17. SMSheel Mohnot39:55

        (laughs)

    18. HSHarry Stebbings39:55

        ... barrier on what we can do."

    19. SMSheel Mohnot39:56

        It's true. It's true.

    20. HSHarry Stebbings39:59

        Anyway, that's one area where I

21. 40:01 – 45:35

    Are you worried about emerging markets?

    1. HSHarry Stebbings40:01

       have strong thoughts. Another area, geography. You guys, as you said, like, you fish in different ponds, and I love it. I've fished in different ponds, too. We've got Australia, we've got Pakistan, we've got Latin America. I'm worried. I am worried, Sheel. I think in the macro, we're gonna see complete retrenchment away from emerging markets that we mentioned, uh, Southeast Asia, Indonesia included. Um, are you worried, and how do you feel looking at emerging markets moving forward into this environment?

    2. SMSheel Mohnot40:30

       Yeah, so I, I'd agree with you on the broad overall sentiment. Totally agree. Um, you know, in the last couple of years, it was risk on, and you go out as far as you, you go r- out really far on the risk curve when there's a lot of capital. And so, you invest in these frontier markets. And then, as we've shifted, interest rates are lower, or sorry, higher, as interest rates are higher, you come closer to home. And, um, that's what we're seeing today. So, I agree with you, but I'll, I'll put some nuance on it. I think there are co- there are countries, ar- are markets now that have a homegrown ecosystem. India is one. There's so much capital in India by itself. Um, and they have great local funds. Um, there's Latin America, which now also has great local funds.

    3. HSHarry Stebbings41:22

       Mm-hmm.

    4. SMSheel Mohnot41:22

       And they, they can support you from beginning to end, from C through D. (coughs) Um, so Latin America and India have these funds, and India's deploying into Southeast Asia. I think the markets that are in the most trouble are Africa and Pakistan. A lot of capital went into them in the last few years, and there has, there have been successful companies, but actually, the most valued companies in both markets, so in Pakistan, Airlift, which you know well, um, recently, uh, I think announced shutting down, it's shutting down. I think it was the most valuable company in Pakistan. In, uh, in Africa, the most valuable company is Flutterwave. They've had a host of challenges in the, in the press recently. So, I think people look at those markets and say, last year, they were looking at those markets and saying, "I gotta be in this market." Today, they're looking at those markets and saying, "Oh, shit. I've never even been to Pakistan. I cannot write a large check into this market. I don't know what's going on." And I think... So, I think there's gonna be some challenges in those markets. I think there are other fantastic companies in these markets that are probably totally shielded from it. Um, you know, I mentioned Chipper Cash in our, is in our portfolio. They have, uh, they're doing super well. I think...... they're relatively shielded. I do think like that incremental dollar is way harder to raise, and there could be challenges ahead. And investing in the market is, and- and sort of running a business in the market is challenging. But I think there's some companies that'll do- do fine. And I think overall, it's just a lot more challenging market. I agree with you.

    5. HSHarry Stebbings43:00

       This is where I've developed as an interviewer. I used to just be like, "Yes." And now I'm like, "Uh, I don't know. I disagree." I disagree on LATAM. Okay? I don't know if we have the-

    6. SMSheel Mohnot43:09

       Yeah.

    7. HSHarry Stebbings43:09

       ... life cycle funding in LATAM that we think we do. You've got Kaszek, who are amazing and fantastic-

    8. SMSheel Mohnot43:14

       Yeah.

    9. HSHarry Stebbings43:14

       ... but they will tap out at a certain level. They- they need help. I mean, they can't finance-

    10. SMSheel Mohnot43:18

        For sure.

    11. HSHarry Stebbings43:19

        ... the whole ecosystem. And then you've got great local funds, um, Monashees, Canary, um, you know.

    12. SMSheel Mohnot43:25

        Yeah, yeah, yeah.

    13. HSHarry Stebbings43:25

        But they're not doing growth capital. And then you've got, you know, General Atlantic, sure, but I mean, that's split between, you know, doing, you know, a billion in Shine and 100 billion in Asia and, you know, doing everything that General Atlantic does. Naspers, sure, but again, it's pretty split. I- I don't see someone actually carrying the big baton, uh, with weight.

    14. SMSheel Mohnot43:50

        I- I think, I think you're- you're right on LATAM, uh, more of ex- more of an extent, especially, you know, SoftBank pulling out of the market is a big hole.

    15. HSHarry Stebbings43:59

        Yeah.

    16. SMSheel Mohnot43:59

        Um, I do think overall though, there's still appetite from US investors to invest down there. Uh, you know, NewBank was obviously a tremendous success, even in this market, and it's doing fine in- as a public company. Um, I think because there has been success, there will be more capital. But I agree with you, it's- there's gonna be less capital than there was before.

    17. HSHarry Stebbings44:21

        So how do you advise your companies in emerging markets?

    18. SMSheel Mohnot44:27

        So I think more- more than ever, and I- I hate to say this, but it's about getting into free cash flow positive as soon as possible. And what's annoying is for the last couple of years, that was not the guidance.

    19. HSHarry Stebbings44:41

        Yeah.

    20. SMSheel Mohnot44:42

        And so people built these companies in a way that was somewhat unsustainable, and you have to make a shift on a dime. And we actually have companies that have been able to do it. And like we have a company that went from burning $7 million a month at the beginning of this year to probably being free cash flow positive in the next couple months.

    21. HSHarry Stebbings45:02

        I think the thing that people also don't anticipate, which is so true, is, um, how much a mindset of aggression and steroid growth is built into a team. And when you suddenly say, "Free cash flow positive tomorrow, please," it takes a very significant lag in time for the team to embrace the mindset shift of all risk on versus risk off. Do you see what I mean?

    22. SMSheel Mohnot45:28

        100%.

    23. HSHarry Stebbings45:28

        Yeah. I didn't-

    24. SMSheel Mohnot45:29

        100% agree.

    25. HSHarry Stebbings45:29

        I didn't anticipate that.

    26. SMSheel Mohnot45:31

        But some founders just are so fucking good at it. Like some founders

22. 45:35 – 46:52

    Most memorable first founder meeting

    1. SMSheel Mohnot45:35

       just are able to do it, make the changes they need to make very quickly.

    2. HSHarry Stebbings45:38

       What's the most memorable first founder meeting you've ever had? Like mine was like Johnny at Hopin, was, uh, oh my god, so compelling and magnetic.

    3. SMSheel Mohnot45:48

       Yeah, I think the most, um, the most compelling first pitch I had was Ryan Peterson at Flexport. Um, he just like knows the industry so well, could... I, what- what I l- actually, my- my favorite founders are all, all love learning, and they love learning something and then teaching me about it. So he taught me a lot about the freight industry. Um, another founder that comes to mind is Itai at Unit. He l- just loves learning about the banking industry and then just like sharing tidbits that I find so fascinating. And like I could see as he was learning, he was teaching me at the same time, and I think that's a great trait for a founder.

    4. HSHarry Stebbings46:30

       I really like that. No, uh, I totally agree with you. Um, I- I- I thought he was fantastic actually when I met him. I just, uh, didn't love the price so much. (laughs)

    5. SMSheel Mohnot46:39

       Oh yeah, totally.

    6. HSHarry Stebbings46:40

       Um-

    7. SMSheel Mohnot46:40

       I get it. Whew.

    8. HSHarry Stebbings46:41

       Um, uh, but a great business and like credit to Itai. So, uh, totally there. Uh, listen, I do wanna move into my favorite, which is a quick fire round, my friend. So I say a short statement.

    9. SMSheel Mohnot46:50

       Oh yeah, let's do it.

    10. HSHarry Stebbings46:51

        Um, you ready to rock

23. 46:52 – 47:41

    Favorite books

    1. HSHarry Stebbings46:52

       and roll?

    2. SMSheel Mohnot46:53

       Let's do it.

    3. HSHarry Stebbings46:54

       Listen, you're going on holiday next week. What's the reading material and what's the favorite book? (laughs)

    4. SMSheel Mohnot47:00

       (laughs) So, okay, this is a- a- a embarrassing confession. I don't read books. Um, I haven't read a book in a dozen years. And I've found that like I know authors, I find that like books are too long, and- and- and full of fluff. I get a lot more out of reading articles, long form articles or listening to podcasts. So I don't read books. My favorite book from the past though, from when I was a kid, is a book called Ender's Game. Very famous science fiction book. And I just love that it was written 40 years ago, but had- has so many predictions on the future and it was just like such an entertaining read. I love it. Have- had

24. 47:41 – 48:57

    Biggest strength and weakness

    1. SMSheel Mohnot47:41

       read the whole series. Um, so absolutely love that book.

    2. HSHarry Stebbings47:44

       What's your biggest strength and what's your biggest weakness, Sheel?

    3. SMSheel Mohnot47:49

       I think my biggest strength is I'm willing to try anything, not afraid of failure. And I think sort of the other side of the coin is that's probably my biggest weakness too. (laughs) It's like I'm willing to try things that are stupid. (laughs)

    4. HSHarry Stebbings48:03

       Has there been any time when that's really bitten you?

    5. SMSheel Mohnot48:07

       Yeah, I mean, plenty of times. Uh, I mean, you- you made the joke about- (laughs) about, uh, jumping over pools. (laughs) It's like a stupid thing to do. Um, I'd say like it- it comes with like a sense of adventure, which I think I am willing to try anything and I love ex- new experiences, and you know, I think it- it sometimes doesn't, it doesn't always work out. And so like I've tried businesses that were stupid in hindsight. Um, an example is I- I don't even like vitamins, but like a friend of mine loved vitamins. So I tried building this like automated vitamin company where like you had a quiz that would ask you questions and we had a machine that would spit vitamins customized to you into it. And it was just like, I didn't give a shit about vitamins, so like why did I start this company? Um, I was just throwing spaghetti at a wall and seeing what

25. 48:57 – 49:29

    Hardest element of job

    1. SMSheel Mohnot48:57

       stuck. But-You know, I, I've gotten a little bit more focused over time.

    2. HSHarry Stebbings49:00

       What's the hardest element of your role with BTV today?

    3. SMSheel Mohnot49:05

       Saying no to founders, without question, is just so hard. People are coming at you with their dreams, their aspirations, and in saying no, you know, they take it as a, "You don't believe in my, my dream. My baby's ugly." And it's so hard to do, and I struggle with every single pass message. And I try to be thoughtful and

26. 49:29 – 50:27

    What would you like to change in the world of venture?

    1. SMSheel Mohnot49:29

       helpful as I can, but, uh, I don't always get it right.

    2. HSHarry Stebbings49:32

       What would you most like to change in the world of venture today?

    3. SMSheel Mohnot49:39

       I think, I think there probably still aren't enough people solving hard problems. And even within fintech, there's so many things that I think about on a daily basis, like, "Why is this fo- so fucking hard?" And, like, it requires a major leap to get to, uh, to change this, but I think it's changeable. So I think there aren't enough people solving enough hard problems, and, and we should be funding those things.

    4. HSHarry Stebbings50:04

       Totally agree with you. You can take one luxury on a desert island. What do you take, Sheel?

    5. SMSheel Mohnot50:10

       I don't need any luxuries, so, um, I would take, you know, a box of pizza. Love pizza.

    6. HSHarry Stebbings50:15

       What's your favorite pizza?

    7. SMSheel Mohnot50:18

       (laughs) Uh, I don't have one. Um, in San Francisco, there's a place called The Mill. It's my favorite here. Um, in New York, believe it or not,

27. 50:27 – 52:14

    Does pineapple belong on pizza?

    1. SMSheel Mohnot50:27

       I, I love a lot of the, like, dollar slice places. (laughs)

    2. HSHarry Stebbings50:30

       D- does pineapple belong on pizza?

    3. SMSheel Mohnot50:33

       Absolutely not.

    4. HSHarry Stebbings50:34

       Does chocolate-

    5. SMSheel Mohnot50:34

       It's disgusting.

    6. HSHarry Stebbings50:34

       Does chocolate belong in the fridge?

    7. SMSheel Mohnot50:38

       No. Gets all white and stuff. You don't need that.

    8. HSHarry Stebbings50:40

       (laughs) We ask the important questions here. Just in case.

    9. SMSheel Mohnot50:44

       I don't like any sweet in my main entree. So, like, cranberries in salads, I don't want it. Peaches... I don't want any of that stuff. I like my salty stuff to be salty.

    10. HSHarry Stebbings50:55

        I, I'm tota-

    11. SMSheel Mohnot50:56

        Although... You totally with me?

    12. HSHarry Stebbings50:58

        Yeah, totally with you. Hate it.

    13. SMSheel Mohnot51:00

        Yes.

    14. HSHarry Stebbings51:00

        But I do like chocolate.

    15. SMSheel Mohnot51:02

        Figs on pizza, absolutely disgusting.

    16. HSHarry Stebbings51:03

        But I do like chocolate in the fridge. Oh, yeah. It's what I ask on, like, a date, which is, like, "Hey..." uh, y- the other thing is, I, I say on dates, and it's, uh, probably why I'm single, but I say, like, you know, most dates are fraught with, um, you know, this, uh, hidden, you know, posterior, like, you know, "I'm brilliant in all these ways." I'm like, "I'm fucked up in all of these ways." Like-

    17. SMSheel Mohnot51:21

        (laughs)

    18. HSHarry Stebbings51:21

        ... "Which one would you like to dig into first? Here's your menu of how fucked up I am."

    19. SMSheel Mohnot51:24

        This is great.

    20. HSHarry Stebbings51:24

        Uh, and then, by the way, "Does chocolate belong in the fridge?" And, how they respond to the how fucked up I am, that doesn't matter.

    21. SMSheel Mohnot51:30

        (laughs)

    22. HSHarry Stebbings51:30

        But the chocolate in the fridge, this is a deal breaker.

    23. SMSheel Mohnot51:33

        (laughs) Eh, what's the, what's the math on that one?

    24. HSHarry Stebbings51:37

        Oh, uh, well, I mean, actually (laughs) , uh, I'm arguing against myself. Chocolate, like, scientifically loses flavor when it's in the fridge.

    25. SMSheel Mohnot51:44

        Y- exactly. Yeah, exactly.

    26. HSHarry Stebbings51:45

        I didn't ask for your opinion, Sheel. You come on this podcast-

    27. SMSheel Mohnot51:48

        (laughs) You did. You did, in fact, ask for my opinion.

    28. HSHarry Stebbings51:50

        ... and we... (laughs) So, uh, it does, it loses flavor, genuinely. But I like the crunch. It's like... (smacks lips) And so it's like...

    29. SMSheel Mohnot51:58

        Hmm.

    30. HSHarry Stebbings51:58

        It doesn't melt in the mouth as much. Texture.
28. 52:14 – 53:38

    Next 5 years for BTV and you?

    1. HSHarry Stebbings52:14

       for you, and this is a big one. Okay? What do the next five years hold for you and for BTV? Paint that picture. We're 2027. You're 45.

    2. SMSheel Mohnot52:23

       Mm-hmm.

    3. HSHarry Stebbings52:23

       Um, where are we now?

    4. SMSheel Mohnot52:24

       Yeah. Whew.

    5. HSHarry Stebbings52:25

       Where are we now?

    6. SMSheel Mohnot52:27

       So, um, for BTV, like, our goal with BTV was always to build the fund that we wish we had as founders. And I think in the next five years, we wanna be recognized as such, as, like, the number one place to go. If you're building a fintech startup, you should go to BTV. No matter where you are in the world, they should be your top choice. We're not there yet. But that's where we wanna go. And we wanna build a team around us that helps us get there.

    7. HSHarry Stebbings52:55

       Sheel-

    8. SMSheel Mohnot52:56

       And for myself... Yeah, go ahead.

    9. HSHarry Stebbings52:57

       Yeah. No, no, uh, on, on the personal side, where are you going?

    10. SMSheel Mohnot53:01

        Uh, where am I going personally? I think more of the same. Like, life is, is a fun adventure. I love living it. I love, uh, exploring more places, and hope to continue to do so. Perhaps there's kids in my future in the next five years, perhaps not. You never know. But, uh, I, I would like that, but, uh, you can't predict, especially at this age.

    11. HSHarry Stebbings53:25

        Sheel, I've absolutely loved doing this. I'm glad that I was such a professional interviewer for this incredible description.

    12. SMSheel Mohnot53:31

        (laughs) So professional.

    13. HSHarry Stebbings53:32

        So professional. Uh, I loved it. Thank you so much, man.

    14. SMSheel Mohnot53:36

        Thank you. I loved it too. It was really fun.

Episode duration: 53:43