Henri Pierre-Jacques: How I Founded Harlem Capital; Our $134M Fund | 20VC #901

1. 0:00 – 2:04

   Henri's background

   1. HSHarry Stebbings0:00

      (music plays) "Three, two, one, zero. You have now arrived at your destination." Henri, listen, this is such a joy to do. I'm so glad that we had our Twitter interactions first. Thank you so much for joining me today.

   2. HPHenri Pierre-Jacques0:16

      Thanks for having me.

   3. HSHarry Stebbings0:17

      Not at all. But I wanna start today with a little bit on you. Tell me, how did you make your way into the wonderful world of venture and how did you come to found Harlem and start that journey from the kitchen table with Jared?

   4. HPHenri Pierre-Jacques0:28

      Yeah, I always tell people I kind of bought my way into venture. (laughs) So I, I started out in investment banking at Bank of America, did that for two years, then moved over to a Black-owned private equity firm where Jared and I actually were cube mates. We were working in PE and we basically said, "Hey, like, why don't we do what we're doing at work for ourselves? We're obviously making decent money." Uh, and so we started angel investing, right? So that was 2015, uh, in Jared's living room, in, in Harlem. We all live in Harlem, which is where the name came from. Started angel investing, did that for two and a half years. Uh, Jared and I were both fortunate enough to get into Harvard Business School where we were roommates, and we started recruiting at HBS for, for venture and private equity roles. And most of our angel investing were into diverse, uh, diverse founders, right? Even though that wasn't our mission, our firm was Black-owned. And so, to be frank, you know, going from Bank of America where I was one of 45, uh, one of only 45 in a group of Black people in a group of 45, uh, working at a Black-owned firm, I didn't want to work for a firm that didn't have Black partners, which was 99% of all VC funds. And so I turned to Jared, my roommate in the kitchen and said, "Hey, like why don't we use our angel track record and instead of recruiting, uh, raise a fund?" (laughs) Not fully knowing exactly what that meant. Uh, and so yeah, our summer of July, uh, July of 2018, between first and second year of business school, we formally launched Fund One. Ended up raising $12.5 million, uh, our second year of business school, and then ended up closing on $40 million, uh, November of '19, six months after we graduated. And the pure thesis was just to back, uh, women and diverse founders at the early stage.

   5. HSHarry Stebbings2:02

      Listen, we're gonna get into the fundraise. Uh, I

2. 2:04 – 3:05

   How does mindset change going from angel to institutional investor?

   1. HSHarry Stebbings2:04

      do just wanna ask, I, obviously I have my funds now, but I look at my angel track, I was a shit angel, Henri. (laughs) Like, really crap. Um, how did your mindset change moving from angel investor to now institutional manager, do you think?

   2. HPHenri Pierre-Jacques2:20

      It was pretty scary at first, right? Our first check out of Fund One was $250,000. Our average check as an angel was 28, 25. So like we had 10X the check size and we were like, that was, that was a lot of money. Um, and then, you know, by the time we finished Fund One, 'cause we started deploying, we started deploying capital while we were raising, we were writing 750K million dollar checks. And so I always tell people like, "As you scale your AUM, like your, your comfort level for discomfort, uh, increases." And so like now on Fund Two, you know, our average check size is 2 million, and so I've basically gone from 25K to 2 million in three years. And like, it feels like it'd be really scary, but it actually gets more and more easy as you, you do it for longer periods of time. Uh, and so at first it definitely was scary, um, but I think over time I, I really adjusted to it and it's been a, a great learning experience.

3. 3:05 – 4:45

   The 3 camps of Venture Capital

   1. HPHenri Pierre-Jacques3:05

   2. HSHarry Stebbings3:05

      Now, before you go out and fundraise, you have to put together a plan. You have to think through portfolio mechanics. And me and you both share a love of portfolio construction, and I think we both share a concern that very few managers today at the early stage actually have any fucking clue what portfolio construction is. (laughs) Um, with that in mind, I wanna start on the fund model. And you said first you have to decide what camp you are in. What did you mean by this, Henri?

   3. HPHenri Pierre-Jacques3:31

      Yes, I mean, I basically see three camps. Either your concentrated portfolio, let's say that's sub 20, your diverse portfolio, probably 20 to 45 deals, this is purely for seed stage, or your kind of spray and pray, you know, 45 plus deals, you know, the 80/100, 80/100 portfolios for mostly pre-seed funds or some seed funds. And so, you know, the av- you know, according to Sapphire Ventures, which is one of the best fund to funds, the average seed stage fund has 28 companies in their portfolio. So I would say it's probably, that's diverse, right? And so for us, I think we wanted a balance of, like, diversity, 'cause obviously it's a law of outliers. But a fund, based on the fund size, like can we actually get the ownership we need in that diverse portfolio? Like, we are big ownership believers. Obviously I've listened to a lot of your shows and there's a huge spectrum in ownership matters, and I think fundamentally when we look at, like, who are the funds that we want to be the best investors of the world who've been around for multiple decades. Like, yes, you have to pick the best founders, but, like, there's a reason the best funds have been around for 30, 40 years. Like, these funds are very strict on ownership targets. Like, venture is a math game. Uh, it's not different from other asset classes, private equity, real estate. Like, there is math involved. And so I think for us, like, just when we look at where we want to go and what we're trying to build, it was pretty clear to us, like, what the portfolio construction needs to look like based on where we want to go long term.

   4. HSHarry Stebbings4:44

      I get you. The challenge

4. 4:45 – 6:09

   How to balance diversity and ownership levels

   1. HSHarry Stebbings4:45

      is with the pricing levels that we've seen over the last few years, if you have a small fund, sub $50 million, and you are ownership centric, to get the ownership in the price seed rounds that we've seen, you can't, really.

   2. HPHenri Pierre-Jacques4:58

      You can't be diverse, yeah.

   3. HSHarry Stebbings5:00

      Yeah. And so you have to be low ownership if you are gonna be diverse or you have to be super concentrated, which I do not think is the right strategy. (laughs) And so I guess my question is like, how did you think about that? 'Cause I have the same problem, which is like, you know, our fund's 30 million, I went for very diverse low ownership given the low fund size. How did you think about that?

   4. HPHenri Pierre-Jacques5:22

      Yeah, I mean, the average first time fund in the US is 40 to 50 million. I think that's the spot where you probably can do your, you know, 5% to 8% ownership. That's probably average for the size of that fund. So ownership does change obviously as the s- the size of the fund changes 'cause you need, you need larger returns. So I don't think it's, uh, ownership doesn't matter at a sub 50 million, I think it's just you need less ownership, right? Because a 500 million or a billion dollar outcome for a $50 million fund can return the fund. Now when you start getting into the 100 million, the nine-figure funds, like, that's where you, you have to start doing 10, 15, 20% ownership. Like, the math just doesn't work otherwise. But for sub $50 million funds or a lot of funds are sub 10 million, like, you don't need a lot of ownership because you don't need out- large outcomes to return your funds.

   5. HSHarry Stebbings6:04

      I, I agree totally. I mean, it goes back to kind of a level on pricing. When we think

5. 6:09 – 8:11

   How do you think about your relationship to price?

   1. HSHarry Stebbings6:09

      about pricing, I just had Keith Raboy on the show, and he was like, "The thing I wish I knew from the start of my career in venture, is that seed and A, just price just really doesn't matter." It just doesn't matter. Um, how do you think about your relationship to price, and reflections on it given the time you've been investing now?

   2. HPHenri Pierre-Jacques6:26

      Ultimately the price only matters based on the fund size, right? And so once you kind of decide which camp you're in, let's say we're in the diverse camp, 30 to 45 companies, we decide, hey, for whatever size fund you are, like we need this much ownership. All that really matters is, based on whatever reserve model you have, you know, the average reserve model is one to one pro rata, so let's assume a $10 million or $100 million fund, I'm doing 50/50, I want 30 companies. Like you basically come back into what is the max check I can write to get my ownership? Right? So for us, the $134 million fund, we tell people we invest one to two and a half million dollars for 10 to 15%. Now if that two and a half gets us 10% versus 15, that's going to vary based on the price, or based on the round, but like we can't go below that threshold. Right? The math for us just doesn't work. Uh, and I think it's pretty clear over time, like we have a lot of fund to funds who are LPs in our fund, and if you look at fund to fund data over time, obviously they're outliers, obviously, you know, I was listening to Box Group on your show, like you can get the Coinbase $100,000 check and can return the fund. Right? But if you look at like OverTime, Greenspring, TruBridge, the best fund to funds you've been investing for 20, 30 years, there's pretty clear data like on the ownership and size fund that lead to the 5X net outcomes. Right? And so for us, like we're not targeting to be that one Coinbase outcome, that one Stripe outcome, like we're saying over time, how do we get LPs to know that we can consistently generate three to 5X net returns based on math that's been done over many decades? The market has obviously changed. People thought the market was going to be new the last two years. Obviously the correction has kind of changed that and we're back to reality. You're gonna have these, you know, spurts where things will change and people will say, "Oh, well now you can get these outsize outcomes. So, you know, ownership doesn't matter." Well, yeah, now your outsize outcome is 70% lower value and you're back to normalization. Right? The market's always corrected time and

6. 8:11 – 10:01

   Reserves planning

   1. HPHenri Pierre-Jacques8:11

      time again.

   2. HSHarry Stebbings8:11

      How, how do you think about reserves planning? 'Cause the interesting thing that we have seen a change a lot in venture is like, I don't have any reserves. I would rather be made way more diversified, and then I would rather be super aggressive on SPVs into breakout companies. That changes a lot in terms of dynamics. How do you feel about reserves planning and why you chose the reserves structure that you did?

   3. HPHenri Pierre-Jacques8:34

      Yeah, I mean, so once you decide your bucket, right, if you want to do the p- extreme spray and pray, then obviously you're not gonna have reserves. If you want to be diversified, be the lead. We lead 80% to 90% of our deals, have the board seats. Like there's only so much diversity you can do. Right? So I think there's, there's a lot of constraints as a human. Like for me personally, I don't like SPVs, I don't like all the extra headache. It's not worth it. Our team thinks it's a distraction. We'd rather have one fund. Right? Maybe over time as you get larger we'll have a growth fund that's separate, but it really comes down to what's the team capacity, how many boards can you be on, how many deals can you do, what's the back office, fund administration? Like there's a lot of other nuances that I think people forget. Um, and for us, it's just not worth the headache. And for other, for other GPs it is. There's no right or wrong way. I think ultimately there are a lot of ways to make money in this game, but I think really what you're trying to figure out is, hey, what is the best risk/reward profile? Right? And that's what in- institution LPs are looking for. They don't care if you have one 5X. Right? Like they'd rather take a 2X over 10 funds consistently than a 5X, 1X, 3X, 2X. Right? They want to know do you know how to institut- institutionalize and operate and have processes that allow you to best execute at scale for long periods of time? And that depends on the GP. Like we've been very upfront with our LPs, like I'm 30 years old, I want to do this for the rest of my life, I'm trying to build a multi-billion, multi-asset class business globally. Right? So like I'm positioning myself, but I have other friends who raise funds, they want to stay small, they want to stay, take 10, 25 million, do this for maybe two, three funds. That's a very different perspective on what you're trying to build

7. 10:01 – 11:50

   What nuances do managers miss?

   1. HPHenri Pierre-Jacques10:01

      at scale.

   2. HSHarry Stebbings10:02

      What are the big nuances that you think managers miss?

   3. HPHenri Pierre-Jacques10:07

      I would say the big... 'Cause we invest in fund managers as well, so I've invested in 12 funds. The biggest thing that I learned, you know, TBG was our anchor investor in fund one, and I remember Jim Coulter, the CEO of TBG, he was like, "Ultimately you have two jobs." Right? Invest in deals, and manage your funds. And they're two different skill sets. It kind of reminds me of, of co-founders, right? We love CEOs who are business oriented, and the co-founder being a CTO. It's two different jobs. Fundraising, managing team versus managing the tech. And a lot of fund managers, especially early on emerging managers, think that by being the best deal, deal picker, having the best sourcing, like they're gonna be the best fund manager. You can do that at, at small scale, right? 10, 50 million you can just be a picker, not think about ownership, you know, have maybe no associates, no memos. But like... And that's fine, right? But if you want to scale and be in this business and become the Andreessen's Investments of the world, that's not gonna work. And that, what Andreessen's doing, you know, they just announced their $4.5 billion fund, that's a completely different skill set, has nothing to do with deal picking. Right? When you're that kind of fundraiser, that kind of money manager, that kind of talent hire, that is like I think what the difference is between the goats of the world, to me, who have built institutions, versus great, you're a great angel investor, you're a great picker, that's a very different skill set, and it's not scalable for a lot of people, and I think people underestimate what it means to manage the business side of fund, of VC, versus just the deal side of VC.

   4. HSHarry Stebbings11:27

      I totally agree with you. I think there's... I, I always looked at great investors and I was like, "Why didn't you have your own fund?" And now I have my own fund and I'm like, "I get it."

   5. HPHenri Pierre-Jacques11:35

      (laughs)

   6. HSHarry Stebbings11:35

      All this shit that I have to do is like, fuck, you spend 20% of time with founders, and it used to be like 100% of time. My, uh, my favorite thing is everyone thinks I'm so nice when they listen to the show and then like, the edit is like me swearing and swear fuck. It's-

   7. HPHenri Pierre-Jacques11:49

      (laughs)

8. 11:50 – 14:53

   The state of GP commits today

   1. HPHenri Pierre-Jacques11:50

   2. HSHarry Stebbings11:50

      It's so funny for me. Uh, can I ask, I've got a real problem with something. GP commits. Like, I'm young, I don't have that much liquid cash, but like, oh my god, I'm like up to my eyes in GP commit. And then they, LPs would expect the same from a billionaire founder in terms of percent, which is like his play money. I... How do you feel about the state of GP commits today, and is there anything you'd like to see change?

   3. HPHenri Pierre-Jacques12:17

      Yeah, I think there's a few things that we did that helped. So one, we set our... You know, we did one person who went just standard. Some people have gone less, some people have gone more. We set the one person at the cap, at the, at the target of the fund. Right? So fund one, our target was 25, our cap was 40. We hit $40 million. So we ended up doing 250K instead of 400K. Right? And we said, "Hey, like, 250K..." We were 27 years old, I was graduating from business school. That was still a lot of money. I had $120,000 of business school debt. Right? But we said, "Hey, we think that it should be based on the target. There should be some cap. If we get to the cap, great, but that shouldn't be the GP cap." Second thing we did in fund two which we didn't do in fund one which was help, was get a GP credit line. Right? So basically we used Silicon Valley Bank. They put up 60% of our GP stake, we put up 40% of our cash, and over time it gets paid. That's really helpful, particularly because we raised fund two a year after we placed f- uh, closed fund one. So you start to stack these GP stakes really quickly and you've got no carry. Uh, your, your partner is like, "Where is all this money going to? Are we gonna get it back?" So there, you know, you, you do want to leverage. Like, one of our, uh, one of our LPs in, in fund one, Henry Kravis, like always said, "Y- you want to use other people's money, you know, as much as possible." Right? That's, that's the beauty of finance, it's the beauty of being a fund m- manager. So you want to learn from that. So I think we, we learned from that. And then thirdly, you just want to be honest and open with your LPs, right? And we had a few LPs in fund two that we didn't let in for, you know, whether it was GP sake or other rules, because we just felt like they weren't really humanizing us, right? They kind of were using us as a number. Um, and my partner, Jared, for fun one, like he had a baby three months before we closed the fund. You know, when we closed the fund, that was six months after we graduated business school. We were 27. We had done this angel investing to build a track record for the fund, so we hadn't, you know, just been saving 'cause we were using that as our track record. And so, like, we had LPs that understood that and we said, "Yes, like, y- 1% of 40 million would be great, but, like, we've alre- like, we've already put up a quarter million dollars in the angel portfolio. Like, we're invested in this. We've already sacrificed for business school. We've already put up another quarter million in GP stake. Like, if you don't believe that we're invested in this business, then, like, you're not the right LP for us." Right? And so I think there is a level where a GP ha- a GP has to take a stance and try to have LPs that can really reflect and say, "Hey, like, as a human, every, like, percentage basis of a fund, like, isn't the same because everybody has different scenarios." And I think that's been a really big conversation, particularly for diverse and woman managers because I'm 30, right? And I'm young and I'm not... You know, one of, one of our LPs is Josh Kopelman, right? When he started First Round, like, he had taken a pump- company public, had had a business acquired. Like, a one person GP stake is very different for him, right? And so it's like, do you understand that like, "Hey, I have a different scenario than a Josh Kopelman, than prob- than, uh, Tiger Capital,

9. 14:53 – 17:42

   The first fund Henry raised

   1. HPHenri Pierre-Jacques14:53

      et cetera."

   2. HSHarry Stebbings14:53

      It's also just like fucking hard in the way that like, you know, it takes a while to raise a fund. Not many people can go like six to 12 months, to 18 months, to two years without a salary. I was lucky I chat shit on a podcast. (laughs) Um, but like if I didn't, it would be brutal. Um, I do want to talk about the fundraise itself though, because it- it's always a really interesting journey, I think. You know, you and Jared sitting at the kitchen table. How was the fundraise for fund one? How many LP meetings did you have?

   3. HPHenri Pierre-Jacques15:22

      Yeah, fund one was brutal. (laughs) Uh, it was 18 months long. 12 of those 18 months, we were at Harvard Business School. Uh, and so Jared and I, our kitchen table was our office. We purposely second year only took what we call X classes, which were basically Monday, Tuesday, Wednesday. Right? So every Wednesday night, we took an Amtrak to New York, uh, and we stayed until Sunday and we'd fundraise. And so, like, yeah, second year of business school was kind of rough. Like, didn't do spring break trips. I was in New York all of spring break fundraising. Uh, but like luckily, you know, Jared is one of my best friends. I've known him for 12 years, and so when you're fundraising with your best friend, like that helps. Like, my wife calls him my husband, uh, 'cause I, I work with him so much. Um, so yeah, it was hard, right? And we, you know, we ended up with 55 LPs in fund one. My guess is probably took four to 500 meetings. We got much better at like knowing who, who would likely have a chance, right? So for us ultimately it was like, hey, we had to know, do you back first time managers? Right? Do you have a problem with that? Do you believe in diversity as an asset class? Right? Like, we didn't get into venture because we loved venture. Like, I didn't know anything about venture. Even when I was angel investing, like, I just thought I was investing in companies and businesses, and I came from private equity. Right? And so we got into this game because we believed there was a problem we were seeing, and we're like, "Hey, there's no people of color." We worked at a Black-owned PE firm. We had no Black portfolio companies at our Black-owned PE firm. And so we knew we couldn't start what we were doing at the growth stage, and so we said, "Hey, like, where can we solve this problem? We have to go early stage. We see it in our angel portfolio." And so like, that's why we got into venture. And so we needed people who understood like, hey, yes, we're in this to make money, and we're gonna be trying something that nobody was trying. At the time, you know, six years ago, diversity meant gender equality, right? Before George Floyd in America, all the diversity focused funds were woman-focused funds. There was no racial lens for, you know, investing. There was one or two funds. And so a lot of LPs were like, "Well, what's your thesis?" Like, "What's your industry sector?" We're like, "Diversity. This is 2% of funding." Right? "I know this 2% better than anybody else, and you're gonna tell me that the fintech investor or the biotech investor, which is 30%, 40% of the market is a specialist? Like, how can you be a specialist for 30 to 40% of the market? Like, being a fintech investor doesn't mean anything." Like, there's multiple verticals, there's multiple differences. And so I think the pushback for that was pretty extreme 'cause we were like, "Hey, we know this 2% really well. You're not giving us any credit. You want us to focus on fintech within the 2%. Like, that's too small of a

10. 17:42 – 18:46

    Most common reason people said "no"

    1. HPHenri Pierre-Jacques17:42

       market. We need to take the whole market."

    2. HSHarry Stebbings17:43

       What was the most common reason people said no?

    3. HPHenri Pierre-Jacques17:47

       That was probably one of them. Uh, definitely they didn't, they didn't believe that there were enough diverse startups that could scale and venture.

    4. HSHarry Stebbings17:55

       (laughs)

    5. HPHenri Pierre-Jacques17:55

       Um, which, you know, we were like, "Hey, like, we're trying to invest in 30 companies. There's, let's call it 150, 170 million (laughs) people in the target audience. I think we're gonna be okay." But like it was a real, it was a real pushback 'cause it hadn't been seen before. Um, you know, obviously the first time manager, we were young. Like, I always tell people, like, we were basically one of the riskiest first time managers you can back.... right? We never worked in venture. None of us ever had a start-up, we weren't operatives, we came from private equity, we were 27 years old, we were Black, we were investing in people of color, right? Like, it was, like, all the, like, risks, like, were just thrown (laughs) like, into our fund. Um, and, you know, so we're grateful. We, we ended up with six institutions in the fund, and we had a lot of GPs and family offices, so, like, it was a grind, but I think we really were happy with the outcome, and we had people who saw the vision before a lot of the people came post-George Flory, 'cause Fund

11. 18:46 – 20:44

    How to convince institutions to invest in first time fund

    1. HPHenri Pierre-Jacques18:46

       2 was a, a much easier raise than Fund 1.

    2. HSHarry Stebbings18:48

       Whoa, whoa, whoa, whoa. Six institutions is very impressive. Like, institutions don't normally come in that early, bluntly, especially into managers who are first-time managers. Um, what do you think you did to enable them to gain comfort to invest in a first-time fund and a first-time manager, given they, they rarely do?

    3. HPHenri Pierre-Jacques19:06

       Yeah, I think there are two things. I think the first was we were so left field that it was like either you got it or you didn't, and if you were an institution who had been looking and searching for diverse managers plus diverse founders... Like, the diverse manager piece has been in the LP world for 10, 20 years, right? Emerging manager, diverse manager programs. But people now are like, "Okay, great. We've backed Black GPs similar to my private equity fund, but their portfolio is still white," right? So ultimately, we're helping to make, whatever, five, 10 people of color or women, you know, more successful, but, like, that's not scalable. And so I think LPs have been having this question, and now it's, okay, well, now we have a diverse manager who's investing in diverse founders. Those diverse founders have been proven to hire diverse teams. Like, now you actually begin to get much more deeper network effects. So that was first. And then second, TPG was our anchor in Fund 1, right?

    4. HSHarry Stebbings19:55

       Mm-hmm.

    5. HPHenri Pierre-Jacques19:55

       So one of our, one of our high net worths introduced us to TPG, uh, November of, of 2019- November of '18, and we had a bunch of conversations. We were doing this for five, six months back and forth, met probably 45 partners in a six-month process, and TPG ended up being the anchor for our fund, and once we had them, like they actually were really big advocates for us, right? So we did a big press release on it in The Wall Street Journal. Uh, we had fundraising meetings. Like, we literally went to Boston, I remember, and they had one of their fundraising team members come with us in a car, and we drove to every institution. We went to Brandeis, we went to Harvard, we went to a couple family offices, and, like, they had a rep, like, next to us, uh, who were supporting us. Like, we would do our pitch, and then if they asked any questions about TPG, the rep would say, "Hey, this is why TPG is supporting them." So that was really helpful, and we got two of our other six institutions from TPG. So, three of our six came directly from the TPG relationship,

12. 20:44 – 22:50

    Advice for first time fund managers

    1. HPHenri Pierre-Jacques20:44

       uh, which was super powerful.

    2. HSHarry Stebbings20:45

       Man, I think the biggest thing that managers miss is they say, like, "I need more, I need more LPs," and they say, "Well, go to your existing LP base and say, 'Can you give me three names that you think would be really well aligned that you will vouch for me to?" And people don't leverage the existing that they have to get net new. I always find it astonishing. When you think about advice, uh, like that, which as you said, like, how would you advise emerging managers, first-time fund managers, on lessons that you took from that first process?

    3. HPHenri Pierre-Jacques21:13

       Yeah, I think you, you want to go... So when we first (laughs) launched the fund, it was actually tax day of 2018, and we did this mass email, and we got, like, two responses (laughs) from, like, 100, 100 emails of people who we knew. And so I think the first thing we realized was, like, hey, we have to go really deep, right? We need to, like, be super targeted. So I think even to your advice of, like, asking LPs for three references, like, we went a step further, like, we, we had our first intern class that spring to help us fundraise. And so we literally went through and we scraped every board that every person we knew was on, and we looked at, like, who are the other people on those boards, right? And then we would go onto their LinkedIns and see, like, hey, are they connected to these people on those boards? We would go and see, like, okay, what schools did they go to? You know, what clubs are they in? And so I think, you know, even for founders, for me, when they come and say, "Hey, do you have three people you can invite me to?" I'm like, "Go and look through and then tell me the five. Like, I don't have the capacity to take the time to find those three for you."

    4. HSHarry Stebbings22:05

       Mm-hmm.

    5. HPHenri Pierre-Jacques22:05

       And LPs are the same way, right? When you ask a LP for three introductions, they may give you one or two if they're really nice. Most of them are gonna be like, "Okay, cool," and they'll never get back to you, 'cause they don't have the time. It's not my job to find the people in my network for you. And so I would say even, like, going that extra step and doing the work for them, and saying, "Hey, I looked through your boards, I looked through your LinkedIn. Like, here are the top five to ten people. Can you make an introduction to two or three of them?" That was really wildly successful for us in terms of getting that layer two of LPs.

    6. HSHarry Stebbings22:32

       I think that's a really smart addendum. You're totally right. I find it also with company updates when they're like, "Hey, can you introduce me to NewBank?" And you're like, "Well, if you say I want to speak to Henri, head of partnerships at NewBank, I can see on LinkedIn who's connected." And it's just way easier than, like, NewBank. Do you know what I mean?

    7. HPHenri Pierre-Jacques22:48

       Yeah.

    8. HSHarry Stebbings22:49

       So I totally agree with

13. 22:50 – 24:35

    Biggest mistake I made raising my first fund

    1. HSHarry Stebbings22:50

       you there. What was your biggest mistake in the fundraise for Fund 1?

    2. HPHenri Pierre-Jacques22:55

       Um, I mean, early, I would say the biggest mistake early on, and this is the same for founders, when you're asking people for money, the people with money always seem smarter than you, right? Like, you're a first-time manager. People are giving you advice or flipping your deck literally in front of you, marking stuff up. I remember seeing people X-ing stuff out, like, right in front of us, like, "Oh, they're not investing," right? And so they give you that advice back, and you keep changing stuff. Like, we n- now w- we have probably 200 versions of our Fund 1 deck, right? And th- there was a moment where we, we met with a billionaire, and we turned to him, you know, at the end of the pitch, and we said, "Hey, like, you know, we love your advice, we love your check, we'd love for you to invest." We kind of hesitated, and he said, "Advice is cheap. Ask for the money." And like, it was like this, like, light bulb went off for us, and like, it was like, okay, like, we, you know, we've done at that point maybe 50, 60, 70 pitches. Like, we need to stop asking for advice, right? And so literally after that, we would go into meetings and people would give us advice, we'd be like, "Like, we really appreciate your thoughts. Like, we're gonna be successful or if we're valued, but we'd love you to be on this journey with us. Like, let us know if there's anything we can do to get you over the line," right? And I think, you know, there's a level of, like, cockiness and confidence you have to have. It's a balance, obviously, humility. But, like, you're a founder, right? So I always tell people, like, re- regardless if people say I'm cocky or humble, whatever it is to people, intrinsically, when you're starting a fund, when you're starting a company, you believe you're better at doing something than anybody else that's never been created before. Like, you're basically telling the world, like, "I'm very confident and cocky that I can do this better than seven other billion humans on the planet."... right? And so to some extent, like, you have to own that, right? Own it, have some level of humility, but own it internally very confidently and cockily. And so I think once we had that change, we went into meetings with that, like, kind of swag. We're like, "Hey," like, "we're very confident we're going to succeed at doing this, and we'd love to have you." It changed the, it,

14. 24:35 – 25:49

    Min/Max check sizes from LPs

    1. HPHenri Pierre-Jacques24:35

       like, changed the entire fundraising journey.

    2. HSHarry Stebbings24:37

       Is there any advice you'd have on minimum and maximum check sizes from LPs?

    3. HPHenri Pierre-Jacques24:42

       Um, I mean, so it changes over time, right? So Fund I, we did three closes. The first close, we did 100K minimum, second close was 250K, third close was 500K. Right? As you get further along in the journey, the smaller dollars mean less and less, right? But early on, if I'm like, "Hey, you can give me 100K, I'm raising $25 million fund," like, you'll take it, right? Once I get to $15 million from my first close, I don't need 100K anymore, right? And so I think it, it really should adjust over time. It incentivizes people, also, to move first. Like, I'm not gonna let you wait 18 months to do the minimum check, right?

    4. HSHarry Stebbings25:13

       (laughs)

    5. HPHenri Pierre-Jacques25:13

       Like, you want to do the minimum check, you got to do it today. Otherwise, the minimum's gonna go up.

    6. HSHarry Stebbings25:17

       I agree. But I also, I have some 25K checks in mine, and mine's 150. And they've brought me $40 million. Powerful.

    7. HPHenri Pierre-Jacques25:26

       Yeah, I mean, you, you, you, you set the minimum, but, like, you can always go below it. (laughs)

    8. HSHarry Stebbings25:31

       (laughs) Yeah. Oh, for you, sure. Yeah, everyone else-

    9. HPHenri Pierre-Jacques25:35

       For you.

    10. HSHarry Stebbings25:35

        ... fuck them. No, you're... Yeah, yeah, I totally agree with you. Uh, that, so, for sure. Um, in terms of (laughs) , um, like, you, the people behind the fund, I don't think we talk about, like, actual humanity enough and we're all crushing it, and we're all so

15. 25:49 – 27:45

    What are your biggest insecurities?

    1. HSHarry Stebbings25:49

       amazing, which is wonderful. Um, I'm sitting here going, "I felt like a fucking rockstar Henri for years." Book's way high, you know, numbers are great. And now, I mean, I'm really questioning whether I'm any good at this shit at all. Um, (laughs) , so, like, when you think about your insecurities, what do you think your biggest insecurities are today?

    2. HPHenri Pierre-Jacques26:10

       I mean, honestly, what you just said, right? Like, I, I, I did a thread on this, and it's like, am I actually good at what I'm doing?

    3. HSHarry Stebbings26:16

       Yeah.

    4. HPHenri Pierre-Jacques26:17

       Right? Am I a good investor? And so I think there are obviously KPIs that you can track, right? I can raise capital. I've raised capital already. I can win deals. I can get markups. I can create value add. I can write great content and great Twitter threads and get more followers, right? All these things, like, kind of point to, hey, if I'm a, if I'm a company, these KPIs should lead to generating more revenue or more DPI, returns to my LPs, but it's still unclear, right? Until you get the checks that go to your LPs, you actually don't know if you're good. If you didn't get out before the bubble busted, if you were still in whatever company, you know, Affirm, Coinbase, Robinhood, and you hadn't actually liquidated yet, like, you, you just lost 70% of your value, right? So you still probably made money, but not nearly as much as you thought. Right? And so I think that's my biggest question, is like, hey, am I actually good at this? Like, I know I'm good at the in-between phase, but, like, time will tell, right? I think ultimately, that's the LPs job, that's your job, is to figure out, hey, based on what we've seen historically, if we can execute on these five or 10 things, which is to my point, they want to institutionalize stuff. Like, we fundamentally believe if you can do these things, over time, you will make money. Right? And they've done this. There's been many people who've gone through many cycles. And so I think you just have to kind of ground yourself and like, hey, I really believe that these are the things that are gonna lead to that. But of course, like, in these moments of recession, same thing two years ago during COVID, was asking myself the same questions. Uh, it's like, ultimately, are you really good at your job? And as a venture capitalist, as a GP particular, like, it is so much of your life, right? It's 12 hours a day plus, and it's never off. And so if you're not good at that, like, that impacts you emotionally

16. 27:45 – 30:23

    Biggest investing mistakes

    1. HPHenri Pierre-Jacques27:45

       because it's so much of who your identity is.

    2. HSHarry Stebbings27:48

       What's been your biggest investing mistakes? Mine have been when I've relied too much on other people, bluntly not done the work myself 'cause I've leaned on their knowledge. It's never gone well. Biggest mistakes?

    3. HPHenri Pierre-Jacques28:00

       Yeah, I think early on, particularly the, coming from private equity to venture, it took me a while to be comfortable being uncomfortable, right, and really figuring out, like, what the right risk/reward profile is. 'Cause ultimately, to your point of, like, price, like, the price is all based on what I think the reward's gonna be. Um, that tells me the risk profile. And so I think I was looking for too many checkboxes early on. Like, you want, I want a great market with a great founder and a great business, and I want my ownership targets, right? (laughs) Like, you just can't, you can't get all four of those. Uh, and that's, like, that's our box. Like, our investment box is founder, market, business, ownership. Right? Ultimately, if we have two of the four that are really, really great, like, we're gonna invest. If you have three good ones, we might still invest, right? But we need two of them to be great at least. And so, yeah, I think that was really hard for me. I think we probably, early on in Fund I, overindexed two companies that, like, really fit that box. And oftentimes, like, the best founders and the best businesses don't perfectly align to that. I think it's really true for GPs. You know, I push back on LPs, like, "You're looking for these check the boxes." And, like, all GPs aren't gonna fit into these perfect boxes of working in venture and, you know, doing a spinout, whatever it may be, or having a great angel track record 'cause they were already rich. Right? Like, those things just aren't gonna line up for you as a LP. Like, you got to take risks. And same for me, I need to take risk on certain founders, and that took time. And you know, there's a quote, I forget who said it, but, like, "You don't know a one in 1000 company until you see 1000 companies." And so to some extent, like, you just needed time, right? Like, you're just not gonna be your best. Like, every year, we invest in companies where I'm like, "Wow," like, "I wouldn't have invested in that company we did last year," just because now I'm smarter, I've seen more deals, I'm getting better deal flow, my brand's bigger, and that's okay. Right? You should expect that. You should expect to get better every year, and it shouldn't be like, "Hey, that company I'm invested in last year was a bad bet." It's just, I'm just a better investor now. I'm seeing better deal flow, and I'm winning better deals. And that's gonna continue to evolve as my career evolves.

    4. HSHarry Stebbings29:47

       Yeah. No, listen, I totally agree. I think the interesting thing is, like, you have this, like, if you think about it on a graph, you have this, like, start here and then you go up and get better and better, and then you have two outcome scenarios that can happen. One, you go down with complacency and with wealth, whereby you're no longer front of funnel for distribution, you're no longer at the coal mine, like, finding the best founders. Or two, you become Sequoia, which is, like, you've made so much money that, A, your brand is so big, but also, you lose all downside risk.

    5. HPHenri Pierre-Jacques30:14

       Yep.

    6. HSHarry Stebbings30:14

       And so you think bigger than everyone else. And it's just, I, to me, it's fascinating kind of the alternating paths that you can take post

17. 30:23 – 31:44

    The things on which you won't accept feedback

    1. HSHarry Stebbings30:23

       that, like, mid-tier. So I totally agree. I spoke to Jared before the show, and he told me that you're wonderful in many ways, but he told me you are bad at accepting feedback. Um, and you won't accept feedback on some things. What are the things you won't accept feedback on? And, and why do you think that is?

    2. HPHenri Pierre-Jacques30:42

       That's funny, from Jared. (laughs) Um, I mean, you know, I think, w- one of your strengths are always your weaknesses, right? So for me, being stubborn is one of my greatest strengths and one of my greatest weaknesses. I think to the extent of being a GP or being a founder, you have to be stubborn 'cause then it enables you to do things that people told you not to do. Right? I'm very quantitative. Uh, I love math, I love data, I love analyzing things. So I'd say my biggest thing is, like, when I have a belief, it's gonna take me longer to change my position unless you've kind of, like, shown me the data, shown me the proof. There's obviously things that are just qualitative, but, like, as a quantitative mind, like, that's... The quant part gets me over the line faster. And you know, now I've known Jared for 12 years, and so he's gotten better at learning, like, how to (laughs) , how to present information in order to change my mind. But, like, I definitely can be stubborn, uh, with things like that unless I see, like, the data and quantitative. So we've been doing a lot of back and forth the past two months with the recession talks. Uh, is it a bear market? Is it not? How do we present this data to our founders? Uh, and so, you know, that's just, that's- that's my edge. Like I- I love data and I think, for better or worse,

18. 31:44 – 33:23

    Do you feel you've quashed partners before?

    1. HPHenri Pierre-Jacques31:44

       it can sometimes trap you.

    2. HSHarry Stebbings31:46

       Do you feel that you've quashed partners before in terms of new deals? I spoke to Brandon before the show, and he said there was a learning process where, bluntly, I- I- I do the same, it's not a great trait, which is where you can crush people too fast, too soon when they bring an investment to the table, and you need to give them the room to get there on their own.

    3. HPHenri Pierre-Jacques32:08

       Yeah. That was definitely a learning experience, right? Brandon was our first new partner. Um, we, I've obvious- I've known him for a long time, too. I think you underestimate the value of your opinion, right? There we're a flat, a flat organization. We only have seven employees now. Like, one- one thing we do now is the junior person always goes first after we have an investment committee. So we go associate to principal to partner to GP, right? And so for everything, for opinions, the general partners always go last, right? Because if the GP's talk first, even though your opinion and your vote matters more, like, we don't want that to impact the vote and the- the opinions of the juniors, or- or the junior partners. Right? So that- that definitely took some time, um, to understand. I think now it's more like, "Hey, I want to say something, but, like, let me hold it and let me let the- the rest of the team kind of share their viewpoint. And then we can, at the end, me and Jared will step in and kind of share our viewpoint." I think that's really helped a lot, but early on wasn't something that we were conscious and aware of.

    4. HSHarry Stebbings33:04

       I think one thing that I've also done is, like, being aware of the weight of words. I make people comment on Word docs, not on Google Docs, because then they send them back to me the night before, and then I can pick on them in the meeting and say, "Hey, in the Word doc you said this." And their opinion is unencumbered by others, where it would be in a Google Doc and you see the

19. 33:23 – 34:56

    What are you scared of?

    1. HSHarry Stebbings33:23

       real time. Do you see what I mean? You have, like, the purity-

    2. HPHenri Pierre-Jacques33:25

       Yeah.

    3. HSHarry Stebbings33:25

       ... of thought there. Tell me, what are you scared of, Henri?

    4. HPHenri Pierre-Jacques33:30

       Um, honestly, my big- one of my biggest fears is, like, not accomplishing everything I know I can. Right? And so I think ultimately, we're both very successful. We're top, you know, 1%. My family came from Haiti. My mom came from the Tren... I know my privilege. I know my blessings. And so I- I'm not, you know, I don't have r- many regrets. Um, but I think it's, I know that... W- our mission is to back a thousand diverse founders. And every founder we back obviously matters. Every life we change obviously matters. But I know we can do so much more and we set that mission of a thousand founders over 20 years for a reason, right? Because we believe that in order to have true train- change, in order to really change venture capital, change the wealth gap in America between people of color and whites, like, we have to do this at scale, right? And so for me, that's what keeps me up at night, is like, hey, are we doing everything we can to scale this business, help as many founders as possible, to change the mindset of- of many people as possible? Which is why we're so media-driven, like, we, why I tweet so much, why we do so much press, is because we believe you can't be what you can't see. And for a lot of people, they don't have that in their life. Like, we were very fortunate. We worked at a Black-owned PE firm with a billion-plus dollars of AUM. Like, Willie was our first investor, Willie inspired us. Like, we could see it, like, oh, like, wow, like, there are managers of color who have a billion-plus, which is very rare. But, like, he was my mentor, right? Most people won't get that chance to see that. And so, like, I want to be that for as many people as possible. Like, my- my single mission in life is to create the most minority millionaires of all time. Right? I do believe we

20. 34:56 – 36:27

    What are the barriers to you achieving your goal?

    1. HPHenri Pierre-Jacques34:56

       can do that. Um, and so that's really what keeps me up at night.

    2. HSHarry Stebbings34:58

       What are the barriers to you achieving that? Is it a pure access to capital? Is it a... B- for me, it would be building the machine around me. I'm great at what I do, but I need machinery to make it all happen, and that's my biggest challenge, and that's the question mark around me, I would say. What's yours?

    3. HPHenri Pierre-Jacques35:17

       Yeah. I- I mean, def- capital's definitely one, right? Particularly if I look at, you know, we're now the probably third or fourth largest Black-owned VC fund, which is kind of crazy. Right? So capital is definitely something you think about, 'cause, like, the reality is, like, dollars aren't flowing to minorities and there's a cap. Um, and I would agree. I mean, I think everything, like, everything in life is a people's business, and so I'm very focused on the team. Like, I think... I- I did a tweet about this. Like, oftentimes, they tell you to focus on the customers if you're a founder, or for GPs, focus on the founders, like, be founder-first. Like, I'm team-first. Like, I'm gonna be successful because my team is the best team they can be and they can execute. Like, I've already seen a difference of going from two people to seven people, to your point, right? Going from 80% founders to 30% founders. Like, my job now is not, like, just to help founders. Like, my job is to enable my team to be as most positioned as possible. And that's only gonna continue to exacerbate as I have more team members. And so I think about that a lot, like talent. Right? Talent, to me, is- is number one. If we can hire the right talent, we can build a brand that can recruit the best talent, which our intern program has done. We've had 76 interns over four years, and we've hired five of them so far. Like, that is what, to me, will enable

21. 36:27 – 38:42

    How do you manage so many interns?

    1. HPHenri Pierre-Jacques36:27

       us to, like, get to where we need to go.

    2. HSHarry Stebbings36:29

       Fuck. 76 interns? That takes machinery. Talk to me about that. How do you do that efficiently?

    3. HPHenri Pierre-Jacques36:36

       So we do three intern classes a year. Six interns per class, so winter, summer, uh, and fall.... it's for part-time remote, so 10 to 15 hours a week. It's remote as long as you're based in the US. Uh, and we've gotten really good at it, right? Our first intern class was spring of, uh, 2018. Gabby, who's our, our principal on the team, was our first intern class. Uh, and we did that intern class to fundraise. We're like, "Hey, we need to build a deck, we need a data room, let's go get some interns." And what we realized was, like, we were looking for two, we ended up hiring four 'cause they were so good. And we had... In that first intern class, we had 125 applications. Right? And we were just two kids in business school who didn't have our fund yet. You know, now, our, our last intern class, which starts in two weeks, we had 1,250 applications, right? We hired six. So I think over time, we just realized, like, one, we have a really big brand, there's a ton of diverse people who are trying to get into venture. Like, regardless if we hire them or not, like, it's great for us, 'cause we get to leverage them. It's probably our greatest asset. Like, people, like, see our deal memos, which are 50, 60 pages. Like, how do you do it? We're like, "Well, we have great interns." I don't- I haven't done a deal memo in two years. Like, my interns do my deal memos. Right? But also, what we saw was, like, hey, in order to get to a thousand diverse founders, like, Harlem Capital cannot be the centerpiece for that to happen. Right? And so of those 76 interns, 24 now work at other VC funds. Like, that, to me, is probably one of the most proud stats I have, because I'm like, now we're creating the future investors and we're creating diverse investors at other funds, some diverse funds and some white funds, right? Where we need that one diverse mind to be at Andreessen, to be at Forerunner, wherever it is, to speak and advocate for diverse founder, if it's not gonna be a Harlem Capital company. We only invest in 15 companies a year, right? And so I'm like, I need other funds to actually help me on this mission, and the intern program, for us, has been an accelerant to how do we change the landscape faster, versus saying, "Hey, Harlem Capital, seven people, we're gonna change diversity in venture." Like, that's just not true. But our intern program can help us say, like, "Hey, we're gonna make a big impact," because people come to us now because they know we're in- we're hiring six of a thousand people. Like, we see the best diverse talent in the market, by far, for venture.

    4. HSHarry Stebbings38:38

       I totally agree, and I love the widespread impact you get from it.

22. 38:42 – 42:32

    Deal memos

    1. HSHarry Stebbings38:42

       Final one before we move into a quick fire, but I'm just intrigued. Deal memos help clarify thought, bring clarity to investment decision-making. By not doing it, do you not lose out on that clarity and validation of why you're doing the deal? And then also, like, 50, 60 pages, Henri, man, I think, you know, you're fantastic. But 50, 60 pages? It's early stage. What are you putting in there, an encyclopedia? Like, what? (laughs)

    2. HPHenri Pierre-Jacques39:08

       So, (laughs) fir- first, it's in PowerPoint, not Word, 'cause I don't believe in Word docs. Um, and a lot of investors have, you know, different views on that. But I think, you know, there's kind of, there's three reasons, right? So the first reason is, we want all the information, you know, so this includes customer references, it includes founder references. Like, I don't want to send the other partner who's on the deal, "Hey," like, "here's, here's a Google folder that has five different Word docs with all the customer references." Like, "Go and read them." Like, I, like, nobody has time for that, right? "Give me the document, put all of the stuff that you did into one document and say, 'Hey, here's a document that has all of our due diligence process over two to three weeks.' Read this document, come back, give me your feedback." Right? So part of it is, like, streamlining the process. People think it actually, like, slows it down. It doesn't. We do deals in, as fast as 48 hours, 72 hours. We can do a 30-page deck that fast, right? The second piece is, to my point of, like, what processes are you doing to scale? Like, how did we get six institutions in fund one? We did deal memos for our angel syndicate, right? So when people are trying to validate our ang- "Hey, you picked these companies, great, you've made money. How do I know you've actually institutionalized that?" We said, "Hey, here's our..." At the time, you know, when we were angels, they were 30-page memos. "Here's our 30-page memo, here's why we chose the decision. Like, let's have a conversation." Right? Institutions love that. Like, they care about, like, processes. Thirdly, when we, we lead most of our deals, right? So the way we close a lot of our rounds fast, like, we, we close the deal, we do whatever, a $2 million check on a $4 million round, and then when people get late, when they got to a partner meeting, we allow our founders to send our memos to the other, other funds. So we say, "Hey," like, "don't even go waste time." Like, "Here is, like, 60 pages of work. You probably won't do more work than us. Like, use this to get it faster." And then our founders love it. So we do a launch call after we invest for an hour, and we basically give the memo to our founders and we say, "Hey," like, "we basically have gone through your data room. Like, we spent hours asking questions. Here's all the work we did. It doesn't mean we don't see risk in your business. Like, we still see risk in your business, but we thought there was higher reward than the risk. We want you to know where your flaws are, and we want you to be able to ask us the questions." 'Cause we did this in private equity. In private equity, we would do a two-day retreat after we invested. We would go to the management team, we would fly in all the consultants we use, and we basically would have the consultants present to the management team and say, "Hey, we're investing in your company. Like, here are where the mistakes are, and here's what we think we can gain value over five years." I think too many founders believe if somebody invests, they just believe in me. Like, that's not true. We still saw a lot of risk. There still were a lot of references where maybe they saw flaws in you, or you had bad founder references. But, like, for whatever reason, we took that risk, because we believed the rewards, reward's higher, and that founder has no idea. And every founder we've ever given our memo to always says the same thing. "I've never seen an investor memo before. This is super helpful to understand how investors think. It's super helpful to see where my weaknesses are. I really appreciate it."

    3. HSHarry Stebbings41:45

       Uh, that, and then, you're absolutely right on subsequent financing there. To be able to provide that to subsequent investors, or co-investors in a round, to short circuit their decision-making, it helps a lot. But I totally agree with you there. Um, I, I don't do anywhere near that much work, so congratulations. (laughs)

    4. HPHenri Pierre-Jacques42:02

       (laughs) You need interns. (laughs)

    5. HSHarry Stebbings42:04

       Uh, no, it would just be far too tiring. Also, like, the intern program, it sounds wonderful. I'll take this bit out. Sounds wonderful, but fuck me, it's tiring. No, no, no. Okay.

    6. HPHenri Pierre-Jacques42:13

       (laughs)

    7. HSHarry Stebbings42:14

       But y- y- you're, you're missing something here, my friend. It's about minimizing headcount and maximizing AUM. Big lesson of the day. (laughs)

    8. HPHenri Pierre-Jacques42:21

       They're not, they're not, they're not FTEs. (laughs)

    9. HSHarry Stebbings42:24

       They're, they're, ah, wonderful. This is a smart man. Uh, listen, I want to move into a quick fire round, so I say a short statement, you give me your immediate thoughts. Does that

23. 42:32 – 42:51

    Favourite book

    1. HSHarry Stebbings42:32

       sound okay?

    2. HPHenri Pierre-Jacques42:33

       Let's do it.

    3. HSHarry Stebbings42:34

       Okay. So what's the favorite book, Henri?

    4. HPHenri Pierre-Jacques42:37

       So I'm not a, I'm not a big reader. Um, I'm a big podcast listener. And, and right now, I'm definitely obsessed with, uh, with All In.... with Chamath and Jason, and I, I listen to it every Saturday.

    5. HSHarry Stebbings42:47

       I mean, yeah. It's, have you listened to the Bill Gurley, Brad Gersten one at the All

24. 42:51 – 43:25

    What have you recently changed your mind on?

    1. HSHarry Stebbings42:51

       in Summit?

    2. HPHenri Pierre-Jacques42:52

       Yep.

    3. HSHarry Stebbings42:52

       Yeah, that was-

    4. HPHenri Pierre-Jacques42:53

       Phenomenal, phenomenal.

    5. HSHarry Stebbings42:53

       ... a very, very good one. What have you recently changed your mind on, Henri?

    6. HPHenri Pierre-Jacques42:58

       Uh, I moved to Miami a year ago after living in New York for, for eight years, and I think I've realized that productivity isn't tied to the number of hours you work. Uh, and Miami really forces you to realize the value of living life and that you can be productive and not grinding all the time. That was a, a big shift coming from the hustle city of New York for me.

    7. HSHarry Stebbings43:19

       So you work less, but are more productive? Is that what you're saying?

    8. HPHenri Pierre-Jacques43:22

       Correct. More efficient.

    9. HSHarry Stebbings43:24

       Yeah.

    10. HPHenri Pierre-Jacques43:24

        You just,

25. 43:25 – 43:51

    Tips on time management

    1. HPHenri Pierre-Jacques43:25

       you, you, you're forced to.

    2. HSHarry Stebbings43:28

       Tell me, biggest tips on time management.

    3. HPHenri Pierre-Jacques43:32

       Um, you gotta block stuff off on your calendar, workouts, date nights, et cetera. And if you do have a partner or you do have kids, having a shared calendar is a, a lifesaver. Um, so w- my wife knows every time I have a meeting or event and she can decide if she wants to come or not. There's no question, "What are you doing tonight?"

26. 43:51 – 44:34

    Secret to a great relationship

    1. HPHenri Pierre-Jacques43:51

       And that's a, a big time saver.

    2. HSHarry Stebbings43:54

       I always say the secret to a great relationship is you laugh together, you grow together, and then, uh, you trust each other. That's the three for me. When you think about, like, the essence of a truly great marriage, what would you say it is for you?

    3. HPHenri Pierre-Jacques44:07

       Um, I mean, she's my best friend, right? And so I think ultimately it's, it's, to your point, like, we, we challenge each other but we have fun together, and we support each other and we question each other, right? I think it's, it's just like a... It's a long-term friendship. The, the love emotion will only last you so long, right? And so I think it's about how are you building that partnership together, and I really view her, like, we call each other partners. Like, I view her as a partner, uh, and, and she's my greatest asset, right? I'm gonna ensure that, like, my greatest accent- asset

27. 44:34 – 45:30

    Who do you look up to in Venture?

    1. HPHenri Pierre-Jacques44:34

       thrives and, and, and does well.

    2. HSHarry Stebbings44:36

       Who do you look up to and learn from in venture, and why them?

    3. HPHenri Pierre-Jacques44:41

       So Neha, Neha Mehta, ENIAC, is probably one of my, my favorite LPs, uh, and to your point, smaller check but phenomenal upside. And just, like, somebody who's built, you know, five funds, is such a human, and I just love what they've built and what ENIAC has done to humanize venture, and that's really what we are trying to do at Harlem Capital. Like, it's not this quantitative, like, we're not just like LP hungry. It's like, "Hey, like, we're all humans, let's enjoy this experience. We know we're all going through trauma," especially the last three years, right? And so I, I really appreciate Neha's perspective on, like, "Oh, like, you know, COVID's happening. You know, what are, like, what are you guys saying to your founders? Like, how are you thinking about that?" Right? "How are your founders doing? Like, are family members dying?" Like, those questions, I think a lot of other GPs and LPs don't ask. Um, I think they're

28. 45:30 – 46:36

    Biggest advice to first time fund managers

    1. HPHenri Pierre-Jacques45:30

       really valuable and I think a lot of founders appreciate you being thoughtful about them.

    2. HSHarry Stebbings45:34

       What's your biggest advice to first time fund managers?

    3. HPHenri Pierre-Jacques45:39

       Um, learn to not take the nos personally. The first people you go to in the beginning are going to be your mentors, the people you worked with. And everybody who I thought was gonna back me, most of them didn't (laughs) . And it really, it really hurts, right? It's like, I remember my best friend's dad turned me down. I'm like, "If my best friend's dad, who I know has money, isn't investing in me, like, we're in trouble." And I remember my dad, I called my dad 'cause I was, like, kind of crying, and I was like, "Hey, it's not gonna work." And my dad was like, "If, if people don't think your dreams are crazy, you're not dreaming big enough." Right? "Like, don't take it personally, it just means you have a really big dream and, like, it's okay. Like, keep on pushing." And 12 months later, my best friend's dad came in as an LP at the end. I let him in below the minimum 'cause I wanted him. Um, but I think that, like, that part from my dad, like, really spoke to me, and I think it just made me realize, like, it's okay. Like, to your point of b- to my point of being a founder, like, you're pretty cocky that you think you can do something better than anybody else. But, like, that also means a lot of people

29. 46:36 – 47:30

    Single biggest thing you'd like to change about LPs

    1. HPHenri Pierre-Jacques46:36

       are gonna believe you can't do that, and that's kind of hard to impact.

    2. HSHarry Stebbings46:40

       What is the single biggest thing you'd like to change about the world of LPs?

    3. HPHenri Pierre-Jacques46:45

       Um, I would like LPs to take more risk on GPs. I think they have their check the boxes, track record, what, you know, who are your co-investors, yada, yada. Which historically have shown some outcomes, but I think we're in a time where whether it's solo capitalists, or it's diverse GPs, or it's smaller funds, or micro-funds, like, a lot of the past data just isn't as relevant for, you know, the data that we're using today. And so I think it's, hey, you're asking GPs to take risks, but, like, you need to take risks. I, I, I say the same advice to GPs. Like, VCs are, like, we're asking founders to put all their eggs in one basket, and a lot of VCs are pretty conservative. Like, don't ask somebody to take a risk if you're not taking risks. So I think it, it goes down the scope. LPs take risks, GPs need to take risks,

30. 47:30 – 48:33

    Most recent publicly announced investment

    1. HPHenri Pierre-Jacques47:30

       and founders need to take risks.

    2. HSHarry Stebbings47:33

       Tell me, what's the most recent publicly announced investment and why did you get so jacked and say yes?

    3. HPHenri Pierre-Jacques47:39

       For me, a company called Mushy, which is a high-end NFT marketplace platform for artists who are basically converting their real life artwork to NFTs. Um, so Ariana, black female founder based here in Miami, I met her during Art Basel at one of our events. Uh, and I'm really excited, like, I love her, her focus, I love her connections to the galleries from distribution standpoint. But honestly the thing that's been best is, like, our friendship. Like, I now, she goes to my church with me, she's best friends with my wife, they golf, and, like, we didn't know her five months ago, and now she's really ingrained. And so it's been really awesome to have founders in Miami, uh, invest in two companies here now, and really, like, get to know them as humans. Um, that's what I'm most excited about.

    4. HSHarry Stebbings48:21

       Henri, thank you so much for putting up with my wayward English, uh, schedule, and also, uh, a much more real Hari than I normally show. Uh, it's been so much fun man. Thank you so much.

    5. HPHenri Pierre-Jacques48:31

       Thanks for having me.

Episode duration: 48:33