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

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

The Twenty Minute VCJun 24, 202248m

Harry Stebbings (host), Henri Pierre-Jacques (guest)

Henri’s path from banking and private equity to founding Harlem CapitalTransition from angel investing to institutional fund managementPortfolio construction, ownership strategy, pricing, and reserves planningFundraising tactics, LP dynamics, and GP commit structuringDiversity as a core investing thesis and market opportunityBuilding an institutional VC firm: team, processes, and intern programPersonal psychology: insecurities, stubbornness, and long-term mission

In this episode of The Twenty Minute VC, featuring Harry Stebbings and Henri Pierre-Jacques, Henri Pierre-Jacques: How I Founded Harlem Capital; Our $134M Fund | 20VC #901 explores from Harlem Kitchen Table to $134M Fund: Henri’s Venture Playbook Henri Pierre-Jacques recounts how Harlem Capital grew from friends angel-investing in a Harlem living room to managing a $134M institutional fund focused on women and diverse founders.

From Harlem Kitchen Table to $134M Fund: Henri’s Venture Playbook

Henri Pierre-Jacques recounts how Harlem Capital grew from friends angel-investing in a Harlem living room to managing a $134M institutional fund focused on women and diverse founders.

He dives into the mechanics and math of portfolio construction, ownership targets, pricing, and reserves, arguing that venture is fundamentally a numbers game that must be institutionalized.

Henri details the grind of raising Fund I as a risky first-time, Black-owned, diversity-focused manager, the pivotal role of anchor LP TPG, and the tactics he used to convert interest into commitments.

He also explores team-building, an unusually powerful intern program, his own insecurities as an investor, and the long-term mission to create minority millionaires and back 1,000 diverse founders.

Key Takeaways

Decide your portfolio 'camp' first to drive all fund mechanics.

Henri frames seed funds as concentrated, diversified, or spray-and-pray; once you choose your camp, you can back into number of companies, ownership targets, check sizes, and reserves based on fund size and return goals.

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Ownership targets must be math-driven and fund-size dependent.

He emphasizes that venture is a math game: small funds can win with lower ownership because smaller exits can return the fund, but nine-figure funds often need 10–20% stakes to realistically achieve 3–5x net outcomes.

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Use institutional-grade process (like detailed memos) as a competitive edge.

Harlem Capital’s 30–60 page investment memos consolidate all diligence, impress LPs, help close co-investors faster, and give founders rare insight into how investors perceive their strengths and risks.

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Fundraising requires targeted networking and explicit asks, not generic outreach.

Henri moved from mass emails and advice-seeking to highly targeted, research-driven introductions and direct money asks, and leveraged early LPs (especially TPG) for second-order introductions and social proof.

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GP commits should be negotiated to reflect actual human circumstances.

He structured his GP commit on the target (not eventual cap) and used a GP credit line, arguing LPs must recognize that 1% from a 27-year-old with student debt is not the same as 1% from a wealthy serial founder.

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Build scalable impact through talent pipelines, not just direct investments.

Harlem Capital’s intern program (76 interns, 24 now at other VC funds) functions as a leverage point to seed diverse investors across the ecosystem, extending their diversity mission far beyond their own portfolio.

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Embrace the identity shift from 'deal picker' to 'fund business builder.'

Henri argues that great fund managers must excel at both investing and running a firm—hiring, ops, fundraising, and processes—and many emerging managers underestimate how distinct and demanding that second job is.

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Notable Quotes

Venture is a math game. It’s not different from other asset classes.

Henri Pierre-Jacques

Advice is cheap. Ask for the money.

Unnamed billionaire relayed by Henri Pierre-Jacques

We didn’t get into venture because we loved venture… we got into this game because we believed there was a problem we were seeing.

Henri Pierre-Jacques

My single mission in life is to create the most minority millionaires of all time.

Henri Pierre-Jacques

If people don’t think your dreams are crazy, you’re not dreaming big enough.

Henri’s father, as quoted by Henri Pierre-Jacques

Questions Answered in This Episode

How can emerging managers practically determine the right balance between diversification and ownership given their specific fund size and strategy?

Henri Pierre-Jacques recounts how Harlem Capital grew from friends angel-investing in a Harlem living room to managing a $134M institutional fund focused on women and diverse founders.

Get the full analysis with uListen AI

What concrete frameworks can LPs adopt to more fairly evaluate first-time, diverse GPs without over-relying on traditional track record checkboxes?

He dives into the mechanics and math of portfolio construction, ownership targets, pricing, and reserves, arguing that venture is fundamentally a numbers game that must be institutionalized.

Get the full analysis with uListen AI

How replicable is Harlem Capital’s intern-driven model for other small funds, and what are the key pitfalls in trying to scale something similar?

Henri details the grind of raising Fund I as a risky first-time, Black-owned, diversity-focused manager, the pivotal role of anchor LP TPG, and the tactics he used to convert interest into commitments.

Get the full analysis with uListen AI

In what ways might heavy process and long memos at the seed stage improve—or hinder—speed, conviction, and creativity in decision-making?

He also explores team-building, an unusually powerful intern program, his own insecurities as an investor, and the long-term mission to create minority millionaires and back 1,000 diverse founders.

Get the full analysis with uListen AI

How should GPs and founders thoughtfully assess whether they are actually good at what they do, given that true performance feedback in venture takes a decade or more?

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Transcript Preview

Harry Stebbings

(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.

Henri Pierre-Jacques

Thanks for having me.

Harry Stebbings

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?

Henri Pierre-Jacques

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.

Harry Stebbings

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

Henri Pierre-Jacques

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.

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