John Henry - Raising $40,000,000+ and Making 17 Investments In Women and Minority Entrepreneurs

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What is going on, everyone? Casey Adams here. Welcome back to the Rise of the Young podcast. On today's episode, we have John Henry on the show. John Henry started his first business at 18 years old, which was an on demand dry cleaning service for the film and TV industry in New York City. He led the company through its acquisition in 2014, founding and selling his first business by the age of 21 years old. He then co founded venture capital firm Harlem Company Capital and raised over $40 million and made 17 investments in woman and minority entrepreneurs in his time there. That being said, before we dive into the episode, I want to give a big shout out to Hugo Sanchez for connecting me with John. Hugo's been a mentor for myself and for John Henry and we talk about how John actually met Hugo and what an impact that that that one connection made on his life. So before we jump into it, please take a moment to share this episode with a friend. Post it on your Instagram story. Tag John. Tag myself. And last but not least, enjoy the episode.

All right, what is going on, everyone? Kacey Evans here. Welcome back to the Rise of the Young pop podcast. Today we have John Henry on the show. Thanks so much for coming on the show, John.

Yeah, man. Pleasure to be on.

So first off, John, I am super impressed with your story. You've not only sold a company at 21, but what you've built at Harlem Capital and everything you guys are doing in that community in Harlem is just absolutely amazing. And for those that may not know what it is that you're up to, I'd love you to give us a quick, quick just update on what you're currently working on before we dive into the story.

Yeah, yeah, sure. Right now I Am in the phase of my life where I'm focused on accumulating assets. I've been through a number of businesses, from venture capital funds to on demand types of companies, incubators. And I've emerged from that with a renewed sense of how important it is to own assets because it just sets you up to kind of hit your peak potential down the road in your life. So that's what I'm working on now. And that could be through real estate, that could be through operating businesses, buying them, building brands, media, TV deals, you name it. If it fits in there, I'm doing.

It for sure, man. And I know that the other day when we were chatting with Hugo, we were talking about just the current environment of the economy and how things have shifted. And I know that you had just an interesting perspective there. So I'd love for you to touch on just, you know, how have. How has the current situation of the economy changed your business and what you're doing with lockdown, being in New York and how everything was shut down. How's it been for you?

Yeah, it's a crazy time, you know, Crazy time for not just me, but for, you know, the. The world at large. Which is what makes this moment in time so spec, you know, just so distinct. I mean, in 08, we had a Wall street crisis, you know, where the stock boys got a little too far ahead in their skis, packaging up, you know, shitty loans and making them look good and selling them for a premium. And when that collapsed, you know, the bailouts were mostly for Wall street, which, you know, what they deserve because they got into their own hot water in the first place. But this, man, this is different. This is for Main Street. This is a Main street crisis where regular people with regular jobs across the spectrum, hospitality, retail, oh my gosh, events, live performances, Disney. I mean, yeah, this has just been on an unprecedented scale, massive, you know, interruption in life and business. And it's meant a lot of different things for a lot of different people. For me, I definitely have been fortunate to be in a strong position during a time like this because of the way that I can earn income. However, it's got me feeling like, man, I'm just extra mindful because I have people in my direct family that, you know, have to go and clock in and work. And it's just so evident to me, man, that there's two different realities.

Yeah.

And I'm just walking away of with this feeling like, okay, I have a responsibility since I have developed a certain business acumen and I Can make deals happen and I can raise capital. Like, I have a responsibility to have outsized impact via my business ventures. So I don't know what that yet looks like, but I just, that's how I'm feeling as of late is guys like you and I who have been fortunate to be exposed to a lot of stuff early.

Yep.

We got to keep. We got to pass that on, you know, 100%.

How did you get involved with venture capital? Because I know that's something like myself, I eventually want to get into that industry and I like, wow. I learned a lot through you, just through your post and what you talk. Talk about. But how did that, you know, come into your life?

I love it, man. I mean, VC is super hot space. So I, I definitely. It's definitely sexy. I definitely get the alert. And, you know, I got into it because I had already been in business a little while, this and that, and had tried different things. But me and a few friends got. That's really all it is. It was me and a few friends got together and at first we were just like, man, let's put some. Some cash to work. And we didn't have a whole lot of money, but I could save up 3k and so could, you know, at that. At that time, I had four other partners. So all four of us saved up 3k a pop. And before you knew it, we put together 15 to 20,000 and we came up with a cool name at the time. Capital. Harlem Capital Partners. Short until Harlem Capital later, but. And the name could be whatever you want it to be, but you come up with a little name, you come up with a point of view. I'm going to invest in just esports, or I'm going to invest in cafes or whatever it was. And you invest that cash on behalf of this new entity that you created, Right. And voila, you've made your first angel investment. And what you'll find is, you know, you'll probably lose more money than you'll make when you start. But actually, the real thing to walk away from is the angel act of investing. So it was not the about. It's not about the amount of money. It's just like, even if it's small dollars, it's the act of looking for founders. Some founders will give you a really good feeling. Some will make you a little nervous. Yeah, some you'll like, but you won't like that business that they're working on.

Some.

And then you meet something where it's just like, man, this is a good fit. Let's give this a shot.

Yeah.

And you put cash in, and pretty much what you'll find is you fast forward that, and all of a sudden we were angel investors, and we were still, to us, we were just regular people, you know, putting our cash together. But then you start being seen that way, and then you start potentially being interested in, yo, can. Can I raise a fund and do this on a big scale? And anyway, man, that's. That's kind of how you get into. That's how I've gotten into anything that I've done.

Yeah.

Before I had a TV show, I had a podcast, and before the podcast, I had a vlog. And before the vlog, I was just doing iPhone videos.

Yep.

Before running a big VC fund, we were just investing our own, you know, and so I just really believe in finding the baby step version of what it is that you want to do and starting there and letting momentum run its course and get you bigger down the road.

I love that. That was the most simplistic, like, easy to understand version of starting a VC fund that I've ever heard, by the way. That's so tough. What's that pivoting point, like, when it goes. When it comes down to, hey, you know, you and a couple buddies, you start your own fund, but then you go raise a large round. Like, what is. What. What goes through your mind? What do you have to prepare for? Because it just completely changes the landscape of the business. So how did you guys adapt to raising a big fund? And what have you learned from that?

It does, man. And that's a great question, because there definitely is a tangible, tangible difference from when you're running it kind of lightly to when you decide, hey, I'm gonna do this.

Yep.

And, you know, when we decided, hey, we're gonna go for it, it actually ruptured the team a little bit because the team actually used to be a little bit bigger because it was a little bit of a lighter commitment. And so you could have people hang around. But when the core four partners, you know, we set course, new course, and we set a new pace for the intensity that we wanted to have. And that now it wasn't friction in the way that the rest of the team departed, but it was more so like, hey, we didn't sign up for this was how they were coming at it. And we understood, because you're making a mental commitment that this is going to be something new. And what that does is, man, renews the intensity, the time commitment, the focus, how much you think about It. All this stuff, man. In preparation of. We knew that we were going to go out and raise this big round. Well, it wasn't just like we decided we were going to raise a big round. So you start raising right away. Yeah, it was. It was actually more. We know we're going to raise a big round. Where do we got to be to. To where do we got to be so that when we go raise a round, it'll go well for us.

Yeah.

And so we committed to this. This planning phase, and I call it planning, only loosely, like we were plotting. We were still doing our deals, but now we had a new North Star and we packaged everything, we got smart around the industry. And then when we finally hit that point, we said, all right, you know what? It's. It's officially. It's time. Yeah. Just to give you, like, a tangible sense, we went to market with version 107 of our deck.

Wow.

Meaning we refined our pitch deck 107 times.

No way.

Yeah. Which. Which I wouldn't recommend for a startup because the startup is a smaller endeavor. So you probably go to market with V7, V15, V20.

Yeah.

But we were seeking to do something massive, so we refined, you know, a hell of a lot. And by then we had some initial people close to us that participated. At first.

Yep.

And then it was like, all right, we're still pretty far from our target. How are we going to go do it? And, you know, then there's a whole grind. That kind of. That. But. But to hit on your. Your ladder question, too, which was, hey, what did you learn from it? I learned a number of things. One is the way that you package the business says a lot about you as an operator. And I. It's not so much about the deck itself, let's say, if you're. Yeah. If we're, like, going to specifically speak on raising capital, it's not really about the deck. It's about the thought process that went behind crafting the materials. Right. And as an investor right now at Home Capital, we saw a thousand deals, literally a year. So you start to get really, you know, keen on who's got it or whatever.

Yep.

And you can usually tell when someone was 30, thoughtful around how they crafted it. You know, it's not about copying and pasting info and putting it together and copying the order that you saw online. Downloaded the template. Yeah, Yeah, I could see through that. It's more like I want to see how it is that you're thinking about how you're going to run your Biz, enter into the market, have your own angle. How are you going to go about pulling the right people together? Who do you even think are the right people to have on your team? All that kind of stuff will live in the deck. And, and so for me, first, second, and third is like craft. Get good at crafting decks because you're going to spend a lot of time behind them if you're going to raise cash.

I love that. That was very tangible, for sure. I want to change gears to the TV show, Right. Because you're. You're seeing a thousand deals a year, you're investing in different companies. How do you have time to be at a TV show? And how did that come into your life?

Man, the TV show was bizarre. I had someone reach out and Casey, I don't know if you're getting these opportunities. I'm sure that you are starting to get them if you're not already. Where people reach out and they're like, hey, you know, we had you in mind for whatever. And it's. It was just one of those things where some TV producer that never heard of from the west coast reached out. I had already went through something like that, and it was like a false start.

Yeah.

So I was already a little weary and. But she reached out to my friend Marcus Samuelson, whom runs the Red Rooster. He's a pretty well known restaurateur and celebrity chef and stuff.

Okay.

And so she had a mutual connection. So I heard her out and yeah, she's like, hey, look, LeBron James is doing an entrepreneur type of show that there were a couple of people, larger celebrities, that established the trend that culture was going to be infusing with entrepreneurship. It was 2015, 26, 2016, I would say. And so she said, hey, I want to do the same thing because I think we have room to sell a show here. However, instead of going and creating some game show type of thing, I want to root the show around someone whom is already active in this space and doing something meaningful. That time I was running co found Harlem and Incubator. And so she is a very seasoned TV exec from the West Coast. She produced Pimp My Rides to give you an example.

Yeah, yeah, yeah.

So she's got some cops. And so she sold me on that. And she. And she was like, look, come along for the ride. Give me your rights for one year and give me the right to go and pitch a show and hustle a show if nothing happens in the year. All good.

Yeah.

If it does, then you come along for the ride. So she did what's called TV packaging, which is you. You find junior talent, which is me and you, and you find senior talent, which is the big celebrity name. So she found Alicia Keys and Marcus Anderson, and then she created the concept. So that's the. That's the holy trinity there in tv.

Okay.

Yeah. The tight concept. Senior talent, junior talent. You. You come up with a show name and pretty much just, like, raising money for a startup. You go knock on doors. And then Vice was like, yo, this is kind of lit. We can put our own twist on it.

Yeah, yeah.

Before you knew it, they shot. They. They bought the pilot, so we shot a pilot, and then they had to commit to picking it up for season one, which they did. And it was a wild run, man. We were screened in eight countries internationally. Here. Germany, France, Israel, Canada, the States.

That's so crazy.

Billboards.

Yeah, I remember. I remember you posting all the billboards in New York. I was like, that is so dope, dude.

Dude. I'm just. I haven't thought about it a long time, but to drive down Times Square, like, see a billboard.

Oh, yeah.

I was having a bad day one day, and I was, like, late for a meeting. I was rushing to, and I caught the train, and I was there, like, grabbing the post, and I looked up, and there was a billboard of me on the. And I was like, bro, perspective, man. How can I be upset or mad at some. Something when, like, we're out here doing work, man? So that was a crazy ride, man. And for anyone interested in that kind of field, the number one thing I would say is blog, vlog, vlog, vlog, vlog. Because before Vice made the decision to back the show, their executives sat around the table, literally, and went through all my YouTube. Wow. Because they're like, okay, how is he on camera consistently? Is he natural? Is he. This is either. And that YouTube set the stage for a bigger platform down the road.

Wow. When did you start, like, putting out content? I know you talked about having a podcast, having a vlog, and we've talked about this before and the importance of that, but when did you start creating content, building a personal brand? Because I know when I first saw your content, everything you were doing, it just caught my attention. And you're really good at what you're doing on social and everything that's going on there, but where did that start?

Yeah, you know, that started for me. It started back in. I would say, when I was running my first business. I. I came across Gary, actually, Gary V. And I s. He taught me the importance of content in your business. It was at that time, it was less about personal brand. It was more about, like, yo, you gotta take content and work it into your biz. So that's when I started dabbling my toes after I sold that business. And then I kind of got into the incubator world. I started having a little bit more space to dabble, a little bit more. But even then, the scene was really young. Instagram was super young. Facebook was around. Twitter was more active then, for sure. And one thing you'll note is, like, the platforms constantly change. Every, like, five years, there's a new, like, Zeitgeist, something that just everyone's on, let's say. And I was out of that pocket. I would say I was making videos, but nothing was hitting. It was more so about just honing my delivery on the medium. Yep. Right. Because right now, when you turn on a mic case, when you turn it on, you still sound natural and normal because you've honed your delivery on the medium.

Absolutely.

Think about when we first started the mic in front of us, and you just start. You're like, oh, my God, I'm on camera. Hi, my name is Casey Adams. You know, but with reps, you get more ease and naturalness. So absolutely. That my first videos was around that. And then. Then there just came a time, man, when I just started getting it, and it takes like a year, maybe two, of, like, experimenting, and then it starts locking in, and then you start finding your own style, your own voice, your own subject matter that you feel comfortable speaking on. People start with it, and then people start sharing it, and you get one piece that kind of doesn't maybe go super crazy viral, but it goes a little bit more. Maybe for me, that first piece was, like, it got like 25,000 views or 30,000 views when I was normally getting a thousand. Yep, boom. I got this big spike. I was like, okay, I went away. My average went up to like 4 or 5,000 because you get a new influx of listeners and fans. And then one thing that really changed the game for me, too, was being a really avid speaker, like, going. There's nothing that can replace going and speaking to a room full of people and, like, connecting with them. Because then when they follow you on social, it's not like, oh, I kind of heard about this guy. It's like, yo, I remember that time when. And so I went and I spoke all across the country for one, two, three years, and my. My net just started getting bigger. By the time the TV show came. You know, it really locked me in, so.

Absolutely. That's so cool, man. And I wanted to also, you know, address, you know, a mutual relationship of ours. Cause I know a lot of young entrepreneurs listen to the show, and you're talking about raising money and TV show. They're like, okay, he's crushing the game. Where did this start? And I do want to. We're recording this podcast on an app called Modi, which Hugo Sanchez and the whole Modi team, they created something amazing. And. And I know that Hugo was a mentor in your life. When he first told me the story, I was like, that is so incredible. So I'd love for you to just dive into for a little bit how you got started in everything you were doing. Because your story is incredible how one person or one situation can just change your perspective on how you're going to build your life.

Yeah, man, I'm glad you brought that up. And shout out to Hugo, man, who's dear brother to me. And, you know, I actually had in mind to. To lead and open up with our mutual connection, friend and mentor, Hugo, because that is the glue here. And then I just forgotten the heat in the moment. But yeah, man, it's super bizarre. We have an interesting touch point that. That connects us because. Yeah, well, before I was in business or any of this stuff. And you know what, thanks for putting a finger on that, because I don't. I don't realize how, like, TV show and all this, the stuff that I'm doing now sounds far ahead compared to, like, when we started, let's say.

Yeah.

But, yeah, it's good to be in touch with those roots, man. I was the doorman. I was working behind a desk. A regular job. I was going to school at 18 years old. Yeah, you know, hungry, hungry. I wanted to make anything work, man, no matter what it was. And, yeah, I met this brother whom, um, he parked in the building where I worked, and he lives right across the way, and he ran a chain of dry cleaners. And I just remember the thing that stood out go. Was not the whip and the ice that he definitely had. It was. It was more how he made people feel. And the other door, mind you, I was new in this building, right? And I'm going, and I'm clocking in and I'm learning the building. It was a massive building, by the way. It's 337 units. Really, really big building. And so it's very intimidating. You're clocking in and you're put in the middle of this enormous lobby. There's people in and out. You kind of got to know what to do, who to read that.

Yeah.

It's a pretty high stakes, I would say, kind of job. But the doorman would say, okay, this. This guy is this way. You know, this is. This person. Kind of fill you in. That's the owner. You know, he hates when you do whatever.

Yeah, yeah.

And then Hugo would pop up on the scene, and people would be like, yo, that's. Hugo was good. Really race. And like, they're like, yo, that's our dude, man. He does all the drag cleaning for everyone. You always recommend them. I was like, okay, bet. And I carry that torch because he made me feel that way. Fast forward, though.

Yeah.

He was just really passionate about helping me see more for myself than I saw for myself. And even at that time, I. I knew I had grand vision. I didn't have a manifestation of that vision. I just knew I wanted something. I knew something big was in store for me and that I wanted something big in store for me. And I met a guy who believed that something big was in store for me.

Yeah.

And whom did. He offered me the. A path that he had available to him.

Yep.

Right. If Hugo was in. Was a Wall street trader, he would have got me into stocks. He was a video editor. He would have got me into that.

Yeah.

But what he had available to him was building businesses. And at that time, like, a big laundromat enterprise. And he would pick me up after my shift. We would ride around in his M5 Beamer, and like, we would just. I would make runs with him.

Yeah.

See what it was like all my days off, I would go and chill with Hugo. Yeah. Right. Around with him and. And make him see, you know, see him do his thing. So, anyway, point is. Yeah, man, it was enough. Not because of. It wasn't an industry that I fell in love with the other market or anything technical. What I fell in love with was how Hugo was able to maintain his. His sense of self and independence.

Yeah.

Like, bro, we were. We were in a pretty affluent area, and there are a lot of people that live a pretty buttoned up life in exchange for the type of life that it can afford you.

Totally.

And here I saw someone that was still like, yo, the law. Yeah. Still so himself. And he was really getting it.

Yeah.

And it made me feel like, yo, I want to be like this. And so I stepped into that world and, you know, over time, I found my own version of what that means.

Totally.

I'm forever Deeply grateful to Hugo for that. And I think it's just bizarre that we share that connection.

I know.

100, man, it's so tight. And when he first told me that story, too, because I was. I followed you, and I was learning about your story, and then Hugo told me that I was like, the world is so small. Like, what?

But.

But I think I want to say this. To say this. And it's like, you know, all it takes is one person or one conversation to change your complete perspective. And I'd love for you to touch on, you know, the importance of mentorship along your journey, whether that comes to raising capital and talking to experienced VCs or whatever it is.

Just.

How have mentors played a role in your journey?

Yeah, it's a great question, man. And you're right. You know, mentorship has played an important role in my life. I've had a nuanced, interesting, nuanced relationship with mentorship, where at first it took someone to get me to give me a blueprint, like Hugo. And then one thing that happened for me is it got really convenient to always hit up your mentor when you're tough, when you're faced with a tough decision, you know, because you don't yet have that confidence in yourself to execute it. And so it's, you know, it's really great to have someone to, like, counsel you. However, it does turn into a crutch at some point. Where it did for me, where, like, I started, I started realizing that anytime I had a decision, I was calling my mentor, and kind of. I then realized I was outsourcing my ability to make decisions, and it wasn't about being right or wrong so much as it was about nurturing your ability to make the call. Even if it's wrong or right. It's just, you got to make the call. Yeah. So I swung the opposite end of the spectrum, where then I went completely away from mentorship, and I was like, I got to hone my own gut, my own ability to make decisions and so forth. And so it's been this swinging pendulum the whole time because, yeah, when I hit a new level, you know, I find myself, you know, looking to bring in someone whom, you know, can show me the ropes, you know, at a. On a different industry or whatever the case is. So, yeah, man, it's important to anyone young out there, though. Here, listen to me on this. Don't go out there, like, proactively looking for a mentor and, like, asking, yeah, you want to be my mentor? Because that, to me, is not authentic. For me.

Yep.

When you walk the path, you meet the mentors along the way.

Yep.

Because not everyone is out there anyway putting out all their business. And, like, you know, certain people might see me, might see you, might see Gerard Adams or whatever as mentors, but we're in this space of, like, broadcasting, you know?

Yeah.

There are so many real ones that don't say shit.

Absolutely.

You know, are got way more chops than us.

Yeah.

And you meet them when you're on the path.

Yep.

So for me, locking on the work. And by the way, what makes someone want to mentor you anyway is when they see someone who is growing and putting in the effort, and it's not right all the time, but they're really giving it an honest shot. And that's what made, you know, my relationship with you go special. And then later on, I had another mentor, Tomazo, and another mentor, Ming, who each taught me very different things about myself. But the common through line was I was always actually doing stuff, and they always actually wanted to help. And another thing is don't accept any mentors who charge you. Any mentor who charges you is full of shit. They are selling you a dream because the real ones, they give the game away like nothing because they're confident in their own value.

I love that.

That was powerful, man. For sure. Last question before we wrap up, and it being number one, tomorrow's my birthday. I'm turning 20 years old, and I want to ask you. 20?

You turned 20 years?

How did you think I was? Wait, how did you think I was?

That literally took me a moment to process. I was like. I was waiting for you to finish that. Like, 20. What? Oh, my God.

Crazy.

I mean, I knew you're young, and I like, I know you told me your age before, but that fades away with time. And then I just thought you were, like, 23, 24 or something like that. But damn, I love it.

I appreciate it.

Happy birthday.

I appreciate it. I mean, the question I want to end with is, you know, if you could go back to being 20 years old with all the lessons that you've learned through raising capital through selling your business, what would you tell your younger self? Based on what you've learned so far?

I would say, hey, man, you're gonna get swing big, and you're gonna get wrecked for swinging big. You're gonna get less wrecked than someone who swung small. You're gonna want to abandon the big things that you're going after, because medium or even small is happening faster for more people. But swing big my friend. Because all you got to do is stay at it long enough and then it starts coming your way and it starts absolutely changing your life. And then the life of more importantly, the people that are going to be tuning into what you're doing, following along your family, your community.

Community.

And you could really make something special happen if you just swing big. So that's my advice to me still. And that's my advice to me earlier as a way to encourage myself to keep going because there definitely have been some times where it's been hard as man. And I'm just glad that I never. That I never gave up on it.

I love that. Well, John, I just want to say I appreciate the time today, man. Where's the best place for people to stay in touch with everything you got going on?

Hit me on the gram. Guys, I would. I would say hit me on Tick Tock, but it looks like Trump is.

Shutting that dude I saw.

So. So hit me on the gram. I'm at John Henry style. Hit me. You can also text me.

My.

My style is in the bio. And yeah, man. Yo, Case, big up to you, man. You've been blowing up, you know, bright, bright, bright future ahead of you. So I'm optimizing. Great community venture growing. So guys, thank you for having me.

Appreciate it.

Rise of the Young.

Monarch Legacy of Monsters An Apple Original Series the world is on fire. I decided to do something about it on November 17th. This place, it's not ours. Believe me, the most massive event of the year arrives. If you come with me, you'll know everything. I promise. Monarch Legacy of monsters streaming November 17th only on Apple TV.

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