A conversation worth having: John Henry!

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Ja'dan:
This is Conversations Worth Having, a weekly podcast exploring transformative ideas about how we live, work, and play hosted by entrepreneur and designer Ja'dan Johnson.

Ja'dan:
Yes, yes, yes. This is conversation worth having. And I'm your host, Ja'dan Johnson. I'm really excited to announce my special guest joining me on the show today, none other than entrepreneur, investor and TV personality John Henry. Hey, John, how's it going?

John:
Hey, man. Well, it's great to be back with you. I went to Jamaica for the first time through you and second time through you. So I have a real can say at this point connection with you and the community back home there and have made some long, long standing friends, by the way, from from our trip together.

John:
So I was always inspired by, um, your ability to foster community. So, yeah. So it's good. Good to be catching up and. Yeah, man, I mean, oh my gosh, so much has happened. But in reality, none of those business accomplishments feel super important in the wake of, like, all the stuff that's going on. Um, I think the most important thing for me is, OK, I'm twenty seven now. I started being an entrepreneur. I was 18. So over the past damn near decade now. Wow. It's crazy to even reflect on during that time.

John:
I realize that your first decade in any endeavor is really spent getting to know yourself, getting to know um, you know, what your real appetite for risk is.

John:
What, what are some of the properties that you like taken on? What are some things that you thought you like doing until you started doing it and then realized you didn't like doing it? What are you. And it really it runs the gamut. This game is all about building those initial skills, um, getting to know some friends that you'll be doing this with for a while and getting to know how it is that you want to express yourself and tackle some of, um, you know, some of the bigger problems we're tackling. And yeah. So that's how I feel at the top of this decade. I am now finally just starting to feel like, wow, OK, cool. I feel like I know myself, I feel like I'm more capable than ever. I have more resources than ever. More network, more know how I'm more perceptive. The world is at a time where it needs people like us thinking boldly and daring greatly also more than ever.

Ja'dan:
Well, John, I really love how you've brought it into perspective. And I feel like a challenging part to vote. You know, getting to know ourselves is dealing with uncertainty and covid has really risen for so many different people. So I'm curious how you have personally been dealing with some of the uncertainties today?

Ja'dan:
Um, well, I've been actually in a strong position during this pandemic, and it's one of those things where I'm reflecting on that, um, as well, because, you know, in times of great misfortune for the world to be fortunate, to find yourself in a good position, I think like that that comes with a certain responsibility that you you know, that I've tasked myself with where it's like, OK, you know, the economy has been so vastly different for different people, you know, and there are people, including in my immediate family, that are going through a much, much harder time. And the reality that there are two economies is more apparent than ever. You know, there's the creative class where we can get paid. Younger folks like you and I, um, can get paid to create things online that are valuable to folks. And, you know, that's a blessing that we have from being digitally native. And then, you know, there's a whole other generation, um, and it's not even just an age thing is also a geography thing. You know, there are economies that are more blue collar. Um, and, you know, just observing the differences between the two has made me feel like, OK, we got to step up and. And see if we can try our hand at improving the situation for others.

Ja'dan:
Yeah, and I mean, before we even get to the weeds of just like talking business and just your experience as an entrepreneur, there's this mindset, you know, you said a word noticing and noticing. It's just such a critical skill for entrepreneurs. And it brings us to this concept of just mindfulness and how are we managing to be mindful or at peace mentally while juggling the uncertainties in the world, managing our businesses, managing relationships as an entrepreneur. How do you create how do you create that space for mental tranquility?

Ja'dan:
Well, I think, you know, if there's anything that this pandemic has created space for is a little bit more tranquility, also more chaos. So it's funny because the extremes, the pendulum has moved to both extremes almost at once, seemingly, where it's like, OK, there's certainly more chaos. Businesses are forced to be closed. People are forced to be at home.

John:
People are sick and dying. But then also on the opposite extreme, you have a bunch of people that are home more often able to spend time with their family, more often able to spend more time reflecting. There is less mindless going out. Right. So, like, so Flomo is gone because where the hell are you? There ain't no place to be anyway. And and I've felt the collective you can almost feel the collective energy of what happens to a society that is so consumer driven and so driven on. I got to be here. I got to be there. Well, all of that has been silenced at once for everyone.

Ja'dan:
And it has created a fascinating period of collective reflection, and I am a firm believer that there are a lot of great things being brewed up right this moment from newcomers, from more experienced entrepreneurs, from creators in the media, in politics and on both sides of the spectrum.

Ja'dan:
Mind you, it just it feels like it feels like we will remember this year and the things that will come from, what, this year? Yeah.

Ja'dan:
Know that's such a.

Ja'dan:
And it's such a critical way to to look at it as we I feel like as everybody is flowing between those two pendulums.

Ja'dan:
It's almost like living the ego to the chaos. And then you have to create that space for finding peace. And just like so many people are confused, because never before have we been, like, forced to just stay inside our homes. We have to deal with the realities of our problems are way more than we're used to.

Ja'dan:
Plus, also, it creates this beautiful thing that you've talked about, which is this opportunity for people to step up and turn their skills into things that are useful, right. To start businesses.

Ja'dan:
And I've realized a lot more a lot more people have realized that they can be entrepreneurial or have found some balance where they can have a job, but also pursue their own entrepreneurial pursuits. So tell me, what have you been like seeing from your crowd at this time when you have personally use some of this opportunity to create a space to connect with different entrepreneurs one on one, and offer feedback and insights? So as you're going through this process, what are some of the things that you've been learning?

Ja'dan:
Yeah, no, I think I think that's right. Um, and. You know, I guess.

Ja'dan:
Also to people's interests, I'm a big fan, and as I've connected with. So I'm going to start over here and say so, yes, 100 percent.

Ja'dan:
I've been I've been I created an offering to connect with people 30 minutes at a time that is now largely done. But it served me well during the pandemic time while we were just at home anyway. And I figured, man, why don't I just create something where I can speak to people directly? And it's something that, you know, doesn't make sense because you can't scale it. And, you know, my some of my immediate peers argued that, hey, there's way better, more scalable applications that your time, given the skill sets that I've developed over the years, i.e. raising a fund and all that is stuff that you can scale. But sometimes the magic comes from things that you can't scale, like having a really focused conversation, one on one with two hundred plus people back to back to back to back to back. You know, man, you especially at a time like this, you really tap into and start getting a feel for where people are at and consistently across the board, you know, even outside of business, you know, businesses is kind of where my outlet is and a lot of my audience. But it's also a great time for art. It's also a great time for music. It's also a great time for organizing socially and politically.

Ja'dan:
It's a great time for any respective outlet that you feel your heart calls you to. Man, it's a great time to just start unearthing that a little bit. And look, the one thing to note is like the people that are experiencing the biggest lift in this pandemic are the people that put in the groundwork over the last two, three, four, five, six, seven, eight, nine years, because that's how long it takes, you know. And so so anyway, I don't know my perspective now as I'm speaking to so many people that really want to get started on their journey. And, um, for me. There is no better time to to kind of jump in because people are being laid off, you know, you can now do it from home. So all all these reasons to say, hey, you know what? Let me let me pick up the guitar again. You know what? Um, let me, uh, pick up my passion again for crocheting. You know, let me start gardening again. Um, let me, you know, do my painting and, you know, let let me offer bookkeeping services for small businesses. I've always wanted to do that. Um, you know what? Maybe I should start a little LinkedIn show, um, you know, all those kinds of musings like that that, you know, when society is turned on, those things can feel like trivial. But when society when we press the off button like we have for better, for worse, it creates space for you to say, you know what, maybe these little curiosities that I have planted in me is actually the way that will yield, um, you know, a career for myself that I feel really fulfilled doing so.

Ja'dan:
Anyway, that's the sense that I get. Um, that's definitely the sense that I get.

Ja'dan:
Yeah, and I mean, huge, huge props to you, because as a person I've known, you've always given these opportunities for people like this, regardless of what level they are, you always open these spaces for them. I think that's even the foundation of the work you started beyond your first venture. You know, with the things you're doing with Harlem Capital, you just consistently been delivering value. And oftentimes you're probably not asking for for much, are you? For what it's worth in exchange. But you just like consistently you're just like providing, providing and providing value. And if we take it back. Yeah. If we if we take it back to like, you know, those initial days with the work you're doing with Cofound Harlem and Harlem Capital and just kind of looking at the current landscape and a lot of the conversation on, you know, we need a lot more people of color in different places and in different spaces on the lack of certain diversity and representation of of certain communities in black or tech ecosystem and in our venture capital space.

Ja'dan:
You know, how are you personally feeling about the.

Ja'dan:
Because I want to acknowledge that there has been progress and progress has been made through people like you who have been committed to supporting entrepreneurs of color, to supporting women of color and amplifying those voices within the communities. So I, I don't I'm not interested in going down that road of only seen the problems because people like you are problem solvers and you guys have done the work.

Ja'dan:
Yeah. Yeah, no, absolutely. And I, I accept those very timely man. Thank you. Um yeah.

Ja'dan:
I mean look. Absolutely. The interesting thing is. It's been hard work over the last decade to roll our sleeves up and work on companies first, first, first step was just working on something that got me out of work in a job and also help unearth some of my initial skills and learn how to sew. So it's it's been a process, but and that's really what I admire about this whole thing. It's like, OK. It was a gradual process where whereby first you you develop your own behavior to go for something, you know, you go through some of the ups and downs that comes with that, then you start kind of meeting some interesting people that become friends and become peers. Then the word spreads a little bit about what you've been doing and then you get braver and take on things that are a little bit less certain. And then you start finding, wow, this energizes more people. There's something under there's an underlying spirit to that that lies with projects that are meaningful to people. It unlocks more people's hearts. It gets more people involved, you know, similar to like you, you definitely experience that building community in Jamaica when you do something that's close to people's heart, you know, people take you in in a bit of a different way.

Ja'dan:
So that just gradually grown and then you find friends that, you know, it's not just enough to kind of have friends that you love and respect and cherish. But then you start realizing, like, OK, you need a certain type of friend, like you need a friend that you're also close to and then also is just as committed. And and then on top of that, then the timing has to align between all your individual lives and for you to create space and say, OK, let's try this thing. And that's what Highland Capital was. And then taking that from maybe we could do this, you know, to start by investing our own cash and then eventually saying, you know what, let's go out there and raise a fund and, you know, dream big. And you kind of have a super successful outcome for us with our fund one hitting forty million dollars and managing all that capital and really making meaningful investments up to upwards of a million bucks in each company at a time.

Ja'dan:
So so it's really trippy for me to even sit here and say that I've raised the 40 million dollar fund because when I start, like when I started, I was it was a 17 dollar transaction at a dry cleaner, you know, than by the way, I didn't even own the dry cleaner. I was picking up your clothes on the subway and taking it to a dry cleaner and having them charge me the cheap rate. And I would go and charge you the market rate. Like, that's where that's that's where all this has started for me.

Ja'dan:
And it wasn't mapped out and it wasn't intentional and it wasn't strategic. And it wasn't because I, you know, went to networking events and or got a degree or anything.

Ja'dan:
So it was really at the root of it all was, man, let me continue following that.

Ja'dan:
You know, the things that naturally excite me and light me up, even though it may feel counterintuitive to do, even though, you know, there's not an immediate path to financial viability. And things would certainly be less stressful if I just had a regular job or occupation, even though all those regular life things, you know, are adverse to following that little thrill inside you.

Ja'dan:
I've found that the more you lean into that, it actually their vessels for your curiosity and you start to unearth bigger and bigger problems. And, you know, it takes you down some interesting roadman and you end up being in a room that you never thought you'd be in. And then it starts coming together for you. You know, after the initial shock of like, oh, shit, I'm actually in these positions, wears off, then you kind of grow into it. And that's where I am now. My career in my now first year of my late twenties, I would say I'm twenty seven now stepping in this.

Ja'dan:
See, I'm really starting to claim that power and say, OK, you know, I know now I'm capable of big things. I know now it can't be done alone. I also know now that I can play a Big Brother role to, you know, to some of the cats just starting out.

Ja'dan:
And I also know that, you know, I'm just brave enough to think about doing things that are scary as hell. And, like, I feel daunted all over again and like a beginner all over again. So it's kind of funny how it's a full circle moment and in a weird way like that to that make sense.

Ja'dan:
And, you know, taking taking that step back from where you are now and just like thinking back then, what are some of the skills that you would definitely invest a lot more? Or you just recommend people invest energy and time into. To help eventually get them to a place where they can feel successful.

Ja'dan:
Yeah, I think the most important skill is, um, is learning how to tune out other people and other voices. I know that sounds weird. I know people will probably say, hey, learn how to sell, learn how to code. I think if you're going to go in is down this entrepreneurship path, it is about being able to radically listen to yourself. And, um. And hone your judgment. That's not to say that's not to say be deaf to the world around you in the input of others. Um. That's more to say. See, it's almost like you. The musings that you have and the things that capture your imagination are there now, but lay quietly suppressed. But every once in a while, you have an inkling around like and that really lights you up and this game is really about nurturing the bravery to follow that inkling that lights you up. It is far less about hard skills.

Ja'dan:
It is because at the end of in any industry, at the you know, at the other end of art is someone who consumes the art and interprets the hour. At the end of the other opposite end of music is someone who listens at the opposite end of a of a service is someone that experiences it. A customer at the you know, it's it's really just a human game. And I think so many people disproportionately spend time on the science. But they don't realize it's an art, you know, it's the art of laying yourself bare and expressing yourself more and more fully and unlocking people's hearts in whatever direction you feel is.

Ja'dan:
You know, it would make the world a better place. So anyway, you know, I know that these are not super concrete. Um, I'm aware, but I just I feel like people on, you know, I haven't done one of these in a while. And it.

Ja'dan:
You know, it just feels like people will naturally crave and want to hear, hey, get good at LinkedIn growth hacking because, you know, learning how to, you know, get your reach up five percent each day is going to yield one hundred percent increase in 20 days. And yes, that stuff is there. It's true, I guess. But for me.

Ja'dan:
I resisted the temptation to worry about any of that stuff for four years and focused instead on nurturing my journey and my authenticity and journey and like all that stuff that I mentioned, and then the interesting byproduct is then you resonate, then you grow, then you unlock partnerships, then people approach you about new things to uncover.

Ja'dan:
Then, you know, Alicia Keys reached out to me and said, wow, you know, we love all the stuff that you're doing. Let's let's explore show on Vice. Then you get all the stuff that people mistakenly, you know, try to reverse engineer like it's a math problem, but it's more a matter of, you know, nurturing a big heart and nurturing big bravery.

Ja'dan:
And people fall in love with those things. And you start going for things that other people aren't going for. And then people fall in love with that do it and and you know what I mean?

Ja'dan:
So if there's anything I can impart to anyone listening, it is that this game is far less about science and tactics and math like like blogs would have you believe.

Ja'dan:
And it's a way more about, you know, intention and nurturing your curiosity and going big and having a crazy imagination and also being self-aware enough to know that you have to find a vessel to express the culmination of all those curiosities that you have. So all those curiosities, all those musings, all the excitement, you find a vessel and then through that vessel, you express that and focusing on the purity of that unlocks so much opportunity down the road.

Ja'dan:
It's easy for us to jump into this world of, oh, well, here are 10 things you need to work on, and I completely agree with you that an essential skill to right to develop is listening to your voice. It sounds fluffy, but it's not there is not been a single time through my own journey as an entrepreneur where trusting my gut or trusting my instincts has not given me the courage to deal with the result that that choice created. And like a mentor once shared with me, you know, he's saying, what's your your gut is basically the sum total of your lived experiences and people would always like. It's crazy how many times I've reached out for advice and then checking those advice with my gut. And they're saying two different things. And it's a hard thing to decide which which direction to follow. So, you know, if maybe we're going to talk tips on trick, then maybe I'd love to hear how is it that you decide when something you know, when is it a gut decision versus this is a time for me to reach out to somebody who is just a little bit more experienced, then that might bring a valuable perspective through which I can then use to make a decision.

Ja'dan:
Yeah, no, that's a good question. And I get that one a lot. And I my take on that is having a mentor is important.

Ja'dan:
And it alludes to what I was saying earlier. I think the most important skill is learning to make your own decisions because it is helpful to have a mentor and to have outside counsel especially. Something is really super high stakes. But what I found myself doing was I realized every time I had a hard decision, I was calling a mentor and then I realized, oh, I'm outsourcing my ability to make a hard decision, because every time I had one, I was calling a mentor because I was I knew I was more likely to be correct if I had someone more experienced guiding me. Right. So, so but then what happens, you know, you don't realize it, but what happens eventually is you are not nurturing your ability to make decisions because you're scared of being incorrect. And that was what I told myself. I was like, oh, shit, I'm scared to be wrong. And then I realized, man, it's not about being right or wrong. It's about the person you become when you dig deep and make the decision. You know, at first you're going to be wrong more often than you're right. But to nurture is the bravery of making a decision in a high stakes moment on your own. It is scary. You will be correct more often if you had better counsel. But what will happen is eventually, over time, you you know, it's just like any algorithm, the algorithm gets smarter with more volume.

Ja'dan:
Right. Facebook learned what you like when it saw you interact with more photos and more people and more things and more industries and more content in general. So we work the same way. The more decisions we make, we're wrong. We're wrong. We're wrong. We're right, OK? And then, you know, it's just it's more input into your model. You're, you know, if you will and I hate to look at it in those terms, but sometimes sometimes analogies like that will help some help a nugget sink in. We need more volume and repetition and repetition and input and more frequency. And then you start nurturing your gut. Right. So so, you know, to your question, hey, when do we know to go for the gut or to go with the mentor? For me personally, you're going to be correct more often if you use the mentor every time, but you will then never outgrow that mentor. You have the same mentor forever. You'll stay at the same stage forever. The more willing you are to be wrong, the more willing you are to grow. That's a deep insight, I've never had that exact series of thought. The more willing you are to be wrong, the more opportunity you are making for yourself to grow. Um.

Ja'dan:
And so anyway, that's kind of how I view that's how I view it, yep. No, I'm with you.

Ja'dan:
Ten, ten thousand percent just to tighten all up. If you are looking for what skill is the perfect skill to work on, you know, you're in college is your first time starting a business venture. It's not like this is your playground to hone your voice and to hone your gut and trusting your instincts. Yeah. And then you can outsource that eventually.

Ja'dan:
And yeah.

Ja'dan:
And then there's the kind of was conversation, you know, I couldn't pull you on a slide and not talk about building wealth. Yeah, like it's it's it's the it's the the you look at our conversation, you're going from here. This is the perfect time to start a business. This is the first time to turn the thing you're passionate about into into a viable trade to you know, this is a time to listen to your gut and to make some decisions. But one thing is hard is that once we once we get into the game, the and the money feels nice. A lot of us don't know how to truly make our money work for us.

Ja'dan:
The the instant gratification is just like it's so good that we never truly put our money to work for us and then we end up becoming a slave to our own craft for a very long time.

Ja'dan:
Yeah, no, I resonate with that. And, you know, the truth of the matter is, too, it takes it takes enough.

Ja'dan:
It takes enough, you know, you're right, you are locked in this kind of a grind for a long time and hopefully, though, hopefully at the very least, for me, the greatest wish I have for others is if you have to spend your time and energy making a living, then at the very least, let's make it something we love to do, because I really, honestly believe any time I come across a lot of people that are unhappy, you know, for a big chunk of those people, it's because, like, they they they hate doing what they do for a living. I couldn't be happy if I spent most of my life doing something I didn't like doing that would suck, you know, but then then you did. So let's just say for a moment people were listening, OK, you know what? I'm going to go after my passion. And then you make the the unquantifiable leap, honestly, in terms of quality of life. You might be like you might be making less, but you'll be more fulfilled. Now you're doing something you love. Then it'll probably take five, six, seven years building your skills here and your earning power. And before you start to realize, you know, oh, wow, OK, let me see. You know, like I love this Grine and this, you know, this journey.

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