How To Refine Your Thinking With Tremain Davis

What is the value of learning, and do we ever stop? In this episode, guest Tremain Davis of Davis and Davis Investments and Management joins us to talk about shifting his mindset through constant learning. He joins Gary Schoeniger to share how he did not have an easy start in life. Raised by a single mom in an underserved community, the only entrepreneurs he knew were illegal ones. Yet, from an early age, he knew he wanted more. Tremain shares how building an underground candy operation as a kid inspired him to pursue entrepreneurship on a higher level, constantly refining his strategies and building on his knowledge. They also discuss transforming yourself into a powerful optimist, maximizing current technology for nonstop learning, and managing security risks when aiming for bigger life goals.

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How To Refine Your Thinking With Tremain Davis

I’m speaking with Tremain Davis, who’s the Founder and CEO of Davis and Davis Investments and Management, a Maryland-based boutique strategy consulting firm. Like many of the entrepreneurs I’ve interviewed, Tremain did not have an easy start in life. He was raised by a single mom in an underserved community. The only entrepreneurs he knew were illegal, yet from an early age, he knew he wanted more. Like many of the entrepreneurs I’ve interviewed, he was an average student. As Tremain himself put it, “It’s not that I’m not smart, it’s that school wasn’t my thing.”

Yet, while he managed to secure a full-ride basketball scholarship, he ultimately dropped out of college to pursue his entrepreneurial dreams. In this episode, we cover a wide range of topics, including how at the age of fourteen, an undercover candy business shifted its mindset as an up-and-coming entrepreneur. We also discussed the importance of lifelong learning, the power of ideas and taking responsibility when things don’t go as planned. Without any further ado, I hope you enjoy my conversation with Tremain Davis.

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Tremain, we met on Zoom. We were introduced by my colleague, Rob Hern. He met you at an entrepreneurship symposium or an entrepreneurship event at Bowie State. Are you an entrepreneur in residence at Bowie State or something? What are you doing at Bowie State?

I had run their incubator program. They had a summer launch and the student undergrad research initiative. I ran that for Bowie State. What I met Rob at was the culmination of the nine weeks with the student cohort. These were all student entrepreneurs who were starting some incredible businesses. They had a pitch at the end. They were able to win money and all of that. Rob came in as one of our guest judges.

The first question I want to ask you is, how did you get on the entrepreneur path? The way that I think about this is did you jump in the pool? Did you fall backwards into the pool? Did you wade into the pool? Did somebody shove you in the pool?

I probably fell backwards in. It is more of a necessity type of thing. The quintessential story is I grew up in a single-mom, underserved, under-resourced community. Nobody in my community was an entrepreneur except those that were doing illegal entrepreneurial activities, not anything I wanted to participate in. I don’t know how I knew but I knew there was something more than what I could see. I didn’t know how I was going to get there and get out of that community. I didn’t know any of that stuff but I did know that there was more. What opened my eyes to entrepreneurship is I had my first visit in eighth grade. I’m talking about me and my mother.

We led a fundraiser for our class where we wanted to go on a trip. We raised all of this money. The people that we did the company fundraiser with were excited about us doing this fundraiser. They sent all this candy to the house. They said, “Thank you for doing this fundraiser.” I get home from school and there are boxes and boxes of candy sitting at the front door. I don’t even know it’s coming. I called the number on the box and it says, “We wanted to send you guys something to thank you for doing this fundraiser.”

I take it into the house, put it in my closet in my bedroom. My mother doesn’t even know I have this candy. I go to a strict private Christian school at this time. They don’t allow candy in the school. I’ve got a whole closet full of candy. I try to eat some of the candy. I realized quickly that I’m not going to be able to eat all this candy on my own. I said, “Let me go and take some of the candy to the school. I’ll sell it for $0.25 a bag.” I took a few of them. It’s sold out instantly. I was like, “What’s going on here?” No candy is allowed in the school. Let me reiterate that.

This is a strict privacy school in the early ‘90s. The headmaster of the school will still hit your hand with a ruler. It was old school. I said, “I’m going to bring this candy in.” I started bringing candy into the school and selling it to all of the students. I became this underground candy baron. I had a serious underground operation. I’m doing hand-to-hand transactions at the water fountain. This became a serious thing.

You guys are doing it all on the down low.

Nobody knows who this candy is. I’ll tell you how bad it became. The lady that runs the whole school, the principal, calls a big assembly in the gym. She comes up on the stage with my candy wrapper and says, “Somebody’s bringing candy into this school. If we find out who you are, you’re going to be suspended.” I’m like, “What am I doing here?” Everybody on the ground, the kids, know who it is. I’m being cool. I don’t say anything. I don’t get excited or anything like that. I play it cool. I’m a rockstar.

All the kids want to do things that you’re not supposed to do. My business explodes the next day after I get threatened with a suspension. This goes on for months. I started with a few bags in my locker. After a few months of this, I’ve got enough candy in my locker to get life at this point. This is a big turning point for me. One of the teachers comes to me and says, “Stay after class.” We get out of class. He brings me in and says, “I know it’s you selling the candy. Don’t try to argue. I know it’s you.”

At this point, I don’t show it but I’m shaking in my boots, “I’m going to get suspended. What I’m going to tell my mother?” This is in the ‘90s so this is a lot of money at the time. He says, “You’re probably doing about $200 a week because all the kids are eating your candy. Give me $20 a week. That’ll cover gas and lunch for me for the week and I won’t say anything.” I said, “Deal.” I got shut down. I’m giving him $20 a week. I’ve got a teacher on the payroll now.

Another month goes by, school’s almost over. Another teacher calls me in and says, “I figured it out. I know you’re the one selling the candy.” I go into that meeting and say, “I’ll give you $20 a week. That’ll cover your gas and your lunch. You can be a partner with me on this.” I say that to the second teacher going into the meeting. I’m confident at this point. I don’t know what he is going to say. I’m thinking, “Let me try my hand because it worked with the first teacher.” Guess what the second teacher says? He goes, “Make it $25 and you got a deal.”

You’re in 8th grade, 14 years old.

13, 14 years old. For the whole back half of the year, I ran an underground candy organization. I had 2 friends and 2 teachers on the payroll.

How did that end? Did you eventually sell the candy out?

That’s exactly what happened. I got to the bottom of the barrel and ended up selling all the candy that the company gave me for free. It was 100% profit. All things that I know now but back then, I’m like, “If I’m getting the candy for free and selling it for all this money, then I can keep all of the money.” This is my rationale as an eighth grader. I didn’t know that I was doing a serious entrepreneurial business thought process at the time. Next thing you know, it’s growing. I don’t have enough room in my locker. I’ve got to hire a friend of mine to put candy in his locker. I’ve got kids on the payroll. The two teachers, I’ve got them on payroll and then the end of the school year.

What that taught me is I don’t want to work for anybody. My rationale at the time was like, “These guys are talking about the teachers. They went to school. They’ve got degrees and everything like that and I can buy them off for $20 a week.” My rationale at that point is jobs are for suckers. I’m like, “I don’t want to have to work a job. I don’t even know if I want to go to college. Why would I want to do that?”

That started the thought process of, “I want to somehow get into this business stuff. I don’t know what it means.” Entrepreneurialism, in the ‘90s, wasn’t a word. It’s a buzzword now and everybody puts it on social media. They’re grinding. They’re an entrepreneur. That wasn’t a thing back then. I didn’t even know how to quantify what it is I was thinking in my mind. That was my first iteration at business and set me on that thought process of me always wanting to do my own thing.

Entrepreneurialism wasn't a word. But nowadays, social media has turned it into a buzzword. Click To Tweet

Let me unpack that for a second. I want to go back to something you said about growing up, I forgot how you described it exactly but you said single mom and at-risk and underserved community. You said something that struck me. “I thought there was a better life out there. I couldn’t see it.” I have an entrepreneur friend of mine that told me the same thing. He grew up in the Bronx, 1 of 11 kids and was a single mom. He said the same words. He said, “I knew there was a different life out there. I didn’t want to be a gang banger or a drug addict. I wanted a better life. I couldn’t see it.”

That’s an important piece of the puzzle that I don’t want us to skip over. There’s something in your brain that’s landing like, “My circumstances don’t necessarily determine.” Let me put it to you differently. I interviewed this guy named John Osher once. He’s the guy that produced the Jersey Boys. He’s a serial entrepreneur though. He created this $5 spin brush and sold it for $475 million 15 months after he started it.

Do you know what he said to me? He said, “I could answer any question about entrepreneurship with the same three words, find a way.” As a little kid, that kind of idea seemed to land in your brain for whatever reason like, “I got to find a way.” The candy thing was something. You stumbled into it. It’s not like you had taken an entrepreneurship course to figure that out.

To piggyback on what you were saying and add a little bit more color, at the same time that I was doing the illegal candy baron business at school, I also had a part-time job after school, scooping ice cream in Baskin-Robbins. I would get out of school and then go from 6:00 to 10:00 and do closing at Baskin-Robbins. That’s because my mother never had extra money to do stuff. From early on, it’s like, “Do you want baseball cards? Do you want new tennis shoes?” I didn’t always have good shoes. You got to figure out a way to do this stuff on your own.

That’s my thought process because I know my mother doesn’t have it. I went and got a part-time job. As soon as I was old enough to do it, I remember I had to lie on the application. You’re supposed to be fourteen. I told them I was 14 but I was only 13. I would go after school, scoop ice cream and all of that. At the same time, I’m doing the candy business.

After I got my first two teachers on payroll and I see the money I’m making with the candy business, I started getting checks from the Baskin-Robbins and I’m making minimum wage, which is $4.90, $5 an hour, whatever it was back then, I quit the Baskin-Robbins job. I said to myself, “Why would I go here and scoop ice cream when I’m making so much money running this candy business?” It was a big moment for me, even though I didn’t know it was a big moment at the time. In retrospect, it was a big moment.

You have these two experiences. One of them is self-directed value creation. The other one was other-directed value creation. If I could speculate a little bit, there’s more to it than just the money. It’s the autonomy in the self-directed pursuit. You’ve got to think for yourself. You’ve got to think on your feet as opposed to going somewhere and doing what somebody else tells you to do. If you were making the same amount of money at Baskin-Robbins as you were making with your candy hustle, you probably would’ve still quit.

I could see that. It’s because it was hard work. I’m taking orders.

You’re doing somebody else’s work. It’s other-directed. It’s not self-directed. We don’t appreciate the difference. The need for autonomy is a powerful part of who we are as humans.

Thinking back on it, you might be right. I’m in eighth grade. I don’t know all the words that we’re saying now but something felt right about what I was doing with my candy business, even though it was wrong. Something felt right about that because it was self-directed. The fact that I took the initiative, I saw the opportunity. I’ve got to create the clientele and build the brand. It’s so much that I was putting my energy into. I get out of school and I’ve got to scoop ice cream. My floor was nasty. I get the check which is half of what I made at the candy business that week. I was like, “I couldn’t do it anymore.” I quit. From that period, I’ve got to do business. I don’t know how or why but this is going to be my path.

The candy business comes to an end. You retire from your candy business at the age of 14, 15 or whatever you were at the time. You can’t replicate it. You could if you wanted to but you didn’t. You got the candy for free. Fast forward, how does that play out in your life? How does that lead to the next thing?

One thing that I always wanted to do was get outside of my neighborhood in some kind of way. Whenever I could, especially after I got my driver’s license, I would drive to other ZIP codes where there were nice houses and drive through the neighborhoods. I was 16 or 17. Once I got to that age, I was like, “I knew there was something else out here.” That started to build something that we get on our phones with social media and things but that wasn’t out back then. That built something called aspirational value. I know you know a lot about that. It created this thing in me where I have something that I can look forward to. There’s nothing in your neighborhood to model so I created that for myself by getting outside of the neighborhood when I had the opportunity to do it.

That’s mind-blowing. You would get in your car, go drive to nicer neighborhoods, drive around, look at the houses and how people were living and register in your mind like, “That’s what I want for me.”

The funny thing is I didn’t even have a car. I would sometimes borrow a car. I used to catch the bus and a train everywhere. I’m in Washington DC. I walk. Especially when I got older, I bought my first car and everything. I’m 17 or 18 at the time. I would drive as far away from that place as possible and look around. It would do something for me because I would say, “There is something out here that is bigger than what I currently see.” Being able to do that even when I got a little bit older proved that. From a young boy, I would always say, “There’s got to be more.” Once I was able to drive around and see other things, then I got a chance to play basketball and travel a little bit. I got to see how the world works a little bit differently.

That’s mind-blowing. When I was a teenager, I felt the same way. I came up in a blue-collar community. The houses only had four corners on them. They’re little box houses in rows. I used to wonder, “Why do the people who work in factories accept this?” It blew my mind like, “Why does somebody accept that little tiny house?” I was of a similar mindset. I got to find something better than what I came up with.

You said something good. You said you have to find something better. That implies that not only were you curious but you put the energy into finding it. That’s something important, finding, because not everybody goes out and looks. We’re talking about how we had an inkling, instinct or something deep down, there’s nothing to prove out what we’re saying but we looked and searched. The whole adage around seeking you shall find is a real thing. You say that you found it. That’s powerful.

I was not by any means a straight line. I went through all kinds of wrong terms, dead alleys and blind alleys to get there. This blows my mind. I’m still trying to recover from that. I saw an article in the New York Times that said the single most impactful factors have a new huge study that was released and the essence of it was exposing young people to higher socioeconomic. They can interact with and be around a higher socioeconomic. That’s by far the most impactful thing you can do to lift somebody out of poverty.

It’s because they can see it. They have something that they can look at. It’s so powerful to have something that you can model, someone, some person or some thing.

Let me ask you this. Let’s take Tremain’s identical twin, put him in the car and drive out in that neighborhood. Why are you interpreting this as like, “This is possible for me”, where somebody of equal or greater talent than you would say, “This is not in the cards for me,” for whatever reason, because of my race and upbringing? I understand why someone would do that also.

It’s understandable either way. For me, I was a dreamer and always have been. The idea of what else is there is a fundamental question that either you can ask or cannot. It is one of those things. You don’t have to ask that question because everybody that lived in your blue-collar town that never asked that question is fine. If you ask yourself that question, your current surroundings become not enough. It’s one of those things where you ask or enter at your own risk type of thing. Once you start opening your mind up to what else is out there, it makes you not content to sit where you are. That is what inspired the search process, the looking, the wanting to find and the finding.

Most entrepreneurial activity stems from some modicum of dissatisfaction with the status quo. You could look at Steve Jobs and he was dissatisfied with computers. You could look at somebody else who says, “I’m dissatisfied with my socioeconomic situation.” If you’re satisfied and everything’s going well, don’t mess with it. There’s no reason to be entrepreneurial. If you’re making plenty of money and you love your job, keep doing that. Good for you.

On the flip side of that, the person that is stuck in some generational wealth, whatever it is and they’re comfortable to be there. You don’t just have to be comfortable being rich. It could be comfortable being average, being below average or this is how things are. Back in that period, I would ask my mother all the time, “Mom, if you had all the money in the world, where would you live? What car would you drive?” Those types of questions. My mother was my tribe. I would dump all of this stuff on her she didn’t know. The funny thing is that when I would start dreaming and gazing off into the sky, “Mom, if you won the lottery today, $100 million,” she would not be able to answer the question. “I don’t know what that kind of money looks like.”

She wouldn’t let herself dream.

That’s what I’m saying. My point is that not everybody asked the question, “What else?” If you do ask that of yourself, that requires you to go out and search and start the journey of whatever it is that you’re going to end up being. Some people don’t even allow themselves to ask that question. My mother was one of them.

Some people don't allow themselves to go out and search for bigger things outside their places of comfort. Click To Tweet

I texted this to my friend, Myron, that guided the conference, Shift Omaha. I said, “I’m thinking about the ways in which our deeply held beliefs and taken-for-granted assumptions limit our vision and thereby inhibit our ambition.” You don’t even realize that you’re setting goals that are so low. It doesn’t even occur to you to set a bigger goal. That’s all happening at the subconscious level. That’s why I’m all about mindset stuff. It’s all self-limiting.

Which means that the person doesn’t even know that they’re doing it.

There’s another element to your story that I want to touch on. I’ve studied a little bit about this but psychologically, there’s a time orientation where some people are focused on the present in a hedonistic way. I’m going to party like it’s a 1999 kind of thing. Some people have past nostalgia. Some people have past regret. Some people have a future anxious

People who have a positive future orientation that you described like, “I’m looking for something better,” there’s all this research that shows that when our brains are focused positively on the future, we’re able to access problem-solving abilities that are not otherwise available to us cognitively. It’s that future positive orientation that acts on you. It’s the future pulling you into something. The way one psychologist framed this is driven by the past or navigating the future.

When I think about how my journey has evolved over the past several years, the one thing that I can say that lines up with what you’re saying is that I had no clue about what the future held. What I did know is that there was something there and I wanted to explore it to the fullest. The only thing that I knew at the time is that there was more and I wanted to explore it. What I see now can’t be it. If I’m thinking about it at the moment, that’s all I have. The future is pulling me because I’ve connected to it.

There’s also something important going on in your 14, 15 and 16-year-old brain. It’s called an internal locus of control. You’re already making assumptions like, “It’s up to me to figure it out.” Those assumptions are happening at level three in mostly an unconscious way. As opposed to a lot of folks who after however many years in school, we come to assume that someone else is going to tell them what to learn and do to be successful.

When you have a certain environment and this is something that we can both sync up on the environment, it is what pushed me to make that even if it’s an underlying decision because I can’t put my finger on it at the time but I’ve got to do something because nobody’s going to give me anything. I already know my mother can’t give me anything. There’s nothing here. Being a part of the ecosystem that you’re born into sometimes necessitates you to have to take a more proactive approach to your life. For me, business becomes the tool. It could be anything. For some people, it’s sports. For some people, it’s school and even illegal activity.

I’ve known some great drug dealers who have had great enterprises. If you think about it, the same thing that you do to build an entrepreneurial enterprise that’s legal, you have to do some of that same stuff, even if you’re doing an illegal one. You’re buying wholesale. You’re selling retail. The idea is one thing. How you deploy that into the world can be in multiple different ways. The North Star is that the future is pulling. There’s something there for me.

It’s possible. Psychologists make a distinction between active hope and passive hope. Passive hope is, “Someone else can do it for me. I’m going to win the lottery.” I sometimes say to folks, “You go into a wealthy neighborhood and try to find a lottery ticket there, it’s hard to find a lottery ticket. They don’t sell lottery tickets in wealthy areas.” Active hope is described by one guy, a psychologist, Shane Lopez. He described it as, “The belief that the future will be better than the present, coupled with the belief that I have the power to make it so.”

That’s what was going on in your brain but I want to come back to something you said. Let’s say with the situation you came up in. Don’t lose sight of the fact that your subjective interpretation of the circumstance is a huge factor. You optimistically interpreted that. Where somebody could have been in your same capacity but they could have interpreted that in a different way that was more pessimistic has nothing to do with our intellectual abilities. It has everything to do with our subjective interpretation of events. There’s a whole literature around this. What happens to us matters far less than how we interpret what happens to us.

You can have two twins that are born in the same situation with say, a mother or father who’s addicted to drugs. One says, “Dad was an alcoholic so I’ll become an alcoholic.” The other can say, “Dad was an alcoholic so I never touched the stuff.”

Somebody can come up in your situation saying, “This is my fate. This is all there ever is. This is all there’s ever going to be.” I’ll even flip the script. What we’re talking about here is optimism versus pessimism. It’s an optimistic explanatory style versus a pessimistic one. The research is mind-blowing. To be fair to the readers, you and I are both blessed that we were born optimists.

There’s a huge hereditary component to optimism. We can’t downplay that. Having said that, we can train ourselves to be more optimistic if we are more on the pessimistic side. Dr. Martin Seligman, who’s the father of Positive Psychology, describes himself as a natural-born pessimist. He wrote a fabulous book called Learned Optimism. The benefits of it are incredible. That needs to be mentioned that you were born on the optimistic side of the equation.

I will say that’s 100% correct. One thing I will say is that my mother loved me. I did have love when it came to her being my tribe. I’ve got an older sister. They loved me. Even though we didn’t have a lot, that framework around, “Does somebody love me? Does somebody care,” was intact. That is invaluable when it comes to somebody that’s developing through the different stages as you know.

Everything else, I had to learn on my own. Even having that base of, “There’s somebody here who does love me,” I feel protected when I go home, that type of stuff. Even if I had to walk through a not-so-great neighborhood, once I got into the house, there was somebody there who cared for me, loved me and would do anything to make sure that I was taken care of. That made a big difference as well.

That’s an interesting point. I hear that a lot. We all need that. What do we say to a young person who’s trying to better themselves but they didn’t have that? Are we telling them, “It’s because you didn’t have a mom and a dad that loved you. You didn’t have a family that loved you?” Are you screwed?

No. This is why entrepreneurship is good. We talk about this all the time. The idea for somebody, even if it’s just a seed of an idea that they can change their situation with a thought is so powerful. It can make you move mountains if you can say, “I can have an idea. This can change my life or my surroundings or make my kids or grandkids okay. I thought of something. I saw an opportunity in the marketplace.” There’s no candy at my school. I’ve got free candy at home. I want to buy some new tennis shoes because mine had a hole in them and my mother couldn’t afford to buy me more tennis shoes.

What do I do? I go to school and say, “Let’s sell the candy.” I’ve got enough now to buy myself some tennis shoes. These are the things that you can do as an entrepreneur. This is love, no love. This is an ecosystem, no ecosystem. This is the idea. That’s why I love it because you can take this on yourself. You become the stakeholder in your life and do not take the lottery ticket approach where something good’s going to happen. That’s a powerful thing. That’s passive hope.

Become the stakeholder in own your life. Do not take a lottery ticket approach where you simply wait for something good to happen. Click To Tweet

For a twelve-year-old kid, it’s one thing but as an adult, you can consciously create your tribe. I’ve written about this before in the Ice House book. We tend to default to our social networks, our reflection of who we are. We tend to surround ourselves with people that think and act more or less as we do. That can keep us stuck. If you’re a 17, 18-year-old kid trying to better yourself, there are many entrepreneurs out there that’ll try to help you but you’ve got to put yourself in a situation where you’re going to be around people that are smarter, richer and more successful than you. Those people will help you if you ask for help.

What you’re saying ties back to seeking. You say you found that curiosity there. If you are able to tap into that at an early age, that stays with you for the rest of your life. It’s become more evolved and acute as I’ve gotten older. I seek out new information. I seek out people who have differing opinions from mine so that I can understand the different complexities of the life that I’m living. If I’m the smartest person in the room, I automatically know I need to get into a different room.

These are the things that I’m looking for. That started because I was looking back in my neighborhood looking for something bigger there. Now it’s more refined but that looking hasn’t changed. The same thing I was looking for at thirteen, I’m looking for at this stage in my life and career. That looking, wanting to find something else and curiosity stays with me.

Let me square peg here. Were you a great student in school? Were you a straight-A kind of student?

No. The school wasn’t my thing.

This is what I’m trying to say and I want readers to understand this. Once you understand you could make your way in the world, that creates a powerful incentive to learn. That goes back to what we were talking about before we went live on the show. It’s this academic arrogance where your GPA and academic achievement scores or IQ are going to determine your life. We’re overlooking a whole other side of intelligence and human capacity that can’t be captured with those standardized tests. What I hear a lot from entrepreneurs is what you told me. “I wasn’t a great student in school but I loved to learn.”

Think about that for a second. I’ve read papers where scholars are saying entrepreneurs are the most important players in the modern economy. Let’s go with that for a second. If you realize, these aren’t scholars, people with super high GPAs or A students. How do we square that peg? How do we introduce entrepreneurial learning into the curriculum?

This is funny because I was never a great high school student. I discovered basketball in tenth grade and caught onto it, picked it up and I was good. By the time I was in twelfth grade, I was on that all-county, all-state. I was in the newspaper every week. When I went to college, I got a basketball scholarship.

Were you thinking you were going to go pro?

I didn’t know. I was opening doors for myself. I got a chance to travel a bit in high school. I’m in the paper. I discovered basketball in the 9th and 10th grades. I didn’t play any organized basketball. I came to it late. By the time I got to twelfth grade, I don’t have an agent or people going to college. I don’t know any of that. My mother doesn’t have anything to offer in that situation. She doesn’t even know how to apply for college. She doesn’t know any of that stuff.

We don’t know how to manage that situation. College of Southern Maryland said they offer me money to come there. I ended up going there. The whole time I’m there, I’m thinking about what my next business is going to be. I already had in my mind what I wanted to do. I stayed in college for 1 year and 1/2 of the second year and dropped out to start my first tech company.

Fast forward seventeen years and the next time I’m in university, I’m at Howard University teaching an entrepreneurship class. My wife and I joke all the time. She got her Master’s degree from Howard University. She goes, “I paid all that money to Howard. I’ve got student loans. All you have is a high school diploma and you’re teaching there.” Teaching entrepreneurship and a skillset that can help people wherever they are. Cross-discipline. I taught MBA students and Sociology students.

It didn’t matter the discipline. They all came and took my course at Howard. They wanted to know more about entrepreneurship. That was the power of it for me because I’m standing in front of a class, teaching at a major university and I don’t even have a college degree. That’s the door that entrepreneurship opened for me along with other stuff. That in particular, when we talk about education, shows the power of entrepreneurship. I dropped out of college in 2001. The next time I’m in a college, I’m teaching. That’s something that you can only attribute to the idea of entrepreneurship and being able to follow your path and do your thing.

It’s self-directed. That’s what it comes down to. I want to back up. You had a mom that loved you and cared about you but she didn’t know how to help you navigate the world you were going for. She had to be incredibly proud. Her kid’s going to school with a full-ride scholarship. Your mom must have thought she hit the lottery or something like, “What got into my kid?”

You know how you had the first generation. I was the first generation. There are not a lot of people in my family with degrees. That’s not a thing in my family. Imagine I’ve got a full ride to college, paid for to go play basketball. I was the stuff in my family. I want you to imagine me telling everybody a year and a half later that I’m dropping out to start a business. They thought I was insane. Everybody thought that I was crazy, “Why don’t you finish your degree? It’s free, then you can start the business.” Something was pulling me. I couldn’t go on any further. I dropped out.

I want to ask maybe a sense question here. In the Black community, that has even more of an impact than it might in the White community. For you to be the first generation, you’re like, “Am I hallucinating?”

Going back to that period, entrepreneurship and starting businesses are not a thing. It’s like, “I’ve got an idea. I want to go start this thing.” It wasn’t like, “I’m doing entrepreneurship.” This was some crazy thing. It sounded like a moonshot. The safe thing is, “Go finish your degree. You are one of the first people in our family to have this opportunity to get a degree and do something higher paying to get a good job and benefits.” Break the mold, that’s what they saw this as. Success in my neighborhood is working for the power company and light company.

They were people who were making $50,000 to $60,000 a year driving a trash truck. That would’ve been a success. If now I have an opportunity to get a free education playing basketball, I could potentially do more. That’s what everybody saw. They rallied around me. People were like, “I can’t believe you’re going to college. You’re playing basketball. Go do that. That’s exciting.”

A year and a half later, I’m saying, “I want to leave the free ride, the free education and all that stuff on the table to go pursue this idea.” That was something that people couldn’t understand. They had no concept of what I was talking about. It sounded so insane to them to leave security. That was security. You can come out and get a good job, benefits and insurance. Those are the things. You’re going to leave all of that on the table to go do this thing.

Baskin-Robbins is in the back of your mind. It was something Clifton told me when we were working on the Ice House book together. He said his Uncle Cleve would drive him home. He would drive right past his house in the morning, wouldn’t pick him up and say, “It’s your job to get yourself there. I’ll get you home.” He told me he would drive him past the cotton fields and say, “There’s no future there for you because there’s no thought required of you.” It’s too easy to get on a field truck. That field truck is a metaphor that a lot of people can relate to. The field truck might pay you $80,000 or $120,000 a year but you’re still getting on a field truck. Were you freaking out? Everybody’s doubting you. Did you have any self-doubt?

I was scared to death. That’s because I’m going against all of the traditional wisdom that’s around me. That’s another thing, the people that were saying, “You’re crazy. Go back to school.” They mean well. We could probably talk for two hours about how sometimes the people who are your biggest detractors are the ones that love you the most.

They encourage you to take the safe path.

“Take the safe path. What are you doing? This is a free education. Why wouldn’t you try to start whatever this business thing idea in three years after you finish your degree for free?” Here’s the crazy part about that, Gary. That makes total sense if somebody says that to you out loud. What doesn’t make sense is this thing over here that’s pulling me.

Nobody can see except you.

It’s a thing that I don’t even see clearly but it’s pulling me. I’m being pulled by the future. It was attracting me. It was like the Earth’s gravity. I couldn’t escape it. Basketball became not fun for me. I lost the desire to play. I’ll tell you what did it in for me for basketball because I was already thinking, “I’ll play this last year.” You can get a two-year Associate’s degree. I said, “I’ll get the Associate’s.” I was already in my second year. “I’ll finish playing basketball this year, get the Associate’s and then go for my business idea.” I’d already thought it through. I knew what I wanted to do. I already started talking to people about it. I knew what I wanted to do.

What happened is I ended up getting hurt. I broke my ankle, something along those lines. I was out of basketball for three months. The only reason I was in that college is that I got a free ride to play basketball. That broke my spirit as far as the desire to want to stay for the rest of the year and finish that Associate. I dropped out and quit. I said, “I’m going to go after this business stuff because I can’t play anyway.” I was out for 2 to 3 months because I was in a cast and couldn’t play.

I said, “This is it. I can’t go on any further.” After I got cast off, I had rehab. It would’ve been a little bit of a road back to the court. I’m having to take classes even though I’m not playing. I got this thing, the future’s pulling me. I love that. I’m going to put that on a screen saver somewhere. I dropped out and went and started my first company.

That’s such a cool story. I want to piggyback on something you said because I want people to understand this. The entrepreneurial mindset is the effect of entrepreneurial behavior. The cause of entrepreneurial behavior is our innate organismic tendency towards growth and self-actualization. You had a taste of it as a kid, that autonomy. People noticed you. You figured out how to make your own way. You’re paying teachers to cooperate with you. You developed at an early age a sense of agency.

The point I’m trying to make and I’d love to hear what you have to say about this is the entrepreneurial spirit is the human spirit. It’s not in some of us, it’s in every one of us. All these forces can thwart it very easily. The desire for growth, exploration and discovery is in every person but we also need safety, stability and security. We often default to safety and stability at the expense of the exploration. Does that make any sense to you?

It makes total sense. Something we keep coming back to is that if you opt out of the exploration for safety and security, that is understandable.

It’s unnecessary too. That’s what I’m coming back to mindset. In my model, what I’m advocating for is don’t quit your day job. Don’t mortgage your house. Don’t drop out of school. Experiment in the margins. Use some of your discretionary time, thought and effort to figure out new ways to make yourself more useful to more humans. You can hear it in people. You can have conversations with people right away. You could hear others talking about the weekends, holidays, recreation and sports.

They’re not talking about ideas and a future they have control over. To your earlier point, it’s all too easy. How many of us wind up at 30 or 40 years old? We come to assume at an unconscious level that the world is the way it is. “I am who I am and there’s nothing I can do about it.” That belief lands in our brain at an unconscious level but it shows up in our behavior.

That’s a seed. It gets planted and then it grows. Once you start to see the branches from the tree, that’s what you’re talking about, the above-ground stuff. It started as a seed. That’s why I feel like my experiences at such an early age with entrepreneurship and thinking how I was thinking was the time to redirect what was going to grow out of my seed. Once you start getting to the aboveground stuff and there are branches, trees and leaves, it becomes difficult to chop that thinking down.

If you are getting to it at a seed level, it grows into something that is much more exploratory and curious. The fruit on a tree is based on the seed that you plant. If you plant an apple seed, you get an apple tree. If you plant curiosity and you plant these things off, there’s got to be something more if those are the things that are planted early. Once you get to be the age that I am and the age that you are with years and decades of experience now, it is acute in me that I’m always looking for something new and finding opportunities. That’s the fruit of the tree.

There was a scholar named Jerome Bruner back in the ‘60s. He wrote about discovery learning and the power of discovery learning. What he talked about is we develop the heuristics of discovery. That’s what you’re talking about. Heuristic is like a mental model, like a shortcut or a rule of thumb. That’s what you were talking about. We develop those heuristics through our experience but we have no idea how to articulate them to somebody else. That’s part of the problem. That’s what I’m trying to do with this show. Let me pick you up. Most of what you know, you learn through experience. You didn’t learn it from reading a book or taking a test. That’s called tacit knowledge.

This goes back to the intelligence thing we were talking about. Scholars call this implicit learning, learning without effort or awareness that you’re learning. It turns out your brain’s capacity for implicit learning is 1,000 times more potent than your brain’s capacity to learn explicitly through a book, a course or something. The problem is the knowledge we acquire implicitly is often tacit. The way this guy Michael Polly described it was like, “I know more than I’m able to tell.” Tremain sells his business for $100 million. Inc. Magazine and Forbes show up and interview you. They go off and write this piece about what they see in front of them as this confident human. They say, “To be a successful entrepreneur, you got to have all these things that Tremaine has.”

They don’t know, though. There’s another side to that story,

They didn’t see Tremaine when he was a little wobbly need chicken that couldn’t find his thing with both hands.

That story rarely ever gets told.

That’s what I’m trying to tease out here in this show. Somebody will sit you down and say, “Tremain, you borrowed $5,000 from your mother-in-law years ago and you built this big business. How did you do that?” The answers you provide aren’t likely to be that useful unless you go into a pretty in-depth interview. What I’m likely to take away is, “I worked hard. I never gave up.” That’s not that helpful. I’m trying to get to a deeper level at what’s going on behind the scenes and underneath the hood. What are the unconscious beliefs and assumptions that are driving the behavior that’s enabling you to succeed? That’s what I’m trying to figure out.

First of all, you have to change your relationship with failure. That’s something that I had to learn, first and foremost. You have to be able to go into a situation knowing that the odds are not great but you’re going to go in and do it anyway. That’s something that I had to learn over time that changed the game for me. The second piece is being able to learn. I’m talking about becoming a life learner. That’s the only way to get to some success at the end of any entrepreneurial journey, pursuit or anything like that. I’m still trying to figure this out.

Change your relationship with failure. You must know how to go into a situation where the odds are not great, but you will still do it anyway. Click To Tweet

I don’t know if it matters if you never get to the end of the road, never cross over and never get to that “success”. If I would’ve been that kid that dropped out of college several years ago and I would’ve never made anything of myself or let’s say I end up being a trashman in the neighborhood or something like that, would this story even matter? Would it even matter if that was the end of it? It’s the ability to say, “I’m going to go into this.” I’ve failed a ton. What makes entrepreneurs powerful is that they’re able to learn from those failures and take the good stuff, apply it better the next time and throw away the bad stuff.

Entrepreneurs are powerful because they learn from their failures, take the good stuff, and apply it better the next time. Click To Tweet

You keep refining yourself. It’s like gold. You keep refining. Without that refining process, you become a person that was able to have the optimism, see the opportunity, able to go out there, maybe even start the business and have the entrepreneurial mindset. Have these things, even creating the guardrails. Even if you have those things, if you’re not able to refine over time, take those learnings and take them into the next thing. That is what has made me the person that I am. I can look at a business deal and right away, I know.

That took me many years. That’s because I was able to learn what wasn’t good. I’ve been in business deals where somebody will shake my hand and say they’re going to do X, Y and Z and screw me on the back end. They knew when they were shaking my hand that they were going to screw me out of $100,000 a month later. They knew it. Those are the things that you have to live through and learn.

When somebody shakes my hand, I’ve got a whole new understanding of how to assess those businesses and things like that. If I never go through that refining process, I still make those mistakes. With a family and kids, getting a little bit older and having to worry about retirement things, those mistakes become much more costly, which is why the refining process is necessary.

You said a lot right there. I want to get into the self-directed learning you start at the beginning of that last rant. You were talking about being a self-directed learner. I want to know what that looks like for you. Are you an audiobook guy or a YouTube guy? Are you a network guy who learns from mentors? Is it all of the above? Are you taking college courses? What does self-directed lifelong learning look like for you?

This is a university that I suggested everybody go and apply to. All your readers need to go apply for this university. They’re always taking applications. The tuition is free. It’s called YouTube University. Everybody that’s a reader needs to go apply to YouTube University. They’re always giving out scholarships. You can always get in. For me, what I had to do to become a lifelong learner is I had to learn in the gaps. What that means for me is that if I’m driving somewhere and I’ve got a 30-minute drive in the car, I’ve got a 30-minute drive back home, that’s time for me to listen to an audiobook. Or something that’s going to be productive for the market that I want to go into on YouTube.

Access to information is limitless. That’s something that has become a real mantra for me. When it comes to lifelong learning, I equate that to learning in the gaps. As I’m driving or showering, it doesn’t matter. Showering, brushing teeth or ironing a shirt, that’s a 20-minute gap where I could get through 2 chapters of an audiobook. That’s how I equate learning.

It is what I call learning in the gaps. Anytime I have a gap in my life whether it’s driving, walking, exercising or showering, it doesn’t matter. Everybody knows these headphones that I have on, they’re connected to my ears. It’s always something playing that I’m learning from. I’m always listening to the World Economic Forum and Harvard i-LAB. I have many subscriptions to many different business economics and those type of things.

We’re brothers from another mother. I was telling somebody that I probably read 25 books a year. I do it through Audible. I do it when I’m driving to the grocery store. I do it when I’m on a treadmill exercising. It’s in the margins and gap. I have a huge advantage. Twenty-five books a year, that’s a lot. Most people won’t read that much in their whole life after school.

The thing is that a lot of times, people take for granted those times. That’s why I call it learning in the gaps because if you can find those gaps and then start filling in that time with information, those moments are not dead times in your life. If you add up all the times that I call gap time, there are so many hours in a week. It’s massive. It’s almost like the stock market. It’s compound interest. The kind of learning that you can have in those gap times can set you up for the rest of your life.

This is such a powerful conversation. I’ve been thinking about this a lot. It seems so simple and obvious to you and me. It’s like there’s Stanford University’s available to you on your iPhone for free. I’m trying to walk the cat back here. The question is, why don’t people see the value of learning? That’s what blows my mind. How did you get to be an adult? What do you mean you don’t read nonfiction?

Are you a multimillionaire? Are you on Facebook looking at social media wars? This goes back to something we talked about at the beginning of this conversation, the locus of control. At a deep level, if you’re not learning the way Tremain explained learning, it’s because you got to a deeply held belief that nothing you do will matter and there’s no point in learning.

If you hit your ceiling, you can’t get better.

The nasty part of that is we arrive at those beliefs unconsciously. There was a Scottish psychiatrist named R.D. Laing. He said, “The range of what we think and do is limited by what we fail to notice.” He went on to say, “We fail to notice so there is nothing we can do until we notice how failing to notice shapes our thoughts and deeds.” It’s like a little bit of a mind-bender for a second.

That’s why I’m so dialed into the mindset. In this conversation you’re having, what I notice about most entrepreneurs that I’ve interviewed is they might not be the sharpest tools in the shed. I’m not saying you’re not a smart guy but I’m saying they know how to get all the horsepower out of whatever engine they got. That’s what I’m hearing you say. What you’re constantly absorbed with is, “How do I make myself better? How do I learn more? How do I get to the next thing?”

Once you get into that mind frame that we’re talking about here, the next thing, the next level, the next plateau, however you want to coin it, that becomes an output and outcome of what we’re talking about. Once you get to this phase, you don’t even chase the next level. You chase the process of adding more to yourself. Once that becomes the core thing, I’m getting excited that I’ve learned something new. I’ve learned a new perspective.

I’ve heard something that can take my thinking about a topic to another level. Adding those complexities to who you are makes you more valuable in whatever market you walk into, be it your job or business. Having more value internally increases your bandwidth to add more value externally. That’s what takes you to the next level. That’s what creates that outcome, that next step or whatever opens that door. It’s not the door or the next level. To me, that is not the thing that I chase. I chase wanting to increase my bandwidth. How do I expand my borders?

You’re trying to be a better version of yourself. You’re not trying to beat somebody else.

I want my 2022 self to kick my 2021 self. That’s the year-over-year growth that I want to have. If I’m not seeing that, that means that I’m not doing something. If I’m not getting the result that I want to get in my life, that’s where I have to start. How do I increase my bandwidth? The next level is not about the next level. Getting in the room is nothing. How do you stay in the room? Getting to the table is nothing This is something that I see a lot, especially in our community. We’ll “get to the table” in certain rooms but the problem is that we’ll get to the table and we want to take our plate to go instead of staying at the table and conversing with the people at the table and trying to build a relationship at that table.

It’s like, “I’ve got to the table. Let me get as much of this buffet as I can and run out of this door because I’m not supposed to be here anyway.” The thing is that when you get that opportunity and you get that seat at the table because you haven’t prepared yourself again by increasing your bandwidth, when you do get that opportunity, that shot at the next level, that seat at the table, you don’t even know how to sit there and have a meal. You get there and it’s like, “I’m not supposed to be here anyway.” That’s because you haven’t done the work inside. That’s why the next level can’t be the thing.

The other thing you said in there that I want to jump into for a second is you described something where learning is fun. Learning is a source of joy and enrichment. Work is a source of joy, exploration and growth. I’m looking at the engagement statistics from Gallup. The vast majority of human beings on this planet are phoning it in. For most people, learning and work are necessary evils. That’s what you and I are trying to help communicate in this conversation. What if every young person could have that experience a little bit where learning and work become a source of joy, growth, inspiration and fun? That’s how we could change the world right there.

One thing that I’ll add to that is the ecosystem of what technology has been able to bring to this world, meaning that we’ve got all of the world’s knowledge in the palm of our hand via a smartphone is an incredible tool to take yourself personally to the next level. What creates that bandwidth and opportunities is you have to have something that you’re passionate about. You can go out and learn anything you want about whatever that thing is. You can do it in private, in the bathroom or late at night. You don’t have to have an outside opinion to tell you that you can’t go learn something. That’s the great part about the times that we’re living.

I’m excited to be in 2022. There’s more opportunity than ever before in the history of mankind. It’s because of the technology and where we are. It’s so much opportunity for all of the things that we talk about as far as systemic racism and all of the things that Black people deal with in this country. Those things are true. This is the greatest country on the planet. There’s so much opportunity right here in the United States. I wouldn’t want to live anywhere else because there’s so much that I can do to bring value. I’m talking about it on a global scale just because I live here. Anybody can tap into that energy.

It is no longer something that’s only reserved for a select few. Somebody in a neighborhood that I grew up in or the neighborhood that you grew up in, the blue-collar town, the rural community, the urban city center, it doesn’t matter. If something is tickling your fancy, sewing, bowling or whatever it is, you can go out right on your phone and learn everything that you can learn about whatever that thing is. That’s what increases your bandwidth to recognize the opportunities for the next level.

I’m always trying to break this down. Entrepreneurship’s not that complicated. I love Aristotle’s idea of first principles. You hear Elon Musk talking about and breaking down first principles. I love that kind of thinking. Break something down to its basic parts where you can’t tear it apart anymore. I’m thinking about it like this. Adam Smith wrote this in The Wealth of Nations in 1776, “Every man lives by exchanging.” I’m going to extrapolate. We all live by exchanging useful things with each other. That’s how we earn a living. Most people will accept that premise. You got to figure out how to make yourself useful to other humans.

The question is, what is the useful thing that you’re exchanging? Everyone shouldn’t be asking themselves that. To whom is it useful? With whom are you exchanging? The more important question is, what is the means by which you make yourself useful? Is it other directed or is it self-directed? These are fundamental questions. I have one more.

They’re designed to bring your level three deeply held beliefs and assumptions up to your conscious level. That’s what they’re designed to do. If you keep walking away thinking, “I never thought about it that way.” The ultimate question is, what’s preventing you from making yourself more useful to more humans? The more useful you become, the better off you’re going to be.

I want to throw something into the mix on that because that is powerful what you said, especially the quote about we all exist based on exchange. That is such a powerful idea. For many people, the only thing they have that they can exchange that’s valuable to somebody else is time. That’s where you get into the idea of going to work for 40 hours and then you get paid for that. You’re limited. If the only thing you can offer somebody that’s of value is time, then that limits what you can do because you only got 24 hours of them to offer.

If the only valuable thing you can give others is time, it limits what you can do. Click To Tweet

I got to show you something. I put this in my new book. I’m going to try to do this for you right here. I’m going to do this simply and see if we can pull it off on the webinar. This is what I call the value volume index. The vertical over here is the value. That’s the amount of usefulness you are. This is the volume. That’s the number of people that you are valuable to. Let’s take a brain surgeon. He’s high into the left. He’s useful to a small number of people.

You take Beyonce. She’s way out here, low into the right. She’s a $0.99 value for a whole lot of people. The thing is we should all be trying to get ourselves high into the right. To your point, high into the right. You got a phone with all this content on it. You’re sitting there watching stupid Twitter wars or something. You don’t need to be a genius.

This is an opportunity.

It is but it all starts with the underlying beliefs. I’m almost embarrassed to say this. We’re an hour and a half into this conversation and we haven’t even gotten into what your business is. This happens a lot. I’m endlessly fascinated with the way that entrepreneurs like you are so dialed into the mindset. They’re conscious. You’re always thinking about your thinking. This reminds me of failure. There’s an aspect of the failure piece that I wanted to dig out. It could be failing on a small scale, a little experiment. It didn’t work out properly. It doesn’t have to be an epic failure like, “I lost everything.” We don’t tend to blame a lot of people.

There’s a cognitive bias. It’s called a self-serving bias. The way the brain works is when things go well, we take credit for it, “I’m a genius.” When things go badly, we tend to blame others. We look for external attribution for the failure. That’s not because we’re sociopaths. It’s because we’re not aware of the ways in which our deeply held level three beliefs led to the failure. We’re blind to it. When you and I are failing, we’re looking inside. We’re not saying, “The market’s too stupid. People don’t get it.” We’re thinking, “I went about it wrong. I got it.” The power in that is, “I only have control over me. I don’t have control over anybody else.”

You’re taking ownership of what that outcome is, be it good or bad. It’s very easy to take credit for good. Real character is built when you can take credit for the bad as well. I would even venture to say you can credit for the bad, even when it’s not even necessarily your fault. I’ve participated in businesses where there were partners and something didn’t go right because of the partner.

Take ownership of the outcomes of whatever you do. It's easy to take credit for the good, but it takes real character to take credit for the bad. Click To Tweet

I still will say, “What could I have done differently?” Even the partnership, “How did I not recognize that this partner was not aligned with the core values?” That’s something that I’ve got to do a better job at. It’s the refining process. These are the things that catapult you. You can’t get away from the next level if you think like this. The next level comes and finds you when you’re doing this introspection after every experience.

I love you for saying that. I’ve said that in a different language. It’s like a bitter pill. The minute you realize you take that bitter medicine, you become empowered. By refusing to take that medicine, you’re holding yourself back. You’re blinding yourself. You’re interrupting that feedback loop. What you and I are doing is called error-based learning. That’s how organisms orient themselves on unfamiliar terrain. It’s antithetical to the way we learn in school. In school, learning is the worst thing that can happen.

I don’t want to lose sight of your business and how you went from dropping out of college. Your family’s freaking out. You feel like you’re being pulled to this future that you can’t even quite see. I can’t help but think about the candy. Part of your brain, you’re looking at the candy experience and the Baskin-Robbins experience. How did that play out?

I’m a three-time founder. I’ve also done a bit of agent investing. I’ve invested in a handful of companies over the last several years as well. The same thing that pushed me to start the candy business, that thing is still in me. It’s just more refined, acute and dangerous. That’s the seed of it was there back then. I started my first tech company right out of college. We raised money and built a team. I didn’t know what I was doing. I’m flying by the seat of my pants.

Right out of school, you’re a dropout. You raised money. How did you do that? You don’t fit the profile either, I hate to tell you.

The area that I was in was not Silicon Valley. I didn’t know what I didn’t know. That’s a real statement that rings true probably for a lot of entrepreneurs, especially early on. Especially when you’re young, you think you can do it. You don’t even understand all the forces that are against you at the time that you’re starting. We went into this with the understanding that there’s a problem that we want to solve.

Ultimately, the business enterprise was not successful but it was all because of the timing which is something I teach all the time at university. The technology that was needed for what we wanted to build didn’t exist years ago. It shows you how far we’ve come in several years. This is pre-YouTube and pre-Facebook. None of those things existed. We were getting off of pagers and flip phones. iPhone didn’t exist.

We’re in the Stone Age. We’re getting off of dial-up internet. The core piece of what we were trying to do was all around streaming video. Streaming video is something that didn’t exist at the time. We didn’t know that we were trying to go into streaming video. We were trying to solve some small piece of it. It all had to do with my experience. To your point, your experience shapes what you want to do. My whole experience with recruitment, basketball and getting into college and a scholarship was such an old-school analog process with VHS video tapes and sending those tapes by snail mail to college coaches and all of that. I said, “It’s got to be an easier way.”

This is something I was thinking about right in college. There’s got to be an easier way to streamline sports recruitment. What we set out to do was start an online sports recruitment service. It was going to be pretty much a SaaS platform with all these different bells and whistles. The core value proposition was that some coaches in California could log on, create a profile and pay a monthly subscription.

All these athletes would put their profiles on this service for free. The athlete could upload 30 seconds of their game film onto this website. A coach in California could see 30 seconds of a kid playing in North Carolina. If you’re a college coach, a scout or anything like that, you could see how a kid moves in 30 seconds, see his shooting form and how he’s moving. You automatically know, “This is a kid I need to go see.” It doesn’t take long if you’ve been coaching or doing recruitment.

If you’ve been doing that stuff for years, it doesn’t take you long to see what a kid can do. That’s what the whole thing was about. It’s about uploading this video onto this platform. It’s all stuff that is easy and obvious but that’s because we got iPhone, Facebook and YouTube but this was five years before any of that stuff. It’s out of a doubt. The technology for what we were trying to do didn’t exist yet. That experience taught me so much. We went out and pitched it to colleges and universities. They were all interested. We had tons of clients.

We raised money but we could never get over the technology piece of it, which is how do you stream this video? How do you upload videos? That wasn’t a thing back then. How are we going to store the video? There was no cloud back then. How are we going to store all this content? These were the things that we were up to. This was a sign of the times. We were trying to do something that didn’t exist. We beat our heads up against the wall for a few years and raised the money. We ultimately couldn’t get it off the ground because we couldn’t solve the streaming video piece.

That was my first iteration as a taking something-to-market entrepreneur and building out this tech platform. It was an incredible experience. Even though we ultimately didn’t make it, I learned so much about entrepreneurship from that business. I bet on myself and would not change a thing. I went on my second business, which was doing investment consulting. We started a firm down in Atlanta, pre-2008. We had a good run down there for three years before the market crashed. We did some coordinating work with the DC government. I started my company several years ago, Davis Investments and Management. It’s a strategy management firm.

What we do is build strategies all around economic development models. This is what you like and where it connected us all centered in entrepreneurship. That’s what we do. It’s all about building economic development models. How do you lift whole communities using entrepreneurship from a community model? It’s cluster-based economic development. The regional cluster-based economic development means that what you do in Milwaukee is different from what you’ll do in Miami. There are different needs regionally around the country. It’s got to be regional. We talk about economic development. The regional cluster-based economic development is all about the ecosystem. It’s what we’ve been talking about this whole time.

How do you create an ecosystem in a community so that you’re not just dropping money into a community so you understand the regional piece of it, meaning that there are needs that are different? You use entrepreneurship so that you can empower people to be able to bring their ideas to the forefront, make that community a stakeholder, make those people in that community and give them the tools they need to solve the problems in their community. Once they launch that business enterprise and they’re ready to hire their first two employees, they hire right in that community.

Use entrepreneurship to empower people and help them bring their ideas to the forefront. Give them the tools they need to solve problems in their community. Click To Tweet

That becomes a powerful tool for economic development. We build those models. We deploy in different parts of the country. We work with city governments and school districts. The thought process is how do we take large populations of underserved, under-resourced people and give them the tools to buoy themselves and take that? It becomes generational. That person can teach that son, daughter or granddaughter. I always come back to a statement where if mom or dad doesn’t know anything and then they teach their kids all they know, you get into a cycle where generationally, you’re not passing down that knowledge. That’s something that we want.

That’s such a cool story. The way I think about mindset is to a person what culture is to a group. There’s a bi-directional relationship that culture shapes your mindset and your mindset can shape the culture. The dangerous thing is whether you’re talking about mindset or culture, you’re talking about deeply held beliefs, values and assumptions that we assume to be the correct way to perceive, think and feel about a specific problem.

We transfer that to new members of the group and teach them that it’s the correct way to perceive, think and feel. That’s what you’re getting at. I got to connect you to Myron. The name of the conference I was at in Omaha was Own the Pond. You get it right away. He’s saying, “Forget about giving a man a fish. We’re not about that. Teaching a man of fish is all good but we’re trying to teach people to own the pond and build a legacy of ownership that can pass down generationally.”

To piggyback right in on there, what we do at our company is codify how that action happens on the ground so that as we’re talking about it at conferences and things like that, how do we establish what that looks like on the ground? How do we create those partnerships in the community? We’ve done tons of work about what makes good anchor partners in the community. How do those secondary and tertiary partnerships look?

How do we address the cultural and social needs in that community as we’re bringing out the ideas, cultivating the solutions, crafting and finding the problems? Those are the things that you have to know. It’s good to talk about it in a conference room and on a whiteboard but how did this stuff look on the ground? That’s what we specialize in.

I got to connect you with another friend of mine, Thom Ruhe. He runs a foundation in North Carolina called NC IDEA. One of his ambitions is he’s trying to make North Carolina the most Black friendly business state in the country. He created something called the Black Enterprise Council but he went about it in the right way. He convened a panel of Black leaders, gave him some money and said, “You guys go do this. I’m not doing it.”

I would love to work with an organization like that. This is where we add a lot of value because what tends to happen is that capital deployment will happen. The assumption is that the people who receive that capital infusion has the processes to put it to work on the ground. That’s generally where the disconnect happens. Once that capital infusion happens eighteen months from now, the person that cut the check will say, “Where are the outcomes?”

That’s because generally, the people who are working on the ground, the people who are doing God’s work, the non-profits, the mom-and-pop and NGOs don’t know how to do that work at scale. That’s where we can come in and add a lot of value. Somebody who says, “I got $1 million, $5 million, $10 million, whatever it is, I want to drop it into the community. Who are your community leaders? Here’s the money,” those people generally don’t know how to organize these ideas at a skill.

That’s where you get some of the disconnects. They’ll be able to help their 50 kids and the nonprofit in their neighborhood but that’s not something that could help a whole ZIP code or city. That’s when you have to start getting into the larger partnerships. We’ve done a lot of work about what makes a good partner, whether it’s a school district, city government or library system.

We do tons of partnerships with library systems because not everybody has internet access at home. Those are the type of partners that make great anchor partners in a community. If you’re not thinking about it in terms of how you scale these ideas, then it becomes something that generally won’t give you the outcomes that you’re looking for.

I love that you’re taking your entrepreneurial experience and using it to scale entrepreneurship. You and I are trying to do the same work. This is an endlessly fascinating conversation. I feel confident we’re going to have at least a part two at some point because we’re not going to get close to it. Is there any takeaway from your experience you want to leave who are winding down? Is there any big takeaway from your journey as an entrepreneur? How has it impacted you? What do you think about yourself?

I feel blessed and fortunate to be at the place where I am in my career because I can look at how I package everything that I’ve done over the last several years and point it towards purpose. That’s meaningful for me. I get up every day because I know that all the experiences that I’ve had and all the refining that I’ve done, I’m still learning and refining but I’m to a place where I can point everything towards purpose. If I can go into a community and start doing scaled solutions to help thousands of people, that’s something that becomes powerful for me in my life because I feel like I’m having a generational impact.

That’s what it is for me. As far as what I want to tell or leave to somebody else is that anybody can do it. I’m not special. One of the first things that we talk about when we go into communities from a social standpoint is letting people know that they can do it. You would be surprised at how many people have never been told, “You can do it.” It might sound small and trivial but some people have never been told, “You can do it.” I want to leave that with the readers.

That’s such a beautiful place to end. It’s such an important ingredient. We need to see relatable social models. We need to see people look like us that came from where we came from succeeding. That’s a real game changer that’s sometimes left out of the conversation. “Stop talking about Elon Musk, Mark Zuckerberg and Jeff Bezos. Show me somebody whom I can relate to that’s making it happen.” That’s what you’re all about.

It empowers people, I believe. It gives them power. That’s what I’m all about. I want to give somebody else the power to empower them to go out and do the things that they want to accomplish in their lives.

That’s what entrepreneurship’s all about. Where can people find you?

I’m not huge on social media but Instagram, @IAmTremain. My website is DavidsAndDavisIM.com. IM stands for Investments in Management. Davis and Davis Investments in Management. I also started a nonprofit. It was to house this thought process. We’re still building out what that looks like but we started working through the case studies, the white papers and different things like that around what this model for cluster-based economic development looks like at a scale look. The website for the nonprofit is ThinkPGC.org.

Thank you for sharing and sharing your time and wisdom and experience. This has been a fabulous conversation. It’s over. This was the fastest two hours of my life.

This has been incredible.

I’m going to come back to you for a follow-up interview. I want to say thank you. Let’s talk again soon.

Thank you so much for having me, Gary. This has been such an incredible gift to be able to meet you and be on your show.

Important Links

• Davis and Davis Investments and Management
• Learned Optimism
• Who Owns the Ice House?
• The Wealth of Nations
• NC IDEA
• @IAmTremain
• ThinkPGC.org
• https://www.SocialCapital.org/?dimension=EconomicConnectednessIndividual&dim1=EconomicConnectednessIndividual&dim2=CohesivenessClustering&dim3=CivicEngagementVolunteeringRates&geoLevel=county&selectedId=06037

About Tremain Davis

Experienced entrepreneur and investor with a demonstrated history of leadership in the high-paced entrepreneurial space. Subject matter expert in community engagement strategies.