In this episode of the Founder Origin Stories, Sherry interviews LaTesha Burroughs of Optimize Player, about her early entrepreneurial endeavor of selling sneakers as well as her relationship with her parents.

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Episode Transcript

Rob Walling:On ZenFounder this week, we continue our founder origin stories as Sherry Interviews LaTesha Burrows. LaTesha is an entrepreneur, and a WordPress aficionado who’s always dabbling in things related to marketing, design, development, and business. And I hope you enjoy Sherry’s conversation with LaTesha today. But before we dive in, I’d also encourage you to head into iTunes, or Downcast, or Overcast, or Stitcher, or whatever software you use to consume this podcast, and give us a five start review. Five star reviews helps us get found in the iTunes repository. They help us grow our audience, and frankly, they give us motivation to just keep putting out high quality shows. You don’t even need to write an actual comment, you can just click the five star icon. And we would really thank you for that, if you get any type of value out of ZenFounder.
Sherry Walling:So, for people who don’t know you, since you haven’t been someone who’s been super out there with your story, or you don’t have a podcast, and stuff like that, but say a little bit about what you’re doing right now. I know you just launched something, so give us the five sentence version of your current business. And then we’ll work backwards.
LaTesha:So, I currently run a start up called OptimizePlayer, which is a video marketing automation platform. So, pretty much you can tell it, if somebody watches this much of the video, or if they’ve performed this action on the video, tag them in drip, or another marking automation-
Sherry Walling:That’s for that shout out, right there.
LaTesha:Yeah.
Sherry Walling:Perfect product placement.
LaTesha:Shout out to Rob. Yeah, so you can tag them in these CRMs and these automation platforms, so that you can follow up with them more appropriately.
Sherry Walling:Okay. So, just using video content, you’re basically using video to build your list. Or to build follow up into your business.
LaTesha:Exactly.
Sherry Walling:That’s cool. So, yeah. I sat down at a meal with people at Microcom last spring, and just put it out to the table. There were maybe seven or eight people there, and I said, who’s story do you guys want to hear? Who are you curious about? Who’s got something going on that doesn’t necessarily get a lot of air time? And I think it was Justin Jackson who was like, you’ve got to talk to [LaTesha 00:02:55]. You’ve got to get her story, she’s so … Just who she is, and I could tell … You know, there were some heads nodding around the table. People have a lot of respect for what you’re doing, and what you’ve built over the years.
LaTesha:Yeah. I’m so grateful to hear that. He’s been so monumental right now, in this time. Because he’s just a great people person. So he brings the best out of you. And especially somebody like me, who is in their shell, Justin Jackson is just great for that type of personality.
Sherry Walling:Yeah. Every introvert needs an extroverted best friend, or an extroverted person in their back pocket. So, you got started … You won some early awards for entrepreneurship as a teenager, right? You started a business selling sneakers when you were still in high school? Do I have that right?
LaTesha:Yeah. You have that right. So, a little bit before high school, but I would say high school was the pinnacle point. And I did win some awards with Black Enterprise, Forbes, and some other magazines, at the time. Yeah

 

Sherry Walling:So what was that business? And Forbes, that’s … I mean, these are really cool accomplishments as a young person.
LaTesha:Yeah. I mean, they really were, and it was everything that I wanted. But I think it was like before my time … Before I even knew what that stuff meant, you know? It was a great accomplishment, but I don’t think I understood the gravity of it. I was just very grateful, and just kind of like living in the moment. But the business that won those awards was Krazy Kicks, it was called. With a K and a K, so it had a really funky name. And so, growing up, I lived in Okinawa, Japan. And over there, they have a sneaker scene that is just huge, of all the Air Jordans, Air Force Ones. It’s just really a big culture of sneakers and hip hop, so to say.
 And so, I owned a collection of sneakers that my mom would just buy me. I think I had a few dozen. And so, what I did was I took those shoes that I owned, and I put them up for sale. I don’t even remember where I put them up for sale, because there was no e-commerce at this time. I just remember getting them somehow up on a website, all listed in a row, with a price. And it was a white website with the ugly logo. And sold my sneakers there. I mean, we’re talking … I’m barely starting my freshman year of high school, and selling these sneakers for times 3, times 4 their price. Like $1,500. $2,000.
Sherry Walling:Those are nice margins.
LaTesha:Yeah, huge margins. You know, so I kind of ran into something just out of my own curiosity.
Sherry Walling:I assume you didn’t just sell your own shoes for your business, but how did you scale it up to the next level? Or what in you made you think, “Huh, this is a system that’s working, how can I take this up a notch?”
LaTesha:Yeah, so what I did was really just kept flipping it like that. So I took the profit from those initial 12 pair, and I remember exactly it was 12 pair. And I probably remember each of the sneakers as well in that 12. And I took the profit from those 12 pair, and I told my mom to take me … If you lived in Army family, then you know about the PX, the BX. I told her, “Can you take me to the PSBX? I sold some sneakers.” And at this point, she was like, “You did what? I don’t understand.” Because she would have to cash the money orders, because there was no merchant accounts at this time. So, I would give her the money orders, can you cash these? I need you to ship these shoes out for me. And then we need to buy 24 pairs this time.
 And then I’d put them on the website, and people would do the same thing. Send me a money order, all the way to Okinawa, Japan, and I could send you to that, until we eventually moved to North Carolina. So I did my sophomore, junior, senior year in the Raleigh, North Carolina area. And from that point, that’s when I was able to kind of … I don’t know if you want to call it upgrade the website, but continue to scale it. And learn new technologies. And eventually take it to a multi-million dollar business.
Sherry Walling:Is that when you learned how to build a website?
LaTesha:I did. I don’t know if you want to call it a website, because it was FrontPage. Microsoft had FrontPage, and they allowed you to piece together a site. And so, we went from a line of sneakers with a “Please send your money order here,” to a website on FrontPage with more sneakers. One page still, but with a buy button, which just sent it to a contact form. So now I was getting an email. Before, I was just getting random money orders. There was no contact. I didn’t have a email, there was no Gmail, there was no Hotmail, at that time. So, it was just people sending me random money orders to Okinawa, Japan. And then that got upgraded to a buy button, that sent me an email. And then I told them where to send the PayPal, or the check. And then, again, my mom had to cash it.
Sherry Walling:So, not quite the streamlined business you’ve got going on now.
LaTesha:Nope. Nope.
Sherry Walling:But that’s what it means to be an early adopter, right?
LaTesha:Yeah. Yeah. It was really exciting times. Especially because I didn’t really know anything about having a niche, or … I thought everybody loved sneakers as much as I did, you know? I didn’t know that this was a very specific thing. It was a culture behind it. So, yeah. It was super exciting.
Sherry Walling:What was it like to have a million dollar business before you graduated from high school? Or right as you were in that area of your life? 17, 18?
LaTesha:I felt like it was … It was very different, while other kids were thinking about partying, I had this thing that I couldn’t really share. I couldn’t really relate. I had nobody to really talk to about this. I felt like that was, 14, 15, 16, going on 30, so to say, in my mind. Because I was always focused on being the best. Making money. And not thinking about partying, or whatever you do at 14, 15, 16. Not getting a job. Wasn’t really thinking about what’s the next party? And so, that even carried on into college as well. I felt like I was an outcast, so to saying. Because I had these things that I didn’t really share. I couldn’t relate, so to say. And we didn’t grow up in a family of money. We grew up very poor. I say poor, but it just depends on the section of my life we’re talking about. Because I know if my mom heard this podcast, she’d be like, “We didn’t grow up poor.” But we grew up poor in a certain aspect of a time frame in my life.
Sherry Walling:You have memories of feeling like there wasn’t enough money or resources to go around, really.
LaTesha:I never felt like that. I didn’t know that when I lived with my Grandma, that we lived in the projects. And that we were poor. Because she never made us feel like that. She always made us feel like what we have is what everybody has. You know? Because we didn’t travel. We didn’t go out to the beaches. We didn’t, I guess, live a more privileged life, the way my sons do today. I didn’t know any better. So I didn’t know that there was a lack of resource, so to say, if that makes sense.
Sherry Walling:Did you know any entrepreneurs when you were growing up?
LaTesha:[inaudible 00:10:35] entrepreneurs …
Sherry Walling:Or people who ran their own businesses, like … I mean, it seems like a sort of an unusual thing, as a young woman, to be like, “I’m gonna sell my sneakers, and make lots of money.”
LaTesha:I didn’t.
Sherry Walling:Where’d you get that idea?
LaTesha:From a very young age, my mom said … Since I’ve been small, she said all I’ve wanted to do was have a business, or sell something. Or sell somebody something. She just said that I just knew that I was gonna own the world one day. And she said it’s funny, because it’s a different from what she was guiding me towards, which was … She taught me a lot about entrepreneurship, once she saw that I was interested, but she doesn’t have, really, an entrepreneurial background, in terms of having ever owned her own business. But she always taught me to be independent. And if you want this kind of lifestyle, you gotta kind of make it happen. But there was really no entrepreneurial influence in my life.
 She just said that once I got the bug … Once I sold my first thing, that that’s all I wanted to do. I wanted to wash people’s cars. I wanted to mow their lawns. I wanted to sell them candy. I wanted to … In college, sold Blacks in my dorms. And Blacks are like cigarettes that people smoke. I went to Sam’s Club, and just bought a pack of them. And people would come knock on door, all times of night. And there was really no, I would say, early on, other than my mom showing me the basic profit and loss. And how you make a basic run from a foundational standpoint.
Sherry Walling:It sounds like, your mom was a really important figure, obviously, growing up. Most of our moms have played a pretty important role in our lives. You talk about some of the values that she instilled in you. This sense of independence, and I gotta imagine, hard work. Just knowing how much hustle you’ve had to have to built what you’ve done. Yeah. Were there other values that you think you got from your mom that have shaped who you are now?
LaTesha:Yeah. As a young adult, definitely learned hustle, independence, work habits, from my mom. She worked 80, 100 hour week, as a manager. So she worked a lot, a lot of hours, and so she always instilled into me and my brother that if you don’t want to do this … Which is funny, because as a entrepreneur, you kinda … There’s no balance of life and business, I feel. Even though people want to say work/life balance, it’s really, really hard. Yeah, so she really instilled into us, if you don’t want to be under somebody’s control, so to say, if you want to build your own life, you want to have your own things, then you really need to work hard. And you really need to hustle. And you need to be educated. Because she grew up in a family that was not educated, so that was really, really important to her.
Sherry Walling:So, in a way, she’s preparing you to launch to the next kind of economic level, past where she was able to get.
LaTesha:See, I think that’s the greatest thing that she was able to give me and my brothers, seeing that she wasn’t gonna have this big, successful business. So kind of laying the foundation and the path for us to have it.
Sherry Walling:Because she wanted to set you up to be as successful as you could be.
LaTesha:Right.
Sherry Walling:How does she feel about all you’ve accomplished at this point?
LaTesha:She’s very proud. I mean, we’re at the beach right now, and I’m telling her I’m getting ready to do an interview. And I haven’t seen her in two years, so I brought her down here to the beach. She’s always like, “Wow, I’m super super proud of you, and what you were able to accomplish.”
Sherry Walling:Is your dad in the picture at all? Was he a part of your growing up experience?
LaTesha:My dad was in the Air Force, so he definitely was in the picture, in and out. Because he was deployed a lot. So, I have memories of him, earlier in life, but not really in shaping, I feel, like anything entrepreneurial-wise. He was just like more the … I don’t know. The strong hand, the discipline-er, but not a man of many words. Just one to try to … I don’t know. It’s very strange, my memories of him. Because I feel like he was in the military, and most of my memories that I have of my father are just ones of … I was very unsure about him, because in public, he was very happy. But behind closed doors, he had, to me, characteristics of being abusive. And being narcissistic. So I think that definitely played a role of me being very shy, and kind of in my shell, and not trying to upset, so to say, him.
Sherry Walling:You wanted to be able to keep a low profile, in case you needed to. In case he was upset.
LaTesha:Yeah.
Sherry Walling:And he tolerated your independence?
LaTesha:Yeah. Again, he wasn’t really … I don’t remember him being … I feel like he was supportive, and he would come to the things if I had something. He would take me there. But he wasn’t a man of many words. You know? When you did something successful, or when you did something that you maybe needed more coaching on. He was just very like … When it was something you mess up on, he was just very, very strict. But I don’t know how to really describe the dynamic. It was one of understanding without many words.
Sherry Walling:So not necessarily a lot of warmth, or conversation, but he’ll show up. He’ll drive you to things. He’ll sort of do the tasks that need to be done.
LaTesha:Exactly. Exactly.
Sherry Walling:So one of the things that it sounds like you’re involved with now is some funding, and venture capital, and investing in other entrepreneurs? Do I have that right?
LaTesha:Yes. You do. So, I guess, I never knew what this funding meant. So I’m not like a Anderson [Quartz 00:16:47]… I can’t remember how to pronounce it, so I probably butchered that, so to say. But sometimes there’s little companies or things that I see that maybe just need some seed money. And I’m not even talking about tens of thousands of dollars. Maybe it just needs 10,000, or 20,000, to get some initial traction. So I have my eyes on little investments like that. And then far as myself, OptimizePlayer got an investment from a private equity firm for 3.1 million dollars. But I decided to turn that down, and just run it as more of a lifestyle business.
Sherry Walling:What shaped that decision for you? Why did you do that?
LaTesha:I just don’t think I … One, I don’t think I was prepared. I didn’t even know what that meant. When I got the offer, I was like, yeah, made it! You know? I was so excited. And then when I eventually came back down to Earth, and I thought about what that actually meant, it really just meant that I was going to owe somebody some … A return. And in exchange for building a business. And to me, that sounded like a lot of nights of stress. Because there was no money on the table, for cash, there was no sunset money, as Rob likes to call it. There was no life changing type deal. It was just, we’re making an investment to your company, to use it to hire more resources, and to get it to that next level, so to say. And so, to me, it just sounded like a lot of sleepless nights. Because when you write me a check, I’m thinking, and I’m assuming that you’re expecting three to five times back, or maybe more, for that money. Then, to me, I’m indebted to you. So that didn’t really … The terms didn’t set well with me.
Sherry Walling:You didn’t want to do it that way.
LaTesha:Yeah. Yeah. That sounded like prison to me, more than freedom. And I made it type of thing.
Sherry Walling:I know a lot of people who would have the same perspective. Have you had mentors in your life, that have helped you kind of navigate the world of start ups, and funding, and entrepreneurship?
LaTesha:No, I have not. But that’s the reason why I’ve mentioned that I think what’s next for me is starting to get out of my shell, and realizing that people are not here to judge you. They’re here to lend a helping hand. People like Justin Jackson. I’ve met a lot of people at Microcom. I’ve been asked to speak many times, but because I’m so, so timid, that just terrifies me. I’ve made up excuses, not to do it. Like, oh, I can’t. I’m not able to come speak, I have something planned that week. When I didn’t. So, I think my mentorship has come through just small meetings. Through people who have bought my software, I have met them. Or somebody has introduced me to them. I have a lot of people in my network that, whether we talk every day, they’re mentorship is in me seeing what they’re doing, and maybe shooting them an email here and there. But I would really, really love to do better in that aspect. And really just trying to meet more people that maybe are not even in technology. Maybe they own a surf shop or something, and I can learn from them. And what they’re doing, in their business, or in their life, and being able to apply those to my life and my business.
Sherry Walling:I think, you know, I’m resonating with part of your story in the sense that I’ve sort of found myself in the entrepreneurial world, also having grown up in an environment where I didn’t know anyone who owned their own business. I hardly knew any women that worked outside the home. Like, just a very specific view of what people did to make money. And then, especially what women were supposed to be doing. So, I think there are certainly those of us who are coming into this world without much concept of, again, the kind of an entrepreneurial life, and what it looks like. And I think voices like yours can be so valuable, because you do come to it with fresh eyes. And without the same set of assumptions, maybe, that everybody else comes to it with. Or people who have more training, and formal experience.
LaTesha:Yeah. Definitely. And I think, too, that I was also embarrassed … Or ashamed, because being a female, when I was 14, 15, 16, and then being a black female. And then being a black gay female, those three things, I didn’t know how to step in front of people. But now I’m very … I’m more comfortable in my skin. I’m very comfortable about who I am, and I don’t try to hide that as much. You know? I remember just going to events with my partner, and introducing her as my friend vs. my partner. So, yeah. I think that being yourself, and then having those mentorships, and telling your stories, is just so important, just in general.
Sherry Walling:Well, I’m excited to see you do it more. I hope the opportunities present themselves, and maybe we’ll see like an attendee talk from you, at Microcom in the next couple years. No pressure.
LaTesha:I was supposed to do one this week … I mean, this time, submit my thing. A few people said, “Are you doing your attendee talk? I didn’t see you on there. Are you …” and I’m like, yeah, yeah. I’m gonna do it. [inaudible 00:22:31].
Sherry Walling:So it’s just ready. It’s now ready for this coming year.
LaTesha:Oh, man. See, now the pressure is on.
Sherry Walling:Yeah, what do you think stands in the way of your putting yourself out there more? I mean, I’ve heard you talk about some of the early life, where it maybe went better for you in your family where you were quiet, and not in the way. And not taking up too much space.
LaTesha:Yeah, I think it’s just … As I said, just being a black gay female, and being … First, it was just being comfortable with myself, and then coming into the business world. You eventually realize that everybody has a story. And that yours is not so bad, or outcast-ish. That’s not a word, but … So I think as I begin to just be myself, and meet people, like Justin, and other great entrepreneurs, like Brian Harris … I mean, there’s just so many that I have met that I keep in touch with. That has allowed me to come out of my shell. But I feel like speaking would be the next thing that really breaks the ice. And then owning my own things. I have been behind the scenes so much, building other people’s great million dollar businesses that I haven’t really just taken time to just realize that I’m capable of also launching businesses. And seeing them through to success as well.
Sherry Walling:Well, I’ve heard some cool things about OptimizePlayer, so it sounds like you’re well on the way to accomplishing that as well.
LaTesha:I believe so. So, I’m coming around.
Sherry Walling:One of the things that I feel like I hear over and over in these conversations, when I talk to founders from all kinds of walks of life, and all kinds of different businesses, and level of financial success, there does seem to be this common trend of isolation. Like, I imagine you, at 14, 15, and 16, everyone else is thinking about way different things, and you’re thinking about how do I maximize my sneaker business. I think the aloneness is almost the thing that makes you not alone. So many founders have that similar experience of like, I was just on my own. I was doing my own deal. I wasn’t doing what everyone else was doing, or thinking about when I was a teenager, especially.
LaTesha:Yep. And that’s exactly how I felt. Just very alone in my own way. And just not really able to relate on other things. But you know what? I tried to fake like, yeah, that sounds cool. Let’s go do that, and fit in. And stuff like that. But really, I was just always thinking about business, and how I was gonna have … Buy that big house, drive that fancy car. Take care of my family.
Sherry Walling:Have you arrived?
LaTesha:No. I don’t think that I have arrived. I think, what I’m learning right now, is trying to learn what makes me happy. And I feel like I’ve failed at that. Chasing the wrong things, having had success so early. So I think that I’m in … I don’t know, we’ll call it Tecia 2.0, and that next phase in arrival, you know? So, yeah.
Sherry Walling:Well, very cool. Thanks for taking the time to talk with me. Anything important that we’ve left unsaid?
LaTesha:Probably a lot, but … Yeah.
Sherry Walling:Anything you’re aware of, I guess.
LaTesha:No, I think we covered the basis of everything.