Win-Win has a strong focus on social impact and nonprofits. Why did you go this direction with the business?
One of the things that often gets lost in my story is that I am—and have always been—a philanthropist. My mom made giving back a very important part of my early childhood. We were always helping to feed the homeless, serve meals, and donate clothes. She made it a point in showing us kids that we can always give to somebody in need.
I started a nonprofit with one of my best friends while I was playing football, and I saw how hard it was to fundraise. I also saw all of the opportunities being thrown at celebrities and influencers to support causes and brands, and I realized there was inefficiency all around. I was in a unique position to know what nonprofits needed and what it takes to get influencers engaged in a meaningful way. I feel like I made it here for a reason and that I should leverage whatever platform or influence I have to do good.
You started with a career in the NFL. What inspired you to jump into the startup world?
To start, it’s important to know that I had zero experience or understanding of tech and startups—how they work or even what they were. I was first introduced to this whole world while finishing my professional football career. There were always guys in the locker room talking about what they were putting their money into, like franchises, and what they would do after football.
I always had a business mindset and I thought I should go to business school and get my MBA. I was on that track when my friend told me about Draper University. I didn’t know anything about it or the tech industry, but I applied (I actually applied after the deadline) and I was totally apprehensive about the whole thing; I didn’t know anything about the Bay Area and I had my mind set on the more traditional business school route. I actually decided that if I got in, I would probably decline. And then I got a call from Tim Draper himself. Tim really helped me understand the opportunity, so I went.
What was it like moving to the Bay Area and starting this new career path?
Looking back, it feels like a blur. There was so much information and knowledge shared. One huge benefit of being a part of Draper University was access to other founders. We had about 3-4 speakers a day, usually founders from companies that had successfully been acquired or were in the middle of a Series A raise (at the time, I had no idea what that meant), so it was all one big “aha moment” for me—everything was completely new.
I literally came away from every session with a founder thinking: “This kid right here created that?! That’s incredible!” It was eye-opening to me and I knew this is what I wanted to do.
What was it like teaching yourself to code? Any tips for readers?
When I realized I wanted to get into tech, I knew I wanted to get into it for real—not just to play—so I wanted the respectability and skills needed to come in for real. It took me roughly nine months studying every day and all day to learn. This was right after Draper University. I had moved back to Houston and there weren’t really any coding bootcamps or anything nearby, so I created my own curriculum. I used a schedule and platforms like Code Academy to figure out the structure. I did a lot of research.
As far as tips, I looked at w3schools and a bunch of YouTube videos. I started by mapping out what languages I wanted to learn, where to start, where to go from there, and I did the research on the frontend to build my own cadence and schedule. For example, I started with HTML and moved to CSS, then Java, then jQuery and Ruby, etc.
There was definitely a time when it was a bit mundane, mostly in the first couple of months, but then I started getting into modules and projects by myself and that’s when the fun started. I remember creating my first website. It was the ugliest thing in the world, but I was so excited. I remember texting a few friends the moment it went live and saying “Yep, that didn’t exist ten minutes ago, and now it does.” To me, it was crazy.
Also, I should be clear that my goal was not to be a developer, but I wanted that skillset. At Draper, I learned that the CTOs of the world don’t really like idea people because the idea people usually have unrealistic expectations; they want something built out a certain way without having a degree of understanding of how it works.
I feel like coding was like a workout I needed to do to be a founder, just as the bench press and squats were workouts for pro athletes.
Do you think your life as a pro athlete prepared you to be a founder?
It 100% prepared me. I was always super diligent with my classwork. I graduated high school with a 4.0; I was on the National Honor Society, team captain, student council—you name it. I went to Duke not just to play ball (although that was a great perk), but I wanted an academic challenge.
I didn’t know it initially, but there were a lot of skills I had been developing my whole life, even going back to little league football. I had to overcome adversity, persevere throughdifferent challenges, learn how to communicate effectively, and build out a team. For example, when I was the captain, I led an 85 person team and every player had a distinct personality and strengths. I needed to know how to get that person to respond in the moment. This all came down to how I was communicating. As I build the team at Win-Win, I’m realizing that I’ve been long trained on this kind of leadership and team building.
You were also a part of 500 Startups. How was that experience?
I was in the 500 Startups Batch 20 (Spring 2017). It was very early days in the company; we were essentially in our beta and had hit our first moment of realizing our business model was not working as we had expected it to, so we were in intense testing and iterating mode.
For example, we really honed in on our user flow and experience, making small tweaks that we believed could make a difference if somebody clicked on and engaged versus dropped off. This was especially critical for our model because we needed people to click to complete the transaction, so we tested like crazy all the way down to the color of the button versus the copy.
In particular, we worked with mentors like Monique Woodard, who was very involved in helping us think through certain models and questions. Clayton Bryan was our dedicated mentor, so we had weekly check-in calls and reports on metrics. He had done a lot of work with influencers and marketing, so his advice was super relevant for what we were trying to accomplish.
When things go south, what keeps you going?
Overall, the #1 thing that’s powered my ability to bust down walls and overcome adversity is my faith. I’m a Christian and I feel that I’m here for a purpose, and I’m living that purpose now. I know nothing worth having is easy, and I’m glad I have this opportunity to learn and grow, even when the journey does not go the way I thought. When things go wrong, I don’t focus on what went wrong, but instead on the learning I’ll get out of the situation.
I also have to credit my family. I got married and had kids relatively early (I had my first kid at 24). This was right in the middle of my decision to jump into tech. It was very hard for me to manage growing my family and my business at the same time—I always joke that I have “two other startups at home.” I feel like I’m building for them. That is my legacy.
What were some of the biggest challenges you’ve faced since launching your business?
To start, I am a solo founder. I realized quickly that I needed to surround myself with the right people to learn from. There are so many blog posts out there with great tips and advice, but you can only extract so much information from these. I knew I needed more data points—more benchmarks for my company’s growth—and I didn’t have a co-founder to bounce ideas off of. So I connected with other founders, in particular ones who were a little ahead of me, so I could get some context and look at data points to know where I should be headed. This has helped me lessen the mistakes.
I’m also a former athlete. Being a former athlete never really occurred to me as potentially having an adverse effect on my startup, but it actually did. It was weird. I noticed I could get a meeting with most people; if a VC found out that I played in the NFL I could easily get early meetings and connections with investors. Sadly, this was usually a waste of time; they didn’t want to invest, but they wanted to ask questions about Peyton Manning and hear stories about me playing pro football. There was a level of me not being taken seriously—the whole “dumb jock” perception was real, and it was something I never aligned with. Even going back to high school, I’ve always been so much more than an athlete. This made me realize that I needed to be more diligent in vetting VCs.
Add this to the fact that I’m a black founder in the tech world, I feel like I’ve had to deal with things that others don’t. I never let this deter me, but it did make it harder in the beginning, especially when I saw my friends who went through Draper get checks for less traction than we had.
What is your superpower?
I’m pretty authentic and am good at building rapport with others. Someone once described this to me: they said I’m good at establishing and maintaining connections with people, and that I’m able to create high-value and authentic relationships. This is probably because I genuinely want to help others. Real recognizes real, you know? By remaining true to who I am, I can build really truthful relationships, which opens doors to collaborations and networks that normally wouldn’t happen.
This is especially helpful to have with Win-Win in terms of influencer engagement and building a team. For example, I raised over $1M in funding without product because I was able to get some of the biggest athletes on board. I’m lucky to have insight and understanding into how to navigate that side of the business.
What’s your kryptonite?
Also relationships. I have trouble investing time in relationships that aren’t mutually beneficial, or where I put a lot of time in developing that relationship when the other person has different motives. I can get burned and worn out from trying to make these kinds of connections happen. I’ve become better at analyzing the situation and using my time more wisely in finding the right relationships, but it’s hard.
What does a typical day look like for you?
It’s pretty intense. As I said, I have two startups at home and a wife. I grew up without my father present and with a working single mother. Because of that, regardless of what I do with my life—whether I’m playing in the NFL, working a nine-to-five job, or running a company—my family and me being present as a father is a top priority. It’s certainly challenging, but I don’t care if I go to bed at 5 am, I’m always going to be up at 7 with the kids and to make breakfast before school.
The second I get into the office, the pace changes, and the work day depends on the season we are in. We are right now focused on fundraising, growing the team, and answering emails upon emails. Once we are in season, we will shift into campaign mode and focus on building relationships with players, teams, and partners.
What's your office environment like?
Our office has just been relocated from Silicon Valley to Houston, TX! We're excited to open our HQ inside The Cannon, which is one of the largest tech workspaces in the world. It's 120K square foot building that will be the home for many early-stage, fast-growing tech startup companies and we're thrilled to have Win-Win be a part of the community.
Do you have any unusual routines or habits?
They ask you these kind of questions all of the time when you play ball, like “what are your rituals or superstitions before a game?” I never had any then, and I still don’t really now. One thing I do, though, is pray. It’s something I’m consistently and constantly doing. I don’t care about perception when it comes to faith and being a founder. I’m Christian—it’s who I am and what I do. I’m praying constantly to have the mental fortitude and bandwidth to manage the ups and downs. I know I can’t control everything that happens in the day, but I can control how I react to things, and my strong foundation in my faith is a major source in helping me handle different parts of my day. Some founders have a routine of meditating, but my routine is praying!
Do you have any other hobbies/things you like to do (outside of sports)?
This goes back to my superpower—I get a thrill out of meeting and becoming friends with really cool people. Not sunglasses in the club cool, but people doing what they love to do—that’s cool. I’ve been fortunate to meet so many people throughout my life, and I get a lot of satisfaction out of connecting cool people with other cool people.
For instance, anytime I meet somebody, I take their number in my phone and save where they are or what city they live in. I then filter my phonebook whenever I travel to see the list of people I’m friends with in that city. I then have this great list of really cool people across industries who are doing what they love, and I can call them up and connect with them wherever I go.
Do you have a favorite gadget or tool you use?
Honestly, I'm not a big gadget guy. The only "gadget" that I really love more than I expected to is the Executive Office Solutions adjustable laptop stand. It's great because it has so many configuration options and I've used it in a number of positions. It helps me keep the grind ongoing! It also has a fan installed that keeps the MacBook Pro cool.
If you could give yourself one piece of advice when you started in tech, what would it be?
It’s always going to take twice as long and cost two times as much. If I had known that when going into this industry, I wouldn’t have been so quick to make certain decisions. We definitely had major learning lessons. For example, I hired ten people right out of the gate and even before we launched. Looking back, this was not the best decision because it took longer than expected to get to where we needed and the ten people were just burning capital. Early founders should take your time and don’t be overly optimistic—you need to have a level of craziness, but keep that dose of reality to realize it's probably not going to work the way you think it is on the first try, and it will probably cost you a bit more.
Quotes you live by. What’s your current quote of the day?
"You either want it or you don't! But more importantly, you're either gonna go get it, or you won't!"
I’ve really lived by this quote, starting from the beginning of this entire journey. Lots of people have ideas. I believe ideas are worth as much as they weigh: nothing. You have to make a decision about whether you want it or not, and if you do want it, you need to be willing to do what it takes to make it happen.