Life After 0-26: How Jordan Knox Rebounded From A Winless Season, Turned Himself Into An Entrepreneur, And Sold His Startup

If you tried to talk to Jordan Knox directly after his freshman season, you most likely wouldn’t even have found him. As he calls it, he was “off the grid” trying to get clarity about what just happened. With all the hopes and expectations of a high school basketball stand out, Jordan went to Division II Academy of Art University, where his team finished the 2010 season without winning a game. That experience began the long journey of Jordan asking himself the tough but important questions about who he wanted to be and what environment would be the best for his development.

Almost a decade later, Jordan will tell you without a doubt that going 0-26 was a good thing for him. It was the catalyst to all the success he would experience as an entrepreneur. As an African-American in tech who has sold a company, Jordan believes in the power his story has to not only inspire, but also help others understand the importance of choosing the right college. In this interview, Jordan talks about overcoming a winless season, why there is no such thing as having two paths, and how he found success in Silicon Valley.

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Talk about your first season of college basketball. Obviously it wasn’t a great start so help us understand who you were back then.

I went to the Academy of Art University my freshmen year. Prior to that I went to Heritage High School in Brentwood. A lot of times this happens when you think you are at the top of your game as a senior and you go play D2 or D1 and it's a hard reality check. Going 0-26 was one of the hardest things I’ve had to overcome in my life. Einstein has this famous quote. “Anyone who has never made a mistake has never tried anything new.” And basically going 0-26 reflected that I tried to go to a different university and program than my peers and it didn’t work out.

How did the 0-26 season affect you?

I went off the grid the day after the season. I did not go to class, nor did I speak to family and friends. I utilized my time to get a sense of clarity around what I could control and what I wanted. I knew I could not go lower than 0-26, so what I needed to do was find some seeded opportunity in that light. I gained clarity by picking up the practice of meditation. Meditation wasn’t as well known as it is today, but it helped me cope with the social pressures that I experienced as a freshman. I was embarrassed to tell my friends I did not win one game in my freshman year of college basketball.

What did meditation teach you or help you realize about that first season that maybe was hard to internalize in the moment?

Meditation taught me how to bring my focus to the present moment rather than focusing on the outcome. Training my mind really helped me get through the turbulence. Many athletes don’t understand the importance of training their mind. Yes it’s important to jump higher. It’s important to run quicker. Yes it’s important to be physically strong. But at the end of the day, if you can create that space within your own mind which means paying attention to the present moment, you could shut down a lot of those distractions that at the end of the day don’t matter. I started to learn once you see things are how they are, without judgement, there’s a sense of oneness and peace with whatever situation you are experiencing.

Going 0-26 helped me realize that success really doesn’t depend on winning. Winning to me was defined by the way it feels to be who I am. I realized halfway through the season that it’s really about process and enjoying the small things which are a byproduct of playing the game of basketball. Meditation was my secret to diffuse the negative intensity of having a winless season.

Why transfer after the 0-26 season instead of growing at that school?

I chose a school based upon my finite views about what I thought was important at the time–which was getting playing time. Despite going 0-26, the number one reason I decided to transfer wasn’t because we didn’t win a game. I thought we had a great athletic program even though it was new. Mindfulness helped me be more aware and centered with making decisions. Did I really want to be a multimedia communications major? Did I really want to be a sports broadcaster, at that school? And when I took a look at all the other academic programs at the Academy of Art, I realized I lacked the interest to explore other creative fields. It wasn’t the right academic fit for me.

I should have thought about what that school was known for on the academic side. I should have thought about what type of groups they encouraged athletes or other students to join. I should have been thinking about the most diverse and inclusive university where I can have impact and a voice.

What was the transferring experience like?

It was EXTREMELY difficult for me to get out of ACA. A lot of my credits didn’t transfer to any university. I took two years of general education classes at Las Positas Junior College. I really had to double down and focus on my classes to get 27 credits in two semesters while playing basketball. If I were to stay I would have had a very easy next set of three years at that school. Since I felt some tension in leaving, and a sense of evolution, I knew I was on the right path, despite the uphill battle it was.

How do you reflect on the move given the uphill battle that transferring was? Did the move justify leaving ACA?

I live by this quote that I made up by myself [laughs]. “If your life does not look like a third graders scribbles you’re on the wrong path.” I don’t believe in the classic “Take the path that’s less taken” quote. There’s no such thing as just having two paths because we are faced with different decisions and choices every single day. I had to be very close to my intuition and what that meant was practicing meditation to understand what my gut was telling me despite how bad it looked from an external perspective. As long as you feel that it's right, you are staying true to who you are, and that a decision aligns with your values, I feel you will always find success.

You eventually transferred again to a Division I program. What was it like attending your third school?

I didn’t have a breakout season at Los Positas. It was decent enough to capture the attention of the coaches at California State Fullerton University. When I was assessing my options, on where to go to after LP, there were no top three reasons why I chose CSUF. There wasn’t a checklist. And most students have that. They say they need the school to be a party school or they need this school to be close to the beach. Again, for me it was about channeling that energy internally and getting clarity on where I wanted my next move to be. In that moment I knew I wanted to leave the Bay Area, but not too far where I risked the connection with my family.

While you were playing, you became more interested in entrepreneurship. Where did that interest come from?

I felt I could have a much bigger impact in entrepreneurship than sports because I’m African-American. There was and still is a lack of people of color in Silicon Valley. The problem is both complex and cyclical, and the industry reliably fails to attract, cultivate, and promote ethnic equality. This was a huge topic of concern for me, and I knew early on that true inclusion will only happen when underrepresented groups accrue power in tech. I saw entrepreneurship as an opportunity to open doors for people of color in one of the fastest-growing and highest paying sectors of the economy. This in itself was inspiring. I wanted to take transformative steps towards widening the circle of inclusive growth. Ultimately, it was up to me to decide how I defined my why. It’s not always easy, but I find that pinpointing your purpose can be a rewarding undertaking.

My burning desire to start a company was around the time that Facebook was becoming more and more mainstream. Instead of being the last one in the gym or the first one in the gym, I found myself spending more of my time reading tech articles, reading about founders, learning about how to build tech products, and talking to friends at tech companies. I was so passionate about the game, but my curiosity was literally screaming in my face. It got to the point where I would drive to Palo Alto literally to buy people coffee who work in tech to ask them what they did and if there was something they could teach me.

So you’re playing basketball and immersing yourself in tech. How did you channel that energy in the right direction?

I challenged myself to create something that I would use. At the time that was a social network for athletes called Rpass. I literally tried to re-create Facebook, but for athletes. The idea was to give athletes digital points they would earn by posting uplifting content in exchange for redeemable gifts. I pitched the idea to my neighbor, Donovan, who gave me $25K to develop the platform. I knew nothing about how to do this, but I wanted to test how far my curiosity could take me.

Where did it go from there?

A few months later I launched Rpass to 400-500 student-athletes. It was such a gratifying experience because I knew this was the start to something outside of basketball. It caught the attention of my uncle, Abdul, who was also my trainer. He trained Serena Williams and many Silicon Valley tech professionals. When I told him my dreams of breaking  into into Silicon Valley, he literally took me under his wing. It was one of those Rocky Balboa and Mickey Goldmill moments. Funny enough, he was actually the first one to tell me that Rpass was going to be a flop, but he knew that people wanted to see young African-American men and women have impact in the world. He knew there was a lack of workforce diversity and unconscious bias in the Valley.

One of the people he introduced me to was Patrick Gannon, one of the founding members at Lending Club. When I was pitching Rpass to Patrick, I thought he was surely going to invest. When he asked me simple questions like–what RPass was, why I was building it, and what problem I was solving–it took me 45-minutes to explain it to him. By the end of the call I was jumping for joy.

So Abdul called me and tells me “okay he’s not going to invest, but he feels your passion and commitment and he feels like you’re curious to learn more, so he wants to be one of your personal mentors.” Patrick and Abdul were the two people, outside of my parents, that had this personal interest in my growth. I was too far to turn back, and was held accountable from the jump. The feeling was like, if you’re in, you have to be two feet in. If you’re not, then get off the ship now because there is no turning back.

What did Patrick help you learn?

He showed me how to properly raise a round of funding, what it means to validate a problem in the market, and how to then design a very minimum viable product to solve it. All of these basic questions that a first time entrepreneur would have, Patrick answered them while giving me the guidance and opening the door for other opportunities.

Can you talk about the importance in having Patrick and Abdul as mentors as you transitioned away from basketball.

I learned a ton from Patrick and Abdul, but I’ll try to boil down what I learned to three things. The first: make something that people love, and if you do that then the goal is to figure out how to get more people paying or using it. The second is that you need a collection of things: a great idea, team, product, and most importantly the ability to execute. Often times what founders get wrong - and this was the mistake I made while building Rpass - is being able to answer the question of why. Why am I building this? I couldn’t answer it in a clear and concise way. Patrick taught me was that this is how you get evaluated as a founder.

The third thing that I learned is that it's really important to learn who desperately needs your product. In the ideal world you are the target user. That itself was what led me to build Crux with my best friend, Juan Carlos. Crux was a college group messaging app that allowed people to group chat using threads (like Slack). I knew from personal experience communication on basketball teams was terrible, and Juan Carlos had many friends in college that also resonated with the problem. Texting in single chat threads was horrific. You lose topics in messages and it was a huge waste of time trying to stay organized. I was the ideal user and this helped me better understand that there are thousands of others in the country that have the same problem.

I had Abdul and Patrick, but I also had my family as support. The moment I told them I didn’t want to play basketball after my senior year, it really helped them learn new ways to support me. From my dad, mom, my sisters Kiah and Kourtney, my girlfriend Keani to my best friend Juan Carlos, I see them as my mentors. They were my starting five and they helped me win at the end of the day.

Did any of those lessons take you longer to learn?

When I started Crux with Juan Carlos, we didn’t really understand how to create culture. We really didn’t know how to build that blueprint for building a collaborative environment. We also learned the importance of having process. It’s not about speed, but efficiency. It’s about efficiency in how you communicate and put the right tools in place to empower your employees to work in the most effective way possible. We really underestimated the importance of those two skill sets.

How did not understanding the importance of culture affect your growth at Crux and development as a founder?

Internal communication can make or break your startup. Like when you’re having fundraising problems, what do or do you not tell employees? When you’re about to run out of capital, who is on that information? And if you don’t communicate that appropriately, bad things just happen.

When our runway was dwindling we could have done a better job at communicating the fundraising process to our team. Eventually, we raised enough to give us more runway, but we got to a point where we knew we didn’t have product market fit. Rather than communicating this and sharing this information, we held on to it. It wasn’t about alarming people and telling them we were scared. It was about making sure we could get everyone on the same page and communicating the options we had.

GOING 0-26 HELPED ME REALIZE THAT SUCCESS REALLY DOESN’T DEPEND ON WINNING. WINNING TO ME WAS DEFINED BY THE WAY IT FEELS TO BE WHO I AM. I REALIZED HALFWAY THROUGH THE SEASON THAT IT’S REALLY ABOUT PROCESS AND ENJOYING THE SMALL THINGS WHICH ARE A BYPRODUCT OF PLAYING THE GAME OF BASKETBALL.

And how did you right the ship from there?

We pivoted out of the college market to create a chatbot for employees to find information about their company. Imagine a Slack bot that lives in Slack that can find you any files within your organization, no matter if it is in Dropbox or another storage system. We pitched that idea to Phil Libin at General Catalyst. He told us his friend, Jack, an ex-VP of Product at Evernote, was trying to solve a similar problem and that we should chat. After my co-founder and I met with Jack four times in one day, we decided to work together and started Butter.ai.

Tell us about Butter.ai, which was essentially your third company.

Butter.ai was a natural language search platform that helped employees find the right documents across the majority of productivity tools like Trello, Asana or Slack. We raised $3.2 million dollars from institutional and angel investors. To sum up those two years, we had good press and an uptick in users, but our engagement wasn’t that great. We didn’t really have product market fit because people weren’t using it everyday. We realized that because people weren’t coming back a lot, the tool on its own was more valuable as part of a broader product.

In addition to getting the product right you were still addressing culture issues. As a company, how did you deal with these challenges and the feeling of not being where you wanted to be?

Juan Carlos, Jack, Adam, and I all sat down and took our team on an offsite to talk about the hard things like where we were as a company at that time, what our values were, and what type of culture we wanted to have. It was one of the best weeks of my career because at that moment I knew how important building culture was and establishing lines of communication

Did that offsite result in the change you needed as a founder and company?

We thought continuing to build the product was the best course of action while being open to what else may be out there. Our process was solid and we brought great feedback that helped hone the product into a browser extension, which allowed users to find their information outside of Slack. We had some paying beta customers and it was during that beta period when we were approached about the acquisition from Box. It’s tough to tell if that would’ve made enough of a dent, but what was really happening is that we had started playing in the enterprise search world. We started courting larger customers at that time, but sold when we received an offer out of the blue. Box approached us because they were interested in our company on a deeper level. We chose Box because they were better in line with our vision, mission, technology and culture. So five months after that amazing offsite, we sold Butter.ai to Box. Then, rather than join a big company, I stayed on to help other companies at All Turtles develop their sales processes and just recently joined one of their portfolio companies, Spot, to lead and scale their growth efforts.

Looking back, how did you measure success in all this change?

With this acquisition, I have a narrative that can now spark that same person in college and high school to not just think about life after sports. You can't play basketball forever. Even Kobe Bryant had to think about it. I have a story that will help people incrementally raise that inner voice and awareness to find that thing that they are passionate about. I have a story that can allow people to be curious about other parts of their own world. If not to be an entrepreneur, I can bring more focus in helping someone double down on their athletic career to help them actually choose the right university. Having that story as an instrument to inspire is what’s most important to me.

And what did success mean for you as a founder and your team?

I measure success also from the standpoint of my team, investors, and family. For my team, despite the finite outcome (we won and sold a company), success is being able to remain best friends and stay very close. Our team still operates with that sense of trust and integrity and we talk about things that aren’t work related when we do meet up. For our investors, they wanted to win. It wasn’t just the financial return, but the investment in really helping their founders and people in the company grow.

And the last one is seeing my family happy for me. Despite some incremental success, they still challenge me. Even though my team got acquired, they are still like…okay great, so what’s next? They’re pushing me to reflect on the teaching points I’ve learned over the last two years and apply them to my next endeavor. Success for my family is knowing that I’m not making the same mistakes twice, and I’m raising that bar for them and myself. What I accomplished going from 0-26 to getting my startup acquired, they said it expanded their minds on what they thought they could do too.

I FELT I COULD HAVE A MUCH BIGGER IMPACT IN ENTREPRENEURSHIP THAN SPORTS BECAUSE I’M AFRICAN-AMERICAN. THERE WAS AND STILL IS A LACK OF PEOPLE OF COLOR IN SILICON VALLEY. THE PROBLEM IS BOTH COMPLEX AND CYCLICAL, AND THE INDUSTRY RELIABLY FAILS TO ATTRACT, CULTIVATE, AND PROMOTE ETHNIC EQUALITY. THIS WAS A HUGE TOPIC OF CONCERN FOR ME, AND I KNEW EARLY ON THAT TRUE INCLUSION WILL ONLY HAPPEN WHEN UNDERREPRESENTED GROUPS ACCRUE POWER IN TECH.

What are you most proud of in your transition away from basketball?

When I was starting Crux, I was staying at Juan Carlos’ house for almost a year. I couldn’t even afford a gym membership. JC’s mom was making us breakfast, lunch, and dinner everyday because she knew we were in this together. My girlfriend initially did not really understand the day-to-day aspects of starting a business, but she understood that I needed a best friend to communicate freely with to escape. I appreciate how my mom and my dad never questioned my decision to start my entrepreneurship journey. They would always help me understand the consequences and how I would have to own up to those. And my two sisters were there to talk through the emotional rollercoaster problems that you don’t see in founders everyday. JC was like a mentor for me coming out of college. We had nothing in common, but we decided to team up because our skill sets complimented each other extremely well. And it was a journey! We would travel to colleges and universities - like from Orange County to San Diego for example - and we went through flat tires midway there.

We used to drive up on the i5 to meet with an investor only to have them cancel on us when we were halfway up there. So there’s that feeling of knowing that I have an incredible teammate and by default an exceptional team. The characteristics that I would tell anyone when it comes to finding their own founder is find someone you can trust, is determined to get shit done, and has a sense of resourcefulness. It’s not just the resources to achieve the desired business outcome, but the resources that you can use to grow and evolve as a person. Juan Carlos was that for me.

I would have never thought that my relatives, family, friends and partner would have this much impact on accelerating the time it took me to get me to where I’m at today. If it wasn’t for the people who initially believed in me, my foot would be off the gas pedal and the car would have driven off a cliff. It’s important to assess the market, have a good idea and validate a problem, but having that support system helped me 10x my capabilities and resources to get things done. That’s what I’m most proud of.

Looking back, why would you say athletes make great entrepreneurs?

I think there are two different types of athletes. Finite and infinite athletes. Finite athletes just focus on surviving day to day. It’s about doing what they have to do to get a win. I feel like infinite athletes are the ones that understand that their team is no less than a collection of people that are playing an infinite game together. These principles of playing in the infinite game are transferable to what it means to be a great entrepreneur. Infinite athletes are dedicated not just to their own success but to their team, trainer, water boy, fans..they trust everyone’s intentions and are not afraid of conflict. They can set and measure goals and results. And these were the things that I realized actually make a great entrepreneur.