I came from a middle-class family where we always had enough, but nothing more. My parents always put me in the best schools, where I had very wealthy friends who seemingly had everything they wanted, and their parents always owned their own businesses. I think that’s what led me to always want to be an entrepreneur – not just the potential money, but more importantly, that feeling of having built something that you could say was your own.
I’ve been selling things to people since I was five years old; toys, candy, DVDs, even charging kids to clear their browsing history, back when the internet first became a thing. That fire to hustle has been in my belly since I could walk.
Why did you start your business(es)?
The easy answer: I love sports and technology, so I found a way to blend my passions together. The tougher answer probably is, I’m unemployable. A 9-to-5 job, in a cubicle isn’t for me. And luckily I knew that as soon as I got to college. One might say that’s the only thing four years at Penn taught me – what I definitely did not want to do with my life.
What entrepreneur has most inspired you?
There are two people who built the two brands outside of Krossover that mean the most to me; Steve Jobs of Apple and Phil Knight of Nike. I have read both their biographies. I’ve watched all their speeches. I truly love their brands and their products. When Steve died, I went and stood outside an Apple store and cried. I Never met the man, but his vision changed the world.
I’ve been in a room with Phil Knight before and saw the man cry when one of his long-time employees gave a speech. If there’s one man I could sit down to lunch with in this world, to tell him how much I appreciate what he’s done to inspire me, it would be Phil Knight (and then I’d ask him if Michael Jordan could join us).
What is the biggest obstacle you have overcome thus far in business?
Letting people go never gets easier, but learning to fire people who are no longer right for the role is something that has to be taken seriously. A company is just a collection of people, and if you have the wrong people, you will be in big trouble. The easiest thing to do is to just assume things will eventually fix themselves. But, the reality is, it’s incredibly important to move quickly and bring in people that can get the job done.
What have you learned from failure?
Life goes on. There’s really no point dwelling on anything that goes wrong. Make sure you make a note to fix whatever the problem was, put your chin up, and keep moving forward. Nobody has gone through life without failing at something – most of us fail at something every single day.
Being a husband, a friend, a daughter, a coach, a player. Heck, plenty of people these days in the world fail at just being a decent human being. Accept failure. In fact, embrace it as something that is inevitable, and as something that will make you stronger. The best part about being an athlete is you understand that feeling of failure and losing – and it makes you want nothing more than to try harder to win.
How does your leadership style foster your company’s culture?
Some may see me as too hands off, but my motto has always been, to tell people why they need to do something, but not how. I’ll give you the vision and the rationale, but I expect you to figure out how to get the job done. If you can’t, then this isn’t the place for you.
As a result, I think we’ve created a great culture where we hire fast, and fire fast, but at the same time, give those who pass the test, an incredible sense of independence and responsibility. Krossover employees feel empowered to make decisions and execute on them. We push people to act first, and ask for forgiveness later.
What are your top 3 responsibilities as a leader?
The only thing I’m good for at this point, is to hire great people, keep them happy and motivated about the grand vision, and ensure that everyone is getting paid on time. The rest is on the team to execute.
What internal process do you use to guide your decision-making?
I try to be as data driven as possible. If someone wants to go down a certain path, they need to show me data that explains why. If you don’t have data, and only have an opinion, then we’re going with my opinion!
How do you define success?
Success is being able to make a living doing something you love, so you don’t feel like you’ve worked a day in your life. I have two such jobs now, running Krossover and making investments as a VC at Courtside Ventures.
Which book has inspired you?
When Breath Becomes Air by Paul Kalanithi and Chasing Daylight by Eugene O’Kelly are two incredible books written by two high-achieving people that were facing imminent death, due to terminal illnesses. The books are a true reminder of all that is actually important in this world, and the little things really don’t matter. It’s hard not to read those books, cry, and then get off your ass and do something great, with the time you have left on this earth.
What do you think is the coolest technology out there, and why?
Despite being a technology, new gadget addict, I still think the coolest tech out there is man’s ability to fly. To think that we can sit in a seat and be airborne, relatively safely, and land at our destination thousands of miles away in a matter of hours is absolutely incredible. While iPhones and VR glasses are neat, what’s cooler than sending a man to the moon?