Tips From The Top: One On One With AJ Vaynerchuk

I spoke to AJ Vaynerchuk, co-founder of VaynerSports and VaynerMedia, about his journey and best advice

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Adam: Readers will want to know more about you. What is something about you that would surprise people?

AJ: I love horrible television. All in on shows like Survivor, Bachelor, Bachelorette. I first got into that type of TV because it was a good distraction away from how I spent the majority of my day. My entire day at VM was full of critical thinking and it was nice to put on something that would melt my brain away.

Adam: I am asked all the time about what it is like to work with my brother. How is working with yours?

AJ: Me and my brother have an unbelievable working relationship. I think we’re very fortunate in that we share a lot of viewpoints and we’ve developed a really good ability to communicate with each other so that if we do disagree about something, it can be thoughtful. Even if it gets emotional at times, we try our best to keep it under control. We’ve never in business had a real fight—only times we fight is over a board game or sports.

Adam: Describe the journey you and Gary have been on. How did you get here? What are some of the failures, setbacks, or challenges have been most instrumental to your growth?

AJ: Gary and I first started working together through an eBay-flipping business—we would go to garage sales on weekends and Gary would bankroll our purchases—I would spend the rest of the weekend posting stuff on eBay and selling it. I’m a big advocate of learning business that way. It’s a great way to understand sales, marketing, supply & demand, the market in general, customer service, logistics, finance, etc. Then we started VaynerMedia after I got out of college. That was a great success—a real rollercoaster growing a company that fast from a few people to 500+ people in 5-6 years. The entire journey has been just fantastic, it’s been successful and we never fight so it’s been wonderful frankly.

Adam: What have you learned from your experience investing in early stage companies?

AJ: One of my biggest beliefs is that opportunity exists where people don’t see it. If everyone believes that something is going to be successful, then there’s probably something that will dilute it. I think we underestimate what society is willing to do. Some of my best investments came a while ago. When I invested in Uber, the concept of using your phone for a taxi when taxis were already on the street didn’t make sense. Venmo was an early invest — why would anyone text money or send money to one another over an app. It’s all about execution. There’s a lot of great ideas and someone who’s an operator may hear an idea may gravitate towards it because they know themselves how they would make it happen. But ultimately as an investor, you’re not an active member of that company so really understanding the entrepreneur and the founding team and ensuring they’re the right ones to execute that idea is most important.

Adam: What advice do you have for entrepreneurs interested in pursuing business opportunities in sports? What are some of the similarities and differences relative to other industries you have been involved in?

AJ: Number one piece of advice is patience. Sports is a highly competitive field, it’s one of the major hobbies and pastimes of our society so with that comes a lot of competition and restricted opportunities. I’m someone who chased their dream job in sports after their first career. I didn’t come out of school and get right into sports— I took a different path. I think patience is the biggest piece. Business is business, there has been a lot that I’ve learned at VM that has applied at VaynerSports. As far as differences go, there is a difference in the product, servicing an individual as opposed to servicing a Fortune 500 company is obviously a completely different role. Sports is a results-based business—a lot of the opportunity for an individual athlete comes from their own performance on the field. The more the athlete performs on the field, the more marketing opportunities exist, the more business opportunities come up. There is a black and white correlation between on-field performance and opportunities off the field.

Adam: What are your three best tips applicable to entrepreneurs, executives, and civic leaders?

AJ: Communication — I think naturally humans are afraid to communicate the hard conversations. If you’re an entrepreneur, you need to have the willingness to have the tough conversations because having the tough conversation early on serves you so much better than waiting or burying your head in the sand.

Patience — People have asked me why VaynerSports hasn’t ventured out into a different sport. My answer to them is that I want to make sure our football practice is fantastic before branching out because spreading ourselves thin and never doing anything really great is a real fear of mine. Having patience, understanding when’s the right time to expand, when the right time to take on a new opportunity is a key skill. More often than not, most people take on new opportunities faster than they should.

Relationships — Building relationships is key in any business. You’ll never make big things happen just by sitting behind a keyboard. Being out there, developing relationships, attending the right events, and understand the blend of emailing them but also being out there is key.

Adam: What is the single best piece of advice you have ever received?

AJ: From Gary about perspective. Being able to take a step back and understand that nothing is ever as bad as it seems and nothing is as great as it seems—keeping an even-keel. Personally for me, I’ve dealt with health issues, specifically Krohn’s disease, so understanding perspective helps when dealing with my personal issues or my business issues. I count myself as very fortunate and having that ability to tap into that self-awareness of gratitude for the situation that I was born into and was set up to have and really set me up to succeed is key. Being self-aware and having perspective and ultimately never getting too high and never too low is the best advice I ever got.

Adam: What is one thing everyone should be doing to pay it forward?

AJ: Being generous with your time. Our society has a very easy time in asking people for their time because they think it doesn’t cost them anything but sometimes time is the most valuable asset. Something I try to do the best I can and that everybody should try to do, is recognize that when someone reaches out, giving back, because you were in that position one day where you reached out and someone helped you out. So giving back with your time and perspective is something I think everybody should be doing.

Adam: What are your hobbies and how have they shaped you?

AJ: Playing golf. Playing basketball two times a week. Sports is such a big part of my world. When the weather allows, I try to golf as much as possible. It’s not an accident that my business is in sports. I think in general, I just love being outside/active when I’m doing my hobbies. Both basketball and golf are somethings you can practice by yourself—something I’m a fan of is putting in the work and seeing the results. In my nature, I have a real work ethic and I think my hobbies correlate to both my passion for sports and my fulfillment of activity and also practice & being a results-based personality.

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