For me, cycling is like floating. In the busy job that I’m in, my mind is constantly racing and thinking about the next thing, but when I’m on my bike I don’t have that. You lose yourself. It feels like being free, like you can go forever. I’ve tried to challenge myself to run more because I hate it, but it’s tiring for me. When I’m riding, though, my legs don’t feel tired, I can just ride and ride and ride. I’ll have that floating sensation, and then all of a sudden I’ll stop and think to myself, ‘Damn, I’ve ridden 50 miles’. It’s effortless.

That said, this past summer I did my first century ride in the Hudson Valley in upstate New York. I’d done the 55-mile race the year before and I knew the 100 was something I wanted to try. I was riding but I wouldn’t say I trained in the lead-up, so it’s probably no surprise that I was toast after 75 miles. My left leg shut down, but thankfully the last 25 miles was mostly downhill. The excitement of the finish helped get me through, I wanted to feel that sense of accomplishment. Plus, I’m competitive. I would have been able to finish for myself, but seeing those other riders stoked a fire in me and drove me to want to beat them to the finish, even with a leg that was giving me grief. 

I loved it, though, and the whole experience changed me - I think endurance events do that. My friend David, who works in our office, ran a marathon and the week after he came back to work I noticed a change in him. It’s like the marathon shocked his system a little bit and he had a different perspective on things. It’s like when you travel and you come back feeling refreshed. I could tell the marathon had that positive effect on David, and the century ride had the same impact on me. I think it’s a mixture of accomplishment, and wondering what else you’re capable of.

One thing I’ve been thinking a lot about is leaning into challenges and adversity and struggle because I know that’s where all the benefits are going to be for me. It’s why I’d like to run more, because I hate it and it’s difficult, but I know it’s good for me. To do that, I think it’s about being present and aware of the challenges, and understanding that if there’s something bubbling up and I don’t feel like doing it, there needs to be a voice to counteract and interpret that feeling. I also want to do another century ride in 2019, and I’d like to take my cycling more seriously and get more regimented about it. I’m never really tracking my time or things of that nature, I use Strava to see my mileage but I would like to get more seriously involved in the sport. I know that means getting the full kit, and probably a new bicycle and getting sized properly and all that fun stuff, but I’m excited to learn about the next level. 

Someone made a comment to me the other week that made me take a step back.

He said: “Andy, you realize you guys are creating history. There’s just not a media team around a person like what you guys have with Gary.”

And it’s really true. Our competitors aren’t other personal brands, our competitors are CNN and Fox News and media companies, because we’re trying to create content on a daily basis around a person and deliver it natively on different platforms and in interesting and smart ways. We’re filming Gary on a daily basis and trying to bring value in a lot of different ways. There’s Fortune 100 CEO’s who take Gary’s advice and there’s people that have been addicted to drugs who take Gary’s advice, so there’s a lot of different demographics and people to consider, and we’re just trying to have fun and bring value to them as much as we can.

Something Gary talks about a lot, and we all struggle with (myself included), is long-term thinking. There’s a lot of things I want to have in my life right now but if I can take a macro step back and consider what I’m actually doing - I’m managing Gary Vaynerchuk’s brand! What is my life going to look like in 20 years time when the whole world can see how this story plays out and I get to say I was at the center of the story since the start?

I think the way you can have that long-term patience is to have confidence in yourself. I feel very confident in the skills that I’ve learned over the last five years and believe they are going to translate to storytelling for other brands. I mean, I really understand what it means to make impactful content on the behalf of brands that want to make money.

The biggest shift I’ve seen in my five years here is just the rate of change. Everything has changed, and it’s going to change again tomorrow. For instance, Instagram Stories comes out - who really knows how to best execute Instagram Stories? The answer is nobody. I mean, there may be some practitioners who have done similar things on other platforms, but the real answer is nobody’s done it. People always wonder whether they should get on whatever the new app of the day is, but really there’s no downside because the learnings that you got from building an audience on Snapchat still apply when something similar - like Instagram Stories - comes along. And the gaps between those new platforms are closing. The rate of change and learning is just insane at the moment, so there’s questions around how we are hiring and educating for that change as well. 

Recently, someone described me as curious. It’s not a word that I’ve ever really identified with, but I’ve thought about it a lot since and as my team grows it’s made me realize that curiosity is the skill I need to be looking for in the people we hire. Anybody can learn how to press the buttons on a Facebook ad or edit a video - it’s all on Lynda.com or YouTube - but how curious are you going to be about why and how it’s working? It’s the same in content creation, you have to have that sense of wonder that if we changed something, what would happen? I’m much more excited when someone that I’m managing comes to me with an idea because they’re curious and emotionally invested in this piece of content, versus me coming top-down and saying to them “hey, make this.” I want to know what you want to make because I think it’s you’re curious and invested in what you’re making, it’s going to be better than what I told you to make. That emotional investment is worth a lot, but obviously you can’t be so emotionally invested that it blinds you. To use a famous Gary line, “you have to really, really care, and not care at all.”

That would be my advice for anyone just getting into cycling as well: Have fun, don’t overthink it, and be curious. It sounds cliche, but start slow. I firmly believe that’s why cycling has been so awesome for me, because I’ve built up and learned over time, rather than trying to be a pro within the first 60 days.