How 10 Mentors Got Me Through 13.1 Miles

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Up until 3 months ago, I hadn’t run a mile since middle school. And when I did it back then, I threw up.

I ran my first half-marathon last weekend, to honor the memory of a friend and for an incredible organization, Active Minds. 13.1 miles, and I did it in a respectable time.

In running, I’ve found that a spectator or fellow runner throwing me a high-five gives me a boost of energy to push it and dig deep. It’s not uncommon for runners’ bodies to be hurting, and a high-five gets them over a hump, taking the heavy lifting off the legs and letting the mind find a path toward the next stretch of miles.

In business, it’s the same thing. It’s always a source of inspiration to get a metaphoric high-five from the influential and experienced minds that have built the bridges that many of us are crossing. The goal is always to surround yourself with winners in this respect.

When I signed up to run, I was nervous, scared, and questioning whether I would finish. After some thought, in addition to training, I figured out a way to overcome any doubt and run with confidence.

My model to get through the half-marathon was straightforward: break the run into “chunks” of a playlist of songs which are linked directly to the lessons learned from the friends and mentors I’ve developed through social media and business.

Each song gave me a new subject for reflection and thought, and it took me back to the various dialogues and lessons learned from these incredible people. With this strategy, the run was over before I knew it.

In addition to running with the memory of my friend at my back, and the support of my family in the crowd and in my heart, here are 10 mentors and friends — each one a different part of my race — and the songs that I associated with each, in no particular order.

1. Michael Lazerow: Ride by Cary Brothers

Laz, a serial entrepreneur, called me a “wild man” when I told him the following: the ultimate catalyst for my decision to create Excel Capital Partners was watching Mike’s video, fifty times on repeat, the day that he sold Buddy Media to Sales Force. This is the song from the video. It’s Laz’s mantra of living fearlessly that I carry with me every day, which is why the song made multiple appearances on the running mix.

2. James Althucher: The Wall by Pink Floyd

James, an author and entrepreneur, teaches me to write for nobody but myself, and to open up and be raw and honest. His encouragement to push the envelope and get to the core of my emotion with my words has been invaluable, and this song is a hat tip to James’ philosophy about formal education’s stifling of creative thought — “hey teacher, leave those kids alone!”

3. Brad Feld: Better Man by Pearl Jam

Foundry Group Managing Director Brad Feld’s generous back-and-forth about Digital Sabbath and encouragement to run has made me a better person. In practicing Digital Sabbath, the concept of unplugging on weekends to recharge the batteries, has altered my life significantly the better, period.

4. Gary Vaynerchuk: Gonna Fly Now (Theme from Rocky)

Meeting with Vayner Media founder Gary V. makes you feel like you can do anything, let alone run a half-marathon (or, in his case, buy a professional sports team.) Gary’s lessons of the import of context over content, and his story of building his business and building his brand is an amazing one. Connect with your audience! Provide context! This song fires me up to crush it every time.

5. Chris Paik: Patience by Guns n’ Roses

Patience is a virtue, a lesson I’ve come to further appreciate from Thrive’s Chris Paik. Chris has been nothing short of generous with his time and advice, and he’s always made it a point to focus on the import of patience and diligence before making decisions.

6. Derek Flanzraich: Born to Run by Bruce Springsteen and the E Street Band

My favorite song, my favorite band, my favorite entrepreneur. Derek’s company Greatist got me motivated to focus on health and wellness, and Derek is my daily dose of inspiration. Born to Run is the crescendo of the mix — it’s a nod to knowing that I don’t have to be “the” greatest, but that every day I must be “A Greatist” and be the best version of me each day.

7. Ben Lerer: Wild Nights by John Mellencamp

Thrillist Founder Ben Lerer was able to convert wild nights into an incredible media empire, and his focus on “being real” is the reason he’s such a success. Ben, like Gary, has the ability to pull life from the walls, and his enthusiasm for media and VC is contagious; it also doesn’t hurt that he’s wicked smart and an all around excellent guy.

8. Scott Belksy: Beautiful Day by U2

Behance founder Scott Belsky’s writing is nothing short of brilliant, easy to digest, and always on point. Scott’s work is a must-read, and his words of encouragement to me during his exceptionally busy time with the Adobe sale is the classic example of a business-high five.

9. Dhani Jones: Hearts on Fire by John Cafferty

It’s not often one gets athletic and life advice from a guy that started in the Super Bowl, and my friend Dhani’s constant encouragement to row (and row….and row….) was nothing short of hard-core and awesome. More importantly, my respect for Dhani runs exceptionally deep, particularly because of his thoughtful and kind nature, and his and focus on giving back through BowTie Cause.

10. Sarah Stanley: Edge of Glory by Lady Gaga

Ultra-marathoner Sarah Stanley became a friend, coach, and mentor through meeting on Twitter. Sarah was super inspirational in checking-in and coaching me through my first race. In talking to Sarah, I always felt pumped up, like I was ready to tackle the race and I was standing on the edge of glory, waiting for the starting gun to fire.

While the race course didn’t have too many spectators, my playlist was the mental equivalent of running up First Avenue in the NYC Marathon, as I had the benefit of reflecting on incredible lessons from my friends, and knowing that each was giving me a high five as I ran. And it was awesome.

With that said…today I signed up to run the New York City Marathon in November.

What would your playlist look like?

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