Why obsession isn't a dirty word

Welcome to The Storyteller's Playbook.

This past Wednesday I spoke at an event with Silicon Valley Bank here in Miami on storytelling and how to use it to fundraise venture capital. Then we had some Q&A with an early stage VC and myself.

I'll be releasing the full 32 minute video of the talk in the coming weeks on my YouTube channel along with all new videos. Most of my new video content will be only on YouTube this year.

So if you want to keep up with the video content, subscribe here.

Let's get to the deep dive.

DEEP DIVE: The World-Class Mentality

What does it take to be a world-class founder?

You can have all of the right “stuff”—the right PMF, the right team, the right management skills.

All of those things can make you a great founder. But in order to be world-class—to sit among the Jobs, the Blakelys, the Musks, the Oprahs, the Bransons—you need something that you can’t buy or practice.

You need the right mentality.

It’s obvious when a person approaches their craft with a world-class mentality. They have a level of obsession that’s written all over their face.

Obsession is good. My take...it's a requirement to reach the top of any field. Sports, music, and business.

Obsession drove me as a prosecutor. Being the best in any courtroom I walked into kept me up at night. I was chasing perfection and excellence. Every day was a chance to get closer, all while knowing I would never reach it.

Nothing changed when I left that world behind after trying the biggest and most serious cases. When I built my edtech, I approached it the same way. That led to an acquisition.

Throughout the past ten plus years I've been obsessed with storytelling, strategy, and communication. It never fades which is why I say it's a requirement. The best founders I've met and worked with, all check that box.

Now it's not just my take.

Despite being legendary for his cartoonish masculinity and debauchery, Ernest Hemingway was one of the most disciplined writers of the 20th century. He wrote most days from 6 a.m. until noon, and contrary to popular belief, he never touched a drop of alcohol until his day’s work was complete. Hemingway said he often drank to occupy himself until it was time to write again.

“When you stop you are empty,” Hemingway said in an interview. “You stop and try to live through until the next day when you hit it again. Nothing means anything until the next day…It is the wait until the next day that is hard to get through.”

This is the mentality of world-class people. In the founder, venture, and tech world, I see it every day. The rare talents have a certain feel to them, a hunger that can only be described in cliches. Their lives reflect what it takes—tons of work, sacrifice, and perseverance. And they have a resulting aura.

Mamba In Retirement

In 2015, the announcement that Kobe Bryant would be retiring from the NBA sent shockwaves through the basketball community. Over the course of his 20-year career, Kobe won five NBA championships and made the all-star team 18 times. He was just ONE ring away from tying Michael Jordan.

There were rumblings of Kobe playing overseas—maybe joining an Italian team like his father, Joe, did after he retired. But ultimately, Kobe decided to step away from the game altogether, even telling reporters he wouldn’t be watching many NBA games.

He told others that he didn’t intend on picking up a basketball—even if it was “just for fun.”

Why? How could someone who devoted their entire lives to something quit cold turkey? How does that make any sense?

It was all about his mentality. Kobe was all about excellence and being the best. He knew what it took to be the best on the court during his career, and he knew he wouldn’t love playing pick up ball if he wasn’t the best.

He expressed this sentiment in his retirement announcement, which he published in poem form in The Players’ Tribune:

I can’t love you obsessively for much longer…

My heart can take the pounding

My mind can handle the grind

But my body knows it’s time to say goodbye.

And when I say that Kobe was about excellence and being the best, I don’t just mean winning. After retirement, a podcast host asked him if he’d come back to the game if he was guaranteed a championship—perhaps landing on a super team destined for success.

“No. No. No. No no no,” Bryant said. “I like my rings the hard way. I like fighting for them and earning them. I don’t like jumping to the easier route, so I wouldn’t take it.”

Believe it or not, Bryant actually had something in common with Hemingway. In his latter years, Hemingway’s health unraveled. As a result of multiple head injuries he sustained over the course of his life, he developed CTE and found himself unable to write the way he once did. His inability to do so ultimately resulted in Hemingway taking his own life in 1961. He would rather have died than be confronted with his diminished abilities.

Is It In You?

I’d love to tell you that we all have that Mamba mentality inside of us, and all it takes is a little searching.

For some, that might be true, but for others, your search will be in vain. There’s a reason not everyone is world class—some don’t have what it takes. That’s a harsh truth, but a truth nonetheless.

I've used this example before but I'll bring it up again. I wanted to be a professional baseball player. I thought I could be the next Ken Griffey Jr. A sweet swinging left handed hitter crushing homerun after homerun.

Sadly, I wasn't good enough.

I saw this first hand when I played with a guy named Jay Bruce in high school. I remember watching him hit off a tee with a wood bat and having to pick my jaw up off the floor. I'd never seen anybody with such a smooth and powerful swing.

I knew that he had it. I didn't.

Jay Bruce went on to play for a few teams and hit 319 homeruns during his career before retiring last year.

I couldn't be world-class as a baseball player. So I shifted my focus and leaned into strengths other people didn't have. The rest is history and now Competitive Storytelling is building in a way that I have no doubt will end up at the top.

I hope that journey is yours too.

It's not for everyone, but for those people who want to get there, study the greats. Study the greats across history and in different fields.

See what it took for them, the sacrifice, the sweat, the heartbreak. It will open your eyes to what it takes.

Once your eyes are open, you can make it happen.

The view from the top is worth it.

RESOURCES for Founders and Storytellers

If you want to know what it takes to become world class, start with Kobe’s book, The Mamba Mentality: How I Play. It’s a great insight into Kobe’s personal perspective of his life and career on the court. He details the steps he took mentally and physically to not just succeed at the game, but to be the best.

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Impromptu speaking is one of the toughest things for any founder, investor, or CEO to do well. There are strategies, tactics, and frameworks that can help you. It's all broken down here in this video to make sure you leave any audience in awe.

FINALLY...

I recently re-watched The Night Manager. It's a 6 episode series that is one of my favorites for the dialogue, characters, and of course storytelling.

It's about arms dealing and can be a little bit intense but it's an amazing show.

Next week we will be deep into storytelling and fundraising, so see you next week!

Know someone who might enjoy it? Please pass it along!

The Founder Fundraising Program is currently full but you can still reach out to join the waitlist for when a spot opens to work together. Application can be found here on the website.