FREE WEEKLY STORIES FROM JESSE STRAIGHT TO YOUR INBOX

Free Swim

Coach Charlie

Wouldn’t it be cool if there was a way to make a song play when someone opened your email?   If such a technology existed, I’d have programmed today’s Free Swim to play the intro for Monday Night ...

Taylor's Tale

First, a big shoutout and congratulations to Taylor, my incredible creative director, for finishing the Hennepin Hundred this past weekend!   That’s right—she ran 100 miles straight. When I think ...

Watch What You Say

Several years ago, I began training for a 100-mile race named The Last Man Standing. The rules were straightforward enough – every competitor had one hour to finish a 4.2-mile loop, and at the beg...

It's Their Journey

Several years ago, spring was in the air, and I knew it was time to sign my son Lazer up for little league baseball.   It was going to be his first season. Childhood memories flooded back as I ran...

Shaved

My hair's been my thing forever.   My hair is like Fonzi’s leather jacket, or for my younger audience, it's like Timothée Chalamet's cheekbones; something instantly recognizable, a signature featu...

Fruit Til Noon

In 1992, I decided to take on the challenge of running my first marathon.   I forget the exact reason I signed up for it, but I do remember that none of my friends wanted to join me. It was a solo...

Silent Heroes

Something happened a few months ago that got me thinking about the essence of teams and how we often underestimate the silent contributors.   Lincoln and Charlie, two of my sons, were part of a tr...

Happiness ISN’T A DESTINATION

The voice on my Waze app sounds like a guy with a deep, soothing voice. I picture Barry White.   I honestly don’t know how he got there. There used to be a woman with a British accent that, honest...

Don't Quit: Embracing Seth Rogen's Insight on Perseverance

Two weeks ago, I wrote about Unforeseen Doors of Opportunity. It was about being able to look beyond immediate obstacles and apprehensions, to see setbacks as possible pathways to something richer...

It's About That Time

Years ago, I was inspired to create a unique type of watch. One that doesn't tell time.   Yes, you heard that right... a watch that doesn't tell time.   Instead, it's just numbered one through 36...

Unforeseen Doors of Opportunity

I’m sure you’ve heard the expression, “Money’s no object.”   It’s a nice thing to say. But sometimes, we let money, or the lack thereof, get in the way of getting ahead. When I’d started a busines...

Normal Is Broken!

As an entrepreneur, I've learned that to be successful, you have to think differently.   You have to be willing to take risks and pursue unconventional ideas.   This is what I like to call irratio...

Interview Yourself

To save yourself the time and expense of attending seminar sessions or conducting a deep dive into your strengths and weaknesses, consider asking yourself a simple yet powerful question at every s...

Negotiating 101

I think the year was 1995 when I got a potential career changing opportunity. It was fire!   I got hired to do a rap recap of the NBA playoffs for 40 games in 40 nights, which basically meant I ha...

Living With The Monks

I believe that everyone should live on a monastery. Or is it at a monastery? I never know. Anyway…   Our greatest superpower is being in tune with our intuition, but it seems like technology has s...

The $10 Million Dollar Test

Recently, a friend of mine was in an unhappy place. Normally, he was an upbeat guy, fun to be around, but he was in a prolonged funk.   Life had become an uphill climb, and he couldn’t see the top...

Will You Be My Orangutan?

As many of you know, my wife is Sara Blakely, the inventor of Spanx. I could list a bunch of other accolades, but all you really need to know is that she’s had a remarkable career, she’s the most ...

A Streak Cal Ripken Jr. Would Be Proud Of

In the spirit of Father's Day last Sunday, I want to share a story about my dad.   You see, just like Cal Ripken Jr., who holds the record for playing in 2,632 consecutive games, my father had a r...

Dear Graduates

Good day, graduates, and congratulations on reaching this incredible milestone!  I haven’t given a commencement speech like this before, so I’m nervous. Real nervous. I haven’t been this nervous si...

Trust 101

My friend Turney Duff was a wall street trader back in the early 2000s, and one day he called one of his many sales traders with an order.   He said he was using anywhere between 50 and 60 differ...

Walk This Way

Growing up in New York in the '80s I fell in love with hip-hop. The culture. The music. Break dancing. All of it. But for me, one rap group stood tall, way above the rest. It was Run-DMC. They were...

Safety First

With the weather getting warmer, I wanted to share a story. It’s a scary story.   One day, a couple of years ago, I was out for a run, lost in thought, when suddenly a flood of ideas came pouring...

One Yes!

I published my first book in 2015, Living with a SEAL. We took it to 14 publishers, and they all passed, saying things like:   "You have 700 Instagram followers. Pass.”

Free Startup Idea!

I had an idea for a new product.   It all started with 5-Hour Energy. They changed the game by selling shots—taking an energy drink and shrinking it down to just two and a half ounces. Boom!