About

The full story

No skipped chapters. The achievements and the fall are both on the record, because both are why the coaching works.

$10MBudgets led
40Person teams
2Full Ironmans
1Multinational founded
1Comeback in progress

Most coaches teach frameworks they learned in a course. Mine came from building real things, losing all of it, and earning it back.

I started as a founder. In 1999 I launched Palmsite, a mobile company that grew from Miami into Argentina, Brazil, and Mexico, and was named a Top 10 Latin American startup in a field of 20,000. From there I spent a decade leading digital product and creative teams at the highest level of sports media: Director of Product Management at ESPN, where I built ESPN Sync for the 2014 World Cup; Creative Director at NBC Sports, where I helped grow the NBC Sports Gold streaming business from $8M to $23.5M in a year; and Vice President of Digital at NESN, where I built the network’s streaming ecosystem and launched NESN Bets. I managed teams of 40, budgets of $10M, and products used by millions of fans.

Fitness was the constant through all of it. I finished two full Ironmans, earned CrossFit, CrossFit Kids, and CrossFit Endurance certifications, and for years coached athletes as the owner of Kaulike Fitness. Discipline was never a hobby. It was the operating system.

Then I lost it. A white collar conviction cost me my career, my companies, my reputation, and my freedom. Thirty years of work, gone, by my own hand. There is no version of my story where I skip that part, because it is the part that taught me the most.

The rebuild is not finished, and I will not pretend otherwise. It runs on the same fuel as the building: discipline and systems. I became a certified paralegal and spent two years helping incarcerated men prepare their motions, remedies, and appeals, men with no money and no one in their corner. I negotiated my own family’s legal settlement. I am rebuilding my career, my family life, and my name, one kept promise at a time.

That is the coach you get: an operator who has built companies, led at the top, fallen to the bottom, and is doing the unglamorous daily work of coming back. If you are building, leading, or starting over, I know the terrain because I have walked all of it, and I am still walking the hardest part.

Ariel Legassa working at a desk beside a whiteboard Ariel Legassa crossing the Ironman finish line

Credentials

Coach U trainedCrossFit certifiedCrossFit Kids certifiedCrossFit Endurance certified2x Ironman finisherCertified paralegalDartmouth Tuck, Building a High-Performing Business

Discipline

Built in the air, too

The same discipline shows up outside work. I am a wingsuit skydiver with more than 800 jumps, and a licensed private pilot. Different altitude, same checklist: prepare, commit, review.

Ariel Legassa in a wingsuit above the clouds Ariel Legassa in the cockpit of a small aircraft

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