Antonio Lennert’s story is a masterclass in reinvention, personally and professionally. He shares how a major life move, a creative career, and an unexpected obsession with Great Lakes surfing led to building Surf the Greats: not just a shop, but an ecosystem built around education, inclusion, and community. Along the way, we get a real look at what it takes to build something niche, and make it viable.

The conversation then turns inward: burnout, purpose, and the kind of personal work that doesn’t fit neatly into a business playbook. Antonio reflects on what it means to lose direction, how support systems can change outcomes, and why partnership alignment is one of the most underestimated leadership challenges. It’s honest, grounded, and full of insights for anyone building while also trying to stay human.

Connect with Antonio: https://www.linkedin.com/in/antoniolennert/
Antonio's coaching business: https://www.theridein.com/

Time stamps

00:00 – Welcome + why this conversation matters.

01:59 – Antonio’s background.

03:59 – Three major pivots: leaving Brazil, burning out in design, finding purpose in surfing.

09:12 – Identity, belonging, and why surfing became more than a sport.

14:56 – “Surfing in Toronto?” Great Lakes waves, tech shifts, and surf culture inland.

20:09 – Not about money: building an inclusive community and a full surf ecosystem.

31:59 – The inner-work phase: burnout recovery / 10-day silent retreat.

47:23 – Loss, grief, and leadership.

58:57 – Becoming a coach.

01:15:10 – What “change” means now.

01:25:10 – Looking forward: what’s most exciting now (purpose, momentum, and the next chapter)