Ep. 50 | Your Career Isn’t Linear. It’s a Playground - Ryan Covert
Ryan Covert on Building With Intention (and Cold Plunges)
This week on the Shakin’ Hands Podcast, Jack Moran sits down with Ryan Covert: Entrepreneur, investor, coach, and now, the force behind Tidewater, a new kind of private club in Charleston built for community, not exclusivity.
Ryan’s journey is anything but linear, which is why his entrepreneurial story is picture-perfect for discussion.
From founding and exiting businesses in youth sports, elevators, hospitality, and more to now reimagining the country club experience, this episode is a crash course in entrepreneurial self-awareness, execution, and intentional life design. Let’s go over it:
From Cutting Grass in Rollerblades to Building Lifestyle Ecosystems
Ryan started his entrepreneurial journey at age 10, pushing a lawnmower on rollerblades. That same scrappy mindset has shaped everything he’s built since, from True Lacrosse and Genesis Elevator to his latest venture, Tidewater.
Ryan’s question has remained the same at every step: Where's the gap, and how do we fill it better than anyone else?
Why Customer Discovery Beats Pure Vision
Rather than building what he thought people wanted, Ryan surveyed 50 families like his own to find out what they actually needed from a social club. What came back wasn’t surprising: community, wellness, and authenticity were at the forefront of needs, but how Ryan and his co-founders implemented them is where the real magic lies.
Golf simulators, cold plunges, curated dinners, and family-forward events weren’t just guesses but data-backed design choices.
The Power of Knowing Yourself (and the People Around You)
Ryan shares how tools like the Predictive Index have shaped the way he hires, collaborates, and scales businesses.
“Most of entrepreneurship is learning what you suck at, and finding people who are great at that,” Ryan says.
He breaks down the three types of people every venture needs:
The Visionary (big picture, fast-moving)
The Operator (detail-focused, steady)
The Glue (team-first, emotionally intelligent)
Without balance, things fall apart. With the right mix? You get lightning in a bottle.
What 6 Companies (and 40 Years) Have Taught Him
Ryan’s not chasing a dollar figure; he’s building for freedom of time and alignment of values. He’s failed, pivoted, and outgrown earlier versions of himself, but his north star remains the same: build things worth doing, with people worth doing them with.
His advice for entrepreneurs? Learn by doing. Don’t fear failure. And never underestimate the impact of choosing the right partners.
Catch the Full Interview to Learn More
If you’re an entrepreneur or just someone trying to figure out how to blend work, life, and passion, Ryan Covert’s story will speak to you.
