Watch What Happens When Two Restaurant Owners Get Their Coach on the Hot Seat

In this special “Flipping the Table” episode of my podcast, “The Restaurant Prosperity Formula,” Jonathan and Brianna Cowan, multi-unit restaurant operators, take control, turning the tables on me for an insightful interview. Here's a glimpse of our conversation: full of takeaways on leadership, persistence, and what it takes to thrive in the restaurant industry.

I’ve known the Cowans for going on 15 years, and I’ve seen their transformation into prosperity firsthand. They own a 65-seat restaurant and cater around 100 weddings per year, offering a full suite of services from rentals to food to bar service. They’re currently building out a 12,000 square foot space with a restaurant on the main level and a wedding venue on the second floor. They’re documenting the process on their YouTube channel, Wooden Paddle. They also have a podcast, which they named based on something favorite restaurant coach says, “The Ready Fire Aim Podcast.”

Passion and persistence in the restaurant industry

We kicked off by discussing the key indicators of a restaurant owner’s potential. I’ve learned that success often comes down to two qualities: passion for hospitality and persistence. Passionate owners focus on creating incredible guest experiences—from high-quality, innovative menus to exceptional service. Persistence is equally crucial—restaurant ownership is full of challenges, and those who endure and keep pushing forward are the ones who make it.

But the real game-changer? Having a growth mindset. Owners with this mindset are open to learning and evolving, which separates those who thrive from those who struggle.

Innovation and leadership in the restaurant industry

What distinguishes great operators from the good ones? Innovation. The top operators are always looking for ways to evolve—whether it’s upgrading their technology, refreshing the menu, or finding new ways to lead. They’re not just leaders within their business—they aim to become industry leaders, always pushing boundaries and seeking the next challenge.

If not restaurants, then what?

When asked what I’d do if I couldn’t be in the restaurant world, my answer was easy: I’d coach rowing. Coaching is in my blood, and rowing has always been a passion of mine. Whether in business or on the water, I thrive on helping people grow and improve.

Lessons from my mentors in the restaurant business

I also shared insights from two key mentors who’ve shaped my career. The first was John Childers, whose mastery of selling from the stage opened my eyes to the power of my own knowledge and ability to connect with audiences. Another influential figure was Kamron Karrington, a marketing expert who taught me the value of copywriting and became a close friend and guide. From these mentors, I learned the importance of investing in coaching—sometimes it’s a hit, and sometimes it’s a miss, but it always pushes you forward.

A restaurant horror story (without names)

Of course, we couldn’t resist swapping a “Kitchen Nightmares”-style story. I described a consultation at a fine-dining Italian restaurant in Pittsburgh that had fallen into chaos—mold on the line, fire hazards, raw sewage in the kitchen, and more. I told the owner in no uncertain terms: “Until this is cleaned up, I’ll never eat here again.” It was a tough moment, but necessary.

Balancing passion and sustainability in restaurants

Toward the end, we touched on the challenges of running a business sustainably. One thing I’ve learned after a heart attack and selling my old company is that you can’t put your entire identity into your work. For me, finding balance through rowing has been essential.

Advice for aspiring entrepreneurs

We closed with a powerful piece of advice: be willing to be bad at something long enough to get good at it. Whether it’s launching a podcast or navigating the learning curve in business, the only way to grow is to keep going, even when it feels awkward or uncomfortable. As Jonathan and Brianna said, “Fire, ready, aim”—you can’t wait until you feel ready, or you’ll never start.

It was a blast turning the tables and hearing from two passionate entrepreneurs who embody the values of persistence and innovation. I look forward to watching them reach new heights—and maybe even hitting that elusive “Mastery” phase one day.

Click the podcast player above to listen in, or you can watch the video on YouTube, click here to download the latest episode.