Ryan Hawk built a business around his own name, voice, and ideas. Now he’s deciding how much of the business can grow beyond him, and how much he wants to keep at the center.
Ryan is the founder and host of The Learning Leader Show, where he has spent more than a decade interviewing leaders, athletes, authors, coaches, and other people he wanted to learn from. What began as his own creative alternative to a traditional leadership PhD now supports a broader business that includes speaking, books, leadership development, and a full team of coaches.
He enjoys the work. A lot of it comes naturally to him. And unlike plenty of founders trying to get themselves away from the center of their companies, Ryan isn’t convinced he wants out. His name and voice are a big part of what brings people in.
He knows the dependency creates risk, but removing himself from the center would also mean giving up some of the work he most enjoys.
For a leader who has spent years learning to play to his strengths, the next step isn’t obvious. How much of your company should you delegate if the work still depending on you is the work you would choose anyway?
Hard work finally met an outcome it couldn’t change
Ryan spent a lot of his early life learning to compete. As a quarterback at Miami University, hard work meant studying more game footage, spending extra time throwing with teammates, and putting in more hours in the weight room.
Then Ben Roethlisberger, who would go on to become a two-time Super Bowl-winning NFL quarterback, won the starting job.
Ryan had already spent two years trying to outwork the situation, and none of it changed the outcome. He could keep grinding at Miami or put himself somewhere else with a better opportunity to play. He transferred to Ohio University, competed for the job there, and became a Division I starting quarterback.
The experience challenged one of his strongest beliefs about effort. Working harder still mattered, but effort couldn’t overcome every environment, role, or set of circumstances. Sometimes the person in front of you is simply better at the job.
Ryan carried another part of football into his corporate sales career too. Playing quarterback is unusually zero-sum: one player starts, and the others don’t. In sales, stack rankings fed the same competitive streak. Ryan wanted to be at the top, and he admits he didn’t particularly want his teammates to do well if their results could move ahead of his.
Mentors pushed him to see the limitation and find a different version of winning.
Strong individual performance could earn recognition, but leadership asked him to mentor, share ideas, and become invested in others performing well.
He built the leadership education he actually wanted
After six years of earning his MBA while working full time, Ryan considered pursuing a PhD in management or leadership. He wanted to keep learning, but the traditional format didn’t appeal to him.
So he came up with another idea: build his own personal leadership PhD.
Ryan started The Learning Leader Show so he could choose his own “professors” and ask them whatever he wanted. He already had plenty of interview reps from hiring people in sales, and his sales background made the cold outreach less intimidating. Early on, he was emailing prospective guests himself, getting ignored, hearing “no,” and improving his interviewing skills through repetition.
The audience wasn’t even the main point at first. Ryan wanted access to people he could learn from.
More people began listening, and the side project grew into something substantial enough to create opportunities outside his corporate role. By late 2017, keynotes and leadership work were consuming his PTO. With a wife and five children, Ryan didn’t make a blind leap. He and his wife, Miranda, had lived below their means; she was still working, and paying clients had already shown there was demand for what he was building.
Ryan left corporate America going into 2018. The podcast has now reached 700 episodes, and his Mindful Monday newsletter has been sent hundreds of times. What started as a way to learn became the foundation for the career he has now.
The business grew around the things Ryan does naturally
Ryan has spent a lot of time thinking about what comes more naturally to him than it does to other people. Consistency is one example. Getting up early to write, prepare, train, or learn has been part of his routine for decades, so he doesn’t experience it as some extraordinary feat of discipline.
Curiosity is another. Ryan genuinely likes preparing for an interview, sitting across from someone with a life he wants to understand, and figuring out the next interesting question to ask.
His strengths proved commercially useful because he kept putting them to work. Instead of trying to build a career around everything he was capable of doing, Ryan kept following work he liked and was good at.
EOS describes a similar idea through Personal Core Focus: spending more of your time on work you love and do exceptionally well.
Ryan’s business now presents a particularly interesting version of the idea. He has coaches who deliver leadership development with clients, but the podcast, books, and keynotes remain closely tied to him.
And he’s not miserable about it. He loves preparing, interviewing, and speaking. He likes working with the team before and after client sessions to sharpen tiny details for next time.
The usual advice to “get yourself out of the business” gets trickier when getting out means giving up the work you love.
Frank Sinatra didn’t move his own pianos
There’s a useful comparison for the kind of company Ryan is trying to build: Frank Sinatra didn’t move his own pianos. He walked in, grabbed the microphone, and sang.
The point isn’t always to remove yourself from the work people value most. Sometimes the better move is to clear away the work around it so you can spend more time where you’re strongest.
Ryan is still in the middle of figuring out what this looks like. His company combines media with leadership development, and much of the demand stems from his name. He openly wonders how much key-person risk he wants to remove.
He could design the company for a future sale, which would require making it more transferable without him. He could also keep a business built partly around his involvement, enjoy the work, generate cash, and accept the tradeoff.
Neither direction automatically gives him the right answer. Ryan has to decide what he wants the company to provide before deciding how far to remove himself from it.
Are you delegating because the work belongs with someone else, or because you’ve absorbed the idea that a “good” founder is supposed to become unnecessary? The answers can lead to very different companies.
Consistency works best when you still care about the work
Ryan has published his podcast every Sunday for more than 11 years. His Mindful Monday newsletter has run for more than 500 consecutive Mondays.
A Jim Collins line raised an idea Ryan immediately connected with: “Mediocrity stems from chronic inconsistency.”
Ryan sees consistency as one of the strongest ways to build trust. If people know you’ll do what you said you would do, they begin to trust the pattern.
But repetition creates another problem for plenty of high-performing leaders: boredom. Ryan hasn’t experienced much of it.
The format may repeat, but the people keep it interesting. Every guest brings another life story to understand. Every client team has its own personalities and issues. Every keynote creates another round of preparation, performance, review, and adjustment.
His coaching curriculum can stay consistent while the people keep the application interesting. The podcast can follow the same publishing rhythm while every interview gives his curiosity somewhere new to go.
Ryan describes the after-action review as part of the fun. After a leadership session, he and his team might step aside and critique a transition, a slide, or some small piece they want to improve for the next group. He doesn’t seem to love only the result. He loves preparing for it.
Ryan found his clue in the part that never got boring
There’s a reason the Frank Sinatra comparison fits.
Ryan has already stripped away pieces of the work other people can do. Coaches can serve clients. A team can support production and delivery. Other people can handle responsibilities around the core work.
What remains is unusually hard for him to imagine giving up.
The podcast still gives him access to people he wants to learn from. Speaking still gives him something significant to prepare for. Coaching still lets him study leadership up close. His curiosity keeps supplying new material.
Ryan’s current ceiling isn’t simply that too much depends on him. Part of the dependency exists because he has built around abilities and interests he has spent years strengthening.
So the work now is more precise: Protect the part only Ryan needs to do, build support around it, and stay alert to whether his involvement is serving the company or merely remaining familiar.
He hasn’t finished sorting it out, and that may be what makes his story useful. Plenty of leaders know they need to delegate what drains them. Fewer know what to do once most of what remains is work they’re very good at and still excited to do.
What work would you keep even if nobody told you that you had to? And how much of everything surrounding it could someone else own so you had more room to do it exceptionally well?
To hear Ryan talk more about building The Learning Leader Show, knowing what work to keep, and leading through growth, listen to Episode 26 of the Hitting the Ceiling podcast.
For more ideas, questions, and lessons from inside the Visionary seat, subscribe to Mark O’Donnell’s Clarity Break Thoughts newsletter.
