Welcome to Lead without Limits, where I share actionable tips each week on how to realize the full potential of your leadership, career, and mindset.
If you’re new here, subscribe to never miss a post.
Periodically, I have the privilege of hosting inspiring leaders in a live conversation. Watch the full conversation above. Read my synopsis below or scroll down to the bottom of the post to access a timestamped summary.
When Rob DeGisi introduces himself to his Wharton students, he doesn’t lead with his impressive resume. He leads with this: “I’m a husband, I’m a father, I’m a Boston College alum, a Wharton MBA, and a New Jersey guy through and through. But as long as I can remember, I live for the New York Yankees.”
That opening says everything about what matters most—and it’s a lesson that took him decades of career pivots, unexpected setbacks, and hard-won clarity to truly understand.
I had the privilege of sitting down with Rob for a Substack Live conversation that revealed the messy, human journey behind a career that looks polished on LinkedIn. What emerged wasn’t just a story about breaking into the notoriously opaque sports industry. It was a masterclass in resilience, adaptability, and redefining success on your own terms.
The Accidental Path into Sports
Rob’s journey started as an accounting major at Boston College—not because he loved accounting, but because his father and older brother were accountants. He had no idea what he wanted to do. But he was part of the student radio station, broadcasting BC basketball, football, and hockey games.
The turning point came junior year when he was sent to Pittsburgh to cover a Boston College football game. As a 20-year-old coordinating booth setups, phone lines, press passes, and locker room access, he had a realization: “These grownups have pretty cool jobs.”
That observation sparked something.
Rob started networking before it was even called networking—making phone calls, sending paper letters, figuring out how to find a typewriter to type envelopes. He sent his third paper letter to IMG with a killer phrase: “I have aspirations for a career in the sports industry. However, I can contribute to your accounting needs right now.”
That letter worked. He got the call. And his advice for anyone trying to break into any competitive field? Focus your communication on what you can do for them, not why you find the industry interesting.
Every firm needs specific skills. Rob had accounting credentials, he’d passed the CPA exam, he’d worked at a big public accounting firm, and he was willing to move to Cleveland at 22 without knowing a soul. That combination got him his first job at IMG, where he spent four years in their television and golf divisions—all from a financial perspective.
But Rob realized something important: he was perceived as a finance person who happened to work in sports, when he wanted to be a sports business person who happened to have finance skills.
To make that pivot, he went to Wharton.
The Two Houses, No Job Moment
After Wharton, Rob’s plan didn’t quite work out as expected. He spent 20 months building relationships, heading to New York every other weekend for informational interviews. But by May 1993, he needed a paycheck—he had loans to repay. He took a job at CUC International, not in sports, but it’s where he learned strategic planning and direct response marketing.
Two years later, all that relationship building paid off. He got a call about an opportunity at the NBA. The guy interviewing him leaned back in his chair and said, “I’m not going to interview you. I already know you. You’re perfect for this job.”
Rob spent four years at the NBA, then moved to Bank One’s credit card division in Delaware, then eventually found himself at a startup salty snacks business in New Jersey. That’s where everything fell apart.
In August 2008, Rob moved his family from Delaware to New Jersey for what he thought would be a stable opportunity to grow. He bought a house in New Jersey but hadn’t sold his Delaware house yet. Within weeks, the CEO was kicked out by investors—the startup was burning through cash unsustainably. Then in September, Lehman Brothers collapsed and the global financial crisis hit.
“I owned two houses and had no job,” Rob said. “The fall of 2008 was awful. My last day wasn’t officially until the end of February in 2009. But it was a really difficult time.”
Fortunately, he sold the Delaware house in November. And he kept his salary through February. But the uncertainty was real, and it was scary.
What got him through?
The relationships he’d built over years. He joined a networking group of Wall Street professionals who’d lost their jobs. One of them connected him to someone who connected him to Copart, a public company in the automotive industry. By May 2009, he had an 18-month consulting gig leading their sports marketing initiatives.
The lesson: Relationships aren’t transactional. They’re insurance policies you don’t know you’re building.
When you invest in people without expectation, you create a safety net that catches you when everything else falls apart.
Redefining Success at Midlife
When Rob got laid off in February 2002 from Bank One’s credit card division, he went out on his own as an independent partnership marketing executive, working with clients like Citizens Bank and with the horse racing industry.
About a year into consulting, something unexpected happened. The marketing students at Wharton petitioned for a sports and entertainment marketing course.
The marketing chair asked Rob’s former professor (who Rob had stayed in touch with and guest lectured for) “Do you know anyone who could teach this course?” The professor recommended Rob.
Rob started teaching part-time at Wharton from 2003-2005 while running his consultancy. He taught what was then called a “mini” — a half-semester course. But it was hard to juggle both. After three years, he stopped teaching to focus on his busy consulting schedule.
Years later, he came back to teaching. And this time, it stuck. He’s now taught at Wharton for 11 years and has no plans to stop.
Here’s what struck me most: Rob doesn’t teach for the money. He teaches because it fills something in him that consulting alone couldn’t. “I might not have the second home like some of my classmates from Wharton do,” he said, “but I have this. And this is incredibly important to me. And you can’t buy this.”
The deeper truth?
At a certain point in your career, success stops being about accumulation and starts being about contribution. Rob found fulfillment not in what he could extract from his expertise, but in what he could give through it.
The Unsexy Middle of Any Journey
One of the most honest moments in our conversation was when Rob talked about the grind. Not the glamorous parts of working in sports, but the years of doing work that felt incremental, uncertain, and far from the highlight reel.
“There’s always doubt,” he admitted. “You wonder if you’re on the right path. You wonder if it’s all going to work out. But you keep showing up. You keep building relationships. You keep saying yes to opportunities even when you’re not sure where they’ll lead.”
This is the part of career journeys we don’t talk about enough. The unsexy middle. The years between early ambition and late-stage clarity where you’re just trying to figure it out.
The people who make it through aren’t the ones with perfect plans.
They’re the ones who stay curious, stay connected, and stay open to possibilities they couldn’t have imagined at the start.
What Rob’s Story Teaches Us
As I reflected on our conversation, three themes kept surfacing:
1. Relationships are the real ROI
Rob’s entire career has been built on relationships, not as networking transactions, but as genuine human connections. He doesn’t connect with people to get something from them. He connects because he’s genuinely curious about their stories. That authenticity is magnetic. And over time, those relationships compound in ways you can’t predict or control.
Harvard’s longest-running study on happiness confirms what Rob discovered through experience: relationships are the greatest predictor of health, wealth, and fulfillment. Not status. Not salary. Not even passion. Relationships.
2. Adaptability beats planning
Rob didn’t set out to be a Wharton professor. He didn’t plan to lose his job right after buying two houses. He didn’t know in 1983 that asking “How’d you get your job?” would lead to a 30-year career in sports.
He adapted. He stayed open. He followed curiosity over certainty. And that flexibility allowed him to build a life far more fulfilling than anything he could have designed at 22.
3. Fulfillment comes from giving, not getting
Rob’s consultancy is successful. But teaching? That’s where his passion lives. It’s where he feels most alive. Not because of what it gives him in status or income, but because of what he can give to his students.
As senior leaders, we often spend the first half of our careers accumulating titles, compensation, achievements. And the second half? That’s about contribution. About using what you’ve learned to make others’ journeys easier. That’s where real fulfillment lives.
What Rob Didn’t Share in Our Live Conversation
After the Substack Live, Rob and I debriefed and I realized we missed perhaps the most important piece of guidance that Rob gives his students — what made the biggest difference in his career: his life partner, his wife.
Without her, he wouldn’t have been able to navigate the pivots and challenges in his career. Her patience, her career, and her relentless support gave Rob and their family the support they needed as Rob discovered his path.
Choosing the right partner in life is as Rob puts it, the most important decision you’ll ever make. Having the right person by your side can lighten hardships, help you grow and develop, and help you savor the journey that much more.
Your Takeaways
If you’re navigating your own career journey—whether you’re just starting out, in the messy middle, or looking for what’s next—here’s what Rob’s story offers:
Start with curiosity, not asks. Want to break into a new field? Ask people how they got there. Learn first, build relationships, and opportunities will follow.
Invest in relationships without expectation. You’re not networking for transactions. You’re building a web of people who know you, trust you, and think of you when opportunities arise.
The unsexy middle is where the work happens. Stop waiting for clarity. Stay curious. Say yes to opportunities even when you’re not sure where they lead. It won’t be easy, but you can do it. Keep showing up.
Define success on your own terms. Rob could have kept chasing bigger roles and bigger paychecks. Instead, he chose teaching. He chose contribution. He chose fulfillment. What does success actually mean to you?
Adaptability is a superpower. You don’t need a perfect plan. You need curiosity, resilience, and the willingness to pivot when life throws you curveballs.
Rob’s story reminded me why I do this work. Because behind every polished LinkedIn profile is a messy, human journey full of doubt, pivots, and hard-won wisdom. And when leaders like Rob share those stories honestly, it gives the rest of us permission to navigate our own journeys with more grace and less perfection.
Your Turn
So here are my questions for you:
What would it look like to redefine success not by what you accumulate, but by what you contribute?
What would change if you treated your career not as a ladder to climb, but as a course to find—one that’s uniquely yours?
Take a moment to reflect and reply or share your thoughts in the Comments. I read every response.
Connect with Rob
You can find Rob on LinkedIn and on his website: www.ironhorsemarketing.com. Follow him for meaningful insights on the changing sports business landscape. In addition to teaching at Wharton, he is also a strategic business advisor and a gifted keynote speaker.
If this conversation resonated with you, please consider adding a ❤️ so that more leaders can discover this post on Substack.
And if you know of a leader who could benefit from this post, please consider sharing it.
If you’re a leader in the accumulation phase, the messy middle, or a later stage of your career, I welcome hearing from you. There is no perfect moment — just the one you’re in.
May you lead without limits,
Conversation Topics with Timestamps
Want to dive deeper into specific parts of our conversation? Here are the major topics we covered:
[00:05:01] Early Career: From Accounting Major to IMG – How Rob discovered sports broadcasting in college and landed his first job at IMG through persistence and positioning his accounting skills
[00:14:30] Breaking Into Sports: The Power of Asking Questions – Rob’s philosophy on networking: ask for information, not jobs, and build relationships authentically
[00:21:45] The Two Houses, No Job Moment – The scary period when Rob lost his job after buying two homes and how his network became his safety net
[00:28:20] Career Pivots: Teaching at Wharton – How Rob started guest lecturing and eventually taught his own course at Wharton while running his consultancy
[00:35:12] Becoming a Wharton Professor – The unexpected journey from guest lecturer to teaching his own course on the business of sports
[00:42:15] Teaching Philosophy: What Students Really Need to Learn – Why Rob closes every semester with “What I Wish They Told Me in 1987” and the life lessons he shares beyond the curriculum
[00:48:30] The Unsexy Middle of Career Journeys – Rob’s honest take on navigating doubt, uncertainty, and the years between ambition and clarity
[00:53:00] Redefining Success: Relationships Over Assets – Why Rob values his teaching relationships more than material wealth and what fulfillment really looks like at this stage of his career
