Red Owl Boxing CEO Greg Bloom on Fighting, Business and Family
Every fighter needs someone in their corner.
After talking with Greg Bloom, CEO of Red Owl Boxing, I was reminded that the same thing is true in business—and in life.
Greg has spent more than two decades working around combat sports. He’s been a lawyer, manager, adviser and executive. He’s represented fighters, negotiated contracts, helped develop athletes, expanded fight promotions into new markets and traveled around the world pursuing opportunities in an industry he has loved since childhood.
Today, he’s bringing all of that experience to Red Owl Boxing, an ambitious boxing company working to identify, develop and showcase the sport’s next generation of fighters.
But my conversation with Greg on The Travel Wins Podcast wasn’t only about boxing.
It was also about something many business travelers understand very well:
How do you chase professional opportunities around the world while still being present for the people waiting for you at home?
For Greg, having a supportive and understanding wife while raising a family has been an important part of making that journey possible.
Boxing Came First
Greg’s connection to boxing began long before he became an executive.
Growing up in Miami, he was fascinated by the sport. He watched fights on television and eventually stepped into a boxing gym himself as a teenager.
What started as an interest became a lifelong connection to combat sports.
But Greg didn’t initially follow the traditional path into boxing promotion.
He went to law school.
And that’s where his professional relationship with the fight business really began.
The Lawyer Who Became a Fighter’s Advocate
While attending law school in the early 2000s, Greg found himself advising professional fighter Gilberto Reyes during a contractual dispute.
His advice helped.
That led to an opportunity to manage Reyes.
One fighter became more.
By the time Greg finished law school, he had developed a sports agency representing approximately 25 athletes across boxing and mixed martial arts.
Suddenly, the law student who loved boxing wasn’t simply watching the sport anymore.
He was helping fighters navigate it.
That legal background gave Greg a different perspective.
A fighter might understandably focus on the purse and the opponent.
A lawyer looks at everything else.
What rights are being signed away?
What obligations are buried in the agreement?
What happens next?
How does today’s decision affect the fighter’s career tomorrow?
Greg learned early that protecting athletes required understanding both sides of the equation:
the fight and the business behind the fight.
More Than a Lawyer
His role quickly expanded.
Greg wasn’t simply reviewing contracts.
He was helping fighters make career decisions.
Finding trainers.
Evaluating opportunities.
Understanding promoters.
Planning next moves.
Managing relationships.
His legal education gave him a foundation, but experience taught him the realities of the fight business.
Those lessons accumulated over more than two decades.
And eventually, they prepared him for something much bigger.
Taking Combat Sports Around the World
Combat sports became an international career for Greg.
Before becoming CEO of Red Owl Boxing, he served as CEO of Bareknuckle Boxing, where he helped expand the promotion’s live-event footprint into numerous new markets.
- That meant travel.
- A lot of it.
- Domestic events.
- International events.
- Media negotiations.
- Every new market presented another set of challenges.
- What works in one city doesn’t necessarily work in another.
- What works in the United States may need to be adjusted internationally.
- That’s where experience becomes valuable.
You learn how to walk into unfamiliar environments, understand the people involved and find a way to make everything work.
The Part of Business Travel We Don’t Talk About Enough
But there is another side of all that travel.
Family.
It’s easy to look at an executive’s travel schedule and see the exciting parts.
- International destinations.
- Big events.
- Major fights.
- Interesting people.
- Business opportunities.
What we don’t always see is what’s happening at home.
- School events.
- Family dinners.
- Everyday moments that don’t appear on an itinerary.
When you’re raising a family while building an international career, somebody else is often carrying additional responsibility while you’re away.
Greg spoke about the importance of having an understanding wife and family as he navigated the demands of the fight business.
That support matters.
Success Is Rarely a Solo Accomplishment
We often describe successful people as if they accomplished everything independently.
They didn’t.
There is usually someone else making sacrifices.
Someone adjusting schedules.
Someone taking care of things at home.
Someone answering the late-night phone call.
Someone saying, “Go. I’ve got this.”
For people who travel extensively for work, an understanding spouse can become one of the most important—and least publicly recognized—parts of a successful career.
That doesn’t mean the arrangement is always easy.
It means communication and appreciation become essential.
Greg’s story provides an important reminder that professional success and family success don’t have to compete with one another, but balancing the two requires effort from everyone involved.
A New Chapter with Red Owl Boxing
In 2026, Greg became CEO of Red Owl Boxing.
And he’s joining the company at an interesting moment.
Red Owl isn’t positioning itself simply as another boxing promoter. The company describes itself as a media company focused on developing and showcasing the next generation of fighters through consistent programming and competitive matchups.
Its philosophy is refreshingly straightforward:
Build reputations, not records.
In boxing, promising fighters have traditionally been protected carefully while developing undefeated records.
- Red Owl wants fighters tested.
- Competitive fights.
- Real opponents.
- Real development.
The idea is that when a fighter eventually reaches boxing’s biggest stages, he or she has already experienced adversity inside the ring.
That’s a philosophy Greg understands.
Building Fighters Instead of Protecting Records
There’s something almost old-school about the idea.
A loss doesn’t necessarily mean a fighter failed.
Sometimes it means a fighter learned.
Greg believes competitive fights can reveal far more about a prospect than another easy victory designed primarily to protect an undefeated record.
Can the fighter adjust?
Can they handle pressure?
Can they recover after losing rounds?
Can they respond when the original game plan isn’t working?
Those are the experiences that develop fighters.
Red Owl’s strategy is built around creating those opportunities earlier.
Expanding the Red Owl Boxing Brand
Greg isn’t stepping into a company that’s standing still.
Red Owl is actively expanding its event footprint while developing fighters and growing its media presence.
The company’s BoxFest series streams internationally on DAZN, giving developing fighters exposure well beyond the arena.
Red Owl has also been taking events into different American markets, including Pennsylvania and Texas, while continuing to sign developing fighters.
And perhaps its most ambitious project is happening in Houston.
Building a Home for Boxing
Red Owl is developing The Owl’s Nest, a purpose-built boxing arena in Houston.
The planned two-story, approximately 25,000-square-foot venue is expected to open in 2027 and is being designed specifically around producing televised boxing events. Plans call for roughly 3,000 seats, luxury suites, production infrastructure, content-creation spaces and enhanced fighter entrances.
Think about the difference that creates.
Instead of adapting a multipurpose arena to boxing every time you produce an event, you create an environment specifically for the sport.
- Fighter experience.
- Fan experience.
- Everything can be designed around one purpose.
- That’s not simply promoting fights.
- That’s building infrastructure.
Boxing Is Also a Media Business
Greg’s experience is especially valuable because modern combat sports aren’t only about what happens inside the ring.
- They’re also about content.
- Social media.
- Behind-the-scenes access.
Fans want to know fighters before they become champions. That’s why Red Owl’s approach to developing young fighters has another dimension. You aren’t simply building athletic ability. You’re building an audience. A fighter’s journey becomes part of the product.
And Greg’s experience across law, fighter management, promotion, television and international events gives him a broad view of how those pieces fit together.
Why Greg Bloom Fits The Travel Wins
Greg’s story represents exactly why I started The Travel Wins Podcast.
Yes, he’s involved in boxing.
But this isn’t simply a boxing interview.
It’s a business travel story.
It’s about taking meetings in different cities.
Building relationships around the world.
Understanding different markets.
Managing unpredictable schedules.
Making decisions under pressure.
Leading people.
And then figuring out how to return home and be a husband and father.
Those are challenges that executives, entrepreneurs, salespeople, entertainers and athletes all understand.
The industry may change.
The balancing act doesn’t.
Watch My Greg Bloom Interview on The Travel Wins Podcast
If you’re interested in boxing, combat sports, entrepreneurship, law, sports business or the realities of traveling while raising a family, I think you’ll enjoy my conversation with Greg Bloom.
We talk about his beginnings in boxing, his legal career, representing fighters, traveling internationally, growing combat-sports brands and the opportunity he now sees as CEO of Red Owl Boxing.
But we also talk about life away from the ring. Because eventually, every flight lands. Every event ends. Every business trip concludes. And you go home. Building an exciting career matters.
Having people you love waiting when you get there might matter even more.
Connect with Greg and Red Owl Boxing on their social media pages:
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The Travel Wins intro song by Allison Johnson and Steve Stevens
