S E24: How DraftKings Turned an Idea Into BILLIONS | Jason Robins

S E24: How DraftKings Turned an Idea Into BILLIONS | Jason Robins

Author: Big Swing Media April 15, 2026 Duration: 48:00
DraftKings CEO Jason Robins joins Jimmy Roberts to break down the business of sports betting, fantasy sports, and the future of golf wagering. From startup beginnings to a multi-billion dollar company, this is a deep dive into one of the fastest-growing industries in sports.With sports betting surpassing $167 billion in the U.S. alone, this conversation explores how companies like DraftKings are reshaping fan engagement—and why golf has become one of the most unique and valuable betting markets in sports.In this episode of The Big Swing with Jimmy Roberts, Robins shares the origin story of DraftKings, the challenges of building in a highly regulated industry, and how betting, technology, and media are converging to change how fans experience the game.From working nights and weekends out of a spare bedroom to scaling a company with thousands of employees, this is a real look at what it takes to build—and survive—in a competitive, high-stakes business.What we cover:How DraftKings started as a fantasy sports idea and evolved into sports bettingThe realities of raising money and scaling a startup to billionsWhy golf is one of the most unique betting markets in sportsHow odds are created using data, simulations, and modelingThe impact of legalization and regulation on the industryThe role of betting in fan engagement—and where it’s heading nextAdvice for entrepreneurs building from scratchFor anyone interested in golf, sports business, startups, or the future of fan engagement—this is a conversation worth your time.🔔 Subscribe for New Episodes Every Wednesday Morning▶️ Watch on YouTube | 🎙️ Listen on Apple Podcasts & Spotify📺 Live on Golf Channel Every Tuesday Morning at 7am & 9amThe Big Swing with Jimmy Roberts is produced by Big Swing Media. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Hosted by sixteen-time Emmy winner and broadcasting legend Jimmy Roberts, The Big Swing with Jimmy Roberts goes far beyond the fairway. This isn't just another sports interview series; it's a deep exploration of the powerful forces and fascinating personalities driving the modern golf industry. Each episode features an intimate, one-on-one conversation with the executives, celebrities, and elite athletes who are actively shaping the game's future, from groundbreaking deals and major investments to the cultural trends redefining the sport. You'll hear candid stories and gain unparalleled access to the boardrooms and backstories behind the headlines. Presented by Big Swing Media, this podcast delivers a unique blend of sports, business, and insider perspective, offering listeners a sophisticated look at where the game is headed next. Tune in for thoughtful dialogues that reveal the strategy and passion fueling golf's biggest swings, both on and off the course.
Author: Language: English Episodes: 46

The Big Swing with Jimmy Roberts
Podcast Episodes
S E48: Why the PGA Tour Won’t Sell the Presidents Cup [not-audio_url] [/not-audio_url]

Duration: 20:23
The Presidents Cup has been dominated by the United States—but judging the event by the final score misses the much bigger business story.Ahead of the 2026 Presidents Cup at Medinah Country Club, Jimmy Roberts sits down…
S E47: The USGA’s Plan to Protect Golf’s Future [not-audio_url] [/not-audio_url]

Duration: 48:40
USGA CEO Mike Whan joins Jimmy Roberts for a wide-ranging conversation about the decisions that could shape golf for generations.Whan explains why the continued increase in distance at the elite level has become one of t…
S E46: Peyton Manning Is Bringing Football’s Media Playbook to Golf [not-audio_url] [/not-audio_url]

Duration: 48:20
Peyton Manning knows how to turn sports into entertainment—and now he’s bringing that experience to golf.The five-time NFL MVP and founder of Omaha Productions joins Jimmy Roberts to explain why he believes golf is a sma…
S E45: How CEOs Decide If a Golf Sponsorship Is Worth It [not-audio_url] [/not-audio_url]

Duration: 48:38
Golf sponsorship is big business—but some of its most important returns can’t be measured on a spreadsheet.Live from East Lake during the Tour Championship, Jimmy Roberts sits down with Coca-Cola President and CFO John M…
S E44: They Bought an ABANDONED Golf Course for $200K [not-audio_url] [/not-audio_url]

Duration: 47:03
Tye Nichols and his family paid $200,000 for 44 acres and an abandoned nine-hole golf course in Chesterville, Maine—with no experience in agronomy, course design or restoration. A year later, Fairway Fields has a working…
S E43: She Took On Golf’s Old Boys’ Club—and Won [not-audio_url] [/not-audio_url]

Duration: 47:45
Kelley Brooke has gone head-to-head with some of golf’s largest management companies—and won—by taking on the financial risk herself and obsessing over every detail of the customer experience.At Montauk Downs, Jimmy Robe…
S E42: Where Golf’s Smart Money Is Going Next [not-audio_url] [/not-audio_url]

Duration: 47:49
Golf’s estimated economic impact reaches roughly a quarter-trillion dollars—but where is the smart money going next?Matt Erley, co-founder of Old Tom Capital, joins Jimmy Roberts to explain why investors increasingly see…
S E41: John Smoltz on Building a NEW Pro Golf Tour [not-audio_url] [/not-audio_url]

Duration: 48:37
John Smoltz thought the idea was great—but that it would never work.Now, the Baseball Hall of Famer is helping build THE PRO, an invitation-only professional golf tour created exclusively for former athletes. With approx…
S E40: How Delta Became a Power Player at the Masters and PGA TOUR [not-audio_url] [/not-audio_url]

Duration: 47:39
Why is one of the world’s largest airlines making such a significant investment in golf?Delta Air Lines CEO Ed Bastian joins Jimmy Roberts to explain why the company’s relationships with the Masters, the PGA TOUR and som…
S E39: Steph Curry Is Building His Next Chapter in Golf [not-audio_url] [/not-audio_url]

Duration: 45:23
Steph Curry is already planning his next chapter—and golf is becoming a central part of the legacy he wants to build beyond basketball.In this special episode of The Big Swing with Jimmy Roberts, Curry shares how a child…