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 E5: The REAL Story Behind Grant Horvat’s Good Good Exit [not-audio_url] [/not-audio_url]

Duration: 1:00:55
How did Grant Horvat go from teaching golf on TikTok to building one of the most-watched YouTube golf brands in the world? In this episode, Jimmy Roberts dives deep with the creator-turned-entrepreneur. They talk YouTube…
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Duration: 1:13:47
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S E2: INSIDE the $200M+ Ryder Cup at Bethpage: How It All Happened [not-audio_url] [/not-audio_url]

Duration: 51:53
Jimmy Roberts goes behind the scenes with the power players shaping the 2025 Ryder Cup at Bethpage Black: Guy Kinnings (CEO, Ryder Cup Europe), Jeff Price (Chief Commercial Officer, PGA of America), and Larry Schwartz (G…
S E1: Eastside Golf’s WILD Ride: From Broke to Barack [not-audio_url] [/not-audio_url]

Duration: 52:12
Eastside Golf founders Earl Cooper and Olajuwon Ajanaku join Jimmy Roberts to share how they turned a side hustle into a multi-million dollar brand—collabing with Jordan Brand and landing retailers like Nordstrom and Dic…