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

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 betting

The realities of raising money and scaling a startup to billions

Why golf is one of the most unique betting markets in sports

How odds are created using data, simulations, and modeling

The impact of legalization and regulation on the industry

The role of betting in fan engagement—and where it’s heading next

Advice for entrepreneurs building from scratch

For anyone interested in golf, sports business, startups, or the future of fan engagement—this is a conversation worth your time.

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