In just eight years, legal sports gambling in the United States has gone from a quiet gray market to one of the fastest-growing regulated industries in the country. What was once taboo to talk about during sports broadcasts is now unavoidably intertwined with every game.
You may love it. You may think society has lost its collective mind. I understand both perspectives.
Today I’m going to give you a behind-the-scenes look at how the industry actually works – especially the VIP world – plus a quick primer on the hottest trend in the space: prediction markets.
What is VIP in sports gambling?
In 2025, over $150 billion was wagered legally on platforms like FanDuel and DraftKings, turning them from adorable fantasy sports startups into ~20B market-cap behemoths.
I have worked at both companies. I started in 2014 as the 30th employee at the then little known FanDuel in a tiny WeWork room in Union Square, NYC. Then I walked through enemy lines for the Head of VIP role at DraftKings in 2019, a year after sports betting legalized in the US. After a bunch of consulting, advising, and rambling mixed in, I’ve landed at Underdog as a Vice President, where I’m taking on prediction markets.
I’ve long said that working at companies like Underdog, FanDuel, and DraftKings is closer to Google or Facebook than to a Las Vegas casino. These are true tech companies with departments like Product, Engineering, Marketing, Analytics, Compliance, and Legal. Just to name a portion.
I oversee the VIP Department. It’s the most juicy department (I’m unbiased, of course), since we interact with the high rollers. You may have heard these players referred to as Whales (losing players) or Sharps (winning players).
These players are the Top 1%. Surprising to some, they consistently make up about 50% of the revenue for sports gambling products. Acquiring them is difficult, and retaining them is a battle. Not only are you competing against other legal operators, but you’re going up against grey (offshore) and black (bookies) market operators that have a multi-decade headstart, and some unfair advantages (playing on credit & tax evasion!).
VIP Departments are usually made up of Hosting/Account Management, New Business/Sales, Events & Hospitality, and Strategy. It’s a true revenue driving function of the business.
VIP teams are the most involved with Responsible Gambling, which is a separate department at all of the top sports gambling operators. There are policies in place like wellness checks, financial reviews, and KYC, to protect customers from playing above their means. This is a very hot topic in the industry and one that I’m very close to. Vice industries are tricky, and this one is no different.
How it usually works is that a player (customer) will hit VIP status based on their volume of play. From that point forward they’ll be set up with an Account Manager, or Host, who will be their 1:1 concierge, responsible for handling any service request and customer support inquiry. But most importantly, they’ll be offering exclusive rewards through in-app promotions and bonuses, plus in-person experiences (game tickets, events, etc..).
The largest players in the industry may get flown out on a private jet to go to the Super Bowl in a suite with an A-list singer to their right and a social media superstar on their left. At these levels, the operator should be certain that the player can afford how much they’re playing.
Within the VIP cohort there are business owners, doctors, lawyers, trust fund kids, crypto bros, etc.. It’s an eclectic mix of high net worth individuals who are looking for a good time.
Where do Prediction Markets fall in?
Over the last 6 months, a new form of sports speculation (I am using that word instead of gambling intentionally) has emerged. Prediction markets are regulated marketplaces where participants trade contracts tied to real-world outcomes (such as sports results), with pricing that reflects the market’s implied probability. In the U.S., platforms like Kalshi and Polymarket operate under the oversight of the Commodity Futures Trading Commission (CFTC).
To the customer, these sports markets look eerily similar to sports betting markets. One of the main benefits to the US consumer today is that you can play these markets from states where online sports betting is not yet available (like CA and TX).
Some people are calling this a loophole. Others are calling it a genius truth seeking innovation.
The amount of hype and capital being thrown into the space is head turning. Kalshi and Polymarket recently raised funding rounds at 10B+ valuations from top VCs like Sequoia and A16Z. Sports are a meaningful percentage of the volume today, but these new companies are hoping to get other markets off the ground. At the time of writing this I can “trade” on the inches of snowfall I expect in NYC or who will have the most Spotify listeners this month (Bruno Mars is a HEAVY favorite).
My company Underdog is moving towards Prediction Markets as well. If you told us a year ago that we may have the chance to offer the best sports experience across the country, we would’ve jumped at the chance. This gives us that possibility.
Established FinTech giants Robinhood, Coinbase, and Crypto.com have all entered the fray. There has even been positive quotes recently from CEOs of Schwab and Goldman Sachs about potentially getting into the mix. It’s a wild scene out here!
It remains to be seen whether Prediction Markets will be competitive with Sports Betting or if it’ll be just a small piece of the pie. There are regulatory and structural hurdles that will have to be jumped over to even have a chance, but the upside is clear.
I’m knees deep in all of this, moving at break neck speed.
If you have any questions or just want to connect, you can find me on Linkedin or shoot me an email at Dillon.Borgida@underdogfantasy.com.
Dillon Borgida is a Sports Gaming Executive and Advisor, VP of VIP & Player Experience at Underdog Fantasy.
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