This week on Sportonomics, I sat down with Sam Berman, Head of Brand at Underdog, to unpack one of the boldest activations we’ve seen in the sports betting space.

As sportsbooks fight for market share, Underdog is going a different route—ditching promos in favor of personality. Their latest stunt? Two 8.5-foot “Portals” dropped into Norman and Ann Arbor ahead of Oklahoma–Michigan, letting rival fans talk smack in real-time.

We recorded this episode before the activation went live, so you'll hear us talk about it in future tense—but now that it’s happened, the strategy behind it is even more relevant.

Sam breaks down how Underdog approaches culture-first marketing, how they think about creators, and why they want to be more like Red Bull than FanDuel.

⏱️ TIMESTAMPS:

00:00 – Intro01:05 – What the Portal is and why it matters02:25 – Building the installation and fan interaction03:33 – How long it took to pull off04:00 – Legal concerns and NSFW risks05:25 – Risk vs. reward: avoiding a flop06:41 – Why virality > conversion08:47 – How they’ll measure success09:39 – What other brands can learn from this11:47 – Defining Underdog’s target audience13:25 – Letting creators run with the idea14:42 – From CPA deals to brand lifts17:00 – Staying nimble as the company scales18:28 – Internal motto: “Give a sh*t”19:32 – The wildest ideas that didn’t get approved21:31 – Red Bull as a brand model22:41 – Planning for unplanned activations24:16 – The evolving focus: acquisition vs. retention26:17 – Brand awareness gaps and growth27:24 – Sam’s litmus test for good marketing ideas28:25 – Staying relevant as you age out29:46 – What happens if the Portal flops?31:44 – Why the activation had a high floor32:23 – Other stunts that worked33:08 – Final Portal pitch