📺 The Truth Behind College Football's Recent $40K Viral Marketing Stunt

In partnership with

Happy Wednesday.

Sports betting is becoming a cultural arms race.

As more states legalize gambling and customer acquisition costs continue to climb, the biggest winners in the sportsbook space won’t just have the best odds — they’ll have the best brand.

That’s exactly where Underdog is playing.

They’re not trying to out-promote DraftKings or out-discount FanDuel. Instead, they spent $40,000 to drop bright yellow “Portals” into two college football towns last weekend — creating a live, interactive rivalry experience between Norman and Ann Arbor ahead of Michigan vs. Oklahoma.

@underdogfantasy

Oklahoma and Michigan fans showed out yesterday 😂 #michiganfootball #oklahomafootball #collegefootball #cfb #fyp

It was part stunt, part art installation, and part cultural play. And it’s exactly the kind of thing Sam Berman, Underdog’s Head of Brand, wants to be known for.

This week, I talked to Sam about the Portal, building a brand in the most competitive market in sports, and why some of the most effective marketing can’t be measured in clicks.

🎧 [Listen to our full episode with Sam Berman]

HR is lonely. It doesn’t have to be.

The best HR advice comes from people who’ve been in the trenches.

That’s what this newsletter delivers.

I Hate it Here is your insider’s guide to surviving and thriving in HR, from someone who’s been there. It’s not about theory or buzzwords — it’s about practical, real-world advice for navigating everything from tricky managers to messy policies.

Every newsletter is written by Hebba Youssef — a Chief People Officer who’s seen it all and is here to share what actually works (and what doesn’t). We’re talking real talk, real strategies, and real support — all with a side of humor to keep you sane.

Because HR shouldn’t feel like a thankless job. And you shouldn’t feel alone in it.

Sign Up Free

5 Takeaways From Our Conversation With Sam Berman

1. The Portal is more than a gimmick—it’s a bet on cultural virality.

Underdog’s Portal activation let fans in Norman and Ann Arbor see and speak to each other live before Oklahoma–Michigan. Think ESPN meets Omegle—only it’s 8.5 feet tall and weighs 600 pounds.

Each Portal costs ~$20K and was built in just six weeks. But the goal wasn’t conversion—it was conversation. “If I see it on my feed from someone I didn’t give it to,” Sam said, “that’s the win.”

Underdog knows it's not going to drive deposits overnight. What they want is attention. Cultural relevance. Chaos.

2. They’re not trying to control the chaos — they’re enabling it.

One reason the Portal might work? It invites unscripted moments. Fans can walk up and talk trash to the other side in real time — with audio and video.

Underdog isn’t live-streaming it (for obvious reasons), but Sam’s betting that the best content will bubble up on its own:

“If I start seeing it organically on my Twitter… that’s a huge win.”

And if the wildest moments aren’t safe for Underdog’s channels? They might still drive awareness — and that’s kind of the point.

3. Underdog’s marketing strategy borrows more from Red Bull than DraftKings.

Instead of pushing app downloads, Underdog builds brand affinity through cultural relevance. They’ve leaned into real fans (“We Know Ball”), viral formats (“Average SEC Couple”), and internet-native storytelling.

It’s a long-term play. Sam estimates 80% of his time is spent on brand building, not direct acquisition.

“There’s no point in trying to win on promos alone,” he told me. “Everyone’s got money. What we have to win on is culture.”

4. Creators are central to Underdog’s playbook—but not for the reasons you'd think.

Yes, some are still paid on CPA (cost per acquisition), but more are now being tapped to create brand lift, not just conversions.

Sam’s team has built an influencer network in the hundreds, focusing on authenticity and alignment. “If they’re not already part of the culture, it doesn’t work,” he said.

The strategy: let creators talk about Underdog their way. No scripts. No generic plugs. Just chaos seeded into the right channels.

5. Sam’s litmus test for a good idea is gut feel — not metrics.

Underdog is still operating like a startup when it comes to brand building. There are legal and compliance guardrails, yes. But big ideas get greenlit based on instinct — not spreadsheets.

“If I think it would resonate with me and my friends, it’s probably a good sign.”

And while not every idea makes it past legal (RIP to the Underdog skydiving stunt), the company’s internal motto of “Give a Sh*t” helps keep things fast, scrappy, and fan-focused.

Why It Matters

Sports betting is one of the most expensive categories in consumer acquisition. DraftKings and FanDuel spent a combined $400M+ on marketing last year. Every new user gets harder to convert.

That’s why brands like Underdog are betting on brand itself.

The Portal is a perfect example: high ceiling, hard to measure, but extremely ownable. It’s the kind of playbook you’d expect from Red Bull, not a sportsbook. And that’s the point.

If this works, Underdog won’t just be known for its odds — it’ll be known for how it shows up.

🎧 [Listen to our full episode with Sam Berman]

📩 And don’t forget: Bottom of the Ninth is back this Friday with the top three stories in sports and business from the week.

See you then,
Tyler & Jake