DraftKings’ next big bets, with CEO Jason Robins - Masters of Scale Recap

Podcast: Masters of Scale

Published: 2026-02-12

Duration: 32 min

Summary

In this episode, Jason Robins, CEO of DraftKings, discusses the company’s strategies for capitalizing on opportunities in the sports betting industry, particularly around major events like the Super Bowl. He emphasizes the importance of creativity and experimentation in marketing, especially in a competitive landscape.

What Happened

Jason Robbins, co-founder and CEO of DraftKings, opens up about the intense preparations leading up to the Super Bowl, which is their biggest event of the year. He explains how the entire team gears up with new product features and marketing campaigns, and the exhaustion that follows. DraftKings even gives employees the Monday after the Super Bowl off to recover, highlighting the effort that goes into making the event a success. Robbins quips, 'I think the Monday after the Super Bowl should be a national holiday.'

The conversation then shifts to the significance of the Super Bowl in terms of customer engagement and revenue. Robbins reveals that it dwarfs any other single event for DraftKings, not only in terms of volume but also because it serves as a pivotal opportunity to attract new customers. He notes, 'It’s just everything is sort of about the Super Bowl,' indicating the high stakes involved. While he can't provide exact figures, he mentions that the betting volume is in the 'hundreds of millions,' highlighting the immense financial impact of the event.

Robbins also shares insights about the creative processes behind their Super Bowl advertising. He acknowledges the unpredictability of marketing, stating that even seasoned professionals can be surprised by what resonates with audiences. He emphasizes the importance of trusting his marketing team and allowing them creative freedom. 'Some things are going to hit, some things are going to miss, but no one really knows until you actually do it,' he reflects. This perspective underscores the dynamic nature of marketing in a space as competitive as sports betting, where creativity must be paired with data-driven insights.

Key Insights

• The Super Bowl is the biggest event for DraftKings, dwarfing all other single events in terms of engagement and revenue.
• Robbins emphasizes the need for creativity and experimentation in marketing, especially during high-stakes events.
• Trusting the marketing team is crucial, as even experienced leaders can misjudge what will resonate with audiences.
• Turning potential risks into opportunities is essential for growth in a competitive industry.

Key Questions Answered

What is Super Bowl week like for DraftKings?

Jason Robbins describes Super Bowl week as a bustling time filled with preparations, product launches, and marketing campaigns. The team works tirelessly, tracking metrics and ensuring everything is ready for the big day. He humorously notes that the team is so exhausted after the weekend that they give everyone the following Monday off, suggesting that it should be a national holiday given the effort involved.

How significant is the Super Bowl for DraftKings compared to other events?

Robbins states that the Super Bowl is the biggest day of the year for DraftKings, significantly outpacing any other single event. He emphasizes how it activates customers and draws in new users, making it a critical moment for the company. The Super Bowl not only represents a peak in betting volume but also serves as a launching pad for future engagement with customers throughout the rest of the sports calendar.

What are DraftKings' plans for prediction markets?

Robbins notes that prediction markets are a relatively new venture for DraftKings, having only been in operation for about a month at the time of the episode. While he doesn't provide exact numbers, he expresses optimism for growth in this area during the Super Bowl, anticipating that new product features will enhance user experience and engagement leading up to the event.

How does DraftKings approach marketing in a crowded space?

Robbins acknowledges the challenges of breaking through in a crowded market, but points out that DraftKings’ content is directly tied to the games, giving them a unique advantage. He mentions the importance of experimentation, where the team tries various messages and creative strategies throughout the year to see what resonates best with their audience, even admitting that past assumptions about potential marketing success have often proven incorrect.

Why did DraftKings stop running Super Bowl ads for two years?

Robbins explains that after several years of consistent Super Bowl advertising, they decided to take a break. This year, however, their renewed partnership with NBC has allowed for more creative integration with the broadcast, making them excited to return to Super Bowl advertising. He emphasizes the need to adapt and innovate in marketing strategies, especially in high-visibility events like the Super Bowl.