Underdog was looking for a fresh, genuine way to engage a wider audience on social media to boost visibility, engagement, and new user acquisition efficiency. To do so, they turned to their long-lasting relationship with Bryson. Previous integrations with Bryson had proven that there was audience overlap and an appetite from Underdog fans for content featuring Bryson. Bryson’s original hole-in-one challenge in 2024, was an organic moment, and the Underdog team wanted to replicate that in a way that felt authentic while seamlessly incorporating a brand partner — which was a very difficult task. The teams found balance by launching a second challenge, with Underdog as the exclusive brand sponsor.
Starting on August 25, Bryson aimed to hit a golf ball over an Underdog-branded 2025 Bentley Continental GT, parked in his living room, into a mini Solo Cup each day, with shot attempts increasing each day. Around the target, there was an outlined Underdog Zone, and every time a ball landed in that zone, Underdog gave $100 in credit to one person using code BRYSON when signing up. After successfully making the shot on Day 12, Bryson gave away the Underdog Bentley to one randomly selected viewer who tuned in on social media.
The main priority for the Underdog team was to preserve the authenticity of Bryson’s normal content in the campaign, keeping it from being overly scripted or produced. The Underdog team worked with Bryson’s team to integrate the brand and the product in a way that was effective but not overbearing. This included reinforcing the floors of Bryson’s house to get the Underdog Bentley inside for the duration of the contest, in order to maintain the down-to-earth feeling of the daily videos. This process alone was extremely challenging but ultimately worth it, as the car being featured in every video inside the house was a smash and served to increase the virality. To incorporate the brand further while making the content interactive for the audience, the Underdog Zone was created to draw viewers in and keep them on their toes in an impactful but logical way.
There were also elements the team had to trust Bryson on, namely that he was indeed going to make the shot. Based on the size of the “cup” it seemed impossible (it was more like a shot glass), but Bryson made it work. His team, which has grown his YouTube page to the most powerful in the space, was also instrumental in designing a concept that was sure to engage his existing audience.
The daily releases at noon for twelve days built a routine for the audience waiting to see if he made the shot, if they’d won $100 on Underdog, or ultimately if they won the Bentley. This added another layer of interest to the promotion and differentiated it from the 2024 version. That routine helped bring in a huge number of views and conversions to customers.
This promotion was Underdog’s largest partner-driven acquisition effort ever, resulting in large-scale awareness and tangible user growth, meeting their goals to boost visibility, engagement, and new user acquisition efficiency. It led to a total of 141M views across 5 platforms:
The contest also led to organic earned coverage from national news outlets like golf.com, Golf Digest, Covers.com, TMZ, and others, reaching an even wider audience.