In a world of instant attribution and short-term wins, most marketers are focused on what they can prove now. But in this episode of Beyond the Billboard, Greg Wise and Charlie Riley talk with Preston Rutherford, co-founder of Chubbies, about why lasting brands are built through more than just clicks and conversions.
Chubbies didn’t win by outspending the competition. They built something different, and this episode is packed with lessons for marketers who want to build a brand that lasts.
Watch the full episode below.
From Dorm Rooms to a National Brand
Chubbies was born during a cultural shift. Preston and his co-founders wanted to create something that made people feel good. It started as a side hustle built on nostalgia, humor, and anti-corporate energy.
“My boss is an idiot. I hate one on ones. I don’t have a mortgage. I’m not married. This is the time,” Preston said, reflecting on the mindset when starting Chubbies.
The product may have been shorts, but the real differentiator was the feeling they created. As Preston put it, “Our dads from the seventies and eighties looking freaking awesome, wearing the shorter shorts, the longer socks, having the mustache and the sideburns” helped shape the brand’s identity.
Brand Drives Profitable Growth
Chubbies was not just a viral moment. It became a real business because they invested in brand early.
“I think that is the power of investing in brands, sustainable growth that is profitable. I think this might be the fifth or sixth year of profitable growth, maybe more, seventh,” Preston shared.
That type of performance does not come from short-term thinking. It comes from creating demand over time and showing up consistently, even when buyers are not ready yet.
You Can’t Market Only to the 5 Percent
Preston made one thing clear. Most people are not ready to buy right now. Performance-only strategies tend to focus on people who were already going to convert.
“95 percent of people are not in market right now, so I can’t convince them of anything regardless of how many variants I tested on my direct response,” he said. “My job is to prep them effectively.”
That is where brand plays a critical role. It builds familiarity and trust long before someone clicks on an ad.
Marketing Needs to Get Smarter About Measurement
There is a false narrative that brand marketing is soft while performance marketing is data-driven. Preston challenges that idea.
“A couple ways to approach it, but I think the most effective way to talk about it is start with the soft, but connect it to the stuff that a CFO and everyone as a business operator needs,” he explained.
Marketers need to understand contribution margin, customer acquisition costs, and incrementality. Because if you are not driving new demand, you are just recycling what was going to happen anyway.
“Current tactics of performance marketing are unfortunately not doing that. They are just taking credit for purchases you would have gotten anyways, and we’re just spinning a wheel,” Preston said.
Demand Today and Demand Tomorrow
One of the biggest shifts Preston urges marketers to make is to zoom out. He says the goal is not a click. It is contribution dollars over time.
“Demand today, demand tomorrow. Just maximize contribution dollars per dollar spent over a twelve-month period, and you win. But it doesn’t show up from a click on an ad,” he said.
This is why out-of-home (OOH) advertising and other awareness plays are gaining momentum. They help build familiarity and trust for the 95 percent of people who are not yet ready to buy.
Final Thoughts: Don’t Ignore Brand
When you look at the growth of Chubbies, it was not just the shorts or the social media presence. It was the brand. A brand rooted in a clear identity, a strong emotional connection, and consistent messaging across all touchpoints.
OOH advertising helped amplify that identity. So did smart digital campaigns. But it all came back to brand.
“Who are already likely to purchase. So incrementality is going down and down,” Preston warned.
If you are still stuck in the cycle of chasing conversions from the same small pool of buyers, it is time to rethink your strategy.
🎧 Listen to episode 5 of Beyond the Billboard to hear more about how Preston built Chubbies into a brand that lasts. Learn how to connect your brand efforts to business outcomes and why thinking beyond the click is what really drives results.