Any time an interviewee makes me ask my boss, “Can we say that in a newsletter?” you know it’s gonna be a good day.
Today, we’ve got spicy takes and spicy language from a master of marketing who made his fortune selling spicy shorts.
Lesson 1: Don’t get hooked on the performance marketing drug.
Preston Rutherford openly admits that he made every mistake in the book when co-founding the shorts company Chubbies.
So I kick off our chat by copping a line from Sheryl Crow: “What’s your favorite mistake?”
“Favorite mista-a-ake.” He sings, then laughs. “Favorite. Obviously a euphemism for gut-wrenching and sleep-depriving mistake. But, just to honor Sheryl…”
He thinks a moment: “Getting hooked on the drug that is short-term performance marketing — and in particular return on ad spend (or ROAS), where effectively all of our marketing investments were evaluated on that basis.”
My eyebrow goes up. Most marketing leaders want to see a measurable, proven return, right? How else do you know what’s working?
Rutherford says that exact sentiment is why he (and so many marketers) over-rotated toward performance marketing. That drive to make all of your marketing efforts systematic, measurable, and scalable.
“ We’re so used to a certain feedback loop on the data side, right? If I’m spending dollars, I’m only measuring success by who clicked on my ad and purchased in a 24-hour period.”
But that feedback loop incentivizes marketing efforts that produce short-term results — at the cost of long-term brand building. Not to mention, it led him away from all of the fun and unusual things that made Chubbies recognizable in the first place.
And what’s worse, the hypertargeting of performance marketing means “you’re spending dollars to claim a purchase that would have already happened.”
But if you’re not focusing on return, what are you focusing on?
“Brand is the most important asset that any kind of business builds,” he says. “And is ultimately the least measurable with current tools.”
Rutherford’s hot take? Only 40% of your marketing dollars should be spent on short-term ad spend, with the rest going to brand building.
“You would much rather have someone come directly to you — not being prompted by some kind of promotion or false urgency — but rather, ‘this is just a company that I believe in’.”
Lesson 2: If content is king, difference is queen.
“What marketing trend needs to die in a fire?” I ask him.
“Generative AI,” he blurts without a moment’s pause.
Y’all. I bark-laughed. (Then I wondered if anyone in my reporting hierarchy reads the newsletter, and nervously tugged my collar like Rodney Dangerfield.)
“Creativity is queen. Things that are different are queen,” he explains. “Generative AI is trained on models of what has already been done in the past and what has ‘worked.’”
He puts that last word into air quotes. According to Rutherford, this creates two problems: “Only looking backward and, in my opinion, an incorrect definition of what works. It’s based on driving short-term revenue.”
Rutherford is quick to qualify that this doesn’t mean there isn’t any place for AI in marketing. But for many marketers, it will lead to churning out what he calls “the sea of sameness.”
Breaking out from that “sea of sameness” is how Chubbies was born in the first place. When Rutherford and his friends sported the handmade shorts on vacation, the unusual cuts and colors had complete strangers approaching them to comment. Not everybody loved them, but everybody noticed them.
That success would have never been realized if they had based their decisions on what already worked.
Lesson 3: Think of marketing like building friendships.
Lesson 3: Think of marketing like building friendships.You’re probably thinking this lesson is gonna get all touchy-feely. Nope. This is a much more cuss-laden concept.
Rutherford says that any idea, tactic, campaign, or concept he has absolutely must pass through this filter:
“Would I send this email to a buddy or would they talk shit to me?”
For the third time in 15 minutes, I’m doubled over in laughter, but Rutherford has an excellent point. Stop and think about your favorite brands. They’re probably the ones that talk to you like a human being.
That doesn’t necessarily mean you have to be funny, irreverent, or uncouth. But I guarantee you didn’t think of someone who blasts you with corporate-speak.
Because at the end of the day, brand building is actually relationship building. That relationship will look different if you’re selling hot sauce, tax software, or maternity pillows — but they all require authenticity… and respect.
“Am I treating the people who view my ads like I’m a corporation marketing to faceless customers? Or am I a person marketing to other people?”
As proof, he points out that this is exactly why influencer marketing is so effective right now. It’s a real person talking to you as another real person. And our recent survey data bears out the same story as marketing leaders are pouring heavy budget into creator content, brand building, and developing authenticity.
Rutherford then drops a sweary little denouement: “People can see through our bullshit. People are not idiots.”
