Bad idea #4: Roasting Justin Bieber for the brand
We could all learn something from Martha Stewart about how not to play it safe.
She built her empire on the aesthetic of ironed table linens and carefully manicured gardens. Precision. Properness. Predictability.
Then she went to jail.
“I’m not a billionaire anymore,” she would quip later on a podcast. “Jail took care of that.”
(Weird aside: you can blame the ambitious James Comey for sending Martha to jail.)
When she got out of jail, she started the hard work of rebuilding her media empire. And one of the pivotal yet unlikely steps in that journey involved Martha saying yes to appearing on Comedy Central’s Justin Bieber roast.
She didn’t exactly fit the lineup. The stage was filled with athletes, comics, and professional shade-throwers like Snoop Dogg, Kevin Hart, Shaq, and Pete Davidson.
Her team told her it was a bad idea and tried to talk her out of it. Even her daughter, Alexis, weighed in with concern.
“Why are you wasting your time going to California to roast Justin Bieber?”she asked.
Exactly.
It was a sharp left turn from the cookie-cutter brand she’d built in the first half of her career on TV. Martha knew it was a departure, but she’d decided to take more chances and be herself after prison.
She’d never seen a Comedy Central roast before, and that probably made it easier to say yes. “I had no idea they would say such awful things about me on TV,” she later said. “I was able to laugh it off, as I can.”
And that’s the twist. She didn’t fold under the pressure. Her appearance stole the show as she delivered jokes from a cool, calm, and merciless demeanor.
“Let’s get to the reason I’m here tonight,” she told Bieber and a room full of surprised celebrities, “which is to give Justin Bieber some tips to use when he inevitably ends up in prison. The first thing you’ll need is a shank. I made mine out of a pin tail comb and a pack of gum. It’s so simple.”
Martha’s edge?
She’d spent more time on camera than anyone else on that stage, and it showed.
She was comfortable owning a room and owning the screen. Having recently acquired an IDGAF attitude may have also helped.
The roast wasn’t just an unexpected appearance. It was the perfect exclamation point for a reset to her career and public image. One that nobody foresaw, but that Martha’s “yes, and” attitude enabled.
As TIME put it…
“Call it an unexpected, welcomed turn from a star whose perceived image of chilly perfection has too long been ripe for mockery by others. That night, she took control of her image again and gave herself permission to be a realer version of herself.”
And it worked.
Another outcome from that night? The birth of Martha’s gloriously weird friendship with Snoop Dogg. The two would go on to co-host a cooking show, make dozens of appearances together, and build a friendship that redefined both of their brands.
Martha executed a sort of cultural jujitsu that no one could have predicted: evolving past her lowest moment (prison time, business decline) and reframing it as only a blip in her journey to a much richer cultural presence and impact.
The roast did what most down-on-their-luck celebrity brands find impossible… it made her cool again.
Not because she pretended to be someone else, but because she embraced who she was and volunteered as tribute for a public flogging that 99% of us would avoid like the plague.
We won’t all face prison time or fall out of the billionaire class like Martha, but everyone has down moments when the record skips a beat.
When that happens, trust your instincts, be the wildcard, and use your voice to be the honest version of yourself on stage. Taking a few hits doesn’t mean you’re out of the fight.
Art/Social/Ad
New ideas are born from brushing up against life, a process I call happy collisions. Here are a few pieces of inspiration to keep the ideas flowing: one piece of ART, one SOCIAL post, and one AD (or a bit of clever marketing).
ART
Every year, a Melbourne, Australia teacher makes stuffed toys for each of her 20-some students based on their “dream creatures” drawings. Put these in an NYC gallery and they’d sell for tens of thousands. Follow the link for more creatures.
SOCIAL
A great Sanderson quote and a good reminder to own your art.
AD
“Pope yes” by @Popeyes, maybe the most perfect brand social post of all time.
I don’t even have to read this and already love the angle.