A former journalist turned reluctant podcast host, still convinced he’s destined for something bigger while clinging to the idea that the world just hasn’t recognised his brilliance yet.
Quick facts
Age: 51 Date of birth and star sign: 7 March 1960 (Pisces) Pisces are known for their introspection, emotional depth, and tendency to get lost in their own world. Bob embodies the overthinking side, always believing he’s destined for something bigger. Hometown: Boston, Massachusetts Current location: New York City Occupation: Broadcaster, journalist, reluctant podcast host
Favourite brands and bands
“Banana Republic is classic, put together, and no-nonsense. I’ve been wearing it for years, and it still does the job. My Cadillac DeVille has been on the road for 15 years, and it’s still going strong. They don’t make them like they used to. And the Boston Red Sox? That’s loyalty. Through the highs and lows, you stick with what matters. As for music, give me something solid—Tom Petty, The Eagles, Bruce Springsteen. No gimmicks, just real music.”
Bob values what’s familiar. He doesn’t chase trends, and he believes in reliability over reinvention. His style is steady, professional, and unchanged for over a decade—not out of nostalgia, but because he sees no need to fix what isn’t broken. He listens to MOR rock for the same reason—it’s dependable, straightforward, and speaks to a time when things made sense. His 1997 Cadillac DeVille is another example of his reluctance to move on, a car he insists is still the best thing on the road. His loyalty to the Boston Red Sox runs just as deep; to him, tradition matters more than trends. If something worked before, it should still work now, and that’s how he approaches everything—from clothes to cars to the way he sees his own career.
Backstory and history
Bob was raised in a middle-class family in Boston, where ambition and hard work were everything. From a young age, he dreamed of being a hard-hitting journalist, picturing himself at the centre of political debates. He started in local radio, working his way up to news commentary, always believing he was one step away from national recognition. But that next step never came.
In his thirties, he had a brief affair with his co-host, Jane Hart, but ruined it when he slept with the weather reporter. Jane moved on, but Bob stayed stuck, still convinced his career-defining moment was just around the corner. Now, hosting a branding podcast feels beneath him, though he justifies it as a way to stay in the industry. Deep down, he knows this isn’t what he wanted.
Personality and quirks
Bob sees himself as a serious broadcaster, a man who should be debating politics, not reviewing books on branding. He talks too much, explains things that don’t need explaining, and assumes his perspective is always the most informed. He dresses like he’s still on television—button-up shirts, blazers, polished shoes—but there’s always something slightly undone about him, like he’s trying to maintain control but never quite succeeding.
Despite his ego, he still wants to be liked. He has an underlying insecurity that he refuses to acknowledge, a lingering fear that he peaked years ago and is now just coasting. Jane is the only person who truly unsettles him, and he’d never admit how much he respects her.
Biggest challenge and personal struggle
Bob’s biggest challenge is himself. He refuses to accept that he’s not destined for greater things, still convinced that his real career is just one break away. He struggles with Jane’s presence, knowing she has moved on while he is still stuck in old patterns.
What drives him
Bob wants recognition, respect, and a return to serious journalism. He sees the podcast as a temporary side project but secretly hopes it leads to something bigger. He tells himself that success is still coming—it’s just taking longer than expected.
What he’s good at (and not so good at)
Bob is articulate, knowledgeable, and thrives in debate. He knows how to construct an argument, even if he sometimes loses sight of the point. He’s good at appearing confident, even when he’s unsure.
He’s less good at listening, adapting, or realising when he’s out of his depth. He struggles to admit when he’s wrong and over-explains when he feels challenged. His biggest weakness is his ego—his inability to let go of the past keeps him from fully embracing the present.
What he stands for
Bob believes in the power of journalism, structured debate, and intellectual discourse. He values perception and reputation, sometimes more than the truth itself. He believes success is earned, but he struggles with the fact that he hasn’t achieved what he expected. His biggest contradiction is that he respects authenticity but spends most of his time trying to prove himself rather than just being himself.
The heart of Bob
Overthinking, self-important, restless
Fun details
Can’t live without? A leather-bound notebook, filled with half-formed ideas for “better” projects than this podcast. He carries it everywhere, convinced he’ll use it to map out his real comeback.
Theme song for life? “The Boys of Summer” by Don Henley. Nostalgic, reflective, and just self-important enough to feel profound, it’s a song about chasing something that might never come back.
Go-to drink at the pub? A neat whiskey, because he thinks it makes him look distinguished. In reality, he orders it more for the image than the taste, but he’ll never admit that.
