Facing Down Trump with Jocelyn Benson

Facing Down Trump with Jocelyn Benson

Author: Paul Ollinger May 30, 2025 Duration: 45:15
In December 2020, Michigan Secretary of State Jocelyn Benson was decorating the family Christmas tree with her 5-year-old son when she heard a crowd outside her home chanting "Stop the Steal!" In the days and weeks that followed, Donald Trump harassed her on social media, calling for her arrest and accusing her of treason, Benson alleges.On this week's Reasonably Happy podcast, Benson--who is now running for governor--joins Paul Ollinger to discuss how she modernized the DMV, what it feels like to be targeted by the President of the United States, and why the Democrats' murky future. Paul pushes her to take a stand against a party that keeps falling on the sword of cultural issues with which most of America disagrees, opening the door for the very President who tried to intimidate her. Unfortunately, Benson waffles on subjects like biological males in girls' sports and the fact that most college campuses have been captured by progressive ideology. Still, it's an interesting conversation with a rising political star who, if she can stand up to her party the way she stood up to Trump, could be a solid mainstream candidate someday.Read Paul's Substack here: Http://words.paulollinger.com

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Paul Ollinger has worn a few different hats-stand-up comedian, tech executive, and now, the curious host of Reasonably Happy with Paul Ollinger. This isn't a lecture series or a dry self-help guide. Instead, it feels more like pulling up a chair for a series of genuinely engaging talks that wander into the places where our daily lives, careers, and inner worlds collide. The conversations, which feature authors, thinkers, and various creatives, are refreshingly candid. They dig into the practical and philosophical questions about what it actually means to build a life that feels both successful and satisfying. You'll find that each episode of this podcast approaches big themes-money, purpose, and the pursuit of contentment-with a blend of wit and thoughtful depth. The underlying idea isn't about finding a perfect, Instagram-ready version of happiness, but something more grounded and attainable. It's for anyone who's ever wondered if there's a smarter, more meaningful way to navigate the pressures of business and culture without losing sight of what matters. Tuning in, you get the sense that Paul is figuring it out alongside his guests, making the insights feel earned and relatable. The result is a consistently interesting exploration of how we can all aim for a life that feels reasonably, and authentically, well-lived.
Author: Language: English Episodes: 100

Reasonably Happy with Paul Ollinger
Podcast Episodes
I Read My Essays to You [not-audio_url] [/not-audio_url]

Duration: 35:59
✍️ Follow Paul Ollinger on Substack by clicking here ✍️Hello friends, this week's Reasonably Happy is me reading some of my favorite posts from my Substack over the past six months. They cover the Manosphere, schadenfreu…
5 Questions with Dave Barry [not-audio_url] [/not-audio_url]

Duration: 30:52
✍️ Follow Paul Ollinger on Substack by clicking here ✍️Oh my goodness what a fun time I had chatting with Dave Barry on the first episode of 5 Questions, my bite-sized, live-streamed Substack interview show that I’ll be…
Gretchen Rubin Will Teach You to be Happy [not-audio_url] [/not-audio_url]

Duration: 58:34
✍️ Follow Paul Ollinger on Substack by clicking here ✍️“Happiness is a choice that requires effort at times.” -Aeschylus Whenever I go back and re-listen to one of my podcast interviews, I always discover elements of the…
Money, Family & Comedy w/Roy Wood Jr. [not-audio_url] [/not-audio_url]

Duration: 56:44
✍️ Follow Paul Ollinger on Substack by clicking here ✍️My guest today is Roy Wood, Jr. You know him from The Daily Show and from his acclaimed stand-up specials, where he proves that smart comedy can still hit hard. A na…
How to Get Rich in America [not-audio_url] [/not-audio_url]

Duration: 1:06:04
✍️ Follow Paul Ollinger on Substack by clicking here ✍️“Capitalism is rigged!” cry the masses. “Nobody gets ahead anymore,” says the mainstream press. And 60% of young people believe that the American Dream is dead. But…
The Fragile Power of Wealth [not-audio_url] [/not-audio_url]

Duration: 47:24
If you’ve ever wondered if having everything you’ve ever wanted would make you feel like a complete human being, this episode is for you. My guest today is Dr. Paul Hokemeyer, a psychotherapist who works almost exclusive…
Surviving the Loss of a Child [not-audio_url] [/not-audio_url]

Duration: 1:04:01
“How am I ever going to be happy again?” That was the question the wife of this week’s guest asked him after the death of their one-month-old son, Fisher. Michael Cruz Kayne is a comedian, actor and a staff-writer on The…
Millionaires v. Billionaires in NYC [not-audio_url] [/not-audio_url]

Duration: 1:06:04
Chris Pavone is the bestselling author of some of the smartest and most stylish thrillers of the past decade. His latest book, The Doorman is set in a glamorous Manhattan apartment building where the lives of the ultra-w…
The Beatles, Ted Turner, and Ric Flair with Steve Chamberlain [not-audio_url] [/not-audio_url]

Duration: 1:01:25
This week’s podcast is a conversation with my former Atlanta neighbor, Steve Chamberlain, a former media executive whose career has intersected with some of the biggest brands and celebrities in entertainment history. I…
Money, Fame, and Misery: Meet the Beatles [not-audio_url] [/not-audio_url]

Duration: 58:00
Money, Fame, and Misery: Meet the Beatles (w/ Peter Doggett )In the late ‘60s, The Beatles had it all: worldwide fame, critical admiration, and more money than they ever could have imagined. So why were these four young…