How Success Happens

Latest Episodes:

Mrs. Dow Jones Wants You to Buy that Latte Apr 30, 2026

Show notes

Haley Sacks, aka Mrs. Dow Jones, just dropped her first personal finance book and celebrated by buying a gold watch. Which, honestly, tracks. Her whole deal is that you shouldn't deprive yourself. Forget the strict budget. Haley's method is about finding ways to make more money, not suffering through life one skipped latte at a time. Pre-order her new book Future Rich Person.

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Snack Break: Free Comic Book Day Apr 26, 2026

Show notes

Free Comic Book Day is May 2nd (mark your calendars, people). To celebrate, Dan sat down with Sean Mackiewicz, Senior VP and Publisher of Skybound Entertainment, to talk about why giving away your best stuff for free is actually a genius long game, and how Sean is out here beating doctors and lawyers at career day.

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Bobby Berk: From High School Dropout to Queer Eye Star and Successful Entrepreneur Apr 22, 2026

Show notes

Bobby Berk dropped out of high school at 15, got fired from Bed Bath & Beyond for faxing his resume on the company fax machine, and somehow built two successful companies before becoming an Emmy-winner with Queer Eye. He stops by to talk about toxic workplaces, building something from nothing, and why kindness is a legitimate business strategy. Also, he picks Dan a paint color. Dan is going with it. Dan will blame Bobby if it looks terrible.

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Snack: Media Strategy Expert Zach Rosenfield Apr 19, 2026

Show notes

PR is one of those things everyone knows they need and almost no one knows how to get right. Dan sits down with Zach Rosenfield, CEO and President of RMG, the media strategy firm responsible for introducing Dan to guests like Daymond John and Shaquille O'Neal, to talk about how Zach built his business and, more importantly, how you can find the right PR team before you waste a dime on the wrong one.

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How Putting a Dog in a Backpack Turned Into a Business Apr 15, 2026

Show notes

Bryan Reisberg started carrying his corgi Max around in a backpack, because of course he did. The internet, predictably, lost its mind. Brand deals followed. Then a backpack line. Now supplements. In this episode, he talks about how he launched her career and stays relevant in a competitive space.

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Snack: Record Store Day Apr 12, 2026

Show notes

In 2008, Michael Kurtz joined forces with the band Metallica to try to bring back vinyl. Now, Record Store Day is a massive celebration that includes some of the biggest names in pop music. And the vinyl industry has become a billion-dollar industry for the first time ever, selling more records than when analog was the only choice. Michael Kurtz shares how the heck that happened.

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Naked Gun Writers on Pitching Your Wildest Idea Apr 08, 2026

Show notes

Dan Gregor and Doug Mand are part of the writing teams behind The Naked Gun, Crazy Ex-Girlfriend, and How I Met Your Mother. These guys know how to make people laugh. But being funny is only half the battle. Over the years, they've also figured out how to walk into a room, read it, and actually get a project sold. In this episode, they share their strategies for selling a pitch and what happens when it all goes wrong.

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Snack Break: Eva Longoria Apr 05, 2026

Show notes

Eva Longoria does so much it makes you want to lie down. Soccer. Tequila. She has a whole business empire that she apparently built while also running a foundation mentoring Latinas in entrepreneurship. Oh, and there's that little acting and directing career, too. She sits down with Dan to talk entrepreneurship, why she teamed up with Lenovo on their Backing Every Business program, and delivers a pep talk that frankly none of us deserve but all of us need.

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Berner on Cookies and Cancer Apr 01, 2026

Show notes

Berner built one of the most recognized cannabis brands on the planet while battling litigation and a colon cancer diagnosis at 38. He sits down with Dan to talk about community building and the lessons behind his new book, Becoming Legend.

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Snack Break: Novelist Emma Straub Mar 29, 2026

Show notes

Dan is looking for a little inspiration himself, so he called in a ringer: novelist, bookstore owner and all-around overachiever Emma Straub. She talks about how she knows when an idea is worth a year-plus of her life, what she learned about the writing game from her dad Peter Straub's good buddy Stephen King, and the hardest part of running two Brooklyn bookstores. Spoiler, it's not the books. Emma's hilarious new book American Fantasy hits shelves April 7th.

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