Before taking a pause for the Summer, Carl revisits moments with recent guests Austin Kleon, Debbie Millman, Tom Fishburne, and Gretchen Rubin to pulling together common threads about the hidden stories we tell ourselves about money. Ask yourself the following questions while listening: Where does your money come from and what does it cost you? What stories are you believing about money, and are they even true? The answers to these questions may help you start writing a new story about money. 

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Cover Art: Josh Passler - TheFinArtist.com

Music Credits: 

Alexandra Woodward / Rabbit Reggae / courtesy of www.epidemicsound.com

Cody Francis / Wherever You’re Going / courtesy of www.epidemicsound.com

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Austin Kleon has built a life around making art—and making choices. In this candid conversation, the bestselling author of Steal Like an Artist opens up about the cost of creativity, the pressure of success, and the freedom that comes from knowing what’s enough. From turning down life-changing sums of money to driving an old Honda with pride, Austin reflects on how his values have shaped both his art and his bank account.

Austin and Carl explore the emotional and financial tradeoffs of creative work, what it means to stay grounded in a world obsessed with growth, and how money can be both a stabilizer and a source of chaos. Austin also reveals the question he’d ask if money were a person—and why he still wrestles with switching from a mindset of scarcity to one of sufficiency.

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Cover Art: Josh Passler - TheFinArtist.com

Music Credits: 

Alexandra Woodward / Rabbit Reggae / courtesy of www.epidemicsound.com

Cody Francis / Wherever You’re Going / courtesy of www.epidemicsound.com

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Cartoonist and former brand manager Tom Fishburne—best known as the creator of Marketoonist—joins Carl for a conversation that flips the script on what it means to take risks. From leaving a stable job with a Harvard MBA to becoming a full-time cartoonist, Tom shares what looked like “career suicide” from the outside became his most stable and fulfilling path.

They explore the quiet financial anxiety of childhood, the lessons Tom learned from his mom’s late return to college, and a pivotal year spent in Prague that sparked a lifelong entrepreneurial mindset. Along the way, they talk about the voices of self-doubt, the myth of the “safe job,” and the courage it takes to build a purposefully small, soulful business.

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Cover Art: Josh Passler - TheFinArtist.com

Music Credits: 

Alexandra Woodward / Rabbit Reggae / courtesy of www.epidemicsound.com

Cody Francis / Wherever You’re Going / courtesy of www.epidemicsound.com

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Debbie Millman is a celebrated designer, writer, educator, and host of the long-running podcast Design Matters. In this conversation, Debbie opens up about a subject she rarely discusses publicly: her lifelong relationship with money.

Together with Carl, she traces the roots of scarcity, shame, and control that shaped her childhood and career decisions—from hiding candy in a handbag as a little girl, to working three jobs to ensure she'd never need to depend on anyone. She reflects on how money became synonymous with safety, and shares the surprising realization that no amount of wealth can truly provide the security we seek if we don’t already feel safe within ourselves.

They also discuss Debbie’s transformative 10-year vision exercise, the power of clarity in goal-setting, and why even our biggest accomplishments can lose their luster fast. A powerful exploration of what “enough” really means.

Follow 50 Fires on Instagram: https://www.instagram.com/50firespod/

Please direct business inquires to: [email protected]

Cover Art: Josh Passler - TheFinArtist.com

Music Credits: 

Alexandra Woodward / Rabbit Reggae / courtesy of www.epidemicsound.com

Cody Francis / Wherever You’re Going / courtesy of www.epidemicsound.com

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"You Actually Miss Your Life While You're Trying to Protect It". That’s the provocative idea at the heart of this episode with bestselling author Oliver Burkeman (Four Thousand Weeks). Oliver reflects on how class, money, and time shape our identity and our illusions of control. From childhood popsicle enterprises to awkward dinner bills and the haunting anxiety of spending money in the present, the discussion digs deep into the emotional undercurrents of financial life. No tidy answers, just honest questions.

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Read Oliver’s Writing: oliverburkeman.carrd.co  

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Follow 50 Fires on Instagram: https://www.instagram.com/50firespod/

Please direct business inquires to: [email protected]

Cover Art: Josh Passler - TheFinArtist.com

Music Credits: 

Alexandra Woodward / Rabbit Reggae / courtesy of www.epidemicsound.com

Cody Francis / Wherever You’re Going / courtesy of www.epidemicsound.com

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Is money ever just about money? Gretchen Rubin, bestselling author and happiness expert, joins Carl to explore the subtle ways our childhood, identity, and and the surprising power of choosing what not to spend money on. From her awe at the simple amount of $100 as a child to the moment she chose not to renew her New York Bar license, Gretchen shares how she made peace with desire, comparison, and her own financial narrative along the way. 

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Follow Gretchen @gretchenrubin 

Listen to Gretchen’s Podcast Happier with Gretchen Rubin wherever you listen to podcasts. 

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Follow 50 Fires on Instagram: https://www.instagram.com/50firespod/

Please direct business inquires to: [email protected]

Cover Art: Josh Passler - TheFinArtist.com

Music Credits: 

Alexandra Woodward / Rabbit Reggae / courtesy of www.epidemicsound.com

Cody Francis / Wherever You’re Going / courtesy of www.epidemicsound.com

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What happens when you’ve checked every financial box—and still feel lost? Carl sits down with comedian, former Facebook exec, and Reasonably Happy author and podcast host Paul Ollinger to explore the emotional weight of money and identity.

Paul shares what it felt like to walk away from Silicon Valley at 42, why he once considered himself a "rich loser," and how chasing fulfillment led him back to the stage as a stand-up comedian. They unpack the psychology of wealth, the shame and status we attach to our financial lives, and why we often struggle to say, “I have enough.”

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Follow Paul @paul_ollinger 

Listen to Paul’s podcast Reasonably Happy

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Follow 50 Fires on Instagram: https://www.instagram.com/50firespod/

Please direct business inquires to: [email protected]

Cover Art: Josh Passler - TheFinArtist.com

Music Credits: 

Alexandra Woodward / Rabbit Reggae / courtesy of www.epidemicsound.com

Cody Francis / Wherever You’re Going / courtesy of www.epidemicsound.com

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Identity, belonging, and the real meaning of money and Judaism is covered in this episode with Rabbi Shira Stutman. Rabbi Shira and Carl navigate questions of tradition and community in today’s polarized world, the need to hold space for complexity—within ourselves and our institutions—and how embracing discomfort can spark growth, understanding, and ultimately, a stronger sense of purpose.

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Follow Rabbi Stutman @shirastutman 

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Follow 50 Fires on Instagram: https://www.instagram.com/50firespod/

Please direct business inquires to: [email protected]

Cover Art: Josh Passler - TheFinArtist.com

Music Credits: 

Alexandra Woodward / Rabbit Reggae / courtesy of www.epidemicsound.com

Cody Francis / Wherever You’re Going / courtesy of www.epidemicsound.com

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Is money dangerous? Could be. Is money powerful? Definitely. Can it corrupt? Of course. Can it liberate? Absolutely. Money is a mirror.

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Follow 50 Fires on Instagram: https://www.instagram.com/50firespod/

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Cover Art: Josh Passler - TheFinArtist.com

Music Credits: 

Alexandra Woodward / Rabbit Reggae / courtesy of www.epidemicsound.com

Cody Francis / Wherever You’re Going / courtesy of www.epidemicsound.com

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Breanna Rae Blainey is a financial wellness leader, entrepreneur, and co-founder of the Anya Institute for Human Revolution. She and Car unpack themes like control and the emotional energy we attach to our finances, offering practical tools like the "Triple A" framework—awareness, alignment, and action—to help navigate our relationship with money in a more intentional, values-driven way.

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For more on Breanna, visit https://www.breannaraeblaney.com/

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Follow 50 Fires on Instagram: https://www.instagram.com/50firespod/

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Cover Art: Josh Passler - TheFinArtist.com

Music Credits: 

Alexandra Woodward / Rabbit Reggae / courtesy of www.epidemicsound.com

Cody Francis / Wherever You’re Going / courtesy of www.epidemicsound.com

Learn more about your ad choices. Visit megaphone.fm/adchoices