The Examined Life

From playing online poker to pay for college, to starting a gardening lifestyle business that turned into a $40 million empire, Kevin Espiritu’s journey is jaw-dropping. He provides a candid look at his obsessive personality trait that fueled his success, and discusses his changing relationship with money as his business scaled. We cover following your passion, playing "the game" and finding fulfillment beyond just financial rewards. [Episode 54]

Learn more about Kevin:

• Kevin's Website

• Epic Gardening

• X/Twitter

• LinkedIn

• Instagram

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Podcast art by Nate Kadlac, photography by Henry Thong

Author Geraldine DeRuiter reached the dizzying heights of publishing her first book, then experienced the more muted satisfaction of her second. She’s grappled with the realization that external achievements can't resolve core belief of not being "good enough." We contemplate the limitations of external accomplishments in solving our deepest insecurities and the importance of recognizing and appreciating moments of success, even as the goalposts continually move. We cover the profound impact of childhood experiences on our adult drives and fears, the double-edged sword of ambition and the transformative power of vulnerability and human connection. [Episode 53]

Learn more about Geraldine:

• Geraldine's Website

• X/Twitter

• Instagram

• Meta Threads

References from the show:

• ⁠All Over the Place: Adventures in Travel, True Love, and Petty Theft⁠

• ⁠If You Can't Take the Heat: Tales of Food, Feminism, and Fury

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Podcast art by Nate Kadlac, photography by Henry Thong

When I was 22 years old, I worked 100 hours a week as an investment banker on Wall Street. I daydreamed about the day when I could retire, move to the beach and surf every day. When the board meeting would become the board meeting. That day came at age 35. I didn't retire or hit my "number." But I had enough to make a bold pivot and say, "Okay, now it's time to live life on my own terms." There were lessons learned along the way, and I'll discuss questions like, was it worth it? Is it risky to go all in on a passion? And what can surfing teach us about finding happiness in life? [Episode 52]

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Podcast art by Nate Kadlac, photography by Henry Thong

Do you feel like AI is a solution in search of a problem? I used to feel the same way. ChatGPT was basically a glorified search engine for me. I'd ask it things like "how do I make the fluffiest pancakes?" But after talking to AI expert Dan Shipper, I realized I was just scratching the surface. Dan showed me how to use AI to negotiate with vendors, understand dense books, compress information into tweets and so much more. [Episode 51]

Learn more about Dan:

• Dan's Instagram

• Dan's X/Twitter

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Podcast art by Nate Kadlac, photography by Henry Thong

Death is scary. We don't want to think about the infinite unknown. And being a speck not more than star dust. But what if contemplating death is the way you live a fuller, more purposeful and happy life? [Episode 50]

• Maura's X/Twitter

References from the show:

• The Denial of Death by Ernest Becker

• The Five Invitations by Frank Ostaseski

• A Beginner's Guide to the End by Dr. BJ Miller

• The Lily House

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Podcast art by Nate Kadlac, photography by Henry Thong

2015. German Chancellor Angela Merkel was the Person of the Year, Instagram Stories didn’t exist and Uptown Funk was the most popular song in the country. And I left Wall Street with a newborn daughter and no real plan. In the past 9 years, I’ve learned about money, envy, simplicity and relationships. And I want to share all of it with you. [Episode 49] 

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Podcast art by Nate Kadlac, photography by Henry Thong

Imagine being unable to afford a cup of coffee in your 20s. Then being able to afford the entire coffee shop in your 30s. Some “money issues” may arise — particularly for the next generation. Michael Perry had a big exit to Shopify but describes his struggles with self-hatred, not showing up well as a dad and helping his kids become resilient and kind humans. [Episode 48]

• LinkedIn

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Podcast art by Nate Kadlac, photography by Henry Thong

5% of Americans are in open relationships. I used to think that this world was for hot 20-somethings frolicking around house parties. Whether it’s open marriages, swinging or polyamory — the taboo is lifting and trend is definitely coming to a gentrified neighborhood near you. What’s most fascinating? For these relationships to succeed, you need a strong sense of self, the streak of non-conformity and deep trust in your partner. [Episode 47]

Suzi Sosa is a serial entrepreneur.

Learn more about Suzi:

• Suzi's Instagram

References from the show:

• How did polyamory become so popular?

• Polyamory, the Ruling Class’s Latest Fad

• Mating in Captivity by Esther Perel

• Sex at Dawn by Christopher Ryan

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Podcast art by Nate Kadlac, photography by Henry Thong

My wife and I did a guided psychedelic journey together. It was fully-assisted and we put on sleeping masks and went inward. It showed me so much about my emotional distancing, inner critic, people pleasing tendencies and why deep inside I’m nothing but a squishy loveball.

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Podcast art by Nate Kadlac, photography by Henry Thong

The traditional way of getting a great job is being turned upside down. Social media, personal brands and a digital portfolio of work now play a key role in landing your dream job. Today’s guest has harnessed both paths. He’s a Columbia MBA grad starting a new division within RobinHood. He’s also the world’s greatest LinkedIn shitposter. You’ll learn about networking online, the power of satire and how to de-risk a sabbatical. [Episode 45]

REFERENCES FROM THE SHOW

▸ How I Lost $150K in a Day

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Podcast art by ⁠Nate Kadlac⁠, photography by ⁠Henry Thong