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 fin...

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 recogni...

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...

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 i...

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 is the founder of Hello Mortal a platform dedicated to familiarizing us with the great unknown. Learn more about Maura: • Maura's X/Twitter References from the show: • T...

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]  —- JOIN OUR GROUP COACHING COHORTS: Are you...

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] Michael Perry is the fath...

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...

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. [Episode 46] —- JOIN OUR GROUP COACHING COHORTS: Are you looking to ask deep, introspective and provocative questions about yo...

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 an...

The Internet has created a gold mine of opportunity. You can use it to find your next job. Or business idea. The crazy part is that people are telling you — through Google searches, Reddit Posts and social media — what they actually care about. And you can use that information to come up become an idea machine. [Episode 44] Steph Smith is a growth marketer, indie creator, and data fanatic. She cur...

I’ve been told I look Brazilian, Greek and Hawaiian. I relished it because I didn’t want to be called Asian. Especially not in 80s and 90s, where the stereotypes of docile nerds (who like math and kung fu) reigned supreme. Now at age 44, not only are Asian men having a “moment” — I’ve gone inwards to reevaluate my identity, heritage and how this has catalyzed a new lens on service. [Episode 43] —-...

Going to therapy usually evokes laying on a couch and talking endlessly about your childhood. But what if all the stress and healing are located in your body and could be felt and accessed through your inner monologue. That’s the approach of Internal Family Systems (“IFS”) which helps you tap into your various “parts,” like your Inner Critic, Perfectionist or Lone Ranger to better understand yours...

Do you take parenting at face value? Obviously, no — but when was the last time you questioned the assumptions? In this interview, we discuss the “unconventional approach” to parenting. One that doesn’t helicopter, that recognizes that the parents themselves are flawed and focuses on raising emotionally resilient kids. [Episode 41] Ted and Franzi Gonder are entrepreneurs, coaches and deeply intent...

I left my "peak earning" years to focus on fatherhood. The financial sacrifice was huge but 10 years later I test to see if this was the right decision. I cover trade-offs, parenting when you're rich and how to instill grit and resilience into your kids. [Episode 40] References from the show: • One day, you’re no longer their favorite person • Are ambitious parents bad parents? • Can...

I got entrepreneurship backwards. I thought it was all about writing business plans and doing market research. Serial Entrepreneur Noah Kagan sets me straight and drops wisdom bombs for anyone looking to leave their 9-to-5. We discuss facing rejection, understanding customer needs, to embracing the courage to ask and push boundaries. [Episode 39] Noah Kagan is a serial entrepreneur who founded App...

Ambition is a good thing, right? It’s your ambition that creates opportunity. It grows your income. It makes you visible and relevant. But is it also insatiable? We explore the dark side of ambition: burnout, broken relationships and ignorance. [Episode 38] Amanda is a serial founder, brand builder, creator and single mother of three. Learn more about Amanda: • Amanda's LinkedIn , X/Twitter ,...

I’ve invested a ton of money into coaching. ($163,900 to be specific.) I’ve used coaching to face my insecurities, overcome scarcity thinking, become a better father and husband and make sense of my purpose on this earth. Khe provides an in-depth analysis of his experience with 12 different coaches. [Episode 37] Listen to Khe get coached by: • His first coach, Kate Bednarski • Joe Hudson from Art...

The economy is soaring. Stocks are at all time highs. Inflation has been tamed. Yet young people are angry and anxious. This episode isn’t about “OK Boomer” inter-generational warfare — it’s about trying to understand the angst driven by economic inequality, the blowback from the “attention economy” and social media-induced loneliness. [Episode 36]  Kyla Scanlon is a financial commentator and auth...

When you think of creativity, what comes to mind? Maybe it’s a disheveled Earnest Hemingway writing in a cafe in Spain. Or a prolific artist like Beyoncé who churns out hit after hit and sells out stadiums. But every single human being is a creative being. Creativity is about how you solve problems, how you put yourself out there and how you translate ideas into businesses. [Episode 35] Jeffrey B....

It’s bonus season. Are you thinking of making that big move? And finally walking away from your cushy, high-paying job? Khe gives you a preview of everything you’d expect including the marital strife, the overspending and the “identity earthquake.” [Episode 34] References from the show: • Making an Angel Investment in Yourself • Why Really Rich People Worry about Money • How to Survive an Identity...

As your earnings go up, your ability to enjoy money should increase as well. And you should worry less. Yet somehow, high-earners still struggle to do both. Adam Katz is a wealth advisor at Corient. Khe and his wealth manager discuss Die With Zero, using leverage, return on hassle and the myth of “The Number.” [Episode 33 ] Disclosure: Adam is Khe’s advisor and this podcast does not contain invest...

The first 3 years of your life deeply impact how you interact with the world around you. We develop attachment strategies to feel seen, safe and loved. How do these behaviors impact us as adults? We discuss the implications on talk therapy, healing through meditation and how to apply attachment theory to parenthood. [Episode 32] Jess Morey is a meditation teacher and contemplative coach. Learn mor...

Are you a Post-Achievement Professional? For starters, this doesn’t mean that you no longer care about striving and achieving great things in your career. Instead it’s a redefining of your relationship with Achievement — a reckoning of sorts that it can only take you so far in the pursuit of fulfillment and happiness. --- I’m leading a salon (fancy, I know!) on the path to becoming a Post-Achievem...

Playing the “net worth” game puts you on the never-ending hamster wheel of never hitting “enough.” In this episode we look at the myth of The Number, how unworthiness drives achievement and how to rebuild your identity outside of your bank account. [Episode 30] Manisha Thakor is a seasoned financial executive in wealth management. She’s the author of MoneyZen: The secret to finding your enough. Le...