The Examined Life

Are men becoming more in touch with their feelings? Or are they going the way of Andrew Tate’s brash aggression (and the accompanying vile)? We discuss how repressing anger impacts relationships and how fully feeling emotions reveals core wounds and the ability to set boundaries. [Episode 29] Scott is an executive coach who teaches emotional and relational intimacy. Learn more about Scott: Connect...

2023 was the year everything went wrong. Rising interest rates, return to office, a shaky consumer and the collapse of “doing things online.” After entering the year overconfident (and with too big of a team) we go humbled. And it rattled my confidence… yet me managed to turn things around. [Episode 28] —- JOIN OUR GROUP COACHING COHORTS: Are you looking to ask deep, introspective and provocative...

We worry about money. When there’s not enough, we’re scared of the catastrophe. When there’s too much — there’s always someone with more. Could it be that our rational brains can’t fully grasp the emotional complexities of money? What if worry, anxiety and comparison are just representations of our unmet desires? [Episode 27] Joe Hudson is a coach, teacher and facilitator at the Art of Acccomplish...

One of the most common complaints from high-performers? “I can’t turn off my brain.” So we turn to doomscrolling, alcohol and other substances. Tara Schuster used weed to cope — until she blacked out and left a terrifying voice message for her therapist. [Episode 26] Tara is a former executive at Comedy Central (Key and Peele, David Spade) and 2x best-selling author. This episode discusses suicide...

Networking gets a bad rap. It’s transactional, icky and insincere. In this solo episode, Khe reimagines the entire networking experience focusing it on service, curiosity and genuine care. And how he kept up the unimaginable pace of 1 meeting a day for 25 years. [Episode 25] If you’re looking to implement the CRM system check out the Life Operating system . --- REFERENCES FROM THE SHOW: Cringe-fre...

As a parent, you’re constantly nervous about raising spoiled, entitled and elitist kids. And if you're from a modest upbringing and have found success as an adult — it’s hard to recreate an environment of grit and resilience for your kids. We discuss exposing children to folks living in poverty, why “traveling” doesn’t give perspective and how to think about an inheritance. [Episode 24] Wil is...

[Ep. 23] You meet someone, they Google you. Are the results your personal brand? In a world where everyone is jousting for jobs, clients and partners — how important is your online presence? We discuss getting over the cringe, establishing thought leadership, playing the long game and putting the “social” back into social media. Shanté Cofield is a physical therapist turned entrepreneur who helps...

[Ep. 22] If you work 40 hours a week on your own terms, are you semi-retired? A solo episode where Khe describes “a day in the life.” He covers spiritual practice, being pre-diabetic, his struggles with chasing fame, an update on no drinking — and the mystery behind the abs. —- JOIN OUR GROUP COACHING COHORTS: Are you looking to ask deep, introspective and provocative questions about your own life...

[Ep. 21] Owning your time. Living close to nature. Rock climbing daily. Do you have to wait until “retirement” to enjoy these? Or can you uproot your family and move to your mountains in your 40s. We discuss the importance of where you live, opting out of status games, millionaires with no hobbies, visualizing your success, being a girl dad, pegging self-worth to net-worth, the trade-offs of VC-ba...

[Ep. 20] What happens when making money starts making you unhappy? You might dislike the activity. Or be bored. We discuss the “sunk cost fallacy,” the Identity Earthquake, discovering your aliveness and rebelling against what the gurus and textbooks say you “should” be doing. Sarah Chappell is a writer, strategist, and coach. Learn more about Sarah: Think Piece Newsletter The Think Piece Podcast...

[Ep. 19] High-performing teenage kids are considered an “at risk” group. Yup, they’re as likely as prone to substance abuse and depression as kids living in poverty or with incarcerated parents. How did we end up here? Don’t we just want what’s best for our kids? We look at this through the lens of parents and covering the role of status preservation, economic scarcity, needing validation, hyper-i...

[Ep. 18] Productivity is sold as the silver bullet to all our modern problems. Do a bit more. A bit faster. Squeeze in that last email. But what if productivity (and the entire self-help industry) is built on a shaky promise? What if it’s just distracting us from lives devoid of meaning or the inability to understand what makes us come alive? Nat Eliason is a writer, marketer, crypto investor and...

[Ep. 17] Are you scared that you’re one mistake from losing it all? We all experience some form of the scarcity mindset. This mindset warps money into our self-worth, our “enough-ness,” safety and security amidst the real (and imagined) risks out there. We look at climate change, our childhood numbing ourselves with consumerism/substances, childhood money stories and whether you actually need mone...

[Ep. 16] I became obsessed with productivity content in my 20s. Being “productive” was an accelerant for my career, finances and owning my time. But productivity falls short on teaching you what it means to lead a “well-lived life.” As we launch our last productivity course EVER, I share the entire course for free as a podcast episode. If you’re still interested after listening, sign up below: htt...

[Ep. 15] Why does listening to podcasts on “Chipmunk Mode” (aka 2x speed) feel so unhealthy — yet so attractive? We discuss the fight-or-flight tax, chronic stress debt, using alcohol to take the edge off, unhealthy career ambition and if aliveness and success are a zero-sum game. Jonny is a podcaster, instructor, coach and dog dad who’s passionate about emotional regulation. Learn more about Jonn...

Ep. 14 What’s really happening between the sheets? A s*xologist answers juicy questions about our sex lives. We cover the myth of 0rgasms during intercourse, s*x toys, performance anxiety, body issues, watching (ethical) p0rn with your partner, open marriages, swinging and how you can keep the passion as you age. Learn more about Natassia: Follow Natassia on TikTok Follow Natassia on Instagram Fol...

[Ep. 13] Khe tackles his 26 year history of drinking in this solo episode. You’ll hear about “Blackout Island,” being a functional heavy drinker, his favorite substances, the emotions he’s avoiding, drinking-related problems and his eponymous “Khe-garitas” (aka Skinny Margaritas). References from the show: When Things Fall Apart: Heart Advice for Difficult Times by Pema Chodron Why did Khe leave W...

[Ep. 12] Everyone claims to be playing “the long game,” but what does that actually mean? We discuss building genuine relationships, the unique traits of entrepreneurs, the difference between being rich/wealthy and how to spend in accordance with your values. Adam is a wealth manager for ultra-high net worth individuals in the tech and finance world. Learn more about Adam: Connect with Adam on Lin...

In this episode we discuss adult friendships and how they evolve with age including Aristotle’s 3 definitions of friendship, the time required to make new friends, how friendship gets deprioritized during the early stages of parenthood and how to create rituals to stay in touch. Kat Vellos is a designer, author, connection coach and speaker who helps people make and maintain friendships in adultho...

Is college (still) worth it? We discuss whether you should save $1,000 every month for 18 years so your kid can go to college, the difference between Ivy League and the 50th best school and whether AI might make all of this redundant. My guest today is Sean Johnson, a startup investor, business coach and professor who helps professionals build intentional businesses. Learn more about Sean: Connect...

Yes, I left a high-paying job. But I’ve never told the story about what motivated me, how I got promoted so quickly and how I deal with my money insecurities — as a kid and a grown-ass man. This is a very detailed (solo) episode that shares for the first time: - My Wall Street incomes - Current and past spending - Strategies I used to get promoted - Changes in my net worth - Childhood fears around...

What is self-love? The opposite is self-loathing. We discuss self-directed burnout, the need to be perceived as “good,” psychedelic journeys, managing your fight-or-flight and a DIY playbook for self-love. My guest today is Anita Amini, a software engineer and somatic coach based out of London. Learn more about Anita: Connect with Anita on ⁠Twitter⁠ Connect with Anita on ⁠LinkedIn⁠ Check out Anita...

Legacy is a tricky thing. We all want our lives to matter, but what does this actually mean? Kris, a writer, father and former options trader is joining me today to discuss quitting finance, career change “experiments,” a family Code of Arms, Die with Zero and why we maybe have the wrong idea of legacy altogether. Kris is a writer, father and former portfolio manager trading options. Learn more ab...

We are surrounded by status games. Whether it’s having a blue text bubble, a fancy car or the right combination of universities and ex-employers - we’re constantly signaling our worth. But is it even possible to escape these games? Or is the conscious decision against obvious status games just the same game in a different form? Jenny is a podcaster, best-selling author, keynote speaker and dog mom...

Imagine your own funeral. Your friends are asked to describe you. And they say: “You know what? He / she lived a really ordinary life”. The thought of it makes me shiver. But why? Join Carl and I as we explore why we should celebrate being ordinary, why not everything has to be heroic and what it actually means if you say “I want my life to matter”. Learn more about Carl: Connect with Carl on ⁠Twi...