Venkatesh Rao (Ep.27): The stress that makes you come alive

Venkatesh Rao defies labels – he’s a blogger, thinker, consultant whose ideas span the digital economy, science, philosophy, and the zeitgeist. Rao is the creator of Ribbonfarm and Breaking Smart and we discuss “paycheck addictions” and the wave of transformation that’s going to hit the economy. Is becoming a free-agent a way to stay ahead of the curve? How should a mid-career executive prepare? An immersion in the technology conversation is a must – but so is the ability to emotionally self-regulate.



Holly Rogers (Ep.26): The tiny compounding adjustments of mindfulness

Today’s episode should be called mindfulness for hyper-driven skeptics with no time. Holly Rogers is a psychiatrist at the student counseling center at Duke University and the co-founder of the center for Koru Mindfulness. Holly’s training as a psychiatrist provides a repertoire of research for the benefits of mindfulness, such as improving cardiovascular health, building a tolerance for discomfort, and my personal favorite: noticing tiny pain points with clarity and making adjustments that compound over time. We also discuss the “lowest effective dose” (10 minutes for 4 weeks), why today’s college students are way more anxious than in the past, and why mid-life crisis seem to be starting earlier.





Ted Seides (Ep.25): Money makes you more of what you already are

Let’s talk Hedge Funds! Ted Seides is a long time hedge fund investor and the host of the Capital Allocators Podcast. He’s a kindred spirit and we overlapped during the go-go days of the hedge fund industry. While this industry has some of the smartest and hardest working individuals, it’s also got some perverse incentives, outright greed, and is a breeding ground for the Three Es (Ego, Envy, Entitlement – all of which I experienced). The industry is undergoing tremendous change and we discuss sussing out internally motivated individuals, the keys to growing wealth, and how money makes you more… of what you already are.




Maya Benattar (Ep.24): Trauma with a “little t”

Maya Benattar is a psychotherapist and music therapist. She gives us a lay of the land of therapy and how it differs from life coaching. We talk cultural stigmas, different approaches such as CBT or psycho dynamics, and the difference between Trauma with a “big T” and a “little t.” Most of us have experienced (little t) trauma in the form of bullying, otherness, and insecurities such as body image. We explore the myth of being emotionally self-sufficient, Maya’s work in helping clients hold dual perspectives, picking podcasts over music, and navigating the emotional side of Tinder.



Andrew Taggart (Ep.23): Skimming the surface of life

Andrew Taggart is a practical philosopher who works with executives and entrepreneurs. He challenges them to investigate life’s basic assumptions, even if it’s uncomfortable. We discuss high performers’ antagonistic relationship with time and their desire to turn life into a series of problems which can be solved – and how this can mask our confounding relationship with mortality. Instead of avoiding these question, we consider how “an examined life, is a life lived more fully.”





Caroline Webb (Ep.22): Behavioral science and your best self

I often get listener pushback when we discuss happiness and introspection – this skepticism comes from the fact that the learnings aren’t grounded in data and they lack the pragmatism and relevance to our daily jobs. Today’s guest, Caroline Webb bridges that gap. She’s a former McKinsey partner, leadership coach, and economist and is used to C-Suiters pushing back on topics that are too “woo-woo.” She’s the founder of SevenShift, where she uses insights from behavioral science to help executives improve their working life. We discuss humans’ natural tendency to scan our environments for threats and how this impacts our brains. Are these threats real? How do we stop negative thought spirals? Is technology a source of threats? And a reader favorite, is fear a good motivator?



Auren Hoffman (Ep.21): Question your default options

Auren Hoffman is a serial entrepreneur and investor in over 75 tech companies. He’s the CEO and Chief Historian of SafeGraph and co-founder and former CEO of LiveRamp. This is a conversation about thinking, reasoning, and cultivating self-awareness. We discuss: default options (such as going to college or buying a house) and the need to reaffirm these on a regular basis; combatting status-seeking behavior; the challenging skill of holding two opposing views at once; how being “cool” or a social outcast impacts entrepreneurship; and why when it comes to work-life balance, Auren thinks we should recruit “proud members of the anti-balance society.”





Jocelyn K. Glei (Ep.20): Make haste slowly

Jocelyn K. Glei lives at intersection of the creative process, self management, and the future of work. She’s a creative polymath who’s held editorial positions, written a book on email, and just launched the podcast Hurry Slowly. Tactically, we chat about how people with corporate jobs can “flex their creative muscles” and why inbox zero is so damaging. Theoretically, we debate the subjective nature of time, how productivity requires a deeper conversation on achievement, and how the best things in life are imperfect and thus cannot be optimized.

Venetia Pristavec (Ep.19): How a single moment can change everything

Have you ever wondered how a single moment can change everything? Venetia Pristavec is an observer and storyteller. She happened to take a picture of a mattress on her floor and then rented it out to a stranger on the Internet. She then became convinced of the power of small human interactions and went on to join that small company, Airbnb, as their 7th employee. She rode that rocket ship for 5 years yet realized that while she was the voice of the company, she didn’t know her own voice. We have a really deep conversation, covering her thyroid cancer, turning into (as opposed to away from) others’ suffering, and why Venetia asks people pleasers about their “relationship with anger.”


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Kevin Delaney (Ep.18): Be bold and creative

We’ve all been in that meeting during which leadership says they’re ready for change. Yet deep inside, you know that it’s the classic Innovator’s Dilemma and you’ll be sitting in that same meeting for the next 10 years. In this episode, I interview Kevin Delaney, co-founder and editor in chief of Quartz about building a company in a time of flux for the media industry and challenging many of the established norms. We discuss how his leadership philosophy has evolved, what to do when your “staff is under siege” (from deep-pocketed competitors), the differences between Gen Z/Millennials/Gen X, and the practice of writing letters to our children that they’ll read at a much later date.