Here's part II of my chat with Philip Simon. To recap, as a child Philip played hooky from school to read in the library, graduated high school and lived in a cave (as he pursued monkhood), and taught himself markets and finance by reading every single word of the FT and the Economist for four straight years. We pick up part II with Philip's corporate development role at a high frequency trading firm. We discuss “dual consciousness” or bringing two different versions of yourself to work and...

Philip Simon is the "Rad Genius." His life and career have bucked convention and traditional narratives, and are the consequence of a ravenous curiosity and thirst for knowledge. Philip's story starts in the library, where as a kid he would read multiple books a day (an estimated 1,500 by the time he graduated). After graduating, he dabbled in the Marines, moved to a cave in Greece to pursue a life of asceticism (i.e. severe self-discipline and abstention from all forms of indulgence) and...

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...

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...

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...

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...

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." + SHOW...

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...

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...

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...

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...

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...

Tiago Forte is our resident productivity guru and he interviews me in Part 2 of our workflow series. We nerd out on our productivity toolkits and blockages and I dive into my passion around human connection - and the systems I use to accelerate serendipity and build community.   + SPONSOR: Join Skillshare the online learning community with 17,000+ classes in business, design and more. Get one free month of unlimited access. http://skillshare.com/rad + SIGN UP FOR TIAGO'S CLASS:...

Tiago Forte is our resident productivity and workflow guru and the founder of Forte Labs. This is part 1 (of our 2 part series) in which we geek out on our First Principles (i.e. building blocks) of workflow, productivity, and personal knowledge management. Tiago approaches these questions through the lens of design thinking and also reflects on some of the blind spots in his system. + SPONSOR: Join Skillshare the online learning community with 17,000+ classes in business, design and more....

Bart Lorang is the founder and CEO of FullContact. FullContact is a high-growth, venture-backed company (having raised $50 mm) with 250 employees and multiple offices across the world. Bart and I discuss work-life balance and how Bart balances self-care, spending time with two young kids, while being a devoted father/husband. Bart drops amazing CEO wisdom on how empathy can be learned, thwarting your team’s fight or flight reflex and how culture is meaningless if it doesn’t terrify people. +...

Mark Pollard is a straight up OG: he created Australia’s first Hip Hop zine and designed web sites during the early days of Web 1.0. Mark is the founder of Mighty Jungle, where he helps founders make their brands make sense — through brand strategy and mental workouts. Mark's fiercely analytical and left-brained, but also “rebelliously creative” with a strong understanding of human biases. In this episode we reminisce about the 90s, chat about the chaos of his teenage years, which really...

Today's guest, Cara Thomas, dared me to buy a coffee for the person in line behind me. I was terrified of the awkwardness and possible rejection - yet once I did it, felt truly alive. Cara created Serenflipity to spark that feeling in each of us after a seven year career as an innovation consultant. The simple flip of a card throws you into wonder and serendipity, feelings that often vanish as we "grow up." Cara's journey into entrepreneurship has (literally) taken her around the world and in...

Richard Hughes-Jones did it. After 10 years as a management consultant, he took the plunge to start his own practice - fueled in part by his love for backcountry skiing. Then on a routine check up, his doctor states “That's not supposed to be there.” Stage 3 Colorectal cancer. It's the news we all dread - what happens next? Do you take the Anti-Fragile approach of “that which does not kill me only makes me stronger” or the Buddhist approach of "relinquishing control." How do you deal with...

Imagine building a business with a heart, with the person who shares your heart. Scot and Jacq Tatelman are the founders of State Bags, a mission-driven company building on the 1-for-1 model for school kids in need. Why backpacks? Because they "represent where you've been and where you're going." Their bags are *fire* and they've partnered with Chance the Rapper, Beyonce, Kevin Durant and the White House. The love, admiration, and pride they have for one another is truly energizing (note the...

Imagine getting a $3.6 million bonus at age 30? The dream scenario, right? This episode's guest, Sam Polk made more money in that a single bonus than his parents had earned over their entire lives. Yet he still needed to repeat the mantra "I am Enough" to reaffirm his own self-worth. Sam was a senior trader at King Street, one of the most successful hedge funds in the world. But behind his rocket-ship trajectory was a story of rage, addiction, arrests, and loneliness - the result of a...

Whether you’re an entrepreneur, college grad or retired Goldman partner, you’ve probably experienced some form money anxiety. For a tiny piece of paper, money possesses this incredible power to trigger intense feelings such as FOMO, envy, inadequacy and outright fear (aka the poverty mindset). And it never ceases to amaze me how rational people (and many finance professionals) turn a complete blind eye to this important area of their lives. Today’s guest, Ashley Feinstein Gerstley coaches...

This week’s episode is a story of career agility, embracing change, and living with intention. Lisa Shalett is a former Goldman Sachs partner, now board director and startup investor/advisor. At Goldman, Lisa held numerous leadership roles, including Japanese Equities, Global Compliance and Brand Marketing/Digital Strategy. She shares with us her approach to these transitions or “reinventions:” the danger of viewing your skills in narrow contexts (such as your current job); controlling your...

What is a life coach? What does life coaching consist of? Does it work? In this episode, we'll meet my coach, Kate Bednarski, one of the most impactful people in my life. I’ve asked Kate to throw out all patient confidentiality constraints and crack open all of her notes from our two years of working together. We start with our first meeting, where I showed up “jacked up on caffeine” a 34 year old guy rife with many tensions. I had a messed up relationship with time - there was never...

And by liabilities, we mean "Angelina Jolie lips." I'm not kidding, I never thought I'd open a podcast by asking another guy about his lips. And that's only one of many similarities I share with this week's guest, Srini Rao, the CEO of Unmistakable Media. Srini and I also had “non-existent” dating lives which led to a deep-rooted fear of never falling in love and spending life alone. Today, at 39 - a self-proclaimed "late bloomer" Srini is still searching for that special person with whom he...

Anastasia was destined to be an options trader since she was a little kid: she loved finishing at the top of the leader board during elementary school games and came up with her own brute-force approach multiplication tables. She then had her first shift, joining McKinsey and 18 months later found herself at a crossroads: Get her MBA or commit the money she would’ve spent and start building stuff. She chose the latter — “The business school of the world” as she calls it. Her thinking is...