Jeff Warren (Ep.36): You are what you repeatedly do

My happy place is interviewing a high energy meditator who curses like a sailor. Jeff Warren is a meditation teacher and the co-author of Meditation for Fidgety Skeptics (alongside Good Morning America’s Dan Harris). We talk a lot about mental health and Jeff’s longtime struggle with ADD, which to this day impacts his sense of acceptance and belonging. This conversation is nothing like what you’d expect from two meditators – it’s high energy, very personal, and pragmatic. We cover the daunting long game (i.e. lifetime) of meditation, how the stories around us can shape our reality (à la Sapiens), and how meditation is one of those small habits that unquestionably improves our happiness AND stops the endless and draining mental chatter.

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Abby Raphel (Ep.35): Stepping into your shadow

Abby Raphel is the founder of the Redwoods Initiative, an investment education company for wealthy families and the creator of the Blank Canvas Method for self-discovery. Abby grew up in a two stoplight town rural Florida, where she raised hogs and swam competitively, and was exposed to leadership at a young age when she joined the Future Farmers of America. She started modeling in college and moved to New York with two bags and two phone numbers. But as a “broke and B-rate model,” she went on to teach young girls about self-esteem then founded Redwoods, where she helps the uber-wealthy navigate their money. And yes, just because you have money, it does not guarantee fulfillment and meaning. We also discuss self-improvement and privilege, the role of hyper-agents in effectuating change, and confronting your shadow.

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Frank Ostaseski (Ep.34): Have a plan, hold it lightly

Here’s a controversial statement: contemplating your mortality will make you happier.  Frank Ostaseski is a pioneer in end of life care and holds this to be true. Frank co-founded the Zen Hospice Project, the Metta Institute, and is the author of The Five Invitations: Discovering What Death Can Teach Us About Living Fully.  Those who repress their fear of death, are missing what it can teach us. The anxieties we often discuss on this podcast, identity, acceptance, self-judgement, and loving unconditionally are all impacted by our views on death. And at the end of life, everything gets distilled into two simple questions: ‘Am I loved?’ and ‘Did I love well?’

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Lisa Daron Grossman (Ep.33): Curing loneliness through human connection

Lisa Daron Grossman landed in Swaziland as a 22 year old Peace Corps volunteer. The country had the world’s highest incidence of HIV and lowest life expectancy. Her team’s mission: mitigate the impact of the HIV epidemic. She was surrounded by loss and grieving – in her own words “It literally me open, like a sledgehammer to my chest.” Yet she was also surrounded by love, family, and community. She returned to the US with unprocessed trauma, depression and illness and living a dual life of odd jobs that eventually led her to the world of coaching. Today, she’s launching a cross-country project called the Connection Cure, trekking around the US looking to reinstill our lost sense of community and belonging.

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Anthony Demby (Ep.32): Busy is not a business model

Anthony Demby the founder of HumbleRIOT an audible idea shop that sits at the intersection of artists, culture, brands and experiences. Prior to founding HumbleRIOT, Anthony cut his teeth in the music industry with a range of roles in A&R, publicity and artist management. He has worked with artists such as Quadron, John Legend, and Childish Gambino. We discuss hitting financial rock bottom as an entrepreneur (i.e. an ATM balance of $0), expanding the conversation around race and police violence, the lack of diversity in the wellness industry, his eight year meditation practice, and Donald Glover’s “student of life mindset.”

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Lauren Imparato (Ep.31): From the trading desk to the yoga mat

There’s the cliché of leaving Wall Street to become a Yoga instructor. And then there’s actually doing it. As a young salesperson at Morgan Stanley, Lauren Imparato put her entrepreneurial prowess on display winning over both clients and bosses. Initially, Lauren immersed herself in yoga, nutrition, and meditation to help manage the daily grind – hiding it from her colleagues to avoid the “weirdo hippy girl” look. But the push to start her own business eventually overtook her and she went on to create RETOX, a wellness brand, Yoga studio, and best-selling book. We discuss mixing business and passion, using social media to build a brand, and the dangers of entrepreneurship as a form of escapism.

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Thomas Page McBee (Ep.30): Emotional detachment is a ticking time bomb

Thomas Page McBee is an author and journalist who writes about masculinity, and gender more broadly. Because Thomas is also trans, I entered the conversation with a preconceived set of beliefs, mostly based on the popular narratives I’d seen in media about trans people. Thomas and I discuss where his story and reporting diverged from those narratives, and he helped me understand that gender is complicated for all of us. Thomas has a unique and informed perspective on issues many men struggle with, including emotional detachment, gender policing, shame, and violence.

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Mike Lewis (Ep.29): The unsexy steps to chasing your dreams

At age 22, Mike Lewis had his dream job as a young venture capitalist at Bain Capital Ventures, moving up the ranks all while having fun and learning. But there was a little nagging voice reminding him of a dream – to play squash on the pro tour, even if it meant couch surfing and eating into his savings to do so. Mike did it, peaked at 112 and went on to write When to Jump: If the job you have isn’t the life you want. We’re bombarded by sexy stories about people who made the jump, but this obfuscates the planning, safety nets, and ways in which you can practice your own “jump.”

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Philip Simon (Ep.28, Part 2): To follow knowledge like a sinking star

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 if it’s a luxury to break out of that paradigm; the “duty of the strong to protect the weak” and how that interacts with the concepts of self-reliance and privilege; and alternatives to the broken model of growth capital/capitalism, such as mutualization, B-corps, or mission-driven companies.



Philip Simon (Ep.28, Part 1): From the cave to the trading desk

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 restored ancient fresco paintings. He taught himself financial markets by reading “every single word” of the Financial Times and Economist for four straight years, which led him into cold calling for stock brokers, an Internet startup (the Ladders) and the world of high frequency trading (GTS).