Cover image of Rad Awakenings with Khe Hy

Rad Awakenings with Khe Hy

Khe Hy was one of the youngest Managing Directors at BlackRock before he took the plunge into deep, uncomfortable self-exploration. Bloomberg called him “The Wall Street Guru” and CNN “Oprah for Millennials” and he is the creator of the Rad Reads newsletter and Quartz’s First Entrepreneur in Residence. The Rad Awakenings podcast tells the stories of individuals who are stuck, undergoing transitions, or embarking on new adventures. These authentic and vulnerable conversations will teach us about power of emotional self-regulation, introspection, and growth mindsets. Find out more at http://radreads.co

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Dan Shipper (Ep. 3): The Scorecard is Learning

Dan is a Wunderkid entrepreneur who has been building web apps since he was a kid. He went to Penn as a Philosophy major and bootstrapped his startup Firefly which he sold the same month as his graduation. So what happens to your internal monologue when you sell your company at a time when most grads are starting their first jobs? There’s the common story that says “When X happens, my life will begin.” But you wouldn’t say “I’ll start exercising once I get promoted to Managing Director?” Dan vulnerably shares deeper insecurities of social rejection, the emotional drain of self talk, and how a relentless drive to improve can be destructive. We riff on writing (how it’s like compound interest and creates serendipity), the dangers of putting off working on yourself, not doing “half a push-up” (when it comes to experimentation), and the lumpy nature of progress. And together we have a good laugh comparing how Dan and I, both nerdy, skinny and insecure teenagers hatched up detailed plans for social acceptance. See the full show notes at bit.ly/radpod3


1 Jun 2017

Rank #1

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Lisa Shalett (Ep. 8): You are Where You’re Supposed to Be

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 narrative as you change roles; or simply, asking your boss “What’s keeping you up at night?” We then discuss post-retirement life, driven in part by family considerations. Yet retirement isn’t as worry free as we perceive it to be, especially when identity and career are so intertwined. One must navigate FOMO, the (perceived) loss of relevance, maintaining one’s “edge,” and yes — even for retired Goldman partners — the emotional irrationality of negative cash flow burn arising from entrepreneurship. And her advice to those currently in the grind, make sure you carve out the space to call “time out” — so that a minimum you can reflect on the trifecta of life, family, and career. Full Show Notes: http://bit.ly/radpod8 E-mail Newsletter: http://bit.ly/RadReads

1hr 21mins

28 Jul 2017

Rank #2

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Srini Rao (Ep.6): Turning your Liabilities into Assets

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 can grow a family of mini-surfers – but also knows that being alone is infinitely better than being with the wrong person. Srini’s had a remarkable professional journey, he’s the failed byproduct of the “traditional model of education and work” and graduated into two recessions, the dot-com bust (undergrad) and the global financial crisis (MBA). Now, as the founder and CEO of Unmistakeable Media, he’s conducted over 700 podcast interviews, organized massive events, and is a published author of Unmistakable: Why Only Is Better Than Best. This is a wide-ranging conversation covering why men struggle to be vulnerable, if “follow your passion” is good advice, how to quiet the comparing mind, and the ingredients to finding flow at work: autonomy, purpose, and mastery. Show notes: bit.ly/radpod6 Unmistakable Creative Podcast: https://unmistakablecreative.com/podcast Finish What You Start Course: https://unmistakablecreative.com/finish Srini’s Book: http://a.co/fH1t2TL

1hr 3mins

6 Jul 2017

Rank #3

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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? + SHOW NOTES: bit.ly/radpod22 + JOIN OUR COMMUNITY: bit.ly/RadReads

1hr 3mins

10 Nov 2017

Rank #4

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Scott Norton (Ep.48): Contentment is so damn elusive

Scott Norton is your prototypical millennial – a tinkerer with a creative and entrepreneurial streak . There’s a narrative that the financial crisis crushed economic mobility for an entire generation of Millennials – in fact, Scott’s first job was at Lehman Brothers in 2008. Yet for Scott, the crisis catalyzed a trip around Asia on a foldable bike spanning 23 countries and 100 cities. Upon his return he co-founded Sir Kensington’s, challenging the consumer goods “complex” of ketchup and mayonnaise. We explore mission-driven businesses – are they marketing hype or changing the world? Regardless, big business has taken to the idea; last year Unilever acquired them for a pretty penny. Scott’s got the belt notches: he’s a touch above 30 with a spectacular exit.  How does this change someone? For sure, it takes failure off the table. But contentment, being present with loved ones, a quiet mind, and yes – even freedom – don’t appear overnight and can remain viscerally elusive. + THIS WEEK’S SPONSOR: Does your life insurance policy match your life circumstances? Whether you’re newlyweds, new parents, or new entrepreneurs, Cambridge will work with you to protect what matters most: your family. As an independent broker, Cambridge always represents the client’s best interest, not the insurance companies’.  Contact Cambridge for a complimentary assessment on personal or life insurance planning. + SHOW NOTES: http://rad.family/scott-norton + SUPPORT THE PODCAST: http://patreon.com/radreads


17 May 2018

Rank #5

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Adam Schwartz (Ep. 44): Navigating fatherhood and entrepreneurship

Adam Schwartz is the co-founder and COO of TeePublic an e-commerce platform for independent creators. TeePublic is a high growth company with 50+ employees yet is completely self-funded. Is it a lifestyle business? We explore the negative connotation of the term and how it translates into constraints, profitability, and the “life” part of lifestyle. One thing’s for sure, irrespective of the name, entrepreneurs have very little mindspace for anything but their companies. And therein lies some of Adam’s anxiety around becoming a new father. How does one make room for a new person, when life and work are already all consuming? And consistent with the RadReads ethos, it comes down to the repeated topics of time scarcity, financial security, achievement and how this all ties into our sense of self worth. + SHOWNOTES: http://rad.family/adam-schwartz + LOOKING FOR A COACH? Whether you need to get unstuck or are committed to self-exploration but don’t know how to begin, the Rad Family has got you covered. We’ve handpicked a group of talented coaches over at http://rad.family/coaching.


19 Apr 2018

Rank #6

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Mark Pollard (Ep.14): Creativity is an act of rebellion

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 influenced how he thinks about masculinity and its toxic elements. Mark’s got a phrase: “We know men through their deeds and ideas” which launches us into the challenge of separating achievement and identity. And finally, Mark shares the Mighty Jungle playbook, conducting a master class in storytelling, ideation, and writing. And for those building a personal brand, heed his advice on cliched buzzwords such as joy and empowered. SHOW NOTES: bit.ly/radpod14 SUBSCRIBE: bit.ly/RadReads MORE ON MARK + Mighty Jungle Website + Mark’s Blog: Life. Then Strategy. + Social Media: Instagram / Twitter / LinkedIn

1hr 8mins

15 Sep 2017

Rank #7

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Mihir Desai (Ep.40): The problem with optionality

Mihir Desai is here to demystify and rehabilitate finance. He’s an economics professor at both Harvard Business and Law School and author of The Wisdom of Finance where he uses uses stories from the George Orwell to Kanye West to explain concepts such as options, leverage, and herd behavior, then extrapolating them into broader life lessons. For example blindly following society’s expectations is a form of the principal-agent problem. And how professionals love “collecting options,” but forget that for options to work, you need to take risks. We cover Wall Street’s culture of fear, his “a-hole theory of finance,” and the industry’s lack of diversity. We talk more broadly about higher education’s “crisis moment” and if credentialing is important in the face of technological innovation (such as cryptocurrencies and social), and why the “free-agent economy” is overhyped. + SHOW NOTES: http://bit.ly/MihirDesai + JOIN OUR NETWORKING WEBINAR: Networking doesn’t have to be transactional or slimy – it can absolutely be achieved with kindness and generosity. Learn now to identify new relationships, have impactful conversations, and create a system for following up. http://bit.ly/radnetworking + SUBSCRIBE TO RADREADS: http://radreads.email


22 Mar 2018

Rank #8

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Molly Crockett (Ep. 45): The neuroscience of social media outrage

What’s happening in our brains as we mindlessly scroll social media? Or worse, when we angrily retweet posts from our tribe. Molly Crockett is an assistant psychology professor at Yale University, where she integrates classic social psychology with neuroscience. She explains how our brain’s reward system works and how this ties to digital moral outrage. Does outrage serve an evolutionary purpose? What are the social costs and incentives to the outraged individual? And what about the opposite, humble bragging and virtue signaling? Molly also shares how she applies her insights to lead a more focused and productive life. + SHOWNOTES: http://rad.family/molly-crockett + LOOKING FOR A COACH? Whether you need to get unstuck or are committed to self-exploration but don’t know how to begin, the Rad Family has got you covered. We’ve handpicked a group of talented coaches over at http://rad.family/coaching.


26 Apr 2018

Rank #9

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Tiago Forte (Ep.17): First principles of workflow design (part 2/2)

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: bit.ly/radbrain + SHOW NOTES: bit.ly/radpod17


6 Oct 2017

Rank #10

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Scot and Jacq Tatelman (Ep. 11): Doing What You Love, With Who You Love

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 episode’s “happy tears”). But they’re honest about the challenges of co-founding and co-parenting: how pre-emptive couples therapy helped realign their roles, creating boundaries with their two energetic young kids, and how the heck you achieve work-life balance when Beyonce’s peeps are calling while Jacq’s in labor. (tl;dr You don’t!) FULL SHOW NOTES: bit.ly/radpod11 JOIN THE COMMUNITY: bit.ly/RadReads


18 Aug 2017

Rank #11

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Cara Thomas (Ep. 13): From breakdown to breakthrough

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 this episode we discuss the importance of experiencing both positive and negative emotions, how the body breaks down when the mind breaks down, and why entrepreneurship is not for the faint-hearted.Skillshare is this week’s sponsor: Join the online learning community with 16,000+ classes in business, design and more. Get one free month of unlimited access. http://skillshare.com/radShow Notes: bit.ly/radpod13Subscribe to RadReads: bit.ly/RadReads


8 Sep 2017

Rank #12

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Bart Lorang (Ep.16): The world’s gonna have its way with you

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. + SPONSOR: Join Skillshare the online learning community with 16,000+ classes in business, design and more. Get one free month of unlimited access. http://skillshare.com/rad + SHOW NOTES: bit.ly/radpod16 + SHOW SOME LUV: patreon.com/radreads


29 Sep 2017

Rank #13

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Giorgia Lupi (Ep. 47): Discovering ourselves through data

What can data tell us about our own humanity? Giorgia Lupi is an information designer, artist and author with a love for creatively representing all types of data. She’s the co-founder of the design firm Accurat and few years ago, embarked on a small creative project with a friend. Every week they tracked a feeling, behavior, or event and then hand drew a postcard visualizing the observations. These post cards are delightful and were aggregated in a book called Dear Data and last year were acquired into MoMA’s permanent collection. Yet, even with this milestone contentment felt so elusive. Dear Data revealed that tracking the “mundane details” of our lives has the unintended consequence of putting us more in touch with our thoughts; forcing us to hit “pause” on our frenetic lives. And at the end, Giorgia shares a simple way for all of us to set up a small data project on our own lives. + THIS WEEK’S SPONSOR: Does your life insurance policy match your life circumstances? Whether you’re newlyweds, new parents, or new entrepreneurs, Cambridge will work with you to protect what matters most: your family. As an independent broker, Cambridge always represents the client’s best interest, not the insurance companies’.  Contact Cambridge for a complimentary assessment on personal or life insurance planning. + SHOW NOTES: http://rad.family/giorgia-lupi + SUPPORT THE PODCAST: http://patreon.com/radreads


10 May 2018

Rank #14

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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. + SHOW NOTES: bit.ly/radpod18


13 Oct 2017

Rank #15

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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.” + SHOW NOTES: bit.ly/radpod19 + BUILDING A SECOND BRAIN: Is your digital information causing creative paralysis? Redesign your workflow from first principles with Tiago Forte’s Nov. 6 class at bit.ly/radbrain (affiliate link)


20 Oct 2017

Rank #16

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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.


27 Oct 2017

Rank #17

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Dan Sevigny (Ep. 41): Addiction is like a river eddy

Dan Sevigny was sensitive kid who had learning difficulties and trouble connecting with his peers. He coped by cutting himself and started using alcohol and pills as a teenager. Which kicked off a 10+ year cycle where drug use, aggression, and petty crime would get him kicked out of school and then sent to rehab. The cycle became more destructive, the aggression turned more violent, the rehab leading to juvie and jail. Dan describes the feedback loops of addiction and how depression made him feel like he was “on fire, with no skin and with everything in his body hurting.” Dan makes it extremely clear that there’s no silver bullet to recovery, but help came in the form of a mentor, learning about Search Engine Marketing while in rehab, and numerous therapists, particularly around DBT (Dialectical Behavior Therapy). And through all of this, Dan honors his family, his mom and sisters in particular and he surprised me by how often he brings up his own privilege. + SHOWNOTES: http://rad.family/dan-sevigny/ + LOOKING FOR A COACH? Whether you need to get unstuck or are committed to uncomfortable introspection but don’t know how to begin, the #radfam has got you covered. We’ve handpicked a group of talented coaches over at http://rad.family/coaching.

1hr 4mins

29 Mar 2018

Rank #18

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Lindsay Beck (Ep.39): A second act

Lindsay Beck was an outdoorsy 22 year old who had just run a marathon when she was diagnosed with tongue cancer. The typical procedure: removing your tongue and communicating via whiteboard for the rest of your life. But at 22? With a life ahead of her and dreams of finding love and starting a family? Furthermore, chemotherapy (not just for tongue cancer) had a 90% sterilization rate – a fact doctors withheld from their patients and then obviously insurance wouldn’t cover egg freezing. During her recovery, Lindsay started the non-profit Fertile Hope to fix both of these flaws. Her goal was for Fertile Hope to cease to exist in 10 years… and it took nine. For her second act, she co-founded NPX Advisors to change the way non-profits are funded, adding transparency and accountability while creating a new security, the Impact Security. Oh, and she and her husband have four young kids, and we discuss prioritization, saying no, and what “family first” means. LOOKING FOR A COACH? Need to get unstuck? Ready to take a risk? Or are you committed to self-inquiry but don’t know how to begin? Look no further than the #RadFam. We’ve curated a group of talented coaches over at bit.ly/radcoaching.

1hr 5mins

15 Mar 2018

Rank #19

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Tiffany Zhong (Ep. 42): Your unique perspective

The Wall Street Journal called Tiffany Zhong Venture Capital’s Teenage Analyst.  At 21, she’s worked at Product Hunt, sourced consumer investments, and is the founder of Zebra Intelligence, a consulting firm for brands trying to understand Gen Z. Her journey starts on Twitter where as a teenager she engaged prominent VCs and tech founders, asking them about their businesses and sharing her views on apps and products. Tiffany gives us both a networking and Twitter 101 as she shares the importance of (digital) emotional intelligence, leading with the question “how can I be helpful” and how, irrespective of your age, everyone has at least one thing they can bring to a conversation: Perspective. Tiffany dropped out of Berkeley after a year and we discuss different learning methods, the importance of college, and how she feels about the lack of a safety net in a degree. Tiffany discusses college students and teens – the “side hustle generation,” deft at building e-commerce companies and leveraging their social followings to make money. We also discuss the Gen Z stereotypes of attention, entitlement, and anxiety – and how Gen X’ers should not call Lil Pump, Little Pump. + SHOWNOTES: http://rad.family/tiffany-zhong/ + LOOKING FOR A COACH? Whether you need to get unstuck or are committed to self-exploration but don’t know how to begin, the Rad Family has got you covered. We’ve handpicked a group of talented coaches over at http://rad.family/coaching.


5 Apr 2018

Rank #20