Habits and Hustle

• Episode 500: From Broke to Billionaire: Stephen Cloobeck’s $3.3B Mindset

  Stephen Cloobeck didn’t climb the ladder. He built his own. In this episode, we talk about what it really takes to grow a billion-dollar company without a business degree: and why integrity, discipline, and grit beat credentials every time. We get into his biggest pivots, how mentorship shaped his success, and why EQ always outperforms IQ in business and life. Stephen also opens up about giving away over $63 million, calling out “wokeness as weakness,” and what real leadership looks like when you’re under pressure. Stephen Cloobeck is the founder and former CEO of Diamond Resorts, which sold for $3.3 billion enterprise value. He’s been on Undercover Boss more than anyone, donated millions, and still believes character is the ultimate ROI. What We Discuss:  02:03 - Stephen's $63 million in philanthropic giving 04:02 - Undercover Boss episodes and giving away the most money  09:30 - Learning business from Mike Milken instead of business school  12:45 - Harvard Business School case study on his industry disruption  15:20 - Treating employees like family as competitive advantage  Thank you to our sponsors: Therasage: Head over to therasage.com and use code Be Bold for 15% off  Air Doctor: Go to airdoctorpro.com and use promo code HUSTLE for up to $300 off and a 3-year warranty on air purifiers. Magic Mind: Head over to www.magicmind.com/jen and use code Jen at checkout. Momentous: Shop this link and use code Jen for 20% off  Manna Vitality: Visit mannavitality.com and use code JENNIFER20 for 20% off your order  Prolon: Get 30% off sitewide plus a $40 bonus gift when you subscribe to their 5-Day Program! Just visit https://prolonlife.com/JENNIFERCOHEN and use code JENNIFERCOHEN to claim your discount and your bonus gift. Amp fits is the perfect balance of tech and training, designed for people who do it all and still want to feel strong doing it. Check it out at joinamp.com/jen    Find more from Jen:  Website: https://www.jennifercohen.com/ Instagram: @therealjencohen   Books: https://www.jennifercohen.com/books Speaking: https://www.jennifercohen.com/speaking-engagement Find more from Stephen Cloobeck:  Instagram: @stephenjcloobeck  Website: https://stephenjcloobeck.com/

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• Episode 500: From Broke to Billionaire: Stephen Cloobeck’s $3.3B Mindset

  Stephen Cloobeck didn’t climb the ladder. He built his own. In this episode, we talk about what it really takes to grow a billion-dollar company without a business degree: and why integrity, discipline, and grit beat credentials every time. We get into his biggest pivots, how mentorship shaped his success, and why EQ always outperforms IQ in business and life. Stephen also opens up about giving away over $63 million, calling out “wokeness as weakness,” and what real leadership looks like when you’re under pressure. Stephen Cloobeck is the founder and former CEO of Diamond Resorts, which sold for $3.3 billion enterprise value. He’s been on Undercover Boss more than anyone, donated millions, and still believes character is the ultimate ROI. What We Discuss:  02:03 - Stephen's $63 million in philanthropic giving 04:02 - Undercover Boss episodes and giving away the most money  09:30 - Learning business from Mike Milken instead of business school  12:45 - Harvard Business School case study on his industry disruption  15:20 - Treating employees like family as competitive advantage  Thank you to our sponsors: Therasage: Head over to therasage.com and use code Be Bold for 15% off  Air Doctor: Go to airdoctorpro.com and use promo code HUSTLE for up to $300 off and a 3-year warranty on air purifiers. Magic Mind: Head over to www.magicmind.com/jen and use code Jen at checkout. Momentous: Shop this link and use code Jen for 20% off  Manna Vitality: Visit mannavitality.com and use code JENNIFER20 for 20% off your order  Prolon: Get 30% off sitewide plus a $40 bonus gift when you subscribe to their 5-Day Program! Just visit https://prolonlife.com/JENNIFERCOHEN and use code JENNIFERCOHEN to claim your discount and your bonus gift. Amp fits is the perfect balance of tech and training, designed for people who do it all and still want to feel strong doing it. Check it out at joinamp.com/jen    Find more from Jen:  Website: https://www.jennifercohen.com/ Instagram: @therealjencohen   Books: https://www.jennifercohen.com/books Speaking: https://www.jennifercohen.com/speaking-engagement Find more from Stephen Cloobeck:  Instagram: @stephenjcloobeck  Website: https://stephenjcloobeck.com/

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• Episode 499: Kim Perell: Building a $235M Company from the Kitchen Table + Why Perfectionism Kills Success

  What if perfectionism is actually killing your success? In this Habits and Hustle episode, Kim Perell, a nine-time serial entrepreneur, joins me to share why waiting to feel ready is the biggest mistake aspiring business owners make.  We dive into Kim's morning routine, her partnership with Jay Shetty on Junie, and why exercise is her number one productivity tool. We also discuss why iteration beats innovation, and how she balances building multiple companies while raising four kids. Kim Perell is a 9X founder, 2X bestselling author, and investor in 100+ companies. Kim is a dynamic TV personality on Entrepreneur Magazine's Elevator Pitch and regularly appears on Good Morning America, The Today Show, CNBC, Fox, and in Forbes, Inc., and The New York Times. Her book "Mistakes That Made Me A Millionaire" shares the unfiltered truth about the journey to success, proving that every mistake holds the potential for million-dollar lessons. What We Discuss: 04:20 - The number one mistake: waiting to feel 100% ready before starting 05:09 - The Marine Corps 70% solution and how to apply it 06:56 - Why iteration beats innovation (and saves time) 07:21 - Co-founding Junie with Jay Shetty in a crowded beverage market 58:10 - Daily routine: waking at 6 AM, red light therapy, and meditation 59:28 - Running a household with four kids like a company 01:00:29 - Workout routine: HIIT, Peloton, and personal training at home 01:01:08 - Supplement stack: Momentous protein and creatine 01:03:00 - Why exercise is about mental health and focus, not competition 01:03:27 - Exercise as the number one longevity hack above all supplements …and more! Thank you to our sponsors: Therasage: Head over to therasage.com and use code Be Bold for 15% off  Air Doctor: Go to airdoctorpro.com and use promo code HUSTLE for up to $300 off and a 3-year warranty on air purifiers. Magic Mind: Head over to www.magicmind.com/jen and use code Jen at checkout. Momentous: Shop this link and use code Jen for 20% off  Manna Vitality: Visit mannavitality.com and use code JENNIFER20 for 20% off your order  Prolon: Get 30% off sitewide plus a $40 bonus gift when you subscribe to their 5-Day Program! Just visit https://prolonlife.com/JENNIFERCOHEN and use code JENNIFERCOHEN to claim your discount and your bonus gift. Amp fits is the perfect balance of tech and training, designed for people who do it all and still want to feel strong doing it. Check it out at joinamp.com/jen    Find more from Jen:  Website: https://www.jennifercohen.com/ Instagram: @therealjencohen   Books: https://www.jennifercohen.com/books Speaking: https://www.jennifercohen.com/speaking-engagement Find more from Kim Perell:  Instagram: @kimperell Website: https://kimperell.com/

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• Episode 498: Sahil Bloom: How Physical Wealth Unlocks Mental, Financial and Relationship Success

  Listen to the full episode:  https://www.youtube.com/watch?v=yoiyKzb-rp4  Why does waking up at 5AM and working out transform losers into winners? In this Fitness Friday episode on the Habits and Hustle podcast, Sahil Bloom joins me to share how a simple 30-day fitness challenge saved a young man's life and why exercise is the "gateway drug" to success in every area of life. We dive into the science behind walking's 60% boost to creative output and why confidence comes from doing hard things repeatedly. Plus, we share the anti-to-do list hack, the energy calendar method, and why "grazing on low-quality tasks" is killing your productivity.  Sahil Bloom is an author, investor and former college baseball player at Stanford dedicated to helping others live more fulfilling lives. He is the author of "The Five Types of Wealth," a framework that goes beyond money to prioritize physical health, relationships, mental wellbeing, and purpose.  What we discuss: The inspiring story of a suicidal man who found power through 30 days of gym attendance Walking increases creative output by 60% and improves relationship connection How exercise breeds confidence  The anti-to-do list: what NOT to do each day for transformation Energy calendar method: color-coding tasks to optimize your life The loneliness tax of personal transformation and why it's worth paying Thank you to our sponsor: Therasage: Head over to therasage.com and use code Be Bold for 15% off  Air Doctor: Go to airdoctorpro.com and use promo code HUSTLE for up to $300 off and a 3-year warranty on air purifiers. Magic Mind: Head over to www.magicmind.com/jen and use code Jen at checkout. Momentous: Shop this link and use code Jen for 20% off  Manna Vitality: Visit mannavitality.com and use code JENNIFER20 for 20% off your order  Prolon: Get 30% off sitewide plus a $40 bonus gift when you subscribe to their 5-Day Program! Just visit https://prolonlife.com/JENNIFERCOHEN and use code JENNIFERCOHEN to claim your discount and your bonus gift. Find more from Sahil Bloom: Instagram: @sahilbloom Book: The 5 Types of Wealth Find more from Jen: Website: https://www.jennifercohen.com/ Instagram: @therealjencohen   Books: https://www.jennifercohen.com/books Speaking: https://www.jennifercohen.com/speaking-engagements

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• Episode 497: Nick Thompson: How Running 100 Miles Taught Him to Run a $13 Billion Media Empire

  How does a CEO who runs 100-mile races turn around a struggling media company? In this episode on the Habits and Hustle podcast, Nick Thompson, CEO of the Atlantic, joins me to share how the mental strategies that get you through mile 40 of a mountain race are the same ones that grow a publication from 800,000 to 1.35 million subscribers. We dive into why daily practice beats talent in both running and business, and the dark side of elite running culture that creates eating disorders. We also discuss the Signal chat scandal that drove tens of thousands of new subscriptions. Nick Thompson is the CEO of the Atlantic, which has grown profitable under his leadership after years of losses. He's also the American record holder in the 50K for runners 45+ and author of The Running Ground, a memoir exploring how running shapes life, business, and relationships. What We Discuss:  03:14 - Why Nick started running at age 5 with his father during a family crisis 08:46 - How running is a microcosm for life and teaches grit through hard things 14:24 - The Alexander Technique: How a guitar wrist injury prevented 25 years of running injuries 28:16 - Why consistent daily practice is the most important lesson from running 50:04 - How Nick got faster in his 40s by training smarter with specific workouts 55:40 - How the Atlantic grew from 800K to 1.35M subscribers through paywall optimization 1:01:10 - The Signal chat scandal: How Jeff Goldberg was accidentally added to the White House group chat 1:12:10 - Trump's "fixed heartbeats" theory and whether ultra running shortens your lifespan 1:17:25 - The dark side of running: Why elite coaches tell athletes to look like "a skeleton with a condom on" 1:19:19 - How running culture creates eating disorders and destroys young athletes' bodies …and more! Thank you to our sponsors: Therasage: Head over to therasage.com and use code Be Bold for 15% off  Air Doctor: Go to airdoctorpro.com and use promo code HUSTLE for up to $300 off and a 3-year warranty on air purifiers. Magic Mind: Head over to www.magicmind.com/jen and use code Jen at checkout. Momentous: Shop this link and use code Jen for 20% off  Manna Vitality: Visit mannavitality.com and use code JENNIFER20 for 20% off your order  Prolon: Get 30% off sitewide plus a $40 bonus gift when you subscribe to their 5-Day Program! Just visit https://prolonlife.com/JENNIFERCOHEN and use code JENNIFERCOHEN to claim your discount and your bonus gift.   Find more from Jen:  Website: https://www.jennifercohen.com/ Instagram: @therealjencohen   Books: https://www.jennifercohen.com/books Speaking: https://www.jennifercohen.com/speaking-engagement Find more from Nick Thompson:  Instagram:@nxthompson Website: https://www.nickthompson.com/

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