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/ 

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/ 

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/ 

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

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/

Listen to the full episode: https://youtu.be/trGbcAqF2dA?si=qG5E_F-gP4x8qQhp 

Why do you wake up at 3:30 AM and can't fall back asleep? In this Fitness Friday episode on the Habits and Hustle podcast, Michael Breus, the Sleep Doctor, says it’s not your fault. 

We unpack the science of why everyone wakes up between 1-3 AM, the shocking Alzheimer's connection to Benadryl, and why CBN (not CBD) is the cannabis compound that actually helps sleep. Plus: the truth about melatonin, why magnesium beats most sleep aids, and the supplement deficiencies sabotaging your rest.

Dr. Michael Breus is a clinical psychologist and one of only 168 psychologists in the world board-certified in sleep medicine. Known as "The Sleep Doctor," he's the author of five books including Sleep, Drink, Breathe and has treated celebrities from Carson Daly to Paris Hilton to DJ Steve Aoki.

What we discuss:

Why every human wakes up between 1-3 AM

The 4-7-8 breathing technique Navy SEALs use to lower heart rate below 60

Yoga nidra gives you 20 minutes of sleep benefit for every hour of rest

Regular Benadryl/ZzzQuil use directly linked to Alzheimer's disease

CBD does nothing for sleep. What actually reduces nighttime awakenings

The three deficiencies destroying your sleep

Why melatonin affects birth control, SSRIs, and is NOT for children

Natural alternatives to melatonin

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 Dr. Michael Breus:

Website:https://sleepdoctor.com/ 

Books: https://sleepdoctor.com/books 

Find more from Jen:

Website: https://www.jennifercohen.com/

Instagram: @therealjencohen  

Books: https://www.jennifercohen.com/books

Speaking: https://www.jennifercohen.com/speaking-engagements

What really happened behind Amazon's $13.7 billion acquisition of Whole Foods? In this episode on the Habits and Hustle podcast, John Mackey, founder and former CEO of Whole Foods, reveals why he walked away from the company he built over 44 years.

We dive into how Whole Foods went from a single vegetarian store to a 540-store empire that revolutionized American eating habits. We also discuss why only 0.5% of Americans are vegan despite the plant-based movement, why protein obsession is misguided, and how Erewhon is disrupting the company he created.

John Mackey founded Whole Foods Market in 1980 and served as CEO until 2022, growing it from a single store in Austin to a Fortune 250 company. He's the author of "Conscious Capitalism" and "The Whole Story," and now leads Love.Life, a revolutionary wellness center combining health, fitness, and medical care under one roof.

What We Discuss: 

03:27 - Why Erewhon has become "the new Whole Foods" and John's strategy to compete

07:46 - How John built Whole Foods with zero business education

14:50 - From pickles on hamburgers to vegetarian: John's food awakening at age 22

21:21 - The 100-year flood that almost destroyed Whole Foods after 9 months

26:50 - The hostile takeover attempt

29:17 - Meeting Jeff Bezos: The six-week whirlwind romance with Amazon

51:56 - Why John only took $1 salary for his last 16 years (and never got paid)

59:26 - Conscious Capitalism: The four pillars of building a purpose-driven business

01:09:00 - Love.Life: The one-stop wellness center that's "Whole Foods for health"

01:21:14 - Why only 0.5% of Americans are vegan and vegan restaurants are failing

01:24:42 - The protein myth: Why Americans eat too much protein and not enough fiber

…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 John Mackey: 

Instagram:@iamjohnmackey

Website:  https://johnpmackey.com/ 

Listen to the full episode:  https://youtu.be/NrHBimydPBU?si=mI2cLamva379hWMy 

Why do 70% of personal trainers sleep with their clients, and how does this statistic explain why most fitness professionals never build real wealth? In this Fitness Friday episode on the Habits and Hustle podcast, Adam Schafer from Mind Pump drops truth bombs about what separates successful trainers from those who plateau at $40K a year.

We unpack the psychology of professional boundaries, why "motivation is bullshit but self-belief is everything," and how the same insecurities that lead to sleeping with clients also trap people in toxic relationship patterns. 

Adam Schafer is the business strategist behind Mind Pump Media, a fitness podcast generating over $10 million annually. With eight national certifications, a pro-card in bodybuilding, and experience managing some of the largest fitness clubs in the Bay Area, his greatest achievement remains creating a media empire that disrupted the entire fitness industry.

What we discuss:

Why trainers sleeping with clients is second only to hospitals for workplace affairs

How breaking professional boundaries costs you the highest-paying, long-term clients

Why your peers lose respect and won't work for someone who crosses these lines

"Motivation is bullshit, self-belief is everything" - the mindset shift that creates success

Breaking addiction to "broken people" - how ego-feeding relationships mirror bad business choices

The confidence factor: Why self-belief matters more than looks, talent, or connections

Why successful people keep dating the wrong people despite self-awareness

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 Adam: 

Instagram: @mindpumpadam 

Podcast: https://mindpumppodcast.com/

Find more from Jen:

Website: https://www.jennifercohen.com/

Instagram: @therealjencohen  

Books: https://www.jennifercohen.com/books

Speaking: https://www.jennifercohen.com/speaking-engagements

What happens when biohacking's biggest evangelist spends $40,000 replacing his blood with young plasma? In this episode of Habits and Hustle, I sit down with Ben Greenfield, the ultimate biohacker and author of "Boundless," for a deep dive into the science of optimization. 

We discuss the real science behind fat loss, his daily skincare routine that keeps him looking decades younger, and why he believes faith is just as important as physical optimization. We also dive into his controversial take on GLP-1 microdosing, why the 12-3-30 treadmill trend is overrated, and how he went from extreme experimenter to finding balance between optimization and spirituality.

Ben Greenfield is a biohacker, human performance consultant, and New York Times bestselling author. He's one of the world's leading experts on performance, recovery, sleep, digestion, brain optimization, and anti-aging. His revised book "Boundless" is considered the encyclopedia of health optimization.

What We Discuss: 

(04:00) Why most people need digestive enzymes after 40 and how they unlock nutrients

(18:00) Cold plunging for women: What the research actually shows 

(36:00) The 12-3-30 treadmill trend: Why it's overrated for body composition 

(51:00) GLP-1 agonists: Why microdosing might be the future of appetite control 

(1:05:00) The plasma replacement therapy that cost $40K but made him feel "unstoppable"

(1:27:00) Faith, forgiveness, and finding purpose beyond biohacking 

(1:37:00) His anti-aging skincare routine that keeps him looking decades younger 

…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 Ben Greenfield: 

Instagram: https://www.instagram.com/bengreenfieldfitness/ 

Website:  https://boundlessbook.com/ 

Listen to the full episode: https://youtu.be/6jLhl8Zaznw?si=jaBuMbIWQApYpeEv 

Why does starting your day with protein reduce anxiety for the rest of the day? In this Fitness Friday episode on the Habits and Hustle podcast, Sal Di Stefano joins me to break down the science of blood sugar control, why intermittent fasting is "a terrible way to lose weight," and the shocking truth about cardio versus strength training for fat loss.

We also unpack the biggest mistake women make when tracking progress: obsessing over the scale instead of body composition. Sal explains why 40% of weight lost through cardio comes from muscle, shares a study where strength training alone beat cardio AND strength training combined for fat loss, and reveals why psychologists now prescribe high-protein breakfasts to anxious patients.

Sal Di Stefano is a fitness expert with over 20 years of personal training experience and co-host of the Mind Pump podcast, one of the top-rated fitness shows in the world.

What we discuss:

How protein at breakfast controls blood sugar and reduces anxiety throughout the day

The two-question filter for any fitness advice: "Will I do it?" and "Is it realistic?"

Intermittent fasting's original purpose and why it fails for weight loss

Cortisol addiction and the binge-restrict cycle fasting creates

When cold plunges hurt more than help for overstressed people

Cardio vs strength training: why 40% of cardio weight loss comes from muscle

The study where strength training alone beat cardio for fat loss

Ditching the scale: better metrics for tracking body transformation

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 Sal: 

Instagram: @mindpumpdistefano  

Podcast: https://mindpumppodcast.com/

X: https://x.com/mindpumpsal 

Find more from Jen:

Website: https://www.jennifercohen.com/

Instagram: @therealjencohen  

Books: https://www.jennifercohen.com/books

Speaking: https://www.jennifercohen.com/speaking-engagements