Habits and Hustle

• Episode 501: Alejandra Maria Gallo: Dating Strategy, Emotional Regulation, and Taking Your Power Back

  You can be successful, confident, and unstoppable in business: and still lose your edge when it comes to love. In this episode of Habits & Hustle, I sit down with Alejandra Maria, a dating strategist and viral creator who helps ambitious women stop chasing and start leading with self-respect. We talk about what it really means to have emotional discipline, the ability to pause before reacting, to stay calm instead of proving your worth, and to walk away instead of negotiating for respect. Alejandra breaks down how “no contact” can be a power move, not a game, and why emotional diversification is the secret to staying grounded when everything feels personal. If you’re the kind of woman who thrives under pressure but keeps losing your balance in relationships, this one’s for you. We unpack how to bring the same clarity and control you have in business into your emotional life, without losing your softness or your power. Alejandra Maria has built a global audience of nearly a million women with her unapologetic, emotionally intelligent take on modern dating. Her insights have been featured in Newsweek, Girlboss, and more. And she’s redefining what it means to be “high value” in love and life. What We Discuss: (04:10) Why high-achieving women often lose power in love (06:05) The difference between emotional discipline and emotional suppression (08:42) “You can’t outwork emotional chaos”: bringing business mindset into dating (12:30) How “no contact” became the most powerful boundary you can set (18:20) Emotional diversification: spreading your energy beyond one relationship (25:14) Why confidence isn’t control, it’s composure (33:47) The signs you’re over-functioning in relationships (42:30) How to stop chasing and start being chosen (51:12) The mindset shift from proving your worth to holding your power (58:40) How to regulate emotions like you train your body: consistency over chaos       …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 Alejandra Maria: Instagram: @anxiouslyalej TikTok: @anxiouslyalej Youtube: @anxiouslyalej

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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 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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