Best Sam Lessin Podcasts (2025)

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655: Morgan Housel - The Simple Formula For Happiness, Betting on Others, Gaining Independence & Purpose, Family Vacation Secrets, The Art of Spending Money, & The Death Bed Lesson Every Leader Needs to ... 57:19

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4d ago57:19

57:19

Go to www.LearningLeader.com for full show notes The Learning Leader Show with Ryan Hawk Morgan Housel is the New York Times Bestselling author of The Psychology of Money, Same As Ever, and The Art of Spending Money. His books have sold over 10million copies and have been translated into more than 60 languages. This is brought to you by Insight Glo…

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654: Jake Tapper - The Most Important Leadership Skill, Handling Criticism, Chasing Your Curiosity, Understanding Tradeoffs, Responding to Rejection, and Being So Good They Can't Ignore You 1:03:44

11d ago1:03:44

1:03:44

Go to www.LearningLeader.com for full show notes This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. www.InsightGlobal.com/LearningLeader The Learnin…

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653: Sukhinder Singh Cassidy - Becoming a CEO, Transforming a Company, Earning the Promotion, Knowing Your Non-Negotiables, & Hiring Excellent Leaders 57:43

18d ago57:43

57:43

Go to www.LearningLeader.com for full show notes This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. Sukhinder Singh Cassidy is the CEO of Xero. Xero…

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652: Arthur Brooks - The Power of Teaching, The Arrival Fallacy, The Mad Scientist Profile, Lifting Heavy Weights, & The Two Best Practices To Be Happy 56:32

25d ago56:32

56:32

Apply to be in my next Learning Leader Circle - https://learningleader.com/leadership-circles/ This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. ww…

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651: Shaka Senghor - From Prison to Purpose: Breaking Mental Barriers, Working with Mentors, and Leading Through Vulnerability (How To Be Free) 51:47

1M ago51:47

51:47

Go to www.LearningLeader.com for full show notes This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. www.InsightGlobal.com/LearningLeader Shaka Sengo…

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650: Michelle "Mace" Curran - Building a World-Class Team, Running an Excellent Debrief, Rebuilding Trust, Feedback Loops, & How To Turn Fear Into Your Superpower 1:05:18

1M ago1:05:18

1:05:18

Go to www.LearningLeader.com for full show notes This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. My guest: Michelle “Mace” Curran is a combat vet…

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649: Sam Lessin - Type 2 Fun, Voluntary Hardship, Joy as a Competitive Advantage, Long-Term Thinking, & Life Lessons From Dad (Lessin's Lessons) 56:09

2M ago56:09

56:09

Go to www.LearningLeader.com for full show notes This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. www.InsightGlobal.com/LearningLeader My guest: S…

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648: Ed Latimore - Going From Zero to One, Taking Ownership, Positive Body Language, Strategic Hardship, & Hard Earned Lessons From The Hurt Business 1:02:03

2M ago1:02:03

1:02:03

Go to www.LearningLeader.com for full show notes This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. www.InsightGlobal.com/LearningLeader My Guest: E…

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647: Tim Ferriss - Chasing Your Curiosity, Internal vs External Scoreboards, Effectiveness over Efficiency, Winning Even if You Fail, Fame's Hidden Costs, & The Mount Rushmore of Podcasting 1:21:52

2M ago1:21:52

1:21:52

Go to www.LearningLeader.com for full show notes This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. www.InsightGlobal.com/LearningLeader My Guest: T…

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646: Nick Maggiulli - Proven Strategies for Every Step of Your Financial Life (The Wealth Ladder) 48:45

2M ago48:45

48:45

Go to www.LearningLeader.com for full show notes This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. www.InsightGlobal.com/LearningLeader Guest: Nick…

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645: Ryan Petersen (Flexport CEO) - Front Line Obsession, Gemba Walks, Relentless Work-Ethic, CEO Mastermind Groups, & Valuing Simplicity 58:23

2M ago58:23

58:23

Go to www.LearningLeader.com for full show notes The Learning Leader Show with Ryan Hawk This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. www.Insi…

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644: Blaine Anderson - The #1 Dating Coach In The World Teaches You How To Genuinely Connect With People 54:15

3M ago54:15

54:15

Go to www.LearningLeader.com for full show notes The Learning Leader Show with Ryan Hawk This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. Go to ww…

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643: Anthony Scaramucci - Getting Fired by President Trump, Working With a Life Coach, Playing Quarterback, Building Confidence + Charisma, Telling The Truth, & Finding Your Superpower 55:24

3M ago55:24

55:24

Go to www.LearningLeader.com for all show notes This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. Go to www.InsightGlobal.com/LearningLeader Anthon…

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Robinhood Drops a Nuke, Republic Reinvents The Forward Contract, and Rocket Dollar Founder Henry Yoshida On Self-Directed Private Investing 47:32

3M ago47:32

47:32

In this episode of The Scott Show, Scott sits down with Henry Yoshida, founder of Rocket Dollar and now head of Retired.com, to talk about the massive wave of innovation coming to the $18 trillion retirement market.From launching Rocket Dollar to help everyday investors use their IRAs to invest in real estate, startups, and crypto — to now running …

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642: Jim Murphy - Inner Excellence, AJ Brown, Presence, Managing Fear, Daily Goals, & Understanding Our Greatest Needs 51:51

3M ago51:51

51:51

Go to www.LearningLeader.com for full show notes The Learning Leader Show with Ryan Hawk This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. Go to ww…

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The Business of Buying Businesses with Acquire.com CEO Andrew Gazdecki 34:18

3M ago34:18

34:18

In this episode of The Scott Show, Scott sits down with Acquire.com founder and CEO Andrew Gazdecki to explore the fast-growing world of micro acquisitions. From his early Twitter rise to landing the premium domain Acquire.com, Andrew shares how he built a breakout marketplace where anyone—from side hustlers to solopreneurs—can buy or sell profitab…

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641: Larry Connor - The Big 6 Leadership Attributes, Building a Values-Based Culture, Becoming a Billionaire, Working on Saturdays, Flying Into Space, Diving To The Mariana Trench, & Existing To Be The ... 1:04:56

3M ago1:04:56

1:04:56

The Learning Leader Show with Ryan Hawk Go to www.LearningLeader.com for full show notes This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. www.Insi…

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640: Tony Reno (Yale University Head Football Coach) - Writing a Team Creed, Leaving it Better Than You Found It, Going to Gettysburg, Leadership Retreats, & Winning Championships 55:10

4M ago55:10

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Go to www.LearningLeader.com for full show notes The Learning Leader Show with Ryan Hawk The Arena gives you direct access to some of the most respected coaching minds in the world. Led by HOFer Sherri Coale, Brook Cupps, Geron Stokes, and Eli Leiker. Leaders who have built winning programs, led at the highest levels, and shaped the next generati…

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Retail Private Markets Mini Series Plug and US Open Week with Venmo Joe Koziol 44:33

4M ago44:33

44:33

Scott’s back with golf betting consigliere Joe Koziol to preview the 2025 US Open at Oakmont, the hardest test in golf—and the most honest major to bet. The guys break down who can survive the brick-wall greens, brutal rough, and USGA sadism, then roll through their top plays, longshots, and the unofficial return of their flagship segment: Guy Stuf…

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639: Katie Gatti Tassin (Money with Katie) - Building A Media Business, The Morning Brew Acquisition, Knowing Your Retirement Number, & Living Up To High Expectations 55:37

4M ago55:37

55:37

The Learning Leader Show with Ryan Hawk Go to www.LearningLeader.com for full show notes This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. www.Insi…

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638: Kirk Herbstreit - The Most Prepared Broadcaster In The World, Responding To Adversity, Faith, Elk Pride, High School Sports, NIL Deals, Lee Corso, & The Emotional Moment When The Buckeyes Won The ... 1:16:15

4M ago1:16:15

1:16:15

Go to www.LearningLeader.com for full show notes This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. www.InsightGlobal.com/LearningLeader Kirk Herbst…

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637: Tom Ryan (Ohio State Wrestling Coach) - Chosen Suffering, Emotional Control, Responding to Tragedy, Success Pillars, and Learning from Dan Gable 1:15:54

4M ago1:15:54

1:15:54

The Learning Leader Show with Ryan Hawk Go to www.LearningLeader.com for full show notes This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. www.Insi…

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636: William Von Hippel - Why We Need Both Autonomy and Connection to Find Happiness (The Social Paradox) 1:00:48

5M ago1:00:48

1:00:48

Go to www.LearningLeader.com for full show notes This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. Go to www.InsightGlobal.com/LearningLeader Willi…

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635: Rich Gotham (President of The Boston Celtics) - How To Build a Championship Organization 56:59

5M ago56:59

56:59

Go to www.LearningLeader.com for full show notes This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. Go to www.InsightGlobal.com/LearningLeader Rich …

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PGA Championship Storylines, Value Picks and Errant Takes with 'Big Kit & Venmo Joe' 44:54

5M ago44:54

44:54

Scott's back with his golf wagering pal Joe Koziol to break down this week's PGA Championship and whether or not Quail Hollow is just "Rory McIlroy Country Club". The two discuss a few emerging storylines such as; will Jordan Spieth sneak into the elite Grand Slam club? Who has the tastiest odds coming into the weekend, and whether or not the PGA m…

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634: Tom Nolan (CEO of Kendra Scott) - 2% Moments, Setting Big Goals, Being Unbalanced, Moving Fast, Coaching High Performers, & Going Through Hard Things Together 57:03

5M ago57:03

57:03

The Learning Leader Show with Ryan Hawk Go to www.LearningLeader.com for full show notes. This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. Go to w…

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Why Jeff Bezos, Coatue Launched a New Billion Dollar Private Fund For Individual Investors 42:27

5M ago42:27

42:27

This week, something seismic happened in private markets. Jeff Bezos, Michael Dell, and Coatue’s Philippe Laffont announced a $1B tech fund that’s now accessible to individual investors — with minimums starting at just $50K.Let that sink in.The floodgates are opening. What used to require millions and insider access is now coming to retail. First H…

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633: General Stanley McChrystal - In Pursuit of Greatness, High Standards, The Ranger Effect, Self-Discipline, White-Water Rafting, Obsession, & Making Choices That Define Your Life (On Character) 1:02:43

5M ago1:02:43

1:02:43

The Learning Leader Show with Ryan Hawk Go to www.LearningLeader.com for full show notes This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. Go to ww…

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RIP Venture Factory and The State of VC 2025 with Sam Lessin 38:09

5M ago38:09

38:09

Scott sits down with venture capitalist, essayist, and Slow Ventures GP Sam Lessin for a candid, high-signal conversation about the state of venture capital—and why the old playbook is officially dead. Sam unpacks the ideas behind his viral VC25 manifesto, including why the startup conveyor belt model is broken, how today’s founders are flying blin…

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632: Nick Huber - The Attributes of Winners, Becoming Great at Sales, Changing Your Mind, & The Fundamental Truths of Life (Sweaty Startup) 1:01:20

5M ago1:01:20

1:01:20

The Learning Leader Show with Ryan Hawk Go to www.LearningLeader.com for full show notes This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. Go to ww…

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Surviving The Grift Economy with Pop Culture Journo John McDermott 48:56

5M ago48:56

48:56

Scott sits down with longtime friend, journalist, and cultural critic John McDermott for a no-holds-barred conversation on the rise of the grift economy. John and Scott re-trace the evolution of modern hustle culture to unpack the cult of tech founders, the blurred lines between personal branding and deception, and why irrational self-confidence is…

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631: Bert Bean & Sam Kaufman - Obsession, Grit, Growth-Mindset, Winning in a Tough Market, Hiring for Potential, Running Ultra-Marathons, and Caring For Your People 1:13:14

5M ago1:13:14

1:13:14

The Learning Leader Show with Ryan Hawk Go to www.LearningLeader.com for full show notes This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. www.Insi…

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Craig Kilborn's Gorgeous Life, All-Time Sandwich Rankings, and Scott's Masters Weekend Recap 42:30

6M ago42:30

42:30

In this episode, Scott sits down with legendary host and comedic trailblazer Craig Kilborn for a wide-ranging conversation on life after late night, creative independence, and what it really means to stay above the fray. From his iconic runs at ESPN, The Daily Show, and The Late Late Show, Craig reflects on the highs of fame, why he walked away, an…

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630: Marcus Sheridan - How To Build Trust, Drive Sales, and Earn Endless Customers 1:01:59

6M ago1:01:59

1:01:59

Go to www.LearningLeader.com for full show notes This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. www.InsightGlobal.com/LearningLeader Bio: As an …

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The Masters Edition featuring Scott's Friend "Venmo" Joe 48:25

6M ago48:25

48:25

A different tradition unlike any other... Gambling on golf. Welcome to Scott Show: Masters Week Edition. Scott is joined by local legend and friend Joe Koziol to dive deep into one of the year’s most beautiful, chaotic, and bank-breaking sports weekends, The Masters 🏌️‍♂️A few highlights: - Why the Masters is our Super Bowl- Intruiging bets, props,…

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Markets Tank, Stop Listening to Noise, “Private Equitification” of Venture and the New Media Universe with Eric Newcomer 47:05

6M ago47:05

47:05

In this episode, Scott sits down with journalist-turned-operator Eric Newcomer for a wide-ranging conversation about building in public, the evolution of venture capital, and what it’s really like to run a media business. Eric shares the backstory of launching Newcomer, from a solo Substack to a $2M+ revenue business with marquee events like Cerebr…

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629: Anne-Laure Le Cunff - How To Live Freely In a Goal Obsessed World (Tiny Experiments) 54:27

6M ago54:27

54:27

The Learning Leader Show with Ryan Hawk. Go to www.LearningLeader.com for full show notes. This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. Go to …

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Darren Marble on Going Public, Market Convergence, and the Retail Renaissance 41:00

6M ago41:00

41:00

In this episode, Scott sits down with Darren Marble — the creator of Going Public and founder of Issuance — for a wide-ranging conversation on the rise of retail investors, the evolution of equity crowdfunding, and why he believes the best days of this industry are still ahead.Darren shares the inside story of launching Going Public, a groundbreaki…

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628: Anthony Consigli - Digging Graves, Playing Football at Harvard, Learning From Failure, Taking Big Chances, & Growing a Business From $3 Million to $4 Billion 49:28

6M ago49:28

49:28

Go to www.LearningLeader.com for full show notes The Learning Leader Show with Ryan Hawk Episode #625: Anthony Consigli - Digging Graves, Playing Football at Harvard, Learning From Failure, Taking Big Chances, & Growing a Business From $3 Million to $4 Billion Anthony's great-grandfather came from Italy and he was a stone mason. He had 6 sons. He g…