Best Sean Weisbrot Podcasts (2025)

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Never Show Customers Your Underpants (A Guide to AI Pricing) 33:03

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17h ago33:03

33:03

Are you making the #1 mistake in AI pricing? Many founders are using their old SaaS pricing model, but for AI, that’s a huge error. As pricing expert Dan Balcauski explains, it’s like showing customers your “underpants”, and it’s killing your sales. In this guide to AI pricing, Dan breaks down why the game has changed. Unlike traditional SaaS, AI p…

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How I Get a 70% Reply Rate on LinkedIn DMs (CEO of an 8-Figure Agency) 32:25

5d ago32:25

32:25

How do you get a 70% reply rate on LinkedIn DMs? In this episode, I sit down with Gabe Lullo, CEO of the 8-figure sales development agency Alleyoop, who shares his exact method for filling his sales pipeline every single day. Gabe unpacks the hard truths about modern sales, explaining why most LinkedIn outreach is just noise and how hyper-personali…

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Why 80% of Leaders Are Dangerously Behind on AI 34:01

8d ago34:01

34:01

A shocking statistic reveals that 80% of leaders are dangerously behind on AI, and the window to catch up is closing fast. Most are trapped by day-to-day "urgent" tasks, ignoring the "important" work of AI adoption that will determine their company's future. In this episode, executive coach and founder of NewPo, Arielle Lechner, explains why so man…

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Is Your Work Ethic Secretly Sabotaging Your Business? 32:52

12d ago32:52

32:52

What if your "great" work ethic is secretly sabotaging your business? It's a tough question, but one every founder needs to confront. The toxic hustle culture sold by Silicon Valley isn't just unhealthy, it's often unprofitable. In this episode, Personal Growth Advisor Brad Farris joins me to dismantle the "grind" mindset. We explore why overworkin…

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Stop Building a Startup and Just Buy a Profitable Business 20:17

15d ago20:17

20:17

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How I Bought an $8M/Year Company With Only $5,000 34:04

19d ago34:04

34:04

Ever wonder how someone bought an $8M/year company with only $5,000? Gary Shelton did just that, and in this interview, he reveals his exact model. Gary is "The Coaching King," having acquired, scaled, and sold 12 different businesses over the last 50 years, each hitting 8-figures per year. He explains why mindset is the #1 reason most entrepreneur…

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The "Hero Leader" Delusion That's Secretly Destroying Your Team 34:10

22d ago34:10

34:10

Are you accidentally destroying your team with a "Hero Leader" mindset? Many leaders believe their job is to be the primary problem-solver, but this approach can secretly sabotage team performance and create a massive bottleneck. This is the "Hero Leader" Delusion. In this interview, executive coach Dr. Carla Fowler (MD, Ph.D.) breaks down the psyc…

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Poor People Add, Rich People Multiply, Billionaires Subtract 39:35

26d ago39:35

39:35

Why do billionaires subtract? It’s a powerful mindset that separates the ultra-successful from everyone else. In this dense masterclass on productivity, Todd Hagopian, who runs a $90 million business division, breaks down the wealth framework he learned from a billionaire: poor people add, rich people multiply, and billionaires subtract. He explain…

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The New B2B Buyer Doesn't Want to Talk to You 31:27

29d ago31:27

31:27

The New B2B Buyer Doesn't Want to Talk to You. Nearly 60% of B2B buyers are now millennials who grew up online and expect a seamless, self-service experience. In this interview, B2B expert David explains why personalization and a frictionless, multi-channel journey are the keys to winning over the modern buyer. Learn how to blend digital self-servi…

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Why AI Makes Your Website MORE Important, Not Less 28:23

1M ago28:23

28:23

Do you know Why AI Makes Your Website MORE Important, Not Less? While AI agents seem to be replacing everything, your website is the one place you control your message and the primary "repository of information" that large language models use to learn about your business. In this interview, domain broker Jeffrey Gabriel explains that without a well…

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A Bad Investor is Worse Than No Investor 31:22

1M ago31:22

31:22

Every founder needs to hear this: A Bad Investor is Worse Than No Investor. Before you start chasing venture capital, you must understand the risks. In this interview, M&A expert Scott Kelly explains why bootstrapped founders of seven, eight, and even nine-figure brands often love their lives, while many VC-backed founders are miserably stressed. W…

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This Sales Test Revealed My #1 Weakness 33:08

1M ago33:08

33:08

I took a sales ability test, and this sales test revealed my #1 weakness. The results showed that in a sales context, I have a tendency to believe that talking is more important than asking good questions. In this unique episode, sales expert Mike Irving, founder of Advanced Business Abilities, analyzes my live test results, breaking down my streng…

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Stop Solving Problems. Start CREATING Them. 32:38

2M ago32:38

32:38

What if the biggest obstacle to your company's growth isn't the problems you can't solve, but the ones you aren't creating? This counterintuitive idea is the key to radical business transformation. In this episode, Sean Weisbrot sits down with Ted Santos, President of Turnaround Investment Partners, to explore why leaders must stop solving problems…

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The #1 Mistake in AI-Generated Content (And How to Fix It) 28:30

2M ago28:30

28:30

Most AI-generated content is easy to spot, and journalists are hitting 'delete' the second they see it. So, what are the tell-tale signs, and how do you avoid them? I sat down with Curtis Sparrer, a PR expert and founder of Bospar, to find out. He reveals The #1 Mistake in AI-Generated Content (And How to Fix It): using AI as your final draft inste…

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"The Customer Is Always Right" is a Destructive Lie 30:57

2M ago30:57

30:57

We've all heard the phrase "The Customer Is Always Right," but what if following that advice is secretly burning out your team and killing your business? I sat down with Borja Cuan, CEO of Four15 Digital, who learned this lesson the hard way. He shares his powerful story of why he now believes "The Customer Is Always Right" is a Destructive Lie, an…

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An 8-Figure E-commerce Founder's AI Toolkit 29:43

2M ago29:43

29:43

What is the AI toolkit that top e-commerce founders are using to scale their brands? It's a mix of proprietary and public tools that automate everything from product research to marketing. I sat down with Neil Twa, CEO of Voltage Holdings, who has built multiple seven and eight-figure e-commerce brands. He shares his 8-Figure E-commerce Founder's A…

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Why Not Owning Bitcoin is Your Biggest Financial Risk 27:49

3M ago27:49

27:49

Everyone talks about the risks of owning Bitcoin, but what if the real danger is not owning it at all? I sat down with Frank Hepworth, founder of the crypto consultancy Yieldschool, who helps high-net-worth individuals navigate the digital asset space. He makes a powerful case for Why Not Owning Bitcoin is Your Biggest Financial Risk, arguing that …

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The Real Danger of AI: We're Losing Control of Ourselves 31:06

3M ago31:06

31:06

What is the real danger of AI? It's not that AI will become our overlords; it's that we will become so reliant on it that we lose control of ourselves. I sat down with William Welser IV, CEO of Lotic.ai, to discuss this critical issue. He argues that The Real Danger of AI: We're Losing Control of Ourselves comes from offloading our "cognitive respo…

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How to Build an AI Moat for Your Business (Without Consultants) 27:51

3M ago27:51

27:51

Every business owner is asking how to build an AI moat, but most are going about it the wrong way. I sat down with Alberto Rizzoli, CEO of V7 Labs, who argues that hiring expensive AI consultants is a "recipe for disaster". He shares his framework for How to Build an AI Moat for Your Business (Without Consultants) by starting with small, internal e…

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How I Trained an AI Agent to Do My Cold Outreach 31:18

3M ago31:18

31:18

Cold outreach is broken, but what if you could train an AI agent to replicate your most effective, human-sounding emails? I sat down with Jim Weldon, CEO of Prospect Desk, whose team is building a "digital twin org chart" where human sales reps manage teams of specialized AI agents. He breaks down his exact process for How I Trained an AI Agent to …

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How I Landed Fortune 500 Clients After Leaving My Corporate Job 31:08

3M ago31:08

31:08

Landing Fortune 500 clients seems impossible for a new business, but it's not. The secret isn't hustle; it's strategy, planning, and leveraging your unique story. I sat down with Alexandra Gonzalez, who left an 18-year corporate career at companies like Johnson & Johnson to build her own successful agency, Savvy Marketers. She reveals How I Landed …

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The Billion-Dollar Mistake Hiding in Every Shopify Checkout 52:33

3M ago52:33

52:33

There's a massive flaw in the Shopify checkout process that costs merchants millions in customer service hours and lost revenue. I sat down with Hamish McKay, CEO of Order Editing, a startup that's solving the one problem Shopify hasn't: letting customers edit their own orders after purchase. He breaks down The Billion-Dollar Mistake Hiding in Ever…

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The 5 Hidden Costs of Manufacturing Overseas That No One Talks About 29:57

3M ago29:57

29:57

Thinking about manufacturing overseas? It might not be as cheap as you think. There are hidden "soft costs" that can destroy your margins and your business. I sat down with Samuel Fish, founder of Shield Security Doors, who after a decade of challenges, made the bold decision to move his entire manufacturing operation from Eastern Europe back to th…

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The Hidden Assumptions That Are Sabotaging Your Leadership 29:26

3M ago29:26

29:26

Every day, unrecognized assumptions are sabotaging your leadership and preventing your team from making meaningful progress. Change is relational, not technical, and most leaders get it wrong. I sat down with Jeff Wetherhold, a master of Motivational Interviewing, to unpack this. He explains how to uncover The Hidden Assumptions That Are Sabotaging…

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The Future Factory: Where 1 Engineer Runs 1,000 Robots 30:52

4M ago30:52

30:52

Welcome to the Future Factory, a new model for manufacturing where software gives a single human unprecedented leverage. I sat down with Renan Devillieres, founder of the manufacturing venture studio OSS Ventures, to discuss this massive shift. He explains his vision for The Future Factory: Where 1 Engineer Runs 1,000 Robots, arguing that reshoring…

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Why I'm Investing in Plumbers, Not AI Startups 37:47

4M ago37:47

37:47

In a world obsessed with AI, my guest Travis Jamison is getting rich on boring businesses. His investment thesis is simple: bet on the things that AI can't change. He explains Why I'm Investing in Plumbers, Not AI Startups, and how blue-collar companies like HVAC and dry cleaners can offer better, more stable returns than venture capital. We also d…

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How 3D Visualization Prevents $100,000 Construction Mistakes 27:35

4M ago27:35

27:35

Using 3D visualization in architecture isn't a luxury; it's a necessity that can save you a fortune. Most developers don't realize a small upfront investment can prevent six-figure errors during construction. I sat down with Brian Corcodilos, CEO of the AI-enabled architecture firm DesignBlendz, to discuss this. He breaks down How 3D Visualization …

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Why The Highest Offer For Your Business is Often a Trap 29:22

4M ago29:22

29:22

When it comes to selling a business, most founders assume the highest offer is the best one. That assumption can be a multi-million dollar mistake. I sat down with Brandon Wolfe, Co-founder and partner at Jordan Partners, who sees this happen all the time. He shares a powerful cautionary tale that reveals Why The Highest Offer For Your Business is …

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Pay Yourself First: A Financial System That Prioritizes The Founder 25:52

4M ago25:52

25:52

The Pay Yourself First model is non-negotiable for sustainable entrepreneurship, yet most founders put themselves last. Financial strategist Monica Duggal breaks down her BITES method (Budget, Investing, Taxes, Exit Strategy, Systems) to help founders turn financial chaos into clarity. She explains why you need a financial system that prioritizes t…

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You're Giving Away Your Content for Free (And You Don't Know It) 29:34

4M ago29:34

29:34

This video is a crash course in content licensing and digital rights for the modern creator. Chances are, You're Giving Away Your Content for Free (And You Don't Know It). I sat down with Stewart Cohen, CEO of the media licensing platform SuperStock, to uncover the hidden traps in social media terms of service, the dangers of AI content scraping, a…

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Can Sponsorships Really Make You Millions? (Ryan Davis) 33:51

4M ago33:51

33:51

Worried about your influencer marketing ROI? You should be. Most brands make one critical mistake that tanks their campaigns before they even start. I sat down with Ryan Davis, co-founder of the creator agency People First, to uncover The #1 Mistake Killing Your Influencer Marketing ROI. The answer, backed by a Stanford University study, is a lack …

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AI is Already Learning Our Worst Traits (Bias, Deception, and Lies) 29:22

4M ago29:22

29:22

We like to think of AI as objective, but what if it's already picking up our most dangerous flaws? In this critical conversation, AI auditor Daniel Nikic and I explore how AI is Already Learning Our Worst Traits (Bias, Deception, and Lies). We discuss how biased data creates flawed models, my personal experience with an AI that "lied" about its wor…

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What I Learned in a 5-Day Dark Retreat About Limiting Beliefs 27:35

4M ago27:35

27:35

What happens during a 5-day dark retreat? My guest, Matthew Stafford, a Conversion Rate Optimization (CRO) expert, spent 121 hours in total darkness. He explains how the experience rewired his brain, teaching him that our limitations are just "consensual hallucinations." Matthew masterfully connects these deep psychological lessons to the world of …

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The One Sentence Our Lawyers Forgot That Almost Cost Me My Company 23:33

4M ago23:33

23:33

Imagine building a successful tech company, only to have your own uncle sue you, claiming he owns everything you built. My guest Derrick Girard, the Owner of DGirard Consulting and the Author of Put to the Test, reveals the one sentence our lawyers forgot that almost cost me my company, a tiny oversight that opened the door to a multi-million dolla…

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Does Microdosing Mushrooms Make You a Better Leader? 29:56

5M ago29:56

29:56

In a world of biohacking and performance optimization, a growing number of entrepreneurs are turning to an unconventional tool: psilocybin mushrooms. In this deep-dive conversation with Adam Schell, founder of the 7-figure supplement brand Brain Supreme, we ask: Does Microdosing Mushrooms Make You a Better Leader? Adam shares his complete microdosi…

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How We Built 50 AI Agents to Create a Virtual Law Firm 28:51

5M ago28:51

28:51

Arpan Nanavati is the Co-Founder & CEO of Cimphony, a Silicon Valley backed startup that recently raised over $5M USD, and the company has an AI that helps startups get access to smarter legal advice for less money. How do you build an AI that can handle the complexities of legal work without hallucinating? You don't build one AI; you build a team …

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How to Succeed in AI: The Secret is Being Less Lazy Than Everyone Else 29:47

5M ago29:47

29:47

Want to know how to succeed in AI when new tools are released every day? The answer is simpler than you think. My guest, serial entrepreneur and AI venture studio founder Sze Wong, shares his secret: you just have to be less lazy than everyone else. In this deep dive, Sze also tells the story of why he turned down a $50 million acquisition offer an…

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How I Built a 7-Figure Agency With a Team in the Philippines 29:18

5M ago29:18

29:18

Building a seven-figure, fully remote business is the dream for many entrepreneurs. My guest, Matthew Yahes, CEO of Extend Your Team, has actually done it. In this interview, he shares how I built a 7-figure agency with a team in the philippines, leveraging highly skilled, mid-career talent to scale his operations. Before finding this success, Matt…

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How a Rogue Trader Cost My Company $10 Million 39:05

5M ago39:05

39:05

David Miller is the Founder and CEO of Alchemy of Scale, a coaching practice that helps entrepreneurs systematize their operations and unlock true business growth. Imagine hiring a trader with a perfect resume, only to have them go rogue and lose millions of dollars in seconds. In this episode, David shares the full story of How a Rogue Trader Cost…

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A Lawyer's Honest Opinion on AI Replacing Him 28:58

5M ago28:58

28:58

What happens when a lawyer helps build an AI that could one day make his own job obsolete? I sat down with Ryaan Ibtisam, a practicing lawyer and the Co-Founder of Symphony AI, to get his candid take. He gives a lawyer's honest opinion on AI replacing him, discussing his initial fear of the technology and his prediction that law firms may hire 80% …

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This AI Conducts 100 Interviews So You Don't Have To 28:53

5M ago28:53

28:53

Tired of spending weeks sifting through candidates and conducting repetitive first-round interviews? My guest, Vol Goloshuk, CEO of AI Champ, is building the solution. We discuss his company, which has created an AI that conducts 100 interviews so you don't have to, providing a shortlist of the best candidates in minutes, not weeks. We also explore…

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I Asked AI to Find My "Hidden Negative Loops." The Truth Was Brutal 30:08

6M ago30:08

30:08

Joshua Hale is the owner of JH Media and Consulting, which leverages cutting-edge AI technology and strategic business insights to help entrepreneurs realize their full potential. Could an AI know you better than you know yourself? In this interview with AI consultant Joshua Hale, we explore the shocking personal and professional uses of artificial…

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You're Killing Your Business By Only Marketing to Existing Customers 25:53

6M ago25:53

25:53

Your obsession with high ROI might be secretly harming your company's long term growth. In this interview with Brook Shepard, CEO of Mason Interactive, we discuss the core reason why You're Killing Your Business By Only Focusing on Existing Customers. Brook explains how an over reliance on existing customers leads to a death spiral. He also reveals…

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Expand into the MENA Market with Salim Rennewi 27:45

6M ago27:45

27:45

Salim Rennewi is the Founder and CEO of SellAbroad, which helps brands expand into the MENA market (Middle East). You've Chosen the Hardest Business Model on Earth. In this interview, Sell Abroad co-founder Salim Rennewi validates the immense difficulty of e-commerce and explains that the natural progression for an operator often involves learning …

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Your Startup Will Fail Because You Don't Listen 23:58

6M ago23:58

23:58

Russell Brand is the Founder & Managing Director of Resonsible, which consults companies on their IT and general strategy, and he says your startup will fail because you don't listen. In this interview, startup advisor Russell Brand gives a brutally honest assessment of why most founders fail. He argues that as many as 19 out of 20 companies fail b…

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AI Can Write Code, But It Can't Do Architecture 34:57

6M ago34:57

34:57

Matt Strippelhoff is the Partner and CEO/CRO of Red Hawk Technologies, which develops game-changing custom software and platform integration solutions for private equity and mid-market clients. AI Can Write Code, But It Can't Do Architecture. In this interview, Matt gives his expert take on the current state of AI in software development. He explai…

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You Don't Know Why Your Customers Are Really Buying From You 26:09

6M ago26:09

26:09

You Don't Know Why Your Customers Are Really Buying From You. In this interview, RevHeat founder and CEO Ken Lundin argues that most founders, even those at $200 million companies, are clueless about why their customers truly buy from them . He explains that founders often think customers are buying features (like a report with four colors), but fo…

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Is Your Business Just a High-Paying Job You Can't Sell? 30:39

7M ago30:39

30:39

Is Your Business Just a High-Paying Job You Can't Sell? In this interview, M&A expert Cameron Bishop explains the critical difference between a valuable, transferable company and a "lifestyle business" that is almost solely dependent on the owner for its success and has no real exit value. Cameron also shares the craziest story he's ever seen in an…

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Stop Selling to the Masses, Sell to Rich People Instead 50:01

7M ago50:01

50:01

Stop Selling to the Masses, Sell to Rich People Instead. In this interview, Startups.com Chief Strategy Officer Ed Kang shares his #1 lesson for e-commerce success: stop trying to sell to the "mediocre middle" and instead focus on getting your product into the hands of "rich early adopters". He argues that wealthy people are the best evangelists, a…

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Your Pitch Deck Is Garbage if You Don't Have a "Why" 33:13

7M ago33:13

33:13

Saahil Mehta is the Co-Founder of Resnet World, which helps businesses increase profitability. Your Pitch Deck Is Garbage if You Don't Have a 'Why'. In this interview, angel investor Saahil Mehta shares the story of tearing apart a friend's pitch deck because it was all "what" and "how" but completely missed the founder's "why" . He explains that i…