Best Overcomingfear Podcasts (2025)

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Perfectionism vs. Perfection: Essential Lessons for Entrepreneurs 9:20

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23h ago9:20

9:20

Did you like the episode? Send me a text and let me know!! Host: Jesse (with AI co-host Pi) Episode Length: ~7 minutes Episode Summary In this insightful episode of Business Conversations with Pi, Skoob and his AI co-host Pi dive deep into the crucial distinction between perfection and perfectionism—a topic every entrepreneur and business builder f…

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Imperfect Action: Albert's Entrepreneurial Success Story 48:43

8d ago48:43

48:43

Did you like the episode? Send me a text and let me know!! 🎙️ The Undiscovered Entrepreneur Podcast: Episode with Dr. Albert de Montes This week, host Jesse sits down with Albert deMontes, a New York-based talent agent, entrepreneur, and author of "Rise Above the Script: Confronting Self-Doubt, Mastering Self-Sabotage for Boring Artists." Albert sh…

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Entrepreneurship 101: Mindset, Opportunity Costs, and Deciding When to Leave Your Day Job 11:19

15d ago11:19

11:19

Did you like the episode? Send me a text and let me know!! 🎙️ Business Conversations with Pi: Entrepreneurship Mindset & Opportunity Costs Welcome to another episode of Business Conversations with Pi, where we decode the entrepreneurial journey with actionable advice and AI-powered insights! In this episode, host Jesse and AI co-host Pi dive deep i…

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Mastering the 3 C's: Create, Connect, and Contribute for Entrepreneurial Growth 40:28

23d ago40:28

40:28

Did you like the episode? Send me a text and let me know!! From Penny Candy to $100K Months: The Relationship Formula for Entrepreneurial Success Discover how entrepreneur SyS transformed from a suspended fourth-grader selling candy to generating consistent $100K months for 38 consecutive months. In this powerful episode, learn the relationship-bas…

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Virtual Teams for Startups: A Guide to Building Your Remote Workforce 11:20

29d ago11:20

11:20

Did you like the episode? Send me a text and let me know!! Podcast Episode: Building Virtual Teams for Startups Welcome to another episode of Business Conversations With PI, where we answer the most pressing questions for new entrepreneurs and startup founders. In this episode, we dive deep into the world of virtual teams, remote work, and actionab…

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A Quick Update: Build Your Business Podcast Will Return This Fall 2:52

1M ago2:52

2:52

This is a quick update from Matt on the Build Your Business Podcast. It’s been a crazy but good year with lots happening—family moves, business growth, and plenty of irons in the fire. Because of that, we’re taking a short break until the fall. 👉 Here’s what you need to know: We’ll be back this fall with brand new episodes. Please stay subscribed s…

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Philip Hughes Returns: Overcoming Challenges and Embracing AI 36:25

1M ago36:25

36:25

Did you like the episode? Send me a text and let me know!! What if the business you’ve been building for years isn’t the one that will set you free? In this episode of The Undiscovered Entrepreneur, Phil Hughes returns three years after his first appearance to share a powerful story of reinvention, resilience, and the courage to pivot. Phil takes u…

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Leslie Fiorenzo's One Year Update: From Entrepreneur Dreams to Reality 31:47

1M ago31:47

31:47

Did you like the episode? Send me a text and let me know!! Where Are They Now? Featuring Leslie Fiorenzo - The Undiscovered Entrepreneur #115 In this episode of The Undiscovered Entrepreneur, Jesse catches up with Leslie Fiorenzo, a business presentation coach, to discuss her entrepreneurial journey since they last spoke a year ago. Leslie shares h…

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Selling Without the Sleaze: The Founder’s Guide to Authentic Sales 58:17

1M ago58:17

58:17

Selling without the sleaze isn’t just possible—it’s the fastest way to build trust, win clients, and grow your business. In this episode of the Build Your Business Podcast, Matt and Chris Reynolds break down a founder-tested approach to sales that replaces pushy tactics with authentic problem-solving. You’ll learn how to lead with trust, diagnose r…

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Unlocking Success: Key Mindsets for New Entrepreneurs with PI-Powered Advice 11:03

1M ago11:03

11:03

Did you like the episode? Send me a text and let me know!! Mastering the Entrepreneurial Mindset with PI: Growth, Resilience, and More In this episode of 'Business Conversations With Pi,' host Skoob and his AI co-host Pi, tackle key questions that new entrepreneurs often ask. They dive into the critical types of mindsets beneficial for entrepreneur…

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From Traumatic Brain Injury to Digital Innovator: John Krotec's Inspiring Business Tale 1:00:00

2M ago1:00:00

1:00:00

Did you like the episode? Send me a text and let me know!! Overcoming Naysayers & Competing Against Yourself: The Adventure of Entrepreneur John In episode 114 of The Undiscovered Entrepreneur, host Skoob engages in an invigorating conversation with John, a dynamic entrepreneur who transformed a $40,000 investment into a $11 million outdoor gear bu…

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Why Core Values Matter for Founders: Define, Align, and Lead with Clarity 58:13

2M ago58:13

58:13

Why core values matter for founders isn’t just a philosophical question—it’s a strategic necessity. In this episode of the Build Your Business Podcast, Matt and Chris Reynolds break down how your personal values shape your business, influence hiring, drive decision-making, and define company culture. You'll learn how to discover your real—not aspir…

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Deep Work for Founders: How to Maximize Productivity & Crush Distractions 57:11

2M ago57:11

57:11

In this episode of the Build Your Business Podcast, Matt and Chris Reynolds unpack what may be the most important skill for any entrepreneur: deep work for founders. They reveal how to build rituals that trigger flow, how to design your day around peak focus hours, and why eliminating distractions is the first step toward real freedom in your busin…

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Entrepreneur Insights: Celebrating One Year with AI Co-Host Pi 10:41

2M ago10:41

10:41

Did you like the episode? Send me a text and let me know!! Essential Entrepreneurial Insights: One Year of Business Conversations with AI Co-Host Pi In this episode of Business Conversations With Pi, host Skoob and AI co-host Pi from Anthropic PI celebrate one year of discussions. They explore key topics crucial for new entrepreneurs, including min…

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Leading Through Chaos: How to Handle Business Crisis Without Panic 59:37

2M ago59:37

59:37

How do you lead your business when everything falls apart? In this episode of Build Your Business, Matt and Chris Reynolds share exactly how to handle business crisis—from late-night tech meltdowns and legal threats to complete operational shutdowns. They dive into real-world examples of how founders can stay calm, lead with confidence, and rally t…

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Navigating Entrepreneurial Challenges: Insights from a Successful PR Firm Owner 39:20

2M ago39:20

39:20

Did you like the episode? Send me a text and let me know!! Building Success from Humble Beginnings: An Entrepreneur's Journey with Nathan Miller - Episode 113 In episode 113 of The Undiscovered Entrepreneur podcast, host Skoob converses with Nathan Miller, founder of Miller!nk., to uncover his extraordinary journey from being Israel's chief speechw…

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Why Systems & SOPs Are the Secret to Business Growth 48:04

2M ago48:04

48:04

If your business feels like it’s running you—rather than the other way around—this episode is your roadmap out of chaos. Matt and Chris Reynolds break down why systems and SOPs (standard operating procedures) are the foundation of any successful, scalable business. You’ll learn how to start with simple wins, avoid common delegation mistakes, and bu…

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AI-Driven Business Insights: Unlocking Venture Capital and Startup Success with PI 10:26

2M ago10:26

10:26

Did you like the episode? Send me a text and let me know!! Unlocking Venture Capital for Entrepreneurs: Insights from Business Conversations with Pi In this episode of Business Conversations with Pi, host Skoob and AI co-host Pi delve into essential advice for new entrepreneurs seeking venture capital. They discuss building a solid business plan, n…

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Profit First for Founders: How to Take Control of Your Finances 1:08:14

3M ago1:08:14

1:08:14

Discover how to apply Profit First for Founders and finally gain control over your business finances. In this episode of the Build Your Business Podcast, Matt and Chris Reynolds walk you through the exact strategies they’ve used to move from cash burn to consistent profit—including financial dashboards, lean budgeting, and tactical cost-cutting. Wh…

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Entrepreneur Legal Tips: Avoid Critical Mistakes with Gordon Firemark 35:39

3M ago35:39

35:39

Did you like the episode? Send me a text and let me know!! Essential Legal Guidance for Entrepreneurs with Gordon Fire Mark In episode 112 of the Undiscovered Entrepreneur, host Skoob presents a deep dive into the essential legal aspects of entrepreneurship with digital creative lawyer Gordon Firemark. Gordon shares critical insights on the most si…

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Using Content to Build Trust and Win Clients 41:22

3M ago41:22

41:22

Struggling to get more clients? This episode of the Build Your Business Podcast shows you how using content to build trust and win clients is the most scalable, low-cost marketing strategy for entrepreneurs. Matt and Chris Reynolds break down why your founder story matters more than your brand, and how authenticity, vulnerability, and consistency d…

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Mastering AI Search: Essential Tips for Entrepreneurs and Business Builders 12:09

3M ago12:09

12:09

Did you like the episode? Send me a text and let me know!! Mastering AI Search Optimization for Entrepreneurs | Business Conversations with Pi In this episode of Business Conversations with Pi, hosted by Skoob along with virtual co-host Pi and AI assistant, the discussion revolves around essential strategies for optimizing business content to be ea…

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Churn: The Silent Killer of Your Business 41:15

3M ago41:15

41:15

Are you ignoring churn in your business? You might be losing more than you realize. In this episode of the Build Your Business podcast, Matt and Chris Reynolds reveal how churn is the silent killer of growth—especially in service-based and fitness businesses. They share actionable strategies to improve client retention, reduce drop-off, and turn sa…

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Jess Lindgren's Entrepreneurial Adventure: Lessons from Pat Flynn's Executive Assistant 46:35

3M ago46:35

46:35

Did you like the episode? Send me a text and let me know!! From Toxic Job to Dream Career: Jess Lindgren's Entrepreneurial Journey In episode 111 of The Undiscovered Entrepreneur podcast, host Skooby chats with Jess Lindgren, a seasoned freelance personal and executive assistant with over 20 years of experience. Jess shares her inspiring journey of…

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How Customer Focus Drives Business Growth 54:22

3M ago54:22

54:22

Customer focus isn’t just a buzzword—it’s the foundation of long-term business growth. In this episode of the Build Your Business podcast, Matt and Chris Reynolds share real-life stories—from a sudden family relocation to a dangerous carbon monoxide scare—that highlight why putting people first pays off in the business world. Learn how to build tru…

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Unlocking Entrepreneurial Success: The Power of Asking for Help 10:23

3M ago10:23

10:23

Did you like the episode? Send me a text and let me know!! Mastering the Stigma of Asking for Help in Entrepreneurship In this episode of Business Conversations with Pi, host Skoob and AI co-host Pi, created by the innovative minds at Anthropic, delve into the importance of overcoming the stigma associated with asking for help in the entrepreneuria…

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Why Online Coaching Beats In-Person Coaching: The Freedom, Efficiency, & Value Advantage 24:03

3M ago24:03

24:03

Is online coaching actually better than in-person coaching? In this episode of the Barbell Logic Coaching Success Series, Matt Reynolds shares why online coaching offers unmatched freedom, better financial efficiency, and stronger client results than traditional in-person sessions. Drawing on decades of experience both in gyms and running TurnKey C…

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"Where are they Now?" Special Follow Up Episode with the Prince Of Positivity 40:14

4M ago40:14

40:14

Did you like the episode? Send me a text and let me know!! Unlock Your Potential: The Power of Happiness and Mindset with Spencer Jones | Episode 110 In episode 110 of 'The Undiscovered Entrepreneur,' Skoob from Pod Nation Media Network interviews the inspiring 'Prince of Positivity,' Spencer Jones. Spencer discusses his journey from a struggling m…

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The Trust Equation with Andrew Jackson: How to Build Stronger Business Relationships 57:17

4M ago57:17

57:17

What makes people trust you in business—and what breaks that trust without you even realizing it? In this episode of Build Your Business, Matt and Chris Reynolds sit down with Andrew Jackson, COO of TurnKey Coach, to unpack The Trust Equation, a framework rooted in real leadership, lean systems, and years of experience. Whether you're leading a tea…

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Mastering Entrepreneurial Challenges: Fear, Failure, and Confidence-building 11:40

4M ago11:40

11:40

Did you like the episode? Send me a text and let me know!! Overcoming Fear and Embracing Failure in Entrepreneurship In this episode of Business Conversations With Pi, host Skoob and virtual co-host Pi—an AI assistant created by Anthropic—discuss the common fears and doubts that plague new entrepreneurs. The duo explores strategies for reframing fa…

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How to Fire Someone: A Business Owner’s Guide to Tough Conversations 46:57

4M ago46:57

46:57

Firing someone is one of the hardest parts of leadership—but avoiding it can cost your business even more. In this episode of Build Your Business, Matt and Chris Reynolds break down how to fire someone the right way: with clarity, compassion, and professionalism. Whether it's your first time or you're trying to improve your process, you'll learn ho…

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From Basement Beginnings: How David Jackson Built a Podcast Empire 1:04:23

4M ago1:04:23

1:04:23

Did you like the episode? Send me a text and let me know!! Getting Started & Building Success in Podcasting with Dave Jackson Welcome to Episode 109 of The Undiscovered Entrepreneur! In this episode, Skoob discusses the new upcoming course designed to help aspiring entrepreneurs get started. Skoob introduces his guest, Dave Jackson, founder of the …

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Effective Delegation for Perfectionists: How to Let Go Without Lowering Standards 42:09

4M ago42:09

42:09

📄 Are you stuck doing everything yourself because no one else can do it “right”? In this episode of Build Your Business, Matt and Chris Reynolds break down why perfectionists struggle with delegation—and how to fix it. Learn how to build trust, communicate expectations clearly, and use systems that protect your standards without burning you out. Di…

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Business Growth Hacks: AI and Marketing for Startup Success 10:18

4M ago10:18

10:18

Did you like the episode? Send me a text and let me know!! Top Marketing Strategies for New Entrepreneurs with AI Insights In this episode of 'Business Conversations with Pi,' host Skoob and AI co-host Pi, created by Anthropic, delve into essential marketing strategies for new entrepreneurs. They discuss effective techniques such as content marketi…

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When Important Becomes Urgent: How to Prioritize What Actually Matters 28:32

4M ago28:32

28:32

As a business owner, it's easy to push off the things that really matter—your family, your health, your strategic thinking—because they're not screaming for attention. But eventually, they will become urgent. In this episode, Matt Reynolds shares how he cleared his schedule, tackled long-neglected priorities, and rediscovered what it means to lead …

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Transforming Challenges into Strengths: Nick's Bipolar Power 57:36

5M ago57:36

57:36

Did you like the episode? Send me a text and let me know!! Unlocking Entrepreneurial Potential: From Bipolar Diagnosis to Publishing Success In episode 108 of The Undiscovered Entrepreneur, host Skoob welcomes Nick, a gifted bipolar writer who has transformed her mental health journey into a successful publishing business. The episode delves into N…

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Take Some Time Off: How Rest Makes You a Better Leader 19:12

5M ago19:12

19:12

In this episode, Matt Reynolds shares why learning to take some time off might be the smartest thing you do as a business owner. He unpacks how intentional rest can increase creativity, sharpen your strategic thinking, and actually improve your output as a leader. Whether it’s a simple weekend away or a longer retreat, Matt offers practical steps f…

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Leadership Skills 101: Driving Your Startup with Confidence and Strategy 11:34

5M ago11:34

11:34

Did you like the episode? Send me a text and let me know!! Mastering Leadership Skills: Entrepreneurial Insights with AI Co-Host Pi In this episode of 'Business Conversations with Pi,' Skoob and AI co-host Pi discuss the essential leadership skills necessary for new entrepreneurs. They cover topics such as effective communication, delegation, leadi…

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Pivoting for Growth: How Founders Spot Opportunities and Adapt 43:18

5M ago43:18

43:18

How do you know when it’s time to pivot—and how do you pivot without blowing everything up? 🚀Matt and Chris Reynolds break down real-world strategies for spotting opportunity, adapting to market shifts, and making founder pivots that fuel real business growth. Whether you’re navigating slow sales, customer churn, or big market changes (like AI!), t…

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Launching First: Unveiling Success in Digital Product Markets with David 52:31

5M ago52:31

52:31

Did you like the episode? Send me a text and let me know!! Turning Failures into Success: A Conversation with David on Entrepreneurial Insights In episode 107 of The Undiscovered Entrepreneur, host SC interviews David, an entrepreneur with 35 years of software expertise. David shares his journey of founding a successful software company that grew t…

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Embracing Remote Work: How Founders Build Freedom & Output 33:33

5M ago33:33

33:33

In this episode of Build Your Business: From Fear to Freedom, Matt Reynolds and Chris Reynolds dive deep into the powerful benefits of embracing remote work—and why they’ll never return to a traditional office setup. From unlocking personal freedom to building high-performing teams across time zones, remote work isn’t just a lifestyle change—it’s a…

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Navigating Information Overload: Essential Insights for Entrepreneur 10:35

5M ago10:35

10:35

Did you like the episode? Send me a text and let me know!! Mastering Information Overload: Insights from Pat Flynn on Lean Learning In this episode of Business Conversations with Pi, host Skoob and AI co-host Pi delve into essential questions for new entrepreneurs, discussing strategies to manage information overload. Featuring insights from Pat Fl…

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The Power of Thinking Time to Unlock Founder Potential 37:20

5M ago37:20

37:20

Quiet reflection might be the most powerful leadership tool you're not using. In this episode of Build Your Business, Matt and Chris explore how "thinking time" fuels strategic clarity, innovation, and sustainable leadership. Unlocking Founder Potential Starts with Thinking Time Intentional solitude creates space to lead, not just operate. Thinking…

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Entrepreneurial Wisdom: Pat Flynn's Strategies as Lean Learning Author and SPI Podcast Host 1:04:08

5M ago1:04:08

1:04:08

Did you like the episode? Send me a text and let me know!! Pat Flynn Unveils 'Lean Learning' and Shares Entrepreneurial Wisdom In this special episode of The Undiscovered Entrepreneur, host Skoob finally gets to interviews Pat Flynn, an esteemed entrepreneur and author, who shares insights from his newly released book, 'Lean Learning: How to Achiev…

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Overcoming Founder Isolation: Break the Cycle of Overwork & Anxiety 41:29

6M ago41:29

41:29

Feeling like you’re carrying the entire business on your shoulders? You’re not alone. In this vulnerable episode of Build Your Business, Matt and Chris talk openly about the emotional weight of being a founder—and how to break free from the loop of overwork, anxiety, and isolation. 1. What Founder Isolation Really Feels Like More than being alone—i…

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From Prototype to Market: A Guide for Aspiring Entrepreneurs 11:54

6M ago11:54

11:54

Did you like the episode? Send me a text and let me know!! Launching Your Physical Product: Prototyping to Marketing In this episode of 'Business Conversations With Pi,' Skoob and his AI co-host, Pi, delve into the essential steps for new entrepreneurs launching physical products. The discussion offers comprehensive advice on market research, desig…

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The Art of Sales Without the "Sales Tactics" 58:17

6M ago58:17

58:17

Sales doesn't have to feel sleazy or scripted. In this episode of Build Your Business, Matt and Chris Reynolds explore how to master the art of sales by being authentic, problem-focused, and client-centered. The Power of Authenticity in Sales The best salespeople lead with honesty and care. Build trust through real, meaningful conversations. Focus …

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Facing Hurdles in Business: Emily Vernon's Authentic Tale 33:36

6M ago33:36

33:36

Did you like the episode? Send me a text and let me know!! Overcoming Perfectionism and Imposter Syndrome with Emily Vernon In this episode of The Undiscovered Entrepreneur, host Skoob interviews Emily Vernon, founder of Vice Versa Strategy. Emily shares her entrepreneurial journey from a 12-year corporate fashion career to building a successful di…

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Hiring Your First Employee: Key Considerations for Entrepreneurs 44:52

6M ago44:52

44:52

Hiring your first employee is one of the biggest decisions you’ll make as a business owner. In this episode of Build Your Business, Matt and Chris Reynolds explore everything you need to know before making that first hire—from financial readiness to ensuring a strong cultural fit. Are You Ready to Hire Your First Employee? Hiring too soon—or withou…

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Navigating Patents and Business: AI-Powered Entrepreneurial Guide 11:39

6M ago11:39

11:39

Did you like the episode? Send me a text and let me know!! Decoding Startup Success: Unique Ideas, Patents, and IP with Pi In this episode of 'Business Conversations with Pi', host Skoob and AI co-host Pi, from Anthropic, delve into key questions facing new entrepreneurs. They offer thorough, actionable advice on how to determine if a startup idea …