Episodes
April 7, 2026
Solopreneur Time Management: How to Move From Daily Busywork to High-Impact Output
Did you like the episode? Send me a text and let me know!! Maker Schedules for Solo Founders: How to Scale Without Burnout Are you a solo founder frantically laying down train tracks while the train is speeding right behind you? In this episode, we tear up generic "hustle culture" to build a customized, energy-driven time management engine specifically for the solopreneur. Learn how to ditch the busywork, protect your deep creative focus, and scale your business without breaking yourself in t...
March 31, 2026
How To Discover Your Perfect Business Idea, Validate It And Launch It This Year | Jason VanDevere Dream Driven
Did you like the episode? Send me a text and let me know!! The Undiscovered Entrepreneur | Jason VanDevere | Dream Driven & Goal Crazy Planner Episode Summary Jason VanDevere walked away from a fourth-generation car dealership empire to build something that actually lit a fire inside him. In this episode, Jason breaks down how he created the Goal Crazy Planner, built a real estate portfolio of 34 units, and wrote his book Dream Driven — all by choosing passion over a paycheck. Timestamps...
Guest: Jason VanDevere
March 24, 2026
Zero Click Search Is Killing Creator Traffic — Here's How to Win With AI Answer Engines Instead
Did you like the episode? Send me a text and let me know!! How to Win at AI Search: The Complete Audience Building Blueprint for Creators Stop shouting into the digital void. In this episode, we break down the exact system for building an audience using AI search optimization, TikTok SEO, and podcast growth strategy — starting from absolute zero. What You'll Learn: Why "build it and they will come" is killing your growthHow AI tools like ChatGPT, Perplexity, and Google AI Overviews are the ne...
March 17, 2026
Where Are They Now? Marketing CEO Christy O'Connor on Agency Growth, AI Workflows and Scaling With Intention
Did you like the episode? Send me a text and let me know!! Where Are They Now? Catching Up With Christy O'Connor | Episode Skooby reunites with marketing veteran Christy O'Connor, President & CEO of O'conCo Marketing, to discuss business growth, AI automation, scaling with intention, and the foundations every new entrepreneur needs. 🎙️ Guest: Christy O'Connor 🌐 Website: oconcomarketing.com ⏱️ Episode Timestamps [00:00:00] — Introduction & Christy's background [00:02:00] — Shift...
Guest: c
March 10, 2026
How to Test Market Demand for $0 Using Lean Startup Principles
Did you like the episode? Send me a text and let me know!! How to Validate Your Business Idea Without Building a Single Thing Ever had a "billion-dollar idea" only to have it flop at launch? In this episode, we pull back the curtain on why most startups fail and—more importantly—how you can ensure yours doesn't. We’re exploring the frameworks of Alberto Savoia, Strategizer, and Rob Fitzpatrick to help you find the truth before you spend a dime on engineering. Key Timestamps: [00:01:30] The FL...
March 3, 2026
Why You Should Celebrate Failure (And How to Do It Right) 3 of 3
Did you like the episode? Send me a text and let me know!! Successful Podcaster: Redefining Failure & Fear Stop letting the "What If" spiral paralyze your progress. In this final episode of our three-part series, we dive deep into why failure isn't the end of the road—it’s the map. We explore how to take the negative energy of fear and transform it into a tool for entrepreneurial growth. Key Takeaways: The FAIL Acronym: Learn why failure is simply your First Attempt In Learning. The Powe...
Guest: JD Skoob
Feb. 24, 2026
The Longevity Economy Explained: Why Aging is the Biggest Business Opportunity of 2026
Did you like the episode? Send me a text and let me know!! The Longevity Dividend: Why Aging is the Single Largest Business Opportunity of the Century What if the "silver tsunami" isn't a crisis, but the most significant economic engine of our time? While the world worries about aging populations, the data reveals a startling truth: the 60+ demographic now accounts for 27% of global spending and possesses the cognitive power of people decades younger. In this episode of Business Conversat...
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Feb. 17, 2026
Are You a Perfectionist or Just Scared to Launch ( part 2 of 3 )
Did you like the episode? Send me a text and let me know!! Stop Waiting for Perfect: How Perfectionism Kills Your DreamsEpisode Summary Perfectionism isn't protection—it's procrastination in disguise. Discover why "good enough" is the only path to greatness and how waiting for the perfect moment costs you opportunities, time, and money. Learn to launch your "ugly babies" and use real-world feedback instead of endless revisions. What You'll Learn Why perfectionism is actually a mask for fearHo...
Guest: JD Skoob
Feb. 10, 2026
Why Do 73% of Delegation Attempts Fail? How to Scale with Global Talent
Did you like the episode? Send me a text and let me know!! Escaping the Competence Trap: Why Delegation Fails & How to Spot AI Hiring Fraud Are you a CEO or just the world’s most expensive janitor? In this episode of Business Conversations with PI, we dive deep into the "Superman Complex" and the hidden traps that stop entrepreneurs from scaling. We break down the mathematical framework of the Zone of Genius, why 73% of delegation attempts fail, and the terrifying new rise of AI deepfak...
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Feb. 3, 2026
How to Overcome Imposter Syndrome: The Entrepreneur’s Guide (Part 1 of 3)
Did you like the episode? Send me a text and let me know!! Overcoming Imposter Syndrome: Turn Self-Doubt Into Your Success CompassEpisode Summary Discover how to transform imposter syndrome from a career-blocking obstacle into a powerful navigation tool for entrepreneurial success. Learn practical strategies to overcome self-doubt, stop overworking to prove yourself, and embrace your accomplishments. What You'll Learn About Imposter Syndrome How to recognize when you're crediting success to l...
Guest: JD Skoob
Jan. 27, 2026
Why Do I Feel Dread on Sundays? Decoding the Alarm Bell of Career Misalignment
Did you like the episode? Send me a text and let me know!! Episode Summary Do you feel a pit of dread in your stomach every Sunday afternoon? You aren't alone. In this deep dive, we decode the "Sunday Scaries" not as a symptom to be suppressed, but as a vital alarm bell from your inner self. We analyze insights from top psychologists, entrepreneurs, and mindset experts to reveal why your body physically rejects your current routine. We explore the concept of the "Zone of Genius" (popularized b...
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Jan. 20, 2026
How Fear Became Fuel: Selling a $200M Company After Quitting at the Worst Possible Time
Did you like the episode? Send me a text and let me know!! From $0 to Million-Dollar Launch: How Justin Bannon Built a $200M Company in 2008's Financial Crisis What do you do when the world's economy collapses? If you're Justin Bannon, you quit your dream job at General Electric and launch a business anyway. Discover why starting during a crisis might be your biggest advantage and why talking to people matters more than perfecting your product. What You'll Learn: ✅ Why 2008's financial cri...
Guest: justin banner
Jan. 13, 2026
Pi & Piet Beat Imposter Syndrome & Stop Burnout
Did you like the episode? Send me a text and let me know!! Beat Imposter Syndrome & Stop Burnout: Practical Strategies for High Achievers Feel like a fraud despite your success? You're not alone. In this deep dive, we unpack imposter syndrome—the psychological state where you believe you're undeserving despite overwhelming evidence of your achievements—and reveal actionable strategies to break free. What You'll Learn: ✅ Why high achievers attribute success to luck instead of skill ✅ The "survi...
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Jan. 6, 2026
I Didn't Hit My Business Goals—Here's Why That's Actually Good News for New Entrepreneurs
Did you like the episode? Send me a text and let me know!! 2026 Kickoff: The Domino Effect of Goals & Embracing the Hurdles Episode Summary Welcome to the first episode of 2026! In this transparent and vulnerable episode, host SC Jesse Blo reflects on the journey through 2025, reviewing the hits, the misses, and the unexpected wins. Jesse dives into the concept of the "Domino Effect"—how missing a specific target can still knock down barriers and lead to even bigger opportunities. Join the "SC...
Guest: JD Skoob
Dec. 30, 2025
Decoding the Future: How to Build an AI-Powered Business
Did you like the episode? Send me a text and let me know!! AI-Driven Business Playbook: Scaling Your Startup with Pi Welcome back, Scoobelievers! In this episode of Business Conversations with Pi, host Jesse (SKoob) and AI co-host Pi dive deep into how entrepreneurs can leverage Artificial Intelligence to gain a massive competitive advantage. Whether you're a first-time founder or a seasoned builder, this episode provides a tactical roadmap for integrating AI into your daily operations. Key Tak...
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Dec. 23, 2025
How to Hire Remote Workers: Why 73% Fail & How to Succeed | Nearshore Staffing with Luis D
Did you like the episode? Send me a text and let me know!! How to Hire Remote Workers: Why 73% Fail & How to Succeed | Nearshore Staffing with Luis DEpisode Description Serial entrepreneur Luis D reveals why 73% of offshore hiring fails and how his REMOTE Intelligence Framework achieves 95% success. Learn to hire Latin American talent at 60-70% cost savings, avoid AI resume fraud, and scale your startup faster. Luis built the first Latin American tech startup to get US VC funding and pion...
Guest: Luis Derechin
Dec. 15, 2025
Vulnerability in Business: A Strategic Guide for Entrepreneurs
Did you like the episode? Send me a text and let me know!! Vulnerability as a Startup Strength | Business Conversations with Pi Welcome to another episode of Business Conversations with Pi, where AI-powered insights meet real entrepreneurial challenges! In this episode, host SC and virtual co-host Pi dive deep into why vulnerability is a powerful asset for startup founders and business leaders. Whether you’re brainstorming your first business idea or scaling your startup, this episode is packed...
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Dec. 9, 2025
From Streets to Success: Jerry Brazie on Building $500M in Revenue
Did you like the episode? Send me a text and let me know!! From Streets to Success: Jerry Brazie on Building $500M in Revenue | The Undiscovered Entrepreneur Episode Description Jerry Brazie went from living in a $25/week flophouse at 17 to building and selling a dozen businesses generating nearly $500 million in revenue. In this raw, unfiltered conversation, Jerry shares the pivotal moment at 14 that changed everything, why "everything is your fault" became his superpower, and the brutal t...
Guest: Jerry Brazie
Dec. 2, 2025
Conquer the Fear of Success: Entrepreneurial Insights and Strategies
Did you like the episode? Send me a text and let me know!! Jesse (Skoob) & Pi (AI Assistant) Focus: Entrepreneur Mindset, Self-Sabotage, Psychology of Success Why do entrepreneurs often self-sabotage just when they start winning? In this episode of Business Conversations with Pi, Jesse and his AI co-host explore the Upper Limit Problem—a psychological barrier that caps our happiness and success—and provide a 5-step roadmap to break through it. 💡 FAQ: Understanding the Fear of Success What...
Nov. 25, 2025
Engage, Evolve, Excel: Carrolee's Journey from Hot Mess to Success
Did you like the episode? Send me a text and let me know!! The Undiscovered Entrepreneur Podcast: Carrolee Moore on Authentic Visibility & Overcoming Failure Host: Jesse Guest: Carrolee Moore, Founder of Podcast Pitching Society Episode Summary: Join Jesse and Carrolee Moore as they dive into the realities of entrepreneurship, the power of authentic branding, and how to turn failures into stepping stones. Carrolee shares her journey from music PR dreams to building a multi-six-figure bu...
Guest: Carrolee Moore
Nov. 17, 2025
Navigating Entrepreneurship: How to Add and Grow Business Value
Did you like the episode? Send me a text and let me know!! Business Conversations With Pi – How to Add and Grow Business Value Todays discussion covers how to define and measure value in business, strategies for growing a company, and the best ways to find top talent. The episode also features expert book recommendations to help listeners deepen their understanding of value creation and business growth 00:00 – Introduction Meet host KU and AI co-host Pi. Discover how AI can help entrepreneurs...
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Nov. 11, 2025
From PR to Podcast: Sandy Sterling Unzips Fear and Ignites Entrepreneurial Spirit
Did you like the episode? Send me a text and let me know!! 🎧 Show Notes: The Undiscovered Entrepreneur ft. Sandy Sterling (Fear Unzipped) Join host Skoob and guest Sandy Sterling, founder of Fear Unzipped, as they explore the journey from Hollywood PR to podcasting, the science of fear, and the power of authenticity in entrepreneurship. Key Topics: Launching before you’re “ready” (the 70% rule)Neuroscience & metaphysics of fearOvercoming imposter syndrome & perfectionismThe ripple eff...
Guest: Sandi Serling
Nov. 4, 2025
Stay Motivated as an Entrepreneur: Insights from AI and Expert PI
Did you like the episode? Send me a text and let me know!! Business Conversations with Pi – Episode: Entrepreneurial Motivation & Mindset Welcome to another episode of Business Conversations with Pi, where AI-powered insights meet real entrepreneurial challenges! In this episode, host Jesse and virtual co-host Pi dive deep into the essential topic of motivation for entrepreneurs, sharing actionable strategies, expert advice, and top book recommendations to help you stay driven on your bus...
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Oct. 28, 2025
From Nightlife DJ to Marketing Mogul: Brandon Wellington on Entrepreneurial Success
Did you like the episode? Send me a text and let me know!! 🎧 Show Notes: The Undiscovered Entrepreneur with Brandon – From DJ Booth to Business Breakthroughs Unlock the secrets of entrepreneurial resilience and growth in this inspiring episode featuring Brandon, a former DJ turned marketing agency founder. Discover actionable strategies, real-life stories, and mindset shifts that will help you get across your own start line. Timestamps & Highlights: 00:00 – Introduction: Meet Brandon, DJ to en...