Undiscovered Entrepreneur : Get Across The Start Line

Jesse Blount
  • 4.9 (27)
  • Entrepreneurship
  • Updated Weekly

Are you ready to launch your startup but feeling stuck? "Startup Success: Overcoming Entrepreneurial Obstacles" is the must-listen podcast for aspiring entrepreneurs and small business owners. Host Skoob guides you through the challenging world of startups, focusing on conquering the "4 Pillars of Stop" that hold many entrepreneurs back:1. Imposter Syndrome2. Perfectionism3. Fear of Failure4. F.E.A.R. (False Evidence Appearing Real)Each episode features real stories from startup founders and solopreneurs who've faced these common hurdles. Learn actionable strategies to boost your confidence, embrace imperfection, and turn failures into stepping stones.Key topics include:- Mindset shifts for entrepreneurial success- Practical tips for launching your business- Overcoming self-doubt and procrastination- Building resilience in the face of setbacksWhether you're dreaming of creating a tech startup, launching an e-commerce brand, or starting a freelance career, this podcast provides the motivation and tools you need to take action.Join our growing community of go-getters who live by the mantra: "I Can, I Am, I Will, And I'm Doing It Today!"Subscribe now and take your first step towards entrepreneurial success. New episodes drop weekly, packed with insights to fuel your startup journey.#StartupTips #EntrepreneurMindset #SmallBusinessSuccess #OvercomingFear #StartupMotivation

  1. 2d ago

    Turn Your LinkedIn & X Profile Into an Inbound Lead Machine

    Did you like the episode? Send me a text and let me know!! Inbound leads close at 14.6%. Outbound closes at 1.7%. If you're still relying on cold outreach to fill your pipeline, you're working eight times harder for a fraction of the results. In this episode of Business Conversations with Pi and Piette 2.0, PI and Piette answer a listener's question from tuepodcast.net/askpi: how do I build a personal brand on LinkedIn or X to generate inbound leads? The answer is a complete 2026 blueprint — from profile optimization and algorithm mechanics to content strategy, lead magnets, and the one reframe that changes everything: you're not giving away your secrets, you're proving you're the only one qualified to execute them. What You'll Learn: Why inbound leads convert 8-9x better than cold outreach — and the psychology behind the gapWhy LinkedIn now drives 75-85% of all B2B social media leadsHow LinkedIn capped connection requests to 100-200 per week — making inbound mandatoryWhat a personal brand actually is in 2026 (hint: it's not a color scheme)How to write a hyper-specific positioning line that filters the right buyers instantlyWhy your LinkedIn profile should function as a landing page, not a resumeWhat "true flexing" looks like — and why objective proof beats empty adjectives every timeHow LinkedIn's new 360 Brew AI ranking system works and what kills your confidence scoreWhy the March 2026 authenticity update killed polls, engagement bait, and external linksWhy PDF carousels pull a 6.6% engagement rate (and what dwell time has to do with it)Why one deep post per week beats five shallow ones — every timeThe content flywheel: one foundational piece that fuels your entire week of contentThe Ty Mumford stump grinding method: how radical authenticity builds fierce loyaltyWhy giving away your best frameworks for free is the fastest way to get paying clientsHow to create ideological enemies — and why it magnetizes your ideal tribeThe three-step inbound post funnel: awareness → education → soft actionWhy lead magnets and email lists are the ultimate finish line of every social strategyWhy your email list is the only audience you actually ownTimestamps: [00:00:00] – The Vacuum Salesman vs. The Welcoming Storefront: The Core Analogy[00:01:30] – The Listener Question & Today's Mission[00:02:30] – Why Inbound Converts 8-9X Better Than Outbound[00:03:00] – 14.6% vs. 1.7%: The Psychology of Asymmetrical Trust[00:03:30] – LinkedIn Drives 75-85% of All B2B Social Leads[00:04:00] – Why LinkedIn Killed Mass Outreach (100-200 Connection Cap)[00:04:30] – What a Personal Brand Actually Is in 2026[00:05:00] – The Hyper-Specific Positioning Line That Filters Buyers Instantly[00:06:00] – X Platform Technical Requirement: Your Profile Must Be 100% Public[00:06:30] – Treating Your LinkedIn Profile as a Landing Page[00:07:00] – The Banner Image as Window Display: Filtering In and Filtering Out[00:07:30] – The About Section: A Sales Letter Disguised as an Introduction[00:08:00] – True Flexing: Why Objective Proof Beats Empty Adjectives[00:09:30] – Building the Storefront: Profile Optimization Complete[00:09:45] – The 2026 Algorithm Landscape: Views Down 50%, Engagement Down 25%[00:10:00] – LinkedIn's 360 Brew AI: How the Confidence Score Works[00:11:00] – Why Posting Off-Topic Kills Your Reach Across the Board[00:11:30] – The March 2026 Authenticity Update: What Got Killed[00:12:00] – Polls Are Dead: 0.07% Engagement Rate Explained[00:12:30] – What the Algorithm Is Actually Rewarding Now[00:12:45] – PDF Carousels: 6.6% Engagement Rate and the Dwell Time Mechanic[00:13:30] – Why One Deep Post Per Week Beats Five Shallow Ones[00:14:00] – The Golden Posting Window: Tuesday-Thursday, 9-11 AM[00:14:30] – The Content Flywheel: One Piece, Full Week of Content[00:15:30] – Humanizing the Brand: Why Authenticity Is a Technical Advantage[00:16:00] – Ty Mumford and Stump Grinding: The Power of Documenting Your Reality[00:17:00] – Give Away the Manual: Why Free Frameworks Attract Paying Clients[00:18:00] – Creating Ideological Enemies to Magnetize Your Tribe[00:19:00] – The Three-Step Inbound Post Funnel: Awareness → Education → Action[00:20:30] – Lead Magnets and Why Email Is the Only Audience You Own[00:22:00] – Final Thought: How Will Your Brand Retain Its Human Soul?[00:23:00] – Submit Your Question & Wrap-UpSubmit Your Question: 🔗 tuepodcast.net/askpi — Pi & Piette build a deep dive around your question. Subscribe & Share: If this episode changed how you think about social media, cold outreach, or what a personal brand actually is — subscribe, leave a review, and share it with every expert who's been hiding their best work behind a pitch deck nobody asked for. 🎙️ Business Conversations with Pi and Piet 2.0 — Real questions. AI insights. Unlimited potential. Do you want to know what is your worst Hurdle is so you know what you want to do first to get across the start line?? Go to tuepodcast.net/quiz to get your 3 minute assessment right now and find out what your most prevalent hurdle is and how to start to overcome it! tuepodcast.net/quiz For a 15% discount on your first purchase go RYZEsuoerfoods.com use code PODNA15  Thank you for being a Skoobeliever!! If you have questions about the show or you want to be a guest please contact me at one of these social medias Twitter......... ..@djskoob2021 Facebook.........Facebook.com/skoobami Instagram.....  instagram.com/uepodcast2021 tiktok....... @djskoob2021 Email............... Uepodcast2021@gmail.com Skoob at Gettin' Basted Facebook Page Across The Start Line Facebook Community Find out what one of the four hurdles of stop is affecting you the most!! Black Friday coaching Sale now!! 65% off original price! go to stan.store/skoob to book your appointment and take advantage of this limited time offer! On Twitter @doittodaycoach doingittodaycoaching@gmailcom

    Turn Your LinkedIn & X Profile Into an Inbound Lead Machine

  2. Sep 1

    Lizzie Thomas on Authenticity, Creative Health & Trusting the Detour

    Did you like the episode? Send me a text and let me know!!   Lizzie spent 15 years mastering the American Songbook. She was a dedicated New York City jazz vocalist steeped in Coltrane, Miles Davis, Cole Porter, and Gershwin. And then she started hearing original melodies in meditation and dreams — and she followed them. Now she's releasing her second all-original album, heading to Carnegie Hall, and more authentically herself than she has ever been.  In this episode of Undiscovered Entrepreneur: Get Across the Start Line, jazz singer-songwriter, arranger, producer, record label founder, and author Lizzie Thomas joins Skoob for one of the most soulful and wide-ranging conversations the show has ever had. From creative health and imposter syndrome to the power of the subconscious and why authenticity is the only branding strategy that lasts — this episode is for every entrepreneur who's afraid to leave the lane they were trained for.  What You'll Learn:  Why stepping outside your own work — becoming a listener instead of the creator — unlocks creative power and breaks perfectionismWhat "creative health" means and why it's the most overlooked entrepreneur skillWhy you have to release in order to receive — and what that looks like in practiceHow imposter syndrome is rooted in self-worth — and why knowing who you are is the cureWhy branding is authenticity — and why polished perfection is now working against you in the age of AIHow Lizzie started hearing original music in meditation and dreams — and what that teaches us about the subconsciousThe question-before-sleep technique for accessing answers your waking mind can't findWhy Lizzie's "detour" away from the jazz canon became her greatest liberationWhy people are craving human imperfection right now more than everHow to make something your own: take the best of your mentors and add your own essenceRumi's quote on walking the path — and what it means for getting across the start lineLizzie's six-month plan: album release, touring NYC, LA, Germany, Italy, Carnegie Hall & the Grammys Timestamps:   [00:00:00] – Introduction & Welcome[00:01:30] – Meet Lizzie Thomas: Jazz Singer, Record Label Founder, Author & Musical Entrepreneur[00:03:00] – Musicians and Imposter Syndrome: Why Perfectionism Hits Differently in the Arts[00:03:30] – Stepping Out of the Song: How Objectivity Breaks Perfectionism[00:05:00] – Looking Outside the Bottle: Why You Can't See What You're In[00:06:00] – Creative Health: Rest, Release & Why Giving Yourself Permission Is the Hardest Part[00:07:30] – Brain Refreshers, Naps & the Art of Making Room for the Next Idea[00:08:00] – In Order to Receive, You Have to Release: The Philosophy of Creative Flow[00:10:00] – Imposter Syndrome Is a Self-Worth Problem — Here's the Real Fix[00:11:30] – You Can't Have a Tribe If You Don't Know Who You Are[00:12:30] – The House of Cards: What Happens When Branding Runs Ahead of Authenticity[00:13:00] – Rise by Lifting Others — But Know Yourself First[00:14:30] – Curiosity Is the Key to a Great Existence as a Human[00:15:30] – Rumi: "You Only Realize the Path Once You Start Walking the Path"[00:16:00] – The Pitfall She's Proud Of: Leaving the Jazz Canon to Find Her Own Voice[00:20:30] – Take the Best of Your Mentors and Make It Your Own[00:22:00] – The Subconscious as Creative Partner: Hearing Melodies in Dreams[00:22:30] – The Question-Before-Sleep Technique: How to Access Answers Your Waking Mind Can't Find[00:23:30] – Dream States and What We Can Access When We Stop Controlling[00:25:00] – One Piece of Advice for New Entrepreneurs: Find Out Who You Are First[00:26:00] – How Are You Making People Feel? The Question That Beats Any 10-Step Plan[00:27:30] – Authenticity IS the Brand — And Why It's More Urgent Than Ever[00:29:00] – Lizzie's Six-Month Plan: This Is Freedom, Carnegie Hall & the Grammys[00:31:30] – How to Find Lizzie Thomas Upcoming Shows & Releases: 🎵 Album: This Is Freedom — releasing August 12th (Goddess Legacy Records) 🎤 NYC: City Winery — September 19th 🎤 LA: Sunset Marquis Hotel — September 23rd 🎤 Frankfurt, Germany 🎤 North Italy (with press appearances) 🎤 Carnegie Hall — November 13th 🎤 Grammys — February Connect with Lizzie Thomas: 🌐 Website & Tour Dates: lizziethejazzsinger.com (Lizzie the Jazz Singer across all platforms) 📺 YouTube: Full music videos and performances 🎧 Spotify: Lizzie Thomas (includes live show listings) 📱 Instagram / TikTok / Facebook: @LizzieTheJazzSinger Subscribe & Leave a Review: If Lizzie's episode made you feel something — about who you are, what you're holding onto, or what you've been afraid to become — please subscribe, leave a review, and share it with someone who needs permission to take their detour. 🎙️ Undiscovered Entrepreneur: Get Across the Start Line — new episodes dropping regularly.   Do you want to know what is your worst Hurdle is so you know what you want to do first to get across the start line?? Go to tuepodcast.net/quiz to get your 3 minute assessment right now and find out what your most prevalent hurdle is and how to start to overcome it! tuepodcast.net/quiz For a 15% discount on your first purchase go RYZEsuoerfoods.com use code PODNA15  Thank you for being a Skoobeliever!! If you have questions about the show or you want to be a guest please contact me at one of these social medias Twitter......... ..@djskoob2021 Facebook.........Facebook.com/skoobami Instagram.....  instagram.com/uepodcast2021 tiktok....... @djskoob2021 Email............... Uepodcast2021@gmail.com Skoob at Gettin' Basted Facebook Page Across The Start Line Facebook Community Find out what one of the four hurdles of stop is affecting you the most!! Black Friday coaching Sale now!! 65% off original price! go to stan.store/skoob to book your appointment and take advantage of this limited time offer! On Twitter @doittodaycoach doingittodaycoaching@gmailcom

  3. Aug 25

    The David vs. Goliath Playbook for Competing Against Big, Well-Funded Competitors

    Did you like the episode? Send me a text and let me know!!   In the late 1980s, a tiny startup called Qualcomm kept losing massive trucking contracts — not to better technology, not to a cheaper product, but to something that didn't even exist. Their competitor was selling a promise, a delay, a ghost. And Qualcomm almost died for it.  In this episode of Business Conversations with Pi and Piette 2.0, PI and Piette answer a listener's ultimate founder anxiety question from tuepodcast.net/askpi: "How do I compete in a saturated market against big, well-funded competitors?" The answer draws from Y Combinator archives, Forbes strategy pieces, startup veterans, and some of the most instructive David vs. Goliath business stories ever told — from Instacart vs. Amazon to Zappos vs. every retail giant in existence.  The conclusion? Your biggest competitive advantage isn't your brilliance. It's their comfort.  What You'll Learn:  Why obsessing over your competitor's every move is the single biggest strategic error a founder can makeThe race car driver analogy that explains why looking at the wall means hitting the wallThe Justin.tv story: how copying a competitor's feature caused two companies to waste their own runway simultaneouslyWhy vaporware is a psychological weapon — and how Qualcomm survived itWhy competing on price against a well-funded Goliath is always a death sentenceThe Willie Keeler "hit them where they ain't" strategy and the blue ocean approachHow Maxim Integrated built a billion-dollar company by serving the customers giants couldn't afford to bother withHow Prego's extra chunky sauce discovered a hidden one-third of the American market that nobody was servingHow Absolut Vodka carved out a premium niche in a market where the product is legally identical to every competitorWhy Zappos and Digi-Key weaponized speed and customer service to outmaneuver corporate giantsThe 100X rule: why being 30% better isn't enough — and how Instacart solved the avocado problem Amazon couldn'tHow Cruise beat Google's decade-long self-driving head start by seeking out the hardest problems on purpose Timestamps:   [00:00:00] – Introduction & The Listener Question[00:01:00] – Qualcomm vs. a Product That Didn't Exist: The Opening Hook[00:02:30] – The Classic Goliath Problem: How Every Ambitious Founder Gets Here[00:03:00] – The Race Car Driver Analogy: Why Looking at the Wall Means Hitting It[00:04:00] – Justin.tv (Later Twitch) and the Corporate Imposter Syndrome Trap[00:05:00] – The Blind Leading the Blind: When Both Competitors Are Copying Each Other's Mistakes[00:06:00] – The Theater Set Illusion: Why Your Competitor's PR Is Just Duct Tape and Panic[00:06:30] – Markets Support Multiple Winners: The Regional Bank Reality Check[00:07:00] – Stop Watching Competitors — Start Watching Alternatives[00:07:30] – Qualcomm's Full Story: Fighting Vaporware With a Real Product[00:08:30] – The Pork Chop Joke: Why Competing on Price Is the Fastest Way to Die[00:09:30] – Hawaiian Airlines vs. Southwest: How Well-Funded Giants Use Cross-Subsidization to Destroy You[00:10:30] – Willie Keeler's "Hit Them Where They Ain't" — The Blue Ocean Approach[00:11:00] – Maxim Integrated: Building a Billion-Dollar Empire on the Long Tail Nobody Else Wanted[00:12:30] – Howard Moskowitz and Prego's Extra Chunky Sauce: Finding the Hidden Cluster[00:13:30] – Absolut Vodka: Competing on Packaging When the Product Is Legally Identical[00:14:00] – The Meatball Shop & Bonobos: Do One Thing, Own It[00:14:30] – Weaponizing Speed and Customer Service: Your Two Asymmetrical Advantages[00:15:30] – Digi-Key: $2 Billion in Revenue With Zero Salespeople[00:16:30] – Zappos: How Human Customer Service Creates Loyalty Corporate Advertising Can't Buy[00:17:30] – The Psychology of the Sale: Addressing Hopes, Fears & Structural Tension[00:18:30] – What Happens When the Giant Wakes Up? The 100X Rule[00:19:30] – Instacart vs. Amazon: Why a Trillion-Dollar Company Couldn't Pick the Right Avocado[00:20:30] – Cruise vs. Google: Beating a 10-Year Head Start by Seeking the Hardest Problems[00:21:30] – Full Playbook Summary & the Final Provocative Thought[00:23:00] – Submit Your Question & Wrap-Up Companies & Stories Referenced: Qualcomm / Omnitracs, Justin.tv (Twitch), Shelby.tv, Maxim Integrated, Prego (Howard Moskowitz), Absolut Vodka, The Meatball Shop, Bonobos, Digi-Key, Zappos, Instacart vs. Amazon, Cruise vs. Google, Southwest vs. Hawaiian Airlines Submit Your Question: 🔗 Head to tuepodcast.net/askpi and Pi & Piette will build a deep dive around your question. Subscribe & Share: If this episode reframed how you think about competing against giants — subscribe, leave a review, and share it with a founder who's been staring at the wall instead of the track. 🎙️ Business Conversations with Pi and Piette 2.0 — Real questions. AI insights. Unlimited potential.   Do you want to know what is your worst Hurdle is so you know what you want to do first to get across the start line?? Go to tuepodcast.net/quiz to get your 3 minute assessment right now and find out what your most prevalent hurdle is and how to start to overcome it! tuepodcast.net/quiz For a 15% discount on your first purchase go RYZEsuoerfoods.com use code PODNA15  Thank you for being a Skoobeliever!! If you have questions about the show or you want to be a guest please contact me at one of these social medias Twitter......... ..@djskoob2021 Facebook.........Facebook.com/skoobami Instagram.....  instagram.com/uepodcast2021 tiktok....... @djskoob2021 Email............... Uepodcast2021@gmail.com Skoob at Gettin' Basted Facebook Page Across The Start Line Facebook Community Find out what one of the four hurdles of stop is affecting you the most!! Black Friday coaching Sale now!! 65% off original price! go to stan.store/skoob to book your appointment and take advantage of this limited time offer! On Twitter @doittodaycoach doingittodaycoaching@gmailcom

    The David vs. Goliath Playbook for Competing Against Big, Well-Funded Competitors

  4. Aug 18

    Who's Gonna Tell Her Story? David Dean on AI, Human Value in the Workplace

    Did you like the episode? Send me a text and let me know!!   A frontline worker broke into tears on a call with David Dean. She was afraid she wouldn't have a job in a year. That moment became the spark for a book — and for one of the most grounded, compassionate conversations about AI and human value in the workplace you'll ever hear.  In this episode of Undiscovered Entrepreneur: Get Across the Start Line, David Dean — author of An Inbox Between Us and self-described Business AI Realist — joins Skoob for a deep, thoughtful conversation about what AI actually means for real people at every level of an organization. Not the hype. Not the doomsaying. The real relationship between humans and AI — and why getting that relationship right is the defining challenge of this era.  What You'll Learn:  Why David left large enterprise to write a book nobody else was writing — for the people nobody else was talking toThe written contract vs. the unwritten contract: how organizations actually run vs. how they say they runWhy lived experience and lived consequence are the real reasons we hire humans — and why AI can't replace thatHow AI is like the movie Multiplicity — and why your copies aren't all the sameWhy 79% of the workforce are "AI survivalists" just trying to do their jobsWhat organizational self-awareness means and why it's the competitive advantage of the AI eraHow to use AI as a behavioral mirror — analyzing patterns across client meetings, team dynamics, and organizational challengesWhy the human touch is more valuable right now, not less, precisely because of AIThe Star Trek/Scotty analogy for how AI accelerates human decision-making without replacing itWhy David calls himself a Business AI Realist — and what that means for your team or companyDavid's six-month goal: speaking engagements and becoming a go-to ground-level AI voice for enterprise Timestamps:   [00:00:00] – Introduction & Welcome[00:01:00] – David's Background: From Enterprise Tech to the AI Era[00:02:00] – The Digital Journaling That Became a Book[00:03:00] – What the Hype Gets Wrong: Talking About AI From Too High Up[00:04:30] – Why David Felt Like "a Little Guy" — and Why That Didn't Stop Him[00:06:00] – You Are an Entrepreneur If You're Helping People[00:07:00] – AI as Tool, Not Replacement: The Entrepreneur's Perspective[00:08:00] – Why Companies Hire People: Lived Experience & Lived Consequence[00:09:00] – The Written Contract vs. the Unwritten Contract[00:10:00] – The Final Human Decision: Where Accountability Must Stay[00:11:00] – AI as a Relationship: Slow Down, Figure It Out, Cultivate It[00:12:00] – The Multiplicity Model: Using AI to Duplicate and Offload Yourself[00:13:30] – Debating Yourself With AI: Devil's Advocate, Customer Perspective & Idea Extraction[00:14:30] – Friendly Candor With AI: Using It to Challenge Your Own Thinking[00:15:00] – The Behavioral Record: What Patterns in Your Data Reveal About You and Your Business[00:17:00] – When AI Tells You to Go Have a Conversation Instead[00:18:00] – Humans Are Craving Human Touch — More Now Than Ever[00:19:00] – Star Trek's Scotty Analogy: AI Accelerates Decisions Without Making Them[00:20:30] – AI Is Flawed Because It Mimics Us — and That's Okay[00:23:00] – The Pitfall He's Proud Of: Getting Kicked Around Enough to Know Who He Is[00:24:30] – Authenticity and Quiet Trust: Why People Respect How You Operate Even If They Don't Like You[00:27:00] – The Moment That Sparked the Book: A Frontline Worker in Tears[00:29:00] – The 79% AI Survivalists and Why Someone Needs to Fight for Them[00:30:30] – What the Book Covers — and Why It's Written to Resonate 10 Years From Now[00:31:30] – The Book: An Inbox Between Us — Available Now[00:34:00] – David's Six-Month Goal: Speaking Engagements & the Business AI Realist Platform[00:37:00] – How to Find David, the Book & Connect on LinkedIn Book: 📚 An Inbox Between Us — David Christopher Dean Available at: Amazon, Barnes & Noble, Porchlight (print & e-book). Audiobook coming July. Connect with David Dean: 🌐 davidchristopherdean.com 💼 LinkedIn: David Christopher Dean 📰 Newsletter: Available on LinkedIn Subscribe & Leave a Review: If David's conversation made you think differently about AI, human value, and what we owe to the people just trying to keep their jobs — please subscribe, leave a review, and share this with someone who needs to hear that they matter in the age of AI. 🎙️ Undiscovered Entrepreneur: Get Across the Start Line — new episodes dropping regularly.   Do you want to know what is your worst Hurdle is so you know what you want to do first to get across the start line?? Go to tuepodcast.net/quiz to get your 3 minute assessment right now and find out what your most prevalent hurdle is and how to start to overcome it! tuepodcast.net/quiz For a 15% discount on your first purchase go RYZEsuoerfoods.com use code PODNA15  Thank you for being a Skoobeliever!! If you have questions about the show or you want to be a guest please contact me at one of these social medias Twitter......... ..@djskoob2021 Facebook.........Facebook.com/skoobami Instagram.....  instagram.com/uepodcast2021 tiktok....... @djskoob2021 Email............... Uepodcast2021@gmail.com Skoob at Gettin' Basted Facebook Page Across The Start Line Facebook Community Find out what one of the four hurdles of stop is affecting you the most!! Black Friday coaching Sale now!! 65% off original price! go to stan.store/skoob to book your appointment and take advantage of this limited time offer! On Twitter @doittodaycoach doingittodaycoaching@gmailcom

  5. Aug 11

    Stop Giving It Away for Free: How to Monetize Your Side Projects

    Did you like the episode? Send me a text and let me know!!   You have the expertise. You have the content. You're doing free coaching calls, running an alpha app on a tip jar, and sitting on years of teaching materials nobody is paying you for. How do you turn all of that into real, recurring income — without risking the paycheck that keeps the lights on?  In this episode of Business Conversations with Pi and Piette 2.0, PI and Piette answer a listener's layered, real-world question from tuepodcast.net/askpi: how to monetize coaching calls, a side app, and teaching experience into a low-risk paid offer without jeopardizing a current job. The answer is a four-part blueprint covering app monetization, digital product strategy, the hybrid marketplace model, and a four-step coaching close that makes selling feel natural.  What You'll Learn:  Why the tip jar model is a validation tool, not a business modelHow the freemium value ladder works — and why you never take away what's freeWhy in-app ads require hundreds of thousands of impressions to make $1,000/monthThe difference between consumables and non-consumables in app monetizationWhy Teachers Pay Teachers takes up to 45% of every sale — and the break-even math for owning your own storeThe hybrid marketplace strategy: use big platforms for discovery, your own store for retentionHow Jen Regan made $100,000 selling fourth-grade lesson plansMelinda Kitto's no bait-and-switch rule for coaching callsThe four-step transition formula to close a coaching sale naturallyWhy framing the pitch upfront actually relaxes the prospect instead of scaring them awayWhy massive pre-recorded courses are losing to personalized one-on-one coachingHow YouTube's Alpha AI targeting lets a side hustler compete on intent, not ad spendWhy charging for expertise delivers better results for your clients than giving it away free Timestamps:   [00:00:00] – Introduction & The Listener Question[00:01:00] – The 45% Hidden Tax on Ambition: Why Marketplaces Are Bleeding Your Profits[00:02:30] – The Low-Risk Constraint: Protecting the Primary Engine First[00:03:30] – Check Your Employment Contract: Non-Compete Clauses & Legal Guardrails[00:04:30] – The Battery Backup Model: Side Hustle as Safety Net, Not Full Replacement[00:05:30] – From Tip Jar to Value Ladder: Moving Beyond Unpredictable Goodwill[00:06:30] – The Bottom Rung: Keep Core Functionality Free[00:07:00] – The Math on In-App Ads: Why You Need Hundreds of Thousands of Impressions for $1K/Month[00:07:30] – Consumables vs. Non-Consumables: The Freemium Mechanics Explained[00:08:30] – The ChatGPT Model: Never Take Away the Free, Only Add Exclusive Value[00:09:00] – Monetizing Teaching Experience: Jen Regan's $100K Lesson Plan Story[00:10:00] – Why Teachers Pay Teachers Takes Up to 45% — and the Break-Even Math[00:11:00] – The Hybrid Strategy: Marketplace for Discovery, Own Store for Retention[00:12:00] – Monetizing the Exhaust: Packaging Existing Materials Into Premium Digital Products[00:13:00] – Transitioning Free Coaching Calls Into High-Ticket Paid Coaching[00:13:30] – Melinda Kitto's No Bait-and-Switch Rule[00:14:00] – The Four-Step Transition Formula to Close Coaching Sales Naturally[00:15:30] – Why Transparency Relaxes the Prospect Instead of Scaring Them[00:16:30] – The Wolf Pack Model: Why Personalized Coaching Is Beating Pre-Recorded Courses[00:17:30] – YouTube Advertising: Aleric Heck's Value Add Formula[00:18:30] – Alpha AI Targeting: How to Reach Exact Buyers Without a Massive Budget[00:20:30] – Full Blueprint Recap: Four Immediate Steps[00:21:30] – Final Thought: Charging for Expertise Delivers Better Results for Your Clients[00:22:30] – Submit Your Question & Wrap-Up The Four-Step Coaching Transition Formula (Melinda Kitto):   ✅ Validation — get them to verbalize the call was helpful✅ Pivot — ask permission to share gaps or blind spots you noticed✅ Paint the Picture — describe what their life looks like with those gaps fixed✅ Invitation — "That's exactly what I help my clients achieve. Would you like to chat about what that looks like?" Resources Mentioned: 🎓 Sellfy — zero-commission digital product store 🎓 Teachers Pay Teachers (TPT) — marketplace discovery channel only 📊 AgileEngine & Branch — app monetization frameworks 🎙️ Melinda Kitto — coaching call close framework 🎙️ Aleric Heck — YouTube Alpha AI targeting strategy 🎙️ Brandon Clauser — wolf pack coaching model 🎙️ Wendy Nolan — personalized coaching vs. pre-recorded courses Submit Your Question: 🔗 Have a burning business question? Head to tuepodcast.net/askpi and Pi & Piette will build a deep dive around it. Subscribe & Share: If this episode gave you a roadmap to finally start charging for what you already know — subscribe, leave a review, and share it with the expert in your life who's still giving everything away for free. 🎙️ Business Conversations with Pi and Piette 2.0 — Real questions. AI insights. Unlimited potential.   Do you want to know what is your worst Hurdle is so you know what you want to do first to get across the start line?? Go to tuepodcast.net/quiz to get your 3 minute assessment right now and find out what your most prevalent hurdle is and how to start to overcome it! tuepodcast.net/quiz For a 15% discount on your first purchase go RYZEsuoerfoods.com use code PODNA15  Thank you for being a Skoobeliever!! If you have questions about the show or you want to be a guest please contact me at one of these social medias Twitter......... ..@djskoob2021 Facebook.........Facebook.com/skoobami Instagram.....  instagram.com/uepodcast2021 tiktok....... @djskoob2021 Email............... Uepodcast2021@gmail.com Skoob at Gettin' Basted Facebook Page Across The Start Line Facebook Community Find out what one of the four hurdles of stop is affecting you the most!! Black Friday coaching Sale now!! 65% off original price! go to stan.store/skoob to book your appointment and take advantage of this limited time offer! On Twitter @doittodaycoach doingittodaycoaching@gmailcom

    Stop Giving It Away for Free: How to Monetize Your Side Projects

  6. Aug 4

    Just Get Started: Todd Kuhn on Why Naivety Beats Overthinking, Bootstrapping Without Loans & Building a Business You Actually Love

    Did you like the episode? Send me a text and let me know!!  At 20 years old, Todd Kuhn signed a $100,000-per-year commercial lease with no loans, no outside money, and no formal business experience — just a Pilates-teaching girlfriend, a handful of community hall classes, and a gut feeling that there was a market. What came next was a business built class by class, location by location, all the way to an international product operation now expanding across the United States.  In this episode of Undiscovered Entrepreneur: Get Across the Start Line, Todd Kuhn joins Skoob for a grounded, high-energy conversation about calculated risk, market testing before committing, the difference between an operator mindset and a CEO mindset, and why the people least expected to succeed are often the ones who do — because they didn't overcomplicate it.  What You'll Learn:  How Todd went from a graduate job he hated to 40 Pilates classes a week at age 20 — in six monthsHow testing the market in community halls before signing a lease de-risked a $100,000 commitmentWhy "analysis causes paralysis" is the biggest barrier stopping entrepreneurs from startingWhy naivety and bravery often outperform overthinking and credentialsThe difference between a calculated risk and just jumpingWhy you don't need to quit your 9-to-5 until your side hustle matches or exceeds your salaryThe just-in-time learning model: learn what you need now, not what you might need somedayWhy niching down is more powerful than being a jack of all tradesHow a personal crisis became the catalyst for Todd's shift from operator to CEOThe snowflake-to-snowball-to-snowman model for building business momentumTodd's six-month goal: double income and build a values-aligned team in the US Timestamps:   [00:00:00] – Introduction & Welcome[00:01:00] – Todd's Origin Story: Graduate Job, Pilates Classes & Going All In at 20[00:03:00] – The Modern Picture of Success: Why a Degree Doesn't Equal Success Anymore[00:04:30] – YouTube University and Learning Skills Without a Classroom[00:05:00] – Learning is Useless Without Implementation[00:06:00] – Choose Your Own Adventure: Entrepreneurship as a Path, Not a Plan[00:07:00] – Imposter Syndrome and Feedback: Taking Criticism as Data, Not Attack[00:08:00] – Finding Your Tribe — Or Letting It Find You[00:09:00] – Analysis Causes Paralysis: The Mindset That Stops Most Entrepreneurs[00:10:00] – Calculated Risk vs. Blind Jumping: What the Difference Actually Looks Like[00:12:00] – The Trap of a Comfortable Job You Hate[00:13:00] – How Todd Bootstrapped: Testing the Market in Community Halls First[00:14:30] – Just-in-Time Learning: Stop Wasting Brain Calories on What You Don't Need Yet[00:15:00] – Continuous Learning Compounds: You Don't Need to Know It All to Start[00:15:30] – Niche Down or Stay Scattered: Why Focus Wins[00:16:00] – The Pitfall He's Proud Of: From Operator to CEO Mindset[00:18:00] – One Piece of Advice for New Entrepreneurs: Just Get Started[00:19:00] – Don't Quit the 9-to-5 Until the Side Hustle Matches the Salary[00:20:00] – The Snowflake-to-Snowball-to-Snowman Model for Building Momentum[00:21:00] – Todd's Six-Month Goal: Double Income & Build a Values-Aligned US Team[00:23:00] – How to Find Todd & The Core Collab USA Book Mentioned: 📚 Lean Learning — Pat Flynn (just-in-time learning vs. just-in-case learning) Connect with Todd Kuhn: 🌐 thecorecollabusa.com 🌐 sculptformer.com 📱 Socials: @TheCoreCollabUSA Subscribe & Leave a Review: If Todd's story made you rethink your what ifs — please subscribe, leave a review, and share this with an entrepreneur who's been overthinking their first step. Every review helps another undiscovered entrepreneur find this show. 🎙️ Undiscovered Entrepreneur: Get Across the Start Line — new episodes dropping regularly. Your future is waiting.   Do you want to know what is your worst Hurdle is so you know what you want to do first to get across the start line?? Go to tuepodcast.net/quiz to get your 3 minute assessment right now and find out what your most prevalent hurdle is and how to start to overcome it! tuepodcast.net/quiz For a 15% discount on your first purchase go RYZEsuoerfoods.com use code PODNA15  Thank you for being a Skoobeliever!! If you have questions about the show or you want to be a guest please contact me at one of these social medias Twitter......... ..@djskoob2021 Facebook.........Facebook.com/skoobami Instagram.....  instagram.com/uepodcast2021 tiktok....... @djskoob2021 Email............... Uepodcast2021@gmail.com Skoob at Gettin' Basted Facebook Page Across The Start Line Facebook Community Find out what one of the four hurdles of stop is affecting you the most!! Black Friday coaching Sale now!! 65% off original price! go to stan.store/skoob to book your appointment and take advantage of this limited time offer! On Twitter @doittodaycoach doingittodaycoaching@gmailcom

  7. Jul 28

    Stop Asking Strangers to Carry a Sofa: The Low-Friction Cold Outreach

    Did you like the episode? Send me a text and let me know!!   One Reddit user sent 464,000 cold emails in a single year — and figured out exactly what made people reply. A lowercase subject line with no punctuation hit a 90% open rate. A permissionless value DM on X returned a 40% response rate. And asking for a 15-minute call? Converted at a devastating 0.8%.  In this episode of Business Conversations with Pi and Piette 2.0, PI and Piette answer a listener's question from tuepodcast.net/askpi: "How do I run cold outreach on LinkedIn, X, or email without sounding like a spammer?" The answer is a complete platform-by-platform playbook built on deliverability science, human psychology, and one core truth — your ultimate competitive advantage is proving you're genuinely human.  What You'll Learn:  Why asking for a 15-minute call is the worst thing you can do in a cold emailThe offer psychology shift that jumped reply rates from 0.8% to 2.1%How to send 1,000 emails a day without triggering spam filters (the interval trick)The "ugly email rule" and why plain text outperforms beautiful HTML every timeNicholas Cole's lowercase subject line that achieved a 90% open rateThe four-step follow-up sequence — including the "right person pivot" and the A/B/C closeoutLinkedIn's five-touch warm-up sequence before you ever send a DMWhy automating LinkedIn likes and comments gets your account shadowbannedHow X (Twitter) works for reaching C-suite executives — and the golden rule about linksThe permissionless value framework and why it generates a 40% response rateWhy the future of outreach belongs to whoever can prove they're most human Timestamps:   [00:00:00] – Introduction & The Listener Question[00:01:00] – 464,000 Cold Emails: What the Biggest Outreach Test Ever Revealed[00:02:30] – Offer Psychology: Why Asking for a Meeting Is Killing Your Reply Rate[00:03:30] – Cognitive Load: The Sofa vs. the Piece of Paper[00:04:00] – From 0.8% to 2.1%: The Low-Friction Offer That Changes Everything[00:05:00] – Email Deliverability: The Invisible Bottleneck No One Talks About[00:05:30] – Sending Intervals: How to Mimic a Human to Beat the Algorithm[00:06:30] – Nicholas Cole's 90% Open Rate Subject Line (All Lowercase, No Punctuation)[00:07:00] – The Ugly Email Rule: Why Plain Text Wins Every Time[00:08:00] – The Text-to-Code Ratio: How Spam Filters Actually Read Your Email[00:08:30] – The Four-Step Follow-Up Sequence[00:09:00] – The Right Person Pivot (Step 3)[00:09:30] – The A/B/C Closeout (Step 4 — The Best Tactic in the Whole Episode)[00:10:00] – LinkedIn's Context Layer: Why DMs Here Are Different[00:10:30] – The Five-Touch Warm-Up Sequence Before You DM Anyone[00:11:30] – True Personalization vs. Mail Merge: The Trigger Event Framework[00:12:00] – Why Automating LinkedIn Engagement Gets You Shadowbanned[00:13:00] – The Three-Touch Limit on LinkedIn DMs[00:13:30] – X (Twitter): The C-Suite Goldmine With Strict Rules[00:14:00] – Account Warm-Up: Why You Can't Start DMing Immediately on X[00:14:30] – The Golden Rule: Never Put a Link in Your First X DM[00:15:00] – The Permissionless Value Framework: Reversing the Sales Debt[00:16:00] – 40% Response Rate: The Data Behind Leading With Value[00:17:00] – The Future of Outreach: AI Makes Noise, Humans Break Through[00:17:30] – Full Recap & Submit Your Question The Four-Step Follow-Up Sequence:   ✅ Day 2-3: Quick bump — "Open to a quick yes or no?"✅ Day 4-5: One specific researched detail proving you've done your homework✅ Day 7-10: Right person pivot — "Am I reaching the right person, or should I talk to someone else?"✅ Day 14: A/B/C closeout — "Reply A if not a priority, B to circle back next month, C if you're the wrong person" Submit Your Question: 🔗 Have a burning business question? Head to tuepodcast.net/askpi and Pi & Piette will build a deep dive around it. Subscribe & Share: If this episode changed how you think about outreach, subscribe, leave a review, and share it with every founder, sales professional, or freelancer still blasting generic pitches into the void. 🎙️ Business Conversations with Pi and Piette 2.0 — Real questions. AI insights. Unlimited potential.   Do you want to know what is your worst Hurdle is so you know what you want to do first to get across the start line?? Go to tuepodcast.net/quiz to get your 3 minute assessment right now and find out what your most prevalent hurdle is and how to start to overcome it! tuepodcast.net/quiz For a 15% discount on your first purchase go RYZEsuoerfoods.com use code PODNA15  Thank you for being a Skoobeliever!! If you have questions about the show or you want to be a guest please contact me at one of these social medias Twitter......... ..@djskoob2021 Facebook.........Facebook.com/skoobami Instagram.....  instagram.com/uepodcast2021 tiktok....... @djskoob2021 Email............... Uepodcast2021@gmail.com Skoob at Gettin' Basted Facebook Page Across The Start Line Facebook Community Find out what one of the four hurdles of stop is affecting you the most!! Black Friday coaching Sale now!! 65% off original price! go to stan.store/skoob to book your appointment and take advantage of this limited time offer! On Twitter @doittodaycoach doingittodaycoaching@gmailcom

    Stop Asking Strangers to Carry a Sofa: The Low-Friction Cold Outreach

  8. Jul 21

    The Skill Nobody Teaches You: Unlearning, Failing Forward & Building Brain Digits

    Did you like the episode? Send me a text and let me know!!   Episode Title: The Skill Nobody Teaches You: Unlearning, Failing Forward & Building Brain Digits  Episode Summary: What happens when an entrepreneur from Beirut, Lebanon starts a digital agency in 2011 — when Facebook was three years old and mobile websites were a novelty — and then bootstraps his way through banking crises, regional conflict, and the AI revolution to build a company now operating across the GCC? You get Jack Jendo, founder of Brain Digits, and one of the most globally minded conversations in the show's history.  In this episode of Undiscovered Entrepreneur: Get Across the Start Line, Jack unpacks why bootstrapping beats fundraising, why unlearning is a skill most entrepreneurs never develop, why failure needs to be called failure before you can learn from it, and why the future of nations depends on what humans choose to do with the most powerful tool ever created.  What You'll Learn:  Why Jack left a remote work opportunity in 2010 — before remote work existed — to start his first ventureWhat Brain Digits does: AI enablement, VR training, and emerging technology solutions across hospitals, banking, and governmentWhy bootstrapping forces you to learn every step and makes you unbreakable in a crisisWhy getting investor funding can turn a founder into an employee — and how to know when funding is actually rightThe fire analogy that explains AI's dual nature better than any tech policy paperWhy "unlearning" is the most underrated skill in entrepreneurshipWhy you need to admit failure before you can learn from it — not relabel it as "a step"Jack's 10 entrepreneurial power cards: the priority framework he shares with every founder he meetsThe concept of co-opetition — and why competing less and cooperating more grows the whole marketWhy plans are useless but planning is everything Timestamps:   [00:00:00] – Introduction & Welcome[00:01:00] – Jack's Entrepreneur Origin: Not Built for 9-to-5 in 2010[00:02:00] – Starting a Digital Agency When Facebook Was Three Years Old[00:04:00] – What Brain Digits Does: AI, VR & Emerging Technology Across the GCC[00:05:30] – From Delaware to Dubai to Saudi Arabia: How Brain Digits Scaled[00:07:00] – AI as a Tool, Not a Replacement: The Fire Analogy[00:09:00] – PhD Research: The Future of Nations with Emerging Technologies[00:10:00] – AI as a Second Brain — And the Danger of Losing Critical Thinking[00:11:30] – Human Skills in an AI World: What Schools Should Be Teaching[00:12:30] – How to Bootstrap a Business From Zero[00:14:00] – Why the Founders Who Raised Millions Wished They Had Bootstrapped[00:15:30] – The Lebanon Banking Crisis: Why Bootstrapping Made Jack Unbreakable[00:17:00] – When to Get Funding — and Why Early Funding Makes You an Employee[00:19:00] – Job Security Is a Myth: Personal Accountability in Any Economy[00:20:30] – Why Even Employees Should Start a Small Venture Now[00:22:30] – Admit Failure Before You Can Learn From It[00:23:30] – The Skill of Unlearning: Why Your Brain Needs to Delete Old Files[00:25:00] – Zone of Genius: Working Light, Fast & Free[00:27:30] – Jack's One Piece of Advice: Don't Fall in Love With Your Idea[00:29:30] – The 10 Entrepreneurial Power Cards Framework[00:31:30] – Co-opetition: Cooperating to Compete on a Larger Scale[00:33:30] – Jack's Six-Month Goal: Leading the AI Conversation in Government, Education & Health[00:35:00] – How to Find Jack & Brain Digits Connect with Jack Jendo: 💼 LinkedIn: Jack Jendo 🌐 Company: Brain Digits (braindigits.com) 🎤 TED Talk: "AI and the Rise of Digital Twins in Personal Leadership" — search on TED Submit Your Question: 🎙️ Undiscovered Entrepreneur: Get Across the Start Line — new episodes dropping regularly. Your future is waiting. Subscribe & Leave a Review: If Jack's conversation made you think differently about failure, funding, or the future of AI — please subscribe, leave a review, and share it with an entrepreneur who needs permission to unlearn something holding them back.   Do you want to know what is your worst Hurdle is so you know what you want to do first to get across the start line?? Go to tuepodcast.net/quiz to get your 3 minute assessment right now and find out what your most prevalent hurdle is and how to start to overcome it! tuepodcast.net/quiz For a 15% discount on your first purchase go RYZEsuoerfoods.com use code PODNA15  Thank you for being a Skoobeliever!! If you have questions about the show or you want to be a guest please contact me at one of these social medias Twitter......... ..@djskoob2021 Facebook.........Facebook.com/skoobami Instagram.....  instagram.com/uepodcast2021 tiktok....... @djskoob2021 Email............... Uepodcast2021@gmail.com Skoob at Gettin' Basted Facebook Page Across The Start Line Facebook Community Find out what one of the four hurdles of stop is affecting you the most!! Black Friday coaching Sale now!! 65% off original price! go to stan.store/skoob to book your appointment and take advantage of this limited time offer! On Twitter @doittodaycoach doingittodaycoaching@gmailcom

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About

Are you ready to launch your startup but feeling stuck? "Startup Success: Overcoming Entrepreneurial Obstacles" is the must-listen podcast for aspiring entrepreneurs and small business owners. Host Skoob guides you through the challenging world of startups, focusing on conquering the "4 Pillars of Stop" that hold many entrepreneurs back:1. Imposter Syndrome2. Perfectionism3. Fear of Failure4. F.E.A.R. (False Evidence Appearing Real)Each episode features real stories from startup founders and solopreneurs who've faced these common hurdles. Learn actionable strategies to boost your confidence, embrace imperfection, and turn failures into stepping stones.Key topics include:- Mindset shifts for entrepreneurial success- Practical tips for launching your business- Overcoming self-doubt and procrastination- Building resilience in the face of setbacksWhether you're dreaming of creating a tech startup, launching an e-commerce brand, or starting a freelance career, this podcast provides the motivation and tools you need to take action.Join our growing community of go-getters who live by the mantra: "I Can, I Am, I Will, And I'm Doing It Today!"Subscribe now and take your first step towards entrepreneurial success. New episodes drop weekly, packed with insights to fuel your startup journey.#StartupTips #EntrepreneurMindset #SmallBusinessSuccess #OvercomingFear #StartupMotivation

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