Startups With Stu

Stu Draper, a serial entrepreneur, knows just how exhilarating it is to launch a startup to the moon. He is a 9-time Inc. 5000 honoree before age 40 with tens of millions generated in revenue from his startups and an angel investor in 8 businesses. He's also the co-author of the bestselling textbook Digital Marketing Essentials. Stu knows just what it takes to transform an innovative idea into a thriving business. Inspired by the creators of groundbreaking ventures, Startups With Stu is an illuminating podcast that dives into the trials and triumphs of startup founders and investors who have committed their lives to reaching financial freedom through entrepreneurship. Podcast guests will be seeking advice on how to overcome the obstacles they're facing. Expect motivating stories as Stu spotlights the hard-fought victories that reveal the inner workings of entrepreneurship. By demystifying the startup process, Startups With Stu aims to equip aspiring founders with the grit and know-how

Startups With Stu is a business podcast hosted by Stuart Draper, with 71 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Stuart Draper hosts Startups With Stu, a business show with 71 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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  Episode #72

  Glowball and Life as a Youth Baseball Entrepreneur

  Aug 17, 202636 minS1

  Aaron Pridmore watched a kid rip his shirt off, climb the backstop to the song "Rodeo,"  and dance for the entire crowd at his first Banana Ball youth tournament. 75 teams had  shown up from 48 different states. Parents were cheering for both sides. Kids who were  about to quit baseball said they were coming back next season. He knew right then he'd  found his life's work. Aaron Pridmore spent 26 years at Best Buy as a district manager and territory manager,  ran the youth Banana Ball tournament operation for the Savannah Bananas, hosts The Slide  Podcast (700+ youth baseball and softball players interviewed), and is now VP at Global  Nation — bringing black light sporting events to complexes and stadiums across the country,  including the first-ever black light event at the Field of Dreams MLB stadium in September. What he covers: → 700 kids interviewed on The Slide Podcast — and what you learn when you actually let kids talk → Why more kids said they'd rather play with their friends than win a championship — every single time → The Field Reporter program: 22 kids, 11 states, retired jersey numbers, and a kid named Banana Jake who went from robotic intros to interviewing coaches at major tournaments → Getting invited to Grayson Stadium in August 2022, watching a Bananas game, and telling his wife he wanted to move to Savannah — she was already calling realtors when he got home → Writing a "future resume" as his Bananas job application: not what he'd done, but what his dream role would look like in 5 years → Running the first Banana Ball youth tournament in Cincinnati/Cleveland — 75 teams, 48 states, voted #1 youth tournament of 2025 by Newsweek (beating Cooperstown, Triple Crown, and PG) → The tournament that got hit by weather every single day in Savannah — and still beat all the competition in the Newsweek poll → A kid who said "this was going to be my last season ever, but now I'm coming back" — because there was no pressure → Stu's DoorDash driver who walked up to the front desk and asked where to apply — and is still there 6 years later → Pivoting from Bananas to Global Nation: black lights, experiential sports events, Field of Dreams → The Field of Dreams event: first-ever black light event at the new MLB stadium, home run derby, celebrity softball game, and a country music artist opening the night → Why the future resume is a "cheat code for hiring" — and what Best Buy taught him about putting people where their hearts are CONNECT WITH AARON PRIDMORE Podcast: The Slide Podcast (YouTube, Apple, Spotify — search "Slide Podcast") Business: globalnation.com CONNECT WITH STU Instagram: @stu Website: https://startupswithstu.com CHAPTERS 00:00 – Aaron intro: VP at Global Nation and host of The Slide Podcast 03:00 – What 700 youth baseball interviews taught him about what kids actually want 07:00 – Why kids choose friends over championships — every time 10:00 – The genesis of The Slide Podcast and the Field Reporter program 14:00 – Banana Jake: from robotic intro video to interviewing coaches at Prospect Wire 17:30 – The Savannah Bananas game, the wife calling realtors, and the future resume application 22:00 – The future resume explained: dream role, 5-year plan, and what Jared Orton said 26:00 – First Banana Ball youth tournament: 75 teams, 48 states, Cincinnati/Cleveland 2022 30:00 – The kid who climbed the backstop dancing to "Rodeo" 33:00 – 2025 Savannah tournament: weather chaos, damage control — then #1 in the Newsweek poll 37:00 – Pivoting to Global Nation and what black light sports events look like 40:00 – Field of Dreams: first-ever black light event, September 26, Eric Sim, Rachel Garcia, and barbecue chefs with 6M followers 44:00 – Founder takeaways: future resume, building culture people want to join, spousal support 47:00 – National Parks Baseball Resort + Global Nation crossover possibilities ⚠️ Note: Timestamps are estimated from transcript flow — swap to actual timecodes before publishing. #entrepreneur #startups #founderstory #baseball #savannnahbananas #youthsports #bananball #globalnation #slidepodcast #founderstory

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  Episode #71

  The AI Startup Solving Mental Healthcare's Biggest Hidden Problem | Episode 70

  Aug 12, 202642 minS1

  Ty Palmer built an app that plays a donkey sound when you're being an ass in an argument. It detects 48 emotions, analyzes tone of voice in real time, and even catches you being passive aggressive over text. Therapists loved it. Then they told him what they actually needed help with. Ty Palmer is the co-founder of Clary AI — an AI-powered admin platform for mental health clinics — and Donkey Chats, the couples communication app that nearly went on Shark Tank. He's bootstrapped multiple companies (including a translation company that hit $2M in its first two years), raised $1.2M for Clary at a $10M valuation in just a few days, and sat down with Stu to go deep on fundraising strategy, hiring salespeople, and why the warehouse manager outsold the Macmillan President's Club guy 4 to 1. What he covers: → Building Donkey Chats: an app that plays a donkey sound at "criticism detected: .87" — and texts you a better way to say what you just said → Getting to the last interview round on Shark Tank — then pivoting the whole company anyway → Why therapists who loved Donkey Chats kept asking for something else entirely: someone to fight the insurance companies for them → How Donkey Chats got acquired and rolled into Clary AI — and why Ty and co-founder Nathan Gunther said no to being a dev shop → Bootstrapping a translation company to $2M revenue with 10 employees as its first employee — then leaving → A VR company in 2019, sold before owning equipment — how he convinced his entrepreneur-averse wife one small bet at a time → Closing a $500K raise in "a few days" through angels only, at a $10M valuation → Stu's breakdown on valuation math: why raising at 5M vs. 10M changes when investors will let you exit → The warehouse manager from Target who outsold a Macmillan President's Club rep 4 to 1 — and what that means for hiring salespeople → Why Stu says never hire one sales rep — always hire two (if you can't tell if it's you or them, you learn nothing) → The "dating game" hiring test: give a candidate a script, a phone, and a directory — and see if they book appointments before they're even hired → Peak Capital (Silicon Slopes VC) telling Stu his TAM was too small — and why he now thinks that was the best thing that ever happened to him CONNECT WITH STU Instagram: @stu Website: https://startupswithstu.com CHAPTERS 00:00 – Stu's update: National Parks Baseball Resort sold out all 2027 spots in 7 weeks 02:30 – Ty introduces Clary AI: AI admin for mental health clinics 06:00 – Donkey Chats origin: catching tone-of-voice problems in real-time couples arguments 10:00 – How the app works: 48 emotions, text message analysis, "criticism detected: .87" 13:30 – Getting to Shark Tank's last interview round — then pivoting anyway 17:00 – Why therapists loved Donkey Chats but needed insurance billing help more 20:00 – Corbin Church, the roll-up, and how Donkey Chats became Clary 24:00 – Ty's entrepreneur origin story: catering company, VR rentals, translation company 28:30 – Bootstrapping vs. raising: closing $1.2M at $10M valuation in days 32:00 – Stu on valuation math: the goalpost problem every founder ignores 37:00 – Angels vs. VCs — Stu's experience with Silicon Slopes and why seed rounds worked better 41:00 – Hiring sales: warehouse manager outsells President's Club rep 4 to 1 45:00 – The "dating game" hiring test and why you should always hire two reps, never one 48:30 – CRMs, follow-up culture, and why Stu's team had "F.U." on the whiteboard ⚠️ Note: Timestamps are estimated from transcript flow — swap to actual timecodes before publishing. #entrepreneur #startups #founderstory #mentalhealth #aitools #saas #fundraising #startuplife #donkeychats #claryai

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  Episode #70

  From Cop to $17.6M Entrepreneur | Sam DiMeo’s Startup Journey | Episode 69

  May 27, 202634 minS1

  Sam DeMaio taught himself construction from a $34.95 Home Depot book. He was working full-time as a correctional officer, then a police officer — and running a side hustle the entire time. Nobody knew. He didn't need them to. Sam is the founder of Showcase Remodels out of New Jersey, a remodeling company he scaled to $17.6 million in gross revenue. He also owns 48 rental properties, has done 17+ house flips using a repeatable buy-for-30-sell-for-125 model, and just launched his own product line — Signature Reflections — after a national brand told him no. He joined Stu at a Startups with Stu retreat and covered the whole road: blue-collar upbringing, Army service, a decade in law enforcement, a divorce that lit a fire, and a business philosophy built on one simple rule: get it, give it. What he covers: → Joining the Army at 17 as a cavalry scout — with a 13-second life expectancy on the battlefield → Getting charged $100/week rent by his dad on his 18th birthday, then going out and buying a duplex at 19 → Running a construction side hustle, a flooring business, and rental properties — all while working full-time as a police officer → Learning construction from scratch using a $34.95 Home Depot book (no YouTube, no ChatGPT) → Leaving the police force with $20,000 to his name and $90K/year walking out the door → Buying a hoarder house in Glendora, NJ for $30,000 — poop stains, broken tools, the whole thing — and flipping it for $125K → Running his flip formula for two years straight: buy for $70K, put in $30K, sell for $170K — 17 houses → Building a portfolio of 48 rental properties that covers every bill he has, including the beach house → Scaling Showcase Remodels to $17.6 million in annual gross revenue → Buying a hotel in North Wildwood for $1 million, putting $700K into it in 12 weeks, converting it to condos, and selling for $3.2 million → Getting rejected by a national bathroom brand — then writing back to tell them they made the biggest mistake of their life, and launching his own competing product line → His employee who made $350,000 in his first year — and the people who used to cheer for him that are now hating → Giving a woman's entire kitchen to a woman who adopted 8 kids with special needs, which turned into a chain of other contractors donating materials for free 🔗 CONNECT WITH STU Instagram: @stu Website: https://startupswithstu.com 📌 CHAPTERS 00:00 – Introduction: Who is Sam DeMaio? 02:15 – Blue-collar roots: Chuck in a truck, Catholic school, Army at 17 05:30 – The $100 birthday bill and the duplex at 19 08:45 – Correctional officer by day, contractor by night 12:00 – The $34.95 Home Depot book that started it all 15:20 – Building the side hustle: flooring, flips, rentals 18:40 – Why he stayed in the police force for 10 years before going all in 21:30 – The divorce, the $20K, and the leap 24:15 – The hoarder house flip: $30K in, $125K out 27:00 – The flip formula: 17 houses, same model 30:10 – Scaling Showcase Remodels to $17.6M 33:45 – The hotel flip: $1M in, $3.2M out in 12 weeks 37:00 – Getting rejected by a national brand and starting Signature Reflections 40:20 – Culture over spreadsheets — and the employee making $350K 43:00 – The woman who adopted 8 kids and the kitchen that became a community 45:30 – What "taking your startup to the moon" means to Sam #entrepreneur #startups #founderstory #realestateinvesting #remodeling #contractor #sidehustle #bluecollarbusiness #buildingwealth #smallbusiness

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  Episode #70

  From Cop to $17.6M Entrepreneur | Sam DiMeo’s Startup Journey | Episode 69

  May 27, 202634 minS1

  <p> <p >Sam DeMaio taught himself construction from a $34.95 Home Depot book. He was working full-time as a correctional officer, then a police officer — and running a side hustle the entire time. Nobody knew. He didn't need them to.</p><br /><p >Sam is the founder of Showcase Remodels out of New Jersey, a remodeling company he scaled to $17.6 million in gross revenue. He also owns 48 rental properties, has done 17+ house flips using a repeatable buy-for-30-sell-for-125 model, and just launched his own product line — Signature Reflections — after a national brand told him no. He joined Stu at a Startups with S...

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  Episode #69

  How a Twenty-Something Entrepreneur Landed 35% Equity | Episode 68

  May 25, 202654 minS1

  <p> <p >When her business partner asked how he should pay her, AnnaMarie Davis said she didn't want </p><p >an hourly rate. She wanted equity. She was a college student who had been working in his studio </p><p >for months, had never been paid a dollar, and didn't entirely know what equity meant. She ended </p><p >up with 35%.</p><br /><p >AnnaMarie Davis is a partner at Audio and Recording, a commercial recording studio in Salt Lake </p><p >City. She got there through competitive dance, door-to-door solar sales, two shipping containers </p><p >she bought and retur...

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