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 73 episodes on record and a Required Pod Score of 80.

Stuart Draper hosts Startups With Stu, a business show with 73 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 #74

  From Frat House to Wing Empire: The Matt Friedman Story

  Sep 23, 202640 minS1

  Matt Friedman had a commercial kitchen available every night after 6:30pm — the fraternity  house kitchen. He installed a phone line, printed some flyers, went to Sam's Club for wings  and one type of Coke, and started delivering buffalo wings to college students at the University  of Florida. That was 1993. Twelve banks said no when he tried to get a loan. His parents  said yes to $50,000. Wing Zone was born. Matt Friedman is the founder of Wing Zone — a brand he built from a $500 frat house  experiment to an Inc. 500 franchise company with locations across the US and internationally  — and current CEO of Epic Wings, a 40-year-old, 35-location fresh wing brand in Southern  California. He's also the author of the Amazon bestseller "From Frat House to Franchising,"  available for $0.99 on Kindle or as a 14-hour audio book Matt recorded himself. What he covers: → A $500 startup in a frat house kitchen: one phone line, Sam's Club ingredients, guerrilla flyer marketing on campus → Walking into 12 banks with a business plan and getting declined by every single one of them → His parents lending him $50,000 in 1994 — a real loan, due back whether the business succeeded or failed, contingent on him graduating first → Capitalizing on a failed restaurant: finding a closed spot near campus with existing hood, plumbing, and electrical — then lipsticking the pig → Going from 1 to 7 company-owned stores in 5 years — all Florida and Georgia college markets → Making the Inc. 500 as a bootstrapped wings chain with zero outside investors → The friend-turned-partner Adam: 50/50 for 27 years, five arguments total, completely different skill sets — and still best friends → First franchisees were his own store managers who wanted to own their Wing Zone location → Why franchising didn't show a dollar of profit for the first two and a half years — and why that's normal → The rhino mascot and why thick skin is required: when franchisees succeed they credit themselves, when they fail they point at you → Why he joined Epic Wings as CEO: no freezers, everything fresh, 35 locations in 40 years, zero national ambitions → The most underrated ingredient in restaurant success: consistency, not quality → Writing "From Frat House to Franchising" with a ghostwriter over 25 weeks — then recording the 14-hour audio version himself CONNECT WITH MATT FRIEDMAN Book: "From Frat House to Franchising" — $0.99 on Kindle, 14-hr audio on Audible Epic Wings: epicwings.com CONNECT WITH STU Instagram: @stu Website: https://startupswithstu.com CHAPTERS 00:00 – Intro: Wing Zone founder, Epic Wings CEO, and author 02:30 – Writing "From Frat House to Franchising": ghostwriter, 25 chapters, 14 hours in the studio 07:00 – Why the audio book is $0.99 — and why he recorded it himself 10:00 – The frat house kitchen insight: commercial kitchen, empty after 6:30pm 13:30 – $500 startup: one phone line, Sam's Club run, flyers on campus 17:00 – Twelve bank rejections and the $50,000 parental loan (with graduation required first) 21:00 – Finding a failed restaurant near campus and making it the first Wing Zone storefront 24:30 – The name "Winging It," the trademark fight, and the rebrand to Wing Zone 27:00 – Adam: the 50/50 partner, different skill sets, five arguments in 27 years 31:00 – One to seven stores in five years — taking the best manager to each new city 34:30 – Making the Inc. 500 as a bootstrapped chain 37:00 – Why franchising is a completely different business than running restaurants 41:00 – Splitting the company: Matt runs franchising, Adam runs operations — both own 50/50 of each 44:30 – Two and a half years before franchise profits — and what the recurring revenue looks like after 48:00 – The rhino mascot and what it means to be a franchisor 51:00 – Selling Wing Zone in 2021 and pivoting to consulting 54:00 – Epic Wings: 40 years old, 35 locations, no freezers, fresh everything 57:00 – Quality vs. consistency — and why consistency wins every time ⚠️ Note: Timestamps are estimated from transcript flow — swap to actual timecodes before publishing. #entrepreneur #startups #founderstory #wingzone #epicwings #franchising #foodbusiness #restaurantbusiness #fomfrathousetofranching #bootstrapped

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  Episode #73

  The Buyer’s Perspective: How to Build a Business Worth Acquiring

  Sep 21, 202647 minS1

  A dentist Stu knew from church retired after decades of practice and just closed the doors.  Didn't sell it. Didn't know he could. Just locked up and walked away from what could have been  a real exit. Jason Morris heard the story and said it almost happened to a company he knows  every week. Rich Jarvis is the founder of Epic Capital Funds — $830 million under management, $3.4 billion  in the pipeline — and Jason Morris is his partner at Impact Equity Partners, a 14-year portfolio  CEO turned business acquirer. Together they sat down with Stu to talk through how private equity  actually works, what they look for when buying founder-built businesses, and what most  entrepreneurs get wrong about building for an exit. What they cover: → A Lake Tahoe hotel project that took nine years just to get through entitlement — the first hotel approved in Tahoe City in over 60 years → The "SUCCEED" model: Structure, Underwriting, Core teams, Capital stack, Exit strategy, Execution, Due diligence — how they vet every deal → What a portfolio CEO actually does: 14 years of managing companies inside PE portfolios, hitting metrics, getting to exit → Buying a hypoallergenic adhesive manufacturer in Oregon (biggest industry: gel nails) — and the bolt-on DTC brand merger that followed → Three non-emergency transportation companies under contract, plus an auto repair company to service their fleet → The dentist who closed his doors on 40 years of work without selling — and why Stu nearly cried → "Second bite of the apple": how Rich and Jason structure deals so founders can share in the upside again when they sell → Reviewing 3,000 companies in one year — and how discipline in the "buy box" gets you from chaos to traction → Why focusing on revenue instead of profit is the most common alignment failure in growing companies → Rich's weekly non-negotiable: "clarity breaks" — out of the office, asking two questions, revisiting the why → The EOS/Traction framework and why most of their portfolio companies attribute scalability directly to it → Why raising capital is about relationships first, transactions second — and how Rich built $830M AUM through RIA relationships, not direct investor pitches → How Stu raised money for Stu Kent: not through one big ask, but decades of being a trusted person CONNECT WITH RICH JARVIS Epic Capital Funds: epiccapitalfunds.com CONNECT WITH JASON MORRIS Impact Equity Partners: impactequitypartners.com CONNECT WITH STU Instagram: @stu Website: https://startupswithstu.com CHAPTERS 00:00 – Intro: two guests, two companies, one whiteboard week in Boise 03:30 – Rich Jarvis: first rental in 1998, lost everything 2008-2011, restarted in 2019 07:00 – Epic Capital Funds: $830M AUM, $3.4B pipeline, what those numbers actually mean 10:30 – The Lake Tahoe hotel: 9 years to entitlement, first approval in 60 years 13:00 – Jason Morris: 14 years as a portfolio CEO — what that job actually is 17:00 – The whiteboard week in Boise that launched Impact Equity Partners 20:30 – What they buy: cash-flowing, 10+ year businesses with lifestyle-owner upside 24:00 – The dentist story: closed the doors after 40 years without selling a thing 27:30 – Second bite of the apple: how deal structure gives founders another payday 31:00 – First acquisition: Oregon hypoallergenic adhesive manufacturer (gel nails → DTC) 35:00 – HVAC company, three NEMT companies, and an auto repair bolt-on 38:30 – 3,000 companies reviewed, a disciplined buy box, and saying no to shiny objects 42:00 – Revenue vs. profit: the alignment failure that kills growing companies 45:00 – Rich's clarity breaks and why he considers them the most important hour of his week 48:30 – EOS/Traction, scorecards, rocks, and one source of truth 52:00 – RIA relationships: how $830M AUM came from fewer, deeper relationships — not a big list 55:30 – How to raise capital: relationships over transactions, value over asks 58:00 – Measuring life from the rocking chair: 5,000 lives impacted vs. Standing Room Only ⚠️ Note: Timestamps are estimated from transcript flow — swap to actual timecodes before publishing. #entrepreneur #startups #founderstory #privateequity #realestate #businessacquisition #smallbusiness #exitstrategy #investing #epiccapitalfunds

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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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