Startups With Stu

Stuart Draper
  • 5.0 (8)
  • Entrepreneurship
  • Weekly

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 to transform visionary concepts into startup success. Startups With Stu is produced using PodUp podcasting software.

  1. 1d ago

    Forget Billion-Dollar Startups: This VC Backs Profitable Founders

    A founder sat down to pitch a $75,000 investment and said there was just one little problem: a developer in Ukraine was holding her code base hostage. She told the investors before the wire cleared. She bought the shares back for $225,000, and a month later they were worth $2.5 million. Erica Wassinger is a venture capitalist at Proven Ventures, a $10 million Nebraska-only seed fund that invests through "debt equity": the founder buys the shares back out of a slice of monthly revenue, capped at 3x. She went from a journalism degree at Kansas State to Wharton, Berkeley, and the Silicon Prairie, and she thinks the billion-or-bust model is the wrong bet for most businesses. Stu and Erica get into how she decides who gets her attention, why she cuts every forecast in half, and how Stu's $25,000 friends-and-family check turned into $967,000. What she covers: → A $75,000 investment where the founder confessed before the wire that a Ukraine-based dev consultant was holding her code base hostage → Buying back equity at 3x ($225K) out of roughly 5% of monthly gross revenue, then watching the shares become worth $2.5M in a multi-million dollar round a month later → Why Erica hates pitch decks and won't let founders use one on a call: send her the demo you give your customers instead → "My love language is a CRM": how her website contact form feeds her CRM, and why it beats a warm intro → Her Founders Field Guide to being capital ready: your customer, their problem, and how $1 of capital creates $3 in revenue → Why Proven Ventures cuts every founder's forecast by 50-60% → Why a founder who pays themselves nothing is a red flag, and the math on what a buyer subtracts when you pay yourself $100K but replacing you costs $300K → Why profitability and EBITDA, once "dirty words" in Silicon Valley, are what acquirers use to set the price now → A fund that wants to be "obsolete" on your cap table, and says it's beating the top-quartile fund on cash returned (per Carta's Q2 analysis) → Stu's $25,000 friends-and-family investment in 2013 that came back as a $967,000 check in 2021 → A bad executive hire, burned cash, and why "figure it out" founders are the ones she never loses sleep over → The pretend cowgirl pitch: Silver Spur Ranch in Idaho, Dax and Bodie, and a possible Startups with Stu retreat with horses 🔗 CONNECT WITH STU Instagram: @stu Website: https://startupswithstu.com 📌 CHAPTERS 00:00 – Intro: Silicon Prairie, Lincoln, and summers in the Sandhills 03:00 – Journalism degree to venture capital: Kansas State, Wharton, and Berkeley 06:00 – Why founders must pay themselves and what buyers do with that math 10:00 – Proven Ventures: a $10M Nebraska fund and the last $1M of Fund One 12:00 – Profitability and EBITDA: the "dirty words" that are saving portfolios 14:00 – Why Erica does podcasts and the shows founders learn from 17:00 – How to get her attention: the personalized LinkedIn invite and the website form 19:00 – Why she hates pitch decks and wants your customer demo instead 23:00 – "My love language is a CRM" and the Founders Field Guide to being capital ready 27:00 – The Ukraine dev consultant holding a code base hostage 30:00 – Debt equity explained: $75K in, $225K back, 5% of gross revenue 34:00 – $225K of shares worth $2.5M, and a fund that wants to be obsolete 37:00 – Cutting every forecast 50-60% and capping returns at 3x 40:00 – Stu's $25K friends-and-family check that became $967K 42:00 – Founders who figure it out, follow-on checks, and a bad executive hire 45:00 – Silver Spur Ranch, cowgirl grit, and why you can't bet the farm every time 48:00 – Closing: think about your capital stack differently ⚠️ Note: Timestamps are estimated from transcript flow. Swap to actual timecodes before publishing. #entrepreneur #startups #founderstory #venturecapital #fundraising #nebraska #siliconprairie #seedfund #revenuebasedfinancing #provenventures

  2. 6d ago

    He Returned $1 Million to Investors — A Founder’s Unusual Story

    Tim Klich raised $1 million from pickleball players before he'd built a single court. Then he gave every dollar back, because the project ran so late he felt bad keeping it. Tim spent 35 years as a commercial banker, the last 20 lending to tech startups, and never once got in trouble with a regulator. At 60 he started the Austin Pickle Ranch, and the city of Austin spent the next three years teaching him why bankers make poor real estate developers. He's 64 now, plays in every 7 a.m. game, and bought into a pro team as one of the eight original founders of Major League Pickleball. What he covers: → Telling a guy at a 2019 Wimbledon finals watch party that pickleball is "for losers who can't play tennis," then playing it at his house that night → Raising 1Minfoundingmemberdeposits(5,000 for five years of free play) with a college intern answering inbound emails while checks showed up in the mail → Structuring those deposits as a loan, not a security, so he never had to register with the Texas State Securities Commission → Giving all $1M back to members when the delays dragged on → A city that tried to declare a river through the middle of his land, three years of fighting it, and the epiphany that renting beats owning → His first location in a downtown parking garage: it killed it there, then noise complaints and zoning shut it down → A 70-location pickleball chain filing Chapter 11 the same week, and the overbuild Tim predicted back in 2023 → Why venues paying 70-80% of revenue in rent are nearly impossible to buy (a typical SaaS company pays 10-15%) → Why every pickleball court is the same size, and why community is the only real differentiator → Being willing to be "the bad guy" when a player's DUPR rating isn't high enough for the top game → Turning down a Merrill Lynch move to San Francisco in the mid-90s, then driving his parents nonstop from Columbus to Austin in a minivan after his dad's stroke → The one thing he'd do differently: raise outside money earlier 🔗 CONNECT WITH STU Instagram: @stu Website: https://startupswithstu.com 📌 CHAPTERS 00:00 – Intro: from 35 years of commercial banking to a pickle ranch 02:30 – Why a banker who backed tech startups became a founder at 60 05:00 – Lending against raw land and the Wimbledon night that changed the plan 09:00 – The downtown parking garage location: killed it, then got shut down 12:00 – A river nobody could find on a map and the "rent, don't own" epiphany 16:00 – $1M in founding member deposits, then giving all of it back 20:00 – The $5,000 loan structure: five years of free play, no securities filing 23:30 – Predicting the pickleball overbuild in 2023 and the 70-location bankruptcy 26:30 – Every day at the club: 7 a.m. games and midnight closes 29:00 – Four generations on one block and the San Francisco job he turned down 32:30 – Branding, a brand book, and why Yellowstone helped 35:00 – Why buying a pickleball venue rarely pencils out (rent at 70-80% of revenue) 38:00 – Community as the moat: open play, ratings, and being the bad guy 42:00 – Stu on dialing in the customer experience 44:00 – What Tim would tell himself before starting: raise outside money earlier ⚠️ Note: Timestamps are estimated from transcript flow. Swap to actual timecodes before publishing. #entrepreneur #startups #founderstory #pickleball #austintx #secondact #sportsbusiness #smallbusiness #austinpickleranch

  3. Oct 7

    A Solopreneur's Perspective on Entrepreneurship - Tim Shea's story

    Tim Shea's data analytics company has clients that include the NBA, UFC, Princess Cruise Lines,  and Reddit. He started the company solo, scaled to five employees during Covid, then went back  to solo — by choice. He calls VC "another form of poverty." He calls his current setup "crushing it." Tim Shea is the founder of Latticework, a retail and DTC data analytics company focused on  50–100M brands. With 25 years in data analytics, he's helped major brands decode the  difference between the customer who buys once on Black Friday and the customer who buys  every single month for two years straight — and figure out exactly how much they can afford to  spend to acquire more of the second type. What he covers: → Why your data is stuck in 20–30 different platforms the moment you start growing — and why reassembling it every Monday is killing your team → The "Moneyball for retail" framework: finding the counterintuitive, high-leverage metrics hidden inside your company's history → True North metrics: the 1–2 numbers every early-stage founder should optimize everything around — and when to switch them → LTV broken three ways: Black Friday buyers who don't come back for 12 months vs. January buyers who purchase every month for two years → Athletic Greens' CMO on payback period: average customer stays for two years at $99/month — do the math on what you can spend to acquire them → Why paying $1,000 to acquire a customer is not crazy — and why a finance-background CEO freaks out while a marketing-background CEO gets it → The AI + data future: pointing Claude at Snowflake, skipping the BI dashboards, and building custom scenario tools that show "$50K opportunity if you bend this curve by 1%" → Why Tableau and Looker are becoming obsolete — and what replaces them → Five companies in, solo again: why he delivers the work himself instead of building a team of junior folks → The "scarlet letter" of entrepreneurship: why big companies won't hire ex-founders → Why VC is "a whole other form of poverty" — and why debt, crushing it, and buying other businesses are all legitimate alternatives → When to call Tim: when your CFO is spending 4–8 hours a week jamming spreadsheets together every Monday morning 🔗 CONNECT WITH STU Instagram: @stu Website: https://startupswithstu.com 📌 CHAPTERS 00:00 – Intro and how "Latticework" got its name 03:00 – What Tim does: retail and DTC data analytics for $50–100M brands 07:00 – The universal startup data problem: stuck in 30 platforms, reassembled every Monday 11:00 – Moneyball for retail: finding the counterintuitive high-leverage metrics 15:00 – True North metrics: what to optimize for at each stage of growth 19:00 – LTV 101: why you don't have one LTV ratio — you have three types of customers 24:00 – Athletic Greens' two-year average retention and what that means for acquisition spend 28:00 – AI + data: pointing Claude at Snowflake, killing the BI dashboard era 32:00 – Tableau gets a hug, then gets replaced: the new world of custom AI dashboards 36:00 – Growing up in Boston, moving to LA, discovering entrepreneurship the hard way 40:00 – Five companies in, back to solo — and why he's delivering the work himself 44:00 – The "scarlet letter" of being an ex-founder in a corporate job interview 47:00 – Lifestyle business vs. VC: why crushing it is a legitimate option 51:00 – Stu's PE exit story and the "bootstrapped" label he didn't expect 55:00 – National Parks Baseball Resort and how past skills stack into new ventures 58:00 – Now you have a friend in the data analytics business ⚠️ Note: Timestamps are estimated from transcript flow — swap to actual timecodes before publishing. #entrepreneur #startups #founderstory #dataanalytics #retail #dtcbrands #moneyball #ltv #ecommerce #latticework

  4. Oct 5

    He Lost Everything — Then Built a Global Education Company

    Fadi Alshalabi had 48 hours to leave Syria. He left behind his wife, his six-year-old daughter,  and his sick father. One week later, his wife told him she was pregnant with their second child.  He was starting over in Berlin with nothing but a research contract and a dream about education. Fadi Alshalabi is the founder of Niuversity — an online education platform that has taught  80,000 students across 40 countries, achieved a 92% course completion rate (the global average  is 8-12%), and ran a 100-student pilot with Google that graduated every single student. He grew  up in Damascus, was expelled from the US after 9/11, fled Syria in 2013 when Assad's regime  tried to arrest him, nearly got deported from Germany in 2020 after Covid wiped out his funding,  and is now a German citizen teaching digital skills to Arabic-speaking learners worldwide. What he covers: → Growing up in Damascus — the oldest inhabited capital in the world — and watching the Arab Spring turn into war → Being expelled from the US in 72 hours after 9/11 as a Middle Eastern student → Working as Head of International Affairs at Damascus University: managing 45 staff, running EU-funded projects, refusing to appear on TV to defend Assad's narrative → Getting 48 hours notice to flee Syria in 2013 — leaving his wife, six-year-old daughter, and pregnant wife behind → Seven and a half months separated from his family while they tried to get a German visa from the Beirut embassy → Being forced into entrepreneurship — selling his house in Syria and wiring money out illegally to fund his residence permit in Germany → The idea for Niuversity: seeing his own former students standing in food lines as refugees in Berlin in December 2015 → Why the global course completion rate is 8-12% — and how Niuversity hit 92% with live teaching → Winning second place at a Berlin startup competition — and a Google rep saying "from my side, you deserved first" → Asking Google for one favor: a video call with the director of Google Skills in Dubai, not an email → Running a 100-student pilot with Google that hit 100% completion — then signing a 2.5-year contract → Getting a letter in July 2020 saying Germany was revoking his residence after 7 years of taxes, employees, and integrated daughters → Three days in the hospital after a near heart attack — doctors asking him to write his will → Fighting the German government, winning the case, and eventually becoming a German citizen → Niuversity today: 5 staff, pivot underway, teaching professors how to teach online and integrate AI → The new mission: bringing EU-accredited digital credentials to Syrian universities after the fall of Assad 🔗 CONNECT WITH STU Instagram: @stu Website: https://startupswithstu.com 📌 CHAPTERS 00:00 – Intro: growing up in Damascus, the oldest inhabited capital in the world 03:30 – The Arab Spring hits Syria — and Fadi refuses to defend Assad on international TV 07:00 – 48 hours to leave: how the Damascus University president saved his life 11:00 – Seven and a half months separated from his family, wife pregnant with their second daughter 15:00 – The first expulsion: post-9/11, 72 hours to leave the US 18:00 – Forced into entrepreneurship: selling his house in Syria, wiring money to Germany illegally 22:00 – The idea for Niuversity: seeing his own former students in a Berlin food line in December 2015 26:30 – Building the Arabic Coursera — and why completion rate was the obsession 30:00 – 92% completion vs. the global 8-12% average — and nobody believing it 33:30 – The Google rep at a Berlin startup competition: "You deserved first place" 36:00 – Asking for a video call, not an email — and the 100-student pilot that hit 100% completion 40:00 – The 2.5-year Google contract and working with Meta 43:30 – Covid kills the funding model — 12 employees, thousands of students, one email saying it's over 47:00 – July 2020: Germany revokes residence after 7 years — near heart attack, three days in hospital 51:00 – Fighting back, winning the legal case, becoming German citizens 54:30 – Niuversity today: EU digital credentials, teaching AI to professors, mission in Syria 58:00 – What keeps him up at night — and Stu's advice on pre-selling to donors ⚠️ Note: Timestamps are estimated from transcript flow — swap to actual timecodes before publishing. #entrepreneur #startups #founderstory #edtech #elearning #refugee #syria #germany #niuversity #onlineeducation

  5. Sep 23

    From Frat House to Wing Empire: The Matt Friedman Story

    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

  6. Sep 21

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

    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

  7. Aug 17

    Glowball and Life as a Youth Baseball Entrepreneur

    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

  8. Aug 12

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

    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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8 Ratings

About

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 to transform visionary concepts into startup success. Startups With Stu is produced using PodUp podcasting software.

Information

  • Creator
    Stuart Draper
  • Years Active
    2024 - 2026
  • Episodes
    77
  • Rating
    Explicit
  • Copyright
    Copyright © 2026 Stuart Draper. All rights reserved.
  • Show Website
    Startups With Stu

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