Startups With Stu
Stuart Draper
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...
Episodes
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 STUInstagram: @stuWebsite: https://startupswithstu.com📌 CHAPTERS00:00 – Intro and how "Latticework" got its name03:00 – What Tim does: retail and DTC data analytics for $50–100M brands07:00 – The universal startup data problem: stuck in 30 platforms, reassembled every Monday11:00 – Moneyball for retail: finding the counterintuitive high-leverage metrics15:00 – True North metrics: what to optimize for at each stage of growth19:00 – LTV 101: why you don't have one LTV ratio — you have three types of customers24:00 – Athletic Greens' two-year average retention and what that means for acquisition spend28:00 – AI + data: pointing Claude at Snowflake, killing the BI dashboard era32:00 – Tableau gets a hug, then gets replaced: the new world of custom AI dashboards36:00 – Growing up in Boston, moving to LA, discovering entrepreneurship the hard way40:00 – Five companies in, back to solo — and why he's delivering the work himself44:00 – The "scarlet letter" of being an ex-founder in a corporate job interview47:00 – Lifestyle business vs. VC: why crushing it is a legitimate option51:00 – Stu's PE exit story and the "bootstrapped" label he didn't expect55:00 – National Parks Baseball Resort and how past skills stack into new ventures58:00 – 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
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 STUInstagram: @stuWebsite: https://startupswithstu.com📌 CHAPTERS00:00 – Intro: growing up in Damascus, the oldest inhabited capital in the world03:30 – The Arab Spring hits Syria — and Fadi refuses to defend Assad on international TV07:00 – 48 hours to leave: how the Damascus University president saved his life11:00 – Seven and a half months separated from his family, wife pregnant with their second daughter15:00 – The first expulsion: post-9/11, 72 hours to leave the US18:00 – Forced into entrepreneurship: selling his house in Syria, wiring money to Germany illegally22:00 – The idea for Niuversity: seeing his own former students in a Berlin food line in December 201526:30 – Building the Arabic Coursera — and why completion rate was the obsession30:00 – 92% completion vs. the global 8-12% average — and nobody believing it33:30 – 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% completion40:00 – The 2.5-year Google contract and working with Meta43:30 – Covid kills the funding model — 12 employees, thousands of students, one email saying it's over47:00 – July 2020: Germany revokes residence after 7 years — near heart attack, three days in hospital51:00 – Fighting back, winning the legal case, becoming German citizens54:30 – Niuversity today: EU digital credentials, teaching AI to professors, mission in Syria58:00 – 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
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 FRIEDMANBook: "From Frat House to Franchising" — $0.99 on Kindle, 14-hr audio on AudibleEpic Wings: epicwings.com🔗 CONNECT WITH STUInstagram: @stuWebsite: https://startupswithstu.com📌 CHAPTERS00:00 – Intro: Wing Zone founder, Epic Wings CEO, and author02:30 – Writing "From Frat House to Franchising": ghostwriter, 25 chapters, 14 hours in the studio07:00 – Why the audio book is $0.99 — and why he recorded it himself10:00 – The frat house kitchen insight: commercial kitchen, empty after 6:30pm13:30 – $500 startup: one phone line, Sam's Club run, flyers on campus17:00 – 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 storefront24:30 – The name "Winging It," the trademark fight, and the rebrand to Wing Zone27:00 – Adam: the 50/50 partner, different skill sets, five arguments in 27 years31:00 – One to seven stores in five years — taking the best manager to each new city34:30 – Making the Inc. 500 as a bootstrapped chain37:00 – Why franchising is a completely different business than running restaurants41:00 – Splitting the company: Matt runs franchising, Adam runs operations — both own 50/50 of each44:30 – Two and a half years before franchise profits — and what the recurring revenue looks like after48:00 – The rhino mascot and what it means to be a franchisor51:00 – Selling Wing Zone in 2021 and pivoting to consulting54:00 – Epic Wings: 40 years old, 35 locations, no freezers, fresh everything57:00 – 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
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 JARVISEpic Capital Funds: epiccapitalfunds.com🔗 CONNECT WITH JASON MORRISImpact Equity Partners: impactequitypartners.com🔗 CONNECT WITH STUInstagram: @stuWebsite: https://startupswithstu.com📌 CHAPTERS00:00 – Intro: two guests, two companies, one whiteboard week in Boise03:30 – Rich Jarvis: first rental in 1998, lost everything 2008-2011, restarted in 201907:00 – Epic Capital Funds: $830M AUM, $3.4B pipeline, what those numbers actually mean10:30 – The Lake Tahoe hotel: 9 years to entitlement, first approval in 60 years13:00 – Jason Morris: 14 years as a portfolio CEO — what that job actually is17:00 – The whiteboard week in Boise that launched Impact Equity Partners20:30 – What they buy: cash-flowing, 10+ year businesses with lifestyle-owner upside24:00 – The dentist story: closed the doors after 40 years without selling a thing27:30 – Second bite of the apple: how deal structure gives founders another payday31:00 – First acquisition: Oregon hypoallergenic adhesive manufacturer (gel nails → DTC)35:00 – HVAC company, three NEMT companies, and an auto repair bolt-on38:30 – 3,000 companies reviewed, a disciplined buy box, and saying no to shiny objects42:00 – Revenue vs. profit: the alignment failure that kills growing companies45:00 – Rich's clarity breaks and why he considers them the most important hour of his week48:30 – EOS/Traction, scorecards, rocks, and one source of truth52:00 – RIA relationships: how $830M AUM came from fewer, deeper relationships — not a big list55:30 – How to raise capital: relationships over transactions, value over asks58:00 – 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
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 PRIDMOREPodcast: The Slide Podcast (YouTube, Apple, Spotify — search "Slide Podcast")Business: globalnation.com🔗 CONNECT WITH STUInstagram: @stuWebsite: https://startupswithstu.com📌 CHAPTERS00:00 – Aaron intro: VP at Global Nation and host of The Slide Podcast03:00 – What 700 youth baseball interviews taught him about what kids actually want07:00 – Why kids choose friends over championships — every time10:00 – The genesis of The Slide Podcast and the Field Reporter program14:00 – Banana Jake: from robotic intro video to interviewing coaches at Prospect Wire17:30 – The Savannah Bananas game, the wife calling realtors, and the future resume application22:00 – The future resume explained: dream role, 5-year plan, and what Jared Orton said26:00 – First Banana Ball youth tournament: 75 teams, 48 states, Cincinnati/Cleveland 202230:00 – The kid who climbed the backstop dancing to "Rodeo"33:00 – 2025 Savannah tournament: weather chaos, damage control — then #1 in the Newsweek poll37:00 – Pivoting to Global Nation and what black light sports events look like40:00 – Field of Dreams: first-ever black light event, September 26, Eric Sim, Rachel Garcia, and barbecue chefs with 6M followers44:00 – Founder takeaways: future resume, building culture people want to join, spousal support47:00 – 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
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 STUInstagram: @stuWebsite: https://startupswithstu.com📌 CHAPTERS00:00 – Stu's update: National Parks Baseball Resort sold out all 2027 spots in 7 weeks02:30 – Ty introduces Clary AI: AI admin for mental health clinics06:00 – Donkey Chats origin: catching tone-of-voice problems in real-time couples arguments10:00 – How the app works: 48 emotions, text message analysis, "criticism detected: .87"13:30 – Getting to Shark Tank's last interview round — then pivoting anyway17:00 – Why therapists loved Donkey Chats but needed insurance billing help more20:00 – Corbin Church, the roll-up, and how Donkey Chats became Clary24:00 – Ty's entrepreneur origin story: catering company, VR rentals, translation company28:30 – Bootstrapping vs. raising: closing $1.2M at $10M valuation in days32:00 – Stu on valuation math: the goalpost problem every founder ignores37:00 – Angels vs. VCs — Stu's experience with Silicon Slopes and why seed rounds worked better41:00 – Hiring sales: warehouse manager outsells President's Club rep 4 to 145:00 – The "dating game" hiring test and why you should always hire two reps, never one48:30 – 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
From Cop to $17.6M Entrepreneur | Sam DiMeo’s Startup Journey | Episode 69
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 STUInstagram: @stuWebsite: https://startupswithstu.com📌 CHAPTERS00:00 – Introduction: Who is Sam DeMaio?02:15 – Blue-collar roots: Chuck in a truck, Catholic school, Army at 1705:30 – The $100 birthday bill and the duplex at 1908:45 – Correctional officer by day, contractor by night12:00 – The $34.95 Home Depot book that started it all15:20 – Building the side hustle: flooring, flips, rentals18:40 – Why he stayed in the police force for 10 years before going all in21:30 – The divorce, the $20K, and the leap24:15 – The hoarder house flip: $30K in, $125K out27:00 – The flip formula: 17 houses, same model30:10 – Scaling Showcase Remodels to $17.6M33:45 – The hotel flip: $1M in, $3.2M out in 12 weeks37:00 – Getting rejected by a national brand and starting Signature Reflections40:20 – Culture over spreadsheets — and the employee making $350K43:00 – The woman who adopted 8 kids and the kitchen that became a community45:30 – What "taking your startup to the moon" means to Sam#entrepreneur #startups #founderstory #realestateinvesting #remodeling #contractor #sidehustle #bluecollarbusiness #buildingwealth #smallbusiness
How a Twenty-Something Entrepreneur Landed 35% Equity | Episode 68
When her business partner asked how he should pay her, AnnaMarie Davis said she didn't want an hourly rate. She wanted equity. She was a college student who had been working in his studio for months, had never been paid a dollar, and didn't entirely know what equity meant. She ended up with 35%.AnnaMarie Davis is a partner at Audio and Recording, a commercial recording studio in Salt Lake City. She got there through competitive dance, door-to-door solar sales, two shipping containers she bought and returned, an investor dinner she walked into not knowing what an investor was, and a 2.5-hour phone call with a stranger named Eric. She is in her 20s.What she covers:→ Age 12: dad lost his job, dance was too expensive — so she walked into the studio owner's office and negotiated her own free tuition by teaching tap and ballet and cleaning every studio after hours, without telling her parents→ Knocking doors in Utah selling solar at 18, offering Girl Scout cookies as part of her pitch (she actually bought them)→ Buying two shipping containers for $6,000 to build a DIY recording studio — then discovering that soundproofing and equipment would cost a fortune→ Getting the prompting: "Don't bury your talents and don't let your friends bury theirs" — and realizing the music world was full of audio engineers who couldn't get jobs and artists who couldn't afford studios→ A little girl at a dance recital, a dad who ran investor dinners, and the chain reaction that changed everything→ Walking into Tyler Jennings' investor dinner, saying "I have no idea how to do this" — and getting put in 10 group chats and invited to four more lunches→ A 2.5-hour first phone call with her future business partner Eric, not even remembering he owned a studio→ Working in Eric's studio for three months for free before he offered to pay her — and saying no, she wanted equity instead→ Earning equity benchmarks tied to revenue milestones, working her way to 35% ownership while still dancing at BYU→ Vibe coding a custom booking system because no good scheduling software exists for music studios→ Monthly jam sessions — poets, musicians, audiobook narrators, a random violinist, and one unforgettable rendition of Don't Stop Believin' — as the free event that drove all their word-of-mouth→ Big artists signing the wall behind a mirror (so the signatures exist but can't be posted anywhere) — and the time she had a full conversation with a major artist and didn't know who he was until after🔗 CONNECT WITH STUInstagram: @stuWebsite: https://startupswithstu.com📌 CHAPTERS00:00 – Intro and growing up with four older brothers02:30 – Age 12: dad loses his job, dance is too expensive, AnnaMarie negotiates her own tuition06:00 – Dad stops being a lawyer and becomes an entrepreneur — what watching that taught her09:30 – High school deal: get your associates, parents pay for everything; graduate, you're on your own12:00 – Door-to-door solar sales at 18 with Girl Scout cookies as backup15:30 – BYU, competitive dance, declaring entrepreneurship as a major on a whim19:00 – The prompting: don't bury your talents, don't let your friends bury theirs22:30 – Two shipping containers, $6,000, and the moment she realized she had no idea what she was doing26:00 – The little girl at the recital, Tyler Jennings, and the investor dinner30:00 – Walking in with nothing but a dream — and getting 10 group chats and four follow-up lunches34:00 – The 2.5-hour first call with Eric Low, her future business partner38:00 – Three months working for free, then: "Do you want me to pay you?" — "No, I want equity."42:00 – Earning her way to 35% through revenue benchmarks45:00 – Vibe coding a custom booking system and building word-of-mouth through jam sessions49:00 – Big artists, hidden signatures, and the celebrity conversation she didn't know she was having52:30 – Advice for aspiring college-age entrepreneurs#entrepreneur #startups #founderstory #youngentrepreneur #recordingstudio #musicbusiness #womeninbusiness #saltlakecity #collegeentrepreneur #audioengineering
Mom of 5 Builds Million-Dollar Apparel Brands | Episode 67
Chynna Hansen was taping boxes for a cross-state move when she turned to her husband and said she was starting a business. He asked if they could maybe just get moved first. She said she didn't think they could wait.Chynna is the founder and CEO of Vast Apparel and Little Mama Shirt Shop — both seven-figure businesses built in Idaho Falls. She started with a $400 seed fund from a unicorn birthday invitation that went viral on Etsy, bootstrapped Little Mama Shirt Shop into a seven-figure DTC brand, and then built Vast Apparel from scratch when the DTC market shifted. Vast is now up 300% year over year.What she covers:→ A unicorn birthday party invitation that went viral on Etsy — selling thousands of copies, one name-swap at a time, staying up nights changing the birthday girl's name by hand (long before AI)→ Starting Little Mama Shirt Shop with $400, a Facebook Live to five friends and her grandma, and selling out that first night→ Meeting her screen printer in his "little dark basement" — long beard, covered in tattoos, rode a Harley — with total confidence from a small-town girl who didn't know what she didn't know→ Building a team of 30 moms who close at 2pm every day so everyone can pick up their kids from school→ Working only Tuesdays and Wednesdays — and getting a full week's work done in two days→ Taking a deliberate dip in Little Mama revenue to simplify the launch schedule when the team started burning out→ A spiritual impression so strong she stopped the business mid-planning: "Give it away" — two weeks before a major campaign launch→ Starting The Heart of It Foundation and giving back hundreds of thousands of dollars through Little Mama Shirt Shop over the years→ $30,000–$35,000 raised in 24 hours for Texas flood relief through a single launch→ Building Vast Apparel when equipment was sitting idle — and watching it hit 300% year-over-year growth→ The $270 naming contest for Vast (Phil Knight paid $30 for the Nike swoosh — she did the math and matched it in today's dollars)→ Why she named her flagship backpack after her dad and what that legacy-building means to her🔗 CONNECT WITH STUInstagram: @stuWebsite: https://startupswithstu.com📌 CHAPTERS00:00 – Intro and where the name Chynna comes from02:30 – Growing up in Salmon, Idaho (3,000 people, two stoplights, 86 kids in her graduating class)05:00 – The $200 gap that started everything: staying home with her first son08:00 – The viral unicorn birthday invitation and saving $400 to start Little Mama Shirt Shop12:00 – Taping boxes in Utah, telling her husband she was starting a business right now15:30 – Selling out on Facebook Live to five friends and her grandma18:00 – Meeting the screen printer in his dark basement (and why her husband was nervous)21:00 – Running the business in the cracks of motherhood: late nights, early mornings, never trading motherhood for ambition25:00 – Building a team of 30 moms — closed at 2pm, no Saturdays28:30 – Working only Tuesdays and Wednesdays and still growing32:00 – Little Mama hits seven figures, then the DTC market shifts36:00 – Vast Apparel is born out of idle equipment and necessity — now up 300% year over year40:00 – The Phil Knight naming contest and the moment "Vast" gave everyone chills43:30 – The spiritual impression three weeks before launch: "Give it away"47:00 – The Heart of It Foundation, $35K in 24 hours for Texas floods, and giving back locally51:00 – The charter plane and the rocket ship: Little Mama and Vast, side by side#entrepreneur #startups #founderstory #womeninbusiness #mompreneur #ecommerce #vastapparel #idahofalls #bootstrapped #ladyboss
Building a National Outdoor Brand from Scratch | Episode 66
Scott Jensen liquidated his 401k, maxed out a HELOC, and spent six years burning through his corporate savings to build a backpacking company. He's in Costco, Scheels, Walmart, Macy's, and Amazon. And he's still almost out of money.Scott Jensen is the founder of Near Zero — a company on a mission to demystify backpacking with a complete, bundled, patented kit that gets you trail-ready in 30 minutes. He spent 15 years in corporate supply chain at Honeywell, Tyco Electronics, and Carlisle, learned Mandarin Chinese, lived in China as an expat with five kids, and used every bit of it to build something no one else could easily copy.What he covers:→ Starting a snow cone business at age 8, making $20/hour with a hand-cranked machine — then saving $500 to upgrade to electric→ Becoming a balloon artist at 15 after a classmate said he was making $30/hour on weekends→ Working for free for an import-export mentor who told him: "Go work for corporate first, then come back to me"→ Honeywell sponsoring him through Thunderbird — the #1 international business school in the world→ Living in China with five kids as an expat from 2018 to 2020, then evacuating when Covid hit→ Quitting his director-level job in 2021 with zero retail experience and all-in on Near Zero→ The Dean backpack: named after his dad, 11 prototypes, an 80-page tech pack, three years of development before the first sale→ Getting into Scheels, Walmart, Macy's, Amazon, Boy Scouts of America, and Costco — all while burning personal savings→ Raising $100K through a SAFE on WeFunder, with a $100 minimum investment for future equity→ Why his Chinese supply chain background creates barriers to entry nobody can easily copy→ The cash crunch every founder hits — and what Josh James (Omniture, sold to Adobe) says about how to get through it→ Learning Mandarin on a mission to Taiwan after expecting to go Spanish-speaking — and how that single surprise assignment changed his entire career🔗 CONNECT WITH STUInstagram: @stuWebsite: https://startupswithstu.com📌 CHAPTERS00:00 – What "Near Zero" means and Scott's moon landing03:00 – 15 years in corporate: Honeywell, Tyco Electronics, Carlisle, and living in China07:00 – Snow cones at 8, balloon art at 15, palm trees, vending machines, wedding videos11:00 – The decision to quit: depleting the 401k and maxing the HELOC14:00 – What Near Zero is: 100+ SKUs, the Dean backpack, and the all-in-one bundle18:30 – How he built the Dean: 11 prototypes, 80-page tech pack, three years of development23:00 – Getting into Scheels, Costco, Walmart, and Amazon — and the cash flow problem that followed27:00 – Raising on WeFunder: $100 minimum, SAFE structure, investor perks including a backpacking trip31:00 – The barriers to entry: patents, supply chain complexity, and why big brands won't copy this easily35:00 – Stu's advice: focus on sales, build the right team, treat investor money as sacred39:00 – Taiwan mission, Mandarin Chinese, and how a devastating assignment became a career launchpad43:00 – What's next for Near Zero#entrepreneur #startups #founderstory #backpacking #outdoors #ecommerce #bootstrapped #nearzero #supplychain #smallbusiness
25 Years in Fitness, 2 Big Exits, Zero Investors | Episode 65
At 21, Todd Kuhn signed a $120,000-a-year lease. Everyone thought he was mad. Twenty years and two exits later, he's never taken a dollar from a bank or an investor.Todd Kuhn is an Australian founder who built and sold two fitness businesses — the first a multi-location gym group, the second a 20-studio boutique Pilates chain acquired by an ASX-listed company. Now he's building Core Lab, bringing premium Pilates equipment to the US market, and doing it the same way he's always done it: bootstrap first, scale smart, exit with a plan.What he covers:→ Signing a $120,000/year lease at age 21 — and everyone telling him he was mad→ Running Pilates mat classes in 40 scout halls and town halls across the city (400 students per term)→ Amassing $150,000 cash in six months before ever opening a physical studio→ A 5-day mastermind in Hawaii that got him off 95% of his own classes and changed the whole trajectory→ Going from 1 studio to 10 in three years, then 20 just before Covid hit→ Selling to an ASX-listed company — and watching every one of his locations convert to Club Pilates→ His grandfather building the original Pilates equipment by hand in a garage under his house→ Flying to China 4-5 times a year, walking into factories with no translator, using sign language to get the product right→ Why he's never taken a bank loan or outside investment across two full business cycles→ The "minimize startup costs, maximize profitability" principle he applies to every studio he opens→ Why delegation is the one thing he'd tell his younger self to do faster→ Launching a new Dallas studio with Australian franchisees who followed him to the US🔗 CONNECT WITH STUInstagram: @stuWebsite: https://startupswithstu.com📌 CHAPTERS00:00 – Todd's background: rugby recruit to business founder03:30 – Leaving corporate after six months and pivoting to fitness06:00 – 40 locations in scout halls and $150K cash before opening a studio09:00 – Signing the $120K lease at age 21: "just have a go"12:00 – Exiting Pure Health Clubs in 2012 and starting over smaller15:30 – The Hawaii mastermind that unlocked the scale-up19:00 – 10 locations in 3 years, 20 before Covid, then the exit23:00 – Being acquired by an ASX company and watching the brand become Club Pilates26:30 – Building Core Lab: equipment, method, training academy30:00 – Why he's never taken outside money — and what he thinks about it now34:00 – His grandfather, a friend with a welder, and the origin of Core Lab's equipment38:00 – Flying to China 4-5x a year with no translator to source parts41:30 – Advice for aspiring founders: persistence, vision, and giving away hats45:00 – The Dallas launch and what's next#entrepreneur #startups #founderstory #fitness #pilates #bootstrapped #businessexit #australianfounder #corelabusa #smallbusiness
Why High Performers Still Feel Empty | Episode 64
Stu wired his whole career chasing recognition. He didn't know it until a live coaching session on camera revealed the exact lie running underneath everything.Dallin Harmon left a high-paying angel investing role to coach founders full-time — and in this episode, he does it live with Stu. What came up wasn't what either of them expected.What he covers:→ Discovering the subconscious belief: "The only way to be valued is to be seen and recognized by the world's standards"→ The day Stu's big payday hit his bank account — and his family already had Saturday plans→ Calling CFO Mike Andrus and screaming at the top of their lungs on the phone (ten years of work, finally done)→ Why reframing thoughts almost never creates permanent change — and what actually does→ Two truths that changed Dallin's life: every belief that drives you to suffering is a lie, and your best moments are who you really are→ Stu's daughter's four-year health battle, spending 40 days in the hospital, and the moment he snapped at the mold specialist→ Three emotional memories used to rewire a belief live on air — including Stu's dad hugging him after a wrestling match→ Sending a son off on a mission at the airport and why that moment hit harder than any business win→ The Chad Willard quote that landed differently after the coaching: "I don't inhale the compliments, so I don't spiral over the criticism"→ Why Dallin says he learned more about himself in 3 years of coaching than in the previous 3 decades combined→ The difference between "useful" and "powerful" — and why Stu's drive got him far but couldn't take him further🔗 CONNECT WITH STUInstagram: @stuWebsite: https://startupswithstu.com📌 CHAPTERS00:00 – How Dallin went from building companies to coaching them02:30 – The cost of building with stress, shame, and overwhelm for a decade05:00 – "You can have it all — you just have to reclaim your time from suffering"08:00 – The mold specialist story: Stu's worst self, caught live13:00 – Two truths that change how you see every hard moment18:30 – Uncovering the lie Stu didn't know he believed24:00 – Shocking the brain out of a false belief28:30 – Three emotional memories used to rewire the belief live36:00 – The payday, the normal Saturday, and the wake-up call42:00 – Chad Willard quote + the shift in how Stu will operate now#entrepreneur #startups #founderstory #mindset #coaching #selfawareness #founders #personaldevelopment #leadership #businesspodcast
Building More Than a Startup: Becoming Who You’re Meant to Be | Episode 63
She showed up to a city she'd never been to, knew exactly one person, talked 30 restaurants into joining her event, went on live TV twice, and then coded a backup solution by herself two hours before the launch party when her developer bailed. The app didn't grow the way she wanted. She didn't quit.Lee Balcomb is the founder of Healthy Anywhere — a hyper-curated restaurant app that functions like having a holistic nutritionist, food writer, and data analyst on call, helping health-conscious travelers find meals that actually match their standards. She's been building it full-time since 2018, and the original idea? That came to her in January 2003.What she covers:→ Growing up in Montgomery, Alabama on Little Caesars pizza, two-liter Cokes, and Krispy Kreme crullers — and being bloated and foggy as a kid because of it→ Moving to California in her 20s and discovering vegetables that come from the ground, not cans — and never feeling better→ Getting stranded in a barren Philadelphia apartment at 1am with nothing to eat — the exact moment in January 2003 that sparked the entire business→ Locking herself in the house before a trip to Spain just to build a 78-restaurant spreadsheet with 14 columns covering wild fish, organic veggies, leafy greens, and healthy fats→ Quitting a job she loved in 2018 after private equity bought the company and killed the culture — and needing six months just to decompress before she could build→ Reading 60 books in a year, getting a holistic nutrition certification, and completing sustainable food systems studies at UC Berkeley to earn the "street cred" to build the scoring system→ Nearly blowing up the entire pipeline by bringing on an AI contractor who quietly wrecked the data — and not discovering how bad it was until weeks later→ Organizing the CEO's Healthy Week in Colorado Springs — a city she'd never visited — getting 30 restaurants to participate and over $2,000 in prizes, only to have her developer bail four days before launch→ Coding her own QR/PHP solution solo until two hours before the launch party just so the event could run→ Going on live TV twice, getting customers to drive down from Denver, Boulder, and Fort Collins — and hearing from a woman who attended five restaurants in one weekend: "Who do you need? Because imagine what you could do with support."→ The advice from an 84-year-old Silicon Valley angel investor: "No matter what happens, this is already been a phenomenal success."→ Why she's bootstrapping and hasn't raised money — and why she believes she has to earn the right to keep building first→ "It's not what I'm building. Ultimately, it's who I am becoming."🔗 CONNECT WITH STUInstagram: @stuWebsite: https://startupswithstu.com📌 CHAPTERS00:00 – Intro + How Lee and Stu connected at Laguna Beach[~02:00] – What is the Healthy Anywhere app?[~05:00] – The origin story: Philadelphia airport, 1am, nothing to eat (January 2003)[~09:00] – The 78-restaurant spreadsheet with 14 columns (a weekend in D.C.)[~12:00] – Why she left her job in 2018 and what happened next[~16:00] – 60 books, a nutrition certification, and UC Berkeley[~20:00] – The AI contractor who quietly wrecked the pipeline[~24:00] – CEO's Healthy Week: 30 restaurants, Colorado Springs, developer bails 4 days out[~31:00] – Coding the launch solo, two hours before the party[~36:00] – Why she's bootstrapping and what she needs before she'd ever raise[~41:00] – The 84-year-old angel investor's advice that she still reflects on[~45:00] – "It's not what I'm building. It's who I'm becoming."[~48:00] – Family, Jason, and what spousal support actually looks like#entrepreneur #startups #founderstory #healthyfood #bootstrapped #womenfounder #appbuilder #healthyanywhere #startuplife #solofounder
He Built a Self-Cleaning Toilet Seat… And Raised $1M | Episode 62
Rob Polecki was an elected official in Idaho when he took his 4-year-old son into a dirty airport bathroom and couldn't find a single hands-free way to clean the toilet seat. Everything else in the restroom was touchless. Just not the part that mattered most.That moment in 2015 turned into Washi — a self-sanitizing commercial toilet seat Rob has been building, bootstrapping, and fighting for ever since. He cashed out $100K+ from his government 401K, raised over $1M from angels one check at a time, made it to the final round of Shark Tank, spent a year in licensing talks with Georgia Pacific (only to get ghosted), and is now launching a home version via Kickstarter in May 2026.What he covers:→ Taking his 4-year-old to a dirty Salt Lake City airport bathroom — and walking out with a business idea→ Carrying a toilet bowl through the Venetian Hotel in Las Vegas to audition for Shark Tank→ Making it to the final round of Shark Tank before getting cut — and why he calls it the best thing that happened to him→ Cashing out over $100K from his government 401K to go all-in on the company→ Spending an entire year in engineering discussions with Georgia Pacific (the largest restroom company in the US), only to be told "go launch it yourself and we'll buy it later"→ Raising $500K in a friends-and-family round from Pocatello, Idaho, then going angel by angel for $50K–$200K at a time→ Firing his internal sales team and switching to distributors after years of slow B2B cycles→ Landing Delta Sky Clubs, major gas station chains in the Midwest, and convention centers in the South→ Why airports in Wyoming took 9 months from first meeting to closed deal→ Launching the home version of Washi with a Kickstarter in May 2026 — and why B2C changes everything→ What James Dyson's story meant to him every time he almost quit→ Why having other people's money in the company means there's no Plan B🔗 CONNECT WITH STUInstagram: @stuWebsite: https://startupswithstu.com#entrepreneur #startups #founderstory #sharktank #bootstrapped #hardwareStartup #invention #washi #toiletseat #startupswithstu
They Almost Went Broke… Then Built a $31M Business | Episode 61
The franchising consultant they paid $100,000 to get their paperwork done turned out to be embezzlingmoney and having an inappropriate relationship with a staff member. The company collapsed. Eight monthsof work, gone. The other four companies they'd been working with also went under. Adam Newman'sresponse was to keep going — and eventually sell for $31 million.Adam Newman is the co-founder of Monkey Bar Storage (originally Gorgeous Garage), a garageorganization company his father Jared started in a two-car garage in Boise with a shelf he welded himself.Adam built it into a 120-location dealer network, hit $31M in revenue the year they sold, and walked awaywith an eight-figure exit. He sat down with Stu at a live Startups with Stu retreat near YellowstoneNational Park to break down exactly how they did it.What he covers:→ Jared Newman building the first shelf system to organize his own garage — then a neighbor's backyard party of 20+ employees accidentally becoming their first marketing campaign→ Year 1 revenue of $46,000 with $48,000 in costs — and how a year's worth of severance pay kept the lights on→ Doubling revenue three years in a row without a single dollar of advertising, purely on word of mouth→ Taking out a $25,000 SBA loan (with two old pickup trucks and two laptops as their only assets) to start a Salt Lake City dealership — and doing $160,000 in their first partial year→ Getting robbed by a franchise consultant who embezzled $100,000 of their money, then being saved by the president of the national franchising association — who flew out privately to Rexburg to meet with them→ How a single sales rep named Reg Allen took them from 8 locations to 47 locations in two years→ Taking over every dealer's website, marketing, photography, and content — and why that made dealers never want to leave→ Designing their own overhead rack system by putting Jared "in a box" with tight parameters — and beating competitors on dimensional shipping weight to cut costs→ Growing the Amazon and third-party marketplace channel from 1 unit sold to a $1 million annual channel in two years→ Adding a cabinet line after one dealer proved it doubled ticket prices from $2–4K to $9–10K→ Revenue milestones: $5M (2010/11), $9M (2012), $16M (2015/16), $24M (2019), $31M the year they sold→ The secret sauce: what Jared did at every install that made customers remember him — not the product — and how it became a systemized revenue driver across 120 locations🔗 CONNECT WITH STUInstagram: @stuWebsite: https://startupswithstu.com📌 CHAPTERS00:00 – Intro: Adam Newman and how he met Stu 21 years ago04:00 – Jared Newman: farm kid, welder, and the shelf he built to organize his own garage09:00 – Year 1: $46K revenue, $48K costs, and the backyard party that changed everything14:00 – Three years of doubling with zero advertising — and the numbers that convinced Adam to go all in19:00 – The $25K SBA loan, the Salt Lake dealership, and $160K in the first partial year24:00 – Expanding to four locations, the 2007 housing crash, and the franchising question29:00 – The $100K franchise consultant who embezzled everything — and the national president who flew to Rexburg to help35:00 – Building the dealer model: from loose and chaotic to 120 locations with full marketing control40:00 – Reg Allen: the sales rep who sold 20 dealerships in year one, then 47 in year two44:00 – Designing their own overhead rack by boxing Jared in with impossible constraints49:00 – The $1 million Amazon channel, the cabinet line, and doubling average ticket price54:00 – Revenue timeline: $5M to $31M and the eight-figure exit58:00 – The secret sauce: what Jared did at every install that no competitor thought to copy#entrepreneur #startups #founderstory #exitstrategy #dealermodel #garagebusiness #smallbusiness #ecommerce #franchising #8figureexit
She Did WHAT to Get a CEO’s Attention?! | Episode 60
She sent an unscripted, badly lit, walking-outside selfie video to the CEO of Caterpillar — one of thelargest companies on earth. Her client laughed at her. Told her it was unprofessional. She did it anyway.Seven minutes later, Paul emailed back. That email is now framed on her wall.Bianca McDownriver is a Texas-based entrepreneur, freestyle rapper, and founder of Box Voice, an11-year marketing agency that works with everyone from stormwater compliance companies to Mr. Beast'steam. She sat down with Stu at a live Startups with Stu retreat in Highland Park, Idaho — after spendingseven minutes the night before cooling off in a lake with 16 inches of ice underneath her.What she covers:→ Teaching piano in high school because she refused to ask her parents for money — ever→ Upselling car wash customers from a $39 wash to a $200 detail as a teenager, and realizing she was born to sell→ Starting a supplement brand called Driven at BYU Idaho, burning through her savings, and watching her business partner spend their shared cash on an engagement ring→ Throwing freestyle rap battle parties at BYU Idaho — hundreds of students paying $10 to watch college kids rap — and scaling it to block parties with thousands of attendees and stage acts from Utah→ Making real money not from door fees but from apartment complex sponsorships — charging them for a table in front of students every semester→ Running two businesses and five internships simultaneously while still getting a degree→ Why she built Box Voice by saying yes to every industry — ERP, CRM, termite control, security monitoring, publishing — and why the "find your niche" advice is wrong for her→ The unscripted $49/month video tool (Hippo Video) that out-converts every polished campaign she's ever run→ Why she wears a nearly $4,000 purse to first client meetings — and the Google ex-employee who studied body language and said yes because of it→ The body language moves that close deals: palms out, open stance, and why crossing your arms silently kills your pitch→ T-boning a drunk driver at 65 mph at age 18 in Farmington, New Mexico — and the three thoughts that flashed through her mind before she knew she'd survive→ Why she can say right now, without hesitation, that if she died tomorrow she would have zero regrets🔗 CONNECT WITH STUInstagram: @stuWebsite: https://startupswithstu.com #entrepreneur #startups #founderstory #womenfounder #marketingagency #salestips #bodylangage #BYUIdaho #livewithurgency #smallbusiness
How Raleigh Williams Sold His Business for $26M | Episode 59
How Raleigh Williams Sold His Business for $26M | Episode 59He had a panic attack on the gym floor 30 days into his dream law firm job — and called his wife thinking he was having a heart attack. Turns out his body already knew what his brain hadn't caught up to yet: he was in the wrong life.Raleigh Williams went from panic attacks at a prestigious law firm to building Williams Entertainment Group — escape rooms, trampoline parks, and entertainment concepts — then selling it all across nine transactions for $26 million. Now he runs Exit OS (a business brokerage for SMB founders) and Fierce Health and Fierce Longevity (telehealth and peptide clinics). He sat down with Stu live at the Startups with Stu retreat in Saint George, Utah to break it all down.What he covers:→ Having a panic attack 30 days into a prestigious law firm job — hoping it was a heart attack because a panic attack felt worse → Trying and failing at faceless Instagram accounts, tax liens, and becoming a real estate agent before finding the right idea → Reading a MarketWatch article about escape rooms and doing the back-of-napkin math that same night→ Paying a European escape room $5,000 to license their puzzle sequences as a starting point → Running a Harry Potter-themed room ("Horcrux Hysteria") in violation of Warner Bros. IP for four years before getting a cease and desist → Discovering that revenue correlated directly with number of rooms — not marketing spend → Selling the entire business across nine transactions for $26 million (including real estate) when he realized he'd mentally checked out → The four levers that determine your business's sale multiple: growth rate, operations, clean accounting, and defensibility → Why founders should know their exit multiple from Day 1 — and what it means if your take-home salary times four is your retirement number → GLP-1 peptides (Retatrutide), BPC-157 "Wolverine stacks," and how peptides helped him get in better shape at 36 than ever before → His wife's two bouts of cancer — and how navigating the medical system pushed him into building Fierce Longevity → "The cave you fear to enter holds the treasure that you seek" — the quote he carries with him everywhere🔗 CONNECT WITH RALEIGH WILLIAMS Instagram: @raleigh_williams 🔗 CONNECT WITH STUInstagram: @stu Website: https://startupswithstu.com#entrepreneur #startups #founderstory #escaperoombusiness #businessexit #exitstrategy #peptides #glp1 #smallbusiness #startupswithstu
From Couch Surfing to $7M Startup - Story of Anya Chang | Episode 58
She didn't know what entrepreneurship was two years before starting her company.She grew up in Taiwan, her dad worked in a factory, and when she landed her first U.S. job offer she went home and Googled "contractor" — and genuinely thought they wanted her to be a plumber.Anya Cheng spent 15 years at Meta, eBay, Target, and McDonald's before launching Taelor AI, a subscription service that uses AI to pick and rent clothes for busy men. She raised $2.3M at a $7M valuation, and her investors now include the YouTube founder, Google Gradient Capital, and Morgan Stanley's managing director.What she covers:→ Starting a media club in a Taiwanese high school that banned new clubs — by reading the full handbook and collecting 500+ signatures→ Arriving in the U.S. barely speaking English and getting rejected from every campus recruiter during the 2008 recession→ Couch-surfing New York City for two months to network her way into a job — with no money and no contacts→ Calling a Taiwanese magazine to get free conference access as a "media representative" so she could afford to attend→ Googling "contractor" after landing her first U.S. job offer and thinking they wanted her to be a plumber→ Launching Taelor AI with a $10 Shopify site that had nothing on it except an email signup box→ Ignoring their first customer for a month because she thought he was a scammer — then shipping him clothes from a department store sale→ Raising $1M from Northwestern and Chicago Booth alumni WhatsApp groups before ever talking to a single VC→ Getting a warm intro to Bowling Capital through a founder she forgot she was supposed to be networking with→ Winning a startup competition hosted by Northwestern — held at a University of Chicago event — and using the rivalry to get press coverage→ That press coverage landed her on a local ABC morning show, which she used to convince a fashion trade publication to run her story, which got her first brand partner→ Growing from 1 brand partner to 150+ fashion brands (Mizzen+Main, Johnston Murphy, Bonobos, Cuts, Rhone) without buying inventory upfront→ Selling data back to fashion brands to help them predict demand and cut the $30 billion in unsold clothing that goes to landfill each year→ Why she rallied "minority investors" after learning only 1.8% of VC funding goes to female founders — and how that strategy built her entire cap table🔗 CONNECT WITH ANYA CHENGWebsite: https://taelor.style🔗 CONNECT WITH STUInstagram: @stuWebsite: https://startupswithstu.com#entrepreneur #startups #founderstory #womenfounder #fashiontech #AIstartup #venturecapital #immigrantfounder #startupfunding #siliconvalley
Business Lessons from a Ninja Warrior Champion Turned Businessman | Wally Roskelly | Episode 57
The guy sold longboards, princess dresses, tungsten rings, and hoverboards out of the same warehouse. Then he built the largest ninja warrior gym in the world.Wally Roskelly has been on American Ninja Warrior three times, took first place Masters gold at the World Ninja Games, and has started more businesses than most people have had jobs. He sat down with Stu at a live retreat recording to talk about all of it — the wins, the near-million-dollar hoverboard disaster, and why he says he'll never sell his gym even at breakeven. What he covers:→ Quitting an $11/hour insurance gig to start his own agency (same product, completely different feeling)→ How he spotted a supply-and-demand gap in longboards and turned a bedroom full of 100 boards into a fulfillment operation with 250 drop shippers→ Wiring $7,000 to a stranger in China for princess dresses. They sold out in two days.→ Ordering $450K worth of hoverboards, watching the second container get stopped at the California port, and making about $4,000 total on the deal→ Getting on Ninja Warrior (90,000 applicants, 600 spots) and building a backyard course that turned into a real gym→ 4,000 people showing up on opening day of a gym that didn't have a single ad running→ His obsessive market research process — including months of sitting in competitors' parking lots counting foot traffic→ Why community and belonging drive retention better than any marketing you could run→ 1,003 pull-ups in 5 hours at age 45 (nearly double David Goggins' pace)→ The adoption story he rarely tells publiclyCONNECT WITH WALLYInstagram: @wallyroskellyCONNECT WITH STUInstagram: @stuWebsite: https://startupswithstu.com
From Idaho Farm Kid to Billion-Dollar Exits | James Clarke | Episode 56
James Clarke is the kind of entrepreneur you don't hear about on podcasts — not because he hasn't built at scale, but because he's not chasing the spotlight. Growing up in Rexburg, Idaho, James watched his uncle and aunt build Diet Center, a diet franchise business that became the predecessor to Jenny Craig and Nutrisystem. But what inspired him most wasn't the helicopter in the backyard — it was the generosity. New lockers for the high school. Donations with a US senator present. That shaped his definition of success before he ever started a company.James went on to build ClearLink, a performance marketing company he scaled to eight figures of profitability before selling. He used the proceeds to immediately invest in two companies: Contour, an action camera company that went head-to-head with GoPro, and PetIQ, which he chaired from a $1 million investment to a $2 billion exit. He's now running Clark Capital Partners, a family office focused on growth equity — buying businesses doing $1-5M EBITDA and helping them scale.In this episode, recorded live at the Startup Solstice retreat in Island Park, Idaho, James gets into the real lessons: why he came back to ClearLink years later and found a completely different company, how AI and Google's algorithm wiped out their EBITDA recovery mid-stride, why he keeps a check in his pocket for the right pitch meeting, and the hard truth that your worst problems in business always have a first and last name.He also draws a sharp line between business players and business creators — people who love having lunches and talking versus people who execute. And he challenges founders on mentor relationships: listen selectively, because even billion-dollar advice can steer you wrong if you follow it blindly instead of incorporating it into your own strategy.Topics: Clark Capital Partners, ClearLink, PetIQ IPO, Contour vs GoPro, growth equity investing, family office, startup retreats, founder mentorship, Idaho entrepreneurs, hiring and firing, Extra Space Storage, business exits
From Selling Potatoes to Scaling VIdAngel | Dallin Harmon | Episode 55
Dallin Harmon grew up broke in Idaho selling potatoes door-to-door with his siblings. His brothers went on to build Harmon Brothers, Angel Studios, and Tuttle Twins. Dallin co-founded Cove Security, helped scale VidAngel under an employee-ownership model that tripled the business, and now coaches founders through Scale Me. In this episode, he shares the brutally honest moment he realized he'd never own what he built, why he walked away, and then coaches Stu live — uncovering a subconscious lie about recognition that most founders carry without knowing it. Dallin Harmon is the Harmon brother you haven't heard of — and his story might be the most relatable one for founders. While his brothers Neal, Jeffrey, Daniel, and Jordan were building Angel Studios (The Chosen, Sound of Freedom), Harmon Brothers (Squatty Potty, Purple), and Tuttle Twins, Dallin was carving his own path from an Idaho childhood where his family earned less than $10,000 a year.In this episode, Dallin shares how selling potatoes door-to-door as a kid built the resilience that carried him through co-founding Cove Security and scaling it during Covid from 9,000 to nearly 40,000 accounts in a single year. He opens up about the moment he and his brother Jordan realized they'd never have meaningful equity in the company they helped build — and why that honest conversation changed everything.Dallin then breaks down the employee-ownership model he helped implement at VidAngel, where the CEO kept only 25% and gave 75% back to employees. That model tripled revenue and earned VidAngel Best Place to Work in Utah three years running.The second half of the episode flips the format entirely. Dallin uses his coaching skills to walk Stu through a live session, digging into why founders struggle with focus, cheap dopamine, and social media addiction. What surfaces is a subconscious belief that recognition equals value — and Dallin's framework for identifying and naming the lies that drive self-sabotaging behavior.Whether you're a founder figuring out equity, struggling with focus, or just trying to understand what beliefs are quietly running your decisions, this episode delivers.Topics: Harmon Brothers family, Cove Security founding story, VidAngel employee ownership, co-founder equity, founder mindset, limiting beliefs, high performance coaching, dopamine and focus, Scale Me, startup lessons
He's Taking Down the Nicotine Pouch Industry With Nootropics | Spencer Johnson | Episode 54
Spencer Johnson stood on a street corner with a cardboard sign looking for investors — and it actually worked. The founder of Neuro Pouch (nootropic pouches that replace nicotine with cognitive enhancers like lion's mane) shares how a health diagnosis became his business calling, how he landed his first angel investor through a LinkedIn post, and what it takes to survive the early startup grind. Stu gets into contracts, fundraising strategy, brutal founder honesty, and why building a team is the real unlock. This one's for anyone in the trenches right now.
He Built a $1 BILLION Trampoline Empire From Rock Bottom | Case Lawrence | Episode 53
Case Lawrence built Sky Zone from nothing — no funding, no industry, no safety net. In this episode, the founder of the world's biggest trampoline park brand shares how he went from a failed real estate concept and near-bankruptcy to creating a $1B empire. We talk angel investing, equity splits, the sacred investor-entrepreneur relationship, and why watching your team win is the real payoff. His new book "Off the Ground" is available for preorder on Amazon.
Good Marketing Beats Good Business, And How to Fix That | Dennis Yu | Episode 52
What if the best business doesn't win—the best marketer does? Dennis Yu, a former Yahoo search engineer and co-author of books that sold 800,000 copies, is on a mission to close that gap.Dennis isn't an SEO trying to trick search engines—he's a search engine engineer who built the systems SEOs try to game. His unique perspective reveals why good businesses fail while inferior competitors with better marketing thrive.In this episode:Google's E-E-A-T Framework: Experience, Expertise, Authority, Trust—and why the first "E" changed everything before ChatGPT launchedPerceived authority vs. actual authority: Why you need both, and which one drives sales firstThe CNN story: How arguing with Mark Zuckerberg on live TV created instant perceived authorityYahoo engineer insights: Working alongside the inventor of PHP and what limiting beliefs look like at the highest levelsLive ChatGPT demo: We ask AI to analyze Stu's authority in real-time (the results are fascinating)Why you don't have a knowledge panel: And how pre-revenue founders can get one through strategic contentThe #1 strategy for founders: Start a podcast—here's exactly how to turn 10 episodes into a book, ads, and Amazon #1 rankingsContent repurposing system: The "Mexican food" metaphor—same ingredients (beans, cheese, rice), different forms (burrito, taco, enchilada)Brandon Agronoff case study: How a 14-year-old followed Dennis's advice and scaled to 300 VAs, $200K/month in ad spend, and nearly $1M/month in personalized sock salesThe personalized socks hack: Why Dennis ships custom face socks to every podcast guest (and how it costs only $14 end-to-end)Servant leadership as personal branding: Why introverts can build massive authority without being "on stage"Dennis Yu's Core Philosophy: "I love seeing other people win. There are good people who work hard and deserve success, but someone with better marketing beats them. I want to eliminate that gap."Best for:Founders who are "good at what they do" but struggling with marketingIntroverts who don't want to be "influencers" but need authorityAnyone trying to understand how Google actually ranks contentEntrepreneurs looking for low-cost, high-leverage content strategiesTechnical founders who need to build perceived authorityConnect with Dennis Yu:Company: BlitzMetricsLinkedIn: Dennis Yu (most active)Stages spoken: 850+ globallyBooks: Co-author of #1 Amazon books on Facebook Ads and Google Ads with Perry MarshallKey Takeaway: You don't need to be a celebrity to build authority. You need strategic visibility with the right people, consistent proof of results, and a system to amplify both. Start a podcast, interview 10 authorities in your space, and let AI + content repurposing do the rest.
8 Kids, 2 Companies on Inc 5000, and a Divorce | Bubba Page | Episode 51
What does it take to make the Inc 5000 list five times, raise eight kids, survive a divorce, and come out stronger? Bubba Page (real name: Brandt) knows—and his journey will challenge everything you think about entrepreneurship, faith, and family.In this episode:Why Bubba bootstrapped his first company (Launch Leads) to $500K/year without raising a dollarThe brutal reality of venture-backed failure: How Techstars and VC money led to his hardest seasonThe 9-10 Rule for influencer marketing: Why 90% of influencers won't work (and how to find the 10% who crush it)Working with your spouse: Ground rules for business partnerships in marriage (and why his didn't survive)The 50-week prayer experiment: How Bubba found God after feeling spiritually empty his entire life"Choose yourself for 12 months": The monk who changed his body, mind, and businessWhy he tells first-time founders: DON'T raise venture capital (even though he's now a VC)Building Influence VC: Writing $25K-$500K checks into startups through his syndicateThe Page Company: Selling digital products to millions of followers (and the lessons from running it with his ex-wife)What investors REALLY look for: Relationship, traction, and market size—in that orderFather of 8: How he shows up for his kids while running multiple businessesThe hardest thing he's ever been through (hint: it wasn't the business failure)Best for:Founders considering whether to raise VC moneyEntrepreneurs working with their spouseAnyone struggling to balance faith, family, and businessMarketers trying to crack the influencer codeFounders who've faced failure and need to rebuildBubba's Philosophy: "Things don't bring happiness. My family, my relationship with God, my relationships—that brings me true joy. You can have financial freedom and still feel empty. Fix that first."Connect with Bubba Page:Syndicate: Influence VC (on AngelList - free to join)Instagram: @bubbagpageLinkedIn: Bubba PageBusiness Bootcamp: 12-week program for entrepreneursKey Takeaway: Being an entrepreneur is incredible—but dig deep enough and you'll find a wound driving you. Heal that wound, build your relationship with God, and the business success becomes a byproduct, not the purpose.
Working Mom Builds Marketing Agency Across 3 Continents | Bianca McDown Reber | Episode 50
What happens when you say yes to a client project you have no idea how to do? Bianca McDown-Reber shares her journey from teaching herself to code in 60 days to building VoxxVoice, a thriving 17-person marketing and advertising agency that operates across three continents.In this episode:The difficult choice between two marriage proposals that taught her about high-stakes decisionsLearning to code in 60 days to land her first client (with zero coding background)Two kidnapping experiences in South Sudan that changed her perspective on timeRunning a 17-person global agency while traveling to 29 countries with two kidsWhy she refuses to nap and what "chasing your potential" really meansHer new book: "You're Not Just a Mom" - written in the trenches of motherhoodBalancing marriage to a medical resident, motherhood, and business growthThe "9-hour doom scroll" problem and how to audit your timeBest for:Female founders navigating motherhood and businessEntrepreneurs who feel stuck in the "early struggle"Anyone who needs a kick in the pants to stop waiting for perfect conditionsConnect with Bianca:Company: VoxxVoice.comLinkedIn: [most active]Instagram: @[handle]Email: [email protected] Pre-Order: "You're Not Just a Mom: It's Time to Find You and Your Purpose" (Available next month)
Startup Success: Lessons from a $20M+ Founder Turned VC | Tyler Richards | Episode 49
The Science of Startup Success: Why 95% of Funded Startups Fail (And How to Be in the 5%) Think raising money will solve your startup problems? Think again. In this episode, Tyler Richards—serial exited entrepreneur, General Partner at Startup Ignition Ventures, and founder who scaled DevMountain to $10M in revenue and a successful exit—reveals why most venture-backed startups crash and burn, and exactly how to validate your business idea before wasting time and money. What You’ll Learn: ✅ The Quibi disaster: How a $2 billion startup failed in just 7 months (and the lesson every founder needs to know) ✅ The Lean Startup methodology: Tyler’s step-by-step scientific approach to building businesses that actually work ✅ The Business Model Canvas framework: How to move from guesses to facts in all 9 critical areas of your business ✅ Real case study: How one company made 7 pivots and sold for $100M after raising just $250K ✅ The riskiest assumption exercise: Identify what could kill your startup (before it does)About Tyler Richards: Tyler Richards is General Partner at Startup Ignition Ventures, a pre-seed venture fund that actively mentors the startups it invests in. Tyler founded and scaled DevMountain to $10M in revenue before a successful exit in 2016. He now runs the Startup Ignition Bootcamp, which has helped over 1,200 companies validate and scale their ideas using lean startup methodology. Working alongside his father John Richards (who took InfoSpace public), Tyler leads investments in validated tech and software business models across Utah and the Mountain West. Named to Utah’s 2025 “40 Under 40” list. Connect with Tyler Richards: ∙ Startup Ignition: https://www.startupignition.com ∙ Startup Ignition Ventures: https://www.startupignition.vcSubscribe to Startups with Stu for weekly conversations with founders, investors, and entrepreneurs who are building real businesses the right way—no fluff, just actionable startup advice from people who’ve done it. Keywords: startup advice, lean startup, business validation, venture capital, entrepreneurship podcast, how to start a business, product market fit, business model canvas, startup funding, bootstrap startup, entrepreneur tips, Tyler Richards, Startup Ignition, Utah startups
Law Firm Panic Attack Leads to $26M Entertainment Empire Exit
What happens when a $180,000 M&A attorney has a panic attack on the way to work and throws away his legal career for escape rooms? Raleigh Williams built Alcatraz Escape Games from zero to a $26 million exit across four entertainment brands in Utah, Arizona, and Texas. After leaving a prestigious law firm against his father's wishes, Raleigh spent two years in his in-laws' basement before creating an entertainment empire. In this episode of Startups with Stu, host Stuart Draper explores Raleigh's transformation from self-employed business owner to asset builder, including the brutal reality of being told his profitable business was "worth zero" by strategic buyers. Raleigh shares insights on the three stages of entrepreneurship, surviving COVID with $350,000 monthly rent obligations, and why he represented himself through nine transactions instead of using investment bankers. He reveals the mindset shifts required to build a sell-able business and his current work helping entrepreneurs through exitOS and his book "The Creator's Call."Follow Startups with Stu:Website: https://www.startupswithstu.com/ YouTube: https://www.youtube.com/@StartupsWithStu Instagram: https://www.instagram.com/StartupswithStu/Follow Stuart Draper: LinkedIn: https://www.linkedin.com/in/draperstu/ Instagram: https://www.instagram.com/draperstu/Follow Raleigh Williams: LinkedIn: https://www.linkedin.com/in/raleigh-williams/Book: The Creator's Call on AmazonAlcatraz Escape Games: https://alcatrazescapegames.com/ Website: https://exitos.io
25-Year Business Veteran Creates Blue Unicorn Protein Bar Empire at 50
What happens when a former security company CEO discovers a protein bar so good his kids beg for it daily? Jason Christensen went from teaching business students to building Blue Unicorn, a protein bar brand growing 25% month-over-month with 50% subscription sales. After selling his first company to private equity and spending five years as a BYU professor, Jason stumbled into the food industry when he tasted Dr. Luke Tolley's "unicorn" creation - a fluffy protein bar with impossible nutrition that actually tastes like dessert. In this episode of Startups with Stu, host Stuart Draper dives into Jason's transition from service-based business to consumer products, including the nightmare of promising 3,000 bars before knowing how to make them and the expensive lessons of manufacturing mistakes. Jason shares insights on building subscription-based food businesses, leveraging university partnerships for talent, and the emotional decision to leave comfortable retirement for the startup grind. He reveals why parents hide Blue Unicorn bars from their kids and his strategy for geographic retail expansion across western states.Follow Startups with Stu:Website: https://www.startupswithstu.com/YouTube: https://www.youtube.com/@StartupsWithStuInstagram: https://www.instagram.com/StartupswithStu/Follow Stuart Draper:LinkedIn: https://www.linkedin.com/in/draperstu/Instagram: https://www.instagram.com/draperstu/Follow Jason Christensen:LinkedIn: https://www.linkedin.com/in/jason-christensen-9808b9/Follow Luke Tolley:LinkedIn: https://www.linkedin.com/in/luke-tolley-4900a26/Follow Blue Unicorn:Website: https://www.blueunicorn.com/ Instagram: https://www.instagram.com/blueunicornofficial/ Facebook: https://www.facebook.com/blueunicornmagic/ TikTok: https://www.tiktok.com/@blueunicornofficial
Former Model Creates $5M Business After Hitting Rock Bottom
What happens when a successful NYC model loses everything, battles depression, and discovers her life purpose through a rescue horse? Natalia Graf-Anders transformed her darkest moment into a multi-million dollar equestrian empire that's revolutionizing how women see themselves in riding apparel. After years of modeling and corporate sales left her empty and dependent on Adderall, Natalia moved back home with nothing but found healing through horses. In this episode of Startups with Stu, host Stuart Draper explores Natalia's journey from three products in her apartment to building Sync Equestrian into a business targeting $5-6 million this year, up from $2.1 million last year. Natalia reveals her psychology-based advertising strategies, the manifestation practices that fuel her success, and her approach to building an empowerment-focused brand that sets trends instead of following them. She shares insights on nervous system training for money mindset, the importance of trusting business intuition, and scaling from solo founder to leading a team while maintaining authentic brand messaging.Follow Startups with Stu:Website:https://startupswithstu.com/YouTube:https://www.youtube.com/@StartupsWithStuInstagram:https://www.instagram.com/StartupswithStu/Follow Stuart Draper:LinkedIn:https://www.linkedin.com/in/draperstu/Instagram:https://www.instagram.com/draperstu/Follow Natalia Graf-Anders:Instagram:https://www.instagram.com/nataliaornatascha/Follow Sync Equestrian:Website:https://syncequestrian.com/https://www.sync-academy.com/Instagram:https://www.instagram.com/syncequestrian/Facebook:https://www.facebook.com/syncequestrian
How Founders Save Millions in Taxes using QSBS on Exit Day
What if you could legally exclude up to $10 million from taxes when selling your startup? Richard Levychin from Galleros Robinson breaks down the Qualified Small Business Stock (QSBS) Section 1202 tax code that most founders overlook until it's too late. In this episode of Startups with Stu with host Stuart Draper, Richard explains how proper entity structure and timing can save entrepreneurs millions during exit events, sharing real cases where clients turned $100K investments into $9 million payouts. Stuart Draper explores the critical setup requirements, five year holding periods, and conversion strategies for LLCs and S-Corps looking to qualify. From Delaware C-Corporation benefits to advanced tax mitigation techniques rated on a 1 to 10 risk scale, this conversation delivers actionable insights for companies in their growth stage. Richard also reveals common due diligence pitfalls that kill deals and why having the right advisory team makes the difference between keeping your wealth and losing it to Uncle Sam. Follow Richard Levychin:LinkedIn: https://www.linkedin.com/in/richard-levychin-cpa-cgma-b22386/ Follow Startups with Stu:Website: https://www.startupswithstu.com/ YouTube: https://www.youtube.com/@StartupsWithStuInstagram: https://www.instagram.com/StartupswithStu/ Follow Stuart Draper: LinkedIn: https://www.linkedin.com/in/draperstu/ Instagram: https://www.instagram.com/draperstu/
Nine-Time Founder Breaks Down Entrepreneurship's Reality
What separates fundable startups from those that never attract angel investment? Akbar Jaffer, angel investor and Professor of Entrepreneurship at Grand Canyon University, has evaluated hundreds of startups through his nine-company founding experience at Snapfish, ZorroSign, and other ventures. In this episode of Startups with Stu with host Stuart Draper, Akbar reveals his systematic 6-point investment criteria that determines whether he writes a check or walks away. Stuart explores Akbar's methodology for assessing market position, founder expertise, and team composition, plus his requirement that founders have skin-in-the-game through personal financial investment. Akbar explains his preference for three-founder teams over solo entrepreneurs or larger groups, shares examples of world-changing startups that attracted his investment, and discusses the scaling potential indicators that signal strong exit opportunities for angel investors. Follow Akbar Jaffer: LinkedIn: https://www.linkedin.com/in/akbarjaffer/ Website: https://marketing-qa.com/ Snapfish: https://www.snapfish.com/home Follow Startups with Stu: Website: https://startupswithstu.com/ YouTube: https://www.youtube.com/@StartupsWithStu Instagram: https://www.instagram.com/StartupswithStu/ Follow Stuart Draper: LinkedIn: https://www.linkedin.com/in/draperstu/ Instagram: https://www.instagram.com/draperstu/
Founder Uses ChatGPT to Build Complete Business Plan in Minutes
Ryan Petersen transforms startup planning by using ChatGPT as his business development partner for Swintros, a new job platform technology. In this episode of Startups with Stu, host Stuart Draper watches as Ryan generates a complete business plan in real time using just one simple prompt to ChatGPT 4.0. The AI instantly creates executive summaries, market analysis, financial projections, and go-to-market strategies based on previous conversations Ryan had with the system. Stuart and Ryan show live adjustments to pricing models and financial forecasts, revealing exactly what's possible when you feed AI the right information upfront. Ryan shares his approach to working with AI rather than against it, emphasizing that tools like ChatGPT excel at business validation and identifying gaps entrepreneurs might miss. Building a startup in 2025 has never been more accessible, and this episode proves that comprehensive business planning no longer requires extensive spreadsheet knowledge or market research skills. Follow Startups with Stu: Website: https://startupswithstu.com/ YouTube: https://www.youtube.com/@StartupsWithStu Instagram: https://www.instagram.com/StartupswithStu/ Follow Stuart Draper: LinkedIn: https://www.linkedin.com/in/draperstu/ Instagram: https://www.instagram.com/draperstu/
Serial Entrepreneur's Mental Health Mission After Two Eight-Figure Exits
What happens when chips on your shoulder fuel two successful exits but leave you empty at the finish line? Tom Telford sold his institutional finance companies for eight figures by age 37, only to discover his anger-driven motivation vanished the moment he achieved financial freedom. In this episode of Startups with Stu with host Stuart Draper, Tom Telford, shares his transformation from proving doubters wrong to building LEVO Mind Care with three women partners focused on the biological side of mental health treatment. Stuart Draper explores Tom's disciplined goal-setting approach that turned a struggling student with ADHD into a serial entrepreneur, his strategic pivot from banking to credit unions during the 2008 crisis, and the prayer-based mentorship philosophy that connected him with industry giants. Tom reveals the biopsychosocial model of mental health care, explains why physical assessment often precedes therapy, and discusses his mission to become the most generous mental health business owner ever while elevating women leaders in healthcare. Follow Tom Telford:LinkedIn: https://www.linkedin.com/in/tom-telford-2168514/ Instagram: https://www.instagram.com/tommystackroom/ Company Website: https://levomind.com/ Follow Startups with Stu: Website: https://startupswithstu.com/ YouTube: https://www.youtube.com/@StartupsWithStuInstagram: https://www.instagram.com/StartupswithStu/ Follow Stuart Draper:LinkedIn: https://www.linkedin.com/in/draperstu/ Instagram: https://www.instagram.com/draperstu/
Hairdresser Turns $500K Investment Into Emotional Intelligence Startup for Kids
What happens when a small-town hairdresser discovers her clients need more than just a haircut? Tami Hymas built five successful businesses in rural Idaho, but her biggest venture yet tackles childhood emotional wellness through cartoon characters that help kids identify and process their feelings. In this episode of StartUps with Stu, Tami shares her journey from salon owner to startup founder, revealing how she invested $500,000 to create the InUPowers program now being tested in juvenile detention centers and schools. Stuart Draper dives deep into Tami's mission-driven approach, exploring the challenges of scaling an education technology business beyond local markets. From government contracts to classroom management tools, this conversation unpacks the reality of building a business that aims to heal young minds while generating sustainable revenue. Tami's story demonstrates that sometimes the most unexpected entrepreneurs create the most needed solutions.
How This Founder Hit $56M Revenue After Living in His Car for a Year Following Bankruptcy
StartFragment StartFragment StartFragment StartFragment What does it take to build a $56 million company after losing everything twice? Jeremy Barker, founder of Murphy Door, shares his incredible journey from making his first $20 million at 21, going bankrupt, and living in his car for exactly one year to building the Kleenex brand of hidden doors. In this episode, Jeremy reveals how he created an entirely new product category from scratch while working as a full-time firefighter, turning a simple hardware concept into a monopoly business that's projected to hit $109 million by 2027. He breaks down the mental shift that saved his life during his darkest moments, why he chose domestic manufacturing over cheap imports, and his contrarian approach to scaling without taking investor money. Jeremy also unveils Pure Brand, his revolutionary customer-to-customer sales platform that converts prospects at 47% compared to traditional website conversion rates of 0.24%. His hard-earned wisdom about resilience, the dangers of early success, and building authentic value over flashy signaling makes this essential listening for any entrepreneur facing setbacks or looking to create a category-defining business. Connect with Jeremy Barker: LinkedIn: https://www.linkedin.com/in/jeremy-barker-02007648/ Instagram: https://www.instagram.com/jbarker482/ YouTube: https://www.youtube.com/@JeremyBarker482 Follow Murphy Door: LinkedIn: https://www.linkedin.com/company/the-murphy-door/ Instagram: https://www.instagram.com/murphydoor/ YouTube: https://www.youtube.com/@murphydoor Twitter/X: https://x.com/murphydoor
This Mother Turned a $40K Yellow Trailer Into a Multi-State Franchise Empire
What started as a $500 college fund goal turned into a frozen custard empire spanning multiple states. Jessica Mortensen shares her unexpected journey from buying a college student's yellow trailer business for $40,000 to building Karie Anne's Frozen Desserts into a thriving franchise operation. In this episode of Startups with Stu, Jessica reveals the pivotal moments that transformed her "summer side gig" mindset into a serious growth strategy, including the leap from eight seasonal trailers to year-round brick-and-mortar locations. She breaks down the harsh realities of franchising - from the massive upfront costs to finding franchisees who won't let high schoolers run their operations unsupervised. Jessica opens up about the internal struggle between her competitive drive and family priorities, sharing why she's considering either bringing on a strategic partner or leveraging debt to reach her next growth phase. Her transparent approach to business challenges, combined with practical insights about managing seasonal cash flow and building systems that work across multiple locations, makes this essential listening for anyone considering franchising or building a family business. Jessica's story proves that sometimes the best business opportunities come disguised as small investments that "feel right."Connect with Jessica Mortensen:LinkedIn: @jessica-mortensenInstagram: @karieannesdessertsWebsite: karieannes.com
9 Years, 4 Kids, 1 Kitchen Vision: How This Mom Built a Hair Extension Empire From Scratch
Standing alone in her parents' kitchen making a quesadilla, Whitney Rigby heard a male voice tell her to "create magnetic hair extensions" - and nobody else was home. Nine years later, that supernatural moment has transformed into the world's first magnetic hair extension company, with investors begging to get in and trade shows selling out instantly. In this episode of Startups with Stu, Whitney reveals how she went from aspiring celebrity hairstylist to bootstrapped entrepreneur while raising four kids, including the wild chain of "coincidences" that led a multi-million dollar CEO to mentor her after her father-in-law randomly installed blinds at his house. Host Stuart Draper dives deep into the strategic decisions that matter most - why Whitney turned down Shark Tank when pregnant, how she survived her husband losing his job twice during development, and the real reason it took six years to perfect a product that seemed simple. The conversation gets tactical when Stuart breaks down exactly why Whitney needs to raise money now, the difference between debt and equity financing, and how inventory challenges are actually the best problem to have. For entrepreneurs wondering how to balance family life with startup dreams, this episode offers a blueprint for building something meaningful without sacrificing what matters most.
This Founder Turned Down $500K to Build a Recruiting Business on Her Terms
Xan Marcucci rejected a $500,000 corporate offer to start Confetti Recruiting as a summer project while caring for her young children. What began with a surprise $20,000 commission check evolved into a thriving business aligned with her family priorities. Xan shares an unconventional perspective, suggesting aspiring entrepreneurs gain corporate experience first and explaining her choice to prioritize flexibility over aggressive growth. She talks about balancing her natural competitiveness with family needs, the wisdom behind bootstrapping, and the advantages of partnership with someone who has different risk tolerance. Sales professionals considering entrepreneurship will appreciate her straightforward assessment of business ownership challenges. Xan presents success as personal freedom and family time rather than maximizing revenue, offering listeners a refreshing alternative to typical startup narratives.
24-Year-Old Founder Reveals the $0 Marketing Strategy That Beats Cold DMs and Paid Ads
While most entrepreneurs struggle with expensive lead generation, 24-year-old Derek Bock discovered a networking strategy that costs nothing but delivers warm leads directly to your inbox. Starting with social media work for a Nebraska gym during COVID, Bock has built multiple ventures and now runs The Doers Podcast, which he strategically uses as his primary business development tool. Bock shares why he chose the lifestyle entrepreneur path over chasing unicorn status, how he generates qualified prospects through strategic conversations, and why he believes podcasting outperforms traditional marketing channels. Having networked his way from college athlete to serial founder, he breaks down the exact framework that transforms podcast guests into business opportunities. Bock also reveals his system for managing 30+ fleshed-out business ideas while maintaining laser focus on current ventures. This episode delivers actionable insights for young founders seeking sustainable growth without venture capital pressure, plus the networking blueprint that can accelerate any entrepreneur's trajectory regardless of age or experience level. Connect with Derek Bock: Instagram: @ thederekbock Gmail: [email protected] LinkedIn: Derek Bock
How This Mom Built a $1M Agency While Working 4 AM Mornings
"I magically carve out hours for my day. So some days I have to start at 4 a.m." This is how Akvile DeFazio, who fled Lithuania during the Cold War with just a wooden crate, manages to run a thriving social media advertising agency while raising a kindergartner. In a decade of business, she's achieved something almost unheard of: she's never been fired by a single client. Starting with zero sales experience and crippling stage fright, Akvile transformed herself from a timid freelancer into a confident agency owner who keynotes major conferences. Her secret? A revolutionary approach that shifted her business model during COVID, turning consulting into 60% of her revenue stream while working fewer hours than traditional account management. After shadowing a mentor who handed over half her clients, Akvile discovered that building genuine relationships trumps aggressive sales tactics every time. She reveals her exact blueprint for creating a lifestyle business that generates serious revenue without requiring a large team, plus the unconventional parental coverage program that allowed her to take real maternity leave as a founder. This episode is a goldmine for anyone wanting to build a sustainable, profitable business while maintaining work-life balance and never compromising on family time.
College Student Founder Gaining Traction With His SaaS Startup
In a recent episode of Startups with Stu, host Stuart Draper, Join us as we explore the innovative journey of Subitt.io, a startup that's transforming how small businesses implement subscription models to drive customer retention. Founder Nick Hepworth shares his insights on building a platform that makes subscription services accessible to mom-and-pop shops, discussing the challenges of educating both businesses and customers while navigating the complex world of local commerce. From his beginnings in Mississippi to managing 50 businesses with 1600 MRR, Hepworth reveals the strategic decisions that led to early traction. The conversation delves into the importance of focusing on success stories rather than scale, the art of building trust with small business owners, and the critical balance between growth and profitability. This deep dive offers valuable lessons for any entrepreneur looking to disrupt traditional business models and create meaningful impact in local communities.
25-Year Expert Shares SBA Loan Secrets
Learn how SBA loans can transform your business dreams as Craig Sherle, VP of SBA Lending at Idaho Central Credit Union (ICCU) with 25 years of small business lending experience, explains exactly how to get financing when other lenders reject you. These government-backed loans (covering 75-85% of the risk) have helped numerous employees become owners - like the restaurant manager who purchased multiple franchise locations and continues expanding. Craig shares specific requirements lenders evaluate, why buying an existing business increases your approval odds, and which free local resources will strengthen your application. With the "silver wave" of Baby Boomer business owners retiring, unprecedented buying opportunities are emerging across America. This episode gives you the practical financial knowledge to join the ranks of successful buyers in what was recently named among the top 5 entrepreneurial paths to wealth building.
Rugby Player's Ripped Jersey Launches $25 Million Sports Apparel Dream
In this episode, we sit down with James Reber who transformed his frustration with torn rugby jerseys into a thriving custom sports apparel business. Starting with just 50 misspelled rugby balls, James now celebrates breaking six figures in Q1 2025—more than his entire previous year's revenue. He shares the exact moment he received his first $72 check and why he still keeps it as a reminder of his entrepreneurial journey. When unexpected layoffs pushed him to go all-in on his side hustle, James found success by focusing on high-quality products and exceptional customer service for niche sports markets. Listen as he explains his strategy for transitioning from a part-time venture to a full-time business with big ambitions, including his vision for a potential $25 million exit. This conversation offers practical insights about manufacturing challenges, family support, and building an effective team of six contractors who are expanding Rebellion Sports across the country.
How Notey's World is Solving the 90% Dropout Problem in Music Learning
Meet Mak Grgic, founder of Notey's World, who's tackling a universal challenge: 90% of people who try learning guitar eventually quit. In this investment pitch, Mak showcases how his Techstars-backed startup transforms musical instruments into actual game controllers, creating an addictive learning experience that's seeing unprecedented user retention—67% at day 90 compared to the industry's measly 2%. With $207,000 in first-year revenue and school partnerships already spanning multiple states, Notey's custom AI technology adapts to each student's specific learning gaps. Parents are witnessing months of progress in just weeks as children suddenly can't wait to practice. The platform's proprietary automatic level generator can transform any song into a personalized game world, complete with notes that control jumping blimps and characters avoiding obstacles. With Grammy artists like Stewart Copeland from The Police signing on as affiliates, Mak explains why this $8 million valuation seed round might be your chance to join the reinvention of music education.
How 3 Execs Built an EdTech Giant with 1M+ Students in 80+ Countries
What happens when three executives who built a million-dollar EdTech company reunite to share their unfiltered startup journey? In this 30th episode of Startups with Stu, founder Stuart Draper and his former executive team Trevor Erickson and Brandon Winter pull back the curtain on their meteoric rise from working out of their homes to becoming a global education powerhouse. The trio tackles head-on questions about validating business ideas, managing side hustles while growing a company, and knowing when you've finally broken through the "will we fail?" ceiling. They share specific strategies they used to position their product as "first in the world" and how they leveraged this unique advantage to fuel explosive growth. Stuart reveals his fundraising mistakes that actually turned into blessings, while Brandon explains why college students selling to professors became their secret weapon. This rare conversation between founders who succeeded together offers invaluable insights for entrepreneurs at any stage - from spotting market opportunities to building a team that embraces an entrepreneurial mindset.
$100 Stakes in $270,000 Properties: The Real Estate Platform Challenging Wall Street Rules
McKay Francis never planned to battle the SEC or catch Grant Cardone's attention when he launched Casa Shares, the investing platform letting broke college students buy real estate for just $10 per share. This episode of Startups with Stu unveils how Casa Shares secured a game-changing federal exemption allowing non-millionaires to invest in property, something 90% of Americans couldn't legally do before. McKay shares his transformation from late-night side-hustler to founder raising $2.5 million while rejecting venture capital offers that would have meant "working until 2am under their rules." His mission began after watching dentists turn $500,000 salaries into "tens of millions" through real estate investments while average Americans got locked out. Now Casa Shares users earn quarterly dividends, property appreciation, and tax benefits without needing $300,000 starter funds. With property values doubling in recent years, McKay explains why investors should build their "snowball effect" portfolio starting at 18 instead of the typical age 46, potentially turning small investments into millions through earlier compounding.
3 Businesses, 4 Kids, and 1 Pharmacy: The Unconventional Path to Angel Investing
From creating America's #1 cake mix to writing a $25,000 check that launched an educational empire—Corey Smith's unexpected journey unfolds in this episode of Startups with Stu. When Stuart Draper lost his third job in a row, it was Corey's unwavering belief that transformed a desperate situation into Stukent, a company that would eventually impact over a million students worldwide. But before becoming an angel investor, Corey walked away from his six-figure Boston career to save his father's struggling pharmacy in rural Idaho, dragging his California-raised wife Cindy into a life she never imagined. The Smiths reveal the hidden tensions of family business ownership, the brutal truth about equity distribution, and what happens when 87% of your investments fail. As Southeast Idaho's entrepreneurial scene evolves, Corey delivers a stark warning about integrity that every founder needs to hear: "Trustworthiness is a rare commodity." This conversation exposes both the triumphs and scars of building businesses that matter in places where most people say it can't be done.
Losing Everything and Rebuilding as a Founder with John Rampton
From eight-figure exit to nearly $1 million in debt in less than a year! Serial entrepreneur John Rampton joins Stuart Draper on Startups with Stu to share his journey from childhood candy stand owner to multi-million dollar success. John reveals how writing for major publications like Forbes and Entrepreneur helped launch his businesses, and details the painful collapse of his company organize.com after Amazon shut them down and left him financially devastated. After hitting rock bottom—begging for gas money and facing eviction—John's fortunes turned when a random connection from his past led to work that sustained him while rebuilding. Through personal stories, including losing 65 pounds through a monk's unconventional four-year plan, John emphasizes the importance of taking care of yourself first before helping others in your "circles of influence." His current venture, Calendar.com, handles scheduling for major healthcare providers worldwide with just eight employees, demonstrating his ability to build efficient, profitable businesses.
Building Wealth Without Sacrificing Family
From turning down multi-million dollar Wall Street recruitment bonuses to building a billion-dollar wealth management firm, Chad Willardson's entrepreneurial journey is anything but conventional. In this captivating episode of Startups with Stu, Chad reveals how he walked away from a $1.4M salary at Merrill Lynch to start Pacific Capital, taking a 70% pay cut to pursue his vision of serving entrepreneurs differently. He shares the fascinating story of surprising his wife with a private jet purchase (and her unexpected reaction), and explains why he turns down high-profile clients like NBA players to stay true to his entrepreneurial niche. Chad breaks down why he believes the "hustle culture" is a lie, revealing how he built a thriving business while maintaining an 8 AM-3 PM workday for his team and prioritizing family life. Drawing from his experience managing $1.45 billion in assets, Chad offers counter-intuitive wisdom about wealth building, arguing that diversification isn't always the answer. This episode is packed with invaluable insights for entrepreneurs looking to scale their businesses while building meaningful lives.