Startups With Stu

Stuart Draper
  • 5.0 (8)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY

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

  1. 15H AGO

    How Raleigh Williams Sold His Business for $26M | Episode 59

    How Raleigh Williams Sold His Business for $26M | Episode 59 He 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 STU Instagram: @stu  Website: https://startupswithstu.com #entrepreneur #startups #founderstory #escaperoombusiness #businessexit #exitstrategy #peptides #glp1 #smallbusiness #startupswithstu

    51 min

  2. 4D AGO

    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 CHENG Website: https://taelor.style 🔗 CONNECT WITH STU Instagram: @stu Website: https://startupswithstu.com #entrepreneur #startups #founderstory #womenfounder #fashiontech #AIstartup #venturecapital #immigrantfounder #startupfunding #siliconvalley

    51 min

  3. MAR 26

    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 publicly CONNECT WITH WALLY Instagram: @wallyroskelly CONNECT WITH STU Instagram: @stu Website: https://startupswithstu.com

    1h 4m

  4. MAR 16

    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

  5. MAR 11

    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

  6. MAR 3

    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.

  7. FEB 24

    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.

  8. FEB 16

    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 launched Perceived authority vs. actual authority: Why you need both, and which one drives sales first The CNN story: How arguing with Mark Zuckerberg on live TV created instant perceived authority Yahoo engineer insights: Working alongside the inventor of PHP and what limiting beliefs look like at the highest levels Live 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 content The #1 strategy for founders: Start a podcast—here's exactly how to turn 10 episodes into a book, ads, and Amazon #1 rankings Content 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 sales The 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 marketing Introverts who don't want to be "influencers" but need authority Anyone trying to understand how Google actually ranks content Entrepreneurs looking for low-cost, high-leverage content strategies Technical founders who need to build perceived authority Connect with Dennis Yu: Company: BlitzMetrics LinkedIn: Dennis Yu (most active) Stages spoken: 850+ globally Books: Co-author of #1 Amazon books on Facebook Ads and Google Ads with Perry Marshall Key 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.

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5
out of 5
8 Ratings

About

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

Information

  • Creator
    Stuart Draper
  • Years Active
    2024 - 2026
  • Episodes
    59
  • Rating
    Clean
  • Copyright
    Copyright © 2026 Stuart Draper. All rights reserved.
  • Show Website
    Startups With Stu

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