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Startups With Stu

Startups With Stu

Von: Stuart Draper
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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.Copyright © 2026 Stuart Draper. All rights reserved. Management & Leadership Ökonomie
  • She Did WHAT to Get a CEO’s Attention?! | Episode 60
    Apr 8 2026

    She sent an unscripted, badly lit, walking-outside selfie video to the CEO of Caterpillar — one of the

    largest 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, an

    11-year marketing agency that works with everyone from stormwater compliance companies to Mr. Beast's

    team. She sat down with Stu at a live Startups with Stu retreat in Highland Park, Idaho — after spending

    seven 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 STU

    Instagram: @stu

    Website: https://startupswithstu.com


    #entrepreneur #startups #founderstory #womenfounder #marketingagency #salestips #bodylangage #BYUIdaho #livewithurgency #smallbusiness
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    50 Min.
  • How Raleigh Williams Sold His Business for $26M | Episode 59
    Apr 6 2026

    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




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    51 Min.
  • From Couch Surfing to $7M Startup - Story of Anya Chang | Episode 58
    Apr 2 2026

    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



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    51 Min.
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