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

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

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

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

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

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

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.

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.