Startups With Stu

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 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.

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

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 dollar

The brutal reality of venture-backed failure: How Techstars and VC money led to his hardest season

The 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 business

Why 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 syndicate

The 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 order

Father of 8: How he shows up for his kids while running multiple businesses

The hardest thing he's ever been through (hint: it wasn't the business failure)

Best for:

Founders considering whether to raise VC money

Entrepreneurs working with their spouse

Anyone struggling to balance faith, family, and business

Marketers trying to crack the influencer code

Founders who've faced failure and need to rebuild

Bubba'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: @bubbagpage

LinkedIn: Bubba Page

Business Bootcamp: 12-week program for entrepreneurs

Key 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.

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 decisions

Learning 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 time

Running a 17-person global agency while traveling to 29 countries with two kids

Why she refuses to nap and what "chasing your potential" really means

Her new book: "You're Not Just a Mom" - written in the trenches of motherhood

Balancing marriage to a medical resident, motherhood, and business growth

The "9-hour doom scroll" problem and how to audit your time

Best for:

Female founders navigating motherhood and business

Entrepreneurs who feel stuck in the "early struggle"

Anyone who needs a kick in the pants to stop waiting for perfect conditions

Connect with Bianca:

Company: VoxxVoice.com

LinkedIn: [most active]

Instagram: @[handle]

Email: [email protected]

The Science of Startup Success: Why 95% of Funded Startups Fail (And How to Be in the 5%)

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

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.vc

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