Startups With Stu

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.

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.

The gaming industry surpasses music, movies, and sports combined in market size, yet Luke Richey envisions something bigger than profits alone. As founder of America's oldest augmented reality company Gravity Jack, he's crafting a revolutionary gaming experience backed by legendary Atari founder Nolan Bushnell and protected by a powerful patent portfolio. After building games that generated $35M+ monthly revenue, Richey is rejecting the "dopamine for dollars" model to create experiences that forge real-world connections and preserve 7,000+ endangered languages. His vision has already secured $550K of a $3.5M raise at a $23.4M valuation. Through stories of wrestling championships, startup victories, and spiritual transformation, Richey showcases how gaming can become a force for genuine human connection and social change. This episode offers founders a masterclass in building companies that deliver both exceptional returns and meaningful global impact, while revealing the untapped potential of gaming as a catalyst for social good.

What's the smartest way to turn $10,000 in savings into a business that gives you true time and financial freedom? In this episode of Startups with Stu, Ethan Clark reveals his journey from real estate investing to co-founding Idaho Falls Junk Removal, while plotting an ambitious exit strategy that could multiply his company's value. Host Stuart Draper breaks down the counterintuitive truth about real estate versus service businesses - why a demolition company could potentially grow faster than property investments, and how to structure deals that let the business pay for itself. Through real-world insights, you'll learn why hunting for distressed business owners in their mid-60s could be your ticket to entrepreneurial success, and how creative financing can help you acquire a $300,000 business with just $10,000 down. The conversation takes a fascinating turn when Stuart explains why subscription models could transform a simple service business into a highly valuable asset, potentially tripling its sale price. For entrepreneurs looking to build wealth without being chained to their business, this episode offers a masterclass in strategic thinking - from finding the right opportunities to engineering your own exit, all while maintaining the freedom to spend time with family.

What happens when you combine the urgent need for expert voices with publishers' insatiable demand for authentic content? Brett Farmiloe, founder of Featured.com, shares how he transformed this market gap into a thriving platform that now powers content for industry giants like Fast Company, Forbes, and HubSpot. In this episode, Brett reveals the strategic pivot that led him from running a 500-client digital marketing agency to building a two-sided marketplace that's doubling year after year. He breaks down the chicken-and-egg challenge of marketplace businesses, explaining how focusing on the "hard side" - securing top-tier publishers - became their key to scaling. From validating their product with zero publishing partners to now serving over 1,000 prominent media outlets, Brett shares invaluable insights about product-led growth, staying lean with a team of seven, and why sometimes the best partnerships are the ones you keep close to the vest. His practical wisdom about unlocking expertise at scale and navigating the AI content revolution makes this episode essential listening for founders building marketplace businesses or anyone looking to establish themselves as an industry expert.

"You're not a marketing genius. You don't even have a job. You do yoga all the time." These were the words Curtis Matsko's girlfriend hurled at him when he boldly declared he was going to quit his job and start a hundred-million-dollar company selling leather journals. Her response? "That's the stupidest idea ever." Fast forward to today, and Curtis Matsko didn't just prove her wrong - he built a $200 million global leather goods empire that sells one product every three seconds on Black Friday. From hustling at art festivals to building a 600,000 square foot international operation, Matsko's journey is a masterclass in entrepreneurial audacity and marketing genius. What happens when you ignore everyone who says your idea is crazy and instead bet everything on your vision? By treating marketing as his primary product and breaking through every limitation, Curtis reveals the unconventional strategies that transformed Portland Leather Goods from a garage startup to a rapidly expanding brand. With raw honesty and infectious energy, he shares critical lessons about surrounding yourself with motivated people, breaking through your own expectations, and why data should always serve decision-making. This isn't just another startup story - it's a blueprint for turning seemingly impossible dreams into world-changing businesses. If you're an entrepreneur looking for real-world inspiration and tactical insights, this episode will light a fire under your ambitions.

In this week's episode of Startups with Stu, discover what happens when you combine the hype of custom sneakers with B2B marketing. Matt Williams reveals how his company DSCMFRT is transforming corporate gifting and social media engagement by turning Nike and Adidas sneakers into viral marketing assets. From crafting money-themed Air Jordans to creating region-specific designs for real estate firms, Matt shares how a traditional sneaker customization business evolved into a B2B success story that's generating 40+ hours of LinkedIn video views from 30-second content. With fascinating stories of corporate shoe designs and viral unboxing moments, Matt breaks down his innovative approach to turning mundane business logos into conversation-starting footwear that employees actually want to wear. His journey reveals an unconventional path to building recurring revenue streams, transitioning from one-off shoe sales to full-scale social media management and LinkedIn advertising services. For entrepreneurs looking to stand out in crowded B2B spaces and marketers seeking fresh engagement strategies, this episode offers a masterclass in turning physical products into digital marketing gold.

What happens when you trade a cushy Target supply chain job for a risky startup role with no salary for five months? For Brandon Winter, former CRO of Stukent and founder of Fundraise Genius, it led to helping build Stukent from zero to serving over a million students across 80 countries. Going behind the scenes of Stukent's meteoric rise, Brandon reveals how Stukent grew from a makeshift warehouse office (complete with a porta-potty!) into an ed-tech powerhouse that revolutionized digital marketing education. Through stories of shared hotel rooms in Singapore and intense strategy meetings, Brandon breaks down the delicate balance of building a sales culture that drives astronomical growth while maintaining team cohesion. Get an insider's look at how early-stage compensation negotiations work, why having a mission bigger than money attracts top talent, and what it takes to transition from "player-coach" to true sales leadership. For founders looking to build high-performing sales teams and professionals considering the leap into startups, this episode offers an unfiltered look at both the grind and glory of startup life.

Every morning, Stukent's first CTO Mike "Turbo" Farmer would burst into the warehouse-turned-office shouting "TURBO!" – bringing energy and fun to a startup racing against impossible deadlines. As the sole technical leader, Mike powered through Christmas coding sessions to rebuild Stukent's entire platform, ultimately helping create software that would impact students at over 300 universities. Through stories of late-night debugging sessions, heated strategy meetings, and the pressure of being the company's only engineer, Mike breaks down what it really takes to build mission-critical educational software from scratch. The conversation explores the delicate balance of technical decisions in a non-technical founding team, the importance of stock option understanding for early employees, and how celebrating small wins helped the team push through their toughest challenges. For founders looking to build strong technical partnerships and engineers considering joining early-stage startups, this episode offers invaluable insights into the human side of startup engineering leadership.