The UpFlip Podcast

Dominic Rubino knows a painful truth about the trades: being great at your job has almost nothing to do with whether your business makes money. Growing up in an immigrant family of welders and framers, he watched talented contractors grind for years just to barely break even. After nearly going bankrupt running his own house-painting business, Dominic realized he needed to stop acting like a trade...

Jen McKee knew something in 2021 that the rest of the trades industry didn't: local businesses can absolutely dominate on TikTok. When a local plumbing company agreed to test her strategy, they didn't just get views—they generated massive inbound leads, scored thousands of five-star reviews, and became an industry icon without spending a single dollar on ads. As the founder of Key Heart Ma...

Brian Samson knows a harsh truth about the current American economy: if you run a service business right now, the math is brutal. Labor is incredibly expensive, turnover is high, and finding reliable operators can feel like a full-time job. But Brian has a cheat code. After years of running talent acquisition for hyper-growth, VC-funded tech startups in Silicon Valley, Brian took his high-level re...

Amber Farrell grew up watching her father dig ditches as a master plumber for 40 years. That upbringing gave her a genuine respect for blue-collar entrepreneurs—and a deep frustration watching them get sold expensive, unmeasurable marketing campaigns they didn't actually need. After selling her first digital marketing agency, Amber launched Far Beyond Marketing to empower trade and home servic...

Kara Ward found herself in a nightmare scenario on April 1st, 2020: her husband unexpectedly lost his job, they had zero severance, and a staggering $60,000 in medical debt hung over their heads. Desperate to pay the mortgage, Kara dragged an old dresser into her garage, painted it with leftover wall paint, and posted a photo on Facebook. That single post sparked a life-changing side hustle. Fast...

Oleg Lee started with a simple request: he asked his dad to print a custom-shaped pillow of his late childhood dog, Izzy. When he posted a photo of the lifelike pillow on Facebook, the internet lost its mind. Today, that single viral moment has evolved into a $20 million-a-year manufacturing empire producing 400,000 custom pillows annually. In this episode of the UpFlip Podcast, Oleg breaks down h...

Chris Heckman stared at his computer screen with a sinking feeling: his first major e-commerce store launch was a complete zero, leaving him with $100,000 in credit card debt. Instead of crawling back to the safety of his corporate job at Amazon, he adopted a "burn the boats" mentality, treated his failures as data, and built a print on demand (POD) powerhouse that has since generated ov...

Steve Griggs transforms backyards into multimillion-dollar outdoor experiences. After 40 years in the landscaping industry, Steve has built a $5M/year design firm catering to high-net-worth clients—including lawyers, investors, athletes, and celebrities. In this episode, Steve sits down with Ryan Atkinson to share the gritty reality of scaling a premium service business. From trimming bushes with...

Seif El-Sahly walked away from a comfortable, six-figure engineering career working in -50 degree northern mines to start a construction and renovation business in Hamilton, Ontario. Today, New Fort Inc. generates multiple seven figures a year, and Seif is breaking ground on massive 22-unit developments after successfully partnering with Home Depot and shooting a pilot for HGTV. In this episode, S...

Victoria Westcott went from a burnt-out school teacher grading online lessons to the founder of a cleaning empire generating over $1.7 million in revenue—all starting with a free 21-day online course. In this episode of the UpFlip Podcast, Victoria pulls back the curtain on how she and her sister built Oak Bay Clean into a local powerhouse boasting 81% recurring revenue and over 200 five-star revi...

Rod Khleif immigrated to the US in deep poverty, wearing Goodwill clothes and eating cereal with powdered milk. Decades later, he built a massive real estate portfolio—only to lose $50 million in the 2008 housing crash. But his story didn't end there. In this episode of the UpFlip Podcast, Rod sits down with us to share the raw, unfiltered truth about building wealth, losing it all, and the ex...

Natalia Zorina owns a fleet of 68 cars and generates over $3.5 million in gross revenue ($300k net)—but she says you can start this exact business tomorrow with zero dollars and zero vehicles of your own. In this episode, Natalia pulls back the curtain on the highly lucrative world of car rentals and co-hosting. Operating in Miami—a market notorious for rental scams—Natalia has built a trusted bra...

Most people only eat funnel cake once or twice a year at a fair, but Cheyenne loved them so much she would buy expensive amusement park tickets just to get her fix. Tired of driving out of her community to satisfy a craving, she launched a makeshift funnel cake pop-up shop in her front yard with just a tent, a fryer, and a $5 menu. Today, that front-yard Startup is Fun Diggity, a dessert brand gen...

Brian grew up in Detroit believing that if you mastered your plumbing craft, the money would automatically follow. He quickly realized the highest-paid technicians weren't the best wrench-turners—they were the best communicators. After mastering the art of persuasion, Brian stepped in as GM of Benjamin Franklin Plumbing and skyrocketed their revenue to $6.2 million in just two years by triplin...

Ray Vardy was a pre-med student drowning in $1,200 monthly payments for a Tesla he couldn't afford. Desperate to cover the costs, he tried renting it out on existing platforms, only to have the car scratched, smoked in, and, in one instance, used to rob a bank. Instead of accepting defeat, Ray leaned into Product development and built a software solution to automate the entire rental process....

A lot of people believe you need a massive amount of capital, a revolutionary idea, or years of experience to start a successful company. Mark Regan proves that completely wrong. Armed with just a rake, a bucket, and a $5 Craigslist ad, Mark turned a weekend Side hustle into a massive operation that consistently generates $50,000 a month. In this episode, Mark shares his raw Entrepreneurship journ...

Namoka transformed a struggling, permit-less hot dog cart into a legal, highly profitable mobile food empire that generates up to $100,000 in peak months. After the city confiscated the original equipment, Namoka refused to give up. Instead, she treated the setback as a brand new Startup and rebuilt the operation strictly by the book. In this episode, she reveals the unglamorous realities of her e...

Nick Avaria built and sold multiple agencies by leaning into strategic planning and one counterintuitive belief: the fastest way to grow profit isn't better tactics, it's paying your team above market. After leaving a $100 million industrial services company, Nick discovered that agencies thrive when founders charge premium prices to hire exceptional talent, completely removing themselves...

Ashley, the founder of My Healthy Soap, started her Cosmetics brand as a desperate late-night experiment in her kitchen. What began as a simple desire to find safer ingredients for her baby quickly evolved from a stressful farmer's market Side hustle into a massive $320,000-a-year operation. In this episode, Ashley breaks down how she went from mixing lye in thrift store pots to building a ful...

Ken Goodrich bought his father's struggling HVAC company, only to have the IRS seize everything and 30 employees quit overnight. Left with just $3,000 and two technicians, Ken had to learn how a company actually works. Today, he has bought and sold over 250 companies and achieved a high nine-figure exit. In this episode, Ken shares his ultimate playbook for Business buying and capitalizing on...

Jason Wong started his entrepreneurial journey at 16, when he managed to generated $250,000 in a single week by selling viral products like the "Holy Meme Bible." But after years of chasing trends in the volatile world of Dropshipping and Ecommerce, he decided to pivot away from the hype. Today, Jason is the founder of Packing Duck, a vertically integrated packaging company that is disru...

Alisa Sparks grew her home staging brand, Linden Creek, to $4 million in revenue and 20 locations by treating her passion like a math equation rather than a creative outlet. In this episode, Alisa warns that 50% of owners in Home Services are actually running "hobbies" because they lack clarity on their numbers. She breaks down exactly how to escape the hobbyist trap, revealing why &quot...

At 17 years old, Aaron Steed started a business with no trucks, no money, and no safety net. Today, Meathead Movers generates $20 million annually, employs 350 people, and has landed on the Inc. 5000 list for eight straight years. In this episode of UpFlip, Aaron reveals how he disrupted a "boring" industry by turning hustle into a visible competitive advantage. He explains why his mover...

Imagine being a broke college student delivering DoorDash orders just to pay rent. Now, imagine taking that same obsession with efficiency—shaving seconds off delivery times—and applying it to real estate. That is exactly how Josh Janus built a $15 million portfolio with hundreds of units in just three years. In this episode of UpFlip, Josh breaks down how he went from a $3,000 wholesale fee to ma...

How do you turn a beat-up cargo van and a funny name into a $300 million empire ? Nick Friedman, co-founder of College Hunks Hauling Junk & Moving , joins UpFlip to reveal the blueprint behind one of America’s most iconic service brands. From a summer side hustle to over 200 locations, Nick breaks down the exact systems used to survive the 2008 housing crash, COVID, and volatile markets. In th...