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PODCAST

The UpFlip Podcast

The UpFlip podcast is where you get to unravel how great businesses are built, how they are run behind the scenes, and how their success can be replicated. We feed on the idea that no matter what the circumstances are, the American Dream is still just around the corner. With over 150+ videos and 50 million views on YouTube, UpFlip has ignited the spark that rekindles the fire of entrepreneurship in its ever-growing 700K+ audience. Through this podcast, we aim at sharing practical nuggets of gold and

business entrepreneurship

All Episodes

00:31:17

221. Self Storage Investing How She Makes...

The UpFlip Podcast ·

2026/01/12

Imagine making money while relaxing on a beach in Greece, not because you’re a crypto genius, but because you own metal boxes on a dirt lot. That is the reality for Bree Hartman, a former personal trainer who traded "trading time for dollars" for the high-margin world of Self-Storage Investing.In this episode of UpFlip, Bree breaks down how she built a portfolio of over 100,000 sq ft of storage space. She explains why self-storage crushes residential real estate (lower expenses, no

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00:30:57

220. The Tricks and Tips to a $170,000/month Mid-Term...

The UpFlip Podcast ·

2026/01/05

Imagine walking away from a $200k salary to bet on a gap in the real estate market. That’s exactly what Jesse Vasquez did. Today, his portfolio generates over $2.1 million annually by focusing on the "Mid-Term Rental" (MTR) strategy—a sweet spot between long-term leasing and high-turnover Airbnbs.In this episode of UpFlip, Jesse reveals how MTRs generate 3-5x the cash flow of traditional rentals. Whether you have zero properties or a full portfolio, Jesse breaks down how to secure

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00:25:30

219. How Faith Turned a Heart Attack Into a $5...

The UpFlip Podcast ·

2025/12/29

John Hill was lying in a hospital bed after surviving a massive heart attack when he faced a life-altering choice: give up, or stay and find a higher purpose. Choosing to stay, John walked away from his stable job with only one paycheck left, no safety net, and a yellow legal pad to map out a business idea that experts called "the worst model ever." He set out to clean up a dirty industry by doing the unthinkable—personally guaranteeing the work of contractors to protect homeowners.In this

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00:29:00

218. How this company scaled to $1M in revenue and...

The UpFlip Podcast ·

2025/12/22

Fred and Sherrod were top-tier corporate sales performers pulling in six-figure salaries before they realized that the local "dirty" businesses—like junk haulers and carpet cleaners—were actually out-earning them while enjoying significantly more freedom. Tired of the "gilded cage" of corporate America, this US Army veteran duo walked away from their Fortune 500 careers to build Accelerated Waste Solutions. Today, they’ve turned a borrowed pickup truck into a national system that

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00:26:18

217. How To Build a Purpose Driven Business That...

The UpFlip Podcast ·

2025/12/15

Ryan Emmons entered one of the most competitive and criticized industries on the planet—bottled water—with little more than a U-Haul and a vision. Going up against billion-dollar giants like Fiji and Smartwater, Ryan didn't just build another beverage brand; he built a mission. By betting everything on a "triple bottom line" philosophy—People, Planet, Profit—he proved that a purpose-driven company could disrupt a saturated market and command consumer loyalty in a way the big

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00:34:07

216. The Anatomy of a $35,000/month SaaS Company

The UpFlip Podcast ·

2025/12/08

Clay Lawrence built a generalist digital marketing agency to $17,000 a month, but quickly realized he had created a trap: he was exhausted, overworking, and constantly trading time for money on services ranging from drone footage to SEO. Desperate for a change, he took a massive financial risk—firing his clients and watching his revenue plummet to $4,500—to bet everything on a single, scalable idea that didn't require him to be the bottleneck.That bet was Review Harvest, a low-ticket SaaS

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00:28:53

215. 3 Entrepreneurial Lessons That Change Everything...

The UpFlip Podcast ·

2025/12/01

Eddie Hartman co-founded LegalZoom with a simple but radical idea: legal documents are just information, and information belongs online. Despite facing an industry of lawyers who wanted to sue the company out of existence, Eddie pushed forward to help launch one out of every four small businesses in California. Today, as a partner at Simon-Kucher, he advises global giants like Uber and Airbnb on pricing strategies, proving that the secret to success isn't just building things people want—it's

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00:24:04

214. Startup Lessons from a Founder Who Discovered a...

The UpFlip Podcast ·

2025/11/24

Teague Egan faced every founder’s nightmare: payroll was due, and a massive investment deal with General Motors was stalled. With his back against the wall, Teague sold his house for $2 million and wired the cash to his company just to stay alive. That "all-in" gamble paid off, securing the partnership and positioning EnergyX to revolutionize the global energy transition.It all started on a Bolivian salt flat, where a chance comment sparked an obsession with lithium. In this interview,

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00:30:41

213. How to Get Your First 10 Painting Clients Fast...

The UpFlip Podcast ·

2025/11/17

Richard Gould went from a high school dropout to the founder of a blue collar franchise with over 20 locations. After buying a business from his mentor and quadrupling sales, he took a massive risk: selling everything to move to a new state with no connections. There, he rebuilt his empire from scratch, proving his system works anywhere.In this episode, Richard breaks down exactly how to start a painting business with less than $1,000. He explains why simple marketing like door hangers and

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00:29:47

212. How to Turn a Simple Service Into a Scalable...

The UpFlip Podcast ·

2025/11/10

Michael Sutton was a university student looking to pay tuition when he and a buddy spotted an overlooked problem: dirty grills. With zero experience and just pure hustle, they started knocking on doors. After landing five sales on their very first day, they hit a critical snag—they had no idea how to actually clean a grill. That first job was an "eight-hour disaster," forcing them to learn on the fly.Instead of quitting, Michael turned that grueling summer job into Grill Hero, a rapidly

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00:33:28

211. The Founder Playbook to Grow Fast, Build...

The UpFlip Podcast ·

2025/11/03

John Sampogna co-founded his digital agency, Wondersauce, at just 26, with the ambition to take on the giants of Madison Avenue. He spent five years grinding, building a stellar reputation, and scaling his team from two to 100 employees. But as the operational weight of payroll, HR, and collections threatened to pull him under, he made a decision that shocks most founders: he sold the company he bled for.For most founders, that’s the end of the story. For John, it was just the beginning. He stayed

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00:28:17

210. How this 24-year-old built a $1.5M/year business

The UpFlip Podcast ·

2025/10/27

Chase Gallagher wasn't playing video games at 12. He was knocking on doors to build his lawn care hustle. A year later, he sold his dirt bike for a trailer. That relentless drive paid off: his side hustle has exploded into CMG Landscaping, a $1.5 million-a-year operation, with total ventures approaching $2 million annually.In this interview, Chase details the playbook he used to scale his home service business. He breaks down his crucial pivot: shifting from low-margin lawn mowing to

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00:27:48

209. Here are Recession Proof Small Business Ideas

The UpFlip Podcast ·

2025/10/20

Giuseppe Grammatico was living the life many dream of—a six-figure salary at JP Morgan. But with a five-hour daily commute and a baby on the way, he realized the "dream" was costing him the one thing that truly mattered: time with his family. He made the terrifying choice to quit his secure corporate job with no business idea, betting everything on a life of freedom. His search led him away from startups and into the world of franchising, where he discovered opportunities beyond just fast

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00:32:26

208. The Boring 8-figure Business Hiding in Plain Sight

The UpFlip Podcast ·

2025/10/13

Andrew went from a $13/hour manual labor job to a six-figure sales role at his corporate job. But decided to quit after a feud with a manager who called him “replaceable”. He then took a massive risk, liquidating his 401(k) to buy into his friend's tree-cutting side hustle. That gamble paid off, scaling the home services business into a powerhouse now earning over $180,000 a month with a near-zero marketing budget.In this episode, Andrew joins Ryan Atkinson to share the playbook for his business

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00:30:38

207. The "Boring" Business Idea that Prints Casfhlow

The UpFlip Podcast ·

2025/10/06

Dan Blaker was trapped in a sales job he despised while struggling to manage his mother's vacation rental with unreliable cleaners. Searching for an escape, he stumbled upon MaidThis, a cleaning franchise specializing in short-term rentals. With no entrepreneurial background, Dan took a huge risk, securing a personal loan with his mother's help to buy in and start his side hustle.The beginning was a grind of late-night training calls and weekend work. The real test came when he was

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00:32:27

206. "Just Ship It” The Philosophy to Start Your...

The UpFlip Podcast ·

2025/09/29

Ty McBride comes from a long line of builders, but his grandfather urged him to forge his own path. Ty initially chased success by landing massive historic preservation contracts, only to find himself running a high-stress, low-profit “train wreck.” A sudden pivot during the pandemic pushed him back to his local community, where listening to his neighbors revealed a massive, unsolved problem: wood rot. This discovery led him to build a new business around a specialized epoxy repair service, turning

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00:27:12

205. From Facebook Marketplace to $480K a Year in Car...

The UpFlip Podcast ·

2025/09/22

Aubrey Janik was stuck with a Jeep she didn’t like. When a friend mentioned renting his car on Turo, she listed it that same night. That impulse decision grew into a massive car-sharing business with a 34-vehicle, self-funded fleet that now generates up to $40,000 a month in revenue.What started as a side hustle became a lesson in smart asset acquisition. Aubrey mastered sourcing cars from Facebook Marketplace with a simple but brilliant strategy: buying reliable, depreciated vehicles below market

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00:36:25

204. The Boring Businesses that Print Cash

The UpFlip Podcast ·

2025/09/15

Imagine going from working warehouse shifts to keep your family afloat to owning a portfolio of over 140 rental units and multiple laundromats. That’s Brandon Turner's real-life story, and it’s one you have to hear. He found a secret most online gurus miss: while everyone’s chasing the same digital dreams, real wealth is hiding in 'boring businesses' with way less competition.In this chat with our host Ryan Atkinson, Brandon gets super specific on how he built his empire. He walks us

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00:32:59

203. Systems, Subcontractors, and Smart Marketing for...

The UpFlip Podcast ·

2025/09/08

Eric Barstow graduated with an economics degree, seemingly destined for Wall Street. Instead, he stuck with the painting business he started in college—a side hustle that was already generating $110,000 a year while he worked only five to ten hours a week. Realizing the massive opportunity and low competition in the home service space, Eric leaned in. Today, he is the co-founder of National Painting Group, projecting $35 million this year, and runs Painting Business Pro. And guess what? He barely

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00:35:07

202. Franchising vs Starting Your Own Business:...

The UpFlip Podcast ·

2025/09/01

Alex Smereczniak's entrepreneurial journey began in college, where he scaled a simple laundry service into a $300,000 a year business with a single, brilliant marketing hack. That early success was so powerful that he walked away from a prestigious corporate job after just 18 months, convinced the 9-to-5 was a broken system. His next venture led him into the world of franchising, where he uncovered its dark side: an industry filled with biased brokers and misaligned incentives. To fix this, he

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228 results

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