Here’s a scene your business school professor never described: You’re sneaking into your employer’s back office during breaks, frantically studying profit margins on housewares and luggage while your actual job involves managing people on a retail floor. Your coworkers think you’re taking long bathroom breaks, but you’re actually getting a masterclass in what makes businesses tick.

For Carson Poppenger, those moments of curiosity at Target became the foundation of Squeeze: a lead conversion powerhouse that now employs over 500 people and generates millions in revenue annually.

But here’s the kicker: Carson describes himself as a “bad student” who got Cs and Ds in high school. His secret weapon? Being “too dumb to quit” when everyone else said it was time to try something different.

In our latest MountainWest Capital Network Podcast episode, Carson reveals how he bootstrapped Squeeze from $15,000 and credit card debt during the 2009 financial crisis into one of Utah’s fastest-growing companies. 

His story proves that sometimes the worst economic conditions create the best business opportunities, as long as you’re stubborn enough to outlast the fear.

The Back Office Obsession That Started Everything

Most Target employees avoided extra work, but Carson sought it out.

“Every time I could, I would sneak into the back office,” he admits with a laugh. “They had a few computers back then. I’d jump on the computer and I’m studying the margins on different product categories.”

While other college students were cramming for humanities tests (which Carson “hated”), he was discovering his true passion: understanding what drives business profitability. That obsession with numbers and systems would become the cornerstone of everything he built.

The irony? This “bad student” was getting a better business education in Target’s back office than most MBA programs provide. He just didn’t know it yet.

The $15,000 Bet Against Economic Disaster

When the 2008 financial crisis hit and the economy was still reeling in 2009, most people were looking for job security. Carson saw opportunity.

“I kind of thought to myself at that time, I probably can’t go out and get a better opportunity than I have right now, and so this will give me time to work on this,” he explains. With $15,000 to his name and a credit card strategy that would make financial advisors cringe, Carson launched Squeeze.

His contrarian approach came from advice that went against everything business schools teach: “Don’t waste your time entertaining all the PE people. Just go out and sell and your results will produce.”

Ten years of grinding followed. Ten years of what Carson calls “building brick by brick to get that next client.” No venture capital. No safety net. Just results and the kind of stubborn persistence that makes people either incredibly successful or completely broke.

Carson chose success.

The Emotional Rollercoaster Nobody Talks About

Here’s what successful entrepreneurs don’t tell you about the early years: it’s an emotional nightmare.

“You have the highest highs and the lowest lows,” Carson reveals. “I just remember those moments where I’m in my car and I’m just driving along. I’m like, yes, this great thing happened… And then you have those moments where you’re like, I can’t even tell anybody about this. What am I going to do?”

Friends started suggesting maybe it was time to try something different. Maybe the business thing wasn’t working out. Maybe he should get a “real job.”

Carson’s response? “I always kind of say, maybe I was just too dumb to quit.”

That stubbornness became his superpower. When logic said quit, Carson doubled down. When fear said retreat, he pushed forward. When conventional wisdom said play it safe, he made the boldest moves of his career.

The Partnership Decision That Shocked Everyone

After 10 years of solo bootstrapping, Carson made a move in 2019 that had his advisors questioning his sanity: he gave away 50% of his company to Alejandro Vargas.

“Everyone’s told me not to do this much equity in a partnership,” Carson admits. “We ended up doing an equal split on our ownership, which was something that everyone always advised me not to do.”

Business 101 says maintain control. Keep the majority stake. Never give up decision-making power.

Carson ignored Business 101.

The result? Eight times growth over four years. Squeeze exploded from a solid local business to a national powerhouse with operations across four states.

But the story gets better. Carson eventually bought out Vargas, proving that sometimes the moves everyone says not to make are exactly the ones that change everything in the best way.

“Fast forward over a year later, I tell people all the time, I’m so thankful that I’ve been able to make that work,” he reflects. 

Translation: Carson bet on himself, won, and now has the majority of a company worth exponentially more than when he gave away half.

The AI Strategy While Competitors Are Still Figuring Out Email

While most business owners are still debating whether AI is real or hype, Carson is already three steps ahead. Squeeze has developed Peel Voice, an AI system that analyzes sales calls for customer sentiment and agent performance.

The problem it solves is massive: traditional sales reporting tells you almost nothing about what actually happens on customer calls.

“You only can get what an agent can share about a call,” Carson explains. “Maybe they say the person was not interested because of some reason, and then they select an option, and that goes in the CRM and that’s it. That’s all you know about the customer and the call.”

Carson’s solution? Let AI listen to every call, analyze customer emotions, evaluate agent performance, and identify patterns that humans miss. It’s like having a sales manager who never sleeps and remembers every conversation.

His competitive advantage is understanding enterprise sales at a level most AI startups never reach. “There’s probably a thousand startups working on AI voice right now,” he notes, “and most of them have really tiny clients.”

Squeeze works with the big players. When AI fully arrives, they’ll be ready while competitors are still learning the basics.

The Utah Secret Weapon

Carson’s success is about persistence and about picking the right place to be persistent.

Moving from Michigan to Utah at 20 without knowing anyone turned out to be one of his smartest decisions. Utah’s business-friendly environment, collaborative culture, and regulatory sanity created conditions for growth that might not have been possible elsewhere.

“I don’t know that I could have done what I did for the bootstrap,” Carson reflects when discussing other states’ business climates. Complex regulations, high minimum wages, and bureaucratic overhead can kill bootstrapped businesses before they have a chance to prove themselves.

Utah provided the opposite: a supportive ecosystem where businesses can focus on serving customers instead of navigating regulatory mazes.

The collaborative culture matters too. Carson mentions leaders like Ryan Westwood who “would take my phone call if I called him right now, and he’s been that way for 10 years.” That’s not normal in most business environments. In Utah, it’s standard.

The Family Partnership That Changed Everything

Behind every successful entrepreneur is someone who believes in the dream when logic says run. For Carson, that person is his wife, Amy.

When Carson started Squeeze, Amy was managing three daughters under eight while working as a developer at Nu Skin. She had the technical skills Carson lacked and the left-brain thinking to balance his right-brain creativity.

By 2015, when their kids were in school, Amy joined Squeeze full-time. She brought systems thinking, technical expertise, and the kind of tough questions that prevent expensive mistakes.

“She’s that person I can talk to about things,” Carson explains. “She’s a good decision maker. She has insight. She digs on problems and looks at data and things like that. And then she often asks the tough questions that either people aren’t sure about or don’t want to ask.”

Amy now operates in what Carson calls a “semi-retirement role,” coming and going as she wants while staying deeply involved in strategic decisions. It’s the kind of work-life integration most entrepreneurs dream about but few achieve.

The 4X Results That Built a Reputation

Today, Squeeze consistently delivers results that outperform clients’ internal teams by 4X. That’s not marketing hyperbole; it’s the mathematical reality that built their reputation and drives their viral growth.

“Our clients that we worked with 10 years ago, they’ve ended up at other companies doing the same thing. And then that’s turned into new clients and new opportunities for us,” Carson explains.

This evangelical client base has opened doors in insurance, mortgage, healthcare, technology, and home services. When you deliver 4X results, customers become salespeople.

The Lessons That Actually Matter

Carson’s journey from Target supervisor to leading a 500-person company offers insights that business schools don’t teach:

  • Curiosity beats credentials. Carson’s obsession with profit margins taught him more about business than his formal education. Follow what genuinely interests you, not what looks impressive on LinkedIn.
  • Crisis creates opportunity. Starting during the 2009 recession forced Carson to build real fundamentals instead of relying on easy money and growth-at-any-cost strategies.
  • Ignore conventional wisdom when it matters. Carson’s biggest wins came from decisions advisors opposed: launching during a recession, giving away 50% equity, and focusing on results instead of investor fundraising.
  • Pick your environment carefully. Moving to Utah provided regulatory, cultural, and network advantages that accelerated growth. Geography matters more than most entrepreneurs realize.
  • Prepare for tomorrow while excelling today. Building AI capabilities while maintaining service excellence positions Squeeze to capture market share as technology evolves.
  • Stubborn persistence beats smart strategy. Sometimes the best business plan is simply refusing to quit when logic says you should.

From stealing moments in Target’s back office to building a company that outperforms billion-dollar competitors, Carson’s story proves that success doesn’t require perfect conditions, elite credentials, or venture capital validation.

Sometimes it just requires being too dumb to quit.

Ready to hear Carson’s complete story? Listen to his full interview on the MountainWest Capital Network Podcast, where he shares the unfiltered details of bootstrap survival, partnership strategy, AI preparation, and why Utah’s business environment makes the impossible possible.

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