What happens when a self-described "bad student" from Michigan decides to bootstrap a business during the 2009 financial crisis with nothing but $15,000 and a whole lot of stubborn determination?
Carson Poppenger, founder and CEO of Squeeze, turned that exact scenario into a national lead conversion company that now employs over 500 people across multiple states. His journey from Target supervisor to Utah 100 honoree (four years running) proves that sometimes being stubborn is exactly the right strategy.
Carson's path wasn't traditional. He jumped straight into business classes, skipped the typical undergrad route, and discovered his passion for profit margins while sneaking into Target's back office to study product data. After cutting his teeth at Prosper alongside future industry leaders, he spotted a massive gap in lead conversion and follow-up that became the foundation of Squeeze.
From bootstrapping with credit cards to bringing on an equal equity partner (against everyone's advice) to eventually buying him out, Carson's story reveals the real challenges of scaling a service business while maintaining client relationships that turn into evangelists.
Today, Squeeze serves top-tier mortgage, healthcare, and home service brands, delivering results that often outperform internal teams by 4x. But Carson's also preparing for the future with AI innovations like Peel Voice, which analyzes sales calls for customer sentiment and agent performance, proving that even established businesses need to stay ahead of the technology curve.What You'll Learn:
- [06:25] The Target back office breakthrough: How Carson's obsession with sneaking into Target's office to study profit margins on different product categories revealed his true passion for business profitability and set the foundation for his entrepreneurial journey
- [07:15] The 20% revenue solution that sparked Squeeze: Carson reveals how he built a lead conversion solution at Prosper that became 20% of company revenue and why spotting this gap in the market became his "aha moment" for starting his own business
- [10:00] The contrarian 2009 launch strategy: Why Carson chose to bootstrap during the financial crisis instead of seeking investors, including the advice that changed everything: "Don't waste your time entertaining PE people; just go out and sell"
- [14:23] The survival mindset: Carson's raw honesty about the terrifying lows of entrepreneurship, the friends who suggested he try something different, and how stubborn persistence became his secret weapon through the darkest moments
- [18:40] The 50/50 partnership everyone said not to do: The controversial equal equity split that "everyone advised against," how it led to 8x growth over 4 years, and Carson's eventual buyout strategy that proved the doubters wrong
- [29:02] AI disruption strategy from the trenches: Carson's insider perspective on why most AI voice startups won't succeed with enterprise clients, plus how Squeeze is building Peel Voice to analyze sales calls and prepare for the technology shift
- [33:14] Why Utah made the difference: The specific ways Utah's business-friendly environment, from regulatory simplicity to collaborative culture, enabled growth that Carson believes wouldn't have been possible in other states
Whether you're bootstrapping your first business, scaling a service company, or wondering how to prepare for AI disruption while staying human-centered, Carson shares practical insights from 15 years of building relationships, solving problems, and proving doubters wrong.Connect with Carson and Squeeze:
- Website: gosqueeze.com
- AI Technology: peelvoice.com
- LinkedIn: Carson Poppenger (https://www.linkedin.com/in/carsonpoppenger/)
- Utah 100 Honoree: 2021, 2022, 2023, 2024 (#43)
- Inc 5000 award: 4x, 2022, 2023, 2024, 2025
Want to Connect?
[email protected][email protected]Meet the dedicated members of our podcast committee who curate content, organize interviews, and ensure the success of The MountainWest Capital Network Podcast “Welcome to the Winners’ Circle.”
Cheri Waldron, MWCN Executive Director
Jason Roberts, MWCN Podcast Chair and Managing Director, Protiviti
Kevin Jessop, MWCN President and Chief Marketing Officer, IMA
Garit Lawson, MWCN Podcast Vice-Chair, Managing Director, Forbes Partners
Zachary Reed, MWCN Podcast Producer, Senior Associate, PwC LLP
Katie Brown, MWCN Business Operations Specialist
The LaunchPod Media Team.
