Startup Stories from the Treehouse

Hosted by Todd Gagne

Business Entrepreneurship

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Aug 2026

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About the show

Welcome to Startup Stories from the Treehouse, where we bring you the most captivating tales of entrepreneurship. Each episode is a new adventure, featuring entrepreneurs who turned their dreams into reality. Whether you're a seasoned entrepreneur or just getting your feet wet, 'Startup Stories from the Treehouse' is your inspiration to build, innovate, and soar. Tune in, and let's start the adventure together!

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60 recent

August 27, 202651 min

Two Combat Tours, Zero Panic Attacks. Two Years in Business, Two.

You can white-knuckle your way through almost anything, until the day it stops working. In this episode, Todd Gagne sits down with Sean Patton, a West Point graduate and Green Beret who spent two years in combat without a single panic attack, then had two in his first years as a founder. Open sores, appendicitis, bankruptcy, driving Uber. They get into why grit gets you to the fight but won't tell you who you are when you lose one. Sean talks about the gap between vision and reality that never closes, the difference between being kind and being nice, and hiring for want instead of talent. He shares the priority order he now protects, and why walking straight toward the worst case tends to shrink it. A calm, honest look at the inner work founders skip until it costs them everything. Ready to build without burning out? Apply to the Wildfire Labs accelerator at wildfirelabs.io. Subscribe to the Wildfire Labs Substack for podcast summaries and more insight on building a tech startup.

August 13, 202650 min

What David Woodbury Learned by Hitting the Wall

David Woodbury built seven companies and hit a wall so hard he walked away for three years. In this episode, he unpacks what burnout actually looks like—decision fatigue, not drama—and the bike that taught him you can't outwork the grind. We talk niching (the mistake that cost him a market, the pivot that borrowed $20M in marketing budget), why domain expertise beats AI, and the question every founder should ask before starting: do you actually like this, or are you proving something? Now he's back, building Grow Army to give early-stage founders the framework he didn't have. Hit play for one of the most honest conversations we've recorded. Ready to build without burning out? Apply to the Wildfire Labs accelerator at wildfirelabs.io. Subscribe to the Wildfire Labs Substack for podcast summaries and more insight on building a tech startup.

July 30, 202650 min

The Month Google Spent $4

The $4 Month That Revealed Google's Death — And What Founders Must Do Next In August 2024, Jon Mest discovered Google had spent just $4 of his thousands-dollar monthly ad budget. Nothing was broken—Google's AI overview was simply answering his customers' questions for free, above his #1 ranking and his ads. Instead of complaining, Jon treated it as confirmation that discovery was shifting from search engines (ten blue links) to answer engines (ChatGPT, Gemini) that choose winners for you. He built in public, validated with customers, and launched ChatRank. The new game rewards credibility over budget: third-party mentions from niche authorities, organic social signals on Reddit and Quora, and genuine reviews. One tiny cybersecurity firm outranked Vanta and Drata within a week using this playbook. Ready to see where you stand? Open a temporary ChatGPT chat, ask who's best at what you do, and if you're missing—ask why. Then close the gaps. Subscribe to Wildfire Labs for more founder insights. Subscribe to the Wildfire Labs Substack for podcast summaries and more insight on building a tech startup.

July 16, 202650 min

The Word That Kills Startups Is "Interesting"

Why "Pain Points" Don't Close Deals — And What Actually Does Sales expert Rob Snyder learned the hard way that pain points don't predict purchases. After two years of failure followed by explosive growth ($0 to $4M ARR), he discovered the real driver: pull. Prospects may rate their pain 10/10 in discovery calls, yet never buy—because pain is everywhere, while active priorities are rare. His PULL framework identifies buyers with a P roject underway, that's U navoidable, a L ist of options tried, and L imitations in those options. When all four exist, customers rip products from your hands. A QA startup proved it: after hearing a CTO say "I just want QA off my plate," they ditched demos, raised prices 40x, and closed deals in weeks. The lesson? Stop manufacturing demand—find people already trying to solve the problem. Ready to find your pull? Grab Rob Snyder's new book, The Power of Pull , out July 7, and study your fastest-closing customers today. Subscribe to the Wildfire Labs Substack for podcast summaries and more insight on building a tech startup.

July 2, 202650 min

Endurance Beats Speed

Eric McDonald spent nineteen years building DocuTap, a healthcare tech company he started by writing code in his South Dakota basement, eventually reaching a $1.25 billion valuation and exit in 2022. His story rejects the move-fast startup gospel in favor of endurance. His key lessons: pick a vertical that grows underneath you (he chose exploding urgent care, where clients expanded on their own); get to cash-flow break-even faster than feels comfortable, since runway-dependence hands control to investors; extend trust to new hires instantly while openly owning your weaknesses; recognize that your best ideas come from listening, not inventing; reinvent yourself at every stage of growth; and integrate small acquisitions as seriously as big ones. Most importantly, anchor your identity outside the company—he lived in a tent for three months after stepping down to rediscover who he was beneath the title. Want the full story? Listen to the complete podcast episode and connect with Eric on LinkedIn. Subscribe to the Wildfire Labs Substack for podcast summaries and more insight on building a tech startup.

June 18, 202617 min

The Last Paycheck

In this episode, I’m on the other side of the mic as Jared Tiefenthaler, CEO of Signed Up Sports, interviews me about my toughest founder experience—shutting down my first startup in ‘90s Rapid City. I share the raw realities: sleeping on a couch, biking to the office, and delivering the hardest news—issuing the team’s last paycheck. The story dives into the real test every founder faces: authenticity under pressure. When faced with failure, I learned the importance of honesty and transparency, even when it hurts. Those moments, more than any pitch or launch, built trust that lasted for years—many from that team followed me in later ventures. These lessons shaped nearly two decades at Concur and still guide my coaching and leadership today. Ready to hear the full story and discover what separates good founders from great ones? Listen to this week’s episode of Startup Stories from the Treehouse! Subscribe to the Wildfire Labs Substack for podcast summaries and more insight on building a tech startup.

June 4, 202655 min

Direction Beats Effort

You're working harder than ever, and the returns keep shrinking. More ads, more hires, more campaigns—and somehow the needle barely moves. In this episode, Todd sits down with Pete Steege, founder of B2B Clarity and author of On Purpose and Radical Clarity , to unpack why effort stopped being the constraint and direction took its place. They talk about the "accidental CEO" problem—the technical founder who built the product, watched customers show up, and then looked up one day running a company nobody handed them a manual for. Pete walks through his CMP framework, the difference between a target customer and a bullseye, and why most marketing problems are really clarity problems in disguise. Todd pushes back in a few places too, especially on AI and founder authenticity. It's a grounded conversation about what happens when the old moat stops working and the honest question is what you've been avoiding. Subscribe to the Wildfire Labs Substack for podcast summaries and more insight on building a tech startup.

May 21, 202652 min

The CPO Who Started Again

You talked to a few customers. They nodded along. Said they'd use it. You walked away validated. What you actually got was a polite confirmation of what you already believed. In this episode, Todd Gagne sits down with AG Lambert, a thirty-year product veteran from Autodesk, Concur, and Navex, who recently walked away from the CPO title to build alone. They talk about the difference between a conversation and a structured interview, and why one reinforces your bias while the other tests it. AG shares how he grew Concur's invoice product from six million to over a hundred million in ARR, starting with the unglamorous work of asking customers what was broken. They get into what AI actually changes in product work, what it doesn't, and the quieter cost of building solo, the loss of people who push back on your ideas before they become bad ones. A grounded conversation about doing the work most founders skip. Subscribe to the Wildfire Labs Substack for podcast summaries and more insight on building a tech startup.

May 7, 202645 min

Every Investor Says They Bet on People— Almost None of Them Can Prove It

In a recent Startup Stories from the Treehouse episode, Todd Gagne sits down with Logan Yonavjak, co-founder and CEO of the Founder Readiness Institute, to tackle why startups fail — and it's rarely the idea. It's the people. Logan draws on nearly two decades in impact investing to reveal that leadership gaps, co-founder conflicts, and poor team dynamics are the real culprits behind stalled companies. Her research-backed assessment evaluates founders across six constructs, including coachability, emotional intelligence, and strategic complexity. Key insights include recognizing hidden leadership biases, understanding that true coachability means releasing your past identity, pitching your team as a functioning unit rather than a résumé collection, and treating the co-founder relationship with the same care as a marriage. The bottom line: your leadership capacity is your company's infrastructure. Understanding your patterns early is the competitive edge most founders overlook. Listen now wherever you get your podcasts. Subscribe to the Wildfire Labs Substack for podcast summaries and more insight on building a tech startup.

April 23, 202653 min

How Donato Callahan Built Bright Investor

At twenty-one, Donato Callahan was buying real estate, working for the Department of Defense, and frustrated by how broken deal analysis was. So he built BrightInvestor. By twenty-five, he had several hundred doors and a growing SaaS platform. Three ideas from our conversation stand out. First, his $500 test — he only builds AI features customers will actually pay for, not ones that sound cool. Second, his concept of the "vertically integrated worker" — stacking complementary skills within one ecosystem instead of chasing disconnected side hustles. Third, his take on AI's real limit: it gets you to third base, but domain expertise is what scores the run. Beginners who skip the learning curve get stuck. Experts use the same tools and widen the gap. His default setting? Don't ask why — ask why not . Listen to the full episode of Startup Stories from the Treehouse to hear the rest. Subscribe to the Wildfire Labs Substack for podcast summaries and more insight on building a tech startup.