Startup Stories from the Treehouse

Hosted by Todd Gagne

Business Entrepreneurship

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Oct 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

October 22, 202648 min

The Prices Were Public the Whole Time

There's data in your industry everybody treats as unknowable. The real prices, the real numbers. It's not actually secret. It's just scattered, and nobody's bothered to pull it together. In this episode, Todd talks with Brennan Holloway and Tyler Olson of The Journeyman, who found that wildland fire pricing—the bids that decide whether your phone rings when a fire breaks out—was public the whole time. It just lived across seven thousand Forest Service PDFs, filed by region and resource type, with no way to connect them. Brennan, who isn't an engineer, pulled all of it in about a day with an AI tool and built the board that shows where every competitor sits. Todd gets into why the edge belongs to the domain expert, not the model, and why that advantage has a shelf life. What changed wasn't the data. It was the cost of assembling it. Subscribe to the Wildfire Labs Substack for podcast summaries and more insight on building a tech startup.

October 8, 202650 min

He Thought His Company Did $1M. It Did $600K.

You trust the numbers you built yourself. The spreadsheet from year one, the revenue figure you calculate the same way every Monday. You made them, so you never reopen them. In this episode, Todd sits down with fractional CFO Anthony Nitsos, who once found a founder reporting a million in ARR that was actually forty percent smaller—contracts signed at a hundred thousand, invoiced at sixty. From there they get into why your chart of accounts is probably set up for taxes instead of running the business, how finance ends up finding out last, and a simple test: take what works at five million in revenue, add a zero, and ask whether it still holds. Anthony's line stays with you—you can't spend net income. The hardest box to open is the one in your own handwriting. Subscribe to the Wildfire Labs Substack for podcast summaries and more insight on building a tech startup.

September 24, 202655 min

Validation Isn’t Growth

Your traction looks like proof. Thirty paying customers, a Google grant, a top European accelerator. Most founders would read that as a signal to keep pushing. Vitalii Sydorenko walked away from exactly that. In this episode, Todd talks with him about why. Vitalii built his first company at twenty-two with no funding and grew it into the market leader in his country, with McDonald's and Samsung on the client list. Then he built a second the "right" way and watched it churn out from under him. Three ideas from the conversation: why validation isn't growth, the customer who kept asking for the slow manual report over his faster platform, and why the "last ten percent" is usually the first ninety. Also, why his studio turns down money it doesn't believe in. The idea wasn't the thing he got wrong. Talking to customers, then quietly stopping, was. Subscribe to the Wildfire Labs Substack for podcast summaries and more insight on building a tech startup.

September 10, 202650 min

You Don’t Have a Pitch Deck Problem. You Have a Strategy Problem.

Your pitch deck isn't landing, and you're convinced the problem is the slides. A better template, a slicker designer, tighter animations. Meredith Clause has torn down hundreds of decks, and she says the problem almost never lives there. In this episode, Todd talks with Meredith about why the deck is the strategic work, not the chore you finish before it. They get into the problem slide that says "healthcare is broken" when it should name one specific, under-the-radar pain. Why founders cast themselves as Luke Skywalker when the investor wants to be the hero, and you're Obi-Wan. And why going narrow feels like loss but is actually where traction lives. Her approach has helped founders raise more than $250 million. It's hard to read the label from inside the bottle. Sometimes the fix isn't your product. It's the way you're telling it. Subscribe to the Wildfire Labs Substack for podcast summaries and more insight on building a tech startup.

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.

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