Startup Stories from the Treehouse

Hosted by Todd Gagne

Business Entrepreneurship

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Jul 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

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.

April 9, 202651 min

How a Serial Entrepreneur Built a News Product by Ignoring Everything Big Media Does

Kira Shishkin, founder of Informed.now, built a news product designed to be used for just thirty seconds a day—five bullet points, no images, no feeds. On a recent episode of Startup Stories from the Treehouse, he shared the principles behind this approach. His core lessons: obsess over the problem your customers share, not their demographics. Force a "Day One Hypothesis" and iterate from real feedback rather than waiting for certainty. Use Minimum Viable Information to protect decision-making speed. Make advisors useful by sharing written memos instead of open-ended questions. Trace news and industry information back to primary sources. And narrow your appeal deliberately—filtering out misaligned users upfront saves more than converting them ever will. Unexpected users like farmers and Uber drivers validated the product's real market: anyone who wants to feel informed but hates the news cycle. Listen to the full episode on Startup Stories from the Treehouse and try the product at informed.now. Subscribe to the Wildfire Labs Substack for podcast summaries and more insight on building a tech startup.

March 26, 202654 min

Revenue First, Perfect Later

Technical founders often overbuild in isolation, polishing products no one has validated. Adam Link — three-time founder, Coinbase IPO alum, angel investor, and now head of Fireweed Capital — learned that revenue, not perfection, creates opportunity. Ship early. Let it be imperfect. Sales isn’t a dark art; it’s debugging human problems. Identify the pain, confirm it exists, and offer a fix. Remember the “3% rule”: only a small fraction of your market is ready to buy today — focus on them. Beware the “dangerous middle,” where too much runway kills urgency. Revenue pressure drives clarity. Investors don’t just fund products; they fund competent, coachable founders who understand their numbers and have learned from failure. And in the AI era, prototypes beat pitch decks — execution speed is the new advantage. Above all, build from financial stability so you can take smart risks. CTA: Stop polishing. Ship something this week, talk to ten real users, and let the market shape what you build. Subscribe to the Wildfire Labs Substack for podcast summaries and more insight on building a tech startup.

March 12, 202647 min

The Hidden Superpower Early Founders Overlook: Why Your Message Matters More Than Your Tools

Founders often blame cold outreach when it fails, but Justin Rashidi (SeedEx) argues the real problem is the message, not the channel. Outbound still works when it’s specific and distinct: name a clear pain point and ask a simple “want to solve this, yes or no?” instead of over-personalized fluff. A major blocker is the “vocabulary problem”—different roles and company types describe the same issue in different words. The fix is doing 10–15 listening-heavy conversations, then using AI on call transcripts to surface recurring terms, objections, and winning phrasing. With message clarity, channels like LinkedIn conversation ads, selective gifting, Google Ads, and conferences can perform, but outbound must run alongside inbound to target the accounts you want. On AI adoption, most companies overclaim and under-integrate; start with small automations. He also recommends hiring a recruiter earlier, valuing “disagreeable” truth-tellers, and pushing sales first while ops trails by 30–60 days. If this was useful, like, share, and subscribe. Subscribe to the Wildfire Labs Substack for podcast summaries and more insight on building a tech startup.

February 26, 20261 hr 3 min

The Four Pillars of a High-Performance Startup: Lessons from an Operator Who’s Scaled Companies from $4M to $350M

Startup veteran Tim Butler, founder of GrowthFire, reveals the four pillars behind successful startups: people, product-market fit, go-to-market strategy, and culture. He urges founders to treat hiring as foundational—use scorecards to define roles, hire for qualities like passion and coachability, and create a culture where learning from failure is safe. Tim stresses the importance of validating demand before building any product—real customer commitments are crucial proof of value. Go-to-market execution, he argues, is more vital than product perfection, especially as AI transforms sales and marketing. Finally, culture isn’t about posters, it’s about behaviors, rewards, and consistent leadership. Tim’s advice: hire A-players, validate ruthlessly, sell to how customers buy rather than how you want to sell, and fiercely protect your company culture.Want to hear the full conversation and dive deeper? Listen to the episode on Startup Stories from the Treehouse, and learn more at growthfire.com. Subscribe to the Wildfire Labs Substack for podcast summaries and more insight on building a tech startup.