Startup Stories from the Treehouse

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);...

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: authenti...

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 fo...

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 conve...

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 compan...

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. Se...

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 fe...

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. Rememb...

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...

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...

Many startups waste marketing budgets due to unclear messaging and a fuzzy Ideal Customer Profile (ICP), not poor execution. Kae Kronthaler-Williams, a veteran marketing executive, advises founders to nail messaging, niche their focus, and build foundational infrastructure before scaling ad spend. Her 90-day plan: clarify messaging through customer interviews, validate ICP with targeted outreach,...

In this episode of Startup Stories from the Treehouse, Andy Sitison of Share More Stories shares hard-earned lessons from transitioning out of systems integration into building an AI-driven company. His core insight: surveys optimize answers, not understanding. By focusing on why customers behave the way they do—and designing for candor—founders can uncover motivations that drive real differentiat...

Since launching their podcast, Mike and the author have published 54 episodes, evolving from uncertain beginnings to delivering sharp, relevant insights for founders. Season three saw a major shift: 90% of guests were inbound, prompting growth in interviewing skills and richer conversations on AI, product management, and capital trends. Consistency in publishing proved crucial, while analytics sho...

In this end-of-year bookend episode, co-founders Todd Gagne and Mike Vetter of Wildfire Labs recap the key themes and trends they've observed with founders in their program over the past year. They dive deep into the rising necessity of deep domain expertise for founders, sharing compelling examples like AgSense (FinTech for ranching) and The Journeyman (wildland firefighting). The conversation ex...

Ryan Rosett, CEO of Credibly, shares how he built a thriving fintech without relying on venture capital, emphasizing that culture and transparency outlast quick funding. By bootstrapping through crises, leveraging modular microservices, and blending human expertise with AI, Credibly processes millions in loans rapidly and securely. Their hybrid in-office culture fosters innovation and knowledge sh...

This article distills key lessons for founders in product management, emphasizing the critical role of achieving product-market fit (PMF)—measured by whether at least 40% of users would “fight to keep” your product. Founders must prioritize deep customer engagement, not just feature delivery, and create structures (like recurring customer calls) to maintain user closeness. Success demands both str...

In "The Funding Framework: Secure Startup Funding With Confidence," Vijay Rajendran reveals that most founders approach fundraising backward—blasting pitch decks to countless investors rather than targeting those with a true fit. He advocates treating fundraising like enterprise sales: build relationships before you need capital, prioritize quality over quantity, and manage the process systematica...

Another week, another newsletter you feel obligated to ship. It’s supposed to help, but it often reads like a status update no one asked for. In this episode, Todd Gagne sits with Banks Benitez to reframe the founder newsletter as a product, not an email. The core insight: trust is the scarce resource, and your newsletter should solve a specific problem for a narrowly defined reader. They dig into...

Founders still build first and validate later—wasting years and capital. The real bottleneck isn’t knowledge; it’s disciplined execution. Treat validation like fitness: consistency beats spurts. Run strict gates before you write code: deep customer interviews, design mockups, then the 50% Rule—if half of interviewees won’t commit to a free beta, stop. Run the beta, then convert over 50% to paid. T...

Founders obsess over product-market fit, but the real determinant of a startup's success is the co-founder relationship. While partners focus on operational tasks, they often ignore the crucial psychological dynamics, leading to "emotional debt"—unspoken frustrations that compound and threaten the business during high-stress moments. You can't solve relationship issues with operational fixes. Succ...

Early-stage SaaS founders win by narrowing focus, starting marketing early, and building trust. Niche down to a specific ICP so your messaging speaks to real pain (e.g., third-shift hiring in manufacturing). Don’t wait for product readiness—begin 1–2 years ahead with thought leadership and top-of-funnel content so buyers know you before launch. Craft a unique perspective: map ICP challenges, use t...

Retaining customers is your fastest path to revenue, and AI can supercharge it. Ram Ganesan, CEO of Kaboom.ai, saw that most CRMs optimize for new pipeline, not existing relationships. Kaboom flips that: it maps relationship networks, mines unstructured data (emails, notes, earnings calls), and proactively nudges account managers—“It’s time to meet; this RFP decision is near”—boosting both rookies...

William Welser IV’s conversation with Todd Gagne spotlights a human-centered approach to AI and product building. His non-linear path—military, engineering, RAND, and founding LOTIC—centers on helping people. LOTIC flips the data model: it uses spoken stories as rich, owned-by-user data, secured with advanced encryption, and analyzed by the “Wisdom Engine” for personalized insights. Key takeaways...

Most communities aiming to replicate Silicon Valley overlook the essential foundation for entrepreneurial success: healthy ecosystems . In a conversation with Alfredo Mathew, founder of ESO Ventures, we explored the gaps in ecosystem building and solutions to empower entrepreneurs. Alfredo emphasizes that ecosystems must prioritize founders with skin in the game , supported by public, private, and...

At 18, Chris Brisson’s journey began with a simple desire for new Mustang rims, but it evolved into a lesson in business arbitrage when he resold them for a profit. Years later, facing financial hardship, Chris turned to eBay, sparking his entrepreneurial mindset. He learned by solving problems hands-on, embracing continuous improvement and documenting everything. Chris’s companies—like Salesmsg—f...