Startup Stories from the Treehouse

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 th...

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...

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...

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...

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 fou...

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 sea...

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 f...

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...