Episode Stack: https://stackl.ist/4tqYPeB

Steven Plappert closed Forecastr's Series A the day before his last payroll would have cleared the bank. Six weeks later, he's sleeping eight hours a night for the first time as a founder.

In this episode of Zero to Umm, Steven and I trace the full arc: failing his first company after three years, walking the Appalachian Trail from Georgia to Maine, meeting his co-founder Logan Burchett by accident at a CFO shop in Louisville, and building Forecastr through six years of round-to-round survival.

Key topics:

• Why curiosity, a greatness obsession, and a high tolerance for volatility pointed Steven toward entrepreneurship
• The FantasyHub shutdown that paid him $12,000 a year for two years — and the identity crisis that followed
• 2,000 miles on the Appalachian Trail and the idea that wouldn't stop nagging him while he walked
• The second-time founder playbook: why Steven never raised without a paycheck and never dropped below three months of runway
• Hell Week at Christmas 2020 — four people hand-migrating 100 Google Sheets models into the new product
• The Series A that died when Silicon Valley Bank did
• His Iron Man suit philosophy: why Forecastr is building for a human in the loop, not against one

Episode Stack: https://stackl.ist/3QEYaYe

Thomas Peham spent a decade building marketing engines for other people's companies — from a tiny PLG startup to a venture-backed company that raised $138M in funding. Then he noticed something that changed everything: ChatGPT was answering questions his clients used to win on Google, and nobody had a way to measure it.

In this episode, Thomas shares the full story behind Otterly AI — from the aha moment in his car to a Product Hunt launch with no pricing, a TechCrunch feature before Christmas, and scaling to 20,000 users in a single year without taking VC money.

Key topics:

• Growing up in Austria with no business background and stumbling into SEO through HTML hobby projects
• Building Usersnap's inbound engine from zero marketing budget to seven figures through content alone
• The moment he realized AI search was going to disrupt everything he'd spent years mastering
• Launching on Product Hunt with a "super scrappy" product and no pricing page
• Why 15% of website traffic now comes from AI agents — and what that means for marketers
• Bootstrapping a 17-person company in a category that didn't exist two years ago

Episode Stack: https://stackl.ist/4sSOZBB

Andrew Boos is the founder of Darwinian Ventures, a fractional sales advisory firm that builds go-to-market teams for early-stage B2B startups. He's also quietly investing in his own clients from profit, not a fund.

Before Darwinian, Andrew had a profitable exit at 24 from a startup that began as an ad exchange for China (yes, really), fell into post-exit depression nobody wanted to hear about, learned enterprise sales under a CRO with a $4.2 billion annual quota at a Sutter Hill incubation, blew his exit money trying to launch a quantitative hedge fund, and started freelancing to pay rent when law firms came knocking.

We talk about why a linear path to entrepreneurship is a privilege, what happens when your North Star disappears after an exit, how he built Darwinian from a solo 1099 gig into an embedded sales team that's worked with 100+ startups, and why he's now writing small checks into companies where he can see product-market fit before the founders do.