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
