

Escaping the Sunk-Cost Trap: When to Pivot, Quit, or Double Down
Founders don’t usually get stuck because they lack ideas. They get stuck because they’ve invested too much to admit something isn’t working: time, money, identity, team momentum, customer expectations. That’s the sunk-cost mindset and it quietly turns smart people into stubborn decision-makers.
In this talk, Lonny James shares a founder’s perspective on recognizing when a change is needed, even when you’ve already poured a lot into the current path. Lonny is a founder, operator, and coach who built his last company from a side-hustle into a $30M+ business with 45 employees, and later made the call to reset and exit.
Today, he helps entrepreneurs build companies that are scalable, sellable, or intentionally optional, without burning out.
You’ll walk away with:
A simple framework to evaluate “stay vs. shift” decisions objectively
Signals you’re stuck in sunk-cost thinking (and how it shows up in teams)
How to run a clean pivot: constraints, bets, timelines, and communication
Practical ways to protect your energy and decision quality as pressure builds
Speaker
Lonny James
Lonny James is a founder, operator, and coach who helps entrepreneurs build businesses that are sellable, scalable, or optional - without burning out in the process.
He’s a 3× Inc. 5000 founder who grew his last company from an apartment side-hustle into a $30M+ business with 45 employees. In the early days, he was building while flying - juggling a corporate 9-to-5, fielding eviction notices from his landlord about pallets being delivered to his apartment complex and doing his first million out of a 10×10 storage unit.
But there was a dark side to rapid growth. Lonny became over-leveraged, burned out, and stuck. At his lowest point, he questioned everything...including whether the path he was on was worth continuing.
After a well documented and massive personal turnaround, Lonny successfully exited the business in December of 2024.
Today, he works with founders in the $500K–$20M revenue range through his private coaching practice and Founder Rehab. His work sits at the intersection of strategy, systems, and personal clarity, with a simple goal: helping founders make better decisions.
Location
Tin Roof
300 Glenwood Ave, Raleigh, NC 27603
Questions?
This session is part of Raleigh-Durham Startup Week. Click here to learn more about the event, plus get answers to your FAQs.
Track Supporter
Thank you to Narrasoft for supporting the Strategy Track at #RDSW26!