Bill Weathersby: From Bankrupt to $500M+ in M&A—Hard Truths on Scaling Fast, Firing Faster

On this episode of ADAPT or Die: Transformative Leadership Conversations, former tech-CEO-turned-executive-coach Andreas Pettersson sits down with Bill Weathersby, 8-time founder and Chairman of Next Stage Trajectory. Bill shares raw, battle-tested lessons from 40+ years of building, scaling, and selling founder-led businesses—offering sharp insight into when to fire a salesperson, how to accelerate go-to-market without a perfect product, and why “success starts with knowing your walk-off number.”

Challenge → Hiring top sales talent with <50% success rate, balancing speed vs. perfection, and recovering from betting his family’s net worth—and losing.

Adaptation → Instituted a 2-quarter sales cut-off policy, prioritized market share over product polish, and reframed failure as fuel with the support of his wife after personal bankruptcy.

Success → Led six companies to $20M+ in revenue, helped generate $500M+ in M&A value, and now coaches founders scaling from $1.5M to $15M with 14 partners across the US and UK.

🔥 60-Second Hot Seat:
Red flag? Founders too slow to market. Best leaders? Humble team builders. Biggest myth? “Capital is easy.” Most needed question? “What’s your walk-off number?” Best advice he never wanted? “Don’t let failure define you.”

If you're stuck between grit and growth—or ready to scale but unsure how—Bill’s blueprint is your wake-up call. Listen now, take notes, and trim the dead weight.

Connect with Bill:
 🌐 nextstagetrajectory.com
🔗 LinkedIn

Visit ADAPTorDIEpod.com for show notes, free resources, and coaching programs.

Listen to more episodes on Mission Matters:
https://missionmatters.com/author/andreas-pettersson/