I Built a $55M Company Then Lost It All. Here’s What I Learned.

Guest: John St. Pierre, entrepreneur, author of The $100M Journey, co-founder of Entrepreneurs United

Summary

After scaling a company to $55M in global revenue, John lost it, 15 years of work, gone. In this brutally honest conversation, John unpacks what he calls patient ambition (urgency with discipline), how unchecked growth creates hidden vulnerabilities, and the seven principles he used later to scale another company from $5M to $100M the right way. We dig into strategic capital planning, protecting equity and control, building an entrepreneurial culture without giving away the cap table, and why money doesn’t change people, it exposes them.

Highlights & Big Ideas

• Patient Ambition: Ambition without patience = cliff. Patience without ambition = stagnation. You need both.

• Strategic Capital Planning: Don’t sprint to 40% growth if your cash flow funds 5%. Plan sources and uses, protect control.

• Protect the House: As you grow, risk compounds, legal, HR, customer concentration, credit, fraud. Build controls as you scale.

• Own vs. Control: You can keep decision control with less equity or lose control with more. Paper it before you need it.

• Reinvest Smartly: AB test, double down on winners, kill losers quickly. Growth should increase net operating cash flow.

• Culture of Entrepreneurship: Create owners’ mindsets with phantom equity/growth plans; don’t casually dilute the cap table.

• CEO to Chair: You can’t step back unless principles 1–6 are real: cash, controls, leaders, and clarity are in place.

• AI, Used Right: Tool for efficiency and thinking aid, never a substitute for thinking. Avoid “AI-homogenized” sameness.

John’s 7 Principles (Rapid Summary)

1. Protect & Grow Your Equity: Separate economics from control; lock operating agreements now.

2. Build Your Own Growth Capital: Cash flow first; debt/investors last and intentional.

3. Reinvest Smartly: Fund proven levers; stop funding pet projects.

4. Culture of Entrepreneurship: Incentives aligned to value creation without cap-table chaos.

5. Protect the House: Controls, vendor/customer risk, fraud prevention, legal/HR readiness.

6. Owner Liquidity: Safely enjoy gains along the way (tax-smart), not just on exit.

7. Move CEO → Chair: Systems and leaders run the machine; you steer outcomes.

Memorable Quotes

• “Ambition without patience will run you off a cliff.” — John

• “Money doesn’t change people; it exposes them.” — Lee

• “Show me the incentive and I’ll show you the result.” — John

• “Responsible growth is good for every stakeholder.” — Lee

• “Don’t build a shiny castle on a hill with a rotting foundation.” — John

Resources Mentioned

• John St. Pierre — website & tools: 100mjourney.com

• Book: The $100M Journey — John St. Pierre

• Book: Your Most Important Number — Lee Benson

• Entrepreneurs United (event/community)

• “Value Creation Flow Structure” — Lee’s framework for seeing bottlenecks end-to-end

Take Action (Pick One This Week)

1. Capital Map: Draft a simple 12-month strategic capital plan (sources/uses, cash conversion, growth rate your cash can fund).

2. Vulnerability Sweep: List top 10 risks (legal, HR, credit, fraud, concentration). Assign owners, deadlines, and first fixes.

3. Reinvestment Rule: Define your “double-down criteria” and a kill switch for initiatives that burn cash without traction.

4. Control Check: Review operating/partnership docs for voting/control rights. Close gaps before you need them.

5. Incentive Tune-Up: Align leader comp to value creation (phantom equity/growth pools vs. casual dilution).