Why I Paid $200K to Be the Least Impressive Person in the Room
Ten years ago, I joined a Vistage CEO group where I was clearly the smallest fish in the pond—one member owned 100% of a $1B company. It was uncomfortable—but transformative. Since then, I’ve spent ~$200K on coaches, consultants, masterminds, and elite certifications (Harvard, Stanford, MIT, etc.). Expensive? Yes. But easily the highest ROI investment of my career. Why? Because a single conversation with someone ahead of me often saved 6 months of spinning—or $100K in mistakes. Here’s What Most CEOs Miss 👇 If you're the smartest person in the room, you're in the wrong room. Comfort is the enemy of growth. Surrounding yourself with people who don’t challenge your assumptions keeps you solving $10K problems instead of $10M ones. I learned this the hard way. Early on, I stayed in a "Small Business" group. Nice people, but no one far enough ahead to challenge my thinking. When I leveled up—paying 5x more to be around CEOs 10 years ahead—it changed everything. Even top founders seek out bigger thinkers. I saw it firsthand at events like the EY Strategic Growth Forum—where billion-dollar CEOs were still seeking mentorship from even bigger operators. How to Do This Intentionally 👇 Build Three Growth Networks: 1. 10 Years Ahead – People whose "normal" is your stretch goal. Get in paid, curated groups or invite-only events. 2. Shoulder-to-Shoulder – True peers. Share wins, losses, and real talk. 3. The Unrelated Genius – Outsiders from other industries. They’ll help you see what you’re missing. Pro Tip: Give value first. Promote their wins. Introduce them to helpful people. Invest in the relationship before you need it. How to Build the Right Rooms 👇 1. Audit Your Current Network → Who are your top 10 professional relationships? Who challenges you? Who’s ahead of you? If >30% aren’t above your level, you’ve outgrown the room. 2. Identify What’s Missing → Do you lack mentors? Peers? Outside-industry thinkers? 3. Map It Out → For each gap: List 2–3 people to connect with → Choose 1 paid group to join → Pick 1 event in the next 90 days → Hire 1 fractional expert to solve a stalled “important but not urgent” item in 30 days