For ten years I lived the founder grind — not a quick exit. I bootstrapped, raised venture debt, navigated growth, structure and team evolution, and eventually walked it through to exit. An unusual path, and one that taught me what the playbooks don’t. I started as an engineer, moved to sales before making the jump to founder. 25 years later I’ve been on each side of the table — buying, selling, investing, founding. At IBM Ventures, I learned how investors and enterprises really think — the politics, the pattern-matching, the unspoken rules before spinning out HealthXL. 10 years after founding we sold the company and I stepped away. It was a great exit for all but it was hard to rebuild my identity outside of the company. It was time to do something new and difficult — namely train as an exec coach and as a ski instructor. After 3 attempts (and bruised ribs) I finally passed the BASI and Association of Coaching exams.