The First F Quarter I've Ever Seen feat. Kevin von Keyserling

Kevin von Keyserling built a consulting company called Certified Security Solutions and transformed it into Keyfactor, a multi-billion dollar unicorn. Then he walked away from his operating role, got recruited by a local VC firm, and decided to do it all over again with a healthcare supply chain startup called ReadySet Surgical.

But this time, things didn't go as planned.

In this episode, Kevin shares the moment he sat in a quarterly review and said what no one else on his leadership team would say out loud: "It's an F." Every metric missed. Every objective failed. Some things were outside their control, but most of it wasn't. And instead of pointing fingers at the sales team, he owned it as a collective failure. What followed was a comprehensive reset. Three direct reports left. A board member walked. But 18 months later, the company is growing over 50% year over year with a sustainable go-to-market and the right people in the right seats.

We dig into:

• How Kevin transformed two different companies from consulting to SaaS
• The culture shift from tribal knowledge to systemic accountability
• Why he brought EOS and Ninety to every level of the organization, not just leadership
• The "first team" mindset that kept them from vilifying sales
• His biggest mistake: skipping validation and burning cash on a go-to-market that wasn't ready
• What he learned from reading the Elon Musk biography about balancing empathy and results

If you've ever had a quarter you'd rather forget, or you're sitting in a room where everyone knows the truth but no one will say it, this one's for you.