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.

Connect with Kevin at kevin@readysetsurgical.com

🔗 Learn more about Ninety: https://www.ninety.io

🔗 Check out our episodes on Youtube: https://www.youtube.com/@90xEOS

🔗 Learn more about Ninety: https://www.ninety.io 📩

Mike Minard spent 20 years bootstrapping Delta Media Group into a SaaS company serving 40,000 real estate professionals. Then he burned out and stepped away. What happened next almost cost him everything he built.

In this episode, Mike shares the hard truth about founder burnout, what happens when you stop watching the metrics, and why he had to step back in and blow things up. He talks about firing an entire department for core value violations, halting sales for a year to fix internal issues, and why the company that doubled in revenue had actually lost its way.

We dig into:

• The real cost of stepping away without the right systems
• Why metrics matter down to the seat level
• The moment he knew something was one degree off
• How his leadership team stepped into support roles overnight
• Why AI adoption has to come from the top

If you've ever wondered what happens when you take your hands off the wheel, this one's a wake-up call.

Connect with Mike on X (Twitter) - @MichaelMinard13

🔗 Check out our episodes on Youtube: https://www.youtube.com/@90xEOS

🔗 Learn more about Ninety: https://www.ninety.io 📩

Kevin Woeste was four and a half years into running a third-generation family business when he almost walked away. Not because the business was failing, but because he was in the wrong seat.

In this episode, the CEO of McSteen Land Surveyors shares the moment everything shifted: learning to let go. Kevin opens up about what it took to stop doing everything himself, trust his leadership team, and allow them to do it 10 times better than he ever could.

We dig into the power of core values, the discipline of delegation, and why sometimes the best thing a leader can do is get out of the way. Kevin also shares his biggest mistake (buying the company), how he optimizes for deep work, and why most leadership advice skips the basics: sleep, nutrition, and showing up well.

If you're a founder grinding in the weeds, wondering when it gets easier, this one's for you.

🔗Connect with Kevin on LinkedIn - https://tinyurl.com/mr427yrz

🔗 Check out our episodes on Youtube: https://www.youtube.com/@90xEOS

🔗 Learn more about Ninety: https://www.ninety.io 📩