Ep 12. More than a Sale: When Legacy and Vision Align – Kai Milota, The Maintenance Team and Jeff Chanen, former owner – CEO 2 CEO

Ep 12. More than a Sale: When Legacy and Vision Align – Kai Milota, The Maintenance Team and Jeff Chanen, former owner – CEO 2 CEO

This episode of CEO 2 CEO explores an incredibly unique transaction between a seller with a vision of the outcome he wanted and a buyer with a vision of how he would begin his own entrepreneurial journey.

Host Scott Sustacek met with Jeff Chanen, the former owner of the Maintenance Team, and Kai Milota, the current owner and CEO, to discuss their long, deliberate ownership transition and build a collective vision for this transaction and the Maintenance Team's legacy.

They share the ups and downs of navigating a business sale—from establishing trust and managing last-minute surprises to staying calm under pressure. You’ll hear firsthand accounts of the challenges and triumphs, the boundaries and concessions, the post-sale dynamics, and their long-standing friendship.

If you’re contemplating selling your business or are fascinated by tales of successful leadership transitions, this episode is a must-listen.

Get inspired by a story where legacy and vision align.

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Jaksot(27)

Ep 26. The Corporate Athlete: Why Game Time Isn't the Time to Practice – Chris Heim, Heim Leadership – CEO 2 CEO

Ep 26. The Corporate Athlete: Why Game Time Isn't the Time to Practice – Chris Heim, Heim Leadership – CEO 2 CEO

Leadership doesn't begin when the difficult conversation starts or the unexpected crisis lands on your desk. According to CEO, board director, and endurance athlete Chris Heim, that's game time—and ga...

5 Elo 27min

Ep 25. The AI Lens: People Before Technology – Jason Dailey, Brandography – CEO 2 CEO

Ep 25. The AI Lens: People Before Technology – Jason Dailey, Brandography – CEO 2 CEO

AI is everywhere, yet many business leaders still wrestle with the same question: How do you embrace it without disrupting your culture, overwhelming your team, or creating fear about the future?In th...

18 Kesä 21min

Ep 24. 10X — From Incremental to Transformational Growth – Andy Siemens, Tailwind Voice and Data – CEO 2 CEO

Ep 24. 10X — From Incremental to Transformational Growth – Andy Siemens, Tailwind Voice and Data – CEO 2 CEO

In this episode of CEO 2 CEO, Scott Sustacek sits down with Andy Siemens, CEO of Tailwind Voice and Data, to explore what it really means to think—and lead—at a 10X level. But this isn’t about bold de...

14 Huhti 16min

Ep 23. Are You Ready for a Board — and Is There a Board Ready for You? – Anne Sample, Navigate Forward – CEO 2 CEO

Ep 23. Are You Ready for a Board — and Is There a Board Ready for You? – Anne Sample, Navigate Forward – CEO 2 CEO

Aspirations for a board seat can often be viewed through a glamorous lens — a prestigious, and perhaps cushy, gig as a next step in one’s career. In reality, true board work is very different than ant...

5 Helmi 32min

Ep 22. Stepping Into the Seat: A New CEO’s Candid Debrief – Ann Houser, The Bailey Group – CEO 2 CEO

Ep 22. Stepping Into the Seat: A New CEO’s Candid Debrief – Ann Houser, The Bailey Group – CEO 2 CEO

Stepping into the CEO seat for the first time can feel like walking into a room where every light switches on at once — the ability to change the trajectory of a company through the decisions made and...

11 Joulu 202517min

Ep 21. Supercharging Marketing and Driving Revenue Growth with AI – Nick Archer, Industrial Tool – CEO 2 CEO

Ep 21. Supercharging Marketing and Driving Revenue Growth with AI – Nick Archer, Industrial Tool – CEO 2 CEO

Artificial intelligence is continuously evolving and rapidly redefining how middle-market companies can operate — far beyond the early days of experimentation with ChatGPT. In this episode of CEO 2 CE...

21 Loka 202517min

Ep 20. The ESOP Secret to Recruiting, Retention...and Growth – Samantha Olinger, Christensen Group – CEO 2 CEO

Ep 20. The ESOP Secret to Recruiting, Retention...and Growth – Samantha Olinger, Christensen Group – CEO 2 CEO

What happens when a succession plan is also a growth strategy? Done right, transforming a business into an ESOP doesn’t just secure the future—it reshapes culture, influences recruiting, sparks collab...

26 Elo 202531min

Ep 19. Doing Good, Doing Well: Where Purpose and Profit Go Hand in Hand – Teresa Fudenberg, CEO of Storm Creek – CEO 2 CEO

Ep 19. Doing Good, Doing Well: Where Purpose and Profit Go Hand in Hand – Teresa Fudenberg, CEO of Storm Creek – CEO 2 CEO

What happens when a CEO dares to lead with purpose — even when the stakes are high? In this episode, Storm Creek CEO Teresa Fudenberg joins Scott to share the remarkable story behind the reinvention o...

7 Elo 202529min

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