Start Your Exit Planning Early, with Oliver Kotelnikov

Are you really making time to plan your exit, or just hoping you’ll figure it out when the moment arrives? What if the value you’ve built over decades relies on the quality of the journey, not just the destination you’re chasing?

Too often, business owners and advisors assume they can “flip the switch” to sell when ready, only to realize that preparation and self-awareness are critical to both a successful transaction and the life that follows. The mindset shift: treating exit planning as a part of your ongoing journey, not a distant goal, leveraging curiosity and teamwork to maximize value and find purpose beyond the sale.

On this episode, Oliver Kotelnikov, an entrepreneurial business broker who grew a legacy retail operation, took a transformative sabbatical, and now advises owners through IBA, joins Jason Cutter for a candid discussion on navigating exits, identity shifts, and the “T&T” principle: Time and Team. They explore why running a business and selling one are entirely different skill sets, why curiosity beats specialization, and how conversations rooted in listening and self-reflection can unlock new opportunities for brokers and their clients. Real stories, hard truths, and actionable takeaways for those ready to engineer their next chapter.

Subscribe for more insights on evolving from deal chaser to trusted advisor—and share this episode with a colleague who’s ready to build their pipeline and their legacy.

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