231 Michael Roub - Think Like Chess, Play Like Checkers

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Michael Roub is the Managing Partner of Inflection 360. He has more than two decades of expertise as a strategic advisor, consultant, executive, and investment banker. A healthcare and wellness expert, Michael also has extensive experience in strategy, M&A, and capital raising. Prior to starting Inflection 360, he held executive roles at Western Dental and US HealthWorks and previously developed and operated surgical centers. He began his career as an investment banker with DLJ. Michael holds a BS in Economics from the Wharton School of Business and an MBA from the University of Chicago Booth School of Business.

In this episode Jason and Michael discuss:

• Transition from investment banking to healthcare executive and strategic advisor
• The importance of real-world exposure and collaborative projects during his education
• Strategic advisory, M&A, and legacy planning for C-suite executives
• Balancing focus on core operations while exploring growth opportunities
• The transformative impact of AI, machine learning, and natural language processing on businesses across industries

Key Takeaways:

• Focus on preparedness rather than memorized rehearsal to ensure effective communication and minimize stress during important interactions. Thoughtfully planning ahead allows for smoother, more genuine conversations.
• Every business has unique needs and challenges. Take the time to listen, observe, and fully understand these nuances before offering any solutions or making decisions.
• It’s crucial to keep core operations running smoothly while remaining adaptable to new opportunities for growth. Balancing these two priorities helps create long-term success.
• With increasing access to capital from sources like private equity and family offices, thorough reciprocal due diligence is essential to protect interests on both sides of the deal.
• Embrace emerging technologies like AI, machine learning, and Natural language processing to remain competitive, but always verify the accuracy of the information to ensure sound decision-making.

“We can be aware of all the opportunities we want to pursue, but functionally, maybe one person tackles one front while someone else tackles another. Or maybe the company, as it's set up, can only handle one change at a time. You think in chess—planning moves ahead—but you're playing like checkers, moving one step at a time. If not, you risk throwing things into disarray. You can’t do everything at once, and I see that every day, not just professionally but personally too.”

- Michael Roub

Connect with Michael Roub:

Website: https://inflection360.com/

LinkedIn: https://www.linkedin.com/in/michaelroub/

Email: [e-mail]

Connect with Steve and Jason:

LinkedIn: Jason or Steve

Website: Rewire, Inc.: Transformed Thinking

Email: [e-mail]

Show notes by: Angelo Paul Tagama

Audio production by Turnkey Podcast Productions. You're the expert. Your podcast will prove it.