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What actually happens when you move from planning your exit to executing it?

In Part 2 of this conversation on  Are You Ready?, Neil Cockburn continues his discussion with Gerry Robitaille, President of Assurgo Enterprises, diving deeper into the realities of mergers and acquisitions and what business owners should expect once a deal is in motion.

Building on the foundation from Part 1, this episode shifts from preparation to execution. Gerry shares insights into the deal process itself, including how buyers evaluate opportunities, what can derail a transaction, and why expectations often need to be recalibrated as negotiations progress. The conversation highlights the importance of structure, transparency, and alignment when entering the market.

A key theme in this episode is that selling a business is not just a financial event. It is a complex and often emotional process that requires clarity, patience, and strong advisory support. Gerry emphasizes that the best outcomes come from well-prepared businesses that understand their value and are ready to respond when the right opportunity arises.

Part 2 reinforces a critical message for business owners. Getting ready is only the first step. Executing successfully requires discipline, perspective, and a clear understanding of how deals actually come together.

About Gerry Robitaille

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Gerry Robitaille is President of Assurgo Enterprises and a seasoned corporate finance advisor with more than 30 years of experience in business leadership, ownership, and M&A advisory.

His career spans executive roles in public companies, private business ownership, and complex transaction execution. Today, he works closely with business owners to support growth through acquisition, prepare for succession, and execute strategic exits.

At Assurgo, Gerry leads a team focused on acquisitions, management buyouts, and exit planning for companies typically in the $20 million to $100+ million revenue range. The firm has advised on transactions representing hundreds of millions of dollars in enterprise value and is actively engaged in over $250 million in mandates.

Gerry is passionate about helping owners maximize value, protect their legacy, and exit on their own terms.

About Neil Cockburn

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Neil Cockburn is a Chartered Professional Accountant (FCPA), Family Enterprise Advisor (FEA), and Trust and Estate Practitioner (TEP), and the Director of Family Enterprise Advisory Services at Kingston Ross Pasnak LLP. With more than 40 years of experience working alongside business owners and family enterprises, Neil specializes in succession planning, intergenerational wealth transition, and estate strategy. He is known for helping families navigate complex transitions with clarity and confidence—always grounded in one central question: Are you ready for what comes next?

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To learn more and connect with Neil Cockburn of Kingston Ross Pasnak, pleasevisit: https://www.krpgroup.com/our-people/neil-cockburn

This video podcast series is proudly produced by the team at Road 55 - locatedin Edmonton, Alberta.
For more information, please visit: www.road55.ca 

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