‍

‍

What does it really take to sell a business successfully?

In this episode of Are You Ready?, Neil Cockburn is joined by Gerry Robitaille, President of Assurgo Enterprises, to explore the realities behind mergers, acquisitions, and business exits. With more than 30 years of experience incorporate finance, ownership, and transaction advisory, Gerry brings a practical, real-world perspective to one of the most important decisions a business owner will ever make.

The conversation focuses on a key truth that many owners overlook. The value of a business is not created at the moment of sale. It is built over time through preparation, structure, and strategic decision-making. Gerry shares insights from working on transactions across a wide range of industries, highlighting what buyers are really looking for and why some businesses achieve strong outcomes while others fall short.

This episode also challenges the idea that exit planning is something to think about later. In reality, the most successful exits are the result of years of preparation. From understanding valuation drivers to aligning operations and leadership, readiness is what ultimately determines both the outcome and the options available to an owner.

If you are building a business with the intention of eventually stepping away, this episode offers a clear and practical look at how to think about that journey. Not as a single event, but as a process that starts long before the deal is on the table.

About Gerry Robitaille

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 $250million in mandates.

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

‍

About Neil Cockburn

‍
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?

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

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