Selling a business is often the largest financial transaction an entrepreneur will ever undertake. Yet many owners underestimate the time, preparation, and scrutiny involved once a deal enters the due diligence phase.

In this episode of Are You Ready?, Neil Cockburn is joined by Hugh Watt, Chief Operating Officer of Acera Insurance, to explore the realities of due diligence during a business sale or acquisition. Hugh brings firsthand experience from multiple transactions, both on the buying side and the selling side, and shares lessons learned from helping guide companies through successful transitions.

The conversation covers what business owners should expect once a letter of intent is signed, why due diligence often takes longer than anticipated, and the importance of assembling the right team of advisors. Hugh discusses everything from quality of earnings reviews and financial reporting to confidentiality, management presentations, and the challenges of keeping a business running while simultaneously preparing for a transaction.

One of the key messages throughout the episode is that preparation creates options. Business owners who invest in strong systems, accurate reporting, and experienced advisors are far better positioned when an opportunity arises. Hugh also shares practical insights about deal fatigue, valuation expectations, legacy considerations, and why successful transactions are about much more than simply reaching a purchase price.

Whether you're considering a sale in the next year or the next decade, this episode offers a valuable look at one of the most critical phases of any business transition.

About Hugh Watt
Hugh Watt is Chief Operating Officer and Partner at Acera Insurance, where he helps lead operational strategy, partner integration, and growth initiatives across the organization. With more than 20 years of senior leadership experience in insurance, professional services, finance, and operations, Hugh has played a key role in numerous mergers, acquisitions, and business transitions.

Throughout his career, including leadership roles with Foster Park Brokers, NFP, Nilex, and Acera, he has worked closely with executive teams through acquisitions, ownership changes, post-transaction integration, and strategic growth initiatives. His practical experience on both the buy side and sell side of transactions provides a unique perspective on the challenges and opportunities business owners face when preparing for a sale or acquisition.

Known for his disciplined, execution-focused leadership style, Hugh is passionate about helping organizations navigate change while maintaining a strong focus on people, culture, and long-term success.

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

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
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
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

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 in corporate 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 $250 million 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