Knowing the right time to sell your business is often a gut-based decision: it just feels right.

For serial entrepreneur Paul LeBlanc, he knew it was time in 2012 to step away from Arrivals and Departures (formerly known as Extreme Group) advertising agency. He just didn’t expect it to take almost a decade after to exit.

Paul started the agency in 1997 without much knowledge about marketing or advertising. He saw a need – and an opportunity – in the Halifax market for a creative agency, jumped in and launched what was then known as Extreme Group. Over the years, he scaled and adapted the business expanding from a creative design shop to a full-service advertising agency.

Spending time in Toronto with industry icons like Paul Lavoie and Frank Palmer inspired Paul’s love for the business and the evolution of the company to include advertising, interactive and public affairs over time.

In 2005, Extreme Group had over 70 people working in its Halifax office on some of Canada’s best-known brands such as BellAliant and McCain, but the industry was changing with more client head offices relocated to Toronto and centralized their marketing there.

“I saw where the puck was going and convinced my wife to move to Toronto,” says Paul. “When we opened the office in 2007, we didn’t have any staff or clients, but we were ready to take on the market. The financial crisis hit in 2008 but we were able to survive that and eventually ended up thriving.”

Paul and his family made the decision to return to Halifax in 2011 and in 2012, he felt a passion to pursue other business opportunities and try something new.

“I went to my partners at the time and said you guys take it and run it. I'm going to give you some stock options in the company, I want to go find other things to do, which I've been doing since 2012.”

The partners ran the day-to-day operations with Paul being involved in key decisions like acquisitions or capital expenditures, but he had fully stepped away from the operations. Over the next few years Paul was involved less and less until he and the partners agreed it was time to change to how the business and the shares were structured.

“For the next four years we probably looked at 15 different business models to negotiate a deal, but it was complicated and there were a lot of emotions in play. I think there was some frustration on both sides as we were struggling to find a compromise on the deal, and I finally said, just take me out entirely and that was what helped us to eventually find a deal structure that worked for all of us,” he recalls.

When COVID hit, they agreed to pause and batten down the hatches as they tread water through the pandemic. Marketing and advertising is usually hit hard during tough economic times and with so much uncertainty, Paul didn’t think it was fair to his partners to push to close the deal. In spring 2021, the partners and Paul picked up the conversation, went through the negotiation process and made a deal that saw him fully exit the business.

When asked if this deal was harder emotionally than others Paul has been involved in, he says, “I've done a lot of soul searching on that and the agency was part of my life for 25 years, literally half of my life. The passage of time is what’s emotional for me. I don’t have a love loss for the mechanics of the business, but I am very proud of the work we’ve done – like the Skip the Dishes marketing campaign featuring Jon Hamm.” That plus the fact that the operators of A+D were the right heirs to the business and deserved ownership given their efforts over the past decade.

Now, Paul is typically on the buying side of a deal and offers invaluable advice for business owners who are considering selling their business.

“If you're at all contemplating an exit from your business in the future, use the time to your advantage and set your business up for the best possible exit. Too many business owners literally leave millions of dollars on the table due to a lack of preparation. I think a lot of people get to a stage where they’ve had enough and they’re ready to sell but haven’t prepared whatsoever. They’re ready to go so they blindly start conversations and either end up not getting the best deal, or worse, no deal gets done.“

Paul adds that there’s often too much of a gap between what someone’s willing to pay and what someone wants to get. It comes down to finding the right professionals to guide you through the process.

Most people will go through the sale of their business only once or twice in their lifetime so it’s important to get it right. Paul advises to go ahead and talk to that friend of a friend who sold their business, but don’t appoint them your sole advisor. He continues by recommending that the best thing you can do for your sale is to make sure you've got the best people available to you. Spend the necessary time finding out who those people are and get them on board. Don't worry about paying for them because they'll pay for themselves—ten times over.