Thinking of selling your business? Six lessons from Marc O'Dwyer on selling on your own terms

Marc O'Dwyer has spent 33 years in business, buying 14 companies and selling nine. The one we sat down to talk about was Big Red Cloud, the cloud accounting platform used by over 8,000 Irish SMEs, which he sold in April 2025.

What makes Marc's story worth reading is how close it came to not happening at all. Two earlier deals collapsed at the very last minute, one two weeks before closing and the other just two and a half days out. When the right deal finally came, Marc held his ground on price, turned down an earn-out and was paid in full on the day. Here is what stood out for me.

Marc's decision to sell came from a mix of reasons. He was approaching 60, the product was ready to go international, and it needed fresh investment and new energy to take it there. As he told me, he felt somebody else could take up the baton and grow it further.

The point he kept coming back to was the position he sold from. In his words, "you always need to be in a position where you want to sell, not that you need to sell."

That one sentence explains almost everything else in his story. Because the business was profitable and he wasn't under pressure to exit, he could say no to terms he didn't like and mean it.

For owners considering their own business, the strongest negotiating position is built years before a sale, by running a business that is profitable and doesn't depend on you having to get out.

Big Red Cloud was approached by interested companies once, twice, sometimes three times a week. Marc's view is that you never know when the right one will come, so you should always be ready.

His own business was in good shape. Management accounts were ready within four days of the month end, KPIs were tracked closely, and the legal side was put in order before going to market. That made due diligence, which he describes as the most thorough he had ever been through, far more manageable.

His advice to every owner was simple. "Have all your legal, tax and financial information up to date on a regular basis. You never know when somebody might come and knock on your door looking for your business."

For owners considering their own business, clean, up-to-date numbers give you confidence at the negotiating table and speed through due diligence. Both are worth real money.

Coming from a sales background, Marc assumed he could sell the business himself. He quickly realised that when you're selling your life's work, you need professionals around you, including corporate finance and tax advisers working hand in hand.

He also made a point I would underline. You have to trust your adviser and get on well with them, because there will be late nights and early mornings, and both sides need to be able to rely on each other completely.

For owners considering their own business, bring in the right advisers early, including tax advice on how the sale is structured, and choose people you trust.

For the whole process, Marc didn't tell his staff. He was clear that the business still had to be run as if the deal would never complete, because it still needed to be profitable and the team needed to stay focused.

That discipline paid off. Throughout the final sale, he kept nurturing a large opportunity in the UK, and by the time the deal closed, the new owners were delighted to inherit it. He also negotiated that every member of staff could stay with the business or take a generous redundancy package.

For owners considering their own business, a sale can take months and can fall through at any point. The business you keep building during that time is your safety net, and often part of the value.

Marc knew what he wanted. He understood how buyers value software businesses, whether on a multiple of EBITDA, recurring revenue or revenue, and he had a figure in his head that he wouldn't go below, even when his own advisers thought he was aiming high.

The buyer's first offer was 70% up front, with the rest spread over three years. Marc turned it down. "I want the figure I want, I want paid 100% up front, and I don't want to work in the business. And I stuck my heels in the ground until I got that."

Then, eight weeks before closing, the buyer's side questioned the figures and tried to reduce the agreed price. Marc pulled the deal. The buyer came to meet him in person, saw he was serious, and they agreed a way forward without a discount. As Marc put it, "If you've agreed a price, and it's the price you're happy with, if you feel you're right, you need to be resilient."

For owners considering their own business, know your value before you go to market, and decide in advance what you will and won't accept, including how and when you get paid.

The two collapsed deals hit Marc and his wife hard. They had started planning holidays and even a new house. One deal fell apart when a new managing director arrived at the buyer and decided to go in a different direction, something no amount of preparation could have prevented.

After the second disappointment, his wife set a rule they stuck to. They would not assume any deal was done until the money was in the bank. Marc, who has a background in endurance sport, describes it as controlling the controllables.

For owners considering their own business, do everything you can to make a deal secure, including proof of funds, but plan your life as if it might not happen until it does.

When I asked Marc what he would tell himself the day before the sale, his answer surprised me. He would have arranged a proper celebration with his staff and family. After two deals falling through, he was cautious right to the end, and the moment passed with a bottle of champagne in the lawyers' office.