Reflections on Selling: Mistakes and Emotional Journeys after Exit

When Doug Lowenthal discovered that $1 million in EBITDA was the minimum threshold acquirers looked for in his industry, he had a goal. Then he learned that managed service providers—businesses that offer outsourced IT support—were trading for 6–8× EBITDA. That’s when he realized he was building something truly valuable. 

But getting there required more than just strong financials. Doug had to rethink how he led his team, structured his business, and prepared for life after the deal.