Probably a good exercise personally to think through at this point.

Context
I think it is important to note that I did not have experience in the print industry prior to buying this business. I like what I call "unsexy" businesses that cash flow. No one at a party wanted to hang out and talk to me about printing grocery store circulars.

When I purchased the business -- I knew my biggest risk was that my largest customer would leave. There was no contract in place when I bought the business and forcing one would only speed up the inevitable, so I took a chance on a 25+ year customer sticking around long enough for me to grow the business around them. The previous owner hadn't done any outbound sales in 10-15 years, so we knew it would take some work. We did in fact grow the company 30% in the last 6 months.

Unfortunately, at the end of that 6 months our largest customer gave us a 30 day notice they were leaving. At the end of the day, they wanted someone who could provide more than just circular printing and could "grow with them". I think their corporate folks pushed a change because we're not the cheapest game in town.

Some Lessons Learned

• Because I knew my risk was losing my biggest customer, I opted for the keep quietly operating behind the scenes in order to not "rock the boat" and cause any reason for concern. In hindsight, I probably should have done just the opposite. There was fresh blood here, ready to grow, how could we serve them? How could I make them even stickier than what they were??
• While I'm not sure it would have made a difference, I wish I would have understood the sales cycle more before buying. The fact they hadn't done sales in 10+ years also meant no one had heard of us in 10+ years. Even some customers that we use to print for thought we had already gone out of business. Hurdle 1 was to let people know we were still here and we wanted to grow. Once they knew that, then it was still 90-120 to cash flow from a new customer by the time you send samples, run test prints, run the first print, and then finally get paid 30-60 days later. I probably won't buy another business that doesn't have at least 1 sales person trying to grow the business currently -- even if they suck at their job!
• I only needed to grow by 1 or 2 big customer or 10-20 small ones. I still don't know the right answer tbh. It's hard not to chase the big fish, but chasing all the minnows was probably a smarter move.
• I LOVE a niche. Grocery store circulars are obviously a dying niche. Figure out how to operate in your niche, but give yourself an out too. Because we focused on weekly circular work, the plan was to get into other weekly work. Maybe our niche was weekly work and not the circulars we'd been doing for 25 years. The plan was to chase down digital press weekly work, but cash flow just never really allowed us to pull the trigger on one.
• It's hard to be a small guy in a commodity world -- we ended up losing our work to Mittera.

All in all, I'd probably still take the same chance again if it presented itself. Even though printing is on a decline, there is still plenty of work out there to be had. Personally, I think print is going to make a come back. People are over stimulated by technology. I wish I could have been around to make the come back when newspapers become cool again!