The one where we pull the plug on a $20M acquisition

By Devon Hennig

Boardroom Confidential is a collection of wild-but-true stories from the careers of me and my friends.


It was 9pm ET the night before a call with our CEO to make a GO or NO GO decision on the acquisition of a media company for $20M.

He had already told us he would support our decision either way, as he wasn’t a sales or marketing expert and he trusted our counsel.

But there was a problem.

Our inner circle of decision makers, including myself, the CFO, and the Chief Revenue Officer, couldn’t agree. We kept going back and forth on whether the acquisition was a good idea.

If we couldn’t find consensus, we were hooped.

I wanted to do it because I thought it would help our lead generation team immensely. The media company we were looking at had drool-worthy amounts of traffic, and we could pivot it to benefit our brand in a heartbeat.

The CFO was on the fence, and the CRO was leaning toward no, as the deal carried certain risks that he thought may outweigh the benefits.

We needed a tie breaker, so we phoned a board member.

The board member heard us out, and then he said something I’ll never forget.

“You’re at the end of the deal,” he told us. “You’ve got ‘deal eyes.’ I’ve been there, trust me. I’ve done more deals than I can count. You get so close that you start to overlook things or bend where you shouldn’t bend because you want to get it done. All you have to do is step back and ask yourself, ‘What would you have to believe for this to work?’”

There was a pause on our end of the line.

“What would you have to believe for the deal to make sense?” he asked. “Forget the fancy modelling for a second. Just do the napkin math and see if it makes sense. In this case, would you believe that you could drive a million website visitors a month that turn into 50 customers at an average deal size of $45k each? If you believe that, you should do the deal.”

The three of us sat back and looked at each other.

Did we believe that?

“And one more thing,” the board member said. “I’ve never regretted a deal I didn’t do. In this case, I’ll support you no matter what. But I’ve never, ever regretted a deal I haven’t done.”

We thanked him and hung up.

Before any of us spoke, I knew our decision.

We decided to kill the deal.

The next day, the CEO heard us out and said he was disappointed since he had “deal eyes” himself, but he understood. We never spoke about it again.

To this day, I believe that if this failed acquisition had been a Supreme Court case, I could have been the justice who wrote the dissent. I could’ve convinced myself that the deal would have been worth it, but in the end the others couldn’t — and rather than die on that hill, I decided to listen to the board member who said that I would never regret turning it down.

And guess what? He was right. No regrets here.

Devon Hennig

Devon Hennig is a writer, marketer, and ex-game-show host. He quit his job as a software executive to make a go of it on his own. Follow along as he tries not to go broke.

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