One of the hardest things to do as a CEO is to see your business clearly and trust what you see.
This episode of my Critical Moments podcast is with Jacob Ross, the CEO of PebblePost, a company that pioneered Programmatic Direct Mail. A few years ago, they were crushing it. Revenue was up 123%, profitability was strong, and the customer results were off the charts. Their investors suggested testing the market for a sale.
That process didn’t lead to a deal. But it led to something better.
Jacob shared the realization that no matter what story you want to tell about your business, you can’t out-pitch reality. Buyers and partners will see the truth. You can’t fake your way into a better multiple. You have to become the company you want to be valued as.
And that takes trust.
Trust in your vision.
Trust in your instincts.
Trust that the hard decision, the one that goes against the momentum of a “good enough” outcome, is still the right one.
Instead of selling, Jacob and his team made a bigger move. They launched a CTV product and redefined the company’s identity. They stopped thinking of themselves as a direct mail company and started acting like the performance marketing company their customers already believed they were.
His advice to other CEOs?
“Trust yourself. Don’t waste time convincing people who don’t believe in the direction. Move faster.”
It’s a simple line, but it’s real. I’ve felt that feeling — the belief that I can will the world to see what I wanted them to see. Good luck with that. Instead, you need to make your business what you need it to be.
Great CEOs make space for greatness.
And they don’t let good get in the way.
Listen to the episode. It’s a masterclass on clarity, category narrative, and customer-first thinking.
Let’s keep going.
–Mark
