“I’m just a dumb writer,” was something I heard my writer dad say a lot. And I think he meant it. He ran his own advertising agency for a time, and he confessed to me that didn’t run it well. Not because he was dumb. But because he wanted to write, not run a company.
I’ve been running Pro Rhetoric, LLC for 10 years, and I think I’ve had better luck—and more enjoyment. Mostly, because of the talented and committed people I’ve gathered around me and managed to keep: Benjamine and Mike, Jen and Sharon.
We’re meeting later this month to look out at the next 10 years, if we dare—or five, if we don’t—and see how we want to proceed.

And I thought I’d take a moment to look back on what I’ve learned over this decade, and what I’ve become in addition to a dumb writer.
I was offered a chance to buy Vital Speeches magazine a few years before I ultimately did—and at a much lower price than I eventually paid.
One reason I hesitated was that I always hated the business mantra, “Grow or die!” It sounded true to me, and like a trap, and I thought I might prefer death. I learned that it is true—but it’s also true that you don’t have to grow fast. You need to grow so everyone feels a sense of progress. That’s emotionally and economically essential. But you can grow like a tree—naturally and gradually. As my company generally has.
Other things I’ve learned:
Vendors who you pay to carry out your bad ideas won’t be the ones to tell you they’re bad ideas. (Related: When you own a business you have to learn from all your bad ideas because they cost so goddamn much.)
In negotiations: It’s almost always possible to come up a deal of some kind as long as you favor mutual solutions to moral issues. (And as a business person, you should.)
If you can afford them, hire folks who have been around the block a time or two, and who can appreciate what is good about working at your company—and weigh it with some perspective against what is bad. (The first publisher I worked for hired mostly fresh-from-college folks. We were cheap, but we were nightmares to employ because we had no idea how good or bad we had it so we all assumed the grass was greener and could not separate our own professional frustrations with our employer’s limitations.)
When I first went into business I often entertained this literal thought: I don’t want to lie to anyone ever in the course of my work, but I am glad that lying is an option in case I have to. Now, I can’t quite remember why I thought lying might be necessary to run a successful business. Not mine, anyway.
While you don’t have to lie in business, you do have to hustle, and sometimes that involves saying pretty optimistic things to potential customers or partners with a pretty straight face. A leader is a dealer in hope; an entrepreneur is a salesman of it. (In a marketplace as small as executive communications and speechwriting, the hope you sell does have to pay off most of the time.)
When I was trying to scare up the financing to buy this business 10 years ago, I was complaining to an older buddy about the cost. “Not having a boss is worth a lotta money,” he said. And he was right about that.
(Except, occasionally—only occasionally!—you find yourself wanting someone in authority to tell you you did a good job and you should take the afternoon off.)
While you must take the work your company does seriously, you should not pretend to your people that your company is a thread holding the universe together. Nothing worse than a narcissist boss. However, if you do it right, the business inevitably becomes a pretty important part of your colleagues’ lives—and your customers’, too—and that’s a bigger responsibility than you anticipated in those early years. You can handle it. But it’s big. But you can handle it, and if you do so even reasonably well, then you can tell your colleagues something like this, in a memo ahead of your 10th annual meeting:
Without naming names and in no particular order, this company has provided a prolonged escape from soulless companies and asshole bosses that have taken unfair advantage of both our strengths and weaknesses. It has enabled or supported or celebrated or witnessed the writing and publishing of two books, the following of one epic college soccer journey, a marriage, the adoption of three children, the survival of serious illnesses of selves and spouses (and the grieving of the deaths of parents and pets) and a global pandemic and some amazing vacation adventures. And over 10 years, it has provided about 500 email-free weekends (because [as we often say around here] speechwriting isn’t an emergency).
Not to mention some profoundly rewarding friendships among the five of us, constantly enriched by our evolving relationships with literally hundreds of our customers ….
I’ve said it before: at the end of my life, I hope I remember to be as proud of what we’ve all done together here, as anything else I’ve ever been involved with, including my own family.