When Dr. Jim Gregory talks about corporate branding, he doesn't speak in abstractions. He speaks in boardrooms entered, pitches won, and one stubborn naysayer who nearly cost him his sanity—and eventually drove him back to school for a doctorate just to prove he was right.

I sat down with Jim to trace the arc of what he built: a Madison Avenue consultancy born on $300 and determination, a proprietary research index co-developed with the Wall Street Journal, a cross-border sale to his friendly local competitor, and a post-exit second act writing novels faster than most people read them.

It's a blueprint for building something real, selling it well, and refusing to stop.

The $300 Bet on Madison Avenue

This wasn't a funded startup or a family business handed down. Jim was 23, had $300, and put it on one month's rent for a floor of a brownstone on Madison Avenue. No template. No safety net. Just the conviction that he belonged there.

His future wife Evelyn, who walked away from a solid Wall Street career to co-found with him, became the business partner who balanced his sales-and-creative instincts with financial discipline. The division of labor was clean from the start: he ran sales and creative, she ran operations. When he once asked her to present a project in his place, her answer was a firm no—and he never asked again.

For the first ten years, they did whatever it took to survive. Their biggest account was the Long Island Railroad's timetables. It wasn't glamorous, but it was profitable, and it kept the lights on while they figured out what they actually wanted to be.

Inventing a Category (Then Teaching the Market to Buy It)

The turning point came when Jim and Evelyn stopped asking "how do we compete?" and started asking "what do we stand for?" Their answer: corporate branding. The idea that your company is your most important product and that its brand can and should be measured, valued, and actively managed.

It was a contrarian bet. Advertising agencies at the time gave away strategic thinking to sell production. Jim's firm flipped the model: lead with consulting, charge for ideas, and let the work speak.

Books followed—one every three years like clockwork, thanks to a full-time collaborator named Jack Wishman who wrote overnight while Jim refined and directed in the mornings. McGraw-Hill published them. Business Week, which McGraw-Hill owned and which was also a client, ran full-page ads promoting them in the Wall Street Journal. Clients didn't just come—they came pre-educated and pre-sold on the vocabulary Jim had built.

"We created our own brand," Jim told me. And they did.

The Core Brand Index: When Instinct Became Proof

The most ambitious thing Gregory & Clyburn built wasn't a campaign or a client relationship. It was a research instrument: the Core Brand Index, developed in cooperation with the Wall Street Journal and General Electric, tracking the corporate reputations of 500 companies through consistent quantitative phone research over 20 years.

The point wasn't just measurement. It was prediction. The models, built by Jim's nephew and a collaborator from DuPont, could forecast whether a given level of communication spend would move the needle on a company's cash flow multiple. Positive or negative, and by how much.

Cisco's John Chambers used it. Michael Dell used it. It got CEOs nodding in boardrooms across the country.

The problem? One naysayer could kill it every time. Twenty people aligned, one skeptic in the room, deal dead. Jim carried that frustration for decades. It's what eventually drove him to get his doctorate in statistics after selling the company, not to tell anyone "I told you so," but to understand his own work well enough to have handled that one objection better.

Growth Through Acquisition (Before Anyone Called It That)

Long before M&A became a formal strategy for agencies, Jim was doing it instinctively. A competing team approached him about starting their own firm. His partner Larry McNaughton met with them and offered a different pitch: join us instead, and skip all the hard work of going it alone. They came over and brought the MasterCard account with them.

Jim structured equity participation for key contributors through stock plans. He funded growth through a private placement around 2000. He opened offices in New York, Los Angeles, Frankfurt, and Tokyo, staffed with three or four people each, all following a consistent delivery formula. He treated commitments like contracts: if it was written down, he honored it, every time.

"We were very reputable in terms of that," he told me. "We did what we said. We didn't weasel our way out of anything."

Knowing When to Sell (and Why Clean Books Matter)

By the early 2010s, the signals were there. Evelyn had retired. Jim was tired of the boardroom battle he'd been fighting for years. The advertising model he'd grown up with—15% commission, creative respected as craft—had eroded. He'd given the same speech enough times that once, mid-presentation, he wasn't sure if this audience had already heard it.

"You begin to feel like a pitcher who's lost his fastball," he said. "You're the only one in the stadium who knows you've lost it."

He engaged Generational Equity as a broker around 2010-2011. They did what good brokers do: helped him build a valuation thesis that could account for the intangible asset at the heart of the business—the Core Brand Index itself. That changed everything about how the firm was positioned to buyers.

The process took longer than he expected. Six to eight months pitching prospects who weren't the right fit. Another six to eight months working through a deal with the buyer who ultimately made sense: Brand Logic (later Tenant Partners), run by Hampton Bridwell, a friendly competitor Jim had known for years and occasionally traded referrals with.

Generational Equity revived that conversation. Jim and Hampton had a running list of reasons the deal wouldn't work. The broker took three objections at a time, worked through each one methodically, and kept going until the list was empty. When they got to the end, there was nothing left blocking the deal.

They closed in 2013.

The Integration That Worked Because the Relationship Was Real

The sale wasn't just financially clean, it was relationally built on trust accumulated over years. When COVID hit and the agency world took a hit, Jim was flexible on the payout structure. Tenant Partners was flexible in return.

More than a decade later, they asked him to write the firm's 50-year retrospective. He said yes immediately.

That's what it looks like when a deal is done right.

The Playbook You Can Steal

Differentiate early, then teach the market. Corporate branding wasn't a recognized category when Jim built around it. He made it one—through books, speaking, and sheer repetition until buyers arrived pre-educated.

Hire someone to sustain the thought leadership. Jim didn't write his books alone. He had a full-time collaborator whose job was to get the ideas out of his head and onto the page. One person's job was submitting for awards. Another's was building the statistical models. Execution is a team sport.

Build a board of advisors. Jim credits this as one of his most underrated moves. Not a board of directors: just the best people in your industry, compensated modestly, available for the hard questions. Most of them will say yes if you ask right.

Take one week a year away with your partner. No clients, no deliverables. Just the big questions: Where are we going? Are we on track? What are we not doing that we need to do? They updated a five-year plan every year and shared it with the whole company.

Keep your books clean and honor your commitments. When Jim had investors, he paid them out as promised. When he had equity partners, he didn't renegotiate when it was inconvenient. That reputation made every future deal easier.

Sell to someone who understands what you built. The holding company offers never fit because they couldn't access what Jim had already built—relationships at the CEO level. The buyer who worked was the one who already spoke the same language.

For Sellers: How Jim Made This Possible

Jim spent years before the exit making the business sellable, not by polishing it up for buyers, but by running it with discipline from the start. He documented processes, built leadership below himself, created a research asset with real quantitative backbone, and structured equity thoughtfully for key contributors. When the time came, there was something real to sell.

He also told his team what was happening. He didn't hide the process. He explained what he was looking for, committed to not settling just for the money, and trusted them with the uncertainty. Most of them stayed with him through it.

What's Next

Jim hasn't slowed down. Three novels in three years—each one drawing on 40 years of experience in boardrooms, on stages, and in the middle of deals that didn't go as planned. Zephyr's War, Killer App (an AI thriller that predates many of today's headlines), and his newest, Ghost Town, a historical novel just out and already earning strong reviews.

He writes because he still has stories to tell. And because, as he puts it, golf is frustrating.

Listen to the Full Conversation

Hear how a kid from a blue-collar background opened an agency on Madison Avenue with $300, built a research methodology used by Michael Dell and John Chambers, navigated a multi-year exit to the competitor who knew him best, and never stopped writing.

▶️ Listen to the full episode.

Find Dr. Jim Gregory's novels—including Ghost Town, Killer App, and Zephyr's War—at Amazon, Barnes & Noble, or directly at JamesRGregory-Books.com.

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