Imposter Syndrome Is Normal and Healthy

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What does it really look like when employees step up to buy the agency they’ve helped run for years? Today's featured guest will share how she and her partners carried forward the 30-year legacy of an agency founded in the days of print and stamp, a business that has not only survived but thrived through three different ownership handoffs.

You’ll hear how they transitioned from licking envelopes to leading digital campaigns, navigated buying the business during COVID, and tackled the imposter syndrome that comes with suddenly being “the boss.” If you’ve ever thought about selling your agency, or buying one, this conversation is packed with lessons on culture, succession, and keeping an agency alive for the long haul.

Alyssa Ash is one of the principals and co-owners of AOR, a creative and digital agency focused on branding, marketing, and web, with a strong focus on real estate development, municipalities, and economic development projects. Think housing solutions, community connections, and projects that shape cities—that’s their sweet spot.

Alyssa and her two business partners are the third generation of owners keeping AOR alive since its founding in 1992. A rare kind of legacy in agency land.

In this episode, we’ll discuss:

• How employees can be groomed into ownership.

• Lessons from buying an agency during COVID.

• Why imposter syndrome is normal (and even healthy).

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Sponsors and Resources

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A Legacy of Print and Culture

Back in ’92, AOR wasn’t cranking out websites or SEO strategies. It was the time of print design, direct mail, licking stamps, and die-cut lounge chair mailers that made people long-time clients. It’s not common that an agency that gets acquired lives on like this, but the founders had built something special. Each generation of owners didn’t just grow the client list—they protected the culture.

When the founders sold 13 years after starting the business, keeping that culture intact was non-negotiable. Fast forward again, and Alyssa’s crew inherited not just an agency, but a philosophy: honor the people and the community as much as the work.

Transitioning from Employee to Owner

Unlike an outside buyer swooping in with an SBA loan, Alyssa and her partners were homegrown leaders. They’d each put in 10–15 years, running departments in strategy, sales, and operations. By the time the second set of owners started floating the idea of selling, the trio was already running day-to-day operations.

At first, the conversation was casual, “Would you even want to own the agency someday?”, but over time it got real. The financial side was initially not even part of the conversation, although they did give a reasonable runway of five to ten years for the acquisition to happen. The fact that three of them shared the load made the acquisition possible.

While the thought was intimidating at first, the gradual handoff built their confidence. By the time the deal closed, ownership felt less like a leap and more like the next natural step.

Navigating an Agency Acquisition During COVID

If you’ve ever thought about buying or selling an agency, you know the financing part can get tricky. For Alyssa and her partners, COVID hit right in the middle of negotiations. On one hand, this made it somehow easier for her and her partners to step even more into their roles as heads of the agency. While the owners stepped back from daily operations, Alyssa and her partners made the transition to their new roles.

On the other hand, the pandemic did complicate things as SBA loans looked risky with interest rates climbing. Thankfully, the old owners worked out a five-year owner-financed note instead.

That decision didn’t just save them financially, it cemented trust. The outgoing owners wanted the next generation to succeed and structured the deal so everyone won. As Alyssa put it, “It didn’t feel like a big shift… because we’d already been doing it.”

Fighting Imposter Syndrome (and Why That’s Healthy)

Even with 15 years in the trenches, Alyssa admits stepping into ownership brought its fair share of imposter syndrome. She was still quite young, even though she felt comfortable leading day-to-day operations. This is where the former owner’s trust really helped. They put her in a position to succeed and trusted she could make it.

Ultimately, every agency owner feels that, no matter the stage of their career they’re at when becoming an owner. In fact, it’s the ones who don’t who usually get tripped up by ego.

Preparing the Next Generation

So, is Alyssa grooming her team for eventual ownership? Not yet, it’s too soon. But she is watching for the traits that made her and her partners natural fits: entrepreneurial thinking, leadership instincts, and a bias for taking responsibility.

Her advice to other agency owners thinking about succession:

• Don’t overlook your employees as potential buyers.

• Give them time and a runway to grow into the role.

Protect your culture by keeping it in the hands of people who already live it.

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