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What really happens after you sell your agency? Brent Weaver, founder of UGURUS, knows firsthand — and it wasn’t the beach-and-cocktails story most agency owners imagine. In this second half of our conversation, Brent opens up about what really happens after you sell a business, why his team stuck around (when they had every reason to bolt), navigating the shift from entrepreneur to executive within a corporate machine. He also lays down a fresh perspective on where agencies are headed in the AI era — and why human advantage is still your biggest asset.
If you missed Part One, go back — it sets the emotional stage. This one dives into the raw aftermath.
Brent Weaver is a veteran digital agency founder who scaled UGURUS, sold it not once, but twice, and is now charting a new course inside a larger ecosystem. But behind the polished LinkedIn update is a journey filled with doubt, identity shifts, and deep loyalty to team and customers.
In this episode, we’ll discuss:
What no one tells you about life after a big exit
How Brent is using AI at scale inside E2M
Why “human advantage” still wins in an AI-driven world
The risk agencies face if they treat AI like a gimmick
How to protect clients from the “accountability gap” AI creates
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E2M Solutions: Today's episode of the Smart Agency Masterclass is sponsored by E2M Solutions, a web design, and development agency that has provided white-label services for the past 10 years to agencies all over the world. Check out e2msolutions.com/smartagency and get 10% off for the first three months of service.
When most agency owners fantasize about the big exit, they think freedom, cash, maybe a beach. But Brent paints a more nuanced picture:
“Selling is one of the most emotional business events you can go through. You feel every end of the spectrum — excitement, fear, uncertainty.”
And no, he didn’t tell the team beforehand because he wasn’t even sure himself. Looking back, he remembers asking himself: ‘Is this what I want? What’s going to happen to our customers? Our team?’
Spoiler: Nobody left. Because Brent didn’t cash out and disappear. He pushed hard to give people incentives to stay, rolled up his sleeves, and stayed to help 10x the next chapter.
Brent’s first acquisition with Cloudways was scrappy, entrepreneurial, and chaotic in a good way. But once DigitalOcean came into the picture everything changed. Some of the team joined a small company where they had a voice — then suddenly, it was all process, approvals, structure. And not everyone loves that.
More recently, after staying at the newly-acquired agency, Brent took a step back from a direct client-facing role. At the same time, he had a bigger role in the back office, so despite people not seeing him as much, they also knew he was still around working on the business.
To his knowledge, no one left because of the acquisition. The agency saw the normal amount of churn for the business but all clients and team members knew that Brent was trying to provide a sense of continuity after the sale.
BBack when Brent started learning about the business, he had no idea how to write a proposal. He didn’t know anyone in the industry who could orient him, and ended up writing one in the only format he knew: a high school essay. It was bad. It talked about his interests, why he was trustworthy and why they should hire him.
Comparing that experience from the early 2000s to now, where kids are doing triple backflips on BMX bikes at age 12 because they can watch the trick 10 minutes after it’s invented on Instagram, the speed at which someone can learn anything now is incredible. And even overwhelming.
For agency owners, this means two things:
There’s never been a better time to start.
There’s never been a harder time to stand out.
Ever since WordPress came out, everyone thought agencies were dead. To Brent, all it did was create more demand for people who knew how to use it.
Same with Meta’s new tools or any AI platform. Brent’s take is clear: The tools will make advertising more accessible. But that will actually increase demand for agencies who know how to go deeper.
In his view, there’s no world where his old restaurant client — who had a flip phone and a fifth-grade education — was ever going to run his own ads. He just wants to cook.
Translation: AI doesn’t replace relationships. It just raises the bar on what value you’re bringing to that relationship.
The reality is, even in the AI era people still crave trust and connection. Even in a world where AI is analyzing spreadsheets and diagnosing ad performance better than most marketers, the decision to act still comes down to a human being. “I look at a spreadsheet,” Jason says, “and I want to throw up. But I put it into AI, and suddenly I get clarity.” That’s the shift—AI can sift through the noise, but humans still make the call.
Business owners aren’t about to turn over their bank accounts to a voice assistant. There’s always going to be a place for a trusted advisor—someone who knows the game, who gets results, and who’s got skin in it with you. For agencies, that’s the edge. If you can interpret the data and turn it into action, you’re still wildly valuable.
This isn’t about one person nerding out on ChatGPT after hours. AI isn’t a tool for the top—it’s a mindset for the whole team. At E2M, he’s stepping into a leadership role to help infuse AI horizontally across the company. That means operations, creative, sales—everyone using AI not as a crutch, but as a co-pilot.
The agencies that survive the next wave will be the ones who stop treating AI like a gimmick and start treating it like a business partner. Brent’s advice: don’t wait. Start now, even if it’s nights and weekends. Fire yourself from every job you’re not elite at. And that now includes jobs that AI can do faster, better, and at scale. "Leverage these tools to gut-check your deliverables,” he says. “You owe it to your clients.”
But it’s not all upside. Brent drops a crucial warning about accountability. AI might be amazing at cranking out contracts, pitch decks, and even deal structures—but if it screws up, who takes the hit? If chat tells you to jump off a bridge, and it goes south, you’re not suing OpenAI,” Brent jokes. You’re just canceling your $20 subscription.
And that’s where real coaches, consultants, and experts still matter. There’s a human soul to leadership, and a layer of accountability AI can’t (and maybe shouldn’t) touch. The smart play? Start with AI to generate, then apply your judgment to validate.
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