For many, childhood is a time to try on possible future identities—playing house or pretending to be a doctor, teacher or some other familiar role. Not Jeff Duncan. “I would be playing business,” he says, adding that this often meant convincing his reluctant older sisters to let him be the boss for a bit. Fast-forward a few years, and it only made sense that, at 22, Duncan found himself as the “captain of my own ship,” he says.
From Travel Agency Sales to Event Housing Management
Duncan skipped the traditional college route and jumped straight into business, ascending from sales coordinator at a travel agency to vice president of sales in four years. Then, as the travel agency industry teetered, he saw a smarter play: Ditch the airfare, car rentals and other elements, and focus instead on room-block management.
“I realized that this was… scalable, because it didn’t matter whether a contract was for 100 rooms or 1,000 rooms. It was materially the exact same contract,” he says. “It just had another zero at the end, which meant that there was another zero in the commissions that we were going to be receiving.”
Duncan worked out a deal to spin off that promising sector of the travel agency into what would become Meetingmax, an event housing management business that powers some of the nation’s largest business and entertainment gatherings today.
Pivoting From Services to a SaaS Business Model
With “always agile” as a guiding principle, Duncan discovered the value of a nimble approach very early on. Not long after establishing this new company providing large-scale accommodation booking services, he transformed the business again into a software-as-a-service (SaaS) model at the request of a client who wanted to license the program he’d created. “I was like, ‘Well, I’m not really in the software licensing business, but I’m an entrepreneur, so let’s figure it out,’” he says.
The market responded. “We signed the Spokane [Washington] Convention and Visitors Bureau as a SaaS client, [then] Spokane talked to Madison, Wisconsin. [Then] Madison, Wisconsin, talked to Norfolk, Virginia.… All of a sudden, we [had] half a dozen to 10 convention and visitor bureaus that are licensing our software,” Duncan says.
Now, Meetingmax has helped provide the infrastructure behind events like South by Southwest for the past 15 years, and it has also previously powered Oracle OpenWorld, Cisco Live, Gartner IT Symposium/Xpo, HP Invent and IBM Think. In other words, “big events that are very, very complex,” Duncan says.
It’s big business. And yet, he says, “if you could imagine a worse business to be in during COVID-19, there are a few, but that was right up there as one of the worst.”
What It Looks Like to Pivot a Business During a Crisis
In 2020, Meetingmax was projected to transact about $225 million in hotel bookings. Then, from March to April of 2020, the company’s revenue dropped 92% in one month. Duncan says he had to “batten down the hatches,” do the math and ask: “What does 18 months from now look like if revenue doesn’t recover?” From there, he right-sized the company’s workforce to survive for 18 months. With the adjusted cash flow, Duncan knew they could weather the storm. “And at that point, I felt totally free to be like, ‘Hey, we’re good for 18 months,’” he says.
With events on pause, it opened up the opportunity to try something new—and put his agility to the test again. He asked himself, “If I can’t control this thing, what can I control?”
“I can control my thoughts and my actions,” he says. “Let me just focus on the things that I know that I can do, which is mindset and figuring out what actions I can take to still create value for the world, even though one side of my world was quasi-crumbling. That was the gift of that opportunity at that time.”
The opportunity arrived in the form of talent management—particularly apt timing, as “everyone was watching everything” in 2020, he says. Duncan had been helping Harry Jowsey, a friend and Australian content creator, with some business logistics on the side. With more time on his hands, Duncan was ready to dig in. “That’s when I said, ‘Harry, I think we can double down on this,’” he says.
With people at home, watching whatever content they could, social media personalities were blowing up overnight. “It was just this crazy wave, which was fascinating because we were both learning,” Duncan says. “The two of us were both learning at the exact same time.”
Soon after, Duncan founded the talent management company Ingenuity Live and was bringing over employees from Meetingmax, proving that if he could pivot, so could many of his team members. He quickly transformed “A-team” Meetingmax employees into talent managers.
“[It was] an unfair advantage for a startup, because a startup is usually bootstrapping. And I’m like, ‘I’ve got an entire team of people that I can tap,’” he says.
Which Business Skills Transfer to a New Industry
Perhaps to some, it looked like a leap. But to Duncan, it was a natural extension of the skills he already had and trusted.
“In any business, it’s probably 80%... fundamental skills and you could port over to whatever you are doing. And that’s contract negotiation, reading the room, being the people person, understanding accounting and finance, understanding how to read a balance sheet and what’s going on with a P&L, rolling cash flows and all those bits and pieces that you could port over to anything that you were doing,” he says. “It’s 20% that’s the learning curve.”
The playbook? Identify what could transfer, and move quickly to apply it in a new arena.
Even Ingenuity Live, in its own way, is a change machine, helping clients take careers rooted in one entertainment platform—reality TV, YouTube or TikTok, for example—and transform them into multiplatform businesses. Today, the agency’s content creation clients account for a total of roughly 250 million followers across all platforms.
Running Two Businesses Built on Connection
Eventually, the world reopened. The pendulum swung back with even greater force than before, and events started again. Meetingmax was back, and Duncan found himself the chief executive officer of two healthy businesses: “I took the worst of one and created the best out of the other until the worst of the [first] one became good again,” he says.
Now, with booming businesses in both the live-event industry and online entertainment, Duncan says his worlds aren’t all that different—he’s in the business of helping people find their community.
“That’s really Meetingmax’s core purpose, this magic that occurs when human beings get together,” Duncan says. “And then when I [look] at the Ingenuity Live on the entertainment side, it is very much [about] this creation of tribes.”
Who do followers relate to? What accounts do they see themselves in? “The through line [really is] this sense of gathering, connection and belonging,” he says.
Why Staying Agile Matters for Entrepreneurs
For Duncan, the old adage “the only constant in life is change” couldn’t be truer. “Always agile” continues to be his North Star, a waypoint for realignment.
“If you get stuck in your ways, [it’s] probably just because it worked yesterday, but that doesn’t necessarily mean it’ll work tomorrow—and maybe it shouldn’t work tomorrow.… The world changes, and to be able to adapt to it has a tendency of being a recipe for predictable success,” he says.
This article was first published in the November/December 2026 issue of SUCCESS® magazine. Get your copy here.
Image from Adobe Stock
