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The 2024 ACG Legend: Jay Jester

How Plexus Capital’s Jay Jester built out the ACG network—and his own business development prowess—from Boston to Florida

The 2024 ACG Legend: Jay Jester

When I met Jay Jester, I was a fairly green reporter. I had been covering venture capital when the dot-com bubble burst in the late ’90s and I quickly pivoted to covering private equity. I had an idea of what private equity was, but I took “a fake it until you make it” approach to this new, daunting beat. I wasn’t sure how I was going to go about getting “high powered” people to let me in.

In 2003, I was sent to cover a new type of event ACG was trying called ACG Capital Connection. This was the first time I remember meeting Jay Jester, one of the organizers of the event. Despite my being a newcomer, Jester treated me like he treated every other person he comes across: with respect and kindness. He had a sincerity to him that I was finding rare in the industry at the time.

This section of the report originally appeared in the Spring 2024 issue of Middle Market DealMaker.

Photo by Anna Barzin.

For this story, I spoke with Jester in February about my first impressions, his time in the industry and his connection to ACG.

“ACG needed a new growth engine, so Stuart Mathews [president of Metapoint Partners], Ben Procter [a senior partner with Watermill Group] and I came up with the idea to organize what was basically a ‘private equity trade show,’” recalls Jester. “We worked with Bill Padnos, who ran InterGrowth [now called DealMAX] at the time, to launch the first Capital Connection at InterGrowth in 2003.”

The group sold Capital Connection tables for $495 each to about 30 private equity groups, Jester recounts. Each of those groups put out various product samples and brochures, “like they do at trade shows,” he says. “The Capital Connection concept took off very quickly. Within a couple of years, just about every chapter added one to their annual agenda and the regions began organizing larger events.”

It was ideas like this and his ability to foster strong relationships that pushed Jester into quickly becoming an integral part of the ACG fabric—and helped him to build a highly successful 30-plus-year career in the private equity industry.

An ACG Impact

Jester’s lasting impact on ACG reaches far beyond Capital Connection. He was also part of the team that founded the ACG New York Wine Tasting event. Around 2005, the Boston chapter he was part of had grown larger than ACG’s New York City chapter. ACG Global asked some of the ACG Boston board members to travel to New York and help the local chapter boost its numbers.

“It was hilarious and really fun for a bunch of Boston guys to roll into a New York ACG board meeting, offering our ‘help,’ especially in the wake of the 2004 Red Sox World Series,” he says.

“We mostly talked a bunch of sports trash but then got down to business and all came up with the idea for the wine tasting event. Trash talk aside, the ACG Boston/New York partnership was awesome and well ahead of its time. We later co-hosted ski events and I always recall each chapter going out of its way to welcome visitors from the other,” Jester says. Many years later, when the wine event became a huge success, the New York board always let Boston-based Audax Group, where Jester previously worked, participate because of the firm’s role in founding the event.

Around 2011, Jester was also tapped to be an ambassador when ACG decided to expand internationally. Invited by Pam Hendrickson, vice chairman of The Riverside Company, to join the so-called ACG Euro Tour, the pair traveled to several European cities to launch chapters.

“I remember the Wi-Fi going out on a train we were on, so we played ‘Name That Tune’ with a whole bunch of people on the train. We laughed our heads off,” says Hendrickson. “With Jay’s easy-to-be-with personality, smart ideas and humble demeanor, he is an easy pick for just about anything.”

All of these contributions were predated by one of his very first in the early 1990s, when Jester would also find himself leading the charge in creating Tampa’s ACG chapter. When Jester moved to Tampa to join Florida Capital Partners in 1992, he left his Charlotte ACG chapter to learn there was no Tampa counterpart. Jester—along with Dave Felman, a lawyer with Hill Ward Henderson, and Penny Parks, CEO of Links Financial—set out to fill that gap.

“This was pre-internet. You needed a way to find a network and deal flow, and ACG had to be part of that equation,” says Jester. “We knew that Tampa would be a great market, but we also knew that it would take a ton of time to get the chapter rolling, and we all had day jobs. I made the mistake of stepping out of the first meeting to take a quick call. When I returned to the room, I learned that I’d been elected the first president of ACG Tampa. It was a lot of work, but the organization helped me connect with the entire Gulf Coast deal community.”

Jester’s Rise in Business Development

Jester’s passion for ACG was a gift to the organization. However, the benefit was mutual. ACG has been a big part of Jester’s career and life as he rose to be one of the best original business development people in the business. It was Jester, notes Hendrickson, who first coined the phrase “ACG: All the people you need to know, before you need to know them.”

“Each time I moved to a new city, ACG became the foundation of my local network,” says Jester.

Jester’s career began in the Southeast. After graduating from University of North Carolina at Chapel Hill, he landed a job at Bowles Hollowell Conner & Co. in Charlotte, North Carolina, in 1990. BHC was one of the early non-Wall Street M&A boutiques. Jester worked for two years as an analyst at the firm. He also worked closely with Chris Williams and Hiter Harris, who later went on to found Harris Williams. Jester says he was happy at the time but really had a love for small businesses and wanted to do more to help them.

Raised in Greensboro, North Carolina, Jester developed a love for small businesses through his own family’s company. After World War II, Jester’s grandfather founded a business selling class rings to college students. Over the years, the company evolved into a promotional products distributorship. “I worked most summers and many holidays in the business, which was HQ’d in my grandparents’ basement,” says Jester. “Learning the nuances of a family business and seeing how my grandfather and father loved their employees, their customers and their suppliers really shaped my career.”

After completing his analyst rotation in Charlotte, an opportunity arose to interview with Florida Capital Partners, the small deal affiliate of Chemical Venture Partners in Tampa. “They were an emerging firm and they wanted someone to do business development. One of my fellow analysts, Mike Peters, made the introduction and I pretty much accepted on the spot,” says Jester. “The biggest gift was that I got to be Glenn Oken’s wingman.

Glenn was the OG pioneer of the mid-market BD partner. It was the early 1990s, and the middle market was just getting going. Today, every firm knows how critical BD is, but it was still a new concept in 1992. To this day, I believe that Glenn is the best, the most creative and most sincere connector in the entire middle market. Working for Glenn was a game-changer for me.

He’s incredibly smart and he’s genuine. He wants to know about you. He’s a super impressive person and I am glad ACG brought us together.

Pam Hendrickson

The Riverside Company

Making Moves

Eventually, Jester made his way to the Audax Group, a move facilitated in part by ACG.

Jester met Audax’s founders, Geoff Rehnert and Marc Wolpow, at InterGrowth right when the pair announced they were leaving Bain Capital to start a new firm. Rehnert had built a strong personal brand within ACG and he knew that robust deal flow would be critical to the launch of the equity business at Audax. They asked Jester to join the new venture in Boston.

At this point, Jester had a big decision to make. He had already moved his wife, Janice, from North Carolina to Florida. This time, the change meant moving his now-pregnant wife and two children from Florida to Massachusetts, where they would once again start over.

“I’ve been blessed with awesome partners over the years, but there is only one Janice. We will be married 31 years in June. We had a great life and a great community in Tampa, but getting in on the ground floor of the Audax story was a once-in-a-lifetime opportunity,” Jester says. “Aligning with Geoff and Marc was the easy part of the decision, but moving my young family up to the land of ‘The Frozen Chosen’ was the challenge. Janice made it happen. And, of course, I found a network and a new home with ACG.”

Jester had an extremely successful 20-year career with Audax. These contributions are memorialized inside the watch that Jester’s partners gave him as he headed back to North Carolina to begin his new adventure with Plexus Capital, an SBIC fund, in 2019. During his two decades in Boston, Jester led a team that sourced almost 25,000 transactions from 2,520 different firms and 6,924 individual contacts. As of March 31, 2019, these sourcing efforts yielded 124 closed platform deals and 756 add-on acquisitions.

“The impressive thing about Jay is he’s always reinventing himself. It’s not only that he has great sales skills, it’s that he has great relationship skills,” says Riverside’s Hendrickson. “It works for him in deal sourcing as he did for Audax for so many years, and it works for him with Plexus as both a partner and a fundraiser. He’s incredibly smart and he’s genuine. He wants to know about you. He’s a super impressive person and I am glad ACG brought us together.”

Jester left an indelible impression on all those who knew him at Audax. “I’m not sure if there’s anyone in this industry who is as well networked or has the depth of relationships that Jay has across the industry. He takes the time to know people at a personal level and develop genuine, long-term friendships,” says Young Lee, a partner and co-president of Audax Private Equity. “What really distinguishes Jay—in an industry in which relationships can often seem transactional—is his authenticity. It goes far beyond the Southern charm you might expect from a proud North Carolinian. He really cares and it comes through in everything he does, from his relationships and his attention to detail to his enthusiasm for the job and his unique ability to make everyone around him more effective. It’s infectious.” Lee stresses the positive impact that Jester had on Audax Private Equity. “I’d argue that our team-based approach remains one of the enduring legacies of Jay, our founders and our earliest employees,” he says.

I’m not sure if there’s anyone in this industry who is as well networked or has the depth of relationships that Jay has across the industry.

Young Lee

Audax Private Equity

When he made the bold move to join Plexus Capital after 20 years at Audax, Jester was brought in to launch a control equity fund, which closed at $204 million in 2022. Michael Painter, co-founder and managing partner with Plexus, recalls meeting Jester around 2007 or 2008 and their early conversations about the business side of Audax. “He was always so gracious about spending time with me,” remembers Painter. “He was always willing to share best practices and be helpful. In 2016, we said, ‘You need to start a buyout fund for us.’ He was such a great fit.”

A lot went into the decision to move back South. Jester had been in Boston for 20 years and had recently turned 50. “We were new empty nesters. I also lost my father to a long battle with Alzheimer’s a few years earlier. My life has been a spectacular and delightful journey, but Dad’s passing was a powerful reminder that it is not an endless journey,” says Jester. “The ‘second chapter’ at Audax worked out about a thousand times better than I could have ever dreamed, and I felt like I had gas in the tank for another adventure. Plexus caught me at the perfect moment. I am super excited to be back in the small market. I am trying to take the many lessons learned and apply them again. It’s energizing and often terrifying to be running a fund and building a firm, but it’s working and it is great fun.”

In April, Jester marked five years at Plexus. The firm has an internal channel used to share accolades for when employees do great things.

Despite being fairly new to the firm, Jester has racked up more kudos than anyone else. “Our firm can’t even remember life without Jay. And he has such deep relationships,” says Painter.

Many of those relationships were established through Jester’s involvement with ACG. “ACG changed my career and arguably my life. A huge percentage of my very best friends are ACG members,” says Jester. “ACG was an anchor for me in four different cities and helped me build a brand and a network very quickly.”


Danielle Fugazy is a freelance writer who has covered private equity for more than 20 years. She is based in Glen Cove, New York.


Middle Market Growth is produced by the Association for Corporate Growth. To learn more about the organization and how to become a member, visit www.acg.org.