Arnie Bellini: The Show Must Go On

Amid Thoma Bravo's buyout of ConnectWise, the software company's CEO crown is transitioning from Arnie Bellini to Jason Magee. It's a dramatic moment for the managed IT services provider (MSP) market, a global industry that Bellini and the ConnectWise software business has helped to define, shape and scale for nearly four decades.

To be clear: Bellini is not retiring. He remains an advisor to Magee and ConnectWise. And he surely has some IT-related next moves on his personal road map.

Still, the company sale and CEO transition is a major inflection point for the industry. And an important moment to put Bellini's industry legacy into proper context.

Arnie Bellini: Market Builder

Bellini is one part Henry Ford and one part P.T. Barnum. An automation expert who helped partners to assemble and activate IT service catalogs worldwide. A showman who attracted (and retained) a crowd. And a fierce competitor who occasionally sparred with rivals.

Bellini has driven managed IT services and monthly recurring revenue (MRR) financial models into the SMB sector for more than two decades. In other words, he was a decade ahead of major technology titans (Michael Dell, Steve Ballmer, John Chambers and others) -- each of whom took far longer to understand how managed and cloud services would transform and empower small businesses worldwide.

Along the way, Bellini delivered his message with a blend of deep market analysis, a few data points seemingly pulled from a virtual top hat, and pure showmanship.

Not familiar with Bellini? Think of him this way: In the financial world, Berkshire Hathaway investors flock to Nebraska each year to hear directly from the Oracle of Omaha, aka Warren Buffett. In Silicon Valley and the San Francisco Bay Area, Apple fanboys still wax poetic about Steve Jobs keynotes, secretive product launches, "and one more thing."

And in the MSP ecosystem, thousands of business owners head to ConnectWise's IT Nation conference in Orlando each November -- eager for the latest vision statements from Bellini and thought leaders from across the business world.

The Boss and the Ball Player: Rolled Into One

Perhaps Bellini's best trait is his ability to see and actually shape the big picture from his seat in the owner's box, before heading down to the dugout, walking up to the batter's box, and personally executing his game plan on the field.

It's somewhat akin to George Steinbrenner building the Yankees, and Derek Jeter taking his swings at home plate, and then vacuuming up ground balls at shortstop. Bellini plays all of those positions -- all at once.

Plenty of executives talk about business automation, but Bellini personally installed and configured ConnectWise's software for scores of partners two decades before digital transformation became a mainstream term.

Admittedly, Bellini isn't perfect. No business leader is. Steve Jobs had his infamous temper, frequently shifting from a charming personality to a condescending intimidator at a moment's notice. Warren Buffett has a technology investment blindspot (among his bad bets: IBM).

Bellini's approach to business at times rubbed some rivals and partners the wrong way. Stress levels in and around his IT Nation keynote preparations sometimes ran extremely high. Impulsive decisions sometimes weighed on long-term company planning. Occasional cease-and-desist letters from Tampa to rivals typically included nuclear threats.

However, each of those traits point to an undeniable truth: Bellini is extremely protective of ConnectWise and the business-building partners within IT Nation. To him, it's all family. And you never go against the family.

Still, Bellini balanced that family-first business approach with alliances. Much like the late Ray Noorda of Novell, Bellini publicly preaches coopetition (cooperating and competing with rivals) while occasionally mixing it up with rivals behind the scenes.

One trait -- more than any other -- kept ConnectWise in growth mode. It involved Bellini's fanatical focus on partner success. That partner obsession came from Bellini's own experience joining executive peer groups early in his career. And he attended conferences like Novell BrainShare -- a pioneering event in its day -- just as PCs were shifting to local area networks.

BrainShare, in some ways, provided the creative spark for ConnectWise Partner Summit -- which morphed into the larger IT Nation conferences and peer groups.

ConnectWise: Humble Beginnings

Arnie and brother David Bellini, two certified accountants, had humble beginnings in the technology market. They originally built ConnectWise as an IT support business in Tampa, Florida nearly four decades ago.

During the company's early days, the brothers looked so young that they dragged their dad (a retired IBM salesman) to initial customer meetings. The brothers' unspoken strategy: With dad along, perhaps they could convince customers that the company had some experience in the IT market.

David was the conservative one, content to build an IT services business. Arnie had a flair for the dramatic, determined to branch out into software. Together, they marched forward -- supporting each other and their business through the ups and downs of life, family and multiple IT market shifts.

By the early 1990s, they were building a PSA (professional services automation) software platform to automate their own business -- and eventually sell to other firms. True believers included Linda Brotherton, one of the company's first hires and a key influencer for multiple decades at the firm. It's a safe bet that Brotherton is among the ConnectWise employees and alumni who are now enjoying the fruits of their labors. Indeed, more than 70 current and former ConnectWise employees will become millionaires when Thoma Bravo's buyout of the company is official.

ConnectWise: Beyond PSA Software

Fast forward to the early 2000s. IT solutions providers were beginning to adopt PSA in combination with RMM (remote monitoring and management) software. ConnectWise and early rival Autotask (now part of Datto) built beachheads across North America in the PSA market. RMM upstarts as Kaseya, Level Platforms and N-able Technologies (among others) were gaining ground in their market niche.

At first, Bellini partnered up with those RMM providers. But by 2010, he shifted the competitive landscape. ConnectWise spotted and invested in an RMM upstart called LabTech Software, while continuing to integrate with third-party RMM software companies. The race was on to create a complete business automation platform for MSPs and technology partners.

Among the key ConnectWise moves that turned heads:

Still, rivals and private equity firms reacted with multiple M&A deals. The MSP software market has shifted multiple times since that 2010 LabTech investment. Old rivals like Level Platforms and Zenith Infotech have largely faded away (though Level Platforms' software lives on at Barracuda Networks). New rivals like Datto and SolarWinds MSP have emerged. And entrenched competitors like Kaseya and Continuum continue to chug along.

What's the one thing all the major MSP software providers now have in common? The answer is private equity funding. That funding is to drive the next wave of R&D and acquisitions.

Arnie Bellini's Next Chapter

So what's next for Arnie Bellini? He's now an advisor to ConnectWise and new CEO Jason Magee. But that doesn't mean Bellini will fade from the market scene. In fact, I'd recommend you watch for a potential encore -- one in which Bellini helps to guide more executives on the road from entrepreneur to exit, while continuing to support the company he built, and its new CEO leader.