When Tim Taylor founded TaylorWorks in 1999, managed services as we know them today didn’t exist. Today, the company is a next-generation MSP run by a leader who essentially was raised in the channel.
But it wasn’t an easy start. Early on, Tim ran his fledgling company out of the trunk of his car, servicing clients who in many cases didn’t even have internet access.
“Back then, there were no MSPs. You were just called a computer company,” he recalled of the days before the internet. “I had a big law firm client down the street here for years, and the only internet connection they had was the main attorney’s AOL dial-up modem in his computer. So I helped them get their first website, domain, and, just about everything [technology-focused] in their office.”
From those early days of billing clients weekly out of his bedroom, Longwood, FL-based TaylorWorks grew into a multimillion-dollar MSP. Eventually, he sold the business to his sons, Jared and Brandon Taylor. Today, the company’s leadership reflects the next generation of ownership — and a new vision for growth.
Jared Taylor’s Path to Leadership
Jared Taylor, now CEO and president, grew up in the business. He started as a high schooler, entrusted by his father to do Windows updates for clients. The task forced him to embrace taking on responsibility early.
“Back then, when you had DSL [digital subscriber line], Windows updates would take three hours per computer. We had to go in after hours,” Jared said. “I was 16, and [Tim] gave me the alarm code and the key to the building. After I updated all the computers, I’d leave a note on somebody’s desk, ‘I updated your computer this weekend.’ Then, I turned the alarm on, locked it up, and left the building.”
Jared Taylor
Jared later worked outside of the family company as a network administrator for a 500-employee HVAC contractor. There, he made a mark by leading a major digital shift for the company. “I helped them transition from paper to paperless,” he recalled. The experience gave him a grounding in business processes, financial oversight, and employee management. He brought these skills back when he joined TaylorWorks full time.
By the time he assumed ownership in 2024, Jared was already well established as a team leader. “I was already president of the company at the time,” he said. “All of the employees have stayed since the transition. Everything’s been going really well.”
Since taking the helm, Jared has leaned heavily on fiscal discipline. “Other MSP owners will resonate with this: I was able to cut almost $20,000 in monthly spend without having to let anyone go. That’s either by finding better tools or renegotiating contracts,” he revealed.
Looking forward, TaylorWorks aims to grow through emphasizing the company’s “sales roots,” he said. “Even though I’m a young guy and you would think I would only want to use technology … you still have to get to know small business owners.”
Brandon Taylor Brings a Channel Perspective
Jared’s younger brother, Brandon Taylor, took a different path. Passionate about acting and theater, he pursued a career on stage before coming back to his family’s channel focus, but on the sales side. He is currently channel development manager at Kaseya, where he connects with vendors and MSPs across North America.
Brandon Taylor
“My full-time job is basically meeting and working with different vendors, seeing what other tech is out there, what’s hot, what’s not, who pays their bills, and who doesn’t,” Brandon said. “We see the good, the bad, and the ugly.”
That exposure, he explained, strengthens TaylorWorks’ partnerships. “I was honored to get the opportunity to buy into the business. In my career, when I meet with other MSPs, their faces just light up immediately when they realize I have skin in the game.”
Brandon also underscored how critical vendor relationships can be for MSP success, as well as training your engineers to be a “window” into more sales. “Over the years, I’ve seen a lot of people send the least personable person on site. That then becomes the client’s experience with your company. Just be conscious of who you’re sending.”
Tim Taylor’s Passion for Consulting
Although he stepped back from day-to-day leadership, Tim Taylor has remained deeply connected to the MSP community. He has run Tim Taylor Consulting Group for the last decade, and his book, How to Start and Run a Successful I.T. Company Without Losing Your Shirt, was published in 2016.
Tim Taylor
“I really enjoy helping MSPs. My market is the guy just getting started or the guy’s got one or two employees,” he noted. “I can help them grow to a $2.5 million MSP like we did.”
Tim’s motivation comes from firsthand experience. “About 90% of MSPs never break $1 million in revenue, and there’s no reason for that,” he said. “I’ve been consulting a couple of guys for about three years, and one of them is doing over $600,000 a year his third year in. He’s doing what I was telling him to do, he’s marketing himself, and he’s not trying to do everything himself.”
Tim sees consulting as a way to give back. “I really have a passion for helping MSPs grow because I’ve done it from the ground up back when this was an infantile industry,” he explained.
Next-gen Advice for MSPs
Since the transition, there’s been plenty of hard-earned wisdom for Jared. For one thing, he doesn’t want business success to hinge on a handful of major accounts. By broadening the client base, TaylorWorks can absorb churn more easily and avoid painful cuts.
“What I’m trying to do for the vision of the company is not take such a big hit with some of these big clients,” he explained. “If I lose a little bit here, it doesn’t hurt the bottom line as much.”
(from left): Brandon, Tim, and Jared Taylor
Brandon, meanwhile, pointed to the importance of commitment and trust in building long-term success. “I take things more personally than my coworkers do,” he admitted. “That’s one of the reasons I’ve probably started to gain a relatively big tenure, which is seven years now. A lot of salespeople jump and move every two to five years, but I’ve stuck with it.”
Together, the brothers’ perspectives highlight two essentials for MSPs: Diversify to stay financially resilient and invest personally in the relationships that keep clients and partners loyal.
The Next Generation of TaylorWorks Success
From Tim’s early days building the business without a PSA to Jared’s cost-cutting to Brandon’s dual role in the channel, TaylorWorks has embraced both continuity and change.
“Most of our success over the last five months — I would say more than 60% — has just been handshaking and word of mouth,” Jared shared. “Sure, there’s a new wave of young owners, but when it comes to MSPs, you still have to be a trusted person.”
Tim made it clear that he believes TaylorWorks is in capable hands. Jared has earned employees’ respect by working in every role before stepping into ownership. That, together with Jared’s focus on financial discipline and growth, assured Tim of a smooth transition.
Tim also expressed pride in Brandon’s career trajectory in the channel, noting how his perspective on vendor relationships and industry trends adds valuable insight to TaylorWorks. Seeing both of his sons bring their own strengths to the company confirmed that the leadership shift has prepared the business for its next chapter.
The company’s journey demonstrates what MSPs everywhere can take to heart: Succession can be seamless if grounded in trust, experience, and the willingness to keep evolving.
3 Lessons MSPs Can Learn from TaylorWorks
- Sales Still Starts with a Handshake: Technology helps, but relationships close deals.
- Diversify Your Client Base: Don’t rely too heavily on “elephant” clients. More smaller clients create stability.
- Hire for Personality First: Tim emphasized that customer-facing roles are about trust and rapport.
Anjali Fluker is senior channel editor for The ChannelPro Network, where she covers news, trends, and best practices for the MSP community. She specializes in telling the stories that matter to IT providers serving the SMB market. When she’s not reporting on the latest in managed services, she’s connecting with channel pros at industry events across the country.
Images: Anjali Fluker/ChannelPro, TaylorWorks
