Way Out #22: He Was Putting Payroll on Credit Cards: Then His Son Was Born Nine Weeks Early with Brian Best
Imagine turning 50 knowing you have successfully been your own boss for exactly half of your life. Imagine being able to run your business from an RV while taking multi-week cross-country road trips with your family. If you need to step away for an extended period, your team will keep the ship afloat without you missing a beat. Best of all, you no longer stress about a "feast or famine" income because your monthly recurring revenue easily covers every single bill before the month even begins.
This is the reality for Brian Best, the founder of Best Max, a thriving Kansas City-based IT managed services company. But building a life where his income is decoupled from his time wasn't an overnight success; it was a grueling, decades-long journey of trial, error, and radical pivots.
The Ordinary World and the Dad Advice
Long before he was an entrepreneur, Brian was simply a self-proclaimed "computer nerd" who fell in love with a garage-sale computer at the age of ten. While he loved programming, the traditional college path wasn't for him. He dropped out of his computer science track after a frustrating 2:00 a.m. coding session where a passing student pointed out he had spent hours agonizing over a single missing semicolon.
Trying to figure out his next move, he followed his father's lifelong advice: get a safe, secure government job with a pension. Brian landed an IT role working for a local school district.
Brian’s Call to Adventure
It didn't take long for the "safe" path to shatter. He found himself drowning in bureaucracy, politics, and a glaring lack of impact.
His ultimate breaking point came in two parts. First, he was tasked with researching a new email system for the district. He and a team spent weeks testing options, setting up servers, and compiling a definitive recommendation, only to have his boss completely ignore the findings and stick with the old system. Second, he watched an entitled superintendent demand a top-of-the-line, expensive laptop setup just to check emails, while the students in the classroom across the hall were forced to use decrepit, falling-apart 10-year-old machines.
Disgusted by the wasted effort and entitlement, Brian decided he was done. At just 24 years old, armed with a book about starting a business that he had purchased in 1996, he walked away to become a "hired gun" fixing Mac computers.
Why Hustle Isn’t Enough
In the early days, Brian operated purely on hustle. He would put on a nice shirt, walk into creative agencies or print shops, hand them a cheesy, self-drawn business card, and ask if they needed their Macs fixed. To make ends meet, he spent 26 weeks out of the year traveling the country training people on computer repair.
Eventually, he saved enough to open a physical retail storefront in a college town. But this led to a massive realization: too much of the wrong business will kill you. He was drowning in low-margin warranty repairs and trying to compete with university student pricing on new hardware. He discovered the harsh truth of the 80/20 rule: 80% of his headaches were coming from the retail side that generated only 20% of his revenue, while 80% of his real revenue came from small businesses fully outsourcing their IT to him.
Then, in 2008, life forced a radical pivot. Brian's first son was born nine weeks early, requiring a terrifying six-and-a-half-week stay in the NICU. Practically overnight, Brian went from a workaholic entrepreneur putting in 80 hours a week to only being able to work 10 hours a week.
The Transformation and The Reward
Sitting in the hospital, Brian had an epiphany: he could no longer trade his time for money. If the business relied solely on his physical presence, it would fail.
He completely transformed his business model. He closed the retail store and pivoted hard into "managed services". Instead of charging an hourly rate when things broke, he started charging a predictable, flat monthly fee to proactively manage his clients' networks. Suddenly, his interests aligned with his clients: the fewer problems they had, the more profitable his business became. The exhausting "sine wave" of unpredictable income flattened out into steady, reliable recurring revenue.
Over the next decade, Brian continued to innovate. He built and spun off his own software tool, sold it to a larger company, and traded it for a W-2 salary to protect his employees. While the acquiring company eventually fumbled the product and fired him in the summer of 2023, Brian just laughed. Because he had spent years perfecting his recurring revenue model, Best Max was already generating more than enough to cover his entire salary.
Today, Brian runs his business from exactly where he wants to be—whether that is his home in the Northland of Kansas City or the passenger seat of an RV. He measures his success by his family's happiness and the ultimate freedom of knowing his time is finally his own.
Brian's Tips for Wayfinders
Stop trading your time for money.
The most liberating business decision Brian ever made was shifting from hourly billing to a flat-fee, recurring revenue model. Whether you are a creative, a consultant, or an IT professional, find a way to productize your value so your income isn't entirely dependent on how many hours you clock.Your talent alone is not enough to sustain a business.
Many professionals think that because they are great at their craft, they will easily succeed as entrepreneurs. But a business requires sales, marketing, human resources, and financial management. You must be willing to learn these systems or pay someone to handle them.Hire for your weaknesses, not your strengths.
If Brian could do it all over again, his first hire wouldn't have been another tech wizard who did exactly what he did. His first hire would have been an administrative assistant to handle the crucial, low-value tasks that he procrastinated on. Stop doing the work you hate; delegate it so you can focus on growth.
Follow Brian's Journey
If you want to connect with Brian, explore his transition to managed services, or check out his self-guided onboarding process, you can find him at BestMacs.com.
