Chip Ottley
About Chip Ottley
Chip is an operational problem-solver who thrives in the messy, uncharted stuff—lateral thinking, abstract leaps, navigating the unknown. He's turned chaos into order in IT systems, competitive intelligence, and even de-escalation training. He has a knack for simplifying the complex and teaching others to think differently, all while being the go-to guy for execs and entrepreneurs when they’re stumped. Plus, he's neurodivergent (bipolar autism), which he has harnessed as a superpower—his “rational mastermind” and “truth seeker” traits shine through in how he approaches life. Chip got grit from growing up in poverty, street smarts from his varied past, and a heart for helping people tackle problems they can’t solve alone. That’s a rare combo.
Chip is also the founder of My People LLC, which provides a range of operations consulting services designed to enhance business efficiency and performance. Offerings include IT support to streamline technological infrastructure, competitive intelligence training to empower teams with unique insights, and technical training to boost operational capabilities. Catering specifically to B2B clients, My People LLC offers a strategic advantage by delivering cost-effective solutions that leverage Chip’s extensive skills without the complexities of traditional employment models. More than just a service provider, My People LLC acts as a vital partner, helping businesses save money and resolve operational challenges with tailored, impactful expertise. Chip isn't just a contractor; he's a strategic asset who saves money and solves headaches.
Professional Journey
A 43-year-old problem solver who’s spent a lifetime turning chaos into order—both in his own life and for businesses around the globe that needed a sharp mind to cut through the noise. Chip’s professional journey began at 13 years old, laying tile in Florida, paying taxes by age 14, working in fast food until he got his driver’s license, then it was onto his first passion (cars) as a car lot porter, and as a valet in Sarasota - driving the world’s priciest cars.
High school wasn’t teaching him what he wanted to learn, so Chip withdrew himself and attended Western Washington University, studying film and television. He marshaled private aircraft at an FBO in Bellingham, while starring in commercials (Microsoft, AT&T), getting paid extra work in a feature film with Angelina Jolie, starring in theater gigs from Washington to Miami, and working in production on a major network TV series in Chicago. Life hit hard at 20 when his dad bled to death in his arms and his sister died soon after. He stumbled—booze and bad choices landed him in jail—but he clawed back.
After his first son was born, Chip passed on a “Mad TV” offer from a Hollywood exec, to build a stable life. He bartended to pay the bills, while attending Hillsborough Community College for IT (CompTIA A+, Security+, Cisco CCNA, MECP). By the time he finished school, he secured a career as a systems engineer at a MSP in Tampa, building cloud infrastructure and running onsite IT for the National Forensic Science Technology Center.
Later trained by CA Technologies in San Francisco, he became a CA Nimsoft certified enterprise network monitoring admin and engineer, consulting and training for global enterprise giants both remotely, as well as flying internationally to fix their toughest messes - all while winning full custody of his first son, and having a second boy, diagnosed with severe autism - and adding VMware VTSP 5, AWS Cloud Practitioner, and SAFe POPM 6 Product Owner/Product Manager creds to his resume along the way.
During all of this, while engineering for a client (who would become Chip’s next boss and mentor), Chip was recruited to teach competitive intelligence at the USF MUMA College of Business - for the US intelligence community and global banking giant Citigroup.
Grand Mal seizures revealed epilepsy and bipolar autism, forcing Chip to retire at 33. Disabled but not done, he’d already bought a house in 2014, leaning on savings, SSD, and his wife’s nursing gig to allow him the freedom to care for the kids. However, divorce and a brutal custody battle stripped it all away—house, savings, stability, sanity.
Ten years of meds and therapy didn’t fix him, so he took charge: ketogenic living, no excuses, and a new start with My People LLC. Now, at 44 (as of May 4th), Chip is divorced, solo, and starting over—again. He’s lost everything twice, but he’s built order from ashes every time. That’s why he’s damn good at doing it for others. With a track record of successfully navigating the real world, including: the criminal and family court systems, the entertainment world, enterprise IT systems, network engineering, and competitive intelligence - plus a knack for teaching, training, communication, and web development, he’s the fixer you call when problems pile up and time’s running out. Honest, loyal, and real - he sees the world as it is and makes it work as it should. If you’ve got money and problems, but no time or loyal, dependable, agile people you can trust, Chip has the grit and the smarts to sort it out. Let’s talk.
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