Told he’d never amount to more than a restaurant manager, this entrepreneur proved everyone wrong—and he credits one unconventional habit for his success.
Kyle Ray’s journey from struggling student to six-figure business owner is nothing short of inspiring. But here’s the part most people miss: he didn’t achieve it through traditional education or fancy degrees. Instead, Ray turned to an unlikely tool—books—to build his window cleaning empire, Geek Window Cleaning, from the ground up. And this is where it gets controversial: his secret weapon? A $100 bill.
Ray, who once juggled bartending and waiting tables to make ends meet, now manages a thriving business serving hundreds of clients across Houston and Austin. Despite early doubts about his potential, he channeled his determination into self-education, devouring business and leadership books to fill the gaps left by his lack of formal training. Today, he reads at least one book a month, thanks to a clever hack that keeps him motivated.
The $100 Bookmark Hack: Genius or Gimmick?
Ray’s strategy is simple yet brilliant: he uses a $100 bill as a bookmark, rewarding himself with the cash once he finishes the book. The catch? He can spend it on anything—except work-related expenses. Sometimes, he even rolls the reward into the next book, saving up for a splurge like a fancy dinner with his wife. But here’s the question: Is this a sustainable motivator, or just a temporary gimmick? Let us know what you think in the comments.
This approach isn’t just about personal growth; it’s woven into the fabric of his business. Ray views Geek Window Cleaning not as a window cleaning company, but as a training facility focused on developing people. He even requires his team to read specific books as part of their promotion process. His top recommendations? Drive by Daniel Pink, Dare to Lead by Brené Brown, and Beyond the Hammer by Brian Gottlieb. He’s also eagerly awaiting Phil Gilbert’s Irresistible Change, set to release in late 2025.
Self-Education: The Great Equalizer?
Ray’s success raises a thought-provoking question: In a world obsessed with degrees, is self-education the underdog strategy we’ve been overlooking? Ray certainly thinks so. “Every business owner should just be reading as often and as much as possible,” he insists. But is this advice practical for everyone, or does it only work for those with the discipline to stick to it? Weigh in below.
Whether you’re a budding entrepreneur or just looking to level up your skills, Ray’s story is a powerful reminder that knowledge—not credentials—is the ultimate game-changer. So, grab a book, find your own motivator, and start building the future you want. After all, if a former bartender can turn a side hustle into a six-figure business, what’s stopping you?
