Kyle Ray never felt comfortable in the classroom.
“I didn’t do great in school, and I was basically told, the best you can hope for is to be a manager of a restaurant,” he told Business Insider. “That’s just been an internal driver — like, ‘I’m going to prove this person wrong.’ And that still drives me really hard today.”
The entrepreneur, who turned his window cleaning side hustle into a six-figure business that services hundreds of clients across Houston and Austin, leveraged books to get ahead.
“I didn’t go to college and get a business degree, so I read a lot of books,” said Ray, who spent years bartending and waiting tables to pay the bills while slowly building Geek Window Cleaning. It took about seven years until he started earning enough income from his side gig to quit his service jobs.
Today, Ray reads at least a book a month — and he has a strategy that holds him accountable.
“My hack for reading is I put a $100 bill as my bookmark, and when I’m finished reading the book, I get to spend it,” he said. “It’s a good motivator.”
He can spend it on anything he wants, as long as it’s not work-related. Sometimes, he’ll add the bill from a book he’s just completed to his next book and save a couple of hundred dollars so that he and his wife can splurge on a fancy dinner.
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Ray, who now manages a team of employees, credits much of his business’s success to principles he’s picked up from various business and leadership books. His top picks are “Drive” by Daniel Pink, “Dare to Lead” by Brené Brown, and “Beyond the Hammer” by Brian Gottlieb.
He’s most looking forward to reading Phil Gilbert’s “Irresistible Change,” which will be released in late 2025.
Ray wants to develop his team as much as he does his business, and part of the promotion process requires finishing specific books.
“We’re not a window cleaning company; we’re a training facility that develops people,” he said. “My main goal is to make anybody who comes to work with us really successful.”
A key to success, at least in his eyes, is self-education.
“Every business owner should just be reading as often and as much as possible.”
