A Bartender Turned His Window Cleaning Hustle Into a Six-Fig Business

For Kyle Ray, there are few things more satisfying than cleaning a dirty window.

It’s “instant gratification,” the Texas native told Business Insider, and something he first experienced in high school while working odd jobs. “It’s one of those things that seems mindless and easy, but it’s actually rather complicated and takes skill, and I just enjoyed it a lot.”

In 2007, Ray needed work. He’d dropped out of college to start a real estate business with a friend that ultimately failed, and then spent about a year working a 9-to-5 cubicle job that drove him crazy: “I didn’t like having a boss.”

He quit, picked up night shifts bartending and waiting tables, and dedicated his mornings and afternoons to building a window cleaning business.

While he had some experience from his teenage years, he needed to refine the skill.

“The fastest way for me to gain as much knowledge as I could as quickly as possible was to actually work for somebody,” he said. “So I worked for a window cleaning company for like three months and then I was like, ‘OK, I got it.'”

Ray bought about $100 worth of equipment at Home Depot, loaded his truck, and drove to strip malls all over Houston. He went storefront-to-storefront, asking general managers if they needed their windows cleaned.

His first client was a massage parlor.

“I walked in the door because their windows were filthy and I asked them if they’d like a quote,” he recalled. “They told me no. They do it themselves. I told them, ‘Well, you didn’t do a really good job, and I can do a better job. If you let me do it, it’s only 15 bucks.'”

Ray, whose second and third clients were a hair salon and a wing shop, called his side hustle Geek Window Cleaning.

Pivoting from commercial to residential work

Ray spent about a year cleaning brick-and-mortar storefronts. Residential didn’t cross his mind until the general manager of one of his commercial clients asked if he’d clean his house windows.

His first residential job took three hours and earned him about $300.

“That’s when a lightbulb went off and I was like, ‘I need to get good at residential,'” said Ray.

While more lucrative than commercial jobs, it requires more skill.

“Your typical commercial locations have big pieces of glass. It’s very easy to clean. There are no obstructions in front of the glass,” he explained. “Residential is smaller. It can be single hung. It can be a divided light window — the little squares, and those little squares vary in size. They can be three inches big, six inches big, 10 inches big. Then, you have screens that you have to deal with, and you have multi-level, so two-story or three-story windows. The difficulty factor explodes when you’re doing residential.”

He also found it harder to land clients, at least in the first couple of years.

“I would go out and knock doors, and I would get two people in a day, but then I wouldn’t get anybody for like a week or two,” said Ray.

He wasn’t discouraged because he knew he was onto something. He decided to drop his commercial clients and go all in on residential.

Growing to six-figures using SEO, a unique pricing structure, and ‘unreasonable hospitality’

For years, Geek remained a side hustle for Ray.

“I enjoyed the work a lot, and it was bringing in OK money, but it wasn’t enough for me to quit waiting tables and bartending,” he said. “I was working seven days a week. It started to become a hamster wheel that I got myself into, and I couldn’t figure out how to grow fast enough to produce the level of income I needed to leave these other jobs.”

That changed around 2014 when he started figuring out how to leverage SEO.

“I started reading a lot of books about it, and I started building my website and doing all the SEO stuff that you would do back then,” he said. “I was getting more consistent jobs and more referrals from customers because we were doing a really excellent job for them. And then, in 2015, if you were Googling ‘window cleaning Houston,’ we were showing up in the No. 1 position. Then we started getting really busy.”

Around the same time, he was rethinking his pricing structure. A major benefit of his commercial work was the consistency: Once he locked in a client, they’d typically want him to return weekly or every other week.

His residential clients were more sporadic. To encourage them to set up recurring cleanings, he experimented with a pricing model in which clients would get a discounted price if they paid a monthly fee for a set number of cleanings, rather than hiring him for one-off jobs.

“I’ve been basically tweaking that program since 2015, and I’d say probably in 2019, 2020 is when I really figured it out — how to sell it and how to get people set up,” said Ray. “And then we started really cooking with fire.”

Geek’s “Always Clean Program,” or ACP, puts customers on an automatic cleaning program. Their monthly rate is determined by the services they select — Geek has expanded to offer pressure washing, gutter cleaning, and roof cleaning — the size of their home, and the frequency of the cleanings.

Ray, who has been in the business for nearly two decades, believes that maintenance programs, rather than one-offs, are the future of window cleaning: “I think people are catching on now, and there are a couple of people doing it, but back when I started doing it, everybody thought I was crazy.”

He also believes in excellent customer service. One of the business’s core values is what he calls “unreasonable hospitality,” which he describes as “transforming ordinary customer interactions into extraordinary experiences.”

He trains his technicians to go above and beyond.

“If we show up to someone’s house and their garbage cans have been dumped, we just go grab them and we’ll be like, ‘Hey, where do your garbage cans go?’ Or, ‘Hey, this light fixture was really dirty. We just went ahead and cleaned it,'” he said. “We do unreasonable things to make sure that you’re super happy.”

Hospitality is in his blood. He grew up watching his mom, who ran a bread-baking company, take supreme care of her customers. He further bought into the idea of providing exceptional customer care after years of waiting tables.

“You can be an asshole waiter. Or, you can be a really hospitable, friendly waiter — and you’ll make a lot more money,” he said.

Ray has teams of technicians in Houston and Austin, where he and his wife currently reside, and plans to expand to Dallas in 2027.

The business generated six figures in revenue in 2024 and is on track to exceed $1 million for the first time in 2025. Business Insider confirmed these details by reviewing his 2024 P&L and ServiceMonster dashboard.

Ray has big goals that he plans to achieve by implementing his Always Clean Program, phasing out one-off cleanings, and continuing to provide unreasonable hospitality.

“The goal is to go to $40 million a year in revenue in five years and $100 million a year in revenue in 10, and then expand out of state,” he said. “We know how to get there and and we’re just going to go for that and see what happens.”