Roach-Infested Jobs Spurred a $60K-Month Cleaning Empire

Skyler Sullivan’s Journey from College Graduate to Cleaning Business Owner

Skyler Sullivan never envisioned himself in the cleaning business. In 2018, fresh out of college and burdened with student debt in Omaha, he turned to odd jobs on Angi (formerly Angie’s List) to make ends meet. His initial experiences were far from smooth—roaches scuttling across floors, moldy kitchens that cleaners refused to finish, and angry clients demanding refunds. Despite these challenges, Skyler remained determined. He spent nights refining his process, weekends recruiting reliable help, and mornings handling urgent calls. Within two years, his side hustle, Nebraska Elite Cleaning, had grown into a $60,000-per-month operation serving homes and businesses across three counties.

Embrace Early Mistakes as Learning Opportunities

Skyler’s first job in spring 2018 ended with him on the phone at midnight, apologizing and offering a partial refund to a homeowner on 72nd Street. The cleaner he hired had fled at the sight of mice. Rather than see failure as a setback, Skyler documented every misstep—what went wrong, why roaches were overlooked, and where scheduling broke down. He created a simple “Post-Job Review” form in Google Sheets. After each cleanup, his team logged issues and brainstormed fixes over Sunday video calls. That relentless focus on learning turned early disasters into a rapid-fire education in quality control and client communication.

Lesson: Track every failure in detail so you can turn mistakes into your fastest route to improvement.

Recruit and Train for Consistent Quality

By late 2018, Skyler knew he couldn’t scale alone. He posted ads on Indeed and Facebook in Douglas County, looking for “detail-obsessed” cleaners. He interviewed over 50 candidates, asking for real stories of problem-solving—like how they’d tackle a clogged drain or spilled paint. Promising hires went through a two-week paid training program he ran out of his North Omaha garage, covering EPA-approved products, customer service scripts, and time-management drills. Each new recruit shadowed a senior cleaner for three jobs before going solo. This structured onboarding cut re-do rates by 70% in six months.

Lesson: Invest in rigorous training and clear standards to ensure every team member delivers the same high quality.

Leverage Technology to Streamline Operations

Skyler embraced automation early on. In 2019, he integrated BookingKoala for online scheduling and Stripe for seamless payments. Clients in Lincoln and Bellevue could book deep-cleans or weekly services in under a minute. His cleaners received automated job reminders via SMS, including home addresses and special notes—like “avoid cabinet under sink” for homes with pets. Skyler also built a Slack channel for real-time issue reporting, so if a vacuum broke at a 50th Street townhouse, he could dispatch a replacement immediately. These tools shrank administrative work by 40% and boosted on-time arrivals to 98%.

Lesson: Use off-the-shelf platforms to automate scheduling, payments, and communication, freeing you to focus on growth.

Cultivate Strong Referral Networks

Rather than rely solely on paid ads, Skyler tapped into local professionals. He joined three chapters of BNI (Business Network International) across Omaha and Council Bluffs in 2019. By offering free monthly deep-cleans to top-referring real estate agents, mortgage brokers, and property managers, he earned warm leads for move-out services and open-house staging. One agent in West Omaha sent him an average of five new clients per month in 2020. Skyler also partnered with two independent senior-care providers, offering discounted recurring cleanings for their referral list of 200 families.

Lesson: Build mutually beneficial partnerships with complementary businesses to generate a steady stream of qualified referrals.

Expand Into Commercial Contracts Carefully

In mid-2020, Skyler landed his first commercial client: a private preschool near Midtown Omaha. He quoted $1,200 per month for biweekly cleanings of classrooms and play areas. Coordinating six cleaners across school schedules challenged his logistics skills; he had to map routes precisely and stagger shifts. When the school added a second campus in Lincoln in early 2021, Skyler negotiated a $2,500 monthly contract. He never took large contracts for granted—he personally inspected every commercial site quarterly, ensuring metrics like “no visible dust” and “floor streak-free” held at 99% compliance.

Lesson: Treat commercial clients as long-term partners—maintain rigorous oversight to protect high-value contracts.

Prioritize Recurring Revenue Models

Skyler observed that one-off deep-cleans spiked revenue but also stress. In 2021, he unveiled tiered subscription plans: weekly, biweekly, and monthly cleanings, with price breaks up to 25%. By December, 65% of his residential customers were on recurring plans, providing predictable cash flow. He used a simple email campaign in Mailchimp—“Lock in your preferred time slot for 2022”—to upsell existing clients before the new year. Those subscriptions underpinned his $60,000 monthly revenue by mid-2022 and slashed churn to under 5% annually.

Lesson: Design subscription tiers that lock in customers and stabilize income, so you can plan expansion confidently.

Maintain Personal Connection at Scale

Even as Nebraska Elite Cleaning grew past 30 cleaners and 1,000 clients by 2023, Skyler kept his personal touch. He sent hand-written thank-you notes to new subscribers and appeared at quarterly “town hall” breakfasts in Midtown coffee shops. He published a monthly newsletter featuring cleaning hacks, team spotlights, and client success stories—opening each email with a photo of his Golden Retriever, Maple. This community-centric approach kept his NPS score above 80 and encouraged word-of-mouth that no ad campaign could match.

Lesson: Cultivate genuine human connections—small gestures build loyalty that outlasts price wars.

Skyler Sullivan’s path from fumbling through roach-infested jobs to helming a $60,000-per-month cleaning enterprise shows that grit and structure can transform any side hustle into a serious business. His secret sauce wasn’t a radical innovation but a rigorous process: learn from failure, train relentlessly, automate intelligently, and nurture relationships. As you chart your own entrepreneurial course, remember that scaling isn’t about complexity but consistency. Master each foundational step before layering on new services or territories. With persistence and the right systems, your side hustle can outgrow your wildest expectations—maybe faster than you think.