How to Start a Gutter Installation, Repair, and Cleaning Business That Wows Customers | Aleks Krylov

Nov 28, 2025

Aleks Krylov, founder of Stern Gutters and a former Wall Street finance professional, shares his journey from finance to creating New Jersey’s only white-glove gutter service. He reveals how a frustrating contractor experience inspired him to fill a market gap with a focus on communication and customer service. Aleks discusses launching with limited capital, using gutter cleaning as a lead generator, and the importance of hiring experienced professionals. He also highlights the significance of company values and a unique 24-hour quote turnaround to stand out in the industry.

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ANECDOTE

From Frustration To Founding Stern Gutters

Aleks hired an experienced installer and bought a truck after a failed partnership attempt.
He started by knocking on doors and doing some free work to build credibility in the community.

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INSIGHT

Professional Communication Is A Competitive Edge

Aleks blends Manhattan-level professional communication with hands-on field expertise.
Using real people plus tech improves responsiveness and differentiates a home-service brand.

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ADVICE

Use Cleanings As Diagnostic Service

Treat gutter cleanings like diagnostics by checking pitch, seals, downspouts, and fascia.
Over-service the first visits to build trust and make future maintenance faster and cheaper for you.

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Aleks's Wall Street to Gutters Origin

02:08 • 4min

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Stern Gutters: Mission and Growth

05:48 • 4min

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First Steps: Launching with Limited Capital

09:20 • 2min

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Using Cleanings as Diagnostic Lead-Gen

11:39 • 6min

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Early Customer Acquisition Channels

18:07 • 2min

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Startup Costs and Equipment Choices

19:50 • 3min

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Hiring Challenges and Screening

23:07 • 5min

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Instilling ICUCOP Company Values

27:46 • 6min

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Field SOPs and Office Tech for Service

33:56 • 4min

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The 24-24-24 Quick Turnaround Rule

#693 How did a Wall Street finance pro turn a simple gutter repair problem into New Jersey’s only white-glove gutter service? In this episode, host Brien Gearin sits down with Aleks Krylov, founder of Stern Gutters, to break down how to start a profitable gutter installation, repair, and cleaning business. Aleks shares his journey from Wall Street to home services, revealing how one frustrating homeowner experience sparked a premium, communication-driven company now serving 2,000+ customers. He walks through the essentials of launching a service business — from smart lead-gen and hiring experienced technicians to leveraging technology and delivering standout customer experience. If you want a clear roadmap for building a high-demand service company, this episode delivers the blueprint!

What we discuss with Aleks:

+ Wall Street to gutters journey

+ Identifying a major market gap

+ Launching with limited capital

+ Using gutter cleanings as lead-gen

+ Building trust through communication

+ Hiring experienced installers

+ Instilling company values (ICUCOP)

+ Fast 24/24/24 quote turnaround

+ Multi-channel lead generation

+ Expanding into broader exterior services

Thank you, Aleks!

Check out Stern Gutters at SternGuttersNJ.com.

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