Throughout high school I worked with my dad doing window washing and gutter cleaning. He was a fireman, and like seemingly all firemen, he had an entrepreneur side hustle: Steve's Window Washing and Gutter Cleaning. Beyond how to clean gutters here's what I learned about operating a gutter cleaning business.

  1. Homeowners have their own sense for what they think they should pay, and quotes for walkable roofs were much more inline with their expectations. When a homeowner thinks of their house, they seem often to think about it in terms of its size, which is fair, but not proportionate with the actual time it would take to clean their gutters. However, when it comes to gutter cleaning, valuing time is the name of the game - which leads to the next two points.

  2. Gutter cleaning is a race. In the midwest where I grew up, there is only about a two week period between "when all the leaves are down" and "first freeze". These two weeks were sun-up to sun-down work days, 7 days a week, because the amount you can make is directly tied to how many jobs you can squeeze into that window.

  3. Route density is your best friend. This is true in all contract work: you want to maximize the hours of your day that you can bill and driving between sites is not one of them (in addition to the costs of doing the driving). In lawn work, bad route density means you spend longer for the same amount of money (it costs you wasted hours). But in the gutter cleaning "sprint", your day is already fixed sun-up to sun-down, so the cost is missed jobs.

  4. Be diligent about when you can start. You have to wait until the leaves are all down, but this is not a single event across your whole area. We had routes in some cities that were ready to start days before other nearby cities. It was really quite odd, but being tuned into this allowed us to get through more jobs.

  5. Oak trees are a red herring. Oak trees hang onto their leaves longer than any other tree (at least it seems to me in the midwest... I'm not like a passionate tree trivia guy), well past first freeze and into winter. No need to wait for Oaks to drop their leaves (otherwise you'll never do the job). If there is a house with a lot of Oaks, suggest a spring cleaning as well.

  6. Be a great person. During phone calls, estimates, and billing, be nice! Be gracious. Be kind. Have a nice conversation. Get to know your clients. The kindness is likely to help you get the job, and the relationship is key to keeping them. Plus, life is just better lived this way.

  7. Invoice only (and have them pre-made). You'll notice missing from the customer service list above is "during the job". That's because you'll hopefully not talk to the client during the job. For gutter cleaning, there is no time to chat. Unless the customer already has the filled out check in their hand, don't ask for (or even accept) payment on the spot. Instead you'll leave the invoice where they specified, because you'll have.... (see below)

  8. Know everything you need to know before you pull in. After the quote, if you get the job, ask two things. First, ask where you should leave the invoice "if they're not home", and leave it there regardless of whether they are home or not (and needless to say, have the invoice/envelope pre-made and ready to go). Don't knock on the door. This is a race. There will be time to chat when you follow up after the season is over. And second, if you noticed woods during the quote, ask if you can empty the debris in the woods during the gutter cleaning. This means you won't have to empty it somewhere afterward, and asking ahead of time means you won't have to spend time asking during the job.

What am I missing? What has changed since I did this in high school? Tweet @kujoyardwear and let me know! I'll credit you and add to the list.