painting business, painting contractor, painting, business coach, painting

How To Market To ‘Tweason’ Residential

How are you filling your ‘Tweasons’? What’s a Tweason? I will tell you in a second.
I am Ron Ramsden, I am a DYB coach, also a painting contractor. I am located here in Massachusetts, behind me about a half mile or a mile away is New Hampshire. I am right on the coast here, on the ocean. I just got back from a run, that’s why I have the neon shirt.

Anyways, I was thinking as I was out there talking to a couple of painting contractors in the last couple of days. One of them was actually running out of work, his season was coming to an end, and he hadn’t planned for the interior season as the weather cools down. But then again, if you are watching this at another time of the year, the weather might be warming up, who knows?

It’s the in-between of the seasons. For me, I am going to call it a ‘Tweason’, and up here in New England, we have a very busy summer, our fall is very busy, then we have a little space during the winter and then it gets to winter season, and then of course, the spring and then we take off again.

But there are those times between the seasons that sometimes are quiet if you are not doing your planning, if you are not doing your marketing, and touching base with the customers, you might have some downtime.

I am on one of the access points to the beach, that’s not my house, by the way, I pass it every day. But behind me, I have been doing some Googling to find out what rents are during the summer, and on the water, you can’t touch them, they are $3,500 a week.

If you want one street back, you are getting it for about $1,500 for a two-bedroom, a place just for the week, and of course, there are no guarantees that the weather is going to be nice.

But if these homes here, being built, most of the houses they buy them, tear them down and they build homes like this. If we walk down the beach, you are going to see hundreds of this. Actually, we worked on a house down the street, near Texas alone, worth $32,000 a year. So that would go to show you the size of these homes.

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But anyways, some of these are for rent, by the week, $3,500, $4,200 a week, amazing, and you know if someone has this kind of house, they are not doing the work themselves, everything is hired out.
Obviously, bigger homes don’t do their own work. And as their summer rentals leave, some of them might have winter rentals, and other ones do some renovations. Some of them are financially set, so they don’t touch it, or have anybody in these during the rental, but they do have work being done.

And if you walk down the street, or go for a run down this street, you are going to see all kinds of renovations, and this is happening in your area also.

So, what you want to do is to market it, and I am not saying a costly marketing plan, to the owners of these, maybe Facebook sponsored ads, maybe touching base with the realtors in town who are renting out these, and let them know you are insured, you have quality work. Or maybe stop into the office with coffees and donuts. Maybe ask them if you can get a half hour of their time, bring them a gift, a thank you gift for taking time with you.

Let them know your portfolio, maybe email them a video, and as you see, I am a big proponent of video marketing, of sending them videos, people love to watch videos. So send them something that is eye-catching, maybe walk by one of their signs, stand in front of their signs and tell them how you could help them with your fast turnaround. Maybe it is a financing plan you have, maybe they accept credit cards.

You can do it when no one else would do it and have that space that you can give them a little break to get your foot in the door. We don’t want to do anything for free, maybe free upgrades of all the paints of the house, maybe work with your paint dealer at the same time.

Anyway, I just wanted to say, you’ve got to think outside the box, you don’t want to do anything that you are not comfortable doing. If you are not a handyman, you don’t want to promise them that you are going to do some handyman things.

Look at your 3 P’s that we talked about; your Process, Profit and your People, if you are really great at it, fine woodwork, re-staining or kitchen cabinet painting, maybe that’s what you want to bring to these new clients and I can tell you possibly have.

I am going to call them the ‘Tweason’, this is the in-between the seasons. Look for those key areas, you might have the summer rentals with the lakes, have the winter rentals with the skating, and then you have the middle time, that is in-between the seasons, we are going to call that marketing to the Tweasons.

I hope this helped you, maybe you are thinking of something new, you got to think of where you are not touching base right now, where you want to touch base, do you want to live at the beach? Maybe you always wanted to live on the beach, and you want to start a market and expand over to the beach where you can move your company.

I am just thinking on the run here, I hope this helped you? I thought about a hundred different things as I went for a run and this was one of them. So anyway, enjoy your seasons, it is beautiful out here.

Again, am Ron Ramsden, and I am a DYB coach, and I’d love to chat with you. Send me a message at ron@dybcoach.com, find me on Facebook, I would love to chat.
Fill up your ‘Tweasons’, I will talk to you soon, bye…

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About the Author

As many of you know, my journey has been one of grit, grace, and transformation. At 19, I was a high school dropout, single father, and struggling paint contractor in Michigan. I later moved to Florida, where I faced both personal and professional hardships. With nothing left to lose, I turned to prayer—and was blessed with a relentless hunger to learn. I devoured books, attended seminars, and discovered better ways to streamline and grow my business—even through the Great Recession (and yes, I did hit the wife lottery along the way!). In 2014, I published How To Double Your Business and later sold the painting business, launching a new chapter: coaching others to grow their businesses. For the past 10 years, I’ve dedicated myself to helping business owners scale through the DYB System, while also drawing from frameworks like EOS, Scaling Up, and The Four Disciplines of Execution. Yet something was still missing—something more adaptive, integrated, and complete. Then I found Pinnacle. After months of research and interviews with other Guides, I joined Pinnacle. Their tools and strategies have exceeded every expectation. Now, as a Pinnacle Business Guide, I help leadership teams implement a custom-tailored operating system that draws from the best in the industry—but flexes with your unique business. It’s a dynamic, proven approach to achieve clarity, momentum, and lasting growth. I’m no longer taking on any more 1:1 coaching clients… Instead, I now specialize in working with visionary business owners who are ready to get their leadership teams aligned—around a clear vision, a focused strategy, and an actionable execution plan. With the tools and process I now have as a Pinnacle Business Guide, I help turn alignment into momentum, and momentum into results. If your business is growing—but your leadership team isn’t fully rowing in the same direction—let’s talk.