Kreg Bolander ran an operations department for a window manufacturer and had thought about owning a business for years, but finance, HR and taxes kept scaring him off. A company bankruptcy made him start looking seriously. He chose Brothers That Just Do Gutters because its systems and support covered the parts he didn’t know
Lisa sits down with Kreg, the new Brothers That Just Do Gutters owner for Elbert County and Northern Colorado Springs, to talk through how he went from 50/50 scared and excited to signed.
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What's covered
1:14 What finally pushed Kreg to look at ownership
3:22 Why operational support decided the brand
4:57 The moment it stopped being a dream
6:12 What the calls with existing owners taught him
What finally made him start looking?
Kreg always had ownership in the back of his mind. What held him back wasn’t the work, it was everything around it: finance, HR, recruiting, taxes. “I kind of scared myself out of business,” he says.
Then the company he worked for went through a bankruptcy he didn’t see coming. He kept his job, but it was enough to make him get serious. He already had the skills. He’d run an operations department, managed people and built processes. What he needed was a structure around those skills, so he wasn’t figuring out the rest alone.
Why did support matter more than the service?
Kreg is an operator, not a salesperson. He wants to be a very active owner, but he didn’t want a model that had him knocking on doors every day. He wanted to use his strengths: building teams, keeping people accountable, improving processes and training people.
That’s why the decision got clear once the conversations turned to operational, marketing and sales support. Every brand says it invests in its people. Kreg wanted to see it, and he did on confirmation day and in his conversations with current owners.
“Fear doesn’t have to be a stop sign. It can just be a yield.” (Lisa)
What did he learn from owners already doing it?
Kreg asked the questions most people skip. How do you keep good people during the slow season? Which trucks have held up best? What marketing works, and what doesn’t? Owners shared their failures along with their successes, and he asked to be connected with some of them personally afterward.
It took more time than he expected, on top of a full-time job. He says it was worth every call. He had never run a gutter business, and now he was starting with the lessons of the people who had.
Not sure whether this applies to you?
That’s the kind of thing a 15 minute call sorts out quickly. No cost, no pitch.
Who this is for
Operations leaders, managers and anyone who has thought about business ownership for years but keeps talking themselves out of it because of the finance, HR or sales side. If you’re looking for a completely hands-off investment, Kreg’s path will look different from yours. He plans to be in the business every day.
Questions people ask
Do I need industry experience to buy a home services franchise?
Not necessarily. Kreg ran commercial window operations and had never worked in gutters. What carried over was leadership, process and accountability. A strong franchise system teaches the trade side. Ask current owners how that training actually worked for them.
Can you use retirement savings to fund a franchise?
In many cases, yes. Kreg funded part of his business with money from his 401k. Whether that option fits you depends on your accounts and your situation, so talk it through with a funding specialist before you decide.
Been thinking about ownership for years?
That’s exactly the conversation we have all day. Fifteen minutes, no cost, and no obligation. Take the Franchise Readiness Assessment or
