Alan Melton: Most business owners think the trap is about working too hard. It’s not. The trap is about building a business that can’t run without you, and not realizing it until it is costing you everything: your time, your freedom, your family, and your future. I’m Alan Melton, founder of Small Business Coach Associates, and over the past 24 years, we’ve helped 1,100 business owners crawl out of the trap. This is Beyond the Owner’s Trap: real stories, real frameworks, and real freedom. Let’s get into it.
Alan Melton: My guest today runs a roofing company in a state where hurricanes create a gold rush every year, and where out-of-state crews show up after every storm chasing quick insurance money, then disappear. Jonathan Brosher is the owner of Better Roofing and Restoration, a family-owned residential and commercial company in Florida serving the Tampa Bay area with asphalt shingle, concrete tile, and metal roofing.
Alan Melton: Founded in 2024, Better Roofing has already earned a Better Business Bureau A+ rating, an Angie Super Service Award, and status as an Owens Corning Preferred Contractor, while explicitly positioning itself against the storm-chasing models that dominate Florida roofing after every hurricane season. John, welcome to Beyond the Owner’s Trap.
Jonathan Brosher: Happy to be here.
Alan Melton: Take me back to 2024, right before you started Better Roofing. What actually made you pull the trigger?
Jonathan Brosher: I was doing roofing sales for another company. I did sales for two companies before I started Better Roofing. I always knew I wanted to own a business. The moment I got into my first roofing company, I saw the structure and knew from day one I could do it on my own. The first company was very large and eventually sold to private equity. The next was a startup. It was me and the owner building the business together. I worked with him for two years, studied to get my license, put the vision and business plan together for Better Roofing, and we executed in August of 2024.
Alan Melton: Why roofing, and why make it a family business from day one?
Jonathan Brosher: Roofing is an excellent business. You can do a high-ticket item with a very good margin and complete a large project in a single day. You don’t need as much infrastructure as people think. You need to be able to talk to people and have a little capital.
Jonathan Brosher: Making it a family business is one of the biggest reasons a new company can build trust with homeowners. Bringing in family and marketing that we’re local allows us to build trust in our area. We already have a network here. Working with family is a blessing and a curse sometimes, but it is very fulfilling if you can do it right and work together.
Alan Melton: Who else in your family is part of this with you?
Jonathan Brosher: My brother. He was my first sales rep, and he’s my best sales rep. He came on right after we started. Then Hurricane Milton came through. He was boots on the ground with me a couple of weeks after we got licensed and incorporated. We were door knocking, running leads, doing inspections, and tarping roofs together. You can’t learn roofing faster than in a hurricane zone. He picked it up very fast. Right now he’s my best guy. He helps me within the business, and he’s a leader in the company.
Alan Melton: You’re two years in and still building the foundation. What surprised you about what it actually takes?
Jonathan Brosher: Pretty much everything. From a sales perspective, you see the glamour of what you think an owner does. It’s really a job I created for myself. Instead of working for somebody else, I work for my employees. I’m the end-all, be-all. When the phone rings and somebody has a problem, no matter the time of day, I have to be that person—especially at first, answering every call and taking care of every issue.
Jonathan Brosher: It’s gotten a lot better, but I didn’t fully realize I’d be a salesperson, production manager, marketing manager, receptionist, and the person who cleans the office. It’s not just the glamour of sales. I also get paid last. Those are the things I learned as an owner versus a sales rep.
Alan Melton: I like how you position yourself as serving your team and customers, when some owners want to be the boss. Where did you learn that perspective about servanthood?
Jonathan Brosher: I learned it from myself. I never worked well with a boss, but I did want to follow a leader. I wanted to be somebody people followed. I wanted to cast a vision my team could get on board with—something that fit their plans for their families, so they would help build it with me. I have the humility to understand I can’t do this myself. If I want to get where I want to go, I need a team behind me. It’s a lot more fun going together than going by yourself.
Jonathan Brosher: Nobody wants to work for a boss who is constantly on top of them and micromanaging. Everybody needs autonomy to grow. Setting that culture in the beginning is what’s allowed us to grow this early. Everybody takes ownership of their portion and understands there’s opportunity. Consistency as a leader has been my strong suit. They know I show up every day, and at the end of the day I have their best intention in mind before my own.
Jonathan Brosher: That gives me fulfillment. I think I would be burned out if I were doing it just for myself, barking words at people all day. When you take on a higher calling—the responsibility for your employees’ families, how they put food on the table—that gets you out of bed a little earlier and keeps you in the office a little later.
Alan Melton: Paint me a picture of the average work week right now. What are you still doing that you probably should not be doing?
Jonathan Brosher: I’m still ordering and scheduling crews. I had a production manager, and now I do not, so I’m in the process of rehiring that position. I’m also fully managing the sales team as their direct point of contact. I need a sales leader to bridge the gap and hold them accountable to KPIs. Those are the two shoes I need to fill. At our current size, I can handle the other administrative tasks. Once we get into the $6 to $7 million range, more hires will have to come on.
Alan Melton: What’s the hardest part of those first two years that people don’t see from the outside?
Jonathan Brosher: Coming from sales, you think that because you had some success as a salesperson, you can be a business owner. That is not the case. Ownership is more leadership than anything. Learning how to become a leader was the hardest part. Understanding marketing was very tough: which channels to use, what’s an appropriate ad spend. Some owners told me 2 to 3 percent of revenue. Others said 5 to 8 percent. Testing lead aggregators, Meta ads, whether to hire this company or not—I’ve realized I’ve had to fail everything at least once.
Jonathan Brosher: I’ve gotten over my fear of failure. Now it’s how fast I can get through the failure to get to success. How many marketing companies do I need to go through until I find the one that fits? How many lead aggregators? How quickly can I hire and fire until I find the right person? Finding the sales process that works for our team, implementing that SOP as fast as possible, and training so we start seeing results on close rate—those have taken a lot of time, but they’ve been the most beneficial to the business so far.
Alan Melton: John Maxwell wrote a book called Failing Forward. You really nailed it: failing, ideally failing quickly, and using testing as stepping stones. You mentioned you’re not putting in crazy hours right now, two years in. That’s unusual. Does that hold true after a hurricane season?
Jonathan Brosher: My definition of crazy hours has changed. When the hurricane hit, we were doing 12- to 14-hour days. We were on roofs at 6:30 in the morning until dark, with headlamps at night, tarping roofs, inspecting, and signing deals. That lasted four to six months. It was one of the largest hurricanes to hit the Tampa Bay area in 100 years. After that six-month period, I definitely hit burnout. It lasted about a week or two. I knew I needed people in place so I could work more on the business than in the business.
Jonathan Brosher: I had a production manager and a CSR taking the phones and ordering materials. That allowed me to stay home longer and work on marketing channels, go through the CRM, monitor sales reps, look at KPIs, and set up a dashboard: cost per lead, close rate, booking rate, who’s closing which deals, who is following up. That’s what I mean by working fewer hours. I enjoy that more than being in the field. I’m half in the office and half not, but my time now is more on the business than in the weeds.
Alan Melton: Your website draws a hard line against storm chasers—out-of-state companies that show up after hurricanes and then leave. Why was that important enough to put in writing?
Jonathan Brosher: When I was in sales, I worked Hurricane Ian around Fort Myers. I experienced multiple contractors take insurance checks from homeowners, then leave, leaving them with no money to replace the roof or do remediation. It was pretty rampant. We do insurance work, but we are not storm chasers. We’re storm catchers. We are planted in one area. We will not chase storms. We have our service areas, and we don’t leave them. We’re trying to build a real business in a community, not grab money, chase a storm, and come back.
Jonathan Brosher: A lot of out-of-state contractors—you have to be licensed in Florida. If you’re out of state, you really can’t do business down here. We wanted to clarify with homeowners: if you’re not working with a Florida company that has a Florida license number and an office in Florida, it probably doesn’t make sense to do business with that company.
Alan Melton: What does staying planted cost you?
Jonathan Brosher: I think it’s more beneficial. It would cost me more to storm chase. If you’re trying to build a business that lasts 5, 10, 15, 20 years, it starts by getting planted in the community. When you storm chase, you’re exchanging long-term success for a short-term gain. It’s a money grab. I believe it’s unethical, because I don’t believe that company will be in business two or three years later to service the customer if there’s a warranty issue.
Jonathan Brosher: Getting planted is where you see the fruit: referral pipelines, the fruit of good work flourishing over time. Time in your service area is one of the best marketing channels. If you have a great customer experience and customers talk about it, you’re going to have a very successful business. That’s what we’re trying to do.
Alan Melton: How do you position the company with prospects who might be scared of hiring somebody after hearing about fraudsters who take the money and run?
Jonathan Brosher: That was difficult at first. When the hurricane hit, we were a fresh company. We had no reviews, no accreditations, nothing to show we’d done business. Some people could have thought we were like those companies. Luckily we had some referrals, but it comes down to how well you can get people to trust you and explain the process.
Jonathan Brosher: I had a portfolio of work I’d done in the Tampa Bay area as a sales rep. I had to show people my individual license, that I’m incorporated in Florida, my insurance policy. I had to get on the phone with my Owens Corning rep sometimes and ask them to talk to a customer about work I’d done in the past. I had to get references from past customers. I had to sell myself: we’re a startup, but I don’t have the backlog the big companies have. They’re going to sign you up and not put your roof on for six months. The moment you get paid by your insurance company, I’m going to have your roof on in a week. That was one of our biggest value-adds as a small company. I’m with you A to Z. There’s no middleman. I’m the owner. My name’s on the permit. You’re dealing with me.
Alan Melton: BBB A+ two years in, Angie’s Super Service Award, Owens Corning Preferred—those didn’t happen by accident this early. What did you actually have to build to earn those?
Jonathan Brosher: Owens Corning required volume. We had to do a lot of roofs. With Angie’s, we really service those customers. We’ve had a lot of success with Angie’s leads. I know they get a bad rap in the industry. For us, we did well and still do. When we get a job from Angie’s, we go back to that original aggregator and ask for a review. That’s probably how we got our accreditation with Angie’s.
Jonathan Brosher: BBB came from getting as many thoughtful reviews as possible, asking every customer, and asking them to put one on Google and also on the BBB. Not just one platform—as many platforms as possible. Google doesn’t want 100 Google reviews, one BBB review, and no Facebook profile. They want to see a presence all around. You’re not going to get a great review without a five-star experience: communication through production, shaking their hand when you pick up the final check, genuinely saying thank you, asking for a review, and asking for friends and family down the road.
Alan Melton: If Better Roofing doubles in size in the next two years, what breaks first, and what are you doing about it now?
Jonathan Brosher: Labor shortage. That’s what we’re seeing a lot of in Florida. We’re looking at getting up to five crews on staff or at least on standby, and as many crews as possible. We have a revenue number: every time we hit that amount, we want another crew already available. If we doubled now, we’d probably need six to seven crews between full replacement and repair labor. That would be the biggest bottleneck.
Alan Melton: How about crew leads? Is that a challenge?
Jonathan Brosher: As of now, no. Our sales reps actually manage our projects right now, with fill-in crew leads. The sales reps like to manage their projects because if they’re not running a lead, they’re on the job talking with neighbors. If they do have a lead, another crew lead can fill in. It gives the customer a full experience with the person who sold them the job, through picking up the final check. It helps keep expectations aligned.
Jonathan Brosher: We will get to a point where lead volume is so high that sales reps have to be out selling and we need a full-time crew lead on job sites. Right now I really like the model at this volume, so I’m not too sure yet.
Alan Melton: Zoom out five years. What does the business look like when it doesn’t need you in it, and what does that make possible for your family?
Jonathan Brosher: I think it looks like me not having to be involved, which I don’t know if I’d like or not, to be honest. I do see multiple locations. I see some of my core leaders potentially being partners, or heavily invested and benefiting from the business. It could set up my core leaders and my family, whether that’s an exit or a great business that feeds our family. All around, a business with a phenomenal reputation in the community that gives back.
Jonathan Brosher: I’ve always wanted to give a percentage of profit back. We’ve done free roofs for customers. I want to get to a place where for every million, we can do a free roof. If we’re a $10 million company, that would be 10 free roofs a year. I would love to do a free roof every single month. It would be powerful to tell a customer: when you do business with Better Roofing and Restoration, a percentage of your job goes back to helping give a roof to somebody in need. That would be my dream—a community-driven company that feeds the core leadership. That’s the goal.
Alan Melton: At this point we do a stage check using the Seven Stages to Business Freedom. Stage 1 is startup, the dream. Stage 2 is chaos: you’re doing everything. Stage 3 is break-even: grinding but stuck. Stage 4 is burnout: you’ve hit the wall. Stage 5 is profitability: systems are working. Stage 6 is success: leaders are leading, you’re making a positive impact on the community, and likely winning awards. Stage 7 is freedom: acquire another business, replicate, or exit on your terms.
Alan Melton: I’m amazed at how rapidly you’ve built the business and gone through those stages. You learned leadership after you started, got up to speed, learned KPIs. Where you are now is working very well. BBB A+, Angie Super Service Award, Owens Corning Preferred, values first. Most businesses would still be in Stage 1 or 2. You went through burnout, but it was short and you recovered. I would say you’re solidly in Stage 5, which takes most businesses multiple years. I’ve coached businesses around 10 years-plus that would not be in Stage 5. You even have some features of Stage 6. How does Stage 5 feel to you?
Jonathan Brosher: That’s a very fair evaluation, 100 percent. For anyone watching who’s considering starting their own business, or who’s in sales with another company, this is why I would attribute our rapid growth: for the five years I was in sales, I treated it like I was running my own business, because I knew I wanted to. I watched the organizational structure from within. I served my company. I was still a phenomenal salesperson. I added value. But I asked a lot of questions: suppliers, manufacturers, how to get subs, how to acquire customers, lead sources. I got very connected in the industry.
Jonathan Brosher: When it was time to start, I felt more equipped than anybody just starting up, because I didn’t do it too soon. I sold for five years. I learned every aspect of the business by working with a startup and a large corporate company. I saw the pros and cons of both. I could see how you get trapped in that $1, $2, $3 million range, and what it looks like to get into a $10 or $15 million company. I learned those lessons before I started. That’s how we’ve grown so quickly. Stage 5 is about right.
Alan Melton: You knew five years before starting what you wanted. You applied yourself, learned from the experts around you, and pretty much knew what you were going to do once you started.
Jonathan Brosher: I actually did write it down. In the first year, the goal was $1 million in revenue. We started in August. My license registered with Better Roofing around August 31. From basically November 1 to January 1, we did $680,000 in revenue in two months. We well past our full-year revenue goal. Obviously a hurricane came into play—a lot of low-hanging fruit. Now we’re about to match if not beat what we did last year, almost as an 80 percent retail company. We pivoted from insurance to retail. Roofing is down 30 percent statewide. For a new company to match hurricane-zone revenue in a hurricane hangover, I call that a win.
Jonathan Brosher: Writing it down was one of the most important things I’ve done. I looked at it every day. I had a very clear vision and goal of how I thought I was going to achieve it. It changed as we got into the weeds, but I had a lot of clarity. Clarity gives power to take action.
Alan Melton: If you’re watching this and you heard yourself in Jonathan’s story—doing it the harder way, building trust in a market that rewards shortcuts, still carrying too much of it yourself—that’s not a coincidence. The Owner’s Trap finds everyone who builds something real. The way out is one honest decision at a time. If you’re ready, go to smallbusinesscoach.org. It takes about 60 seconds to book a strategy session.
Alan Melton: Jonathan, this has been a grounded conversation about a harder path than most of your competitors are taking. Two years in, you’ve already built a reputation most companies take a decade to earn—not by chasing the storm, but by staying planted after it passes. You started with a decision to do this the right way, even when the market made it easy to do otherwise. That’s the whole story. Where can people find Better Roofing and Restoration?
Jonathan Brosher: Our office is right off U.S. 19 in New Port Richey, Florida. We service all of Tampa Bay, all the way down to Sarasota County, up to Hernando County, and over toward Orlando. betterroofing.com is very straightforward. You can find us, and we’ll be happy to help you.
Alan Melton: How about your phone number?
Jonathan Brosher: 813-455-1954, or email us at office@betterroofing.com.
Alan Melton: Everybody, go support Better Roofing and Restoration. All the links will be in the show notes. Before we close, I want to speak to anyone watching who runs a trades business—roofing, construction, any service where trust is the product. Jonathan’s story is your story: the temptation to take the fast money, the harder, slower path of building something people actually trust, and the quiet question of what it costs you personally to do it that way. You don’t have to have it all figured out to take the next step. You just have to be honest, as Jonathan was today, about where you actually are.
Alan Melton: If this episode resonated with you: one, share it with a trades owner who’s doing it the harder, right way and wonders if it’s worth it. Jonathan’s answer is yes. Two, if you’re ready to find your own way out of the Owner’s Trap, go to smallbusinesscoach.org and book a free strategy session. Three, subscribe wherever you listen and leave a review. It helps more business owners find this show. I’m Alan Melton. This is Beyond the Owner’s Trap. We’ll see you next time.
