Top 3 Money-Making Sales Lessons From My 1st Year in Roofing

Adam Bensman shares three roofing sales lessons from his first year: feel fear and act anyway, persist with service instead of pressure, and treat failures as relationship-building opportunities. He converted a nervous cold call into his first lead, won over a reluctant neighbor named Gerald through free inspections, and turned a lost deal with contractor Grant into a referral pipeline.
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These are the 3 money-making lessons that I learned early in my sales career that helped me sell millions. And I'm going to share them with you today. Each one of these lessons applies to you, whether you're brand new or you've been doing this for decades, because it'll help you make more money and serve even more people. My name is Adam Bensman, and I got in roofing sales in 2011 after taking the terrible advice of people that say, do what you're passionate about and you'll be happy and make money in life. And at that point in time, my passion was natural medicine. I went to this really great school and got certified in all of these modalities from massage therapy to polarity therapy to core synchronism to some of the hokey stuff like, like homeopathy and colon hydrotherapy. And by the way, drop a little comment if you know what colon hydrotherapy is. Yeah. So I'm doing all this stuff and I moved to Madison, Wisconsin. I'm like, I'm going to start a private practice. I got all the skills in the world. So I did, and it was easy minus the one thing, which was getting clients. So to make ends meet, I got a job as a massage therapist at a local franchise because when you don't have experience, it's hard to get one of the well-paying jobs. At that time in 2011, I was making just a little bit over $19,000 a year. I was living below the poverty line. My rent was really expensive because I was living alone and Easter came up. My family lived 2 hours away and I couldn't afford gas to get there. So my mom said, well, I see you at Easter. I said, no. She's like, why not? It's like, I can't afford gas. So she sent me $20 to fill up my truck so I could drive in for that weekend. And on the drive in, I called her to say thank you. My stepdad Ron ended up on the phone and saying, hey Adam, if you want to make a change, you need to make some money. You can, you can make $100,000 a year selling roofs door to door. By the way, Ron was in the industry. I didn't really know much about it because my parents were divorced and remarried when older in life. And I was like, who wants to get into door-to-door sales? I know nothing about door-to-door and roofing sounds boring. Well, I ended up taking the leap and that's what led me here. And what I'm about to share with you are those 3 lessons that made me a bunch of money. And I know they'll do the same for you. So let's get started. Lesson number 1. I was about 6 weeks into my first career in roofing sales. I knew nothing. I had the same narrative that you probably have. I don't know enough about the products. I don't know enough about the process. I need to, to know all this stuff to feel confident. I hadn't made a sale and I was doubting myself. Now it was the middle of the day. I was nervous. I had just gone to the gym to try to blow off some steam and get my head right. And as I was leaving, I saw a commercial building just adjacent to where I was working out with a for rent sign in it. I looked up at the roof. It was in terrible shape. Now at this point in Madison, Wisconsin, there was a recent hailstorm. By the way, these lessons apply even if you're doing retail. There was a recent hailstorm and I knew that this area had been impacted. I was, had never made a cold call in my life and I was literally sitting there in my gym clothes, in my truck, sweaty. I picked up the phone and it rang and my heart was just racing. I was nervous. I was scared. And this guy answered and he's like, it was, it was weird. You could tell it wasn't commercial. He was just like, hello? I was like, hey, uh, I'm calling about the property on Willy Street. Is it still available? And he goes, it is. I said, great. Listen, I'm actually not calling about the property. Calling about the roof. My name's Adam. I just left the gym next door and I drove by. I couldn't help but notice that your roof was in really rough shape, and I might be able to help you with that. And he goes, I'm glad you called. I'd love for you to come out tomorrow because I have a leak. I couldn't believe it. I'd never made a cold call before, and my inner confidence before was telling me I wasn't capable of it. In here, I just turned my very first cold call into a lead. I ended up signing up that roof. It was a lean-to style roof that was 90 square. And that led me to the first lesson. Fear equals go. Now, what do I mean by fear equals go? For many people, myself included, fear meant driving into a neighborhood and being crippled with fear and not wanting to get out of my truck. You feel the fear, so you pull back. But instead, what I did is when I felt the fear, when I was nervous, I leaned into it. And that gave me the confidence to know, listen, success is right on the other side of discomfort. And allowing me and encouraging me from that moment on to lean into fear, to push myself, to continually be uncomfortable, led to opportunities beyond my wildest dreams. And my greatest success to this day was doing things that scared me. That's why The one of the most valuable lessons, fear equals go. Now I wanna set, tell you about the second lesson. This was also early in my career. See, I had just opened up this brand new neighborhood. I was the only roofer in it. One of, I shouldn't say the only, one of the only roofers in it. And I, I signed up this one customer. Again, this was an insurance situation. So of course I started to knock the neighbors and there was an older gentleman I saw out mowing his lawn. And if I had to guess, he's probably in his early 80s and not moving around super well, but he was mowing his lawn. And I look up and he had this 3-tab roof that was in desperate need of replacement. Forget the hailstorm. He desperately needed a new roof. And I walked up, because I love catching people outside. I walked up to him to start the conversation and he kicked me off his property. And by the way, he was not very nice about it. I'm talking the kind that gives you the shoe, doesn't stop, doesn't really acknowledge you, like, get off my doorstep. So then about a week later, I'm there meeting with the adjuster, get the roof approved. I show back up again. Gerald, which, by the way, is his name, that'll come into effect later, kicked me off his property again. This time I caught him. I don't remember what he was doing, but I remember he was outside working on his property. It was in the summer. He kicked me off aggressively. Now, then I ended up with another neighbor and another neighbor. Gerald kept seeing me in the neighborhood, stopped by, shooed me off aggressively. We're on about the third or fourth visit, and I stopped by after we had replaced the roof of the neighbor who inspired me to reach out the first time. I said, listen, by the way, what I shared was maybe a little edgy, and I'm going to share it with you now. I said, I'm going to guess that you haven't been up on your roof. I am not here to force, push, or sell anything to you. I want to help you because I'm guessing you haven't been on the roof. I'm going to hop up there, take some photos and videos, and I want to just show you what your roof looks like so you can make a decision that you're comfortable with. And he finally said, okay, fine, reluctantly. I get up on the roof, I do my photo and video report, and I use the technique that I've shared before and I'll share again. Where's a good spot for us to sit down where you're comfortable out of the sun so we can go through everything? We sit down on his front step, didn't invite me inside quite yet. I start showing it to him and he goes, honey, he calls his wife over. She sits down next to me. They said, let's go inside. They invite me into the kitchen table. I show them the condition of their roof. They realize they desperately need one. I immediately have credibility from the neighborhood because I've done roofs and I'm working with other neighbors. They end up signing with me. I get their roof replaced. Gerald is his name. One of the few customers whose names I vividly remember, and I vividly remember him and his wife. We developed such a rich relationship. They invited me over for dinner. And the lesson that I learned from this is be relentless. Now, I know that some folks will say, oh, being relentless, you know, no means no. And listen, I get it. There's a, there's a time and a place of respect. But the distinction that I want to share with you is when I showed up, it wasn't because I wanted something from them. When you violate people's nos and boundaries because you want something from them, That's disgusting and gross. But I was persistent because I knew I could help them. I led with value and I developed a valuable relationship where they invited me over for dinner and later sent me home with gifts at the end of the project. This is why it is so important to lead with love and service, and that is how you can be relentless. Amazing things will happen. All right. This brings me to the third most valuable lesson that I learned early in my career. I had a telemarketing lead, and this was a lead that when I pulled up in the driveway, this might have happened to you before, pull up in the driveway, homeowners come out, they're like, no, no, no, no, no, we don't want you here. I'm like, well, what do you mean? We have an appointment for today. And I'm like checking the time. It's like, we have an appointment today. They're like, I don't know who called. I called them up. I tried to cancel. I got this weird phone, like it wasn't your office. And there was like no trust. They're like, I don't want anything to do with you. So I spent all of this time trying to validate that we were a real company, a local company, and I was there to help. Now, reluctantly, this couple, they, they let me on their roof. So I hop up there, I do my thing, I come down, and there was even more resistance, which was the second wave. And they're like, okay, we do want to get the roof done, but we want to wait until we do a screened-in porch off the backside of the house. Is that something you guys can help with? Now, being new in roofing sales, by the way, this is not the lesson, this part. I was like, no, let me see if I can find someone. So I go to my manager at the time. I'm like, do we have anyone that we can refer out for this back patio? We didn't do additions like this. He says, no, let's try to find somebody. So we find this guy. His name's Grant. And I call up Grant and I introduce myself. I say, hey Grant, my name's Adam. I'm a local roofer. And I've got this prospect who wants to do the roof, but they're waiting to do this screen-in porch addition. I was wondering if you might be able to bid it and that way I can do the roof and do it all together. So I meet Grant on the property. We spent probably hours with this couple going through different options. I sat in for this whole thing and kept following up and Grant kept following up and neither of us got the business. I was bummed. But fast forward, I get a call a couple months later and Grant says, hey, You know, I realize I don't have a good roofing relationship and I'm doing this remodel on this project. Can you handle the roof? Check. Of course I can. I get that roof. I get another call. Hey, I got another project coming up. Do you guys do EPDM? You bet. I got that roof. Hey, I just moved into a new home. Himself personally. Can you do my roof? Check. Got that roof. Then I get this call. Hey, I failed to mention I own 4 100-square buildings. That need a roof. And I got that job too. Over the course of the next few years, I was loaded with opportunities from Grant because of that relationship. And the lesson here is that success hides in failures. And what I thought was a failure by losing this job, because I led with value and did my best, it ended up creating a referral relationship further on. And what I realized through this is that there really isn't anything defined as a failure in sales if you don't learn from it, and that you have the capability to create opportunities out of nothing. And when you're in sales, sometimes your biggest breakthroughs don't come from strategies and tactics, but it's how to show up in sales. And it's training like this that we do together in the trenches almost every single week inside RSRA. Click the link in the description to learn more.










