Business Women’s Week Hippie Radio Interview with Penny Austermiller

As part of National Business Women’s Week, Hippie Radio recently hosted a fantastic interview with Penny Austermiller, CEO and owner of Austermiller Roofing, Inc., where she shared her inspiring journey as a leader in the roofing industry. Penny spoke candidly about her experiences building a successful business in a traditionally male-dominated field, shedding light on the resilience, innovation, and passion that have driven her company to the forefront. Her dedication to her team and commitment to clients truly stands out, making this interview a must-listen for anyone interested in the power of perseverance and leadership in business.

Interview Transcript

Radio Host: It is time y’all. I’ve been talking about this all morning. Of course, it is National Women’s Business Week. And women that own businesses in the Nashville and Middle Tennessee area, we are talking to them right here on this radio program. We are going to start today with Austermiller Roofing. And representing Austermiller is Penny Austermiller. She talked with Tony, and had a lot to say about ladies in business.

Tony: Hi, Penny.

Penny: Hello.

Tony: How are you?

Penny: I’m wonderful, how are you doing?

Tony: I’m good, thank you for coming in.

Penny: Thank you.

Tony: Alright so this is interesting. I did a little reading on you, and this is quite an interesting life you’ve led. Now, you started out—if I’m not mistaken—well, first, you worked at UPS for quite a while when you were in school.

Penny: Yep, for five years, I put myself through college.

Tony: Wow.

Penny: And the midnight shift at that.

Tony: Oh, really? The overnight?

Penny: Yeah.

Penny: And you slept when?

Penny: [Laughs] About three hours a day.

Tony: Yeah, exactly. And now you own your own businesses, so it’s about the same, right?

Penny: [Laughs] Yes, that’s right.

Tony: Anyway, you started at UPS, you worked there for quite a while. You got yourself through school, and you were a Poli-Sci major.

Penny: Yes.

Tony: So, how did you end up owning a roofing company? I mean, tell me [about] this journey.

Penny: Well, when I graduated, I worked for an acquisition merger firm. And I loved law. I was planning on going to law school, [but] ended up meeting my ex-husband. And he was a roofer, and had a sole proprietorship. And I had gone to work for WebMd, and worked for them—

Tony: That was another thing I read about you. You were on—WebMd was pretty new. That was a really cutting-edge different thing.

Penny: Yes, it was actually when it first started it was actually [Healtheon]. I went through all the mergers with them, and it ended up being called WebMd. And I worked for them for about five years as well. And I quit that job, and I came home and we incorporated Austermiller Roofing, and I’ve been running it ever since.

Tony: Wow, so you weren’t really a floater. You didn’t go from job to job. When you say you committed for a while, probably not knowing something else was going to happen? Is that it?

Penny: At each job I’ve learned something from it, and I just took it over where—I’ve literally had great mentors at the corporations that I’ve worked for. And they really just taught me to be a leader. And how to run businesses.

Tony: Well, obviously you’re a leader. It looks like you kind of—whether you wanted to or not—where it’s like “Oh, well, I guess I’m doing this now.” Right? “And I’m running the place.” Which happens, sometimes, and you can go with it.

So, would you consider yourself an entrepreneur? Or did you just, kind of, like, “Oh, this is interesting. Maybe I’m supposed to do that.”

Penny: Well, you know, at the time I really didn’t realize that. But I always—even when I’m in a room with people and we’re talking, I always think about what somebody needs or “What can I do to help somebody out?” And so my mind just works that way. So I have six different companies, and it’s because I found a need that somebody else needed, and that they’re willing to pay for the service.

Tony: Right, exactly.

Penny: So I would just start another company.

Tony: Now, and they’re not all going to be home runs. We’ve all tried that. I’ve done a little bit of that myself. But are these six businesses related?

Penny: They are. Four of them are all in construction, and two of them are in property management.

Well, it seems like everything I’m surrounded by is construction, so that’s why they’re all related to construction.

Tony: Was there anything prior to your ex-husband that was construction-based in your family at all?

Penny: Well my father was a framer. So, I grew up in construction.

Tony: So it was kind of a comfortable place for you?

Penny: Yes, and I’d swear I’d never be in construction. [Laughs]

Tony: Of course you did.

Penny: But here I am.

Tony: Yeah, exactly, how’d that work out? So how many folks do you have working for you?

Penny: At Austermiller, we have forty-two employees.

Tony: Ok, so, this is the thing. And we’re talking, again, with Penny Austermiller, the CEO and owner of Austermiller Roofing. It’s a responsibility, because you’ve got these guys, and they’re on roofs, and they’re dealing with hundred-degree weather, and they’re doing a really really hard job, and I just have so much respect for people like that. I mean, you gotta be grateful every day.

Penny: Yeah.

Tony: It is not easy.

Penny: No, and their mindset is amazing, you know. They have sweat pouring off of them, and they come in, and they’re still so happy, and just love their job. They love helping people.

And I know a lot of people don’t look at it like that, but literally when they go out and they’re putting on roofs for homes, it’s—these people live in them. That’s why we work so hard, is to have a nice home where we can raise our children, and protect everything we love.

Tony: Right.

Penny: So, these guys have such pride in doing that. And I love their energy. Every time I see them, the guys coming in to get their paycheck, they’re just full of energy.

Tony: Which is cool because it’s not just a roof, like you said. And let alone all the damage it could cause.

We are talking with Penny Austermiller, owner of Austermiller Roofing. As a part of our National Women in Business Week celebration. And we’re going to continue our discussion with Penny coming up in just a little bit right here on Hippie Radio 94.5

Radio Host: Hippie Radio 94.5 from a green-eyed girl, it’s Brown-Eyed Girl, by Van Morrison on Hippie Radio 94.5 on this Monday Morning. Hey, it is National Women in Business Week and we are taking some time out of our program this week and talking to some very special women, and today we’re talking with Penny Austermiller of Austermiller Roofing, and she has a lot to say about women in business in Middle Tennessee.

Tony: Is that how you sort of, if you’ve got forty plus employees, they are all different. And do you sort of know, ok, this is this type of customer, oh Fred is going to be really good with them, or Sara is going to be really good with them?

Penny: Absolutely, and for me, in my leadership team we all do the DISC Assessment and the Enneagram Test, so we all know how to talk to each other because we know how people are going—everybody is different.

Tony: Absolutely, and they’re all important.

Penny: Absolutely, so if you’re going to send me an email, most of my employees know they’re not gonna send me a novel because I’m not gonna read it.

Tony: Right, exactly.

Penny: They’re gonna send me bullet points, and they’re gonna tell me what they need, their problems, and I’m gonna help them fix it.

Tony: And the funny part is not only are your employees different but so are your clients. This person just wants to be texted, they don’t want the details. This person is going to want a twenty page explanation and spreadsheet. Ok, but if you know that up front, it’s fine.

Penny: Absolutely. And it’s the questions you ask the home owners, or the builders, you can figure out their personalities, and we do a lot of psychology training at the office.

Tony: That’s really smart to do that, yeah.

Penny: That way you know your customers, you know who you’re dealing with.

Tony: And it’s also an investment in your folks.

Penny: Absolutely.

Tony: And I’m sure they appreciate it as well, so anything you can do to—like what are some things that you feel you do a little differently that you offer your employees, that maybe some other companies aren’t thinking about?

Penny: Well—

Tony: Because it sounds like you’re in tune with your workforce.

Penny: Well we love our—we build our culture—we do our quarterly team building events, we really try to be a family. Everything we do, like as soon as I hire somebody, I tell them, “My name is on this company. My children walk around with this name. When they walk into a room, people are automatically going to know they’re related to the roofing company, because there’s just not that many Austermillers,” so I tell them—

Tony: Well, and Nashville is big, but it’s not that big.

Penny: No, it’s not.

Tony: People know each other and they talk.

Penny: Absolutely, so I tell them, everything we do, we do for our reputation, and we do for our family. So while they’re here, I always encourage the team: I don’t want you to resent me at the end of the day, I want you to be thankful for me because when there is your kid’s event or your family event—don’t miss it.

Tony: Right, exactly.

Penny: Go to that.

Tony: That’s first.

Penny: Absolutely, it should always be first.

Tony: And you know as long as you don’t take advantage.

Penny: That’s right.

Tony: And some do. And some don’t, though.

Penny: And they don’t work there anymore. [Laughs]

Tony: Yeah, exactly. And I understand that. So you’re in—the unique part about you being the owner, you are in the construction business, but I think I read a little bit somewhere where you’re like, “My gender doesn’t really matter.”

Penny: No.

Tony: “But it’s—can you handle it?” And I think that’s just kind of who you are. And it doesn’t really matter if you’re male or female. But growing up in it had to be a benefit to you to understand—because there’s some pretty strong-willed gentlemen out there in that business in particular.

Penny: Absolutely, you know, I grew up with three brothers, so I didn’t have any sisters, so I was always, it seems like, in a man’s world. I don’t really know any difference. So when people ask me all the time, “What were some of the challenges of working in a men’s industry?” To me, it was not about that. It was not about gender—it’s never been about that.

Tony: It’s about getting the job done.

Penny: It was more about me learning about myself. And overcoming my—making sure I have confidence, and knowing what I—you know, what I tell other people, roofing companies are not my competition, I am my biggest competition.

Tony: Right.

Penny: Because I know how hard I work. You know, it took me a long time not to be a boss, but to be a leader, and to help create leaders in my company. You know, for so many years we just had our heads down, working hard to grow the company and not paying attention to the culture and what was happening, and we got very stagnant.

And so we were determined to change that, and that’s one reason we do the DISC Assessment so we can learn the other personalities we work with every day. And so, I feel like because of that, and we care so much about each other, that we have built good discipline, good habits, and we just naturally grow together because of that.

Tony: Yeah, I had a boss who taught me: “If you want to excel and you want to move up that ladder, find your replacement.” It’s a sign of strength. When so many leaders push their people down to make themselves feel better. When really it’s the exact opposite. It’s not about how many names of companies you can get on your business card; the higher up you go, the more you should be serving—the exact opposite of what most people do.

Penny: Yeah.

Tony: You’re there to help your folks, your employees, and your customers do well.

Penny: Absolutely. You could put my management team in the room, and you won’t know which one of us is the leader because we all are like that. And I love that feeling, that atmosphere. When I go on vacation, I know the company is doing well.

Tony: Yeah. Not easy to do.

Penny: No, it’s not.

Tony: It takes a while to get there. You gotta have those right people, the right amount of scale, and all that stuff.

So, what kind of advice would you have for women, in particular, since it’s Women in Business Week, that maybe aren’t brave enough to get started but really know that they should? I mean, how do you get over that risk factor of, whether you’re dealing with banks, or anything like that?

Penny: Well, I think for women, we all have this—and even men—we all have this imposter syndrome thinking that we’re not enough. And having that doubt with ourselves. It just becomes you gotta believe in yourself. To me, if you conceive it, you dream it, you can achieve it. I just think women need to have that faith and believe in themselves, and don’t give up. You may be knocked down one hundred times; just get back up and keep moving.

Tony: And don’t compare yourself to other people.

Penny: Absolutely. And that’s in everything.

Tony: Yeah it’s unbelievable. Because it’s almost the self-talk that keeps you from doing what maybe you were really meant to do.

Penny: Absolutely, you know, the way we talk to ourselves, we believe that. So every day I get up out of the bed and say to myself, “I get to do this.” No matter what it is, I get to do it. So, I just change my mind set.

Tony: And it makes you appreciate life and work more.

Penny: Absolutely.

Tony: Well, it’s been a pleasure getting to know you. And thank you very much for participating and congratulations on your success. I didn’t even mention you got this big fancy award, a GAF President’s Award.

Penny: Yes, thank you.

Tony: So congratulations to you.

Penny: Thank you.

Tony: And that was in—your business was business of the year in 2023.

Penny: Yes.

Tony: Look at you! Well, keep it rockin’.

Penny: Well, thank you.

Tony: Thanks, Penny, for coming in. I appreciate it.

Penny: Thank you, Tony.