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The Baker Legacy: A Conversation on Employee Ownership and Business Success with Dylan Baker Transcript

In this debut episode of Under The Roof, hosts Todd Kavanaugh and Matthew Elban sit down with Dylan Baker, the fourth-generation leader of Baker Roofing Company, to discuss the company’s transition to employee ownership through an ESOP (Employee Stock Ownership Plan).

What You’ll Learn:

  • How the “Always Good Work” sign inspires the company’s core values and mission.
  • How the company’s transition to employee ownership reflects Rebecca Baker’s employee-first philosophy.
  • Why the multi-generational company gains leadership insights from Prentiss and Frank Baker.
  • How the ESOP structure benefits the employees and the company.
  • The importance of preserving the company’s legacy.

About the Guest:
Dylan Baker is the fourth-generation leader of Baker Roofing Company, a century-old family business founded by his great-grandfather W.P. Baker in 1915. As a key figure in the company’s leadership, Dylan has played a pivotal role in one of the organization’s most significant transitions – implementing an Employee Stock Ownership Plan (ESOP). Following in the footsteps of his father Frank and uncle Prentiss, who were instrumental in growing the company, and his mother Rebecca, who served as CFO, Dylan has continued the family legacy of prioritizing employee welfare and maintaining the company’s founding principle of “always good work.” In this episode, he shares personal insights about the company’s transition to employee ownership, discussing how this historic decision aligns with Baker Roofing’s values and its commitment to creating lasting value for its workforce of over 1,000 employees.

[00:00:01] Dylan Baker: The message and the mission, it’s all right there. And I can’t
spend words around that and do it any more justice than just actually looking at it and
thinking about what it means we’ll do. It’s been a wonderful constant for this business.
[00:00:18] Todd Kavanaugh: Hey there, and welcome to Under the Roof, the official
podcast of Baker Roofing Company. I’m Todd Kavanaugh.
[00:00:25] Matthew Elban: And I’m Matt Elban. We’re here to connect the dots
between field and office, leadership and crew, values and action.
[00:00:32] Todd Kavanaugh: In each episode, we dive into the stories, lessons, and
updates that matter to our team.
[00:00:39] Matthew Elban: From safety and career growth to company milestones
and good old-fashioned storytelling, it’s all about living out what makes Baker, Baker.
Let’s get into it.
[00:00:50] Todd Kavanaugh: Today, we have our very first episode of Under the Roof.
We’re joined by Dylan Baker, and this conversation is particularly meaningful because
we’re talking about one of the biggest decisions in our company’s 110-year history: the
transition to employee ownership through our ESOP. But this isn’t going to be about
technical details or financial structures. Instead, we want to hear from Dylan about
what this decision means for our Baker family, our heritage, and our future. Dylan,
welcome to Under the Roof.
[00:01:22] Dylan Baker: I appreciate you having me. Excited to be here.
[00:01:25] Matthew Elban: Dylan, let’s get things started and get warmed up. Simple
question, it’s a question I love to know the answer to when I’m talking to people: What’s
the last book you’ve read, and what did you like about it?
[00:01:34] Dylan Baker: I am rereading a book with the residential group called The
Rebel Allocator. It’s a book that I’d shared with some members of the leadership team
here as well. It does a good job of answering questions about how your value is
reflected in your pricing and in the marketplace. It tackles thorny issues of capital
allocation from the perspective of people who are not financiers. It’s an engaging and
simple read. It’s a good one.
[00:02:04] Matthew Elban: It’s funny you mention that one. I’ve actually read that, and
I really enjoyed it. It brought some simplicity to some conversations that can be really

difficult and challenging to have, but they break down into some really simple
takeaways. So, awesome book. Glad to hear that.
Next question: You’re a fourth-generation Baker Roofing leader. Your
great-grandfather, W.P., started this company in 1915. In fact, a few weeks ago, I was
able to swing by 19 Gale Street, which is where it all started. It looks way different
today than it did back then. I was able to get out of my truck, stand there for a few
minutes, and envision what your great-grandfather might have been thinking while he
was hanging up the sign in his shop. When you see that original sign, the “Always Good
Work” sign, on the wall in our new building, what goes through your mind?
[00:02:55] Dylan Baker: The obvious answer is pride. I really believe that sign has been
a force for good and a true North Star for this business. Todd, you might remember
fifteen years ago, the first time we got together at John’s church with Gary McGrath.
We thought the first thing we needed to do was come up with a mission statement.
There were 15 people giving input, and it turned into this long, unwieldy sentence that
tried to do too much and connect too many ideas about who we were.
It wasn’t until we got on the other side of that process where that sign resurfaced. The
message and the mission are all right there. I can’t spin words around that and do it any
more justice than just actually looking at it and thinking about what it means we’ll do.
It’s been a wonderful constant for this business. When you expand on that and all of
the fundamentals that we talk about, it dives into all of them. It really just answers the
question: “What’s the right thing to do here for the customer?” It does so in a simple
way that’s easy to process and leads to good results.
[00:04:09] Todd Kavanaugh: Yeah, that’s great. Recently, you told us a story of how
your mother, Rebecca, who was the CFO when I started here about twenty years ago,
would have approved of the ESOP decision. Can you tell us about her and what she
valued most about this company?
[00:04:30] Dylan Baker: I get better and more composed every time I relate my
mother to what’s happened here lately. I mentioned this in the town hall, but she was
100% about being in the foxhole with the people she worked with. You remember back
in the day, it was Fong and Cynthia, Mariana and Gisela, and just that whole crew.
She really felt bad that she could not do more to help. At that point, we were a growing
business; we were evolving and pivoting. Some years were really good; other years
were not so good. Sometimes you just couldn’t do much. She would not have been
able to imagine that this company would get to the point where something like this
would even be possible, where the business itself could be handed off as something

valuable to its employees, but with a roadmap attached that shows people how to
hypercharge the retirement benefits that come with an ESOP. There’s real value there.
The process of selling this… you go through pride, and maybe a little selfishness or
privilege that goes along with having your name out there. You wonder, “Is this the right
time? Will there ever be a right time?” You get a consultant involved, everything starts
moving quickly, and there’s momentum. Sometimes you find yourself on the outside
looking in, and everything needs to slow down. But then you think about Mom, and
Mom’s like, “This is for the greater good. There are a thousand-plus people whose lives
are going to be better for this. Just go. Get this done.” And now we’re on the other side.
[00:06:14] Todd Kavanaugh: I love that. I’ve heard it said that your mom was the heart.
Not to say that your dad and your uncle were not on that early board, but your mom
was the heart.
[00:06:27] Matthew Elban: Your dad, Frank, and your uncle, Prentiss, were super
instrumental in growing this company to what it is today. What lessons would you say
you learned from them about what it means to be the steward of something bigger
than yourself?
[00:06:42] Dylan Baker: I’ll start with Prentiss. You guys know Prentiss; he is a man of
endless energy. A lot of that energy has gone into Baker Roofing Company for a long
time. He is one of the most energetic and capable people I’ve ever known. To say you’re
going to learn lessons from Prentiss is like saying you’re going to learn religion from the
Pope.
When I think about Prentiss, I think about how this is a “people-first” business. He
teaches about trust and respect. You have to earn the trust and respect of the people
you employ and work with, and you have to be seen as someone that everyone can
trust and respect. He gets there in many ways. He is better than anyone at uncovering
a problem, getting into the details, and fixing it. But he always does that with an eye
toward personal connection, as a way of teaching, not as an “I got you.” That’s a
valuable lesson for any organization that you want to endure. He’s also the most
aggressive businessman I’ve ever seen.
Dad is a different person. He is very cerebral and ultra-competent. He is often the
smartest guy in the room and the expert on anything he chooses to be involved in.
Growing up with Frank Baker, there was some tough love. If you didn’t work at this
company in the ’90s and 2000s, you might be surprised, but he always encouraged me
to be a good steward of this business even when I did not have ownership. He was
always interested in what he called “the second one hundred years.” So, responsibility
and stewardship.

[00:08:50] Matthew Elban: It’s funny; each of us probably has many stories about
those guys. One of the funniest stories for me regarding your dad involves an issue on
a building in Richmond, Virginia, about ten years ago. Frank got involved, made the trip
up to Richmond, and got up on a stepladder to look at where the roof and the wall tied
together to figure out the exact problem we needed to solve. It blew my mind that he
would make that two-and-a-half-hour trip from Raleigh just to dig in on a stepladder.
That’s how I see both of them, willing to dig in.
[00:09:36] Dylan Baker: That is those two guys in a nutshell. They will do whatever it
takes to get the customer where they need to be. That means at age 70, both those
guys are going to go up a ladder and scale a 12/12 roof. They’re going to do it.
[00:09:53] Todd Kavanaugh: So, Dylan, you’ve got this unique perspective as the
fourth generation. As someone who loves the day-to-day work, when people ask if
you’ll miss owning the company, what do you tell them?
[00:10:09] Dylan Baker: That’s a good question with a complicated answer. I don’t
want to say ownership was a burden, but the second Mark, John, and I acquired
Prentiss’s interest, I started having dreams about signing a document in the wrong
place or forgetting to “carry the two” in a calculation and having the whole thing blow
up in our faces with a thousand people looking at me.
That didn’t happen, which is great. We got through the tenure. I never thought about
this as anything other than a caretaker job. There are people here who deserve
ownership in this business maybe more than I do. This is a fitting result for our
employees.
[00:11:09] Matthew Elban: Your family story is incredible: your great-grandfather’s tin
shop, your mom’s heart for people, your dad and uncle’s growth vision. This chapter
being uniquely yours, how do you want the “Dylan Baker chapter” to read?
[00:11:29] Dylan Baker: That the company did not die on my watch. I purchased
something of value along with Mark and John, put our little spin on it, and left it in
better shape. Something of value was passed on to the people who helped create that
value. Now, they have the upside and the day-one equity value of this company, which
will translate into a retirement benefit.
[00:11:58] Todd Kavanaugh: That’s great. You’re known for keeping things light, I
remember starting meetings with Sporcle. But thinking five years ahead, what do you
want people to say about the choice you guys made in 2025?
[00:12:27] Dylan Baker: I want the employees to realize the opportunity they’ve been
given. The timing is important. We did this this year for reasons we’ll talk about in the

coming months. We think that starting now, we’re going down a path of quick growth
in both top-line and profitability. We thought it was right for the employees to share in
that growth from the get-go, because we’re asking our employees to lead this charge.
By 2030, they are going to own the full increase in equity value from the plan we are
rolling out.
[00:13:17] Todd Kavanaugh: It’s like for an employee, myself, Matt, and yourself now,
too, to be able to look back and say, “Gosh, that was worth it.” Those five years of
stretching and working harder and smarter to reach those goals were really worth it.
[00:13:40] Dylan Baker: It’s my hope that by year five, the yearly statement people get
with their balance is meaningful to everyone.
[00:13:50] Matthew Elban: If your mom could see you right now, giving away
ownership to take care of the people the way she always wanted to, what do you think
the first thing she’d say to you is?
[00:14:00] Dylan Baker: She would be proud of me. She would be proud of Mark and
John. That gives me great comfort. She always said it wasn’t about Rebecca Baker; it
was about my sister, me, and Dad. She was not about herself; she was with the people
she worked with. She taught responsibility, selflessness, stewardship, and charity.
[00:14:29] Todd Kavanaugh: I was sharing this with my wife, and she mentioned this
might be a challenge to communicate. Most people today don’t expect a company to
truly look out for its employees. She even asked me, “Is this for real?” People might
think there are strings attached. How would you respond to employees who think this
sounds too good to be true?
[00:15:02] Dylan Baker: A company takes on the personality of its leadership. There
are humble servant leaders here, and that’s why this benefit now exists. There is
genuine care for the people listening to this and a genuine desire for their lives to be
better. We provide meaningful work that impacts their lives and allows them to help
customers with serious needs. The benefit here will be real and meaningful.
[00:15:44] Matthew Elban: Last couple questions. If W.P. Baker could see his
great-grandson today, would he be proud, confused, or wondering where you get your
sense of humor from?
[00:15:57] Dylan Baker: He was not one of the Baldwins, so I think that’s the first thing
he’d look at. I might be a little less drunk than him, I don’t know. But if you could conjure
me a hundred years from now and this thing was still going strong, I would be
absolutely elated. We think this is special enough to keep going the way we built it. This

industry cries out for a business like ours, so it’s worth protecting and ensuring it
endures into the next century.
[00:16:35] Todd Kavanaugh: One last question: What’s on heavy rotation for you right
now?
[00:16:42] Dylan Baker: Travis Scott just dropped a new album at midnight two nights
ago. I got to listen to that in my house; my son was upstairs in his room just blasting it.
[00:16:56] Todd Kavanaugh: Awesome. Well, Dylan, thank you so much for taking time
with us and speaking to our employees about this massive change. I think I can speak
for many when I say we are incredibly grateful for the decisions leadership has made.
It’s a really exciting future for our company. Thank you.
[00:17:24] Dylan Baker: Thank you, Todd. Thank you, Matt.
[00:17:27] Todd Kavanaugh: That wraps up this episode of Under the Roof. Thanks for
joining us and being part of the Baker Roofing family.
[00:17:35] Matthew Elban: If you liked what you heard, share it with your crew. Hit the
follow button and keep the conversation going wherever you work.
[00:17:41] Todd Kavanaugh: We’re here to keep you informed, inspired, and included,
because the more connected we are, the better we work together.
[00:17:49] Matthew Elban: And as always, we’ll leave you with this: We shall do good
work at a profit if we can, at a loss if we must, but always good work. See you next
time.