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How Family-Owned Culture Scales to 29 Locations with Darrell Bailey

In this episode of Under the Roof, hosts Todd Kavanaugh and Matthew Elban sit down with Darrell Bailey, General Manager of Baker Roofing’s Harrisonburg branch for 22 years, to explore what it takes to build a consistently high-performing team, lead with curiosity rather than fear, and create meaningful impact in your local community.

What You’ll Learn:

  • How to transform fear into opportunity through curiosity
  • The leadership currency framework
  • Why consistency beats innovation in local markets
  • The power of genuine community connection in business
  • How to delegate effectively without losing control
  • The importance of finding daily fascination in your work

Darrell Bailey is the General Manager of Baker Roofing Company’s Harrisonburg branch, a position he has held for almost 22 years since the branch’s inception in 2004. With vast expertise in roofing operations, team leadership, and community engagement, Darrel has built a reputation for consistency, quality, and genuine care for both his team and customers. His leadership approach, grounded in emotional intelligence, continuous learning, and ethical decision-making, has established the Harrisonburg branch as a model of stability and reliability within Baker Roofing’s national footprint.

00:00:01] Darrell Bailey: Curiosity converts fear into fascination. It creates this sense
of, “I have an opportunity to learn now”. We all talk about how “this isn’t a problem, this
is an opportunity”, and that’s true, but it gets cliché after a while. Just find something
that you really want to dive into and figure out.
[00:00:16] Todd Kavanaugh: Hey there, and welcome to Under the Roof, the official
podcast of Baker Roofing Company. I’m Todd Kavanaugh.
[00:00:23] Matthew Elban: And I’m Matt Elban. We’re here to connect the dots
between field and office, leadership and crew, values and action.
[00:00:30] Todd Kavanaugh: In each episode, we dive into the stories, lessons, and
updates that matter to our team.
[00:00:37] 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.
[00:00:48] Todd Kavanaugh: Hey, everybody. Welcome back to Under the Roof. I’m
Todd Kavanaugh.
[00:00:52] Matthew Elban: And I’m Matt Elban. Today, we are headed to the
Shenandoah Valley, specifically Harrisonburg, Virginia, to sit down with one of the
long-tenured general managers of the Baker team.
[00:01:02] Todd Kavanaugh: It’s Darrell Bailey. He has led our Harrisonburg branch for
quite a long time. What you need to know upfront is that Darrell is just one of those
people who makes a company feel like a community. His branch is always consistent,
his team is loyal, and Harrisonburg generally knows Baker Roofing because of Darrell
Bailey.
[00:01:36] Matthew Elban: We also saw some pictures of a batting cage, which I’m
excited to talk about, and possibly some history on the stage. There’s a lot to get into,
so we’re going to get after it.
[00:01:50] Todd Kavanaugh: Darrell, welcome to Under the Roof.
[00:01:52] Darrell Bailey: Thanks for having me. I appreciate it.

[00:01:53] Matthew Elban: Good to see you. So, Darrell, we’re going to kick it off like
we always do with the first question. What’s the latest thing that you have read or are
reading, and what’s your biggest takeaway from it?
[00:02:12] Darrell Bailey: I’m reading The British Are Coming by Rick Atkinson. We are
approaching the 250th anniversary of our country, and I thought it was appropriate to
go back and read it. It’s part of a three-book series that covers the Revolutionary War
from even before the beginning.
Every time I reread a book, I always pick something different out of it. I’m at a different
stage in life than I was five years ago. That’s what I like about history, it motivates me to
think about what people have done in the past, the privileges we have today because
of it, and what we’re going to leave for our posterity. It’s just a cool ride for me.
[00:03:10] Matthew Elban: I’m a big fan of Revolutionary War history. I love the quote:
“If we don’t learn from history, we’ll be condemned to repeat it”. I think that applies to
business as well as personal life. I write down every book recommendation, so I’m
looking forward to that one.
[00:03:33] Darrell Bailey: Once you read that one, you’ll want to read number two, and
you’ll be waiting with bated breath for number three.
[00:03:41] Matthew Elban: I will be waiting for number three.
[00:03:44] Todd Kavanaugh: Even though we know the ending already.
[00:03:49] Matthew Elban: Before we get into the serious stuff, give us the number:
How many years have you actually been running the Harrisonburg branch?
[00:04:02] Darrell Bailey: I’ve been with Baker Roofing since 2004, which was the
beginning of the Harrisonburg branch. So, this is my 22nd year at Baker Roofing.
[00:04:16] Todd Kavanaugh: Darrell, I hadn’t realized that we started in the same year.
2004 is my official start date, though I was a temp for a few months before that.
Another fun fact: if you want to see me and Darrell fist-bumping on Google Street
View, search for 517 Mercury Street.
[00:04:47] Darrell Bailey: I remember the day, Todd. I saw the Google car drive
through the parking lot and said, “Todd, we’ve gotta go out there so we’ll be on there!”.
[00:04:58] Todd Kavanaugh: We ran out there carrying something so it looked like we
were transacting business. We just fist-bumped so they would put us on there. When

Darrell says “follow me,” you follow him because he’s up for adventure. To that point,
I’ve heard you have experience on the stage. Is that true?
[00:05:40] Darrell Bailey: I really wanted to be in acting, but I realized I couldn’t make
a living at it. I’ve always enjoyed getting up and doing something either in a theater or
at outdoor venues. For about four or five years, I portrayed Patrick Henry for a historical
representation at Thanksgiving time over in Charlottesville. I had this cheap wig from
the five-and-dime downtown, and I was so proud to wear it. My kids would run around
in period costumes and have a great time.
But one of the funniest acting stories was back at James Madison University (JMU). I
auditioned for a part in Macbeth and got a dual role. One of them was the “whey-face
loon,” which is what Macbeth called me. I was supposed to announce that Birnam
Wood was moving to Dunsinane. It was a prophetic thing spelling the end for Macbeth.
I was standing in front of this imposing actor, and I froze right in front of the audience.
You should have seen the disdain pouring off Macbeth at me! That sobered me up;
maybe I needed to do something different.
[00:07:37] Matthew Elban: For those listening, hit rewind because Darrell mentioned
he still has a wig! I’d like to see that come out at the next general manager meeting in
November. I’ll talk to Barbara and make sure it happens.
[00:08:12] Matthew Elban: Tell us about your team. What makes the Harrisonburg
crew the Harrisonburg crew?
[00:08:18] Darrell Bailey: First of all, I love our team. We have so much talent and we’re
very communicative. For a long time, we officed in a common area with no privacy.
When we built the new building, I wanted that shared experience to remain. I didn’t
want compartmentalized work; I wanted a place to aggregate and tell stories. Some of
the best stuff in our office is “caught” rather than “taught”.
We’ve got great department heads. Jason Lawrence leads Department 40, our
reroofing department. He’s an operations manager with a great team: Stephanie
Schuler, Armando Mancias, and Edwin Hondres. Edwin and Armando are Construction
Managers (CMs) who have been with us for 15 and 20 years, respectively. The quality
they produce is phenomenal. Jason is a “force of nature” who doesn’t know the word
“can’t”. If it can be done ethically and responsibly, he can do it.
Department 90 is our service and repair department, led by Ralph Smith. David Nelson
is the service manager, and Barbara has been our coordinator for years. We’ve also

moved some experienced guys from Department 40 into service, which has been a big
boost technically.
Our sales team, led by people like Mike, who has been here 17 years, shows us how it’s
supposed to be done. I always say “you are what you eat,” and the type of work they
bring in makes a difference in our growth and customer experience. We want to be
trusted advisors for our customers. Our field guys put their fingers on more money
physically than anyone else, and they are responsible for profitability where the rubber
meets the road.
[00:13:35] Todd Kavanaugh: Darrell, you know your team so well. Harrisonburg has a
reputation for being consistent year after year. What is the secret to that consistency?
[00:14:38] Darrell Bailey: First, it’s the level of care demonstrated. People like to be
seen for who they are, and honest, respectful communication is the start of that.
Consistency is a cultural thing for us. We have a “give a care” attitude. We try to work
out problems in real-time.
Consistency is also about financial stability. The team knows that at Baker Roofing,
you’re going to have a job and the ability to grow. We’ve hit rocky times, the drought,
COVID, but we stay in front of customers and don’t take them for granted. As soon as
you lose your grip on the customer relationship, you lose the reason you’re in business.
[00:17:36] Todd Kavanaugh: What is your proudest moment regarding someone on
your team?
[00:17:37] Darrell Bailey: There are so many times when it rains and everyone is on
edge trying to get jobs watertight. My proudest moments are when I roll into the office
and see a crew that has been out all night doing a weather walk on a dry building. It
wasn’t required, but it was so important to them that the roof didn’t leak. They put in
that energy to make sure the customer is 100% satisfied. In our business, water
intrusion is the enemy. If we can take that worry off the customer’s shoulders, it’s a win.
[00:19:50] Todd Kavanaugh: I love that. Consistency isn’t one “silver bullet”; it’s doing
all the small habits, like a weather walk, to form a pattern of success. I also heard about
a community project you guys recently donated, a batting cage. Tell us about that.
[00:20:55] Darrell Bailey: It was an exposed-fastener corrugated metal panel system.
Three of our guys live in the Broadway area, which is a very athletics-oriented
community. One of our sales guys, Mike Oler, was approached about needing a roof for
a batting cage. They put the roof on over a weekend and donated their time. The guys

were just as proud as anyone to put their fingerprints on something that helps the kids.
Go Gobblers!
[00:22:19] Matthew Elban: Is giving back becoming “baked into” how you run your
branch?
[00:22:26] Darrell Bailey: Yes, it’s becoming part of what we do. We target community
involvement as an area of growth. We’ve also sponsored a “Trout Unlimited” event for
four years, where they take veterans with disabilities trout fishing on Beaver Creek.
Doug Miller, who started a chapter of Trout Unlimited, was as excited about that as he
would be about a roof sale!
[00:23:57] Todd Kavanaugh: What does it mean to you personally to be part of a
company that has that mindset?
[00:24:28] Darrell Bailey: It means a lot to know I have the freedom to invest myself
personally in the community because we’ve been financially responsible. When I’m not
in the office, this branch runs so well that I can go meet people. I really enjoy talking to
people, it’s how I’m wired. I feel like I’m growing professionally by developing a larger
social network.
I also love the technical side of roofing; I “geek out” about hydrocarbons and chemical
properties. I’ve been in the industry since 1992, and there is always something else to
learn. I even enjoy teaching the team about things like phenolic foam insulation!
[00:26:59] Matthew Elban: Baker has 29 locations now. In Harrisonburg, does it feel
like a national scale operation or just your branch and your town?
[00:30:01] Darrell Bailey: It’s both. Sometimes people call me “Darrell Baker,” and I
resemble that! It has a small family company feel because I can pick up the phone and
talk to second or third-generation Bakers who have a vested interest. We have the “big
company response” but the local branch feel.
The Shenandoah Valley is a blessed pocket of space. I’ve been here since 1982 and
never left. It feels like home. I raised four kids here, and I knew if they did something at
a lawn party that I wouldn’t be proud of, someone I knew would tell me about it later!
[00:31:32] Todd Kavanaugh: That unique DNA, the scale of the Eastern Seaboard plus
the local family feel, is what sets us apart. Now, on top of that, we are 100%
employee-owned.

[00:32:21] Darrell Bailey: I see the ESOP as a way to preserve something that works
and maintain continuity. Roofing is like “quicksand”, once you’re in, it’s hard to get out
because it’s recession-proof and you can make a good living. Baker Roofing is unique
and worth protecting.
[00:33:13] Todd Kavanaugh: Is there something you believed early in your career that
you’ve completely changed your mind on now?
[00:34:19] Darrell Bailey: Early on, it was all about worrying if my family was fed. Now,
after 40 years of marriage and four kids, I’ve learned that if you do the right thing,
everything tends to work out. My former boss, Bill, who I miss dearly, was a mentor who
taught me that doing the right thing takes the pressure off of having to be the
“resident expert”.
I’ve gone from worrying about every lost job to having confidence in staying the
course. As Mark Lee says, we don’t want to look in the rearview mirror all the time at
mistakes; we want to make good decisions today.
I also took leadership training ten years ago with Dr. Gary McGrath. I am proof that
process works. It taught me about emotional intelligence, not letting highs be too high
or lows be too low. I read that when Elon Musk became the richest man in the world, he
just said, “How interesting. Back to work”. I hope I’m becoming that person in my own
realm.
[00:38:28] Matthew Elban: What would you tell the next generation of employees?
[00:38:54] Darrell Bailey: Find something every day that fascinates you. Coal tar used
to fascinate me! Don’t just pass over things to move on to the next urgent task; stop
and focus on what’s important. I love Stephen Covey’s analogy about focusing on what
is “not urgent but important” before it becomes urgent. Become an expert in the little
stuff, like making a seam correctly or getting the primer right.
Find something you can control. I learned how to build a Salesforce report yesterday,
and I was proud of myself! If you can face challenges with curiosity rather than fear,
you win. Curiosity converts fear into fascination.
[00:42:56] Todd Kavanaugh: You said something earlier that I loved: leadership
training becomes like “currency” in your pocket that’s ready to spend.

[00:43:46] Darrell Bailey: You need to make ten “deposits” in a relationship for every
“withdrawal” you make. Everyone in this company leads in some way by their example.
Doing the right thing in your own realm has an impact on everyone around you.
[00:44:43] Todd Kavanaugh: Final question: What is on heavy rotation for you, music,
a podcast, or an audiobook?
[00:45:14] Darrell Bailey: I went through a Supertramp phase recently, specifically
“Child of Vision”. But this morning I woke up singing Marvin Gaye, “What’s Happening
Brother” from the What’s Going On album. It’s got such soul and passion.
[00:45:58] Todd Kavanaugh: Darrell Bailey waking up singing Marvin Gaye is a
fantastic image to leave us with! Thank you for giving us a look at what it means to
show up for your community and company for 20 years.
[00:46:28] Darrell Bailey: I appreciate the opportunity. It’s been fun.
[00:46:33] Matthew Elban: Harrisonburg is lucky to have you, and so is Baker. This is
what Baker looks like at its best: skilled, consistent, and genuinely invested in people.
[00:47:09] Matthew Elban: And as always, we will 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.
[00:47:41] Matthew Elban: See you next time.