Lessons in Leadership: Dave Holland’s Journey to Success

Hey, everybody. Welcome to Lending Leadership. It's me, Rach, and I'm here with Dave Holland today. And we get a special sneak peek in in chatting just with Dave and talking about how he got to where he is today and, you know, asking some pretty unique questions. Dave, I have some pretty fun things teed up for us, and I'm excited to just have some one on one time with you.

I'm excited too. Let's go.

Alright. So, you know, we oftentimes we have the 3 of you on, Robert, Tom, and you, and and I love the dynamic between the 3 of you. But I'm excited to just learn more about you and how you got to the position that you're in today. I know nothing's easy. Sometimes people like to look at our success and where we are and think, oh, wow. I could never do that. But we know there's a lot of work that goes behind that and goes goes into that.

It's not a straight line.

It's certainly not a straight line. It never is. It never is. So alright. Dave, let's start with this.

Throw me a softball, please.

Okay. I'll throw you a softball.

Warmed up, Rachel.

Okay. I would actually love to know what was your very first job, and, you know, what was something that maybe it taught you about leadership, if anything?

Yeah. So my first job in high school, I was the yeah. Well, I mean, you know, landscaping, you know, going door to door, those type of things. My first real job in high school was I was the field general and head ref for a a youth soccer league. So had to set up the nets, handled all the refs. I had some adult help, so definitely a quick lesson at a young age. I couldn't even drive. My mom had to drive me up there to set up the nets, the 1st summer.

So definitely a crash course in a little bit of leadership, handling a lot of people, dealing with irate parents. So, it it was interesting for sure.

Hold on. Irate parents in soccer? That would never happen.

I think it was from 6 to 16. Right? So it was it was a mix. Yeah. And I also ref the entire time as well too. So, yeah, it was definitely a good mix of, leadership responsibility. If I'm being honest, I probably wasn't ready for it, but, you kinda fake it.

But who's ever ready for anything? Right? I think sometimes if we were to stop and think about anything, it's like, oh, I'm not ready for that. But trial by fire, my friend.

Absolutely.

If there's anything that gets you ready for life, it's coaching or reffing kids' soccer because, oh my gosh, people can be pretty tough.

Absolutely. Yeah. I I had to call the police a couple times. I had one of those old brick cell phones. I had to cancel some games. I was only 15. I can't believe I even got the job looking back on it. So I did have some adult help here and there, you know, but it was mostly me, all afternoon.

Wow. Calling the cops on parents. That's interesting.

Yeah. That

yeah. With the old Zack Morris brick phone. Yep. Mhmm. I remember those days.

Mhmm. I

kinda miss those. Before. Yeah. I kinda miss those. Okay. If we were to look at your high school yearbook, what would it say about who you were then, and would that person have guessed where you are today?

Whoo. What? By the end of high school, I had, like, long hair to hear when I probably had the picture taken this summer. I mean, I always had a back in a ponytail. When I had the picture taken this summer before I was wearing a suit, it was long ish, but not that long. Would the person then look at me today? I don't know. Wow. I mean, he'd he'd probably be a little confused. Right? I mean, I I think you can say that about a lot of people, you know, you know, 30 years ago.

So, yeah, a little confused.

What did you wanna be when you grow up?

A lawyer. I thought my my dad my dad's an attorney, so I just assumed I'd go to law school and be an attorney. And then I started studying for the l stats in college and realized pretty quickly I would make a mediocre attorney at best. And, you know, I would probably always be my dad's son, in law.

Yeah. That how was that discussion? Was that a hard discussion to have to say, hey, dad. You know, this just is not my path.

Oh, he he wasn't pushing me. So there was no there was no pressure on it. I was kinda pushing myself. My dad's a real estate attorney or, you know, a a soon to be retired real estate attorney. You know, attorneys retire very slowly. So he was he's a soon to be retired real search. He didn't care at the end of the day or may maybe he did, but he never let on. And then I did title searching, for his law firm and for him, the back half of college.

So some good real, you know, real life mortgage experience at least in the title end. So gave me a deeper understanding of the mortgage business to a certain degree and and title. So, that was that was great experience.

You know, I love to hear that because sometimes, again, like you started off saying, nothing is linear. Nothing is, oh, we went here, and then I got this job and move along the line. No. It's like, well, it's messy, and you figure it out. But how cool that you probably wouldn't have had that experience of, you know, in the title role if you had not said no to wanting to be a lawyer.

Abs yeah. I mean, I think that was kinda like my precursor to being a lawyer.

Oh, gotcha. Okay.

So they'd hang them all up for me. I I had a bunch of ill fitting suits for my uncle, and I wore a suit because I looks like such a baby at 22. So I wore a suit every day at work, and lived in my grandparents' basement for the 1st year of my career. So you talk about being hungry and working hard. I didn't have any clients. I didn't have any realtor partners. All I did was make calls, study, learn. So, it made me really hungry to get out of my grandparents' basement.

Really worried. Loved having you there. I'm sure they loved having

you there. Yeah. It's the house my my mom my mom and her siblings grew up on, and, my grandma still lives there. So it was definitely a, you know, cool experience. Even though it wasn't cool then, looking back, it was a really cool experience. And I there's no way I would work that hard if I had a 9 to 5 job, like, if I was an engineer, you know, making 30 or $40 a year or an attorney. So it made me work a lot harder for sure.

Yeah. I'm sure you, got ragged on from your friends. Like, oh, here comes Holland. Is is grandma grandpa coming with you? They get a

You you think?

Help you out?

You think?

I mean, maybe not. I'm sure I'm sure grandma would cook for friends and, you know, that she was probably lovely.

Yeah. Yeah. It it was cool. It it was all good. I'm I'm glad it happened looking back on it.

Alright. So so switching gears just a little bit. You know, you have become a strong leader in the mortgage industry, but I wanna know I wanna know, was there a moment that you realized, and what was the moment? Okay. This is my lane. This is where I wanna be. You know, what kind of sparked that realization? Because we know in our twenties I don't think anyone tells you how hard your twenties are, first of all. You know, you just kinda go along the path and, like, alright. I like this, and, you know, you're living in grandparents' basement.

Like, okay. This is good. This is good. I like wearing a suit. I like I like where this is going, but was there a pivotal moment to tell you, like, I'm really good at this. I like, this is gonna be my forever position.

Yeah. I mean, I I knew pretty quickly, you know, my first boss, you know, told me I had to sign a noncompete, and I said, I'm not doing that. And he said, why not? I said, because I'm gonna start my own company within the next 5 years. I mean, that was, you know, just me thinking that. But but then I started to gain a little success, get a little momentum, and I knew it was something I'd be good at. I was good with the numbers. I was good with customers even at a young age. I felt comfortable, you know, didn't make me nervous, you know, meeting someone who was buying, you know, back then, like, a $300,000 house.

I I felt comfortable. I I kept I felt comfortable networking with realtors. I used to go door to door to realtors office passing out rate sheets when realtors were still in the office or bringing donuts. And, you know, not that I was lighting the world on fire, but for me, you know, the next year, I made a little bit of money. I wasn't on the $1,000 a month draw, and I wasn't living in my grandparents' basement. So I felt, you know, for successful for what I was doing.

What did that boss say? I'm so curious, you know, when when you said, I'm gonna go start my own company. Was he like, yeah. Sure, kid. Or was he supportive?

I mean, he thought I was probably full of it, but I think he kinda liked the the gumption of it. You know, he he he kinda liked that I was forward thinking.

Yeah. He's probably like, who is this kid? Okay. Let's see what you do. Do you do you still keep in touch with that guy?

That's that's a whole different story for a different podcast. But, no, I don't. Yeah. I don't. No. That's a different that's a different story. Yeah. I left on good I left on good terms.

I left on the best terms possible. Good.

Well, of course, you would. Because you're a class act.

Yeah. Well, thank you.

Alright. So my next question, maybe it seems, I don't know, trivial or maybe people ask this in a lot of interviews, but but I think it's a great question. You know, early on in in your career, was there a piece of advice that you got that was just has really stuck with you and has been just really valuable advice that that shaped who you would become.

Yeah. You know, my uncle is also a real estate attorney, and this is before the crash. So there's a lot of unsavory characters in the mortgage business. And he said, David, you can do this for the next couple years, 2, 3 years, and make a lot of money, or you can do this the rest of your life and, you know, treat people the right way. And I really took that to heart, because the mortgage business 20 plus years ago was significantly different, not as regulated. Dare to say it was kinda wild west. But, you know, one of one piece of advice I give to young people in any profession is put yourself in uncomfortable situations, you know, as much as possible where you're kinda at your league a little over your head, and you just get used to it. You know, just put yourself in uncomfortable situations.

You know, my my younger cousins my one you know, her cousin asked me that. I that's what I told him. I think that's good advice. Because if you're out of your comfort zone, you're probably in operating in the right spot then if you wanna

grow. I think that's great advice. I mean

Cliche. I'm I'm sure I'm not the first person who said that, but it's true. It's true.

Well, you just took the words out of my mouth. I was gonna say maybe it's cliche to say, you know, and a diamond doesn't become a diamond without pressure. It's cold to have extreme, extreme pressure, but it's so true. And I I love that visual. You know, we do have to put ourselves in in comfortable positions that you're you're forced to learn something new. You're forced to to step out of that comfort zone.

Feel the fear and do it anyways.

Yeah.

That that's not for me. That that's from Carl White. But, you know, feel the fear and just do it anyways. You know? Put yourself in uncomfortable situations. That's kinda where the growth happens.

That's something that's big in our family. I tell my kids that all the time. You know? Like, oh, I'm scared. I don't wanna do that. I'm like, that's okay. Do it afraid. No one's gonna know. Just do it afraid.

You're

feeling it. Put yourself out there. Put yourself out there.

Yeah. It's good advice. Leaders, I think, are often shaped by failure as much as success.

Mhmm. You know,

it goes both ways. We learn from the things we do terrible and don't work out, and then we learn from our successes too. Can you share

There's a 100 there's a 100 cliches for that. Right?

But I know. I know.

The the more times you fail, the more successful you are. If you keep trying again, trying again, you know, the boxing analogy, pick yourself off the map, but it's so true.

Can you share a time that is there anything that sticks out in your past that you really learned the hard way?

I mean, you know, I would say in the last 5 years, spending a lot of money, like, 6 figures plus on technology and that technology not working out and abandon the project. I mean, though those are easy ones, and just the everyday failures day in and day out.

That hurts, spending 6 figures on something that's not gonna work out.

Mhmm. Yeah. It really hurt.

Yeah. I can imagine that. Okay. So I wanna I wanna go down the path of vision and values, and I'm gonna create this visual for you. Okay? So stay with me. If I were to hand you a megaphone or a microphone, I guess I guess a microphone and a megaphone in this world could be the same thing. Right? And you had the chance to speak to every single loan officer out there in the United States. And you're out there for one minute.

What's something and what's a message that you would just wanna shout from the rooftops to have people know or hear?

That's a hard question. You kinda got me on the spot, but, the one piece of advice that I, I would probably say find someone who's 5 years ahead of what you wanna do and see what they're doing. I mean, there's no reason I'm a big believer in not reinventing the wheel. So, there's a lot of successful loan officers out there. Look at what they're doing and and make it your own. Right? You know, that's one piece of advice. And the other what what else I'd say is the only way to grow, not everybody wants to grow, and and that's okay, is to is to find help. Don't try to do everything.

You don't wanna be the maitre d', head cook, bottle washer, waiter. You you need people to help you, or you're gonna you know, we've covered this thing before, or you're gonna work yourself into the ground. You know, it it it's a hard business. There's a lot of expectations set on us, and one person can't do it alone, you know, for decades. You need help. You need help to scale. 1st, become the expert at your craft. No mortgages inside and out, and then and then get help.

You know? Get get assistance, get a great processor, great team, great leaders, and and then go from there.

Well, I can imagine you now shoot shouting that from the rooftop saying,

become the expert. I mean, I kinda do, you know, the hellos that I talk to.

Yeah. Become the expert. Don't try to do everything. I mean, that's for that's for any industry, but especially for what we're doing because it's so easy to get pulled in all different directions. Yeah. That's that's great advice.

Yeah.

Do you think there are myths out there about leadership that you really wish people would just stop believing?

You know, I think one myth, you know, is I think leaders are grown. You know? Some people have more natural leadership than others, but you you kinda just grow into it slowly. Right? And then there's a lot of self doubt when you're a leader too. You know, I question myself all the time. You know, another thing with leadership too, there's different styles of leaders. Right? You know, there's, you know, the leader who's gonna beat their chest and all gung ho, and there's a great speaker. And then there's people who kinda lead quietly by example and don't want the limelight, right, and and kinda lead in the background. And, you know, sometimes those are the best leaders.

It's not always the rah rah rah person. It's sometimes the person who does, and leads quietly in the background.

What style do you think you would fall into? What category?

I think I'm probably a mix of both. You know? I think I'm comfortable in both lanes.

Yeah. And there really is no right or wrong with leadership, you know, I guess, for different styles of of people that need different

In different industries too. Mhmm.

And it's it's interesting with the 3 of you, with Robert and Tom and you, you each have a different style of leadership that you bring to the table, and each with your unique personalities, that's for sure, your strengths, you know, how do you keep the team rowing in the same direction while still allowing everybody to shine, you know, with with each of your different styles?

With the 3 of us?

Yeah.

I mean, we have goals. We have a vision of what we wanna do, you know, each quarter, each year, and then long term. I mean, sometimes you gotta pivot, but we we know our vision, and and that's kind of our guiding guiding principle of of what we wanna become and and what we wanna do.

So regardless of of the personality and the the characteristics that each of you have, staying true to that foundation and the vision and the goal. That's the root of everything.

I mean, like, at any company, I mean, we stray from that. We try to bring it back. And And then we have great we have a great team to kinda, like, keep us keep us true to what we're doing and keep us marching forward.

Yeah. I see that about you guys. I think you do a great job with that.

Well, thank you.

You're welcome. When you are not wearing the mortgage hat, mister Holland, what are you doing? I mean, I know you have a big family, extended family. You know, what's a hobby or interest that really lights you up?

I mean, I like the outdoors. You know, I'm hiking. I'm running on the trails. You know, I do yoga pretty much every every day. I'm running my kids around the soccer and swimming and other stuff like that, in the live music. So, yeah, kind of a good mix of stuff, like eating out.

Nice. Of course. And I know you're a great cook too.

Yeah. Well, my wife's better, but I'm kind of the sous chef, in the arrangement.

Nothing wrong with that. Everyone needs a good sous chef.

Travel. We love traveling, as much as we can. Preferably without the kids. But, when you got 4 young kids, you're gonna bring them along a lot of times.

I know. You're a busy guy. I think sometimes if people don't know you just to see you like, okay. You're just the mortgage guy. Well, no. Data 4, always always got something going on. I mean, I think that really lends to a full life. Absolutely.

And I I really like internally, we we are always talking about, you know, the entire person, not just the mortgage side of somebody, but, okay, those check ins of relationships and

Mhmm.

How how's your stress level? What are you doing to bring joy to your life? And, yeah, just to toot your horn. I think you do a good job of leading by example for that.

The mortgage, Dave, is boring. The real day is much more interesting once you peel off peel off the layers.

Oh my gosh. What would be alright. Well, let's go with that. Well, let's let's get to the interesting, Dave. I mean, I think I think all sides of everybody are very interesting, but what's what's something, for the fun Dave that people would be just maybe a little surprised to know?

The fun Dave, let I went to Vegas this summer, and saw the dead in the sphere. Fundave's really into the Grateful Dead. So, you know, that's Fundave. Fundave loves mountain climbing, climbing big glaciated mountains, when I can get away. So yeah.

Fundave's the man. I love

it. Is fun. Yeah.

That's great. Well, let's you know, going down the, the tunnel of wrapping things up because, you know, you've been you've been very, you've been a great, person to interview, and you've played along with all my wacky questions, but we're we're gonna get weird. So if leadership were a recipe, Dave, because I know you like to cook, what would be some key ingredients, and then what would be things that you would never add to this mix, this lovely recipe for the perfect leader?

You know, I should review these questions in advance, Rachel. Thinking what kind of recipe, what you don't wanna put in the mix is, you know, too much ego. You know, you definitely you need, like, a touch of ego, but you don't want it, like, where it's overarching and look at me, look at me. Because when you run an organization of our size or even just a small, you're on small loan business. Right? You need help. You can't you gotta get a bigger your processors, your underwriters, your closers. And when I was younger, I was so gung ho all the time, and I would just I would just lose it in situations when people made a mistake. Now you just gotta give people a little bit of grace because it's a complicated business.

There's humans involved. There's surprises all the time. So not much ego. I mean, you need to work hard. This is not, you know, unfortunately, a 5 day week business. I mean, I work 7 days a week. I don't work super hard in the weekend, but I do have to check-in with customers and real orders and our LOs here. So you need a dedication to your craft for sure.

This business is not for the light of heart, you know, for loan officers or even, like, process or underwriters at our company. I feel like I'm straying off the question. But,

No. That's great. Yeah. Yeah. No. That's great. Alright. Well, you're gonna really wish you reviewed these questions ahead of time because this is a really good one.

You ready for this?

I'm ready. Yeah.

So if you were going to create a movie about your mortgage career, who would play Dave Holland?

Don't like that question. Don't like that question. Give me give me a good woman actor's name actress name.

Oh my god. Damn it. You've never thought about that? You never thought, like, oh, someone's gonna create a movie of your life or maybe the book. You write the book of, you know, Dave Holland someday, and then it's a best seller, and they're like, we gotta create a movie out of this. You've never thought about who would play you?

Never thought about it once.

Really?

Mm-mm.

People are gonna have to write in and tell us who they think would play you.

Give me some ideas.

I don't know. I was I was hoping you'd have a good one.

I I've actually never thought about that, Rachel.

Wow. Well, now we're gonna have to Google.

Who would you think it would be?

I'm really bad with actors' names, so I'd have to I'd have to research. If anyone has any good comments, you can you can let us know. Who's gonna play Dave Holland in the movie? Alright. So oh, okay. Here here's a super bizarre question to end on. You're you're gonna love it. So if we had to describe your leadership style in terms of a dance move or a song, what would it be? Would it be like the chop jaw? Like, the chop jaw really fast? Would it be like

a wall? Yeah. Let's go with the waltz. Let's go with the waltz.

The waltz classic.

Classic. Yeah.

Enrolled.

Yeah. I like that.

Graceful.

Mhmm. I like that.

Fun. We might cut that. Yeah.

It was going so good.

Oh my gosh. Dave.

You you don't want a ton of time on this, though, do you?

No. We're I'm gonna keep this in here. We're fine. I'm keeping all of this in here.

Okay.

Well, mister Holland, thank you so much for giving me some time today and diving in a little bit deeper, peeling back some layers. I think it's always really cool to ask some strange questions in a different way. So thanks for giving us some of your leadership advice. And

I'm doing great, Joel.

You're welcome. Great to be on with you. And hey, everybody, make sure you like and subscribe. Thanks for tuning into Lending Leadership. We'll see you next time.

Thanks, everyone.