From Decks to Airbnbs: Creating Multiple Revenue Streams with Derek Prince

20 Sep 2025 · 23 min

Ask about this episode

Ask anything about it. ChatGPT or Claude reads this page and answers with the times it was said.

Connect VO and ask about every podcast you hear, including the moments you saved. Add to ChatGPT · Add to Claude

In short

Epic Entrepreneurs Podcast Episode Notes

Podcast Overview Title: Epic Entrepreneurs Description: The podcast focuses on the realities of entrepreneurship, helping business owners navigate the path to success through real stories of victories and challenges shared by successful entrepreneurs. Host Bill Gilliland, author of "The Coach Approach," utilizes his coaching experience to provide insights into making money, building effective teams, and achieving freedom in business.

---

Episode Details Episode Title: From Decks to Airbnbs: Creating Multiple Revenue Streams with Derek Prince Guest: Derek Prince, Founder of Pro Property Services Description: Derek shares his entrepreneurial journey, emphasizing his transition from exterior contracting to managing multiple businesses, including Airbnb properties and a laundromat.

---

Key Concepts and Discussions

  1. Derek's Background and Business Overview
  2. Pro Property Services: A leading exterior contracting company in Asheville focusing on deck construction, roofing, siding, and cabin restoration.
  3. Additional Ventures:
  4. Airbnb management (85 properties).
  5. Laundromat to support Airbnb operations.
  1. Disciplines from Bodybuilding to Business
  2. Derek draws parallels between competitive bodybuilding and business management:
  3. Discipline and Structure: The importance of a regimented approach to fitness is mirrored in business practices.
  4. Mental Toughness: A resilient mindset is crucial for overcoming challenges in both fitness and entrepreneurship.
  1. Data-Driven Decision Making
  2. Transitioning from instinct-based decisions to tracking key metrics:
  3. Understanding project costs led to improved profitability.
  4. Emphasized the importance of knowing your numbers for effective business management.
  1. Team Building Philosophy
  2. Seeking self-motivated individuals who value personal development.
  3. Hiring to complement personal weaknesses rather than replicate strengths.
  4. Creating a culture of competition and self-improvement among team members.
  1. Common Misconceptions about Business Ownership
  2. Financial Reality: Many believe business owners make a lot of money, but often, profits go back into the business.
  3. Stress and Responsibility: Employees may not see the financial risks and sleepless nights faced by owners.
  1. Advice for Entrepreneurs
  2. Self-Care: Prioritize personal health and spirituality to build a strong foundation.
  3. Know Your Numbers: Essential for identifying profitable practices and avoiding costly mistakes.
  4. Continuous Learning: Invest in personal and professional development through resources like podcasts and coaching.
  1. Expanding Business Opportunities
  2. Discussed the evolution of his business model to include handyman services.
  3. Identified gaps in the market that they could fill with new services, such as a laundromat dedicated to Airbnb clients.

---

Key Takeaways

  • Emphasis on Personal Development: Personal fitness and well-being are crucial for a successful business.
  • Data Tracking is Essential: Understanding financials leads to better decision-making and business growth.
  • Building the Right Team: Focus on hiring individuals who are self-motivated and bring diverse skills.
  • Adaptability: Successful entrepreneurs recognize and seize new opportunities as they arise.

---

Contact Information

  • Derek Prince: [Pro Property Services Website](https://www.propropertyserviceswnc.com/)
  • Bill Gilliland: [Bill's Website](https://billgilliland.biz/) | Email: williamgilliland@actioncoach.com

---

Conclusion This episode offers invaluable insights into the integration of personal discipline into business leadership, the importance of data in decision-making, and the strategic expansion of services in response to market needs. Derek Prince's journey illustrates the tenacity required in entrepreneurship and the rewards of building a well-structured and motivated team.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Hear the part that matters, and keep it.Open this episode in VO. Double tap your headphones to save a moment as you listen.
Get VO free

Transcript

Automatic transcript. May contain errors.

0:02Hi, and welcome to this week's episode of the Epic Entrepreneurs podcast where we are all about helping business owners just like you achieve success. So we don't do fancy smancy. We don't do flashing lights. We don't do a lot of things that a lot of podcasts will do. These are just real stories about real people and their entrepreneurial and business experiences. We go into their wins, their challenges, and their learnings. So we hope you enjoy it.

0:36hey there welcome to this week's episode of epic entrepreneurs i'm bill gilliland your host i am the owner of action coach business growth partners and also one of the founders of the ashville business summit so uh super pumped with you today hey there's still time to get tickets to the summit it is september 23rd we got a couple of weeks to go as of this recording it'll probably be about a week when you hear this so just go ahead and get your tickets you can go out to wncsummit.com but i am super pumped today i have got derek prince from pro property services on the line i'm super pumped to hear his story i know you're going to want to hear it too so derek welcome to the show thanks for having me i appreciate you having me on yeah yeah so derek tell us what what the heck is pro property services and and and what's that all about yeah so best way to describe pro property services that we are a ashfield's premier exterior contractor so we do deck siding everything besides landscaping so we do roofing we do a lot of cabin restoration as well so we blast them down and restain them and log repair or a lot of replacement.

1:49That's kind of our niche. And my wife's side of the business, she manages about 85 Airbnbs, and she has a whole cleaning team, and we've got a laundromat that we're starting up to provide laundry services for those Airbnbs. Wow. Okay, so you really got two businesses here. Yeah, pretty much. Yeah, yeah. All right. So let's talk about both of them. We'll have fun with this. That'll be cool. Yeah, I like the Airbnb piece is a good business. And I know exterior contracting. We work with a lot of contractors and folks and subs, that sort of thing. Anybody who's got trucks, vans, crews, that's kind of our thing.

2:43So let me ask you a question, though. I mean, you've obviously been doing this a while. if you've got that kind of a portfolio. If you had to start over in business, what would you do differently? I would hire a coach almost immediately. Nice. Yeah, first couple years didn't really make a whole lot of money. Didn't even know there was coaches for this type of thing. I'm a bodybuilder, a competitive bodybuilder, so I had coaches for that.

3:15and didn't really know if there was business coaches or anything like that. And so, yeah, I would go back and get mentors and coaches from the get-go. Yeah, no, I love that. Thanks for saying that. So what have you – this is a little bit off script, but I've got to talk about bodybuilding a little bit here now that we've brought it up. What are some of the similarities? What have you learned from bodybuilding that you've been able to take over into business? The discipline, the structure, inputting certain foods at certain times to get different results, adding certain physiological changes, adding cardio, taking cardio out, and kind of manipulating that thing to either maintain muscle, grow muscle, or maintain muscle and lose body fat.

4:09to get stage ready and the mental toughness that you get from it, that you get from business as well. Yeah, it seems to me that like what I heard was that, you know, you have to adapt to your specific situation. So not every, you know, exterior build or remodel is going to be the same. I mean, they're all different. You got to adapt and have a plan depending on where you are for that. I love that. I love it. I think, you know, I feel like most of the entrepreneurs and clients that we've worked with, they almost always have something outside where they're working on themselves in addition to just working on themselves in the business.

4:58It's sort of mind, body, spirit. So I love that. I feel like that's what's helped me grow so much is having a strong foundation because I can't control everything in the business, but I can't control my fitness and what I'm putting in my body. So keeping the foundation strong keeps everything because we are our business. 100%. Yeah, you got to have it. So what have been some of your biggest learnings as an owner and an employer since you started? learning to track, tracking things and knowing exactly like what it cost me to do something and hitting a certain, what it costs from the cost of a lead to the sale, to produce a job and job costing at the end of the job.

5:50That was game changer to actually see, you know, like it's like being sick and not having a diagnosis, you know, exactly what's going on you're kind of just i think i did good on that job i'm not sure but actually at the end of every job you know grading it pretty much and then figuring out catching those mistakes way ahead of time before i do two or three jobs at that and you know get getting a bigger hole that was that was probably the biggest thing for me is learning my numbers and uh learn what it cost actually cost me to do do some projects yeah you gotta know your numbers Got to know your numbers.

6:27So what do you think some of the common misconceptions are about running a business? That's a good question. That the owner makes a whole lot of money. Yeah. That you don't do anything, you know, maybe, especially when you step outside of actually being in the field and working on the business. Sometimes you'll have employees that think you're making a killing and they don't see the ebbs and flows and the stress and the sleepless nights that, that you go through, you know, cause the buck stops here, you know, and, um, you know, sometimes you don't get paid, uh, you know, especially in the early days and everybody else does.

7:11And that happened for a couple of years where all my employees were making more money than I was, which is, which fine take care of them. But, um, yeah, I would say that is probably the biggest one that you own a business, you've got, you know, all this money coming in, but it tends to go right back out. Yeah. Yeah. They don't see it. Well, that was an$80 ,000 job, but they don't see, I mean, it's sort of like they forgot what they have expenses at home. Yeah. Yeah. It's, it's always been interesting to me that, you know, they, they forget like, all right, well, I got a rent or mortgage payment.

7:45I've got a, you know, I've got electric, I've got water, I've got, you know, insurance, I've got car payments. I, you know, it's like, they don't think hey just because it's a business it's the same thing it's just big numbers right you know you know so it doesn't end up yeah it's it's a bit crazy so what do you attribute your growth to um being i would say you know as uh somebody who's into self-improvement and always want to get better pretty competitive naturally anyway um so just striving to be the best um I'm one of those people I want everybody to win, but I also want to beat you. I love that.

8:29Yeah. You can win as long as I beat you. As long as I win, then I'm better. Yeah. Yeah. Yeah. No, that's funny. Well, I think that helps. I think a competitive spirit really helps in business. I mean, cause it is a game. It is, you know, it's a, it's a game, you know, we just keep track with money. So it's a, it's an, yeah, it's an, It's an interesting one. So how do you balance the personal and business sides? So I'm blessed to have some really good people in place in my business to where I'm not having to put 12 hours in every day. So I've got sales reps. I've got an office manager, good project managers and stuff like that.

9:16I've been through quite a few of them to kind of find out exactly what I'm looking for and that we're all on the same page. So all of my crew are pretty close to me. You know, they're all self-motivated, into self-improvement, into fitness, a lot of them. And that seems to be our culture is that we're competitive. We're taking care of ourselves. So that helps, you know, take care of them financially as well. Um, so, you know, I, I make sure I get my training in the morning before I go to the office, you know, come on, come into the office for eight or nine hours and work on the business, leave by three or four and then go to the gym again, you know, go to church, stuff like that.

10:05And, you know, keeping the mind, body and spirit in place. And, uh, yeah, I love reading the podcast, you know, uh, So just everything that I do, I try to afford momentum. Nothing that's holding me back, you know. I love it. I love it. Cool. So you said you had a great team. So obviously you've been through a few teams that probably wasn't – I mean, they might have been good at the time, but they've cycled off or whatever. What do you look for in employees these days? Um, somebody who's motivated, somebody that shows up on time, you know, that first couple meetings, uh, you know, when I'm interviewing, are they five minutes early?

11:01Uh, stuff like that. Um, I asked about the personal life a little bit, not too much, but like, do they have a good family life as far as, you know, are they married? Are they single? Are they out partying? That's that type of stuff. Those are some red flags for me. Yeah, good family. Foundation is key for me. So they're, you know, can be more reliable. And for me, like especially on the sales side, like I said, I look for somebody who takes care of themselves. It doesn't have to be bodybuilding. It could be anything outside of it. It could be karate. It could be yoga. It could be anything like that.

11:40But something that they're working on themselves outside of work I just stumbled upon that recently, and that seems to be the formula for me. No, that's a good one. I mean, it's kind of who you are, so you naturally should be attracting those kinds of people anyway. It doesn't mean you want clones because that don't work. Right, right. Exactly. Definitely. I mean, if you had 100%. I would say, sorry to interrupt, one more added thing is finding people that are better at things than I am. yep smarter like not always being the smartest person in the room so um some people are better at talking than me some people are better at doing spreadsheets and computer stuff um and stuff like that so i try to find areas that i lack in and find the people that are better at that than me i love that i love that so one of our taglines is be epic and it's an acronym.

12:41So I'm going to ask you, I'm going to give you the letter or the letters and just get your quick, like a quick thought, like a couple of words or sentences about each one just to get your thoughts on it. So I think this one's going to be easy. The B stands for bring the energy.

13:00Like just like describe it or? Yeah, yeah. Just give me a couple of words or sentences that come to your mind when I say bring the energy. Be motivated, be positive mindset uh be focused i love it e is for education uh self-improvement um

13:23education uh always trying to be better i guess no i love it no education self-improvement you know jim rohn said work harder on yourself than you do on your job you know if you want to be successful so uh p planning uh knowing your numbers strategizing um and um have a game plan well i love that i love that i stands for inspiration uh being a lead as a as the owner leading from the front um you know you can't ask somebody to do something that you you're not willing to do. And so, yeah, leading from the front. I love that. Lead from the front. Yep. Got to be out there. And the C stands for commitment.

14:14Yeah. Being fully committed to our principles, our commitment to the customer, and to delivering a great product and service. Love it. So what words of advice would you offer? to other business owners who are looking to grow?

14:38I would say take care of you. It starts with you first. So start taking care of your health and spirituality, whatever that looks like for you. Because when the storm comes, if you don't have a strong foundation, other vices tend to fill that gap, whether it's alcohol or anger, that sort of thing. So taking care of you first and foremost so you can take care of others. Diving into the numbers and knowing your numbers. I wish I knew that from the get-go. And then investing in yourself and your business. That's what that looks like. I know not everyone can hire a coach right off the bat, but, you know, looking at there's a lot of free content online, podcasts, and just one thing I did from the get-go when I was flat broke, didn't have any jobs lined up.

15:36My wife was like, you need to get up. I was kind of depressed, and she's like, you need to get up and go do something. So I got up and decided I was going to ride around and pass business cards out, but I'm going to use every little bit of time to get better, so I wouldn't even listen to music. I'm going to listen to a podcast as I'm driving around. uh and yeah just utilize each time you know as much time as you can to to get better and on and off the job yeah and i love that i call it car college yeah you just you know don't yeah music's okay from time to time to get you fired up or whatever but you know there's a lot of time in vehicles or walking or whatever it is you're doing between things where you could be learning So, you know, we have a saying that only place, you know, earning comes before learning is in the dictionary.

16:32So, yeah, so you got to learn. Hey, this has been awesome. So I know you've got, we've been mostly talking about the construction side of the business. All of this stuff applies to the other side of the business as well, I'm sure. but talk a little bit about that business and what you've learned over there. Yeah. So my wife was a registered nurse during the COVID era and she got a little burnt out on craziness. So we decided to add a cleaning service because we're already at the home and I've had a few people ask me anyway. So she started that four years ago and she's done a great job growing it.

17:18Um, and what we've learned over there is a little bit different, uh, as far as cashflow goes, you know? Um, and then it's one thing I we've noticed with, with that is she doesn't get any of the praise that we do, you know, like once we complete a deck and the customer's happy, get a good review. Well, most of her stuff is a lot of negativity because a guest finds a piece of hair, you know, and then once they find that, then they go looking for everything. Um, so that's a struggle for her is, uh, finding some positivity in it. Um, it does do pretty well as far as, you know, consistent income. Um, but getting, getting payments has been a struggle from, cause we pay the girls and then waiting on the payment from the homeowner can be a struggle um and we have inspection an inspection lady goes in and inspects the cleans after the girls are done um and then finding good help to be honest with you that's been the struggle on that side um so but there's room to grow uh as we we found that the construction side is a little too expensive for that clientele with the airbnbs for on our side so So you would think that would lead to work, you know, us working on those homes, but they tend to be out of our price range because we're more higher end on that side.

18:50Right. So we've took on a couple of handyman, hourly handyman. Yep. Because there's money there and we want to take advantage of it. But also finding reliable handyman has been a struggle. and then we just recently hired a we call her an office manager so she's going to be answering the phone for the construction side you know doing the admin stuff for that and then with her side is getting back to the homeowners and with the airbnbs the scheduling is always changing so fast even on the weekends like ours you know it shuts off at on friday but hers is saturday and sunday and having that communication with the homeowners asking answering questions um so we finally got and my wife has been doing all the invoicing and all that stuff for that side and that's a all day all day task and so we're trying to free her up so we can focus on building the handyman side and also uh we've we just got a 1600 square foot facility and we're putting in i think 10 washer and dryers in there um and that's that's kind of to go to supply the linens for those airbnbs and that's we see a huge opportunity uh with that we just got to get it up get her freed up so she can focus on that and yeah so you've added a third business really, which is the handyman business.

20:24So it's a different business than your other business. I mean, it sounds like it's construction, but it's just not. Yeah. I mean, cause you might, I mean, you know, I've, I've, I've had clients who were in the handyman business. I mean, they sometimes just change light bulbs. I mean, it's not like it could be just about anything. I mean, it could be major, it could be a remodel job, but it could also be a, uh, yeah, it's an, that's an, That's an interesting thing. I love how you guys have just sort of morphed into the opportunities. You saw what was there, and then you've looked for what's next.

20:58Right. Yeah, and I love that. I love that. That's great. So lastly, what's the best way for somebody to get in touch with you? You can go to our website, ProPropertyServicesWNC.com. Our phone number is 828-202-1328. is our phone number. No, I love it. Well, fantastic. Listen, thanks for being on here. There's a lot of good wisdom here. There's a lot of good experience here. Appreciate what you're doing in the community and all the things that you're doing. And it sounds like you guys are serving a big need on both sides of the, well, all three sides of the business at this point. It's going to be, yeah, but it's fun.

21:44I love the entrepreneurial drive. Congrats on your success so far. And certainly wish you continued success. Thank you. I appreciate you. Thanks for having me. Yeah. Hey, and until next time, all the best. Thanks. Hey, thanks for listening to the Epic Entrepreneurs podcast. Here's three things that you can do. Number one, remember to subscribe to the podcast. It takes very little effort on your part. It's going to help you and your fellow entrepreneurs. Plus, you guys know how it works. The more subscribers we get, the more cool things we can offer to you. Second, to learn more about growing your business, just download my book, The Coach Approach.

22:29It's free for you at giftfrombill.com. That's giftfrombill.com. Hey, and if you'd like more info about growing your business and what we can do to help you grow your business, send me an email directly. Just send it to williamgilliland at actioncoach.com. That's my personal email that I read. No one else reads it first. It's not screened. It's my real email. Just send it to me. I can't wait to talk to you. Hey, and until then, all the best.

From the publisher

Derek Prince takes us behind the scenes of his entrepreneurial journey as founder of Pro Property Services, Asheville's premier exterior contracting company specializing in deck construction, siding, roofing, and log cabin restoration. But this isn't just a story about building physical structures – it's about building multiple successful businesses with intention and purpose.

What makes Derek's approach unique is how he's transferred principles from competitive bodybuilding into business leadership. The discipline, structure, and mental toughness required to excel in fitness have become cornerstones of his business philosophy. "I can't control everything in the business, but I can control my fitness and what I'm putting in my body," Derek explains. This foundation-first mentality has helped him weather the inevitable storms of entrepreneurship without falling into destructive coping patterns.

The conversation reveals crucial turning points in Derek's growth trajectory, particularly when he began rigorously tracking his numbers. Like many contractors, he initially operated on gut feeling rather than data. Learning precisely what each project cost to complete transformed his decision-making and profitability. Derek also shares candid insights about team building, explaining how he seeks self-motivated individuals with interests in personal development outside work. His formula? Find people who complement your weaknesses rather than mirror your strengths.

Most fascinating is how Derek and his wife have expanded beyond contracting into Airbnb management (currently overseeing 85 properties) and launching a laundromat specifically to service their vacation rental business. This ability to spot adjacent opportunities and build complementary services demonstrates the entrepreneurial mindset at its finest.

Whether you're struggling in the early stages of business or looking to scale multiple revenue streams, Derek's practical wisdom offers a blueprint for sustainable growth. Listen now to discover why knowing your numbers, investing in personal development, and building the right team culture might be the most important projects you'll ever undertake.


Derke's information:

Website: https://www.propropertyserviceswnc.com/

Facebook: https://www.facebook.com/propropertyserviceswnc

Thanks for Listening. You may contact me or our team at https://billgilliland.biz/

All the best!
Bill

Thanks for listening. Please hit the subscribe button, leave us a 5 star review, and share this podcast. You can reach me at williamgilliland@actioncoach.com or at https://billgilliland.biz/

All the best!

Bill

More from Epic Entrepreneurs

All 219 episodes
From Decks to Airbnbs: Creating Multiple Revenue Streams with Derek PrinceEpic Entrepreneurs · 23 min
Listen in VO