From Hurricane Loss to 70 Rentals: Scaling STR Business

Kaye Putnam: Welcome back to the Get Paid For Your Pad podcast. I’m Kaye, and today I’m excited to be interviewing Joe Prillaman from Host Help, one of our Revenue and Pricing Management clients at Freewyld Foundry. Joe operates primarily in the Wilmington, North Carolina area, and today we’re going to talk about his growth journey, what he’s learned along the way, and how his business evolved through some major challenges. Joe, welcome to the podcast.

Joe Prillaman: Thanks for having me, Kaye. I’m honored to be here.

Kaye Putnam: You have a partner in the business. You and Grant run Host Help together. When did you two get started?

Joe Prillaman: Grant is actually one of my best friends from college. We’ve been working together for a very long time, even before getting into short-term rentals. Before that, we sold industrial equipment together, which was quite a journey. We covered 13 states and drove everywhere. We would spend three to four thousand miles at a time in the car together.

We realized after all of that time that we didn’t hate each other, so we figured we might as well become partners and keep hanging out.

**Kaye Putnam:**That’s honestly one of the best ways to stress-test a partnership before committing.

**Joe Prillaman:**Exactly. As far as what we each bring to the table, I’m the visionary. I’m the chaotic, idea-driven person. I love starting new ventures, networking, sales, and connecting with people. Grant is the integrator. He takes all of my chaos and breaks it into individual steps that actually get accomplished, keeps people accountable, and keeps everything moving forward. It’s been the perfect balance for us as we’ve grown and scaled.

**Kaye Putnam:**You’re at around 68 properties now. What has that growth trajectory looked like?

**Joe Prillaman:**Originally, we were only managing properties that I personally owned. We had built the company around about 30 units, mostly in North Carolina. That included Carolina Beach, Kure Beach, and Banner Elk. We also had a couple of midterm rentals in Winston-Salem and Chapel Hill, but we ended up selling those.

Then Hurricane Helene hit Banner Elk. Two weeks before that, we had some major flooding in Carolina Beach. Within a two-week span, I lost about a third of my portfolio because of those events. That was the moment we went headfirst into property management for other owners.

That was about a year ago. We went from around 30 units, down to closer to 20 after the losses, and now we’re close to 70 properties. We’ve signed a few more recently, and that pivot completely changed the trajectory of the business.

**Kaye Putnam:**That’s an incredible example of turning a catastrophe into an opportunity. What was your mindset in that moment when everything happened?

**Joe Prillaman:**It was awful. At the same time, we had always planned on building a management company eventually. The disaster just poured fuel on the fire. We still had mortgages. We still had a team. We had no option but to figure it out.

Grant and I spent a lot of time in whiteboard sessions asking ourselves how we could add as much value as possible to as many people as possible. Managing your own portfolio is very different from managing for homeowners. We went from being great self-managers, with strong reviews and systems, to helping homeowners get their properties up to that same standard while being accountable to them.

There was a lot of stress, anxiety, and pain during that time. But a year later, I can honestly say we’re in a better position than I ever imagined. That crisis launched us forward by what feels like ten years compared to where we would have been otherwise.

**Kaye Putnam:**Once you made that decision, how did you start attracting and onboarding management clients?

**Joe Prillaman:**I had already built a reputation in Wilmington as the short-term rental guy. I had started a meetup group, posted on BiggerPockets for years, and worked as a high-producing real estate agent focused on short-term rentals. I had a large network of people in the industry.

I literally sat down with a pen and paper and called everyone I knew. For years, I had told people I wouldn’t manage their properties, but I’d teach them everything I knew. That part didn’t change. The only difference was that instead of saying no, I finally said, “If you want us to do it for you, we can.”

There’s no magic behind what we do. It’s just good work, done consistently.

**Kaye Putnam:**What does your playbook look like? What really drives success?

**Joe Prillaman:**I always say it’s the three C’s: cute, clean, and comfortable. It’s about fighting for five-star reviews and bending over backwards for guests. We built our standards early on Airbnb, where you either perform at a very high level or you disappear.

Fighting for five-star reviews means setting expectations properly, having great photos, being responsive, and building systems for when things inevitably go wrong. Door locks fail. Internet goes down. Guests don’t know how to use things. We prepare for all of it.

For example, every property has multiple backup lockboxes and keys. We build redundancy into everything so guests are never stuck. It’s about setting the property up for success and putting yourself in positions to get lucky.

**Kaye Putnam:**What are the biggest challenges when it comes to getting other people’s properties up to your standards?

**Joe Prillaman:**It really comes down to onboarding. Quality is free in the long run. The more work you do upfront, the easier everything becomes later.

We didn’t have that luxury at first. We were onboarding properties quickly to save the business. That taught us, through trial and error, what actually needed to be standardized. Now we use massive checklists built from years of experience.

Every property is different. Some owners are completely dialed in and just want to hand over the reins. Others need full restaging, professional photos, systems, and equipment just to be operational. There’s no one-size-fits-all approach.

**Kaye Putnam:**Let’s talk about pricing. What has it been like working with Miles on revenue management?

**Joe Prillaman:**Miles is a monster, in the best way. Pricing was my bread and butter. Letting someone else take that over was humbling, but he’s simply better at it.

At 30 properties, pricing is manageable. At 70 or more, you need someone full-time who knows your portfolio better than you do. The biggest win for me has been the freedom. I can focus on serving homeowners and guests, knowing pricing is being handled at an elite level.

**Kaye Putnam:**What does your team look like today?

**Joe Prillaman:**We have about ten team members. Grant and I lead as visionary and integrator. We have directors for operations, communications, cleaning, maintenance, and technology. We also have quality control specialists and someone focused specifically on AI and automation.

With our current structure, we can comfortably manage around 150 properties. When we hit that point, systems will break again, and that’s normal. Then we’ll go back to the whiteboard and rebuild.

**Kaye Putnam:**What does your day-to-day look like now as an owner?

**Joe Prillaman:**I’m no longer the person in the field fixing things or winterizing properties. My role is oversight, leadership, marketing, and sales. We spent the last year building the machine before turning on marketing. Now we’re confident enough in our systems to start putting our name out there.

**Kaye Putnam:**How do you prepare for weather-related risks, especially in coastal markets?

**Joe Prillaman:**You don’t really appreciate fundamentals until life hits you with a shovel. We built detailed policies for hurricanes, floods, and winterization. We made sure insurance coverage is aligned across owners, guests, and our management company.

We also require guest insurance policies. You hope to never use them, but preparedness matters.

**Kaye Putnam:**How do you stay profitable in a beach market?

**Joe Prillaman:**You need scale. Around 65 to 70 properties is where you can finally afford the team you actually need. Before that, founders are doing five or six jobs at once. After that, the business becomes sustainable.

**Kaye Putnam:**How do you balance work and family?

**Joe Prillaman:**It’s possible, but it’s not easy. My wife and I committed to the grind early. We house-hacked, cleaned properties ourselves, and did the work. Now she gets to stay home with our kids, and I get to build something meaningful.

**Kaye Putnam:**What advice would you give yourself two years ago?

**Joe Prillaman:**Build stronger habits and prepare for stress. It’s going to be hard, but it’s worth it.

**Kaye Putnam:**What advice do you give other property managers most often?

**Joe Prillaman:**Delegate sooner. Trust people. Build systems. Remove ego. That’s how real scale happens.

**Kaye Putnam:**How are you using AI in the business?

**Joe Prillaman:**AI handles about 55 to 60 percent of our guest messaging through HostBuddy. It reduces workload but doesn’t replace people. It amplifies the team so they can focus on higher-value work.

**Kaye Putnam:**Joe, this was an incredible conversation. Thank you so much for sharing your journey.

**Joe Prillaman:**Thank you so much for having me.