25% YoY Growth and 1.4M Travel Points From His Mortgage: David Dodge on Building a STR Portfolio

Introduction

Jasper: Welcome back to another episode of Get Paid for Your Pad. Today I have a very special guest, my friend and RPM client David Dodge. He is the founder of OR Getaways and an owner-operator in Lincoln City, Oregon. We are going to talk about revenue management and also about BILT, a platform that lets you earn travel points on your mortgage payments. David is an expert on that topic. Welcome to the show.

David: Thanks, Jasper. Awesome to be here. We have known each other for years and we are finally making it happen.

Getting Into Short-Term Rentals

Jasper: Let us go back to the beginning. How did you get into short-term rentals?

David: My wife and I made the transition in 2021. We had a couple of long-term rentals. The appeal of short-term rentals was the higher revenue and the short-term rental tax loophole. That one-two punch made it so we had to try. We jumped in in Lincoln City, Oregon and bought a five-bed. We were freaked out by it initially and were not self-managing. But pretty quickly we bought a second property by December 2021 up in the mountains near Bend. My wife said she was game for self-managing that one, and that led to a lot of momentum. Our first year we went from zero to three properties.

Building the Portfolio

Jasper: You kicked it off with the Blue Whale, the famous five-bedroom in Lincoln City that was crushing it. Then you bought the Ebb and Flow and it blew the Blue Whale out of the water.

David: Exactly. The Blue Whale exposed us to the niche of large properties. Everything else that came after were three-beds and four-beds, but the Blue Whale was five beds and it always had differentiated income relative to the others because of the larger guest count. So then we finished the Ebb and Flow, which was a custom-built vacation rental taking all the best of the Blue Whale and making it bigger.

One of my favorite amenities there is that we put in AC. There are maybe two houses in Lincoln City with AC and now there are three with the Ebb and Flow. Since it was a custom build, we also redesigned the floor plan so that the common areas get the ocean views rather than just the primary bedroom. At the Blue Whale, which we bought off the MLS, the master bedroom overlooks the ocean, which is great for the couple that books it but not ideal for the rest of the guests.

The Duplex Structure and Occupancy

Jasper: Is the larger size the main reason Ebb and Flow is outperforming?

David: The main reason is that it sleeps 20. In our market, per property, you are capped at 16 guests. A little loophole we use is that we build duplexes. No guest who stays at the Ebb and Flow would ever know it is a duplex, but separate water meters and that kind of thing. Each unit has a max occupancy of 16. We did not build a house that sleeps 32, so the practical max in beds is 20. But it is rare to be in a position where you can sleep north of 16 guests. And next door to the Ebb and Flow we are doing an eight-bed that can sleep 24 to make the most of that.

Jasper: When we looked at the numbers, the profitability of the Ebb and Flow compared to the three-bedrooms was just in a different league. In your market, the difference in ROI between a three-bedroom and an eight-bedroom is massive.

Revenue Management with Freewyld

Jasper: Let us talk about revenue management. How were you managing it before we started working together?

David: I was personally doing it. Every Tuesday and Thursday I would spend an hour on it. We had four properties at that point. Then in summer of 2024 my wife and I took on our first management client, and that was right when Freewyld launched. I was eager to go down that path. In truth, I was skeptical as to whether it would work. I was confident in my own abilities. But when we looked at the numbers a few weeks ago, we have been moving at a clip of 25% improvement July over July, year after year. That is kind of shocking to see.

Jasper: I remember when you joined. You were not somebody who did not know what they were doing. I would say you were probably in the top 10 to 15% of best-performing operators we have taken on. So I was thinking it was not going to be easy to beat you. But Patrick has been doing a great job and the results have improved since he took over, which is exactly what you want.

The Risk Tolerance Shift

David: From a quantitative perspective, I am an actuary by training, so I am a numbers and stats person. The biggest difference between when I was managing revenue and now is risk appetite. I wanted the certainty of a booked property. If I had an available summer weekend a month out, I felt uncomfortable. What working with Freewyld has done is follow the methodology. The demand signals are there, keep the price higher for longer, and you will wind up getting booked. That has been a huge difference across the portfolio, particularly for the larger properties.

I used to take the sure thing and lock it down at a lower price. Your team has just done more reps across thousands of properties, so there is a different risk tolerance. Following the methodology rather than my instinct to close early has been the huge ingredient.

Jasper: Your market is super seasonal. June, July, August is probably 60 to 70% of revenue. And the booking window is very long. The Ebb and Flow might book for three thousand dollars a night at peak, but last minute you might go as low as four or five hundred. Managing that whole window, knowing when to hold and when to move, is where the daily focus pays off.

BILT: Earning Points on Your Mortgage

Jasper: Let us talk about BILT. I know about points from credit cards. I have an Amex Platinum and I earn points that I convert to miles. But you told me about this other company where you can pay your mortgage and earn the same kind of points, without it being a credit card. Tell us about that.

David: So BILT, which is spelled B-I-L-T, has been around for a while for renters. What they introduced in February of this year is the ability to earn points on your mortgage payments. For us, we have 22 to 23 thousand dollars in mortgage payments per month. BILT opens up the ability to earn one times or one and a quarter times on those payments.

I built a calculator in Claude that shows the potential. On 22 thousand in monthly mortgage spend and about 18 thousand in monthly credit card spend through BILT, that generates about 739 thousand BILT points per year. On rent day, BILT has transfer partners that earn twice the transfer, so that then translates to 1.4 million travel points per year.

You can redeem those in three ways. You can cash out towards a down payment, which gives you about 11 thousand dollars per year. But the real value is in flights. For my family of four, that gets us 37 economy seats one way or 16 business class seats on international flights. We are only a family of four and there are only so many school breaks. So we can bring more people along on trips, which has been a huge deal.

Jasper: The reason points are so valuable is flexibility. The seats being sold for points and the seats being sold for cash are priced differently. I was just looking at flying to the US for VRMA in October and I might be able to get a business class seat for only twice the points of economy, whereas in cash it would be four or five times the price.

David: Exactly. And the way BILT works for mortgage is not a credit card swipe. BILT serves as a pass-through. My mortgage company draws from BILT, and BILT draws from my checking account. It is ACH, so there is no 3% surcharge. That is the question everyone asks because paying rent by credit card always came with that fee. BILT on the mortgage side avoids that entirely.

The Next Development

Jasper: Tell us about your next build. You mentioned the Pearl.

David: My wife is thinking we call it the Pearl. She just did the electrical walkthrough with the GC and it took five hours instead of one because the GC is so excited about everything we have going into it. We think we can do a 20-guest yoga studio so we can start hosting yoga retreats formally. We have done them at the Ebb and Flow already but did not have a space designed for it. We also want to do a spa with a cold plunge and sauna. These are bolt-ons we are trying to fit into a somewhat small lot, but I think we are going to be able to pull it all together.

The really fun thing about development projects is you take everything you learned from the previous properties and you strive to make it better. We are testing hypotheses. Does the yoga studio work? We honestly do not know. But when you feel called to bring something into the world in hospitality, you cannot not do it.

Closing

Jasper: Before we wrap up, how can people get in touch with you?

David: You can find us on LinkedIn. Look up David Dodge or OR Getaways. We will also be speaking at the IMN Short-Term Rental Conference. And Jasper, I plan to see you at VRMA as well. Anybody doing development or cool things in hospitality, that is what we are after. We are figuring this out as we go but feel called to share the story.

Jasper: Thank you so much for joining. It was really interesting to hear about your portfolio journey and about BILT. If you want to find a solution for your revenue management, go to freewyldfoundry.com/report where we can build a free revenue report and show you where the opportunities are. Thanks for listening and we will see you next Monday.