STR Marketing Series - Unlocking the Power of Email Marketing

**Jasper Ribbers:**Welcome back to Get Paid For Your Pad. I'm here with Kaye Putnam, Head of Marketing for Freewyld and Freewyld Foundry. We're continuing our marketing series focused on driving more direct bookings and gaining independence from the OTAs. Kaye, welcome back.

**Kaye Putnam:**Thanks, Jasper. It’s always fun working together since our roles complement each other, my job is to generate demand, and your job is to maximize that demand through revenue management. Today, we're talking about email marketing, which is one of my favorite topics.

**Jasper:**Absolutely. Email is a powerful but underused strategy. Many hosts collect guest emails but don’t have a consistent plan to engage or convert them. Selling to a past guest is so much easier than attracting a new one. But I often meet operators who have thousands of emails and barely send anything. That’s a wasted opportunity.

Airbnb is getting stricter with quality and guest experience, just a couple of bad reviews can get your listing suspended or shut down. You need a backup plan. Email gives you control, and today we’ll talk about building your list, what to send, and how to make it all work.

**Kaye:**Exactly. I was talking to one of our RPM clients recently, and he mentioned he had 6,000 email addresses he wasn’t using. That’s the definition of low-hanging fruit.

If you're in a similar spot, this episode is going to help. And just like last time, I'm sharing slides, head to freewyldfoundry.com/email to see the visual version.

For background, I’ve been in online marketing for over two decades. I started my first business at 16 and now I get to apply that experience to STR and the Freewyld brand. Today we’ll talk about how to build your email list, what to send, and what’s working for us.

And I just checked the stats, we’re at 41 percent direct bookings so far in 2025.

**Jasper:**That’s incredible. Didn’t we set a goal of 20 percent last year? This makes a huge difference for revenue and occupancy. Hats off to you, well, Freewyld cap off.

**Kaye:**Thanks! To be fair, email isn’t the only reason we hit that number, we also talked about influencer marketing last week, but email is a huge part. We’re just shy of 6,000 emails now. The key is: we own that audience. Even if we change platforms, we can reach those people whenever we want. Social media reach is maybe 1 percent; with email, we get 30 to 40 percent open rates.

**Jasper:**And I see we’re adding around 18 new contacts every day. That may not sound huge, but 18 people a day who now know our brand and might book with us? That’s massive. And it’s not just from guests, right?

**Kaye:**Exactly. Some are guests, but many come from other sources. For example, we use a pop-up on our website offering $100 off and a free Wild Mode guide. It’s the same tactic used by major e-commerce brands, give people a reason to share their email. And it works.

We also use StayFi. Want to explain that one?

**Jasper:**Sure. StayFi lets us collect emails from every guest who connects to the Wi-Fi, not just the booker. So if six people stay, we likely get six emails. It also gives us a branded splash screen and other tools for campaigns. It’s one of the most effective tools we’ve implemented.

**Kaye:**And the lead magnet here is Wi-Fi access. Just like in hotels or airports, people expect it. It’s low friction, no complaints from guests. They’re used to it, and it can even make the property feel more professional.

**Jasper:**Totally agree. We’ve never had pushback. In fact, it enhances the brand impression.

**Kaye:**Another thing we’ve done to grow faster is run paid campaigns. We’ve used two types: direct lead generation ads and giveaways.

For lead gen ads, we show cabin content and offer the $100 discount. The cost per lead was under $2. These were hyper-targeted, within a radius of our properties, frequent travelers, luxury preferences. That way we’re building a list of people who are most likely to book.

**Jasper:**Do we have any data on ROI for these $2 leads?

**Kaye:**Not an exact number, but we track click-through rates and see solid engagement. And since we own that connection, we can follow up with events or seasonal promotions that don’t require more discounts. Also, these leads may not convert immediately, but over time, even one booking pays for a lot of $2 leads.

**Jasper:**It’s a long game. And they might refer friends or become repeat guests. Even if 1 out of 100 books, that’s still a good return.

**Kaye:**Agreed. The other strategy is self-hosted giveaways. These generate the cheapest leads, around $0.60 each. People sign up for a chance to win a weekday stay. It’s a great way to build the list quickly. The leads might not be as high-end, but they’re still interested in the brand.

**Jasper:**Right, and we’re just giving away a weekday stay, which has lower opportunity cost.

**Kaye:**Exactly. Now, let’s talk about what to send. The beauty of email marketing is automation. We’ve built a nurture sequence of about 40 emails that go out automatically. Even starting with three to five emails is better than nothing, and you only have to write them once.

We start with delivering the promised incentive, like the coupon. Then we share our brand story, introduce the team, and talk about what makes Freewyld unique. After that, it’s all about adding value: local events, area tips, and content that inspires travel. Think: what would your ideal guest want to read?

**Jasper:**A couple tips I’ve learned from doing email myself before Kaye took over:

First, always be collecting ideas. Jot them down when you’re out and about, don’t wait until you’re sitting at the keyboard with 20 minutes left.

Second, write evergreen emails ahead of time and save them for when life gets busy. That helps you stay consistent, which is key to long-term results.

**Kaye:**Yes! I also keep a “swipe file” in my inbox with emails that inspire me. You can learn a lot from observing what other brands do well.

**Jasper:**If you want great inspiration, sign up at Freewyld.com and watch how Kaye does it.

**Kaye:**We do use more branded designs for Freewyld, even though plain-text often performs better. It’s a conscious choice to elevate the brand experience. But for Freewyld Foundry and our RPM service, we go with simpler designs for higher click-throughs. You can see all of this at freewyldfoundry.com/email.

And quick tips for subject lines:

• Personalization helps.

• Specific numbers catch attention.

• Negative or curious words like “confession” or “warning” increase open rates.

Just don’t overdo it, playfulness is key.

**Jasper:**I saw one titled “Warning: This Town Will Steal Your Heart.” That really worked. You immediately feel the FOMO.

**Kaye:**Exactly. But rotate your language. If every email starts with “warning,” people catch on. Novelty keeps people interested.

And don’t forget, your automated booking emails are also part of your brand. Review them. Add personality without sacrificing clarity. They’re high-impact touchpoints.

So to recap:

• Set up passive collection systems like pop-ups or StayFi.
• Use automations to deliver consistent experiences.
• Analyze your open and click rates to improve performance.
• And most importantly, own your audience. It’s insurance against anything that happens on Airbnb or Instagram.

**Jasper:**Incredible insights. And again, check out the free resources at freewyldfoundry.com/email. Less than 20 percent of the 35 professional companies we work with are actually using email marketing well. If you implement even part of this, you’ll be in the top 10 percent.

**Kaye:**And yes, we will ask for your email when you download the resource. That’s us practicing what we preach. You’ll see exactly how we build trust and grow the relationship.

**Jasper:**Don’t reinvent the wheel. Model what’s already working. Thanks again, Kaye. We’re doing five episodes in this series, and this was number two. What’s next?

**Kaye:**Let’s do SEO next week. Then we’ll cover listing optimization and how to get photos and videos for your STR.

**Jasper:**Perfect. Thanks for listening, everyone. See you next time.

**Kaye:**Bye!