Guest Experience, Revenue Hacks & Mindset Shifts for STR Success

**Jasper Ribbers:**Welcome back to another episode of Get Paid For Your Pad. I'm Jasper Ribbers, co-founder of Freewyld and Freewyld Foundry. Today, I'm joined again by a guest who always takes action, Derek Gizriel. He was on the show back in May 2023, and a lot has happened since then. Derek, welcome back.

**Derek Gizriel:**Thanks Jasper, it's great to be back. Yeah, a lot has changed since our last conversation, and I'm excited to dive in.

**Jasper:**Let’s start with a quick recap of your journey since launching Level Up Stays.

**Derek:**When I got started, I was working full-time and was a part-owner in a residential solar company. We always wanted to get into real estate, but the options were endless. We were drawn to STRs because of the guest experience and improvement aspect. In October 2022, we bought our first property, a 5-bedroom in a remote vacation rental market outside San Antonio, Texas.

That property historically brought in about $64K annually. We gave it a 49-day refresh, paint, new furniture, redesign, no major renovations. It brought in $13K in the last few weeks of 2022. In 2023, we hit $160K. Then $190K in 2024.

We added two more new-build homes in that same neighborhood and launched Level Up Property Management in summer 2023 because other owners started asking for help. As of now, we manage 26 properties and aim to hit 50 by year-end. Our portfolio revenue has already surpassed the million-dollar mark.

**Jasper:**Incredible growth. One of the things I remember from your last appearance was your focus on guest experience. It's clear that mindset has paid off. But today I want to dive into your consistency with content creation.

You were part of our Legends X program, where we teach the Property Abundance Plan to help hosts market their brand through content. Most start strong but eventually drop off. You've stayed remarkably consistent. What’s your secret?

**Derek:**Consistency has been key. I work with a coach who always says January is "quitting season." People start with high goals and fizzle out by week three. What’s worked for me is simple weekly planning. Every Sunday, I write out what my week looks like, drop-offs, pick-ups, and the open blocks of time in between.

That’s when I schedule content creation. Every 3 weeks, I block a half-day to record long-form videos for YouTube. From one video, we can create 20+ clips for Instagram Reels. The shift from short to long-form was strategic, we realized our owner avatar consumes more detailed, educational content.

**Jasper:**That planning sounds simple but powerful. But do you ever have days where you just don’t feel like recording?

**Derek:**All the time. Life happens, kids get sick, things come up. But just like working out, the trick is to show up. Even if you tell yourself, “I’ll just record one thing,” you usually end up doing more. The hardest part is starting.

We batch film so my social media team can do the editing and repurposing. Tools like Riverside FM help too, it automatically pulls reels from the interview footage. Technology has made the process easier.

**Jasper:**Totally. That “show up and start small” mentality is huge. I used to tell myself: just go to the gym, no workout required. Once you're there, you’ll do something. That low barrier gets you going.

**Derek:**Exactly. You have to choose your hard. Content creation is hard, but so is being invisible online. We do annual offsite retreats, our last one was at Onira, a boutique STR community in Wimberley, Texas. We used that time to plan 2025 in detail. Getting out of the usual environment sparks creativity.

**Jasper:**We’ve been following Onira too. It’s a beautiful example of what’s possible in this industry. Let’s shift gears, your portfolio growth is impressive. What lessons have you learned that other operators could benefit from?

**Derek:**We hosted 6,600 guests last year and maintained a 99.6% 5-star rating. That comes down to guest experience. From personalized welcome notes to digital guidebooks, to the way the home smells when they walk in, it all matters.

If something goes wrong, we take responsibility and often offer compensation. A refunded cleaning fee or a night’s stay can go a long way. We're not perfect, but when you care personally and consistently, guests feel it.

**Jasper:**Airbnb is leaning harder into quality. Listings with 4.5–4.7 star averages struggle. There’s even a hidden badge that flags listings in the bottom 20% performance-wise.

**Derek:**Exactly. We aim for Guest Favorite badges within the first 90 days of launch. That’s our stabilization period. We might lower pricing to get more reviews early on. It’s an investment that pays off with social proof and pricing power later.

**Jasper:**Let’s talk about revenue strategy. On a recent mastermind call, we discussed using length-of-stay discounts in PriceLabs. You implemented a change mid-call and messaged me that it earned $10K in bookings. Share that story.

**Derek:**That call paid for itself tenfold. We set some of our 5–6 bedroom homes to "Aggressive" pricing profiles in PriceLabs. It lowered off-season rates slightly but raised the ceiling during peak season. We booked over $9,000 within 24 hours.

That’s the value of taking action, not just learning but implementing immediately. Our best-performing listings have constant fine-tuning happening behind the scenes.

**Jasper:**Yes! Most hosts use dynamic pricing like a “set-it-and-forget-it” tool. But those who optimize consistently outperform the market. Let’s wrap with a final reflection, what’s your message to hosts who feel stuck or overwhelmed?

**Derek:**You don’t have to do this alone. Join a community. Find people ahead of you and learn from them. Our success isn’t built from scratch, we refined what others had already tested and shared. If you're struggling, the support of others makes all the difference.

**Jasper:**Absolutely. And if you're looking to level up your pricing game, grab our free training at freewyldfoundry.com/acp. We’re also offering free pricing audits for portfolios with 15+ listings.

**Derek:**If you want to connect, find me on Instagram at @derekgisriel, on YouTube under Level Up Stays, or visit staylevelup.com. Our content is 100% value, no pitch, just insights from the frontlines of STR.

**Jasper:**Thanks so much for joining us, Derek. We’ll definitely have you back again. And for everyone listening, we’re now publishing episodes every Monday and Friday. Thanks for tuning in!