The David Greene Show Episode 106: Behind the Scenes STR Reveal Part Two with Angela Heydorn Date: January 9, 2026

Overview

This episode is the second part of a deep dive into a short-term rental (STR) project nicknamed "Bear Cub in Transformation." Host David Greene and guest/co-investor Angela Heydorn share actionable strategies, lessons learned, and real numbers from their STR turnaround. The episode focuses on optimizing underperforming properties, incremental improvements, dynamic and human-driven pricing, and the critical role of photography and guest targeting. Whether you’re struggling with occupancy, pricing, or upgrades, this episode offers a candid, unfiltered look at how to boost STR performance in a competitive market.

Key Discussion Points & Insights

1. Incremental Upgrades: Focus and ROI

(01:15 – 05:27)

• Small Changes Over Big Renovations: Angela explains that owners don’t need to overhaul properties all at once. Identify high-impact, cost-effective upgrades—like new comforters, wall art, or pops of color.
  • "You don't have to spend $100,000... you can do it and get the biggest bang for your buck." (Angela, 01:16)
• Tiered Approach: David outlines a three-tier upgrade system:
  • Tier 1: Highest ROI (games, new photos, fire pit).
  • Tier 2: Bathrooms/kitchen upgrades, better patio furniture.
  • Tier 3: Expensive amenities (e.g., pools).
  • "The money you got from phase one can fund phase two... if you want to do phase three..." (David, 03:18)
• Photography: Invest in new, high-quality photos after upgrades. Even one extra booking justifies the photographer’s fee.
• Cash Flow Strategy: Improvements are paid for with increased revenue from previous upgrades—a cycle of reinvestment.

2. Before & After: Real Results from Upgrades

(05:27 – 08:39)

• Pre-Upgrade Performance: $13,000 gross revenue in seven months after taking over—a big swing from the previous manager’s losses, but still lackluster.
  • "That is still 17 grand more than when somebody else was managing... that's a $17,000 swing." (David, 06:01)
• Post-Upgrade Metrics:
  • 23% occupancy increase.
  • Revenue doubled in the most recent two months.
  • Average length of stay jumped from 3.9 to 6.7 days.
  • "When we updated the cabin and then we got new photos, we knew that was going to happen. But 23% is pretty—I feel pretty good about that." (Angela, 07:06)
  • "Now they're seeing this as a place, 'Oh, I can stay for a while and be comfortable for five, six, seven days.'" (Angela, 08:39)
• Story: The property went from last-resort bookings to attracting longer, planned family stays.

3. Dynamic Pricing: Occupancy vs. Rate

(09:31 – 13:56)

• Two Revenue Levers: Occupancy and average daily rate (ADR); need to find the balance.
• Initial Strategy: Prioritize high occupancy to get reviews and algorithm traction, then increase ADR incrementally.
  • "Let's sprint to get high occupancy... Once we get to that point that occupancy was high... now we're going to look at how to get more per night..." (David, 09:31)
• Testing Pricing: Push ADR until it limits bookings, then dial back. Each upgrade cycle can justify another rate bump.
• Minimum Stay Adjustments: Strategic tweaking of minimum stay requirements to close orphan gaps and maximize longer bookings.

4. Data & Design: Outperforming Competition

(11:35 – 13:56)

• Know Your Avatar: Continuously study the competition to understand guest preferences and booking trends.
  • "First of all, you need to know who your avatar is, figure out who your guest is. Who are you trying to market to?" (Angela, 12:02)
• Every Property is Unique: No cookie-cutter solutions; tailor amenities and marketing to each property’s strengths and its target guest.
  • "Every property has its own unique strengths and weaknesses... What I want to do is figure out who is this property meant to appeal to and how do I maximize that?" (David, 13:56)
• Photography Tactics: Analyze top-performing listings for photography and visual trends, but stand out with different, eye-catching hero images or collages.
  • "Your first picture is not supposed to look like all the other ones. Your first picture is supposed to make them want more." (David, 15:38)

5. Hands-On Management Beats Automation

(19:47 – 23:03)

• Three Operator Types:
  1. No dynamic pricing or tools—static pricing.
  2. Only automated pricing tools.
  3. The Winning Approach: Combine dynamic pricing with daily human review and adjustments.
     • "You have to be paying so much attention... also looking at what is your minimum day stay." (David, 21:05)
• Tools Used: PriceLabs, Hospitable, AirDNA; but personal attention outperforms automation alone.
• Hyper-local Awareness: Track events (e.g., car shows, festivals) and adjust listings or pricing accordingly to attract relevant bookings.

6. Lessons from Losses: Don’t Clone the Competition

(25:56 – 27:17)

• Angela’s Beach House Story: Buying blindly into a ‘hot market’ (Crystal Beach, TX) and copying competitor listing styles led to poor performance.
  • "I knew within probably six months. Oh, shoot. What did I just do? ...It looked like the other ones—the same." (Angela, 26:06)
• Avoid Homogenization: Find ways to set your property apart visually and experientially, while honoring its location and vibe.

7. Actionable Advice for Struggling STR Owners

(27:17 – 29:07)

• Stand Out, Not Stick Out: Don’t break the mold, but add distinctive twists to create memorable, compelling listings.
• Budget-Minded Upgrades: Focus on the most visible, high-impact upgrades; look for deals (Wayfair, Amazon, Home Goods).
• Stay Encouraged: The market is tough, but incremental, creative tweaks can make a dramatic difference.
  • "Don’t despair. There is advice out there that doesn’t require you to spend $200,000..." (David, 28:13)
• Get Help: Angela and David offer affordable design and management services, plus ongoing free insight via their podcast and associated masterminds.

Notable Quotes & Memorable Moments

• "You don't have to spend $100,000 and replace everything at once... you can do it and get the biggest bang for your buck." — Angela (01:16)

• "The money that you got from phase one can fund phase two. Now you've got phase two. Now your ADR goes up, your occupancy goes up. Now you've got even more money..." — David (03:18)

• "But obviously, 13 grand is not good. That's a result of having old pictures that were terrible and deferred maintenance that we had to deal with." — David (06:13)

• "23% occupancy increase... We doubled our revenue and increased occupancy by 23%." — Angela (07:44)

• "The first picture is supposed to make them want more. So what can you do that's different but still appealing?" — David (15:38)

• "Every cabin is going to be different... don't put a cookie-cutter approach to every single property." — Angela (12:56)

• "If you're not committed to this, your competition is... If you're not doing that, you're just falling behind." — David (25:16)

• "It looked like the other ones—the same... so there are a lot of things I would have done different." — Angela (26:50)

• "You need a little bit of pop tart in your life if you want to get those bookings." — David (28:56)

Timestamps for Key Segments

• 01:15 – Angela on incremental upgrades and prioritizing ROI
• 02:30 – David breaks down upgrade tiers and phased investment
• 05:55 – Financial before/after: 7-month revenue swing, effect of new photos
• 07:06 – Angela shares occupancy and revenue improvement stats
• 08:39 – Impact of photos/amenities on length of stay
• 09:31 – Pricing strategy and revenue optimization cycle
• 11:35 – Angela on studying the competition and guest "avatar"
• 13:56 – Personalizing each property, finding unique selling points
• 15:38 – Analysis of photography trends and “hero shot” tactics
• 19:47 – Overview of pricing tool strategies and the hybrid/hands-on approach
• 21:05 – Importance of adjusting minimum stay requirements
• 23:03 – Angela on day-to-day management and event-based adjustments
• 25:56 – Angela’s story of buying in a “hot” but competitive market, lessons learned
• 27:17 – David & Angela on breaking (but not shattering) the mold, keeping upgrades budget-friendly
• 28:56 – Memorable “pop tart” quote: standing out versus blending in

Contact Info & Community

• STR design/management help: Angela at info@coasttocoastgetaways.com
• Direct Booking & David's Masterminds: Coast to Coast Getaways, David’s Instagram [@davidgreene24]
• Deals for Podcast Listeners: Mention you’re a subscriber for special offers

This episode provides a rare, unfiltered look behind the scenes of short-term rental transformation—with granular tactics, strategic insights, and a heavy dose of encouragement for any STR operator aiming to stand out without overspending.