The David Greene Show: Seeing Greene with Ashley Cole | Episode 101

Real Talk Real Estate - November 26, 2025

Episode Theme:

A Deep Dive Into Modern Real Estate Challenges—House Hacking, Short-Term Rental Headaches, and Market Insights

David Greene hosts with special guest Ashley Cole, an experienced short-term rental investor and property manager. This episode features listener Q&A, rapid-fire reactions to real estate news and social media comments, and sharp discussion of the shifting landscape for short-term rental (STR) owners. David and Ashley candidly tackle the hardest questions about Airbnb’s recent pivot, market regulations, property management, and growing pains for investors.

Meet the Hosts

David Greene
Investor, agent, author, and podcast personality.
Known for pulling back the curtain on real estate realities.

Ashley Cole
Owns 19 STRs and manages over 40 in Branson, MO.
Started with house hacking, now running a diversified real estate business (including a newly acquired 160-acre farm).
Emphasizes humility, hands-on experience, and adaptive strategy.

Notable: “I collect condos. My husband collects cows.” (02:08 - Ashley)

[01:07] Ashley’s Investment Background

• Invests in Branson, MO (19 owned STRs, manages 40+)
• Started in real estate at 21, house hacked 8 properties, transitioned to STRs
• Recently bought a 160-acre farm; plans to lease the house and let her husband run cattle
• Rejects the promotional social style (“I’m so bad at social media…” 02:23) and leans into industry humility

[02:51] Listener Q&A #1: House Hacking for Beginners

Caller: Anthony Wheeler – Aspiring to house hack a duplex for $220k, with plans to rent one side for $1,100–$1,200.

Key Takeaways:

• Ashley: Strong endorsement for house hacking—did it 8 times, started by living with roommates and fixing as she went.
  • Quote: “I think that’s absolutely the right way to go... a great way to get into real estate and grow fast.” [04:07]
  • Trust your roommates, consider DIY renovations, and think BRRRR-method for extra value.
• David: Drive the neighborhoods personally. Beware of low-priced problem properties (avoid long-distance unless experienced).
  • Secure experienced, committed agents (“not someone who sold three houses in their life” 07:59) and focus on seller-paid closing cost credits to minimize out-of-pocket.
  • “I prefer to pay $220 for a house and get $10k back in closing cost credits than pay $210 for that same house.” [08:36]

[09:03] Listener Q&A #2: The Airbnb Crisis

Caller: J.R. Matthews (Boston) – STR owner frustrated with Airbnb’s lack of host support, constant guest complaints, unclear insurance, and searching for alternatives.

Key Takeaways:

1. Ashley’s Host Perspective:

   • Airbnb has changed—used to support hosts, now "a necessary evil."
   • Guests are increasingly gaming systems (e.g., YouTube guides to get refunds; 14:15).
   • Company sides with guests, makes hosts vulnerable, and has shifted from partnership to impersonal marketplace.

2. David’s Experience:

   • Shared story where a guest exaggerated “black mold;” caused $7500 in lost revenue during a 40-day delisting.
   • “If you don’t give me my $2,000, I can hurt you for $7,500 and they have nothing to lose.” [16:35]

3. Industry-Wide Issues:

   • STR market is saturated, guest expectations are up, cleaning labor is expensive.
   • Direct booking is promising but hard; requires strong SEO, marketing, and trust.

4. Emerging Solutions:

   • Wander: STR management innovator, expanding their high-SEO direct booking platform to all operators soon. [21:36]
   • Hosts need to develop their own brand, utilize tech, and connect with guests outside of platforms.

5. Airbnb’s New Fee Structure:

   • Host commission up to 15% from 3%, necessitating an 18.35% price hike to maintain profit (24:20).
   • Company promotes additional upsells (events, services) where hosts take on risk, get no share.

6. Property Management Advice:

   • Consider hiring a manager; it’s a full business, not a passive sideline.
   • “If you don’t have the time and expertise… hire somebody, otherwise you’re leaving money on the table.” [26:51]
   • Vet managers: Do they invest themselves? Do they know the market? Are they prompt, organized, and ethical?

Memorable exchange:
David: “You want property managers that… have learned the hard way and you benefit from that experience.” [34:10]
Ashley: “You get what you pay for. My clients make more, even after my higher fee.” [30:27]

[39:49] Direct Booking: Tips for Consumers

• Ashley: Google destination and look for company names in Airbnb descriptions; find and book direct to avoid fees (36:50).
• David: “If you book direct, I’m more likely to give you a discount—you’re showing trust and can’t leave a bad review to leverage me.” [39:18]
• Booking directly benefits both sides: hosts make more, guests pay less.

[41:57] Hot Takes & Quick Hitters: Social and Listener Reactions

• On Authenticity:

  • Listeners want real stories, not just “rah-rah” hype.
  • Ashley: “If somebody’s just telling me all the good, I’m not going to believe it.” [43:06]

• On ADUs/Non-Vacay Airbnb:

  • Evaluate local demand, zoning, and hotel presence before pursuing.

• On Pricing Tools:

  • Price Labs, Wheelhouse: Essential for maximizing STR revenue—can drastically outperform gut-based pricing.
  • Ashley: “If you aren’t using Price Labs, you’re leaving money on the table.” [49:51]
  • Leverage market dashboards and dynamic pricing, or hire a manager who does.

• Generational Slang Sidebar:

  • David is annoyed by service worker “I got you;” Ashley’s desensitized by her kids’ language (“bro”); illustrates generational culture clash.

[67:56] Real News Report: Market Headlines

Article 1: No Crash, Just Stagnation

• Prices have not crashed despite endless headlines.
• Buyers’ power has increased (listings up 30%), but transactions remain low and prices mostly flat.
• It’s feast or famine: lack of competition discourages buying, but no mass exodus/crash likely.

Article 2: STR Regulations in Austin

• New local ordinances add licensing, spacing rules (1000 feet between STRs, up to 2 per lot).
• Example of regulatory swings impacting investor viability and market sentiment.
• Ashley: “There is so much over-regulation in the short term rental world… it’ll fail or succeed on its own.” [75:26]

Article 3: Miami—is the Bubble Bursting?

• Miami named most vulnerable global real estate bubble (UBS): “epicenter of volatility.”
• Price-to-rent ratio, insurance, fees, and regulation all contributing.
• David: “That’s the girl you want to avoid dating. The epicenter of volatility…” [77:15]
• Ashley’s approach: invest where you know, not just where “everyone else” goes.

[80:14] Featured Property: Adding Value with Design

• Example: Unused yard with ugly concrete hands converted to multi-use firepit and gathering space.
• Ashley and David both stress the importance of strong visual presentation; quality photography is expensive but crucial.

Notable Quotes by Time

• [01:41] David (about Ashley’s success): “She’s so successful that she lost track of how well she’s doing…”
• [07:59] David: “Make sure you get an agent that's not like a friend… you want this to be somebody that knows how transactions work.”
• [14:15] David: “There are videos on TikTok/YouTube literally teaching guests how to get refunds on their Airbnb stay…”
• [24:20] Ashley: “They are shifting all of that now to the hosts. So hosts are now being charged 15%... That’s a huge difference.”
• [26:51] Ashley: “Short term rentals are not passive. They're a business… If you don’t have the time, hire somebody.”
• [30:27] Ashley (about major management firms): “Clients coming from [Evolve/Vacasa] pay a higher fee with me and make way more money.”
• [39:49] David: “If you book direct, I’m more likely to give you a discount… you can’t leave a bad review and hold me hostage.”
• [43:06] Ashley: “If somebody’s just telling me all the good… I’m not going to believe it.”
• [49:51] Ashley: “If you aren’t using Price Labs, you’re leaving money on the table.”
• [75:22] Ashley: “It’ll fail or succeed on its own.”

Tone & Style

Friendly, direct, with candid confessions of mistakes and frustrations. Both hosts take time to crack jokes (“Heifers and HOAs,” “epicenter of volatility,” “green cheese”), poke fun at generational quirks, and encourage real-world humility. The message is clear: Real estate is rewarding but tough—success depends on adaptability, relationships, and the courage to face hard truths.

Actionable Advice You Can Use

• For New Investors: House hacking is a trusted, low-risk entry point. Vet partners and professionals carefully.
• For STR Hosts: Explore direct booking, keep improving systems, and push for tech/managerial leverage.
• For Market Watchers: Don’t hold your breath for a crash but watch local trends and emerging regulations closely.
• For All Investors: Invest in markets you know or can drive to if possible; beware “hot” markets at their peak.
• For Booking Travelers: Always search for direct booking options and read between the lines of listings for deals.

Connect with the Hosts

• Ashley Cole: regastays.com, social: @regastays
• David Greene: davidgreene24.com, social: @davidgreene24
• STR Management/Direct Bookings: coasttocoastgetaways.com

Summary by Segment Timestamps

• [01:07] Ashley’s background
• [02:51] House hacking Q&A
• [09:03] Airbnb horror stories
• [20:35] Alternatives/direct booking
• [24:20] Host fee structure changes
• [26:51] Professional management discussion
• [39:49] Booking tips and host-guest psychology
• [41:57] Reacting to audience comments
• [67:56] Real News segment: markets, regulation, Miami
• [80:14] Before/after featured property
• [82:52] Where to find Ashley/closing info

Endnote:
Share with a friend—especially a struggling STR owner—because “they might not be doing so well right now.” [81:57]

“Get ready to learn, laugh, and level up your real estate game…” — The David Greene Show