The David Greene Show – Episode 89: “Seeing Greene with Jake Henderson”
Date: October 17, 2025
Host: David Greene
Guest: Jake Henderson, At Home Wichita Real Estate, Wichita, Kansas
Episode Overview
This “Seeing Greene” episode dives into the state of the real estate market in mid-2025, with an emphasis on navigating industry challenges, market psychology, lending hurdles, and boots-on-the-ground advice. David is joined by Jake Henderson, a Wichita agent and investor, for a candid Q&A session from audience submissions, market commentary, and unfiltered stories from both hosts’ real estate journeys. The show avoids quick-fix advice and instead emphasizes authenticity, transparency, and sustained learning.
Key Theme:
Unfiltered real estate discussion on market dynamics, professional conduct, and practical investment strategies—learning through real-world stories (failures and all), with actionable tips for both investors and agents.
Episode Breakdown
1. Meet the Guest & Setting the Stage
[00:00–02:16]
- David introduces Jake Henderson—an investor-turned-agent with 7 years in Wichita, Kansas.
- Quote (David): “I met Jake when he had me come speak to his meetup … We were just sitting here talking before the recording about how difficult it is to get a good speaker to speak at a meetup … It is not hard to find a real estate podcast or YouTube channel … But not everybody has something good to say.” [00:17]
- Jake’s path: house hacking > getting licensed > loving the business.
2. State of the Market: Local vs. National Shifts
[03:58–05:52]
- David’s personal/portfolio contrast: physical injury vs. sudden bookings and deals after a long dry spell.
- Market insight: Effects of recent Fed announcements, public perception of mortgage rates, and psychological shifts bringing buyers off the sidelines.
- Quote (Jake): “I think the overall general population doesn’t understand how mortgage rates work. So they hear [the Fed news] and they automatically think mortgage interest is down, so they’re back in the market or they’re more motivated.” [05:03]
3. Airbnb, Short-Term Rental Chaos, and Property Management Challenges
[06:23–11:37]
- David shares a saga: properties stolen, forced 1031, trusting management with overly optimistic pro formas, discovering theft, firing managers, launching his own in-house property management in the Smokies.
- Quote (David): “They’re stealing your money. They’re overcharging you for maintenance. They’re using the cabins themselves … There’s like a jealousy issue that’s going on … Slapped me with the lawsuit for breach of contract … I gotta hire staff, and we gotta start learning that market and how to manage them.” [06:45–08:23]
Takeaway
- Turnaround comes from hands-on management and relentless process improvement, not “magic” upgrades or spending massive sums on interior design.
- Market pulse: Spring and summer bring activity upticks likely due to news cycles and consumer psychology more than hard rate changes.
4. How to Write Winning Offers in a Slow Market
[11:37–14:49]
- Buyer opportunities: slow markets = power to negotiate
- Clean offers (few contingencies) get more traction.
- Quote (Jake): “Making an offer that is clean—not many contingencies—you’re more likely to get a lower offer accepted …” [12:59]
- Two-offer strategy: (1) discounted price (as-is, quick close), or (2) creative/owner finance terms.
Communication Best Practices
- Always call, don’t just text or email, to keep negotiations human and tone positive.
- Quote (David): “When I notice when you text, there is a very easy opportunity for tone to be misinterpreted … I would 100% call.” [14:56]
- Remove ego, use humility scripts, and avoid insulting sellers—keep deals alive and emotions out.
5. Navigating Agent Egos and Finding the Right Representation
[18:22–22:21]
- The ego trap: markets cycle, agents often ride the high, but many fumble in downturns.
- Experience matters, but hunger and communication trump tenure.
- Quote (Jake): “Text messages do not have eyebrows … It’s an asynchronous form of communication.” [18:37]
- Strategy: agents (and investors) should ask direct questions, listen more, and understand the seller’s motivation.
- Relevant Story: Jake scores intel for his client—gets the bottom price on a duplex via one phone call, outpacing buyers relying on listed data. [19:50]
6. Listener Q&A and Practical Advice
a) Sparking Interest in Real Estate for Others
[25:31–27:48]
- Best approach: Be the example, involve others, and let them learn by osmosis or low-risk content like YouTube/podcasts.
- Quote (Jake): “The best way is to do it yourself and show them the results, help involve them on some of the process, maybe ask them even if it was as simple as … what paint color.” [25:55]
b) Should You Buy Down the Mortgage Rate?
[29:13–36:41]
- Always do the math: Break-even calculation.
- Quote (David): “You just convert it into money and then let the answers do the talking for you.” [30:18]
- Consider how long you’ll hold/refi; only pay points if you’ll save more (and not refi soon).
- Jake: “How long are you going to hold it? Are you going to keep the same loan for that time?” [29:51]
- David (PSA): Beware headline-grabbing rate “offers”; often require massive points and hidden closing costs.
c) Small/Mixed-Use Lending Challenges
[37:54–46:53]
- Small, mixed-use, or cheap properties are risky to lenders—higher rates or denied financing.
- David: “If you’re starting with the deal that very few people want because it’s easier for you to get in … you’re going to get a hard time getting support.”
- Solution: Build banking relationships, try local credit unions, and use seller financing as a stepping stone.
7. Lightning Round: Hot Takes and Viral Topics
a) The Dave Ramsey Debate
[48:13–53:48]
- Dave Ramsey is not for real estate investors but is great for fiscal discipline for “most people.”
- Jake: “He has a place, but not in the real estate investing space.” [48:43]
- David: “If you just suck with money, I would tell everybody to listen to him. … But if you’re intentionally trying to build wealth, Dave’s not the guy.” [48:43]
b) Transparency About Bad Deals
[54:49–59:23]
- Listeners appreciate honest stories of what goes wrong—and learning from others’ mistakes.
- Jake: “It’s better to be real with education than to fluff it up and make it seem like rainbows and unicorns.” [55:32]
c) Foreign and Institutional Investors
[60:16–63:55]
- Are Blackstone & Co. ruining things? Not as much in Midwest, but they do impact affordability and competitiveness in some markets.
- Jake: “If you’re local to your market … you can outperform institutional investors all day, every day.” [60:16]
8. Real News – Market Trends & Airbnb Nightmare
[63:55–76:29]
a) Summer Inventory and Market Dependability
- National inventory up, sales down, but Midwest (like Wichita) still sees quick sells (median 9 DOM).
- Quote (Jake): “The Midwest is slow and steady.” [63:55]
b) Airbnb Host Damage Saga
- A host suffers $3,000+ in damages—exposes difficulties with Airbnb guest leverage and policy changes favoring guests, not owners.
- David: “Airbnb has made several policy changes grossly favoring tenants … So you are pot committed to this thing … and the guests are coming in … asking for really low prices.” [68:41–73:05]
Actionable Takeaways for Short-Term Rental Owners
- Provide excellent service but be vigilant—platform policies may hinder your protections.
- Building direct-booking channels or niche communities (with clear accountability) may be the future.
9. Featured Property – Panama City Beach Condo
[81:38–85:13]
- Showcases a client-owned, newly renovated beach condo managed by David's company. Listeners get a discount for booking direct.
10. ON LOCATION: Bear in the Truck – Real-Life Property Management in the Smokies
[85:50–91:09]
- David narrates a recent bear encounter at his mountain cabin—a humorous but real risk of managing properties in nature.
- Quote (David): “These bears have learned, like velociraptors in Jurassic park, to open car doors that are not locked.” [88:36]
Notable Quotes & Memorable Moments
-
On market cycles and ego (David):
“There is a lot of that with real estate agents … There’s a lot of ego. Way, way too much of it. … We have done this to ourselves.” [16:48] -
On learning from real experience (Jake):
“It’s way cheaper to learn from David’s mistakes than it is to try yourself and make the same mistake.” [58:51] -
On short-term rental realities (David):
“Airbnb is taking 15.5% now just to put a guest there and they’re offering me no services ... They’re basically charging me property management fees to put a tenant there, then I got to go pay someone to manage the property. It’s stupid when you look at it, but there isn’t anywhere else to go.” [77:00] -
On picking an agent (Jake):
“I call … before we even make an offer and just pick their brain … And I just shut up and listen while I’m on the phone call, not a text message.” [18:37]
Key Timestamps
- 00:17 – Problems with real estate event speakers and influencer noise
- 05:03 – Buyer uptick tied to Fed news
- 06:45–11:37 – David’s nightmare with property management theft in the Smokies
- 12:59 – Making clean, low offers
- 18:37–20:37 – Agent communication and negotiation strategies
- 25:55 – Getting others (like family) into real estate
- 29:13 – Math of buying down a mortgage rate
- 37:54 – Lending frustrations with small/mixed-use properties
- 48:13 – Dave Ramsey: Good for discipline, not for real estate investing
- 54:49 – Should real estate educators share hardship? Yes!
- 60:16 – Institutional/foreign investors, local investors’ edge
- 63:55 – “Cruel Summer”: Real estate inventory trends
- 68:41–73:05 – Airbnb host’s damage claim and issues with platform changes
- 85:50 – David’s bear-in-the-truck adventure
Episode Tone & Style
- Tone: Honest, conversational, humorous, occasionally irreverent but always educational.
- Style: Real-world anecdotes, mathematical walkthroughs, industry insider detail, and “no BS” candor.
Final Thoughts
This episode equips real estate enthusiasts—investors and agents alike—with realistic perspectives for today’s market: negotiation nuances, lending roadblocks, pitfalls of short-term rentals in 2025, and the importance of learning from hard lessons. It reinforces the value of candor, communication, and knowing that “shiny object” content is no substitute for resilient, on-the-ground investing.
For more resources, questions, or to connect with either David or Jake, visit their websites or DM them—both hosts encourage honest dialogue and further discussion.