The David Greene Show | Episode 99: The Slow and Steady Investing Process

Date: November 20, 2025
Host: David Greene
Guests: David and Morgan Stanhope

Episode Overview

This episode of "The David Greene Show" dives into a contrarian approach to real estate investing: building wealth slowly and sensibly while maintaining a W2 career. Host David Greene interviews David and Morgan Stanhope, a New York-based couple who built an impressive portfolio of sober living homes in Florida—all without leaving their day jobs. Their journey challenges the prevailing fire-and-quit mindset and offers practical, honest advice for long-term wealth builders.

Key Discussion Points & Insights

1. Challenging the Quit-Your-Job Narrative

• [00:19]–[02:37] The Stanhopes and David Greene openly question the increasingly popular advice to quit your W2 once you start investing. Instead, they advocate stability, long-term security, and leveraging your job for growth.
  • "We don't think that quitting your W2 is the best move for every single person and even the best reason to get into investing in real estate." — David Greene [00:19]
• Discussion includes the unglamorous but crucial role of good communication and trust between spouses investing together.

2. COVID Beginnings and First Deal Dynamics

• [02:37]–[07:14] The Stanhopes got started at the heart of the pandemic—against prevailing negative news and advice. They saw opportunity amid chaos, educated themselves primarily through free podcasts, and leaned into their respective strengths.
• [04:04]–[06:06] They describe their first deal: buying sight-unseen in Cape Coral, Florida, via the '1% Rule.' They pivoted to focus on sober living homes, a niche that would set their portfolio apart.

3. Learning Together: The Podcast & Book Education Approach

• [07:14]–[16:51] David and Morgan detail how they split research tasks around work, parenting, and chores.
  • "Every free moment we had... we knew that we had a goal. And there’s all this free information." — Morgan [15:53]
• They emphasize cost-effective learning and “nerding out” over real estate podcasts and books (Rich Dad, Poor Dad, BiggerPockets, etc.) rather than paying for expensive courses.

4. Partnership, Decision-Making & Managing Doubts

• [10:53]–[12:42] The couple discusses how they blend different visions (boring cash-flow investments vs. shiny vacation rentals), prioritize trust and transparent communication, and mitigate risk together.
  • "If it didn't work out, the worst thing you can do is sell a house." — Morgan [12:17]
• Morgan describes the emotional dynamics of giving up her career to stay home and why real conversations around money and risk are vital.

5. Sober Living Homes: The Winning Niche

• [13:45]–[27:43] The Stanhopes lay out why and how they landed on sober living homes:
  • High demand, strong tenant support networks, and positive societal impact.
  • Choosing locations based on criteria like proximity to bus lines and being in “B” neighborhoods suitable for long-term tenants.
  • The nonprofit partners fill the houses; Stanhopes supply maintenance/upgrades and maintain strong, supportive landlord-tenant relationships.
  • "We always have that mantra—let’s find a home that’s something we would live in." — David S. [21:41]
• Tenant selection: Explained. Nonprofits place tenants and oversee the houses’ internal administration.

6. Scaling Up & Building Systems

• [27:47]–[35:30] After four houses in their first year, their process is highly systematized: they rely on Google, Yelp, referrals, and tenants’ skills for contracting and maintenance.
  • "The amount of education I’m able to do every single week... is a lot." — David S. [13:45]
• The couple leverages technology––from detailed spreadsheets to ChatGPT and U-Haul migration data––to guide decisions and projections.

7. W2 Job Security Versus Real Estate "Hustle"

• [33:36]–[42:15] David and Morgan defend maintaining a W2, even when their real estate income surpasses their salaries. Reasons:
  • Security for family (healthcare, insurance, steady income)
  • Access to financing and easier qualifying for loans
  • The reality that real estate income can be volatile and cyclical
  • "There's something to be said... about having your W2. As long as you don't completely hate it, keep your W2." — David S. [33:42]
• Both agree that quitting just before reaching agency retirement and benefits makes little sense.

8. Lessons from Down Markets and Corrections

• [39:53]–[42:15] David Greene and guests reflect on how high interest rates, a slower market, and tighter liquidity have made real estate less "sexy"—and underscore the importance of steady jobs and patience.
  • "Real estate is a long term game. It's not a get rich quick scheme." — Morgan [41:11]

9. Future Goals & Financing Strategies

• [42:19]–[44:13] Lasered on building toward 50-100 homes, adding states, and funding via a combination of cash flow, W2 income, 401k, and moving to DSCR loans after maxing conventional mortgages.
• [44:13] They rely on personal recommendations, online reviews, and even skilled tenants for property maintenance and upgrades.

10. Practical Tips for New Investors

• [47:28]–[48:55] Advice centers on getting clear on your “why”, self-education, leveraging free resources, and not being lured by shiny get-rich-quick marketing.
  • "If you want something that much, then you'll just do it." — Morgan [47:49]

Notable Quotes & Memorable Moments

• On Buying Their First Property (Risk Perspective)

  "What's the worst that could happen?...A lot of bad things could happen, but...you have similar dynamics now."
  — David S. [04:41]

• On Spousal Teamwork

  "You need to have your spouse on board...to have each other on board."
  — David S. [11:34]

• On Educating Yourself for Free

  "There's all this free information...We literally didn't hardly spend any money."
  — Morgan [15:53]

• On Keeping a W2 Job

  "It just seems silly that he's worked so hard at his job to leave it just because we've been successful in another avenue."
  — Morgan [34:09]

• On the FIRE Movement

  "I'm not a big believer in the fire movement...You can retire at 30 but then you don't realize 10 years later there's inflation, there's family, there's healthcare..."
  — David S. [36:16]

• On Real Estate's Nature

  "Real estate is a long term game. You have to wait the years out to see that financial return."
  — Morgan [41:11]

• On Finding Deals & Neighborhood Research

  "Once I find the house, I’ll go on Google Maps, zoom into the street view…I 'drive' down the road just to see what’s the neighborhood like."
  — David S. [53:52]

• On Regrets

  "My biggest regret is not starting sooner...I try to tell people all the time...just pick up a book, here's free information..."
  — Morgan [49:21]

Timestamps for Major Topics

| Segment | Timestamps | |-----------------------------------|-----------------| | Intro & Meet the Stanhopes | 00:00–02:37 | | Starting in COVID | 02:37–07:14 | | Learning Through Podcasts/Books | 07:14–16:51 | | Couples' Decision Dynamics | 10:53–12:42 | | First Sober Living House | 13:00–23:24 | | Sober Living Strategy Explained | 23:24–29:36 | | Scaling Up/Systems | 29:36–35:30 | | Keeping the W2/Anti-FIRE | 33:36–42:15 | | Navigating Market Corrections | 39:53–42:15 | | Future Goals & Funding | 42:15–44:13 | | Practical Investor Advice | 47:28–48:55 | | Spreadsheets/Data/Tech Tips | 50:08–54:11 | | Cop Life, Mentorship, and Faith | 56:52–67:32 |

Host & Guest Takeaways

• Sticking with a W2 is not “playing it safe”—it’s playing it smart when building generational wealth.
• Leverage every free resource possible before spending on expensive coaching.
• Embrace niches and use systems for scale—do your due diligence, use data, and automate what you can.
• Partnership (especially as a couple) thrives on open discussion, clear roles, and shared vision.
• Slow and steady truly can win the race in real estate.

Connect with the Stanhopes

• Website: Stanhope Capital ([link not provided, see episode])
• Instagram/social handles available via their site

Final Word

“The slow and steady pursuit, like the tortoise...is working out so good for you guys and that you're doing well when there's so many people that are not and don't want to get out there. So this is the anti-fire approach. And you guys are looking pretty smart now.”
— David Greene [67:35]

For aspiring investors or seasoned pros, this episode is a masterclass in cautious optimism, teamwork, and bypassing hype for lasting returns.