Real Estate Rookie (BiggerPockets)

Episode: "We’re in a 'Buyer’s Market'…But Where Are the Real Estate Deals?"

Date: November 21, 2025
Hosts: Ashley Kehr & Tony J. Robinson

Episode Overview

In this Rookie Reply episode, Ashley and Tony address common questions beginner real estate investors are facing in the late 2025 market. Key topics include how to find deals in today’s buyer’s market, strategies for off-market and on-market properties, when (if ever) it makes sense to buy a property with negative cash flow, and the metrics and mindset that separate good investments from bad ones. Both hosts share real-world examples and their personal criteria for choosing deals, focusing on actionable advice tailored for those seeking their first few properties.

Key Discussion Points & Insights

1. Struggling to Find Deals in a 'Buyer's Market'

(00:30–08:30)

Cold Calling & Driving for Dollars—Are You Putting in Enough Effort?

• Tony stresses the importance of scale and persistence with outreach strategies.
  • Quote: "Did you call 100 people or did you call 10,000 people? Did you drive for 2 hours or 200 hours? Rookie investors underestimate how much time it takes to really build that pipeline." (Tony, 01:19)
• Cold calling effectiveness is not just about volume, but technique.
  • Crafting and testing scripts is crucial; don't just "wing it."
  • Quote: "Have you trained yourself up on best practices when it comes to sales? Or are you just kind of winging it every time you hop on the phone with someone?" (Tony, 02:02)
• With driving for dollars, target distressed, not well-kept, properties.

On-Market (MLS) Opportunities

• Ashley points out that more properties are sitting longer on the MLS than recent years, creating leverage for buyers.
  • Quote: "I look to pull up Zillow, sort everything by most recent, and then go to the very end of the list and see what's been sitting." (Ashley, 04:09)
• Look for properties with flexible sellers (e.g., no/little debt, long time on market), and consider making lowball offers.

Building 'Seller Lists' and Word of Mouth

• Ashley details recent success targeting properties owned by seniors moving into assisted living/nursing homes.
  • Quote: "In the last two years, four or five of the houses that I have bought have been from somebody that passed away or moved out to assisted living." (Ashley, 05:06)
• Narrow your criteria: focus on a specific type of seller, such as absentee owners, probate, or pre-foreclosure, to use your time and money efficiently.

If Direct Outreach Isn't Working—Leverage Others

• Tony suggests partnering with wholesalers and networking at local meetups.
  • Quote: "Maybe you're just not good at cold calling...focus on networking with the people who are good at that." (Tony, 06:59)
• Example: Investors who source most deals from wholesalers or agents with pocket listings.

2. Should You Buy a Property with Negative Cash Flow?

(10:36–15:54)

Analyzing the 'Negative Cash Flow' Scenario

• A listener ('Vin') asks if buying a negative cash-flowing property makes sense if the rent somewhat offsets their own residence’s mortgage.
• Tony breaks down why this logic is flawed:
  • You still lose money each month; the bigger question is your true financial goal.
  • Quote: "Even if they're making money on this investment property, they're still losing money at the end of the day." (Tony, 11:13)
• Valid exceptions:
  • Your motivation is long-term appreciation (especially in hot markets like the Bay Area).
  • You have strong active income and can easily cover losses.

Risks & Nuances

• Ashley elaborates on betting on appreciation, a strategy some successful investors use.
  • Quote: "They are banking on appreciation...in several years...they’ll be able to sell the property, recoup all of that money...plus make a bigger return." (Ashley, 13:58)
• Consider the true monthly cost, including maintenance, vacancies, capital improvements—not just mortgage shortfall.
  • Power tip: Always run these scenarios through a comprehensive deal calculator.

3. What Separates Good Investments from Bad Ones—And What Should New Investors Know?

(18:28–25:01)

Key Metrics and Decision-Making Frameworks

• Ashley asks Tony to summarize his core investment criteria:
  • "Cash flow, tax benefits, appreciation." (Tony, 20:07)
• Ashley adds a fourth: time commitment (how much hands-on management the property will require).
  • Quote: "I'm definitely will take a little bit less cash flow if I can be more hands off on the property." (Ashley, 21:36)
• Importance of opportunity cost: Could capital be better spent elsewhere, such as hiring help or growing another part of your business?

Handling Stress & Financial Risk

• Ashley: Avoid deals that would stretch you financially or cause undue stress—even if the theoretical returns look great.
  • Quote: "I don't like to take risk financially and stretch myself, because it stresses me out." (Ashley, 23:37)

Must-Have Foundational Knowledge for New Investors

• Tony breaks down key skill buckets:
  • Acquisition: Identifying markets, getting financing, sourcing deals.
  • Execution: Running numbers, negotiating/contract process, due diligence.
  • Management/Rehab: Handling repairs, tenants, or renovations post-purchase.
  • Quote: "Have some sort of working knowledge in all of those big buckets...to give you the confidence to step out and take that first step." (Tony, 24:17)

Notable Quotes & Memorable Moments (with Timestamps)

| Timestamp | Speaker | Quote | |------------|---------|-------------------------------------------------------------------------------------------------------------------------| | 01:19 | Tony | "Rookie investors underestimate how much time it takes to really build that pipeline." | | 04:09 | Ashley | “I look to pull up Zillow, sort everything by most recent, and then go to the very end of the list and see what's sitting.” | | 05:06 | Ashley | "Four or five of the houses that I have bought have been from somebody that passed away or moved out to assisted living."| | 06:59 | Tony | "Maybe you're just not good at cold calling...focus on networking with the people who are good at that." | | 11:13 | Tony | "Even if they're making money on this investment property, they're still losing money at the end of the day." | | 13:58 | Ashley | "They are banking on appreciation...in several years...they’ll be able to sell the property, recoup all of that money...plus make a bigger return." | | 20:07 | Tony | "My motivations for investing in real estate are in priority right now: cash flow, tax benefits, appreciation." | | 23:37 | Ashley | "I don't like to take risk financially and stretch myself, because it stresses me out." | | 24:17 | Tony | "Have some sort of working knowledge in all of those big buckets...to give you the confidence to step out and take that first step." |

Timestamps for Key Segments

• [00:34] – Main episode question: “Having trouble finding deals?”
• [01:17–04:06] – Deep dive: How much effort is enough with cold calling and driving for dollars?
• [04:06–06:58] – On-market strategies, buyer’s market dynamics, and targeted lead lists
• [06:58–08:30] – Networking with wholesalers/agents as an alternative to direct outreach
• [10:36–15:54] – Is negative cash flow ever okay, and what are the true risks?
• [18:28–20:28] – How to personally define a good vs. bad investment (Ashley & Tony’s criteria)
• [23:54–25:01] – Essential knowledge for rookie investors: acquisition, execution, and management

Closing Takeaways

• Effort and focus win: Finding deals is a function of both volume and skill—track your efforts and refine your strategy continually.
• Broaden your networking: If direct-to-seller isn’t working, plug into local wholesaler or agent networks for more opportunities.
• Be laser clear on your goals: The best investment for you is one that aligns with your financial, lifestyle, and risk tolerance preferences.
• Don’t underestimate true costs: When evaluating deals, zoom out from just the mortgage vs. rent; factor in ALL financial and time commitments.
• Become a student of the process: Know at least the basics of acquisition, negotiation, and management to confidently take your first steps.

For rookies with questions about finding deals or evaluating investments in an uncertain market, this episode offers a grounded, realistic, and encouraging roadmap.