Real Estate Rookie Podcast — Episode Summary

Episode Title: How to Fix Low Cash Flow and a “Slow” Agent (Rookie Reply)
Hosts: Ashley Kehr & Tony J Robinson
Date: August 29, 2025

Overview

This "Rookie Reply" episode features hosts Ashley Kehr and Tony J Robinson tackling real investor questions at various experience levels:

• How to handle an unresponsive real estate agent
• The realities and strategies of starting a wholesaling business as a college student
• Troubleshooting disappointing cash flow from a sizable rental portfolio

The tone is friendly, practical, and honest, focusing on actionable advice for real estate “rookies” aiming for their first deals or a modest portfolio—not those chasing a vast empire.

Key Discussion Points & Insights

1. Dealing with a Slow or Unresponsive Real Estate Agent

[00:45–08:12]

Situation:

A new investor is frustrated with an agent who repeatedly submits offers too late, missing out on deals. They’ve already signed a buyer’s agent agreement.

Host Insights:

• Check the Contract:

  • Many new NAR (National Association of Realtors) requirements force buyers to sign exclusivity documents.
  • Contracts may be exclusive or non-exclusive, and may have clear cancellation terms.
  • Tony:

    “Go back and review your contract and try and get an understanding of is it exclusive or is it non exclusive? … In order for me to cancel this, all I have to do is give them written notice.” (04:16)

• Communication First:

  • Discuss expectations openly.
  • Sometimes a frank conversation leads to improved service.
  • Tony:

    “Like, hey, here are my expectations. Here, here's where you're at. How can we, how can we bridge that gap?” (06:21)

  • Ashley:

    “Have you, you know, at least communicated to her that … you would like offers put in same day and if she's too busy, could you refer you to somebody else?” (05:20)

• Work with the Brokerage:

  • Agreements are typically with the brokerage, not just the individual. Ask to work with another agent within the same firm if you’re dissatisfied.
  • Ashley:

    “You need to maybe even talk to the broker of the firm that she works at … Maybe they have another agent within house, they can just transfer that.” (05:20)

• Embrace Tough Conversations:

  • Real estate investing requires assertiveness and dealing directly with problems.
  • Tony recommends reading Crucial Conversations to get comfortable with tough discussions:

    “You got to get comfortable with being uncomfortable in those tough conversations. Otherwise you’re going to be the one that loses almost every single time.” (06:21)

Memorable Moment:

Tony’s story about his first out-of-town agent and how honest feedback changed the dynamic (06:21).

2. Starting a Wholesaling Business in College

[10:13–18:10]

Situation:

A college sophomore wants to buy a first rental before year’s end; has $10K saved, some experience, aims to start wholesaling to build capital and skills.

Host Insights:

• Wholesaling 101:

  • Tony explains:

    “The basic idea of wholesaling is that you are selling contracts for real estate … I get to keep that spread of $20,000 for selling Ashley the rights to that contract. I get paid on the day of closing.” (12:17)

  • States increasingly regulate wholesaling; check if a license is required locally.

• What It Really Involves:

  • Wholesaling can be time-heavy or money-heavy.
  • Time: Knocking doors, cold calls, networking (may take months for first deal).
  • Money: Buying lists, skip tracing, direct mail, AI tools.
  • Ashley:

    “Wholesaling … can be easy if the deals fall in your lap and you have buyers lined up. But this is a very, very active business. … It was one year before [James Dainard] got a deal.” (14:36)

• Building Buyers Lists:

  • Don’t neglect the need for a robust buyer pool to actually close wholesale deals.

• Alternative Strategies:

  • House hacking with low money down (FHA loan + seller credits).
  • Becoming a real estate agent to access deals and commissions.

• Balanced Expectations:

  • Ambition is great, but getting a first deal may take longer than expected.
  • Tony notes students can be “overzealous,” while older investors risk “analysis paralysis”—aim for the healthy middle.
  • Tony:

    “I love the hustle, I just want to make sure we’ve got good expectations here.” (18:10)

Memorable Moment:

Ashley praises using new AI tools in wholesaling—helpful for introverts who hate answering the phone! (14:36)

3. Portfolio Cash Flow Frustration & Next Steps

[23:08–31:55]

Situation:

An investor with 12 properties (23 units, $4.2M value, 33% LTV) sees only $7K/mo in cash flow (not the $12K projected).

Host Insights:

• Analyze Expenses Line-by-Line:

  • Compare actual vs expected costs, including property management, utilities, repairs.
  • Review insurance coverage/rates, property taxes, and any recurring overages.
  • Ashley:

    “I would be interested to see his, you know, what the cash on cash return is for these properties and see what that actually comes out to besides just the cash flow.” (25:05) “If he is the manager or if he has a property manager … has he sat down and actually gone through line item by line item?” (25:05)

• Maximize Income:

  • Check if rents are at or near market rates; use BiggerPockets or similar estimators.
  • Consider rent increases where justified.

• Evaluate Asset Performance:

  • Sell underperforming properties or those with disproportionate equity-to-cash-flow ratios.
  • Utilize a 1031 exchange to redeploy equity tax efficiently.
  • Tony:

    “There’s nothing wrong with getting rid of a property that isn’t serving its purpose anymore … Could you sell that property and redeploy that elsewhere?” (28:02)

• Consider Strategy Shifts:

  • Explore converting units to mid-term or short-term rentals for higher cash flow where feasible.
  • Ashley:

    “Is there an opportunity to turn some of the units into a midterm rental or a short term rental? Oftentimes that can generate more cash flow.” (29:51)

• Reality Check:

  • Some variance between projected/actual cash flow is normal due to vacancies and repairs.
  • Tony:

    “I don’t know if you’ll ever get to the 12k because vacancies and maintenance repair are going to happen. So we underwrite them into our deal.” (28:02)

Memorable (and humorous) Moment:

Tony tells the story of FedEx’s founder winning at Vegas to save his company—then jokes about putting all your rental equity on black if you’re feeling bold! (30:26)

Notable Quotes & Moments

| Timestamp | Speaker | Quote | |-----------|---------|-------| | 04:16 | Tony | “Go back and review your contract … is it exclusive or is it non exclusive? In order for me to cancel this, all I have to do is give them written notice …” | | 06:21 | Tony | “You got to get comfortable with being uncomfortable in those tough conversations. Otherwise you’re going to be the one that loses almost every single time.” | | 14:36 | Ashley | “Wholesaling … can be easy if the deals fall in your lap and you have buyers lined up. But this is a very, very active business. … It was one year before [James Dainard] got a deal.” | | 18:10 | Tony | “I love the hustle, I just want to make sure we’ve got good expectations here.” | | 25:05 | Ashley | “If he is the manager or if he has a property manager … has he sat down and actually gone through line item by line item?” | | 28:02 | Tony | “There’s nothing wrong with getting rid of a property that isn’t serving its purpose anymore … Could you sell that property and redeploy that elsewhere?” | | 30:26 | Tony | “If you really just want to, you know, get spicy with it, just take all that equity, go to Vegas, throw it on black and see what happens.” |

Timestamps for Important Segments

• 00:45 — Frustrations with a Sluggish Agent
• 04:16 — Understanding Contracts, Exclusivity, and Escaping
• 06:21 — Communication & Embracing Tough Conversations
• 10:13 — College Student Starting in Wholesaling
• 12:17 — What is Wholesaling?
• 14:36 — The Realities of Wholesaling & Alternatives
• 18:10 — Managing Expectations as a Rookie
• 23:08 — Troubleshooting Portfolio Cash Flow
• 25:05 — Deep Dive on Expenses, Asset Management
• 28:02 — Disposing of Underperforming Properties & 1031 Exchanges
• 29:51 — Pivot to Mid-term/Short-term Rentals
• 30:26 — The FedEx-Vegas ‘All on Black’ Story

Conclusion

This episode emphasizes due diligence, clear communication, managing expectations, and smart, data-driven decision making across different real estate career stages. The advice is pragmatic, empathetic, and realistic, urging rookies to act but also to analyze and adapt as circumstances evolve.

For practical, actionable tips and relatable real-life stories, this episode is a must-listen for aspiring investors at every stage of their journey.