Real Estate Rookie — How to Find Great Real Estate Deals in 2026 (Before Anyone Else)

Podcast: Real Estate Rookie (BiggerPockets)
Hosts: Ashley Kehr & Tony J Robinson
Episode Date: December 12, 2025

Overview

This “Rookie Reply” episode is designed for new real estate investors wondering how to find and evaluate great deals, whether now is a good time to buy, and the practicalities of managing house flips as a rookie. Hosts Ashley Kehr and Tony J Robinson answer real, granular questions from listeners, sharing actionable advice, rules of thumb, and the mindset shifts needed to grow from your first to your third investment deal.

Key Discussion Points & Insights

1. What Defines a “Good Deal” in Real Estate?

(00:30 - 10:20)

• Personal Goals Shape What’s "Good"

  • Tony stresses that “a good deal to me could be a bad deal to you and vice versa” because every investor’s goals, skills, and resources are different.
  • Quote:

    “We all invest for different reasons. We all invest with different inherent skills and we all invest with different amounts of time, effort, and energy that we're willing to put into real estate.” (01:10, Tony)

• Core Metrics Everyone Should Know

  • Cash Flow: Cold, hard income produced by the property.
  • Cash on Cash Return: How much cash you’re getting back compared to how much you put in.
  • Appreciation/Equity Growth: Long-term property value increase, varies by market.
  • Tony notes that tax benefits exist but may not be a rookie’s primary concern at first.
  • Quote:

    “Cash flow, cash on cash return, and equity growth or appreciation I think are the big things to focus on.” (04:56, Tony)

• Don’t Forget About Regulatory Risks

  • Ashley adds that being able to execute your chosen strategy (e.g., short-term rental) in a particular market long-term is essential given changing regulations.
  • Quote:

    “It would be a good deal if you can actually do that strategy long term...there’s been towns near me where people have short term rentals and all of a sudden the town says...you can’t do short term rentals anymore.” (05:21, Ashley)

• Define Your Own Buy Box

  • Tony recommends investors get hyper-specific about what they’re looking for (price range, size, market type, etc.), making it easier to quickly filter deals.
  • Quote:

    “Once we had that buy box built out it became significantly easier for us to say yes or no to certain deals.” (06:26, Tony)

• Rules of Thumb for Quick Analysis

  • 1% Rule: Monthly rent should be at least 1% of purchase price.
  • 50% Rule: Expenses should not exceed 50% of revenue.
  • These help quickly screen deals before deep analysis.

• Action Beats Perfection

  • Ashley cautions against “analysis paralysis” — your first deal does not have to be perfect; learning is more important.
  • Quote:

    “As long as it ends up being a good deal, it is going to make you so much more money because that first deal propels you, it gives you...it’s going to start your investing journey. So don’t get too caught up in analysis paralysis, thinking you need to find the perfect deal.” (08:09, Ashley)

• Give Yourself Permission to Learn

  • Tony draws an analogy to children learning to walk to encourage patience and persistence in real estate.
  • Quote:

    “If you have a child...chances are that child did not come out of the womb walking...real estate investing...is the same process. The goal is that we can lay a foundation with that first deal — it’s not to be perfect.” (09:05, Tony)

2. Should Rookies Hire a General Contractor (GC) for House Flips?

(12:39 - 20:34)

• Understand Permit/Lender Requirements

  • Ashley explains that, depending on your area and lender requirements, you may have to use licensed professionals for certain tasks (especially plumbing & electrical).
  • Quote:

    “Depending on your city's regulations, you might have to show that it's somebody licensed doing the work...like electrician and plumber, like two big things that usually you would have to show.” (13:53, Ashley)

• Value of a General Contractor — Especially for Newbies

  • Tony says unless cost is an overwhelming issue and you have lots of experience, a GC is beneficial for first flips. They can foresee issues and offer design ideas that rookies might overlook.

  • Quote:

    “Even though you’re not changing the layout, as a rookie investor, sometimes there is value in having an experienced general contractor guide you through on this first project.” (15:32, Tony)

  • Both hosts share stories of GCs suggesting layout improvements and making projects far smoother.

  • Quote:

    “My GC, like, pretty much built the house himself. He was a licensed electrician, a licensed plumber. Like, he was a jack of all trades. And if I could have him do every house that I ever touch, like, I would 100% consistently use him no matter how much he paid.” (16:53, Ashley)

• Consider Getting Licensed Yourself

  • Ashley notes, as an alternative, that an unlicensed partner could pursue a GC license — though the process varies by area.

• Protect Yourself with Payment Structure

  • Tony urges rookies to structure payments to minimize risk: never pay huge deposits upfront, use milestone payments tied to verified progress.
  • Quote:

    “Do not give them a super large deposit upfront...break it out into very clear milestones, and then only issue those payments once you’ve validated that those milestones are done.” (18:36, Tony)

3. Is Now a Good Time to Buy Real Estate?

(24:06 - 28:04)

• Ignore the Timing Fallacy: Start Now

  • Tony states directly: “There is a right time [to invest], and it’s right. Actually, it’s yesterday. Yesterday was the best time to invest in real estate and today’s the second best day.” (24:53, Tony)
  • He cautions against trying to time market crashes, especially if advice is coming from non-practitioners.

• Filter Who You Take Advice From

  • Quote:

    “The majority of the people who are telling you to wait for the market to come down or wait for the market to crash probably haven’t invested in a lot of real estate themselves...I almost never hear that advice from people who are doing this actively every single day.” (25:24, Tony)

  • It’s about time in the market, not timing the market.

• Always Have an Exit Strategy

  • Ashley reminds listeners (with reference to recent guests Thatch Win and James Dainard) that successful long-term investors outlast downturns by ensuring multiple exit strategies — rentals, furnished rentals, planned losses if needed.
  • Quote:

    “If you’re on a shorter term project such as you’re doing a flip, what is your exit strategy to get out of that deal if the market does take a big downturn right when you list it?” (26:42, Ashley)

• Embrace the Ups & Downs — It’s Not a Get-Rich-Quick Scheme

  • Real estate is a long game, not a quick play. Even the pros have bad years, but the long-term upward trend is on their side.

Notable Quotes & Memorable Moments

• “A good deal to me could be a bad deal to you and vice versa.” (01:10, Tony)
• “Give yourself permission to learn...the goal is not to be perfect.” (09:05, Tony)
• “Don’t get too caught up in analysis paralysis thinking you need to find the perfect deal.” (08:09, Ashley)
• “There is a right time [to invest], and it’s right. Actually, it’s yesterday. Yesterday was the best time to invest in real estate and today’s the second best day.” (24:53, Tony)
• “It’s about time in the market, not timing the market.” (25:55, Tony)
• “You have to be prepared to ride the roller coaster and be in this for the long term, for the long play.” (27:10, Ashley)

Timestamps for Key Segments

• 00:30 — First Question: What makes a “good deal”?
• 01:10 — The subjectivity of a “good deal” (Tony)
• 04:56 — The 3 key metrics (cash flow, cash-on-cash, appreciation)
• 05:21 — Regulation risk as part of deal evaluation (Ashley)
• 06:26 — Building and sticking to your buy box (Tony’s example)
• 08:09 — Don’t chase perfection (Ashley)
• 09:05 — Permission to learn vs. analysis paralysis (Tony)
• 12:39 — Second Question: Should a general contractor be hired?
• 13:53 — When permits and licenses are required (Ashley)
• 15:32 — Why a GC is valuable for rookies (Tony)
• 16:53 — The impact of having a great GC (Ashley)
• 18:36 — How to structure payments with contractors (Tony)
• 24:06 — Third Question: Is now a good time to buy?
• 24:53 — The best time to invest is now — or yesterday (Tony)
• 26:42 — Always have an exit strategy (Ashley)
• 27:10 — Real estate = Long-term play (Ashley)

Conclusion

This episode offers foundational advice in a relaxed, relatable way for aspiring and early-stage real estate investors. Key takeaways include the importance of personalizing your investment strategy, the real risk of waiting for "perfect" timing, the value of learning through action, and surrounding yourself with the right professionals (and protecting yourself with the right contracts). Ashley and Tony provide a supportive, actionable roadmap — with plenty of rookie-specific wisdom — to help you confidently embark on your real estate journey.