Real Estate Rookie Podcast: "Afraid to Buy Your First Rental? Here’s How to Finally Start (Rookie Reply)"

Hosts: Ashley Kehr & Tony J Robinson
Date: October 31, 2025
Podcast: Real Estate Rookie, BiggerPockets

Episode Overview

This "Rookie Reply" episode addresses the classic anxieties and obstacles faced by new real estate investors. Ashley and Tony answer three critical rookie questions:

1. How to take your first steps when you're feeling stuck
2. How to avoid getting overcharged by contractors
3. How to approach a potential multi-unit investment—especially when concerned about personal guarantees

Their focus is on actionable, practical advice for listeners gearing up to buy their first, second, or third property—not those seeking to "10X" their business overnight.

Key Discussion Points & Insights

1. Getting Unstuck and Taking the First Step into Real Estate (00:00–08:47)

Clarify Your "Why" and Your Goal

• Tony: “The first step is just to clarify what is your why and what is your end goal…” (00:57)
• Everyone's motivations and resources are different; tailor your approach accordingly.

Get Specific About Your Strategy and Niche

• Ashley: “People aren't getting niche enough. You might want to quit your job, but what does your desired day-to-day actually look like?” (01:41)
  • “Do you want to retire, or do you want to work for yourself—running short-term rentals, flipping, or managing long-term rentals?”
• Tony: “Even within flipping, there are niches—land, apartments, hotels... figure out not just your strategy but also your niche.” (03:27)

Lean into Your Existing Strengths & Resources

• Ashley: “Take advantage of your current resources—your knowledge, network, or skill sets—to accelerate your success.” (04:38)
  • Example: Her initial property management experience gave her a clear advantage.

Build Your Team Early

• Tony: “A good lender should maybe even come first, before you start focusing on markets or properties, so you know what you can actually afford.” (06:31)
• Agents and lenders are key early relationships—BiggerPockets’ Agent and Lender Finders make this easier.

Embrace Momentum Over Perfection

• Tony: “Inaction has killed more real estate investing dreams than slightly misaligned action…Momentum beats perfection.” (08:02)

Build Confidence Through Small Steps

• Ashley: “Building confidence can be just making those very small moves—networking, deal analysis, shadowing someone, or finding a mentor.” (08:47)

2. How to Know If You're Being Overcharged on a Rehab (11:22–21:57)

Framework for Evaluating Rehab Quotes

• Breakdown of a listener’s Charleston, SC, flip:
  • 900 sf, 2-bed/1-bath, full gut, GC quoting $90k ($100/sf), owner expected $65/sf ($60k).

Item-by-Item Estimation

• Hosts walk through their project cost estimates, including roof, flooring, drywall, electrical, kitchen, bath, etc.
  • Ashley: “For a new roof—about $5,000.” (13:04)
  • Tony: “For flooring, roughly $4,000 for 900 sq ft with LVP.” (13:39)
  • Other items: kitchen ($20k, possibly high), bathroom ($5k), drywall ($10k), electrical ($2k).

Reality Check Against Real-World Projects

• Tony: “Our last flip was about $60/sf. That was in California, which is arguably a high-cost area.” (19:18)
• Ashley: “My last 3-bed, 1-bath flip (bigger and nicer finishes) was $80k all-in—still less than this 2/1 quote.” (18:14)

How to Vet and Validate Contractor Bids

• Get quotes from at least three contractors to test the market.
  • Tony: “If everyone comes back at 90 grand…maybe the market supports it, or maybe not.” (17:06)
• DIY Materials Price Audit Method:
  • Ashley: “Go room by room, list materials, and Google or use Lowe’s to price them… That’s how I learned my numbers.” (19:59)
• Identify material vs. labor costs to see where money is being spent.

Memorable Quote

• Tony: “Even if you’re remote, you can make calls, get rough quotes, and build a budget from afar.” (17:06)

3. Tackling a First Big Multifamily Purchase without a Personal Guarantee (25:13–37:10)

Scenario

A listener found a 10-unit, $550k opportunity, with $100k cash but is reluctant to sign a personal guarantee to protect his home and family.

The Reality of Personal Guarantees

• Ashley: “On almost every loan, whether it’s personally or in an LLC, I’ve been a personal guarantor. It’s way easier to get the loan, and the rates are better.” (26:23)
• Tony: “The only non-recourse loan I’ve done was seller-financed. Seller financing may offer more flexibility around guarantees.” (27:04)

Exploring Non-Recourse Options

• Look into lenders offering non-recourse debt—some exist, even for new LLCs.
  • Tony: “How many lenders have you actually spoken with specifically about non-recourse debt?” (27:11)

Insurance, Structuring, and Spousal Concerns

• Discuss realistic risks—insurance layers, what an LLC protects, and what could trigger personal liability.
  • Ashley: “What is your wife’s worst-case scenario? Is it liability? Foreclosure? Understanding that is key.” (28:20)

The Risk of Personal Guarantees Clarified

• Tony: “If you default as a guarantor, and the property doesn’t cover the debt, the lender could seek a judgment and pursue other assets, but only after foreclosure and legal process.” (32:27)

Making Your Case—Presenting the Numbers

• Ashley: “Create a visual presentation of the risks and reserves. Walk your spouse through worst—and best—cases.” (33:23)

Alternative Solutions

• Tony: “Bring in a partner to sign the loan and offer a slice of equity.”
• Ashley: “Some syndications do just that; they take in key partners whose net worth qualifies them for the loan.” (35:46)

Maybe Start Smaller

• Tony: “Maybe 10 units is too big a first leap. Start with something you could buy and rehab for under $100k—no loans, no guarantees.” (37:10)

Notable Quotes & Memorable Moments

• “Inaction has killed more real estate investing dreams than slightly misaligned action.”
  — Tony (08:02)
• “Momentum beats perfection.”
  — Tony (08:05)
• “Do you want to quit your job to stop working, or do you want to create a job for yourself?”
  — Ashley (01:37)
• “A good lender should maybe even come first…”
  — Tony (06:31)
• “Go room by room, list every single thing and price it out. It’s time-consuming, but that’s how you learn your numbers.”
  — Ashley (19:59)
• “If you default as a guarantor…they could pursue other assets, but only after foreclosure and a judgment—that’s the worst case.”
  — Tony (32:27)
• “Bring in a partner to sign the loan and offer a slice of equity.”
  — Tony (35:09)

Timestamps for Key Segments

• 00:00–08:47: Overcoming analysis paralysis, clarifying your why, and building confidence
• 11:22–21:57: Vetting rehab estimates; strategies for understanding contractor pricing
• 25:13–37:10: Navigating personal guarantees, presenting risk to family, and creative financing/partnerships

Summary Takeaways

• Start with your goals and your resources—don’t force yourself into a strategy just because it seems exciting if it doesn’t leverage your strengths.
• Focus on momentum, not perfection; action—even if imperfect—builds confidence and leads to opportunity.
• When vetting contractor quotes, do your homework: itemize, get competing bids, and understand the local market.
• If worried about personal guarantees, explore seller financing, non-recourse lending, or equity partnerships—and communicate the risk transparently to partners or spouses.
• Consider starting with a smaller deal to build confidence and family buy-in if a large multifamily feels like too big a leap.

Hosts:
Ashley Kehr & Tony J Robinson
Find more at: BiggerPockets Real Estate Rookie Podcast