773 episodes
- Every rookie thinks their first deal will go according to plan (it almost never does). Today, we’re bringing on a guest who had a long list of all the worst-case scenarios that happened to him, and still walked away winning (to the tune of $60,000!). He’s walking us through it all, so you can master your first deal, too!
Welcome back to another episode of the Real Estate Rookie Podcast! This week, we’re sitting down with Caleb Smith, a real estate agent who bought his first rental at 21 with next to nothing in the bank, and then watched two very different deals go sideways in two very different ways! One taught him an expensive lesson about lenders. The other got hit by a zoning surprise nobody could have predicted, and forced him to pivot on the spot.
Getting your numbers right isn't always enough. Sometimes the thing that changes everything isn't the market, the property, or the strategy—it's something buried in a permit office you never saw coming!
If you're trying to figure out how to get your first deal done with limited capital, wondering what can quietly derail your plan, or just want to hear how a rookie handles it when things don't go the way he expected—today’s episode has real numbers, real setbacks, and a few hard-won lessons worth taking with you into your next deal!
In This Episode We Cover
How Caleb bought his first rental at 21 with only $2,000 to his name
Pivoting to a live-in flip strategy (and the huge benefits of doing so!)
How to knock on doors to find off-market investment properties
Turning a seller credit into an interest rate buydown
The $10,000 origination fee mistake that taught him to shop lenders
Surviving a falling chimney, botched kitchen, and a zoning reversal mid-deal!
And So Much More!
Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-764.
Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email advertise@biggerpockets.com.
Learn more about your ad choices. Visit megaphone.fm/adchoices - Don’t feel ready to buy your first rental property yet? Maybe you just need a better game plan. Today, we’re covering three different but common situations rookies find themselves in leading up to that first deal. Whether you need a few actionable first steps or an extra push, we’ll show you how to get started as soon as possible!
Welcome back to another Rookie Reply! This week, we’re tackling three questions from rookies who all have the same underlying worry: they don’t feel ready to invest in real estate. First up, we’ll hear from a college student with one year left to figure out financing, savings, and education before he buys. Someone else is thinking about long-distance investing and building his team, and finally, a listener with some money saved wants to take the next step toward building his real estate portfolio. The catch? He lives in one of the most expensive markets in the country.
We’re breaking down all the possible solutions, including house hacking strategies, how to think about FHA and conventional financing, why cash reserves matter—even on a primary residence—and the remote management tools that make investing from anywhere possible!
Looking to invest? Need answers? Ask your question here!
In This Episode We Cover
How to prepare to buy your first rental property (step by step)
The software stack that makes remote property management (much) easier
Creative ways to start building a rental portfolio in an expensive high-cost market
How to invest in real estate from long distance (or even overseas)
Why you should always have cash reserves (for each property!)
And So Much More!
Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-763.
Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email advertise@biggerpockets.com.
Learn more about your ad choices. Visit megaphone.fm/adchoices - For years, rookies have heard the same bad news: starter homes are disappearing, and first-time buyers are getting older. But the newest data shows something very different, and we’re breaking down how these recent changes can help you buy your first or next rental property in 2026!
Welcome back to the Real Estate Rookie podcast! Nationally, fewer than four in 10 non-homeowner households can afford a typical starter home. But in some states, things are getting a little easier. We’re breaking down where this market opening exists, where the headlines can be misleading, and how to turn a smaller new construction home or an overlooked resale home into a profitable investment property.
We’re also sharing our own starter home stories, the difference between an affordable home and a “cheap” one, and a five-part screening checklist that will help you separate the two before making an offer. Whether you’re looking to buy a house or find a more affordable real estate market to invest in, stay tuned to learn exactly how to spot a smart next deal!
In This Episode We Cover
What a starter home really looks like in today's market
Which real estate markets have the most affordable starter homes for sale
The critical difference between an affordable and “cheap” rental property
How to take advantage of builder incentives on new construction homes
Why "mom and pop" resale homes are some of the best real estate deals in 2026
And So Much More!
Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-762.
Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email advertise@biggerpockets.com.
Learn more about your ad choices. Visit megaphone.fm/adchoices - What if the biggest obstacle to building wealth wasn't your income, your time, or even your circumstances, but simply believing it was possible for someone like you? Today’s guest made the decision that her past won’t be her children’s future. Real estate made that choice possible!
Welcome back to the Real Estate Rookie podcast! Angela Wassom is proof that real estate really can be for anyone that puts their mind to it. While working full-time and raising seven kids, she's built a 20-unit portfolio across four states—starting with a rental she was genuinely afraid to take on. Angela breaks down how she built a team in markets she'd never set foot in, spotted a listing mistake that turned into a five-figure win, and used one financing strategy to fund nearly every deal since!
She also shares the story of a lender who finally said yes after everyone else said no, and the tenant placement that brought her whole journey full circle. By the end of this episode, you'll see exactly how much is possible with the time and resources you already have!
In This Episode We Cover
How growing up in HUD housing shaped Angela’s mindset of becoming a landlord
Building a remote investing team in markets you’ll never set foot in
The MLS listing mistake that turned into a $10,000 repair windfall
How a HELOC strategy has funded nearly every deal for Angela
Why every lender said no to Angela’s newest short-term rental, until one didn't (and why it was so worth it!)
And So Much More!
Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-761.
Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email advertise@biggerpockets.com.
Learn more about your ad choices. Visit megaphone.fm/adchoices - Feel like your situation doesn't fit the typical real estate investing playbook? Maybe you’re low on cash, your circumstances are unusual, or your timeline feels tighter than everyone else's. You're not alone, and today's episode proves it. But thankfully, we’ve got answers!
Welcome to another Rookie Reply! We’re back with three questions from the BiggerPockets Forums, the first of which comes from a rookie who has very little money saved: Can you buy a rental property with just $5,000? We’ll share some creative ways to get started with low money down!
Next, we’ll hear from someone who wants to invest in U.S. real estate from another country, pointing them to the tools and resources they’ll need to invest remotely. Finally, is it ever too late to start investing? Maybe you’re already eyeing retirement and wondering if rental properties can even fit into your overall strategy. Stick around until the end to find out!
Looking to invest? Need answers? Ask your question here!
In This Episode We Cover
A decade-long plan for late starters looking to retire with real estate
How to turn your primary residence into an entire real estate portfolio
Using creative financing (like seller financing) without taking on extra risk
Why you need cash reserves with every real estate deal
How to build your own real estate team when investing remotely
And So Much More!
Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-760.
Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email advertise@biggerpockets.com.
Learn more about your ad choices. Visit megaphone.fm/adchoices
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About Real Estate Rookie
New to real estate investing and not sure where to start? Ashley Kehr and Tony J. Robinson break down the basics with real-world deal analysis, investor interviews and listener Q&A.
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