5 Things We’d Do If We Were Starting Over in Real Estate Today

Real Estate Rookie

BiggerPockets

Entrepreneurship, Education, Investing, Business, How To

4.7 • 1.8K Ratings

🗓️ 25 February 2026

⏱️ 40 minutes

🔗️ Recording | iTunes | RSS

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Summary

Still stuck on step one in your investing journey? There are countless success stories from investors who started five, 10, or 20 years ago. But getting started in 2026 is a different ballgame. Not to worry—we’re sharing exactly how we’d approach real estate investing if we were starting over today! Welcome back to the Real Estate Rookie podcast! Today, Ashley and Tony own dozens of rentals, but not long ago, they were rookies, too. If they had to go back and build their real estate portfolios from scratch, knowing what they know now, what would they do differently? We’re breaking it all down on today’s episode! Whether you dream of retiring early with real estate or simply owning a rental property or two, this episode is full of helpful tips, tricks, and traps WE wish we knew when starting out. You’ll learn all about setting real estate investing goals, building your buy box, and lining up your financing. We also share why waiting for the home-run deal is actually a trap, while buying the “boring” deals will eventually make you rich! In This Episode We Cover Five things we’d do differently if we were starting over in real estate today Picking the “boring” deal versus waiting for the “home-run” rental The crucial questions YOU must answer before investing in real estate Financial “levers” you can pull to help fund your first real estate deal How to create your buy box and niche down to specific neighborhoods And So Much More! Check out more resources from this show on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠BiggerPockets.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.biggerpockets.com/blog/rookie-684 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

Transcript

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0:00.0	If we were starting over in 2026, we wouldn't be looking for the perfect market, the perfect strategy, or the perfect deal.
0:08.2	We'd be focused on one thing, making the decisions that actually get a rookie to close on their first deal, instead of staying stuck in analysis paralysis.
0:25.4	This is the Real Estate Rookie podcast. I'm Ashley Care.
0:36.0	And I'm Tony J. Robinson. And in today's episode, we're going to focus on five key things that we would do if Ash and I were starting over in our portfolio today.
0:37.6	And the goal is that for all of the Rikis listening, you can take these five things, implement them into your strategy to make
0:41.8	sure that you're, by the end of this year, hopefully one of the folks we can bring on as a guest
0:45.5	to the podcast, say, hey, I listen to this episode, and now I'm the proud owner of my first
0:50.5	real estate deal. So five key things. The first thing that we do is we'd start by
0:55.6	asking the right questions. And what I mean by this is that oftentimes we see rookie investors
1:02.4	who just are kind of focused on the wrong thing when they're starting off their journey of
1:07.6	real estate investing. And sometimes it could be focused on steps that are maybe too
1:11.4	far ahead. Like, hey, well, how am I going to buy my second deal? How do I scale? And then, well, okay, well, you haven't done your first deal. Why are you worrying about scaling today? Or, you know, what does the legal structure look like? And, you know, I need this holding company based out of the Cayman Islands and all these crazy things.
1:28.2	And they're just asking the wrong question.
1:30.2	So the core questions that I would focus on first are what is my time availability?
1:36.5	How much time can I allocate toward my goal of investing in real estate?
1:41.5	What is my risk tolerance?
1:44.1	How much purchasing power do I have,
1:46.7	which is my cash on hand and my ability to get approved for a mortgage? And then what's my
1:50.3	motivation? So time availability, risk tolerance, purchasing power, and motivation.
1:56.3	For time availability, the reason that I start with this is because this is a limiting factor
2:01.4	for the type of deals that you should be focused on. Now, I will put a big caveat to this,
2:07.0	I hear oftentimes people say that the reason they want to invest in real estate is because
	...

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