I Built a Rental Portfolio That Gives Me “Boring,” Steady Cash Flow

Real Estate Rookie

BiggerPockets

How To, Education, Business, Investing, Entrepreneurship

4.8 • 1.7K Ratings

🗓️ 10 November 2025

⏱️ 38 minutes

🔗️ Recording | iTunes | RSS

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Summary

Don’t think you have enough time, money, or energy to invest in real estate? Living in an expensive and highly competitive market, today’s guest had every reason not to invest, yet has been able to build her own rental portfolio in just a few years—all while working a normal W-2 job. If she can do it, YOU can, too! Welcome back to the Real Estate Rookie podcast! Esther Simeone was stuck in a pricey market, and after submitting over a dozen offers and missing out on every one, she could have put real estate investing on the back burner and waited for the market to turn. But hell-bent on house hacking and building wealth with real estate, Esther kept looking. Finally, the perfect deal fell in her lap—an “overlooked” listing that now helps pay her mortgage! Since then, she has snagged a second property, used the Airbnb arbitrage strategy for more cash flow, and even designed an ADA-accessible vacation rental—a passion project that has given her a fresh perspective on what can be achieved through real estate. In this episode, Esther will show you how to get in the game today, no matter how little time or money you’re working with! In This Episode We Cover How to build and scale a real estate portfolio while working a W-2 job Using other people’s rentals to make money with rental arbitrage How to make “boring,” steady cash flow with medium-term rentals Covering your mortgage (or part of it) with the house hacking strategy Finding discounted investment properties by scouring old listings And So Much More! Check out more resources from this show on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠BiggerPockets.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.biggerpockets.com/blog/rookie-638 Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠[email protected]⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0	Our guest today is a digital marketing director in Los Angeles by day, but by night,
0:05.3	she's been secretly building a rental portfolio that now spans house hacks, midterm rentals,
0:10.6	and even an ADA accessible vacation home.
0:13.8	In just two and a half years, she's gone from zero properties to a cash flow portfolio.
0:18.8	Today's guest, Esther Simioni, proves that you don't need to start with a ton of capital to build purpose-driven cash flow portfolio. Today's guest, Esther Simeone, proves that you don't need to start with a ton of capital
0:23.0	to build purpose-driven cash flow.
0:25.2	And she's walking us through exactly how.
0:32.7	This is The Real Estate Rookie Podcast, and I'm Ashley Care.
0:36.2	And I'm Tony J. Robinson. And with that, let's give a big warm welcome to Esther. Esther, thanks so much for joining us today. Thanks so much. I've been a long time listener, so I'm really excited to be here. Now, Esther, you live in Los Angeles, which is one of the most expensive and competitive real estate markets across the country. Can you take us back to 2022? You submitted 15
0:57.0	offers in this hot market and you lost out on every single one. What was this like for you?
1:03.3	And how did it not discourage you from continuing your journey? For sure. If you guys remember
1:08.6	the market in 2021, 2022, the interest rates were at record lows at 3 to 4%, which meant that everybody was trying to buy a home before the rates potentially went back up. And we kind of had the same thought. We thought that the most straightforward and least daunting way, at least, to get into real estate,
1:27.8	was to purchase a primary home for ourselves and potentially house hack. And so we were just
1:33.4	really looking for a property where we could do that. At the time, open houses were just
1:39.1	absolute chaos. There were lines down the street. Rooms were crammed with people and you could just really feel that
1:48.3	competitive energy in the air. My husband and I did end up putting in about 15 offers and they were
1:54.9	all pretty solid offers, but we lost out on every single one. It was just bidding war after bidding war. And I remember one house that we were, we submitted an offer on actually went for $400,000 above asking. So that just kind of shows you the type of market we were in. Yeah. And by the 10th or 11th offer, I just remember thinking to myself,
2:22.7	is this what real estate really is? It just seemed pretty cutthroat. And it just seemed like
2:29.4	people with the deepest pockets were the ones that were winning. And it actually all ended up
2:34.9	working out in the end. We were able to actually purchase the perfect house that really did
2:40.9	help kickstart our real estate journey. Esther, let me ask, because 15 is a big number,
2:45.3	but it's also not 1,000, right? Or like, you hear about Colonel Sanders and it's taken like,
	...

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