If early retirement seems out of reach right now, try semi-retirement. Once you get there, you’ll only be halfway to early retirement, just like today’s guest, Jessie Dillion. At only thirty years old, she is semi-retired and has scaled her real estate portfolio to almost two million dollars in nine months, with five properties total!
When people think about high returns, they often think about a high unit count—but why have a lot when you can do the same with a few? Jessie is strategic about each property purchase she makes and has made a goal to make one smart investment each quarter. She currently has a single-family home and two duplexes. One of her duplexes is a house hack, and her portfolio sports a mix of long-term, short-term, and mid-term tenants.
Jessie’s success is due to how responsible she is with her finances. To finance her first property, she built up her savings to ensure she had enough to cover any surprises. As Jessie continues to scale, she has gotten more creative with her financing. She has formed great relationships with her lenders because of her ability to ask questions and carefully choose where and how she gets her funding. Now she is semi-retired at thirty years old and pays a measly fifty dollars a month towards her mortgage!
In This Episode We Cover
The FIRE movement and how to start your early retirement journey today
How to use transferable skills from other jobs to make investing easier
Building trust with your spouse and getting them on board with your investing journey
Getting the funding for your first rental property and how to use creative financing for the rest
Brilliant savings tips and how to rapidly increase your savings
The loan process and how to build a strong relationship with lenders
And So Much More!
Links from the Show
Find an Investor-Friendly Real Estate Agent
Ashley's Instagram
Tony's Instagram
Real Estate Rookie Facebook Group
On the Market Podcast
Jamil Damji's BiggerPockets Profile
Pace Morby's Instagram
Brittany Arnason's Instagram
Ashley Hamilton's Biggerpockets Profile
10 Deals on a $20K Waitress Salary With Ashley Hamilton
Rachel Richard's Instagram
Henry Washington's Instagram
Zillow
Furnished Finder
Craigslist
Facebook Groups
AirDNA
PriceLabs
Data.rabbu
Monday.com
Connect with Jessie:
Jessie's BiggerPockets Profile
Jessie's Instagram

Check the full show notes here: https://www.biggerpockets.com/blog/rookie-231
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231: Semi-Retired at 30 Thanks to One Year’s Worth of Real Estate Investing w/Jessie Dillion

Ready to build your real estate empire… but not sure where to begin?
Think of us as your personal trainer.
From detailed breakdowns of real-world deals… to one-on-one coaching sessions and a warm, welcoming community… hosts Ashley Kehr and Tony J Robinson bring on a wide range of guests to tackle the “newbie” questions you've wondered about but might be afraid to ask.
Looking to 10X your real estate investing business this year? This show isn’t for you.
Looking for your first, second, or third deal -- or envisioning a more modest portfolio? Step right up. 
Every Monday, Wednesday and Friday, we’ll arm you with the tips, tools, and roadmaps you'll need as you embark on your journey toward financial freedom.

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The hardest part of real estate investing is, of course, getting started. Once you have your first rental property, it’s much easier to scale your real estate portfolio than you might think—even if you don’t have much money to your name!
 
Earning modest salaries from their nine-to-five teaching jobs, Rob Schou and his wife couldn’t afford a large down payment on an expensive property. But by starting multiple side hustles and sharpening their DIY home renovation skills, they were able to purchase a cheaper property and add value to it. The best part? This created a “domino effect,” giving them more capital and momentum for future deals. Even when they didn’t have everything figured out, taking action and having multiple exit strategies meant they always turned a profit—even when a project didn’t go to plan!
 
In this episode of the Real Estate Rookie podcast, you’ll hear about some creative side hustle ideas you can use to fund your next down payment. You’ll also learn how to choose a niche that aligns with your long-term goals, as well as how to build your “buy box” and find the right market. But that’s not all. Rob even dives into new construction, showing you how to buy land, vet builders, and more!

In This Episode We Cover
The “domino effect” and how ONE deal can help you land your next deal
How to find the perfect investing strategy for your long-term goals
How to build your “buy box” and choose a market to invest in
Lucrative side hustles that can help fund your next down payment
Why you MUST have multiple exit strategies for every new deal
How to properly vet a builder for new construction projects
And So Much More!

(00:00) Intro
(00:58) Buying the Vacation Home
(10:51) Side Hustling for Down Payments
(16:39) Analysis Paralysis & Finding Your Niche
(24:16) New Construction 101
(28:26) How to Vet a Builder
(36:17) Choosing Your “Buy Box” & Market
(42:37) Connect with Rob!

Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-402
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402: The “Domino Effect”: How to Build an Entire Portfolio from ONE Property w/Rob Schou

Want more cash flow with less stress while running your rental property portfolio? Then you need self-management! Amelia McGee and Grace Gudenkauf, seasoned investors and the minds behind BiggerPockets’ newest book, The Self-Managing Landlord, show you exactly how to do it. This episode peels back the curtain on the misconceptions that scare most investors away from self-managing their properties (like those feared 2 AM toilet emergencies!). Amelia and Grace expose how these scenarios are less frequent than most people think and offer smart strategies to handle them effortlessly.
The duo dives into the financial perks of taking the reins on property management, from dramatically cutting costs to boosting tenant retention and cash flow. They lay out a spectrum of management models—from DIY to hiring a dedicated team—and share their personal triumphs (and trials) within each approach. This is THE practical playbook for making property management a cornerstone of your real estate success.
You’ll learn how to establish effective systems for tenant onboarding, routine maintenance, and urgent repairs, ensuring your property management is both stress-free and profitable. Whether you’re just dipping your toes into real estate investing with your first property or looking to refine your existing portfolio, this episode is packed with actionable tips that promise to make your portfolio more passive! 
In This Episode We Cover:
How to lower your costs and boost your cash flow significantly with self-management
What being a landlord is actually like, and why it’s not all 2 AM toilet calls 
Building your real estate team so you can handle less of the day-to-day and focus on the big picture
Practical advice for setting up systems that streamline tenant onboarding and property maintenance
Grace’s $8,500 bookkeeping mistake that you CAN NOT afford to make
Tips for handling urgent property issues with WAY less stress 
And So Much More!
Links from the Show
Find an Agent
Find a Lender
Ashley's BiggerPockets Profile
Ashley's Instagram
Tony's BiggerPockets Profile
Tony's Instagram
Real Estate Rookie Facebook Group
Join BiggerPockets for FREE
Submit Your Real Estate Rookie Question!
Get Tips, Advice, & Support in the BiggerPockets Forums
Get RentRedi Property Management for FREE with a BiggerPockets Pro Membership:
BiggerPockets Pro
RentRedi
Real Estate Rookie 111 - 26 Doors in 1 Year? Here’s How You Can Do It Too! w/Amelia McGee
Real Estate Rookie 161 - Using Calculated Risk to Acquire 17 Doors In Under a Year (at Age 24!) w/ Grace Gudenkauf
BiggerPockets Real Estate 938 - Scaling from 0 to 20+ Doors Using These “Self-Management” Tools & Tips w/Amelia McGee and Grace Gudenkauf
Tools Mentioned in Today’s Show:
Loom
Monday.com
Connect with Amelia:
Amelia's BiggerPockets Profile
Amelia's Instagram
WIRE (Women Invest In Real Estate)
Connect with Grace:
Grace's BiggerPockets Profile
Grace's Instagram

(00:00) Intro
(01:10) The Right Way to Manage Rentals
(04:42) What Being a Landlord is Like 
(08:20) Why You MUST Self-Manage 
(14:42) Onboarding Tenants 101
(20:41) Lease Agreements
(26:56) The $8,500 Mistake
(30:08) Do This RIGHT Now!
(35:09) Building Your Team
(41:40) Grab the Book!

Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-401
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401: Boost Your Cash Flow in 2024 with These “Self-Management” Tips w/Amelia McGee and Grace Gudenkauf

This episode could make you $40,000. Seriously, one property management mistake cost our own expert investor, Dave Meyer, anywhere from $30,000 to $40,000, BUT it’s easier to avoid than you think. If you’re a rookie real estate investor, this single mistake could sink your portfolio and put you back years on your journey to financial freedom. So, what’s the mistake you must avoid, and how do you circumvent it to make more money while having less stress? It’s Real Estate Rookie episode 400, so let’s save you $40,000!

Dave has been investing for over a decade, and he’s made his fair share of mistakes, but this one takes the cake. One simple property management judgment error sent his short-term rental trajectory off a cliff, with a filthy house, no bookings during the peak season, safety problems that left his property in jeopardy, and guests leaving less-than-flattering reviews. But this is a mistake anyone can make, so how do you avoid it?

In today’s episode, we’ll get into the nitty-gritty of what cost Dave $30,000 - $40,000, the exact way he’d prevent this from ever happening again, what you should look for in a property manager BEFORE you hire them, and the contract clause that could kill your cash flow!

In This Episode We Cover
The one property management mistake that could cost you up to $40,000
Property management fees and how to tell a company is a little too cheap
Signs you need to fire your property manager before it’s too late 
The one short-term rental contract clause that could ruin your entire year 
How Dave’s house almost froze thanks to overlooking one BIG utility 
And So Much More!

(00:00) Intro
(03:12) Buying a Property ASAP!
(06:57) Great Property, But…
(12:23) One Big Mistake 
(16:05) Things Go Really Wrong 
(20:07) Losing A TON of Rent 
(22:48) Costly Lessons Learned 
(28:43) Get a REAL Property Manager 

Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-400
Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email: advertise@biggerpockets.com
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400: Rookie Investor? Never Make This $40,000 Mistake w/Dave Meyer

What’s YOUR reason for investing in real estate? For today’s guest, it was to achieve financial freedom and have a flexible schedule. By focusing on education, forming partnerships, and, most importantly, taking action, she was able to quit her job and acquire seven properties in just THREE years!
Welcome back to the Real Estate Rookie podcast! Sarah Msuya was firmly entrenched in her successful banking career when life threw her a series of curveballs. After her son was born prematurely and complications caused her to miss nine months of work, Sarah knew that a traditional nine-to-five was no longer an option for her and her family. She spent the next three years learning as much as she could about real estate and building a portfolio that provides $80,000 in cash flow per year!
Like many new investors, Sarah has dabbled in several investing strategies on her journey to financial freedom—from house hacking to flipping houses and everything in between. Eventually, she was able to pin down her niche—the BRRRR method. In this episode, you’ll learn how to find the best strategy for YOU and scale your portfolio through partnerships and creative financing!

In This Episode We Cover:
How Sarah brings in $80,000 cash flow each year from seven properties
Why you DON’T need to look ten years ahead before investing in real estate
How to cover your mortgage payment with the house hacking strategy
Three property management strategies you can use for your rental property
How to scale your portfolio FAST with partnerships, creative financing, and more
FHA loan limits explained (and how to avoid a surprise at closing!)
And So Much More!
Links from the Show
Find an Agent
Find a Lender
Ashley's BiggerPockets Profile
Ashley's Instagram
Tony's BiggerPockets Profile
Tony's Instagram
Real Estate Rookie Facebook Group
Join BiggerPockets for FREE
Submit Your Real Estate Rookie Question!
Get Tips, Advice, & Support in the BiggerPockets Forums
Grab Your Copy of “Real Estate Partnerships
Real Estate Rookie 207 - Working Towards Time Freedom “In the Trees” with 3 Treehouse Rentals:
Real Estate Rookie 742 - How to Achieve Financial Freedom Through Real Estate in 4 Steps:
Connect with Sarah:
Eileen's BiggerPockets Profile
Sarah's Bigger Pockets Profile
Sarah's Facebook 
Sarah's Instagram 
Sarah's LinkedIn 

Jump to topic:
(00:00) Intro
(00:50) HUGE Life Changes
(06:42) $80K/Year Cash Flow!
(13:31) Sarah’s First House Hack
(20:52) How to Scale FAST
(27:51) Property Management 101
(31:57) Connect with Sarah!

Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-399
Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email: advertise@biggerpockets.com
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399: $80,000/Year Cash Flow & Financial Freedom with 7 Properties (in 3 Years!) w/Sarah Msuya

Small multifamily real estate investing can lead you to financial freedom faster than you think. Compared to traditional single-family rental properties, small multifamily properties often offer more cash flow, the ability to scale quicker, and less competition than the properties every first-time home buyer is looking for. Small multifamily investing is so good that it remains seasoned investor Dave Meyer’s favorite way to invest after over a decade of investing in rental properties. So, how do you get started?
In this episode, we’ll walk through the three beginner steps anyone can take to start investing in small multifamily real estate. We’ll show you how ANYONE can get into this asset class, even with ZERO experience, why small multifamily is the perfect “sweet spot” for rental property investing, and how to overcome the biggest challenges to getting your first deal.
But that’s not all. We found a small multifamily rental property for sale and go step-by-step through it, analyzing it within minutes so YOU can do the same for your first or next property. Small multifamily is the perfect place to start your real estate investing journey, and after you watch this episode, you’ll have EVERYTHING you need to start investing!
Ready to become a BiggerPockets Pro? Click here to sign up and use code “MULTIPOD24” for a special discount!

In This Episode We Cover:
Why small multifamily real estate is the perfect “sweet spot” for rookie investors
How to get to financial independence faster than you think with duplexes, triplexes, and quadplexes
The easiest way to find deals in your target market (for FREE!)
How to analyze a real estate deal from start to finish in just minutes
The #1 challenge to real estate investing and a simple solution to overcome it
Our favorite real estate investing tool that’ll help you do your first or next deal even faster
And So Much More!
Links from the Show
Find an Agent
Find a Lender
Dave's BiggerPockets Profile
Dave's Instagram
Real Estate Rookie Facebook Group
Get 20% Off a BiggerPockets Pro Membership with Code “YTMULTI24”
Analyze Deals in 5 Minutes or Less with Our Rental Property Calculator
Determine Monthly Rent with Our Rent Estimator Tool
Join a BiggerPockets Bootcamp
“On the Market” Podcast
Book Mentioned in the Show
Real Estate by the Numbers by Dave Meyer and J Scott

Jump to topic:
(00:00) Intro
(05:43) Want Financial Freedom?
(10:11) ANYONE Can Do It
(11:47) The Investing "Sweet Spot"
(12:57) Why Small Multifamily? 
(16:16) 1. Where to Find Properties 
(20:09) 2. How to Analyze Multifamily 
(31:23) 3. How to Get Financing 
(36:08) Scared to Invest?
(38:44) The One Tool You NEED

Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-398
Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email: advertise@biggerpockets.com
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231: Semi-Retired at 30 Thanks to One Year’s Worth of Real Estate Investing w/Jessie Dillion

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