Are you in this business to make a quick buck—or are you looking to build generational wealth for you and your family? If the latter is true for you, don’t miss a moment of this powerful show with bestselling author Ryan Holiday. 
Ryan, best known for his books, such as The Obstacle Is the Way: The Timeless Art of Turning Trials into TriumphA, Trust Me, I’m Lying: Confessions of a Media Manipulatorr, Ego Is the Enemye, and Perennial Seller: The Art of Making and Marketing Work that Lasts , is also a part-time real estate investor and lender. 
In this show, we cover a large variety of topics including hard money lending, vacation rentals, writing books, how the awareness of death can make life better, stoicism, and much, much more.
In This Episode We Cover:

Ryan’s background


The importance of learning from other people


His experience as Director of Marketing for American Apparel

Tips on looking for a mentor


His first real estate adventure

His thoughts on Airbnb


How he gets leads for loans


How to do what you love through passive income


The story behind The Obstacle is the Way


How to react to economy collapse



Advice to investors who only see the obstacle

How to control your ego


Why you should do the right thing despite not sharing it

And SO much more!

Links from the Show

BiggerPockets Forums

BiggerPockets Facebook

BiggerPockets Books

BiggerPockets Webinar

Josh’s Instagram Profile

Brandon’s Instagram Profile

Derek Sivers

Books Mentioned in this Show


Set for Life by Scott Trench


Finding and Funding Great Deals by Anson Young


The Obstacle Is the Way by Ryan Holiday


Trust Me, I’m Lying by Ryan Holiday


Ego is the Enemy by Ryan Holiday


Perennial Seller by Ryan Holiday


The 48 Laws of Power by Robert Greene


Cashflow Quadrant by Robert Kiyosaki


Rich Dad Poor Dad By Robert Kiyosaki


The Millionaire Next Door by Thomas J. Stanley


Fooled by Randomness by Nicholas Taleb


The Black Swan by Nicholas Taleb


Antifragile by Nicholas Taleb


Billion Dollar Lessons by Paul B. Carroll & Chunka Mui

Fire Round Questions
Best Way to Invest a Large Lump Sum of Money ($100-$300K)?
Tweetable Topics:

“Any fool can learn by experience. I prefer to learn by the experience of others.” (Tweet This!)

“Every single business is hiring if you can help them make more than you cost.” (Tweet This!)

“A mentorship is not a destination, it’s a process that ensues.” (Tweet This!)

Connect with Ryan

Ryan’s Instagram Profile

Ryan’s Website

Daily Stoic



      
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245: Creating Wealth that Lasts Generations with Bestselling Author Ryan Holiday

On the BiggerPockets Real Estate Podcast, co-hosts David Greene and Rob Abasolo interview real estate investors and entrepreneurs about successes, failures, and hard-earned lessons. Through in-depth conversations, 1-on-1 listener coaching calls, and news analysis, you’ll get a breakdown of real strategies that work for different niches and experience levels. Tune into the #1 real estate investing podcast every Monday, Wednesday, and Friday.

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There’s one way to invest in real estate that’s cheaper, easier, and more efficient than almost any other strategy. It allows you to get the best mortgage rates with the lowest down payments and buy properties in the best areas. And you can do it every single year until you grow a massive real estate portfolio. Real estate millionaires have been made using this strategy, but most Americans have no idea about it. What’s the wealth-building secret that savvy investors are taking advantage of? Of course, it’s house hacking.

If you’ve never heard of house hacking before, the concept is simple: You buy a single-family home or a small multifamily property and rent out the space you’re not using. This not only allows you access to the best mortgages but also keeps your mortgage cost lower than living on your own. This strategy is so good that expert investor Dave Meyer and today’s lender guest, Terrence Terrell, have used it repeatedly to build serious wealth.

If you’re a first-time homebuyer or have a home but want to get into rental property investing, this is THE strategy to try first. Terrence gives a beginner-friendly masterclass on house hacking, showcasing the huge benefits of house hacking’s low-money-down loans, what you need to have to qualify for a mortgage, the common misconceptions most people get wrong about house hacking, and how to use this strategy to build wealth fast.

In This Episode We Cover
House hacking explained and why it’s the easiest beginner real estate investing strategy 
How to buy your first investment property with as little as ONE percent down 
Qualifying for a mortgage and what first-time homebuyers must know before they apply
The free way to find out whether or not you’ll be able to get financing for your house hack
The easy, low-money-down way to build a real estate portfolio by house hacking 
And So Much More!

(00:00) Intro
(01:26) What is House Hacking?
(03:16) Put Just 1% Down!
(07:50) Who Should House Hack?
(09:28) It's Not as Hard As You Think
(11:55) What Homebuyers Need to Know
(14:51) Qualifying for a Mortgage
(18:43) Advice for First-Time House Hackers 

Check out more resources from this show on BiggerPockets.com and  https://www.biggerpockets.com/blog/real-estate-950
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950: The Easiest Way to Invest in Real Estate in 2024 w/Terrence Terrell

Would you buy a rental property that loses money every month? What if, in a few years, that one property could make you hundreds of thousands of dollars? Would the negative cash flow be worth the massive appreciation upside? Today, we’re answering that exact question from an investor who could be sitting on a wealth-building opportunity but doesn’t know what decision to make. Should he buy the "bleeding" property at a steep discount or give up this needle in the housing market haystack to avoid a cash flow trap? Let’s find out!

We’re back on Seeing Greene as David and Rob, your go-to real estate investing experts, answer questions directly from BiggerPockets Real Estate listeners like you! First, an investor has a rare opportunity to buy “Grandma’s house” with over $200K+ in potential equity upside. The problem? It will LOSE $800/month! Next, a new property manager wants to know how to raise rents on a twenty-year tenant. Do you pay capital gains on the profit of your home sale or the entire amount? We’ll show you how to know how much you owe. Then, an investor debates selling his C-class cash-flowing properties in exchange for appreciating assets, and we explain the “sneaky rental” tactic that’ll take you to ten rental properties in no time!

Want to ask David a question? If so, submit your question here so David can answer it on the next episode of Seeing Greene. Hop on the BiggerPockets forums and ask other investors their take, or follow David on Instagram to see when he’s going live so you can jump on a live Q&A and get your question answered on the spot! 

In This Episode We Cover
Negative cash flow and one of the ONLY times it makes sense to buy a “bleeding” rental
How to raise rents (the right way) on a long-term tenant 
Capital gains tax explained and how much YOU could owe on your next home sale
Whether to trade cash flow for appreciation and selling your rentals that don’t have room to grow 
The “sneaky” rental tactic that allows you to scale a real estate portfolio FAST 
And So Much More!

(00:00) Intro
(01:23) Losing $800/Month to Make $200K?
(11:59) Raising Rents On 20-Year Tenant 
(21:28) Comment Section & Capital Gains 101
(25:47) Trade Cash Flow Portfolio for Appreciation?
(33:05) The "Sneaky Rental" Tactic
(38:20) Ask Us Your Question!

Check out more resources from this show on BiggerPockets.com and  https://www.biggerpockets.com/blog/real-estate-949
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949: Seeing Greene: Is Losing $800/Month in Cash Flow Worth $200K+ Equity?

When you think about short-term rental and Airbnb markets, what comes to mind? Joshua Tree, the Smoky Mountains, maybe Destin? We all know about the famous short-term rental markets, but what about the not-so-famous ones? You know, the unsexy markets where you book an Airbnb for a conference or when you’re going to see extended family? That’s right; we’re talking about everyday American markets like Cincinnati, Ohio. But surprisingly, these markets make some of the best investments for short-term rental investors like Jarrod Tucker and Yiwei Cheng.

Jarrod and Yiwei moved to Cincinnati for work shortly after catching the real estate investing bug. They knew they wanted to invest in real estate, but long-term rentals only came with measly cash flow that would never support their passive income goals. So, what’s the next best option? Short-term rentals! Unfortunately, Cincinnati isn’t known as a popular vacation getaway, but it didn’t have to be to support Jarrod and Yiwei’s cash flow dreams!

Now, five years after the start of their investing journey, they have ten rentals of their own and manage a couple dozen more for other investors. The question is, how do you make money with short-term rentals in an unsexy market? Jarrod and Yiwei walk through their tips for finding the right properties, keeping occupancy rates high, buying real estate when your DTI (debt-to-income) gets maxed out, and why you MUST separate yourself from the basic short-term rentals to reach your financial goals.

In This Episode We Cover
The three types of short-term rental guests who consistently come to markets like Cincinnati 
How to set your Airbnb apart if you’re in a saturated short-term rental market 
Tips for higher occupancy and what you MUST have to get more bookings 
Scaling your real estate portfolio when you have high DTI (debt-to-income)
Using partnerships to buy even more properties when you’re low on cash
Why you DON’T need to invest in high-priced, popular vacation destinations 
And So Much More!

(00:00) Intro
(01:36) The Accidental Airbnb Host 
(08:07) Short-Term Rentals in…Cincinnati? 
(13:37) Are Short-Term Rentals Saturated?
(19:46) Tips for Higher Occupancy
(22:31) Scaling with High DTI (Debt-to-Income)
(32:24) Advice for New Investors 

Check out more resources from this show on BiggerPockets.com and  https://www.biggerpockets.com/blog/real-estate-948
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948: 10 Rentals in 5 Years by Buying in Overlooked Short-Term Rental Markets w/Jarrod Tucker and Yiwei Cheng

Want a low mortgage rate? We mean a really low rate—like 4.75% in 2024 low. What about half a million in profit on a sneaky development deal? Or, maybe you’d settle for a quick house flip that pockets you $55,000 on a bad day. These aren’t made-up numbers; these are REAL deals that our expert investing panel is doing in today’s hot, hot housing market. And if you know where to find deals and steals like these, you, too, could be taking home huge profits like they are! Thankfully, they’re sharing all their secrets on today’s episode!
David and Rob are taking some time off to play pickleball, while Dave Meyer and the entire On the Market podcast panel join us today! In this show, we’re talking about the real estate deals getting done in 2024. Each expert brings in a deal they’ve recently done and showcases how they found it, what they bought it for, how much cash flow or profit they’re going to make, and advice to help YOU repeat these home-run real estate deals.
First, Dave will share about a cash-flowing on-market rental property he bought (while abroad!) thanks to his inventor-friendly agent. Kathy Fettke gives tips on getting a low mortgage rate on your next new construction rental and how doing so could massively boost your cash flow. Henry Washington walks through a quick flip that will make him $55,000 on the low end and the ingenious way he found this deal. And finally, James Dainard talks about the almost unbelievably good development deal he’s doing in Seattle that will profit $500,000 (yes, that’s half a million!).
In This Episode We Cover:
How to score a mortgage rate in the four-percent range by buying new construction rentals
The three big housing market challenges of 2024 and how investors can overcome them
How to find cash-flowing, on-market rental properties by investing out-of-state 
One of the smartest ways to find off-market real estate deals for flipping or holding 
The one contract clause that is helping James make $500K+ on his new development deal 
And So Much More!
Links from the Show
Find an Agent
Find a Lender
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Join BiggerPockets for FREE
Learn About Real Estate, The Housing Market, and Money Management with The BiggerPockets Podcasts
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Ask David Your Real Estate Investing Question
Dave's BiggerPockets Profile
Dave's Instagram
Henry's BiggerPockets Profile
Henry's Instagram
James' BiggerPockets Profile
Kathy's BiggerPockets Profile
BiggerPockets' Instagram
On the “On the Market” Podcast
Investing in Real Estate Out of State: What You Need To Know
4 Vital Points to Consider BEFORE Getting Into New Construction
Flipping Houses: How to Get Started and Everything You Should Know
What Exactly Is an Accessory Dwelling Unit (DADU/ADU)

(00:00) Intro
(01:19) Investing Challenges of 2024
(08:17) 1. Cash-Flowing On-Market Rental
(14:41) 2. New Construction with a 4.75% Rate! 
(20:44) 3. $55K House Flip Profit!
(26:11) 4. Making $500K with DADUs!
 
Check out more resources from this show on BiggerPockets.com and  https://www.biggerpockets.com/blog/real-estate-947
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947: 2024 Deals We’re Doing with High Cash Flow and Rock-Bottom Rates (4.75%!)

Why are rock stars turning to real estate side hustles to pay their bills? During the lockdowns, many musicians, gig workers, and creatives saw their income streams dwindle. There were no shows to play, no tours to attend, festivals were canceled, and human-to-human contact was limited as much as possible. As a result, famous musicians began to become real estate agents, mortgage brokers, investors, house hackers, and everything in between to pay their bills. And guess what—it worked! 

Now, touring is back on, but those whose job is pursuing their passions still need extra income to take care of their bills during slow seasons or to build wealth. That’s where Juliet Lalouel from Heavy Realty comes in. Juliet is a Colorado and Hawaii-based investor and real estate agent who helps the music and creative communities find ways to fast-track their financial freedom to keep doing what they love. But her message doesn’t just apply to musicians. Anyone who loves what they do but wants more financial stability can take these lessons to heart.

Today, we’re talking about how anyone from any background can use real estate to supplement their income, pay their bills, and help them build wealth. Juliet shares why you may make a great real estate investor/professional without even knowing it and the beginner investments that ANYONE can try to start building a strong financial fortress, even if you’re a real estate enthusiast by day and a rock star by night. 

In This Episode We Cover
Real estate side hustles that’ll help you make extra income no matter your experience 
Why musicians and creatives make GREAT real estate investors 
The best ways to start making money with real estate and how to find your perfect role
Beginner investments for anyone to start building wealth today
Financing your first investment property, even if you DON’T have a W2
Why real estate is the ultimate side income stream to support your dreams 
And So Much More!

(00:00) Intro
(01:36) Anyone Can Invest 
(05:07) Why Musicians Make Great Investors 
(07:53) The Best Way to Get Started 
(13:40) Beginner Investments 
(17:57) Financing Your 1st Property 
(20:52) Do Your Passion Full-Time 

Check out more resources from this show on BiggerPockets.com and  https://www.biggerpockets.com/blog/real-estate-946
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245: Creating Wealth that Lasts Generations with Bestselling Author Ryan Holiday

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