BiggerPockets Real Estate Podcast

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

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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 Triumph, Trust Me, I’m Lying: Confessions of a Media Manipulator, Ego Is the Enemy, 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.

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This Show Sponsored By

patchoflandWe just wanted to give a shout out to our podcast sponsor on today’s show: Patch of Land. Patch of Land is a Peer-to-Real-Estate (“P2RE”) lending marketplace that matches accredited and institutional investors seeking high-yield, short-term, asset-collateralized investments to borrowers seeking more timely and consistent sources of funding for rehabbing properties across America.

Learn more by visiting Patch of Land!

Fire Round Sponsor

We just waRealtySharesnted to give a shout out to our podcast sponsor on today’s show: RealtyShares. RealtyShares is a crowdfunding platform that allows you to invest in professionally managed properties without leaving your living room!

Learn more by visiting!

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

Books Mentioned in this Show

Fire Round Questions

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

Real strategies that work for real people seeking to build wealth through real estate investments. Co-hosted by Brandon Turner and David Greene, this podcast provides actionable advice from investo...
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    Replied over 2 years ago
    I bought one of his books. The books is awesome! I found so much wisdom. A great author!
    Andrew Syrios Residential Real Estate Investor from Kansas City, Missouri
    Replied over 2 years ago
    Ego is the Enemy was a great book! Very good podcast!
    Don Spafford Investor from Idaho Falls, ID
    Replied over 2 years ago
    Very thought provoking episode. Hey @Joshua Dorkin check your PM from a couple days ago. Following the discussion of this podcast, I sent you a great idea to improve your company.
    JD Martin Rental Property Investor from Northeast, TN
    Replied over 2 years ago
    Man, that was interesting to listen to – like Josh said, it’s a little change from the concrete to the blueprints. Nice stuff!
    John Clark Investor from Pinckney, Michigan
    Replied over 2 years ago
    That was a very interesting podcast. (in a good way) I had never heard of Stoic before. I like the different approach of looking at situation. Nicely done guys, Also, what happened to the Random 5 (+1) ??
    Mitchell Z. Real Estate Agent from South Lyon, Michigan
    Replied over 2 years ago
    I’ve been a long time investor and regular listener of the BP podcasts – I have to say that this is BY FAR my favorite episode! I don’t know why but where I’m at personally and professional aligned with this episode perfectly! I’m so glad that you guys are able to do what you do and that you do it so well!!! Please keep up the good work 🙂
    Kevin Leonce Investor from Atlanta
    Replied over 2 years ago
    Hands down one of the best episodes. I’ve replayed it a couple times as there’s so much valuable information to take away. Great job!!
    Charles Oglesby from Orange County, California
    Replied over 2 years ago
    Always great hearing Ryan talk. Great episode
    Link McGinnis Investor from Knoxville, Tennessee
    Replied over 2 years ago
    Great podcast on many levels. I thought I might correct one thing that was said. Ryan prefaced a comment by saying he wasn’t religious but then erroneously stated what Christians believe. He said, “The Christians would say, ‘You shouldn’t do bad things because if you do bad things God will judge you and then you’ll go to hell.'” (~10:10) As a Christian I thought I might provide the truth of the matter. The Bible is clear that “all have sinned…” So, if we all have sinned, how is there any chance for any of us to go to heaven, if Ryan is correct? As a matter of fact, we’re all sinners because we inherited that from Adam (thanks, Adam!). In the first part of the Bible or in the Torah, you’ll see that God gave the Jews a sacrificial system that allowed their sins to be cleansed. Later, Jesus, the son of God, left his place in heaven to be born as a man, live a perfect life and then die on a cross. He was buried and then resurrected to life and seen by many. His death and resurrection was the sacrifice of all sacrifices paving a way for humans to be “saved” from their sins. Salvation from the curse of sin and Hell is a complete gift, “not of works, so no one can boast.” In other words, I can’t be good enough to “earn” eternal life. I can only attain it by trusting in Jesus’ sacrifice. By the way, at the end of his comment Ryan said, “Right?” (which he did after many of his comments) and Josh followed with “right” meaning you agreed. And, Brandon didn’t say anything. I would have thought that as long as the two of you had worked together (Jew and Christian) you may have had this conversation and at least Josh would know the correct stance! Again, this was a very good podcast episode. Thanks for doing what you do!
    Nathan G. Real Estate Broker from Cody, WY
    Replied over 2 years ago
    A very long podcast but it kept my attention the entire time. There is a lot of really good advice for life in general, and all of it is applicable to real estate investing. One of the things I appreciated the most is to see Josh and Brandon grounded in reality. It’s very easy to get caught up in a strong market and feel like a genius because all your business decisions are working out. It’s much harder to remain objective and recognize that the only consistent thing in life is change (and death, but that’ doesn’t pertain to the discussion). The market will change and it’s important to take steps to avoid over-extending ourselves and losing it all because of our ego. I honestly don’t have a problem with ego and can’t imagine I ever will but I’ll still buy Ryan’s book because I’m sure there’s something to learn there.
    Jason Unrath from Collegeville, Pennsylvania
    Replied about 2 years ago
    So, I have an idea to do live stream walk-throughs for my flip projects. What I would do is live stream an initial walk-through to show the state of the house on purchase closing day and also to explain my plans for how I’m going to fix it up. Sort of like a “coming soon” advertisement. Then, after all work is completed, I would live stream another walk through to show the finished product being listed on the MLS. I mean for this to be a creative marketing strategy to sell homes, but at what point does it become perceived as an egotistical “look what I’m doing” kind of ploy?