Ex-Goldman | $150M+ multifamily | Building the next empire through cycles, history & contrarian real estate

Portland, OR
Closed our latest deal last month - The Crown Point Apartments - here in 'always' sunny Portland, Oregon. More on this: 1. $140,000 a door for 1000 square foot (on average) units 2. Over a 7 cap on actuals going in 3. Seller financing at 5% Interest Only for 5 years 4. In-House Managed from Day 1 We've already achieved a 10% increase in rent on units for 2 new leases (versus in-building averages). Target ~10% CoC Yield from day 1. LFG!
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Today's my 40th birthday. As I cross into the 5th decade of my life, it's a great time to reflect. These big ones always are. In four decades on our fair blue planet, I was fortunate enough to marry to my college sweetheart, have four beautiful children, experience great wins and losses, start my own business, witness my father's eventual losing fight with cancer, and to see ups and downs of all sorts and magnitudes for this great nation of ours. Going into my fifth decade, I imagine the next 10 to 20 years will be very similar. Wins and losses. Trials and tribulations. Glory and failure. The one area I think I've gotten wiser is on "purpose". As a young man I was consumed with a desire to "make it", to "become someone important", etc etc. As I've gotten older, and maybe a bit more mature (and wise), I have realized what a farce that is. Some of the unhappiest people I know are also quite successful. What I really want, at this point in my life, is a pleasant, sun-filled afternoon with my children, family and my friends. My kids won't remember how hard I worked, nor any businesses I built (unless it outlasts me, I suppose). What they WILL remember is the numerous times I was too stressed out to read them a book at night, or say prayers with them, or any of the other innumerable small things that really matter but seem irrelevant in the moment. So - I pray that the next 40 years of my life (and yours) are ones filled with more peace, less stress, and more connection with our families and our friends. May God bless us all!
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Who knew that keeping properties available on waitlist on Zillow could produce so many tours at OTHER properties. Amazing. 🤯
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Water leak through multiple units. We find the source (3rd floor bath). Resident says … oh yeah I noticed the toilet was leaking onto the floor a few days ago. I mean cmon. Say something man!
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I love trees. But as a property owner I also sort of hate them. It's a love/hate relationship.
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In the biz (real estate) you've simply got to watch expenses like a hawk. I noticed we were getting a lot of overage charges on garbage. Something like $100-200 a violation. Below is the "violation" that cost us ~$200. You can bet your banana we're disputing this puppy.
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Seneca. Stoic philosopher. Tutor to Nero. Author of a tremendous book I've read cover-to-cover three times. Also, as it turns out, a predatory lender who (maybe inadvertently) helped start a war. Here's the tale. In 60 AD, Queen Boudica led a savage and extremely bloody revolt against the Roman Empire. She sacked a Roman city housing veterans and their families and massacred everything within. The 9th Legion, en route to stop her, was ambushed and crushed. Boudica was finally stopped, at great cost, at the Battle of Watling Street, and took her own life. One of the epic, tragic, horribly bloody tales of the period. Heck — every period has this sort of thing. But the REASONS for the revolt are many. One of the main culprits? My main man, Seneca. Back to the start. The Philosopher. He has a real claim to being perhaps the wealthiest philosopher in history. He was ALSO a massive "lender" to the Britons. Mind you — these were not loans the Britons necessarily wanted, or fully understood. But to the Roman mind, they were loans. And at some point, Seneca called them. All at once. Critical question: what was the collateral? In this era? Land, holdings, slaves… and family members. Which Roman soldiers proceeded to enforce with "severe measures." The loan was secured by the collateral. But enforcing the loan actually destroyed the collateral. Seneca never saw a sesterce of it back. There is SO MUCH here to learn from. Underwrite your lender — their temperament, their balance sheet, their desire to work with you. Understand the terms of your contract. Know what happens to the asset if they pull. The list goes on and on. Full write-up: The Philosopher Who Called His Loans. Link below!
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Sometimes, owning good real estate requires vision. Like with Hong Kong. Imagine passing on taking property there when the British first "acquired" the land. The rub is that sometimes your vision is wrong, and hindsight is 20/20. So stay bold. But don't bet the house. Literally.
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Full video on The Opium Wars, when the British Empire went to war to force a fix to their trade deficit problem, AND force the Chinese to accept drugs - at gunpoint. piped.video/o_rbmTl_W0Q
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About 18 months ago, I went all-in on building a newsletter. It’s been a ton of fun—and a ton of work. I occasionally get criticized for it: "You seem focused on social media to the exclusion of investing." I don't see it that way. Forcing yourself to form coherent arguments in writing is one of THE best ways to stress-test your ideas and grow as an investor. You get to study other people's wins and losses. In other words, you gain an education without paying the (usual) tuition of losing money on your own account. Though, of course, that happens too.
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Never put money on your political beliefs. Be completely agnostic. Go where money can be made. And if your "where money can be made" thesis is primarily driven by "so and so party is good for money", then (I think) you ought to rethink it.
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Does anybody else find it interesting that real estate alone seems to attract a host of coaching programs? Maybe it's just my exposure to the industry, but I don't "see" that the same thing exists for other forms of investing.
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Here's WHY I think. Everybody knows somebody who got rich from real estate. It's the American Dream. It's tangible. You can show it off to people. It "seems" like something anybody could do. And so there are a lot of people who "sell" that dream to your everyday person.
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Long end already doing a lot of the tightening ATM. Is the case for a hold tomorrow that financial conditions have moved enough, or does skipping a priced hike just push 10s and 30s higher on credibility grounds? I get the argument to raise. I also get the argument to hold. And I get (because it's good for me) Trump's argument to cut.
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Theoretically real estate deals exist in all markets. But real estate pricing is also slow. So when you have a massive interest rate upswing like this, you have to know that a) pricing hasn't kept up (yet), and b) it might be a moot point if yields come back down violently (which has been the case over the last few years). It "also" might stick. Just one of many reasons that investing is hard.
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One truism in investing is that people fight the last bear market for at least a decade after it. It is exceedingly rare (dare I say it's never happened) for there to be a huge blowup, and then the "same exact thing" happens 10 years later. After the Great Depression, American's swore off stocks and margin. And the next downturn had nothing to do with it. Or to go back, in 1720 John Law and his schemes destroyed France's faith in paper currencies for at least an entire generation. (Maybe a prudent choice that time). In any case - you can be relatively sure that the NEXT blowup won't be caused by the same catalyst as the last blow up.
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The hardest part of being a great investor or business builder or successful W2 wage climber is managing yourself. Which is a great spot to be in, objectively. But managing inevitable ups and downs, mood, emotions, feeling tired, feeling "over-it". All of that. Just successfully managing yourself, maintaining equilibrium and keeping on pushing forward is the ENTIRE game. Applies equally to all businesses, all industries, and all people.
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When in doubt, always follow the money. Economics rule all facets of life. We have only to look at the infamous Opium Wars to see exactly what I mean. Let me know if this scenario sounds familiar. A major western power has a massive trade imbalance with China. China has no desire for (or no will to) trade FOR goods said Western Power makes, and the trade imbalance enriches China and impoverishes the Western Power in a variety of ways. And then ... the Western Power forces a "trade imbalance" fix by forcing China to accept drugs. By force of arms. Everything except the drug war could be a parallel to our current trade deficits with China. I'd argue this war was one of THE pivotal moments in Chinese History, as it undergirds the entire narrative around the Century of Humiliation. And remains a critically important lesson that the Chinese Government today brings to every decision they make. Little bit below on the Trade Imbalance itself ... and what the British ultimately did. Full video available on The Timeless Investor Show. piped.video/o_rbmTl_W0Q
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Weightlifting might be like the perfect analogy for life. You don’t see results for a long time. It’s frustrating at times. Requires commitment, endless time investment, and a meticulous approach to your nutrition. And then 12 months later you’re like oh that’s why. (Maybe) Typed between a set at the gym as I’m thinking about this and how I can’t seem to bench more.
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I’m kind of tired of LinkedIn. I spent over a year working dogmatically on it but I find the banter and information on X to be like 100x more useful/informative and occasionally funny. I get sports news here (go 49ers), treasury markets, real estate, the latest AI doomslop, and so much more. What is not to love?
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