Oak Street Assets Investing Blog
Generate passive income, grow your wealth, and live a better life through private investments.
MOST RECENT
AI Is Coming for Jobs. Inflation Is Coming for Dollars. Who Wins?
Why asset ownership may become more important than career success. Part II of the Asset Economy series.
Categories
ALL POSTS
Public REITs vs. Private REITs: What Investors Need to Know
Not all REITs are alike. How public and private REITs work, the pros and cons of each, and where private structures fit.
Can You Really Invest Passively in Real Estate?
Yes, but “passive” means very different things. A plain-English guide to the types of passive real estate and the honest trade-offs behind each.
But I Already Own Real Estate — I Have REITs
A public REIT is not real estate. It’s a real estate flavored stock. Here’s how REITs really behave, how they’re taxed, and what owning the real thing looks like.
Legacy by Design – Part IV: Living the Legacy – Daily Practices, Coaching, and Modeling That Keep Your Legacy Alive
The final chapter in the Legacy by Design series: the daily habits, rhythms, and relationships that keep a family legacy alive — not just protected on paper, but lived every day.
The Income Trap: Why High Earners Fall Behind and How Assets Fix It
There are two economies operating in America today. The Income Economy and the Asset Economy. Most people spend their entire lives in the first. A smaller group quietly benefits from the second. Understanding the difference may be one of the most important financial lessons of our time.
Why “Oak Street Assets”? The Story Behind the Name
Every now and then, someone asks me: “Why Oak Street Assets?” The answer tells the story of who we are, why we do what we do, and the philosophy that drives everything we build.
Understanding Your K-1 (Simple, Fast, No Surprises)
Every year investors ask the same question: I got this K-1 — what do I do with it? Here’s what it means, what to look at, and what to do. Simple. Fast. No surprises.
UDFI & IRA Investing in Real Estate Syndications: What You Need to Know
Most IRA investors using leverage in real estate syndications pay little to no tax during the hold period—and only a small amount at sale. Here’s why, and what UDFI really means for your returns.
Why I’ve Said No to Capital
There’s a quiet assumption in investing that more capital is always better. At Oak Street Assets, that hasn’t been true. Over the years, I’ve said no to investors who genuinely wanted to work with us—not because they were bad people, but because fit matters more than funds.
Legacy by Design – Part III: Protecting the Legacy – Structures, Trusts, and Family Systems That Endure
“A good person leaves an inheritance for their children’s children…” — Proverbs 13:22 Introduction Part I of this...
The Post-Holiday Reset Your Most Important Asset Depends On
'The healthy person has a thousand wishes. The sick person has but one.' In addition to the New Year signaling an...
The Buffett Indicator and What It Is Quietly Telling Us
Two questions keep coming up in nearly every conversation I have lately. Is now a good time to buy real estate? Where...
Where Are We in the Market Cycle?
Investors ask this question constantly, especially during periods of uncertainty. The short answer is this: we believe...
Demystifying Real Estate Syndication: A Practical Field Guide for Busy Investors
A quick story to set the stage When I traded my neuroscience lab coat for the world of real estate, friends were...
Legacy by Design – Part II: Building the Legacy – Creating Assets of Health, Wealth, and Wisdom
You don't just leave a legacy. You build one. Introduction Part I of this series redefined legacy—not as stuff you...
Impact + Income: How Your Capital Can Do Good While Working for You
For decades, investing was often framed as a cold calculation: maximize returns, minimize risk, and let ethics or...
The Science of Compounding: Why Patience Outperforms Hustle in Wealth Creation
I have been digging into 50 years of return data across four big U.S. asset classes: stocks, residential real estate,...
My Take on the $100M Money Models Launch
When Alex Hormozi announced the launch of $100M Money Models for August 16–17, 2025, it felt like half the business...
Most Popular
The Income Trap: Why High Earners Fall Behind and How Assets Fix It
There are two economies operating in America today. The Income Economy and the Asset Economy. Most people spend their...
Legacy by Design – Part I: Redefining Legacy — It’s Not About Net Worth
"Most people confuse legacy with a legal document. But true legacy isn’t passed through paper—it’s passed through...
Designing a Life You Don’t Need a Vacation From
“Success is the progressive realization of a worthy goal or ideal.” —Earl Nightingale Most people live for the weekend...
Tax Benefits of Real Estate: What Every Investor Should Know
Before I get into the key tax benefits of real estate investing, I need to make one thing clear: At Oak Street Assets,...
Why Multifamily?
“Landlords grow rich in their sleep without working, risking or economizing..” — John Stuart MillWhy invest in...
Why Real Estate?
“Ninety percent of all millionaires become so through owning real estate.” — ANDREW CARNEGIEWhy invest in Real...