Founder Letters

The Best Reason to Have an IPS Has Nothing to Do With Returns

It’s really a decision-making document. It should make decisions easier.

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If Money Were No Object

You can divorce your decisions from the dollars.

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HSA Tax Savings Essay

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What Happens When Robots Come Home?

A conversation about robots, post-scarcity, capitalism, and what humans do when machines can do more of the work.

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Tax Savings Series - Installment #3

Direct Indexing - A Smarter Version of Index Investing (With a Tax Loss Harvesting Strategy Most Investors Miss)

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Will AI Take Our Jobs - Or Free Us to Do Better Work?

A conversation about work, purpose, capitalism, and the hopeful path through the AI transition.

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What This Substack Is About

So you can decide if it is right for you.

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The Inverse Prompt

If we wanted to lift an entire generation with AI, what would we do?

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Tax Savings Series - Installment #2

The Augusta Rule: Business Deduction & Tax-Free Rental Income

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The Engine of Wealth

Why Income Is the First Lever of Financial Freedom (and How Earn, Save, Invest - and Build - Create Exponential Wealth)

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Adversity is an Advantage

Why the Worst Parts of Your Story Might Be Your Greatest Asset

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Tax Savings Series - Installment #1

Real Estate + Bonus Depreciation

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Write the Letter. Change the Decade.

The Most Powerful Exercise I’ve Ever Done for Designing My Life

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How I Turned $267 Into $45,000,000

What 7 Years of Ownership Taught Me About the Fastest Path to Life-Changing Wealth — And the 9 Decisions That Made It Possible

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Tax Strategy Is a Guaranteed Return

Investing is probabilistic. Tax savings aren’t. The mindset shift that’s saved me millions - even in California.

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You Can’t Cut Your Way to Riches

But You Can Earn Your Way There

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When Motivation Wanes, Discipline Reigns

Discipline isn’t willpower - it’s tools, rules, and protocols that remove friction and override your feelings.

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Me, Myself, & AI

The New "3-Person" Company

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The Art of Spending Money

The skill too many people never develop

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Holy Guacamole

The Sneaky (and Indirect) Entrepreneurship Lessons Hidden in an Avocado Stand

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Prepare Like a Pessimist so You Can Live and Invest Like an Optimist

Bad things happen - but like markets, life still trends up over time.

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The Only Fortune You Have To Spend Down To Zero

You can always make more money - but you can’t make more time. Here’s how I stay intentional with mine.

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Send the Elevator Back Down

Every day is an opportunity to change someone’s life forever – and today is your day.

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Trade the Money for the Memories

A framework for people like you and me who love efficiency, hate waste, and still struggle to pull the trigger on the life we earned.

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Net Worth Conversion Rate

Your Wealth-Building Efficiency Metric

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How I Think About Money

My Personal “Money Operating System”

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A Paid-Off Mortgage as a Bond Substitute

And a Bond You Can Live In

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Live Like Most Won’t (For a Season)

If you’ll do what most won’t now, you can live how most can’t later.

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The Reality of the “Overnight Success”

It’s 10 Years in the Making

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Extreme Frugality Is For The Birds

Relative Frugality Is The Shiznit!

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Your Roadmap To Financial Independence

5 Major Milestones (Plus Financial Freedom as a BONUS milestone)

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On The Shortness of Time

You have more than you think, but it will never feel like enough

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Concentrate to Build Wealth. Diversify to Preserve It.

You get rich by concentrating your time, capital, and energy on a single mission.

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The Impact of Your Savings Rate

How it determines the time to reach Financial Freedom

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Ambitiously Lazy

The art of optimizing life for maximum results with minimal wasted effort.

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First Believer

Every day is an opportunity to change someone’s life forever—and today is your day.

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The Law of 50%

Save 50% and spend the remaining 50% guilt-free!

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It Only Takes a Few Good Decisions to Become Rich

Don’t overcomplicate it. It’s five key decisions you practice, not secrets you chase.

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Don’t Get So Consumed Building Wealth That You Forget To Build A Life

A quick reminder to look up from the grind.

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Buffalo Instincts

Running into the storm is the fastest way through it

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The Pro-Leisure Life

I thought I wasn’t built for it but turns out I was wrong

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The Highest Form of Civilization

Is found when we focus on what unifies us

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What I’ve Learned Over My 39 Years on This Earth

As I reflect on nearly four decades of life

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100 Days Until My “First Retirement” at 39 Years Old

Breaking free from the golden handcuffs!

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Stealth Wealth

The practice of living below the radar while quietly building and enjoying financial freedom

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Howard Marks Teaches Us: How to Think About Risk

Risk is the invisible force shaping your outcomes

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The Three Types of Makers

I’m Not Ashamed of Being a Copycat

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Getting Paid to Be Patient: One of My Favorite Income Strategies

Free money to wait and buy assets below market price

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My 10 Year Letters

From 2012, 2019, and 2023

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