The Most Powerful Tax Break in America Gets an Upgrade: QSBS in 2025

The Most Powerful Tax Break in America Gets an Upgrade: QSBS in 2025

The One, Big Beautiful Bill just upgraded QSBS: here's what every startup founder, employee and investor should know.

Jul 30, 2025
How to Use Trump Accounts to Make Your Kids Tax-Free Millionaires

How to Use Trump Accounts to Make Your Kids Tax-Free Millionaires

See how high earners can arbitrage these to set their children up with 8-figures in retirement

Jul 24, 2025
Why I Stopped Investing in Index Funds

Why I Stopped Investing in Index Funds

Vanguard funds are mostly dead for high earners, learn what I do instead.

Jul 17, 2025
What One Big Beautiful Bill Means for Business Owners and High Earners

What One Big Beautiful Bill Means for Business Owners and High Earners

Learn what the most important piece of new tax legislation in almost a decade means for you

Jul 8, 2025
The Anatomy of a Hundred Million Dollar Roth IRA

The Anatomy of a Hundred Million Dollar Roth IRA

How the wealthiest Americans are exploiting a retirement account intended for the middle class

Jun 10, 2025
How to Understand and Negotiate Your Startup Equity

How to Understand and Negotiate Your Startup Equity

Read this article before you ever accept a job offer at a startup with equity again

Apr 20, 2025
How to Think About Raising Venture Capital for your Startup

How to Think About Raising Venture Capital for your Startup

My best fundraising advice written from founder to founder

Apr 6, 2025
I Bought a (Tiny) Piece of a Cricket Team!

I Bought a (Tiny) Piece of a Cricket Team!

Announcing my most fun investment to date

Mar 22, 2025
What's Inside my Personal Finance "Stack"

What's Inside my Personal Finance "Stack"

Every single tool and service I use for investing, banking, credit cards, travel and taxes

Mar 18, 2025
7 Things I Wish I Knew About Money in my 20s

7 Things I Wish I Knew About Money in my 20s

A beginner's guide to personal finance that I wish I had when I was 21

Mar 2, 2025
6 Hard-Won Lessons from Selling my Startup

6 Hard-Won Lessons from Selling my Startup

How to navigate the process of selling your business and retain your sanity

Feb 19, 2025
How to Grow on Twitter (2025 Edition)

How to Grow on Twitter (2025 Edition)

Sharing the playbook I used to grow my X account to 100K+ followers and tens of millions of dollars in business deals

Feb 10, 2025
The $1M ARR Growth Playbook

The $1M ARR Growth Playbook

Breaking down exactly how we scaled my last startup Teachable to $1M in ARR

Jan 26, 2025
The Most Powerful Tax Break in America

The Most Powerful Tax Break in America

Why every startup founder, employee and investor should understand QSBS

Jan 19, 2025
How To (Not) Invest Life Changing Money

How To (Not) Invest Life Changing Money

A personal story on how I invested my money after selling my startup

Jan 12, 2025

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