Last April, I sat in my accountant's office at 9:30 AM on April 14th — literally the day before the IRA contribution deadline — and watched her face do th...
Last April, I sat in my accountant's office while she explained the backdoor Roth IRA to me. Fifteen minutes. Four hundred dollars. And honestly? She could have...
I will never forget the look on my dad's face at Thanksgiving 2023 when he realized he had been contributing to his traditional IRA for three years without actu...
My sister called me on a Tuesday evening in February, the kind of call that starts with "I have a quick question" and ends forty-five minutes later with both of...
My Dad Put Everything in His 401k for 30 Years — Then His Financial Advisor Said He Should Have Split It With an IRA Last Thanksgiving, my dad dropped a bom...
A Substack Exposé Just Blew Up the Entire Compliance Industry — And If You Have Invested in Any Startup That Claims SOC 2, You Need to Read This I was halfw...
My friend Rachel texted me at 9:47 PM on Sunday night. No greeting, no context, just a Reuters link and the words "please tell me this is a joke." It was not a ...
This article is for informational and educational purposes only and does not constitute financial advice. Consult a licensed financial advisor before making inv...
My buddy Tom, who sells commercial insurance out of a cramped office in downtown Tampa, called me at 7:15 AM on a Wednesday. That is never good. Tom does not ca...
A Journalist Received Death Threats Over a News Story — Because Gamblers Had Money on the Outcome Last Tuesday night, around 11:20 PM, I was scrolling throug...
When my neighbor Diane knocked on my door last Tuesday evening — wine in one hand, laptop in the other — I assumed she wanted help connecting to her new pri...
My friend Carla applied for a marketing manager position at a mid-sized SaaS company last month. She's got eight years of experience, a portfolio that speaks fo...
A post hit the top of Hacker News yesterday with the title “Create value for others and don’t worry about the returns.” It generated over 300 ...
It is March 11th. Tax Day — April 15th, 2026 — is exactly five weeks from today. If you have not filed yet, you are not alone. According to the IRS, roughly...
On January 2nd, 2026, I did something that my friends called "unhinged" and my financial advisor called "actually kind of brilliant": I cut up my debit card, de...
Nobody teaches you how to do taxes. Not in high school. Not in college. You just turn 22, get a W-2, and suddenly you are expected to figure out a system that c...
I remember staring at my bank account with exactly $127 to my name, thinking investing was something only people in suits with six-figure salaries did. That was...
Every personal finance article about Roth vs Traditional IRA ends the same way: "It depends on your situation." Which is technically true and practically useles...
Every personal finance article recommends the 50/30/20 rule. Spend 50% on needs, 30% on wants, 20% on savings. It is simple, clean, and completely disconnected ...
January 2nd, I opened my bank statement and stared at a number that made my stomach drop. Not because I was broke — because I genuinely could not explain wher...