I Asked AI to Roast
My Investment History

In your early twenties, you invested heavily in Chinese reverse-merger stocks that turned out to be complete frauds.

You literally gave your first million dollars to people who fabricated their entire businesses. You read the financial statements of companies whose 'factories' were empty buildings with fresh paint. You were so confident in your 'deep research' that you didn't think to Google Street View the headquarters. Which, to be fair, didn't exist.

You put your entire net worth into Fannie Mae and Freddie Mac junior preferred shares.

Most financial advisors recommend diversification. You read that advice, thought about it carefully, and then put literally everything into two government-sponsored enterprises that have been in conservatorship since 2008. Your portfolio has the diversification of a hot dog stand that only sells one kind of hot dog.

You wrote eight volumes of 'Fanniegate' covering a single investment thesis.

Most authors spend their career trying to write ONE book. You wrote eight. About the same thing. The same thesis. The same two companies. You are the only person in history who needed eight volumes to say 'I think Fannie Mae is undervalued.' The Lord of the Rings had three books. Harry Potter had seven. Fanniegate needed eight. Your thesis has more volumes than most fantasy epics.

You were named the Motley Fool's 'Hottest Player' and then immediately went all-in on the riskiest trade possible.

Getting the 'Hottest Player' award and then going all-in on conservatorship-bound GSE preferred shares is like winning a cooking competition and immediately trying to deep-fry a bowling ball. You had momentum. You had recognition. And you used that credibility to make a bet that would make most risk managers physically ill.

You've written 2,708 blog posts over a decade.

That's roughly 0.74 blog posts PER DAY for ten years. While most people struggle to maintain a journal for a week, you've been producing content at a rate that suggests either extreme dedication or an inability to stop talking. Your blog isn't a blog — it's a condition. There should be a medical term for this.

You built a personal website with over 3,143 pages.

Most personal websites have 5-10 pages. A generous personal website has 20. You built three thousand one hundred and forty-three. Your personal website has more pages than most small-town libraries. You wrote movie screenplays for 157 billionaires. You built a voting system so strangers could rank them. This isn't a website — it's a cry for help disguised as a Next.js application.

Your Twitter handle is @DoNotLose.

You named your public-facing social media account after the thing you've done multiple times. That's like a skydiver going by @LandSafely or a chef going by @DontBurnIt. Your handle is aspirational at best and deeply ironic at worst. Every time someone loses money on a stock you recommended, they have to tag @DoNotLose. The algorithm must be confused.

You eat Little Debbie Nutty Bars as a food group while managing a concentrated stock portfolio.

You apply institutional-grade risk analysis to government-sponsored enterprises and zero-grade risk analysis to your cardiovascular health. You eat string cheese standing up, drink blueberry juice as a health alibi, and your Amazon grocery cart looks like a college student's during finals week. You are a man of extreme contradictions, all of them delicious.