The Win Wall

Started investing as a teenager. By 24, the portfolio crossed seven figures. I had no idea what was coming next (see: Chinese stock frauds), but that moment proved to me that focused, independent thinking works.

I found Conseco as a college kid — thrifty, never bought anything, saved every dollar, worked as hard as I could. The thesis played out beautifully. But instead of loading the boat on a conviction bet, I undersized the position. The win made me money, but the real lesson was worth more: when you know you're right, bet accordingly. Position sizing is everything.

After the Chinese stock fraud losses, I found Yellow Media. Deep value, misunderstood, and massively discounted. The return was the proof I needed that my process worked — even after catastrophic failure.

Over a decade of investment analysis, market commentary, and Fanniegate coverage. Built a readership that led to Jim Cramer personally emailing me to say 'Man, this is good.'

Back when Motley Fool had a competitive stock-picking platform, I was ranked the hottest player. Then I bet everything on Fannie Mae. Which is very on-brand.

A full Salesforce managed package — 85 production releases in 8 months, 90%+ test coverage. Built at Cloud Nimbus LLC. The product that proved I could ship enterprise software solo.

The @DoNotLose account grew into a real audience. People show up for the Fanniegate analysis, the self-deprecating humor, and the occasional stomp rocket update.

281,115 pages indexed by Google. The security analysis PDF page alone pulls 2,100 clicks per month. Organic search actually works when you build enough quality content.

Look, not everything has to be about money. Sometimes a win is just hitting a ceiling shot at 2 AM. Muscle memory is real.

The biggest win on this list. My daughter launches stomp rockets with me, plays with the coding robot I 'bought for her,' and makes every other win on this list feel small by comparison.

Industrial Engineering undergrad and MBA from Purdue. The engineering degree taught me systems thinking. The MBA taught me that most of what they teach in MBA programs is wrong. Both were valuable.