Long Upwork

The market completely threw Upwork away. The narrative was simple: AI is going to kill the freelancing business, so the company is dead. The stock was driven down to a level that made no sense. But I looked at the actual business and realized the narrative was wrong. It was actually the opposite.

Upwork had a clean balance sheet, was actively buying back shares, and margins were improving. AI wasn't destroying the business, it was helping it. This was a great company trading at an incredibly cheap valuation because the market was too focused on a fear-driven story to look at the fundamentals.

I was buying both shares and options as the thesis developed, and the stock ultimately rallied roughly 70%. I took profits on the options on the way up, capturing the convexity while keeping exposure to the long-term setup. Two quarters ago, I started to notice thesis-breaking issues, and the technicals no longer looked favorable, so I exited the remainder of the shares.