Wayfair Founders Cash Out Again After Rally, Retail Traders Feel Stock Looks Too Pricey

Wayfair Inc. shares fell 0.8% in extended trading on Wednesday, following the company's disclosure of another sale of shares by its founders, which kept retail traders bearish about the stock's near-term prospects.

CEO Niraj Shah and Steven Conine, chairman of the company's board, each sold 85,000 Wayfair shares, pocketing $7.4 million apiece, according to Form 4 filings with the Securities and Exchange Commission after the market closed on Wednesday.

The trades are part of their insider trading plan adopted in August last year. Notably, the executives have been selling shares consistently amid an incredible rally in Wayfair's stock.

Shares of the online furnishing store have gained approximately 230% since its 2025 low on Apr. 3.

The gains are driven by cost cuts at the company, including the elimination of 730 jobs as part of its exit from the German market earlier this year, as well as improving financial performance.

Shah has sold shares each month since November 2024, including an over $24 million cumulative stock sale last month.

On Stocktwits, the retail sentiment for Wayfair remained in the 'bearish' zone, unchanged from the prior day.

"$W seems way too expensive right now. Wish I had bought in the low 70s a couple weeks ago... Will look for a nice dip to enter," posted one user.

Last week, Jefferies raised its price to $102 from $91, while maintaining its 'Buy' rating, after the company disclosed a new awards package for Shah. 

The CEO's potential compensation over a multi-year time horizon increases the likelihood of management consistency and highlights the "significant opportunity" the board sees for creating realizable shareholder value, the analyst told investors in a research note.

Year-to-date, Wayfair shares are up 87%.

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