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Insider Sell: Upstart Holdings Inc's Chief Legal Officer Scott Darling Sells 4,206 Shares

Scott Darling, the Chief Legal Officer of Upstart Holdings Inc (NASDAQ:UPST), has recently sold 4,206 shares of the company's stock. The transaction took place on December 6, 2023, signaling a notable insider move within the financial technology sector. This sale has caught the attention of investors and market analysts, as insider transactions can often provide valuable insights into a company's prospects and the sentiment of its top executives.

Who is Scott Darling?

Scott Darling is known for his role as the Chief Legal Officer at Upstart Holdings Inc. In his position, Darling is responsible for overseeing the legal aspects of the company's operations, ensuring compliance with regulatory requirements, and managing legal risks. His actions, particularly in the sale or purchase of company stock, are closely watched as they may reflect his confidence in the company's future performance.

About Upstart Holdings Inc

Upstart Holdings Inc is a company that operates in the financial technology sector, leveraging artificial intelligence to improve access to affordable credit while reducing the risks and costs of lending for its bank partners. The company's platform uses sophisticated machine learning models to more accurately identify risk, enabling a more nuanced assessment of borrowers than traditional credit scores allow. This innovative approach has positioned Upstart as a disruptor in the lending industry, aiming to make credit more available to consumers and small businesses.

Analysis of Insider Buy/Sell and Relationship with Stock Price

Insider transactions, such as the recent sale by Scott Darling, can be a double-edged sword when it comes to interpreting their impact on a company's stock price. On one hand, insiders may sell shares for various personal reasons that do not necessarily reflect their outlook on the company's future, such as diversifying their investments or financing personal expenditures. On the other hand, a sale by a high-ranking insider like the Chief Legal Officer could be perceived as a lack of confidence in the company's prospects, potentially leading to negative investor sentiment.

Over the past year, Scott Darling has sold a total of 27,667 shares and has not made any purchases. This one-sided activity could suggest that Darling is taking a cautious stance towards the company's valuation or future growth. However, without additional context, it is difficult to draw definitive conclusions from these actions alone.

When examining the broader insider transaction history for Upstart Holdings Inc, there has been a significant imbalance with only 1 insider buy compared to 70 insider sells over the past year. This trend might raise questions among investors about the internal confidence level among Upstart's executives and board members.

On the day of the insider's recent sale, shares of Upstart Holdings Inc were trading at $36.19, giving the company a market cap of $3.140 billion. This valuation places the company in a substantial market position within the fintech industry.

According to the GF Value, with a price of $36.19 and a GuruFocus Value of $29.90, Upstart Holdings Inc has a price-to-GF-Value ratio of 1.21, indicating that the stock is modestly overvalued. The GF Value is a proprietary intrinsic value estimate from GuruFocus, which takes into account historical trading multiples, a GuruFocus adjustment factor based on past returns and growth, and future business performance estimates from analysts.

The modest overvaluation could be a contributing factor to why insiders like Scott Darling are choosing to sell shares. If insiders believe that the stock's current price exceeds its intrinsic value, they may decide that it is an opportune time to realize gains.

Insider Sell: Upstart Holdings Inc's Chief Legal Officer Scott Darling Sells 4,206 Shares
Insider Sell: Upstart Holdings Inc's Chief Legal Officer Scott Darling Sells 4,206 Shares

The insider trend image above provides a visual representation of the selling and buying patterns of insiders at Upstart Holdings Inc. The predominance of selling transactions could be indicative of a consensus among insiders that the stock's price may not sustain its current levels or that growth prospects may be limited in the near term.

Insider Sell: Upstart Holdings Inc's Chief Legal Officer Scott Darling Sells 4,206 Shares
Insider Sell: Upstart Holdings Inc's Chief Legal Officer Scott Darling Sells 4,206 Shares

The GF Value image further illustrates the stock's valuation in relation to its estimated intrinsic value. The modest overvaluation highlighted by the price-to-GF-Value ratio is clear, and investors may want to consider this information when making investment decisions regarding Upstart Holdings Inc.


The recent insider sale by Scott Darling at Upstart Holdings Inc is a significant event that warrants attention from investors. While the reasons behind the sale may vary, the overall trend of insider transactions at the company suggests a cautious approach to the stock's current valuation. As Upstart Holdings Inc continues to navigate the competitive fintech landscape, investors should closely monitor insider activity and valuation metrics like the GF Value to inform their investment strategies.

It is important to note that insider transactions are just one piece of the puzzle when evaluating a stock's potential. A comprehensive analysis should also consider the company's financial health, growth prospects, competitive position, and broader market conditions. As always, investors are encouraged to conduct their own due diligence and consult with financial advisors before making investment decisions.

This article, generated by GuruFocus, is designed to provide general insights and is not tailored financial advice. Our commentary is rooted in historical data and analyst projections, utilizing an impartial methodology, and is not intended to serve as specific investment guidance. It does not formulate a recommendation to purchase or divest any stock and does not consider individual investment objectives or financial circumstances. Our objective is to deliver long-term, fundamental data-driven analysis. Be aware that our analysis might not incorporate the most recent, price-sensitive company announcements or qualitative information. GuruFocus holds no position in the stocks mentioned herein.

This article first appeared on GuruFocus.