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Hello, Fintech Friends!

During its most recent ‘On The Block’ conversation aired August 14, the CFO of Block*, Amrita Ahuja, was posed the following question: “What do you think Block hasn’t done well enough…to earn a sustained re-rating on the stock?”

For shareholders, the persistent discount between Block and its closest peers may be among the most frustrating aspects of the story, especially considering the perception that Block’s execution has improved and growth is moving to a sustainably higher level. Before I attempt to hypothesize why the discount exists, let’s take a closer look at the numbers first.

On an expected calendar 2026 gross profit of $12.51 billion, Block’s enterprise value of approximately $50 billion represents 4.0x gross profit. On a similar measure and based off of consensus estimates (per Koyfin), Chime trades at 5.6x, Affirm at 11.5x, and Toast at 9.5x. Big premiums certainly. From a growth perspective, Block is expected to increase gross profit by 21% during calendar 2026, Chime by 27%, Affirm by 29%, and Toast by 23%. Yes, growth for peers is expected to be faster, but not materially so. Now, on to the why.

The first, and potentially most obvious reason Block trades at a discount is because Block is an amalgamation of three separately scaled businesses: a P2P and digital banking app (Cash App), an integrated operating platform for SMBs (Square), and a global BNPL provider (Afterpay). If a conglomerate discount exists in fintech, Block has certainly been saddled with one. Now, in their defense, traditional conglomerates happen primarily through M&A. In the case of Block, with the exception of Afterpay, the vast majority of their products have been internally developed, invested behind, and scaled.

Other potential factors for the discount include Block’s credit exposure and lack of transparency.

On credit, based on my estimates, I believe approximately one-third of Block’s gross profit comes from lending-based activities, including Square capital, BNPL, and Cash App Borrow. Even though that may seem high, the credit contribution for Toast and Chime is approximately 10% and 20%, respectively. Further, Affirm generates nearly all of their gross profit from lending, including a significant amount from longer-duration, higher-interest installment loans.

Finally, where I believe Block can do better is transparency. Where Chime, Affirm and Toast provide a thorough accounting of their key products’ performance, including volume, revenue, and loss rates, Block offers incomplete and shifting disclosures that make assessing underlying performance a bit of a guessing game from quarter-to-quarter.

Block’s ability to close its valuation gap will be one of the more interesting stories to watch over time, in my opinion. While I believe there are actions they could take to help themselves, there does not appear to be a single ‘silver bullet’ outside of sustained execution, which is likely to be measured in years, not quarters.

* As of August 26, 2026, I am long Block

Bob Hammel

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Charts Corner

Data source: Yahoo Finance

Data source: Yahoo Finance

Data source: Yahoo Finance

Worth Watching

Intuit Pivots to New Customer Acquisition

In conjunction with its fiscal Q4 2026 earnings, Intuit* previewed a change to its strategy moving forward, shifting from a primary focus on maximizing revenue from existing customers through adoption of features like assisted tax and mid-market offerings, to acquiring more new-to-the-platform customers across TurboTax and QuickBooks, filling the funnel for future cross and up-sells. The impact of the pivot will be lower revenue growth over the mid-term as the company utilizes pricing as a tool to gain more customers at the low-end. For the upcoming fiscal year, Intuit expects revenue to grow 9-10%, below fiscal 2026’s growth rate of 14%. Of course, the question moving forward for Intuit will be whether slower new customer growth was due to a lack of focus, or because of the emergence of AI-enabled competitors, a more troubling development for the company.

* As of August 26, 2026, I am long Intuit   

Jack Henry Delivers Strong Fiscal 2026 Results          

Jack Henry reported strong results for its recently concluded fiscal 2026: organic revenue increased 7%, underlying margins expanded approximately 90-bps, and the company converted all of its GAAP net income to free cash flow, marking the second consecutive year of improved conversion. While Jack Henry is benefitting from the disruption at one of its primary competitors, Fiserv, it indicated it is gaining share from all competitors in bank technology, enabling its significant sales momentum, which is expected to continue into fiscal 2027, where it expects to win 58-65 new core deals, up from 58 in fiscal 2026, and 51 during fiscal 2025. In addition to an increased number of wins, Jack Henry is signing larger banks and credit unions and selling them more solutions upfront, including digital banking and card issuing.

Stripe Buys OpenRouter

Last week, Stripe announced it has agreed to acquire OpenRouter, a single gateway for developers to access different LLMs in order to maximize performance while managing token costs. Although not disclosed, the reported price tag for the transaction is believed to be in the $7.5 billion range, a significant increase from OpenRouter’s $1.3 billion valuation in May of 2026. While Stripe handles payments and usage-based billing for many of the leading AI-native companies, its purchase of OpenRouter signals an even greater push into the category and its intention to be an operating platform for the AI economy. It is not clear how this purchase potentially impacts Stripe’s pursuit of PayPal, which appears to be ongoing.  

Multiples

Data source: Yahoo Finance

Data source: Yahoo Finance

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