Block's $29 billion all-stock acquisition of Afterpay, completed in January 2022, was completed at peak fintech valuations immediately before a sharp interest rate rise that compressed buy now pay later economics across the industry. The resulting $2.2 billion in goodwill impairment charges, combined with Block's stock price decline from $270 to approximately $60, made the Afterpay acquisition the most costly capital allocation decision in Block's history. The strategic rationale — integrating BNPL into both Square and Cash App to accelerate international expansion — was sound, but the acquisition price assumed a competitive and interest rate environment that did not persist, and a lower acquisition price or delayed timing would have preserved significant shareholder value.

Block's $297 million acquisition of a majority stake in TIDAL, the music streaming service, has not produced visible strategic value relative to Block's core financial services mission. TIDAL's competitive position against Spotify and Apple Music has not improved under Block's ownership, the artist-fan financial relationship model that Dorsey articulated as the acquisition rationale has not been commercially implemented at scale, and the management attention and capital consumed by TIDAL compete with higher-return investment opportunities in Square and Cash App. The acquisition has been a recurring investor relations burden that management has not resolved through either significant product innovation or divestiture.

Jack Dorsey's simultaneous tenure as CEO of both Square and Twitter from 2015 to 2021 was a governance arrangement that most institutional investors and corporate governance advisors considered inconsistent with the management focus required to lead either company effectively through competitive challenges. During this period, Square's product velocity in the mid-market segment was slower than the opportunity warranted, and several competitive windows — merchant banking, mid-market software expansion — were not fully exploited. Dorsey's full-time focus on Block since November 2021 has been credited with accelerating strategic initiatives, implicitly confirming that the dual-CEO structure was suboptimal for Block's development during a critical competitive period.

Square's 2012 partnership with Starbucks, while providing valuable brand credibility, was financially unfavorable to Square: Square processed Starbucks payments at a rate that did not cover Square's full interchange and processing costs, effectively subsidizing the partnership to gain the enterprise reference customer. Starbucks subsequently moved its payment processing to Heartland Payment Systems in 2015, removing the volume contribution while the below-cost processing terms had persisted. The partnership demonstrated the difficulty of scaling enterprise payment processing on the pricing model designed for small merchants, and its below-cost economics should have been renegotiated before the volume reached the scale that made the losses material.