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Reading Room

Read the arguments shaping this field: original letters and essays, independent reporting, interviews, and podcasts. Every item says whether the text is available here or should be read at its publisher.

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All reading (42)

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The PioneersEssay or blogExcerpt
Thrive Holdings, individual author not shown · Thrive Holdings

Profiles RRBB practitioners including Rob Quick, Dave Roth, and Susan DiPaolo. Recounts a prior software initiative that failed because document-scanning work was not adopted.

Long HumansEssay or blogExcerpt
Thrive Holdings · Thrive Holdings

Argues that relationships and professional judgment become more valuable as routine work gets cheaper. Makes permanent ownership, practitioner ownership, and organizational change central.

Aravind Srinivasan; Samay Shamdasani; Arthur Fernandes Araujo; John de Wasseige · OpenAI / Thrive Holdings

Describes a practitioner-feedback and evaluation loop for Tax AI. Reports a 7,000-return pilot, roughly one-third less preparation time, and about 50% greater throughput.

The Baldwin Group

Announced May 4, 2026, from Tampa. The Baldwin Group (NASDAQ: BWIN), an independent insurance brokerage and advisory firm, announced an expanded enterprise relationship with Anthropic to deploy Claude firm-wide. Baldwin will integrate Claude across its business segments and functional groups, giving advisors, client experience staff, and operational leaders an enterprise-grade platform intended to improve productivity, speed decision-making, and support end-to-end workflows. The agreement followed several months of active deployment in targeted parts of the business, which Baldwin said produced measurable gains in the quality of client-facing insights, productivity, and workflow efficiency. Chief executive Trevor Baldwin framed the tool as augmenting rather than replacing professional judgment, describing the core skill in the industry as synthesizing complex risk and anticipating unasked client questions. The release also emphasized governance, training, and cross-functional collaboration as part of Baldwin's approach to AI adoption. Baldwin was subsequently the target of a take-private agreement by a consortium led by Michael Dell's DFO Management and Sequence Holdings.

Shield raises $100M from ThriveCompany announcementExcerpt

Announced February 2, 2026, from New York. Shield Technology Partners raised $100 million from Thrive Holdings to fund product development and further acquisitions across its national IT services platform. Shield reported surpassing $100 million in annual revenue in 2025 and partnering with nine IT services companies across the US serving more than 1,500 customers in sectors including construction, energy, and healthcare; it had majority stakes in four MSPs at its June 2025 launch, which carried more than $100 million in initial capital. Part of the investment supports Shield's engineering team, which works alongside OpenAI researchers to build and embed AI products for IT engineers. Two internal products were named: Sentinel, which monitors and triages customer tickets and routes them by engineer, timing, and priority, and Spectre, which helps engineers orchestrate multiple agents to resolve requests. Jim Siders is chief executive of Shield; Anuj Mehndiratta of the Thrive Holdings founding team commented, as did Alexander Saca, chief executive of partner company IronOrbit. Shield was formed as a collaboration between Thrive Holdings and ZBS Partners, pairing Thrive's technical capability with ZBS's approach to founder-led businesses.