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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 (25)

Page 1
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.

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.

Titan funding and RFA announcementCompany announcementExcerpt

Announced August 12, 2025, from New York. Titan, an AI holding company incubated by General Catalyst, announced $74 million in funding led by General Catalyst and, in the same release, its acquisition of Richard Fleischman & Associates (RFA), a New York-based managed service provider with roughly 250 employees serving more than 400 financial services clients across multiple countries. RFA becomes Titan's first MSP platform, into which Titan layers its augmented AI stack. The stated thesis is that traditional MSPs are constrained by legacy tooling and manual, ticket-based workflows, and that agentic AI can automate routine support, predict failures, and free technicians to act as strategic advisers rather than reactive support. Co-founders Saurin Patel and David Heffernan said Titan intends to acquire additional IT services firms. Yohan Kim is chief executive of RFA; Marc Bhargava, managing director at General Catalyst, commented on the investment. The deal was one of several executions of General Catalyst's AI-enabled roll-up program, for which the firm allocated $1.5 billion beginning in late 2023.