Markets · Technology · Boston

Aaron Pressman

Finding untold stories in financial markets and the technology sector.

Innovative journalist with extensive experience distilling complex details into compelling stories, drawing connections and uncovering trends in technology and finance. A quick writer with the ability to produce rapid analysis on breaking news, as well as spend weeks drilling into a topic to produce award-winning feature stories. Also a newsletter curator renowned for summarizing the news with wit and verve. Two-time SABEW Best in Business winner.

Selected Work

  1. 01

    Castlight Health: Most overpriced IPO of the century

    AnalysisYahoo Finance · 2014

    Back in 2014, the bubble was in SaaS stocks and this was one of the worst. The stock never traded near its first-day price again and the company was ultimately acquired for $2 a share.

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  2. 02

    Squeezed: Why the middle class is disappearing in Massachusetts

    SeriesThe Boston Globe · 2025–2026

    Co-authored a multi-part series on the unwinding of middle-class economics in Massachusetts. Awarded the 2026 SABEW Best in Business prize for economics reporting.

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  3. 03

    Time to start calling IBM ‘Medium Blue’

    AnalysisYahoo Finance · 2015

    After IBM’s fourteenth consecutive quarter of falling revenue, it was long past its glory days as one of the leading tech companies in the world. Even with a successful turnaround, the company emerging from the transition would be structurally smaller, not restored.

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  4. 04

    Why Intel is betting its chips on microprocessor mastermind Jim Keller

    ProfileFortune · 2020

    A long-form profile of the design legend whose work shaped processors at Apple, AMD, and Tesla. What happened when he tried to revive Intel.

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  5. 05

    The investment ‘albatross’ at UBS

    InvestigationBusinessweek · 2008

    How the Swiss bank sold tens of billions of dollars in auction-rate securities to clients as “cash equivalents,” until the market froze and the money was stuck.

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  6. 06

    Buy Amazon — Kindle is the iPod of books

    AnalysisBusinessweek · 2007

    A buy call on Amazon when the Kindle came out, made against near-uniform derision and argued from content pricing and economics rather than gadget reviews.

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  7. 07

    Can AT&T Retrain 100,000 People?

    FeatureFortune · 2017

    Inside one of the largest workforce-transformation projects in American corporate history. Awarded the 2017 SABEW Best in Business prize.

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  8. 08

    Inside T-Mobile’s Big, Brash Comeback

    FeatureFortune · 2018

    How a third-place wireless carrier broke its industry’s unwritten rules through audacity, consumer obsession, and a theatrical brand voice.

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A career in business journalism.

I started in New York in covering mergers and IPOs at Investment Dealers Digest, then built a beat on over-the-counter derivatives, first municipal, at The Bond Buyer, then corporate, for Reuters. I moved to Washington in the mid-1990s to cover banking regulators through the Glass-Steagall debates, and carved out an internet-policy beat at the FCC in the wake of the Telecommunications Act.

Back following the markets from Boston after 9/11, I was lead mutual-fund reporter at Bloomberg News through the market-timing scandal, wrote a daily contrarian markets column for TheStreet.com, and led the mutual-fund team at Reuters. In between, I spent five years at Businessweek on investigations into credit scores, auction-rate securities, and fee-based brokerage accounts, and wrote the Investing Insights blog.

Since 2013, I have covered technology for financial and business audiences at Yahoo Finance, at Fortune as a senior writer where I curated and wrote Data Sheet, the daily tech newsletter, and now at The Boston Globe.

I’m a two-time SABEW Best in Business award winner (2017, 2026), a Columbia graduate, and a longtime resident of Needham, Massachusetts, where I served eight years on the elected School Committee, including a term as chair.

Awards & press.

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