Pressman started his career in New York City working at Wall Street publications Investment Dealers Digest and The Bond Buyer. He moved to Washington, D.C. while working for Reuters in the mid-1990s, where he covered regulation of banking and technology before carving out a new Internet policy beat. During the Internet magazine bubble, he worked at The Industry Standard and covered the White House and the Federal Communications Commission.

Moving to Boston in 2001, Pressman freelanced at a variety of publications including Wired, Boston Magazine and the Christian Science Monitor. He then worked as a full-time staffer at Bloomberg News, TheStreet.com and Businessweek, where he wrote the award-winning “Investing Insights” blog, before returning to Reuters in 2009. He left for Yahoo Finance in 2013, before joining Fortune in 2016.

He also maintained a personal tech commentary and gadget review blog, GravitationalPull.net, from 2005 through 2013.

How Facebook plans to dominate virtual reality in real life, Yahoo Finance, March 4, 2016

Congress likely to side with Apple in iPhone unlocking debate, Yahoo Finance, March 1, 2016

Time to start calling IBM 'Medium Blue’, Yahoo Finance, October 21, 2015

IBM banned Uber for employees, but quickly reversed course, Yahoo Finance, June 3, 2015

Apple Pay sides with credit card industry over consumer interests, Yahoo Finance, October 29, 2014

Castlight Health: Most overpriced IPO of the century, Yahoo Finance, March 14, 2014 (stock dropped from $40 to $4 over the next year)

Anti-hacking law questioned after death of Internet activist, Reuters, January 15, 2013

Great artists steal, tablet edition, Reuters, December 2, 2011

Special Report: What did you do in the ETF war, daddy?, Reuters, December 3, 2010

Amid the Gulf crisis, Wall Street touted BP stock, Reuters, June 18, 2010

Special Report: Divorce American style for French bank, bond star, Reuters, January 10, 2010

Bets on the Bankrupt, Businessweek, June 22, 2009 cover date

The Investment 'Albatross' At UBS, Businessweek, August 11, 2008 cover date

Buy Amazon - Kindle is the iPod of books, Businessweek, November 19, 2007 blog entry

Music CD, I'm just not that in to you, Businessweek, March 21, 2007 blog entry

Fished Out, a Businessweek special report on the future of commercial fishing, Sept. 4, 2006 cover issue date

Drunk on Ethanol, Businessweek, May 9, 2006

The dangers of quick thinking - review of Malcolm Gladwell’s Blink, TheStreet.com, Jan. 22, 2005

Inspecting housing's foundation for flaws, TheStreet.com, Sept. 16, 2004

Googling the Future With Ghosts of IPOs Past, TheStreet.com, July 27, 2004

America's Stock-Fund Owners Pay Twice the Fees of Institutions, Bloomberg News, Nov. 17, 2003

Arizona Firm Cited by Spitzer Had Run-Ins With Bank Regulators, Bloomberg News, Sept. 22, 2003

(Regulators ordered the firm dissolved and charged 3 executives in November 2003)

Putnam Customers Flee After Bad Tech Bets Pummel Returns, Bloomberg News, June 23, 2003

(Putnam ousted CEO Lasser five months later)

Franklin's Succession Plans May Overshadow Earnings, Bloomberg News, April 23, 2003

(Franklin named co-CEO's two quarters later)

Mutual Suspicion, Boston Magazine, October 2002

Consumers in crossfire of labels' war on piracy, Christian Science Monitor, March 4, 2002

Playing a New Tune, CNet/Fortune special issue, Winter, 2001

Gridlock: California Could Be Just the Beginning, The Industry Standard, June 25, 2001

Tech's White House Connection, The Industry Standard, April 2, 2001

Legal Storm Brewing Over Microsoft's Hailstorm, The Industry Standard, March 19, 2001

Voters for Sale, The Industry Standard, Nov. 13, 2000

Addicted to toys, Wired, April 1999 issue

Digital Shelf Space, Wired, December 1995 issue

Feeding Wall Street, Wired, Feb. 1, 1995