He is the founder and executive chairman of Uptake Technologies, an industrial AI software provider.

He is an early investor[1] of Tempus AI,[2] co-founder of Groupon,[3] Echo Global Logistics, Mediaocean,[4] DRIVIN, and Lightbank.

[12] Keywell started his first business at age 7, a greeting card company called Key Creations.

[16][17] In addition, Keywell was on the board of directors of Sam Zell's Equity Residential for ten years.

[18] In 1999, Keywell and Eric Lefkofsky co-founded Starbelly, an online supply chain management firm, which was acquired in January 2000 by HA-LO (NYSE:HMK) for $240 million.

[20] In June 2006, Keywell co-founded MediaBank, a SaaS provider to the advertising and media buying industry, and was the founding CEO and then on the board of directors until the company's sale.

[23][24] In 2007, Keywell co-founded Groupon,[25] the collective buying platform, which Forbes called 'The Fastest Growing Company Ever' in 2010.

[29] In February 2010, Keywell co-founded Lightbank, a technology venture capital and private equity firm, and was a Managing Director through 2018.

[39] In 2015, Keywell was an early investor in Tempus AI,[40][41] an AI-enabled precision medicine company,[42] and was on its Board of Directors from inception until 2019.

Tempus was named to the CNBC Disruptor 50 list in 2021,[43] and has raised over $1 billion in capital from investors including Google, Franklin Templeton, and T.Rowe Price.

In 2015, Brad Keywell signed The Giving Pledge to donate more than half his wealth to charity.