Rob Reid
About Rob Reid
Rob Reid (Robert H. Reid) is an American entrepreneur and author. He was the sole founder of Listen.com, where he served as CEO and later as chairman. Listen.com created Rhapsody, which Crunchbase describes as the first online music service to secure full-catalog licenses from all of the major labels.
Reid studied at Stanford University and Harvard Business School. He wrote the nonfiction book Architects of the Web (1997) and two novels, Year Zero (2012) and After On: A Novel of Silicon Valley (2017). After On involves the rise of a superintelligent AI.
He hosts the After On podcast. His own profiles describe him as a tech entrepreneur and early-stage tech investor, based in New York and San Francisco.
Public investor databases list only a small number of his deals. CB Insights shows two investments: GRAI (Seed, April 2026) and an undisclosed Series A-II round in May 2017. Crunchbase lists two portfolio companies. Reid has not published a full portfolio, so these databases probably undercount his activity.
Reid is listed as an angel in GRAI's $9M seed round, announced in April 2026. Khosla Ventures led the round and Inovo.vc co-led it. Other participants named in GRAI's announcement include Tensor Ventures, Tiny Supercomputer Investment Company, Flyer One Ventures, the a16z Scout Fund and the angels Andrew Zhai, Greg Tkachenko and Dima Shvets. Crunchbase describes GRAI as an AI music research company based in Warsaw.
His interest in AI also shows in his writing and podcast. After On centers on a superintelligent AI, and he has written about the risks of advanced AI.
Reid describes himself as an early-stage tech investor. His two database-listed deals are a seed round and a later Series A-II. His one confirmed AI deal is in music, which connects to his Rhapsody background. He has not publicly stated a check size, a fund size or a formal investment thesis, and none is given here.
- GRAI: AI music research company in Warsaw. Reid took part in its $9M seed round in April 2026, led by Khosla Ventures.
Investing activity
Rob Reid appears in 1 AI deal tracked by the Lounge deals desk, and led 1 of them. The rounds are mostly Seed, with a median round size of $9M. The most recent is GRAI (Seed, $9M, Oct 2026).
Rob Reid most often invests alongside Greg Tkachenko, Andrew Zhai, a16z Scout Fund and Dima Shvets, and the companies they back on Lounge are mostly in AI.
Deals
Frequently asked questions about Rob Reid
Who is Rob Reid the angel investor?
Rob Reid is the founder of Listen.com, which created the Rhapsody music service. He is also an author, the host of the After On podcast, and an early-stage tech investor.
Has Rob Reid invested in AI startups?
Yes. He is named as an angel in GRAI's $9M seed round from April 2026, which Khosla Ventures led. GRAI builds AI music technology.
What check size does Rob Reid write?
He has not made a check size public. The databases we checked do not show his amount in GRAI.
What stage does Rob Reid invest at?
He describes himself as an early-stage tech investor. His listed deals include a seed round in 2026 and a Series A-II in 2017.
How can founders reach Rob Reid?
He is on X as @Rob_Reid, and his website is readrobreid.com. He also runs the After On podcast at after-on.com. He has not published a pitch process.
Is Rob Reid an angel investor?
Yes. Rob Reid invests personally as an angel.
What AI companies has Rob Reid invested in?
Rob Reid's AI investments include GRAI. The 1 round on Lounge are listed on this page with amounts, dates and co-investors.
Who does Rob Reid co-invest with?
Rob Reid's most frequent co-investors on Lounge are Greg Tkachenko (1 deal), Andrew Zhai (1 deal), a16z Scout Fund (1 deal), Dima Shvets (1 deal) and Flyer One Ventures (1 deal).