Nick Grouf

In January 1995, Grouf met David Waxman on a flight from San Francisco to Boston. Waxman, a master's candidate at the MIT Media Lab, was also a musician. They began working together shortly after they met, and in March 1995, with MIT professor Pattie Maes, engineer Max Metral, Upendra Shardanand, and Yezdi Lashkari, Grouf and Waxman founded Firefly. Originally known as Agents, Inc., Firefly invented collaborative filtering personalization technology which could predict a user's tastes based on previously gathered preferences. First focused on music, it launched as ffly.com in October 1995 and by 1996 it had built a community of more than 3 million users. As the CEO and president of Firefly, Entertainment Weekly wrote that Grouf gave "cold artificial intelligence a warm glow."[9][10]

Firefly, which collected large amounts of personal data, implemented tools and systems for users to manage and note privacy preferences. Key contributors to OPS (Open Profiling Standard), the company developed the underlying data management technology which was later known as the P3P (Platform for Privacy Preferences). "In order for personalization technologies to be effective, people have to be in an environment they can trust," Grouf said in a 1998 interview.[11][8][12][13]

In April 1998, the company was acquired by Microsoft, and Grouf and approximately 70 Firefly employees moved to Microsoft headquarters in Redmond, Washington to work on .NET. The Firefly Passport became the Microsoft Passport. Per the terms of the acquisition, Grouf remained at Microsoft for a year, serving in a role that Esther Dyson described as Microsoft's "privacy conscience."[14][15][16]

After leaving Microsoft, Grouf moved to Northern California, where he was an entrepreneur-in-residence at SoftBank Technology Ventures. In 1999, Grouf, Waxman and Metral founded PeoplePC, which bundled personal computers with internet service and access to discounted products and services and PeopleGive, a separate 501(C)3 entity which provided computers and connectivity to low income people. Initially funded by SoftBank in a round led by its partner, Brad Feld, the company's mission was to "democratize technology." Its business model included collective buying, which allowed the company to generate additional revenue from advertising, partnerships, and premium products.[17][18]

In February 2000 the company announced that they would provide PCs and Internet access to all of the employees of Ford Motor Co. and Delta Air Lines, and in October it was announced that it would open European subsidiaries to enable overseas corporations and governments to offer their employees low-cost home computers and Internet access and later developed partnerships with Vivendi Universal, The New York Times, Blue Cross Blue Shield, and the National Trades Union of Singapore. PeoplePC donated internet access to low-income families through President Clinton's ClickStart initiative, and provided both computers and computer training to economically disadvantaged students through its PeopleGive program.[19][20][21][22]

PeoplePC debuted on NASDAQ in August 2000, and in 2002 the company was acquired by Earthlink.[8]

In 2003, Waxman and Grouf reunited to work on IT and online-fundraising strategies for John Kerry's presidential campaign. As they researched the television advertising infrastructure, they encountered barriers which made the process of buying media and targeting ads difficult. Knowledgeable about keyword-based online advertising, such as Google Adwords, they realized that no similar program for television advertising had been developed. Based on their experience with the Kerry campaign, Grouf and Waxman founded Spot Runner, a service which allowed business to customize a pre-produced television ads, set a budget, and target specific markets. The commercials were run primarily on cable television, where they could be targeted from large urban areas to small suburban neighborhoods, and the platform recommended where and when the commercials would be most effective. The majority of the process was automated through a web interface. Fast Company wrote: "The pair wedded the democratic spirit that underpinned PeoplePC to a variation on the recommendation engine that powered Firefly. Call it Google AdWords for TV."[8][23]

Grouf led the development of Spot Runner’s Malibu Media Platform, a marketplace for buying and selling national and regional ad time. Media buying agencies were concerned with the Malibu platform, which automated processes traditionally done through ad agencies, because “it would mean giving up their reason for being."[24][25]

In 2009, investor WPP filed an unsuccessful lawsuit against Spot Runner. WPP claimed that Spot Runner's founders made secondary sales without disclosure to other investors, and that the company, its outside directors, and its major venture capital investors facilitated those sales. WPP's lawsuit against the company was dismissed by a federal court in October 2009; in 2010 WPP refiled the suit and it was again dismissed. In 2011, in addition to other claims, the US 9th Circuit Court of Appeals dismissed all of the shareholder derivative claims, and the insurers decided to settle the dispute on confidential terms.[26][27] Spot Runner's Malibu Media Platform was acquired by Harris Broadcasting Communications in 2011.[28][29]

In 2011, Grouf founded Clementine Capital, a Los Angeles-based technology incubator. Through Clementine, Grouf has provided resources, capital and strategic guidance for independent entrepreneurs and early-stage companies in both the consumer and business-to-business sector. Among others, he has worked with The BabyBox Company, Loot Crate, and Fig, which was acquired by eBay. [30] In 2013 he co-founded Pluto TV, and served as its founding chairman. Pluto was acquired by Viacom in January 2019 for $340M.[31][32]

In 2016, Grouf teamed with former Goldman Sachs technology banker Michael Parekh and venture capitalist Nate Redmond to form Alpha Edison, a venture capital fund. In May, The Los Angeles Times reported that Alpha Edison was raising $300 million to invest in startups in addition to a $30 million side fund.[2] Alpha Edison has invested in companies including United Dwelling,[33] which helps homeowners convert underutilized garages or backyards into affordable housing, and House Canary, which uses AI for residential real estate data and home valuation.[34]