Charles’ current portfolio includes AdRoll, auxmoney, BlockCypher, Finxera (formerly Bancbox), HealthIQ, LendingClub (IPO 2014), LendingHome, Motif Investing, On Deck Capital (IPO 2014), Rappi, and StatesTitle. In all, he’s made sixteen successful investments since he joined Foundation Capital in 2005. Of which, Lending Club, OnDeck and EverydayHealth have gone public. Six of his investments have been acquired: PowerSet by Microsoft, Xoopit by Yahoo!, Adwhirl by Google, CloudOn by Dropbox, Zoomer by GrubHub and Refresh by LinkedIn. In addition, DogVacay recently merged with Rover.
In 2016, CB Insights listed Charles among The Top 100 Venture Capitalists, and Forbes named Charles to the Midas List for the second time—citing among other factors his deep experience in all things marketplace lending. Charles attended the 2016 White House FinTech Summit, one year after publishing “A Trillion Dollar Market by the People, For the People,” which became the authoritative must-read on the potential of and challenges facing the marketplace lending industry. The paper has been downloaded more than 30,000 times and has frequently been cited by leading thinkers in finance and the media.
Before joining Foundation Capital, Charles lived the startup journey. He served on the founding team of two high-profile startups: first, the internet service provider @Home Network and, subsequently, the speech-recognition platform Tellme Networks. Both companies’ sales surpassed $100 million by the time of their successful exits. @Home Network went public in 1997, and Tellme was acquired by Microsoft for $760M in 2006.
Charles has always gravitated toward promising new enterprises. In 1989, three years into his tenure in Merril Lynch’s M&A practice, he co-founded OnTime Guide, which soon replaced the OAG Pocket Flight Guide as the must-have resource for frequent fliers (and which has since been fully eclipsed by your smartphone). Charles also launched PrimeTime Partners in 1989 in an effort to establish a new category of self-liquidating promotions for advertisers and direct marketers.
Charles builds companies that change markets. He’s always on the lookout for startups working on the next generation of FinTech, Marketplaces, SAAS and consumer tech solutions and services.
Charles is an alumnus of the Wharton School at the University of Pennsylvania and the Harvard Business School.
A regular commentator on emerging enterprises and markets, Charles has appeared on CBNC, authored opinion pieces for top-tier tech and business publications, and been featured in articles by USA Today, the Wall Street Journal, and others. Charles has been a featured speaker at a number of conferences, including eMoney Conference and Money2020. At Money2020, he presented extensive research on Millennials’ finances, spending habits, and attitudes toward financial technology mobile applications.
Charles moonlights as a AAA little league coach and family vacation planner.