Charles’s current portfolio contains fintech breakouts and emerging direct-to-consumer businesses. Fintech investments include Doma, HealthIQ, LendingHome, Auxmoney, OneFinance, Hatch, Branch, Canopy, Agentero, Deepfraud, and Decent. Direct-to-consumer businesses include Rappi, Rover, NextRoll, and Clubhouse. Charles has seen six portfolio companies go public with Uber, LendingClub, OnDeck, Doma, Rover, and Everyday Health. He has also managed nine companies through acquisition: Powerset by Microsoft, Motif by Schwab, CoverWallet by Aon, Finxera by Stonepoint Capital, Xoopit by Yahoo!, CloudOn by Dropbox, Zoomer by GrubHub, Refresh by LinkedIn, and Bureau of Trade by eBay.
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 Merrill 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 CNBC, 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.