citybiz+ Motley Fool Ventures Leads $11.5 Million Series A in Sunnyside

Alexandria, Va.-based Motley Fool Ventures has led a $11.5 million Series A in Sunnyside, a San Francisco startup running a mindful drinking program and app. Will Ventures also participated, along with Uncork Capital, Offline Ventures, Joyance Partners, Wisdom Ventures, Eudemian Ventures, Adjacent, Scribble Ventures, Cooley LLP, and MyFitnessPal founder Michael Lee.

Sunnyside, which has raised a total of $14.6 million so far, named Steve Lloyd as its chief product and technology officer. Lloyd previously held the same position at fitness app Strava.

‘Massive’ Opportunity

“Sunnyside has a unique opportunity into a massive new vertical in the wellness industry,” said Kristine Harjes, vice president of Motley Fool Ventures.

Co-founded by CEO Nick Allen, a former Lyft executive, Sunnyside offers a digital health offering, using SMS texts and an app, to help moderate drinking. It charges a modest $99 per year for users, helping them track their drinking habits.

“This is more than just a business for my team and me,” said Allen, who grew up in a household “profoundly impacted” by alcohol use. “By shifting the conversation from the language of addiction and recovery to one of managing alcohol as a proactive investment in our wellbeing, we can help millions of people make a profound positive impact on their lives,” said Allen, whose co-founder comes from a similarly impacted household.

“By creating a non-judgmental approach where balance is the goal, the Sunnyside team expands the addressable audience to anyone looking to improve their health by taking more control over their drinking habits,” said Harjes, who was previously a content strategist, financial editor, podcast host, and marketing manager for

Leadership Change

Motley Fool Ventures, based in Alexandria, Va., is an early-stage, technology-focused fund. Typically, it invests in startups valued at over $10 million, with trailing GAAP revenue of between $500,000 and $5 million. In size, its investments range from $500,000 to $5 million, with a prospective equity stake of 5% or more.

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Since this spring, the firm is led by managing partner Brendan Mathews, after the exit of CEO Ollen Douglass. Mathews, who graduated from the University of Virginia as an Echols Scholar, was part of’s premium services, working closely with co-founders David and Tom Gardner and analyzing public companies. Earlier in his career, Mathews spent nine years in the corporate strategy practice of Accenture, and also worked briefly at two San Francisco hedge funds — Passport Capital and Osmium Partners.

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Motley Fool Ventures has made over 40 investments from its first $150 million fund, raised in 2019. In May 2022, it raised $102 million toward a second fund, with then CEO Douglass setting a target of $300 million. Most of the early money has come from a “feeder fund” — made up of individual investors, according to the Business Journal.

The venture firm’s recent investments include LegalMation, iink Payments, Hungry, Bennie, Bitwise Industries and Passthrough. Last year, it made three exits — Affectiva, StreetShares Platform and StreetShares.