Kevin's Entrepreneurial Timeline
November 2004 – DIGG, Founder – The first social news platform with voting on user-submitted content. At its peak, DIGG reached over 38 million monthly users. Rose initially wireframed and designed the platform himself, then hired Owen Byrne as the first developer through Elance. Early team members included Dan Huard (community), Ron Gorodetzky (engineering), and Daniel Burka (design and Kevin’s product thought partner). Kevin later hired Jay Adelson to replace him as CEO and help with fundraising, allowing him to focus on product development. Digg pioneered concepts that would later become standard across social media, including voting as a signal for algorithmic content suggestions (patents sold to LinkedIn) and and crowd-curated news.
October 2004 – Revision3, Co-Founder – One of the first internet television networks, co-founded with Dan Huard and Keith Harrison. David Prager quickly joined the founding team and Jay Adelson was the company's first investor, later serving as CEO. The network produced pioneering shows including:
Diggnation (tech/comedy with Rose and Alex Albrecht)
Systm (deep-dive tech tutorials with Rose and Dan Huard)
Tekzilla (tech reviews and advice with Patrick Norton)
Discovery Communications acquired Revision3 in 2012 for over $30 million, under the leadership of Jim Louderback, marking one of the first major acquisitions of a digital-first video network.
July 2005 – Diggnation, Co-Founder – A weekly tech/comedy video podcast hosted by Rose and Alex Albrecht, running from 2005-2012. The show regularly drew over 250,000+ viewers per episode and helped establish the podcast medium. In addition to discussing top Digg stories, it featured notable guests including Jimmy Fallon, Mark Cuban, Rachel Maddow, Ashton Kutcher among others.
2007 – Pownce, Co-Founder – A social networking and micro-blogging platform co-founded with Leah Culver and Daniel Burka. Pownce innovated by allowing users to share files, events, and links in addition to messages. The platform was acquired by Six Apart in 2008.
2010 - FOUNDATION, Founder — A pioneering long-form interview series featuring intimate conversations with tech luminaries including Jack Dorsey, Ev Williams, Elon Musk, Gary Vaynerchuk, Tony Hawk, Chad Hurley, Dennis Crowley, Ben Horowitz, Matt Mullenweg, and Naval Ravikant. The show helped establish the format of in-depth, personal tech conversations that would later become standard in tech podcasting.
2012-2015 – Google Ventures, General Partner – Rose served as a General Partner, investments in companies including Ripple (Google’s first crypto investment), Medium, Uber, and Blue Bottle Coffee. His focus areas included consumer internet, mobile, and cryptocurrency.
2015 – Watchville, Co-Founder – A mobile app for watch enthusiasts that aggregated news and provided accurate time synchronization. Watchville was the world’s largest watch news app, which led to the merger and Rose's involvement with HODINKEE.
2017 – ZERO, Founder – An intermittent fasting app that has helped millions track their fasting windows and goals. The app combined Rose's interests in technology and wellness, offering features like fasting timers, progress tracking, and educational content.
2017 – OAK, Founder – A meditation app designed to make mindfulness more accessible downloaded by millions of users. The app reflected Rose's personal commitment to meditation, later leading him to a dedicated Zen practice. Oak offers guided meditations and breathing exercises in a minimalist interface, free of charge. Yearning for a deeper experience led Rose to invest in The Way, a full featured app with roots in Zen.
2019-2021 – HODINKEE, CEO – Rose served as CEO of the premier watch media platform, helping build and scale their e-commerce offerings, mobile apps, and launch several successful limited edition collaborations with major watch brands.
2021 – PROOF, Co-Founder – A Web3 media and technology company that created the highly successful Moonbirds NFT collection. PROOF was acquired by Yuga Labs in 2023, marking Rose's entry into the Web3 space.
2025 - True Ventures, Partner — Today, Rose has rejoined True Ventures as a full-time investing Partner, helping support their 450+ teams and $3B+ of assets under management.