Why Serial Entrepreneurs Make Top VCs: Google & Groupon Exits; Oura & Kickstarter Investments w/ Jyri Engeström

We’re thrilled to feature Jyri Engeström, a serial entrepreneur who found early success with exits to Google and Groupon. Now an investor, Jyri continues to shape the startup landscape as a General Partner at Yes VC, the fund he co-founded with his partner, Caterina Fake, co-founder of Flickr. At the same time, Jyri makes significant strides in building and investing in startups alongside Petteri Koponen at Lifeline Ventures in Finland. We delve into the opportunities and technologies shaping the future, lessons Jyri has learned from his time in Silicon Valley, and how Finland is positioning itself as a global startup hub. Jyri’s deep understanding of network theory, social dynamics, and his curiosity about emerging markets—from space colonization to geopolitical shifts—makes this an episode you won’t want to miss. TIMESTAMP / KEY TAKEAWAYS 0:00 - Intro 02:41 - The Innovator’s Dilemma, Sociology, & bi-continental life in Finland & the US 06:20 - Working in Nokia to founding Jaiku 08:56 - Google’s acquisition of Jaiku 12:52 - Selling Ditto to Groupon; “I knew to kill the app immediately after the acquisition,” 16:09 - Lessons learned as a serial entrepreneur; leadership 19:01 - New chapters with True Ventures and Yes VC; patterns of success in portfolio  25:04 - Yes VC’s super early stage approach; thoughts on legacy 32:06 - Identifying the potential unicorns; how to be curiosity-driven, continuously 37:00 - Minting the unicorns & the anti-portfolios 39:37 - The founder product fit; Petteri Koponen’s pattern of success 44:48 - Raising children; parallel entrepreneurship 49:58 - The liquidity & exit landscape and deal flow in Finland today 54:11 - Jyri's trajectory for the next five years; messages to global investors 56:29 - Billion Dollar Questions Brought to you by Helsinki Partners The third edition of Founders to Finland Program helps international scale-up founders build their business network in the Nordics. This 7-day program takes place in Helsinki in November, and its 15 selected participants get to experience the magic of the Slush startup conference and valuable side events with a free ticket. Expect hyper-relevant networking, personal introductions to local companies, and tailored info sessions to learn more about the innovative spirit of the Finnish scale-up culture. Learn more and apply by September 1! ABOUT JYRI Jyri has invested in several unicorns including Unity, Oura, Iceye and Boom Supersonic. Jyri’s entrepreneurial journey began with Jaiku, a mobile social networking service he co-founded with Petteri Koponen and sold to Google in 2007. He sold his second company Ditto, a recommendation service, to Groupon in 2012. In 2020 he founded Primary Diagnostics, a healthcare platform serving tens of millions of people across the U.S. For four years Jyri was at True Ventures, a leading Silicon Valley venture fund, where he invested in e.g. Iceye, the world’s largest radar satellite constellation, with Lifeline. Alongside Lifeline Ventures Jyri is Partner at Yes VC, a venture firm he co-founded with Caterina Fake in San Francisco. Yes VC has notable investments in carbon capture, post-fossil energy, space and AI. Jyri combines company-building with venture investing. “Entrepreneurship is a skill. It takes discipline and practice. Each company we build improves our hit rate going forward.” FOLLOW JYRI: LinkedIn | X/Twitter | Instagram | Podcast: Startup-Ministeriön - PODCAST INFO: Podcast website: https://billiondollarmoves.com Watch on Youtube: https://tinyurl.com/sarahchenglobal Join the community: https://sarah-chen.ck.page/billiondollarmoves FOLLOW SARAH: LinkedIn: https://linkedin.com/in/sarahchenglobal Instagram: https://instagram.com/sarahchenglobal Twitter: https://twitter.com/sarahchenglobal