Join Olu Oyinsan as he travels around the world in conversation with visionary entrepreneurs and investors, unpacking the people, processes, and playbooks behind companies we admire.
OuiTalkPod takes you behind the scenes of how great businesses are built. These stories spark ideas, challenge assumptions, and inspires the journey ahead.
Semyon Dukach on MIT Blackjack, Backing Immigrant Founders and Venture Capital Myths.
Semyon Dukach came to the US at 10 years old as an immigrant, but that didn’t stop him from leading MIT’s legendary blackjack team and raking in millions of dollars from casinos all over the world. Today, as the Founding Partner of One Way Ventures, he backs exceptional immigrant founders building ambitious companies across sectors, with investments including Chipper Cash, Brex, and Helm.ai. In this episode of OuiTalkPod, Semyon shares lessons from decades of entrepreneurship and vent...
5 May 2026
Justin Caldbeck on His Investments in Uber, Space X, Snapchat and His Career Journey.
Justin Caldbeck has spent his career backing some of the most influential companies in modern tech, including Uber, Snapchat, SpaceX, and Grubhub, with prior roles at Bain Capital Ventures and Lightspeed Venture Partners. In this episode of OuiTalkPod, Justin walks us through the defining moments of his journey as an investor operating at the highest level. He shares: - What it takes to identify and back categorically defining companies - The balance between conviction and signal in invest...
20 Feb 2026
Tosin Eniolorunda on His Early Life, Building Moniepoint, and His Bet on the Future of Work
Before Moniepoint became an African fintech powerhouse, Tosin Eniolorunda was a software engineer obsessed with solving hard problems. What started as a focused bet on serving underserved businesses has grown into one of the continent’s most important financial infrastructure companies, processing billions in transactions and powering millions of merchants across Africa. In this episode of OuiTalkPod, we sit down with Tosin to discuss: His early life and path into technology The real story ...
23 Jan 2026
Seth Levine on Fitbit Deal, Grit and Trump’s HB1 Visa Policy.
Seth Levine is a Partner at Foundry and one of the architects of the Colorado startup ecosystem. In this episode, Seth takes us through his early life, formative career moments, and lessons from backing companies like Fitbit. We also discuss his thoughts around entrepreneurship, his book and perspectives on immigration, including the implications of Trump’s U.S. H-1B policy. New episode out. Listen on Youtube, Spotify, Apple Podcasts, and wherever you get your podcasts.
21 Nov 2025
Stefan Lindeberg on his Bets on Spotify, Lovable and AI’s Ticking Time Bomb
Stefan Lindeberg has spent his career backing ideas and companies that have shaped the global tech landscape. This episode dives into the early Spotify years, the realities of scaling world-changing companies, and the messy, human side of venture capital. The full episode is now live, wherever you stream your podcasts.
24 Oct 2025
Global Hustle: The Misa Matsuzaki Blueprint
In this debut episode of OuiTalkPod, Olu Oyinsan sits down with Misa Matsuzaki — Japanese entrepreneur, investor, and bridge-builder for an honest conversation about breaking barriers and building across cultures. From her early days at AGASTA to becoming one of Japan’s youngest women to take a company public, Misa’s journey spans technology, investment, and the future of work. Together, they explore what it means to lead globally — navigating culture, identity, and inclusion in a world...
4 Oct 2025
TRAILER - OuiTalkPod
Join Olu Oyinsan as he travels around the world in conversation with visionary entrepreneurs and investors, unpacking the people, processes, and playbooks behind companies we admire. OuiTalkPod takes you behind the scenes of how great businesses are built. These stories spark ideas, challenge assumptions, and inspires the journey ahead.
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