OuiTalkPod

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 venture investing.

He shares:

* What makes founders investable, and how venture capital can be a force for building a better future.
* Why the best investors don't always offer the highest valuations
* Why venture capital isn't the right path for every company
* Why many businesses are not fit for venture capital
* What separates great founders from everyone else
* How building successful companies can be a force for positive change

This conversation offers valuable insights for founders raising capital, investors deploying it, and builders looking to create lasting impact.

Subscribe to OuiTalkPod for more conversations with visionary entrepreneurs and investors as we unpack the people, processes, and playbooks behind companies we admire.

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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 investing
- Lessons from investing in emerging markets
- Advice for the next generation of fund managers
- How his time as a basketball player Duke shaped his DNA as an investor

This conversation offers valuable insights for builders, founders, and investors shaping the ecosystem. 

Subscribe to OuiTalkPod for more conversations with visionary entrepreneurs and investors as we unpack unpacking the people, processes, and playbooks behind companies we admire.

Follow us:
Instagram: www.instagram.com/ouitalkpod
X: x.com/ouitalkpod
LinkedIn: linkedin.com/company/ouitalkpod
TikTok: tiktok.com/@ouitalkpod

Justin Caldbeck (Caldbeckj), Angel Investor & Managing Partner, D Global Ventures
New Episode. Listen on YouTube Spotify and Apple Podcasts

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 behind building Moniepoint


Building trust and scaling financial infrastructure in Africa


Leadership, discipline, and long-term thinking


His perspective on AI and the future of work


This is a candid conversation about building at scale in one of the world’s most dynamic markets.

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.

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.

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 that’s constantly evolving.

A conversation on courage, innovation, and creating opportunities that cross borders.

Listen now on Spotify, Apple Podcasts, and YouTube.

#OuiTalkPod #MisaMatsuzaki #WomenInTech #GlobalBuilders #InnovationWithoutBorders #ConversationsThatMatter #FutureOfWork #VentureCapital

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.