The Longest View with Dez Fleming
The Longest View with Dez Fleming
Podcast Description
Desmond Fleming hosts visionary business leaders who share insights on how they built their companies and how venture capital made it possible.
Podcast Insights
Content Themes
Focuses on entrepreneurship, venture capital, and business innovation with episodes exploring fundraising strategies, leadership lessons, and market trends, such as the journey of Jonathan Birnbaum, CEO & Founder of OpenYield, discussing the impact of venture funding on startup growth.

Desmond Fleming hosts visionary business leaders who share insights on how they built their companies and how venture capital made it possible.
This week my guest is Jake Miller, Co-Founder of Opto, a platform democratizing access to private markets for wealth advisors and their clients. Jake’s journey from analyzing markets at Bridgewater to building prediction markets at Prattle to ultimately founding Opto offers a masterclass in identifying broken infrastructure and building solutions that scale. We dive deep into why private markets remain so inaccessible for the wealth channel, how custom fund structures and AI-powered diligence tools are changing the game, and what it takes to build fintech infrastructure that actually serves end clients.
Key Takeaways:
- Why Bridgewater’s radical transparency and quantitative feedback created an unmatched training ground for market thinking
- How spending years in Washington analyzing Fed communications built Jake’s intuition for parsing unstructured data
- The fundamental infrastructure problems preventing wealth advisors from accessing top-tier private market managers
- Why custom fund structures and semi-liquid vehicles are superior to one-size-fits-all offerings for RIAs
- How AI is transforming private market due diligence from a weeks-long process to hours
What struck me most about Jake is his ability to zoom out from tactical problems to systemic opportunities. The vision isn’t just to make private markets slightly more accessible – it’s to build the infrastructure layer that makes these markets actually work for millions of investors who’ve been shut out. That’s the kind of ambitious, patient thinking that builds generational companies in fintech.

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