The Longest View with Dez Fleming

Desmond Fleming
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Desmond Fleming hosts visionary business leaders who share insights on how they built their companies and how venture capital made it possible.

  1. FEB 10

    I Never Want to See A PDF Again | Democratizing Private Markets with Opto’s Jake Miller

    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 thinkingHow spending years in Washington analyzing Fed communications built Jake's intuition for parsing unstructured dataThe fundamental infrastructure problems preventing wealth advisors from accessing top-tier private market managersWhy custom fund structures and semi-liquid vehicles are superior to one-size-fits-all offerings for RIAsHow AI is transforming private market due diligence from a weeks-long process to hoursWhat 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.

    50 min

  2. JAN 6

    Why Don Muir Left Private Equity's Dream Job to Start F2

    This week my guest is Don Muir, Co-Founder and CEO of F2, an AI-powered financial intelligence platform. Don's journey from aspiring private equity investor to successful entrepreneur showcases the evolution of fintech in the AI era. After securing his dream job at Apollo Global Management, Don made the bold decision to leave and build his first company in revenue-based financing. Now with F2, he's leveraging AI to solve complex financial analytics challenges for enterprise software VC and fintech venture investors, providing sophisticated financial modeling and analysis tools that were previously only accessible to large institutions. Key Takeaways:  The transition from traditional finance careers to tech entrepreneurship requires complete commitment and "burning the boats"Pre-AI fintech models faced significant limitations in moving upmarket due to third-party API dependenciesAI-first financial platforms can now serve enterprise clients with sophisticated analytics previously requiring large teamsModel-agnostic AI strategies allow companies to optimize performance across different providersThe current environment presents unprecedented opportunities for entrepreneurs in financial technologyDon's story illustrates how new York venture firms and early-stage venture capital professionals are increasingly recognizing the potential of AI-native financial platforms. His experience building both traditional fintech infrastructure and AI-powered solutions provides unique insights into the evolution of financial technology and its impact on investment decision-making.

    49 min

  3. 12/15/2025

    Mitchell Jones on Building Lava: Helping SaaS Companies Price for the Future

    This week my guest is Mitchell Jones, Co-Founder and CEO of Lava, a company building developer infrastructure to reimagine how enterprise software is created and deployed. Mitchell shares his journey from growing up in Dayton, Ohio to studying at Yale, working at Facebook and Dropbox, and ultimately founding his own companies. We explore his philosophy on building enterprise software with a focus on developer experience, his insights on AI-first engineering practices, and how he's creating systems that meet the complexity of modern business needs while maintaining simplicity for end users. Key Takeaways: How growing up in the Midwest shaped Mitchell's competitive drive and approach to entrepreneurshipThe importance of understanding both technical implementation and business context when building enterprise softwareWhy developer experience matters as much as end-user experience in enterprise software VC investmentsHow AI tools are fundamentally changing engineering evaluation and systems architectureThe value of building context-aware systems that integrate company knowledge with LLMsWhy founders need to embrace struggle as part of the journey to building something meaningfulMitchell's perspective on entrepreneurship centers on consistent progress over dramatic moments. He emphasizes that greatness comes from the daily commitment to building when no one else is watching, not from press releases or product launches. His approach to both company building and venture investing reflects a deep understanding that sustainable success requires technical excellence, clear communication, and an unwavering commitment to solving real problems for customers.

    1h 19m

  4. 12/04/2025

    The Competitive Advantage of Caring: Ben Markowitz's Customer-First Approach at Clerq

    This week my guest is Ben Markowitz, Co-Founder and CEO of Clerq, a payments platform serving auto dealerships. Ben shares his journey from JP Morgan to Citadel and eventually founding Clerq, offering raw insights into the realities of building in fintech venture investors territory. We explore why technology alone can't solve financial services problems, the hidden complexities of payments infrastructure, and what it really takes to find product-market fit in an industry dominated by legacy players. Key Takeaways: Financial services innovation requires understanding incentives and ecosystem dynamics, not just building better technologyFinding excellent talent is the hardest operational challenge for early-stage foundersProduct-market fit often starts with underserved customers before expanding to mainstream marketsCustomer support quality creates lasting goodwill and competitive differentiationThe day-to-day reality of entrepreneurship involves endurance through mundane challenges alongside strategic workBen's candid perspective on founder life—from answering password reset tickets at 8 AM to the satisfaction of solving real customer problems—offers a refreshingly honest look at what it means to build a fintech venture investors company. His experience navigating the complex world of payments, banking relationships, and regulatory requirements provides valuable lessons for anyone considering the entrepreneurial path in financial services.

    1h 2m

  5. 11/04/2025

    AI Agents for Private Equity with Rohan Parikh, Co-Founder of Keye

    This week my guest is Rohan Parikh, founder and CEO of Keye, an AI-powered platform revolutionizing due diligence for private equity professionals. Rohan brings a fascinating perspective shaped by growing up in a family of entrepreneurs in Mumbai and spending five years climbing from analyst to director at a French investment bank in New York. We dive deep into why deterministic software is non-negotiable in private equity, where a single investment can represent 5-10% of an entire fund and career-defining decisions hinge on absolute precision. Rohan shares his journey from building a B2B information services company to pivoting Keye into an AI solution that processes millions of rows of Excel data to uncover the true health of businesses during diligence. Key Takeaways: The determinism imperative: In private equity, where single investments can make or break a fund's returns, non-deterministic AI outputs are unacceptable—investors need to understand exactly how every number was calculatedExcel's limitations exposed: PE firms routinely handle data files with millions of rows that Excel literally cannot open, creating a massive bottleneck in the due diligence processThe $50 billion opportunity: Due diligence spending in private equity exceeds $50 billion annually, representing a massive market for workflow transformationStart with the problem: Rohan's advice to first-time founders is to focus on solving a specific problem rather than starting with a technology and looking for applicationsBuilding for the long game: Keye isn't trying to be "AI for finance"—they're laser-focused on owning the entire private equity workflow from sourcing to portfolio managementWhat strikes me most about Rohan is his clarity of vision. While the entire world is rushing to slap AI onto everything, he's building with the discipline of someone who understands that in private equity, being 95% accurate isn't good enough—you need 100%. That constraint has forced Keye to think differently about how they architect their system, combining deterministic computation with AI to deliver both accuracy and insight. It's a masterclass in understanding your customer's actual needs rather than what you think they need.

    42 min

  6. 10/03/2025

    The Future of Private Markets with Ryan Eisenman, Co-Founder of Arch

    This week my guest is Ryan Eisenman, Co-Founder and CEO of Arch, the platform automating private market investment management. Ryan shares the fascinating origin story of how a dinner conversation in New York City led to building what he calls "one-click alt" - the Schwab for private markets. We explore how Arch has grown from a scrappy three-person team surviving on $500K to serving 180+ family offices and major financial institutions. Key Takeaways: Private markets are 30-50 years behind public markets in terms of user experience and automationIt takes 5,500 clicks to manage a single private market investment - Arch has automated 84% of those clicks44% of Arch's clients come through referrals, showing strong product-market fit in the tight-knit financial services industryThe wealth management world needs better experiences as more retail investors seek access to private marketsBuilding in fintech infrastructure requires extreme patience and long-term relationship buildingRyan's journey from consultant to CEO offers valuable insights into building B2B fintech infrastructure, selling to family offices, and the unique challenges of serving the private markets ecosystem. His vision for making private markets more accessible while maintaining their unique value proposition provides a compelling look at the future of alternative investments.

    39 min

  7. 10/03/2025

    Ed Brandman on Building ToltIQ: How AI is Revolutionizing Private Markets Diligence

    Former KKR CIO Ed Brandman joins Dez Fleming to discuss his transition from retirement to founding ToltIQ, an AI-powered platform revolutionizing due diligence for early-stage venture capital and private markets firms. Brandman shares insights from his decade at KKR, where he scaled technology operations from 5 to 145 people as AUM grew from $30-40 billion to $250 billion. He explains how ToltIQ leverages generative AI to analyze virtual data rooms, enabling B2B startup investors and private equity teams to accelerate their diligence processes from weeks to hours. The conversation explores the challenges of building on rapidly evolving AI models, the future of workforce augmentation, and practical advice for college students entering an AI-driven job market. Key Takeaways: AI is transforming traditional diligence workflows by enabling rapid analysis of unstructured documents in virtual data roomsThe evolution from manual document review to AI-augmented analysis represents a fundamental shift in how private markets firms operateBuilding AI applications requires constant adaptation to changing model capabilities and non-deterministic outcomesEvery professional role will soon require AI literacy and daily experimentation with these toolsToltIQ's platform demonstrates how data-driven venture capital firms can maintain competitive advantages while dramatically improving efficiency. As Brandman notes, the models we have today represent the "dumbest" they'll ever be, making early adoption and experimentation critical for future success.

    1h 12m

  8. 08/09/2025

    Cyrus Shirazi on Building a Unified Financial Operating System with Haven

    Cyrus Shirazi, founder of Haven, joins Dez Fleming to discuss his journey from watching his father leave private equity to becoming an entrepreneur himself. After experiencing both the highs and pitfalls at companies like Mainstreet and Meow, Cyrus launched Haven - a unified financial operating system for startups and small businesses. He shares tactical insights on guerrilla marketing, community building, and why he chose hand-to-hand combat over paid acquisition to reach $5.5 million in revenue in just 20 months. Key Takeaways: Build organic growth channels before investing in paid acquisitionFocus on solving problems for your entire customer base, not just subsetsCommunity building and genuine value-add relationships drive sustainable growthThe importance of failing fast and learning from every setbackCyrus's approach to building Haven reflects lessons learned from three different startup experiences, emphasizing the power of authentic relationships and solving real pain points for entrepreneurs. His 500-person WhatsApp group of founders and VCs demonstrates how genuine community building can become a competitive advantage in B2B startup investors markets.

    51 min
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About

Desmond Fleming hosts visionary business leaders who share insights on how they built their companies and how venture capital made it possible.

Information

  • Creator
    Desmond Fleming
  • Years Active
    2025 - 2026
  • Episodes
    13
  • Rating
    Explicit
  • Copyright
    © 2026 Desmond Fleming