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.

Episodes

  1. 15H AGO

    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

  2. DEC 4

    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

  3. NOV 4

    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

  4. OCT 3

    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

  5. OCT 3

    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

  6. AUG 9

    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

  7. AUG 9

    Building Dexari, Crypto's Next $100bn Opportunity

    Chuck Bradford, founder and CEO of Dexari, shares his journey from engineering student at UPenn to crypto entrepreneur. After experiencing the inner workings of centralized exchanges at Binance US, Bradford identified a massive opportunity to combine the user experience of traditional fintech with the benefits of decentralization. Dexari is building a mobile-first, self-custodial crypto platform that leverages account abstraction and modern blockchain infrastructure to deliver advanced trading features without the overhead costs of centralized exchanges. Bradford discusses the technical challenges of building in crypto, the importance of product-market fit, and why he believes the future of crypto belongs to self-custodial solutions that don't compromise on user experience. Key Takeaways: Centralized exchanges operate more like traditional banks than decentralized platforms, creating significant overhead costsNew technologies like account abstraction are finally making self-custodial platforms viable for mainstream usersThe mobile crypto trading experience remains underserved, particularly for advanced tradersBuilding in crypto requires a product-first approach rather than starting with marketing and tokensBradford's vision extends beyond just replacing centralized exchanges - he sees Dexari as part of a broader convergence between traditional fintech and crypto, where self-custodial solutions become the dominant model for digital asset management.

    42 min

  8. JUL 10

    Why "Saving is a Scam" and How Basic Capital Unlocks Asset Ownership with Adbul Al-Assad of Basic Capital

    This week on The Longest View, Desmond Fleming sits down with Abdul Al-Assad, founder and CEO of Basic Capital, shares his remarkable journey from growing up in Damascus during the Syrian civil war to building a revolutionary fintech company in New York. As a Palestinian entrepreneur who arrived in America with $140 and no connections, Abdul built Basic Capital to solve what he calls the "cold start problem" of wealth building - helping everyday Americans become asset owners through innovative 401k solutions. The conversation explores Abdul's philosophy that "saving is a scam" for average earners and how his company enables working-class Americans to access leveraged investing typically reserved for the wealthy. He discusses partnering with PE roll-ups and small businesses like Service Professionals, an HVAC company in New Jersey, to provide employees with advanced retirement investing tools. Abdul also shares insights on entrepreneurship, the difference between high achievers and entrepreneurs, and his vision for preventing American society from "crumbling from within" due to wealth inequality. Key Takeaways: Traditional saving favors the wealthy due to higher saving rates and lower cost-of-living ratiosBasic Capital targets B2B markets, specifically PE roll-ups acquiring small businessesThe company focuses on enabling asset ownership rather than just access to investingEntrepreneurship requires tolerance for uncertainty and long feedback loops unlike traditional high-achievement careersAbdul Al-Assad is building Basic Capital to democratize wealth creation by giving working Americans the same tools wealthy individuals use to build generational wealth - access to leveraged, diversified, cash-generating assets through their workplace retirement plans.

    1h 17m

  9. JUL 10

    How Understory is Revolutionizing Private Market Data for Investors

    Eric Shapiro and David Fine, co-founders of Understory, join Dez Fleming to discuss their journey from Columbia philosophy classmates to building a company that transforms how financial analysts work with private company data. Eric shares his transition from Elliott Management to entrepreneurship, while David brings his experience from Dynamic Yield and McDonald's. They explore the challenges of selling to investment firms and their vision for unlocking proprietary insights from unstructured financial documents. Key Takeaways Finding the right co-founder matters more than any other decision - work with someone you genuinely enjoy spending time withInvestment firms manage billions but buy technology like small businesses - expect long sales cycles and limited tech resourcesSpeed beats perfection in financial data - analysts need usable data in minutes, not perfect data in daysAI won't replace investors, but will help firms encode their investment DNA and make faster decisionsThe career risk of starting a company is lower than most think - the tech ecosystem highly values founder experienceThe conversation reveals how deep domain expertise combined with technical innovation can address longstanding inefficiencies in financial markets. The founders emphasize that while AI can accelerate analysis and pattern matching, the craft of investing—sourcing deals, building relationships, and making judgment calls—remains irreplaceably human. Their story demonstrates that successful fintech ventures require not just understanding the technology, but deeply understanding how investment professionals actually work and what their institutions truly need.

    49 min

  10. JUL 10

    How Fintech is Transforming Banking Operations with Jeremy Tsui, CEO and Co-Founder of Finely

    Jeremy Tsui, Founder and CEO of Finley Technologies, joins Dez Fleming on The Longest View podcast to discuss his transition from Goldman Sachs private credit investor to fintech venture investors-backed entrepreneur. Tsui shares insights on building enterprise software VC solutions for the evolving capital markets landscape, where traditional banks and private credit funds increasingly collaborate rather than compete. Key Takeaways: AI startup funding has enabled 95% automated credit agreement processing, dramatically reducing implementation costsModern capital markets require dynamic, configurable systems rather than rigid workflow softwareThe "miracle" moments in startups often come from unexpected customers - Ramp became their ideal first client despite being ranked last initiallyB2B startup investors must understand that feedback becomes less honest as companies gain traction, making early customer rejections more valuableBuilding in capital markets requires choosing specific counterparties to serve rather than trying to be everything to everyoneTsui emphasizes that successful founders need competitive drive over financial optimization, as most startups fail regardless of economic rationality. His advice centers on betting on yourself, maintaining high standards, and recognizing that founders have more control over outcomes than they typically realize.

    51 min

  11. JUN 12

    Revolutionizing Bond Markets with Jonathan Birnbaum, Founder of OpenYield

    Desmond Fleming welcomes Jonathan Birnbaum, founder of OpenYield. On the first episode of The Longest View, Jonathan shares his journey from Morgan Stanley trading floors to building a modern bond marketplace. Drawing from his experience in fixed income trading and fintech venture investors backing, he discusses how OpenYield is democratizing access to bond markets through technology. The conversation covers the massive $8.3 trillion fixed income market, the challenges of bond market fragmentation, and how new York venture firms are supporting infrastructure innovation. Jonathan explains why bond investing offers compelling risk-adjusted returns in today's yield environment and how his platform serves retail brokerages, asset managers, and institutional clients seeking better liquidity and pricing transparency. Key Takeaways: The fixed income market ($8.3T issuance) is 60x larger than equity markets but remains largely inaccessible to retail investorsThree key catalysts enabled OpenYield: return of meaningful interest rates, improved market maker algorithms, and new fintech infrastructureInvestment grade bonds offer equity-like returns (6-8%) with significantly lower risk due to capital structure seniorityBond markets remain fragmented and voice-driven, creating opportunities for electronic marketplace disruptionCold outreach and maximizing surface area remain critical for early-stage founder successJonathan's story illustrates how deep domain expertise combined with technological innovation can disrupt massive, traditional markets. OpenYield represents the evolution of fixed income trading from relationship-driven, voice-based systems to transparent, electronic marketplaces that benefit all participants through better pricing and accessibility.

    51 min
  • 11 Episodes

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
    2K
  • Episodes
    11
  • Rating
    Explicit
  • Copyright
    © 2025 Desmond Fleming