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 acquisition
• Focus on solving problems for your entire customer base, not just subsets
• Community building and genuine value-add relationships drive sustainable growth
• The importance of failing fast and learning from every setback

Cyrus'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.

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 costs
• New technologies like account abstraction are finally making self-custodial platforms viable for mainstream users
• The mobile crypto trading experience remains underserved, particularly for advanced traders
• Building in crypto requires a product-first approach rather than starting with marketing and tokens

Bradford'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.

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 ratios
• Basic Capital targets B2B markets, specifically PE roll-ups acquiring small businesses
• The company focuses on enabling asset ownership rather than just access to investing
• Entrepreneurship requires tolerance for uncertainty and long feedback loops unlike traditional high-achievement careers

Abdul 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.

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 with
• Investment firms manage billions but buy technology like small businesses - expect long sales cycles and limited tech resources
• Speed beats perfection in financial data - analysts need usable data in minutes, not perfect data in days
• AI won't replace investors, but will help firms encode their investment DNA and make faster decisions
• The career risk of starting a company is lower than most think - the tech ecosystem highly values founder experience

The 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.

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 costs
• Modern capital markets require dynamic, configurable systems rather than rigid workflow software
• The "miracle" moments in startups often come from unexpected customers - Ramp became their ideal first client despite being ranked last initially
• B2B startup investors must understand that feedback becomes less honest as companies gain traction, making early customer rejections more valuable
• Building in capital markets requires choosing specific counterparties to serve rather than trying to be everything to everyone

Tsui 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.

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 investors
• Three key catalysts enabled OpenYield: return of meaningful interest rates, improved market maker algorithms, and new fintech infrastructure
• Investment grade bonds offer equity-like returns (6-8%) with significantly lower risk due to capital structure seniority
• Bond markets remain fragmented and voice-driven, creating opportunities for electronic marketplace disruption
• Cold outreach and maximizing surface area remain critical for early-stage founder success

Jonathan'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.