The Longest View with Dez Fleming

This week my guest is Connor Dougherty, CEO and co-founder of Valinor. Valinor is a direct lender that originates credit for stablecoin native and stablecoin friendly businesses, including fintechs and neobanks like Rain, with the goal of building what Connor calls a modern credit institution that operates natively on chain. Connor spent six years at Blackstone, starting in 2016 on the credit side of the business (GSO, founded by three partners before Blackstone's acquisition), working across a large distress fund before private credit became the asset class it is today. He co-founded Valinor with Lily, his colleague from Blackstone, and the company has now been operating for about two and a half years, with institutional capital brought in roughly a year ago to accelerate growth.

We get into why Connor thinks stablecoins unlock credit as the natural next step after payments, how Valinor partners with infrastructure providers rather than building everything itself, what "open credit" means as a successor to bank-originated and then private credit, and how new tools called vaults could let fund managers offer far more customized products than traditional fund structures allow. Connor also talks about the difference between opportunistic distress investing and the thematic, growth-oriented origination Valinor practices today, how the firm uses AI on the pre-trade side of underwriting, and what he's learned managing people and communication as a first time founder.

Key Takeaways

• Connor Dougherty says the stablecoin market has grown from 0 to 300 billion dollars in circulation over about ten years, and his house view is that it will grow another 10x from today.
• Valinor acts as a direct lender to stablecoin native and stablecoin friendly borrowers, including portfolio company Rain, providing instant settlement, programmability and transparency that traditional financing cannot match.
• Connor describes Valinor's underwriting discipline, structuring deals so the firm could be multiple standard deviations off on its assumptions and still not lose money, a mindset he traces to his time on Blackstone's distress desk.
• Valinor focuses on shorter duration, asset backed credit such as receivables, where API integrations allow daily draws and real time covenant and compliance checks instead of delayed, manual reviews.
• Connor explains vaults as an ERC standard smart contract where investors deposit stablecoins and receive a receipt token, with a curator investing the capital on their behalf, functioning like a transparent, easier to launch fund.
• Connor says Valinor has built an internal "investor OS" with a director of automation rather than relying on off the shelf AI tools, because the firm's underwriting does not map well to commodity private credit workflows.
• Connor's main lesson as a first time founder has been investing in people, clarity of goals, and a consistent cadence of communication, including daily full team meetings and Friday office hours.
• Connor says his biggest takeaway from rowing in college was the value of shared team success, which he now tries to recreate at Valinor.

Connor closed by saying he has never once looked back on the decision to start Valinor, even measured against staying on the partner track at Blackstone, and that the real risk was in not making the leap. That framing, treating the decision to found the company as something that would never stop nagging at him otherwise, is worth sitting with if you are on the fence yourself.

Connect with Connor Dougherty: https://www.linkedin.com/in/connordougherty-valinor/
Connect with Desmond Fleming: https://www.linkedin.com/in/desmond-fleming-b84042100/

00:00 How stablecoins are unlocking credit
04:00 Who Valinor actually serves
09:05 Building a modern credit institution
11:13 Where AI fits into underwriting
14:20 The assets Valinor lends against
19:08 Lessons from Blackstone's distress desk
23:46 What open credit means
28:22 Vaults and the future of fund management
33:26 Lessons from being a first time founder
36:30 What rowing taught him about team success
40:04 His advice on taking the leap

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.

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 dependencies
• AI-first financial platforms can now serve enterprise clients with sophisticated analytics previously requiring large teams
• Model-agnostic AI strategies allow companies to optimize performance across different providers
• The current environment presents unprecedented opportunities for entrepreneurs in financial technology

Don'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.

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 entrepreneurship
• The importance of understanding both technical implementation and business context when building enterprise software
• Why developer experience matters as much as end-user experience in enterprise software VC investments
• How AI tools are fundamentally changing engineering evaluation and systems architecture
• The value of building context-aware systems that integrate company knowledge with LLMs
• Why founders need to embrace struggle as part of the journey to building something meaningful

Mitchell'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.

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 technology
• Finding excellent talent is the hardest operational challenge for early-stage founders
• Product-market fit often starts with underserved customers before expanding to mainstream markets
• Customer support quality creates lasting goodwill and competitive differentiation
• The day-to-day reality of entrepreneurship involves endurance through mundane challenges alongside strategic work

Ben'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.

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 calculated
• Excel'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 process
• The $50 billion opportunity: Due diligence spending in private equity exceeds $50 billion annually, representing a massive market for workflow transformation
• Start 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 applications
• Building 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 management

What 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.

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 automation
• It takes 5,500 clicks to manage a single private market investment - Arch has automated 84% of those clicks
• 44% of Arch's clients come through referrals, showing strong product-market fit in the tight-knit financial services industry
• The wealth management world needs better experiences as more retail investors seek access to private markets
• Building in fintech infrastructure requires extreme patience and long-term relationship building

Ryan'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.

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 rooms
• The evolution from manual document review to AI-augmented analysis represents a fundamental shift in how private markets firms operate
• Building AI applications requires constant adaptation to changing model capabilities and non-deterministic outcomes
• Every professional role will soon require AI literacy and daily experimentation with these tools

ToltIQ'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.

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.