Brought to you by Verissimo Ventures, The Very True Podcast features candid startup insights and conversations with early-stage founders, operators, and investors shaping the future of tech. From behind-the-scenes startup stories to hard-earned lessons on fundraising, scaling, and staying resilient, each episode offers a window into what it really takes to build something bold.
Very True by Verissimo
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33 episodes
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Podcast Overview
Brought to you by Verissimo Ventures, The Very True Podcast features candid startup insights and conversations with early-stage founders, operators, and investors shaping the future of tech. From behind-the-scenes startup stories to hard-earned lessons on fundraising, scaling, and staying resilient, each episode offers a window into what it really takes to build something bold.
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Publishing Since
7/1/2025
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Recent Episodes
July 2, 2026
AI Companies Are Trying to Run Uber's Playbook but Missing a Critical Ingredient
<p>In this solo episode of Very True, Alex tackles one of the hottest and most scrutinized topics in tech today: the elusive business model of Artificial Intelligence.</p><p>Right now, almost every major AI company raising billions is running a familiar playbook. It’s a spectacular playbook mastered by Uber: raise an unimaginable amount of money, lose it on purpose to change consumer behavior, and turn the prices up once you own the market. But Alex points out that while everyone is quoting the Uber playbook, nobody is copying the exact piece that actually made it work. By holding Uber’s historical financials up against today's AI landscape, Alex breaks down the difference between a subsidy that is a strategic investment and a subsidy that is just a prayer, revealing why the destination for AI keeps moving. And what does it all depend on? Well-understood Unit Economics that match the business model. </p><p><strong>Episode Highlights:</strong></p><ul><li><strong>[00:00] The Uber Playbook and the Missing Piece:</strong> Alex introduces the core strategy driving AI fundraising today and highlights the stark difference between an unoptimized business and an misunderstood business. </li><li><strong>[01:05] The Simplicity of Uber’s Unit Economics:</strong> Breaking down Uber on a single slide. Alex explains how marketplaces balance supply and demand at a local level, creating a knowable mathematical machine where Customer Acquisition Cost (CAC) could be recovered in five months before printing pure profit. </li><li><strong>[03:45] The 20-Billion-Dollar Land Grab:</strong> A look back at Uber’s aggressive fundraising and financial journey from its 2019 IPO ($13 billion in revenue at an $8.5 billion operating loss) to its massive 2025 turnaround ($52 billion in revenue and $9.8 billion in free cash flow) fueled by behavior change and a shift toward delivery. </li><li><strong>[08:15] AI's Reality Check - Subsidizing in the Dark:</strong> Why the Uber playbook is breaking down for AI labs. Alex discusses the lack of unit economic clarity, the challenge of defining an AI "unit" (is it a token, a query, or an agent?), crumbling switching costs for users, and why AI companies are subsidizing toward a destination they cannot yet draw. </li><li><strong>[13:10] Cooking Up a New Model:</strong> Alex shares how he is using his mechanical engineering background to build a predictive, pressure-tested CAD model for AI unit economics rather than just feeling through the darkness. </li></ul><p><strong>Links & Resources:</strong></p><ul><li><strong>Verissimo Ventures:</strong> <a href="https://verissimo.vc/">https://verissimo.vc/</a></li><li><strong>Follow Alex on LinkedIn:</strong> <a href="https://www.linkedin.com/in/alex-oppenheimer/">https://www.linkedin.com/in/alex-oppenheimer/</a></li><li><strong>Uber Financials:</strong> <a href="https://docs.google.com/spreadsheets/d/19cNzPABWoB8YY8xRHA9UI6xyGdyOEFsZvXQUipwvKWg/edit?usp=sharing">https://docs.google.com/spreadsheets/d/19cNzPABWoB8YY8xRHA9UI6xyGdyOEFsZvXQUipwvKWg/edit?usp=sharing</a></li><li><strong>Unit Economics Overview:</strong> <a href="https://www.loom.com/share/aaddd4018b0a47cc80c6dd64e00846fc">https://www.loom.com/share/aaddd4018b0a47cc80c6dd64e00846fc </a> </li><li><strong>Cal Newport's AI Reality Check:</strong> <a href="https://open.spotify.com/episode/4eV36PZCnUxc3TxSybfVN3?si=75131e6cd91147d9">https://open.spotify.com/episode/4eV36PZCnUxc3TxSybfVN3?si=75131e6cd91147d9</a> </li></ul><p><strong>About Very True:</strong> Hosted by Alex, Very True by Verissimo Ventures explores the honest, unvarnished stories of founders and the real problems they are solving. We look past the hype to find the truth in technology and entrepreneurship.</p>
June 16, 2026
Bet on yourself. Don't be someone's option bet.
<p>In this solo episode of Very True, Alex talks about how venture math actually works and why it looks completely different depending on your fund size, the stage you invest at, and the company you are building.</p><p>Over the last few years, the venture market has gotten increasingly distorted. Between massive headline valuations, intense liquidation preferences, and a setup where VCs can get rich purely on guaranteed management fees, founders are frequently pushed into a moon or bust game. Even if you build a great company with real technology and real revenue, you can easily wind up walking away from a successful mid-market acquisition with nothing.</p><p>Alex breaks down the financial friction between early-stage and late-stage investing, why paper wealth metrics like MOIC are misleading, and why founders need a clean secondary strategy to protect their equity. It all comes down to one question: Are you running your own option bet, or are you somebody else’s?</p><p>Episode Highlights:</p><p><strong>The management fee game.</strong> How venture capital mechanics can misalign a VC’s incentives with a founder’s outcome, allowing partners to build massive wealth on fees regardless of fund performance.</p><p><strong>Clean slates vs recaps.</strong> A look at why the market aggressively floods money into unproven startups while leaving existing, operationally solid companies stranded if they carry historical valuation baggage.</p><p><strong>The entry valuation trap.</strong> A breakdown of how over-paying on entry valuation or over-raising downstream triggers brutal liquidation preferences that wipe out founders and early seed investors at exit.</p><p><strong>MOIC vs DPI.</strong> The critical difference between parading paper wealth and waiting for cold hard cash to hit the bank, and why great early-stage managers care about returning realized capital.</p><p><strong>Running your own option bet.</strong> Why optimizing the middle path of $50M to $250M exits, focusing on sustainable revenue growth, and leveraging early secondary sales is the real playbook for building true generational wealth.<br></p><p>Links & Resources:</p><p>Substack Essay: <a href="https://alexoppenheimer.substack.com/p/thinking-about-writing-down-your">https://alexoppenheimer.substack.com/p/thinking-about-writing-down-your</a></p><p>Medium Essay: <a href="https://medium.com/@Alexoppenheimer/are-recent-valuation-hits-as-unreasonable-as-they-seem-88f5ae789e92">https://medium.com/@Alexoppenheimer/are-recent-valuation-hits-as-unreasonable-as-they-seem-88f5ae789e92</a></p><p>LinkedIn Essay: <a href="https://www.linkedin.com/pulse/how-mess-up-good-company-make-any-money-along-way-alex-oppenheimer/">https://www.linkedin.com/pulse/how-mess-up-good-company-make-any-money-along-way-alex-oppenheimer/</a></p><p>Verissimo Ventures: <a href="https://verissimo.vc/">https://verissimo.vc/</a></p><p>Follow Alex on LinkedIn: <a href="https://www.linkedin.com/in/alex-oppenheimer/">https://www.linkedin.com/in/alex-oppenheimer/</a></p><p>About Very True:</p><p>Hosted by Alex, Very True by Verissimo Ventures explores the honest, unvarnished stories of founders and the real problems they are solving. We look past the hype to find the truth in technology and entrepreneurship.</p>
June 4, 2026
No Easy Answers: A Founder’s Reality Check on the LLM Boom
<p>The honeymoon phase for AI applications is officially over. In this episode of Very True, Alex Oppenheimer sits down with long-time friend Isaac Heller, Co-founder and CEO of Trullion, to cut through the generative AI hype cycle and deliver a grounding reality check on the state of enterprise software.</p><p>Isaac shares his unconventional journey from playing professional poker in Macau to launching an accounting technology company in 2019, a time when the back office was entirely "unsexy." Fast forward to today, and building AI tools for finance is one of the most crowded tables in tech. Alex and Isaac break down why vertical SaaS moats are shrinking, the critical difference between deterministic and probabilistic AI architectures, and the structural threat automation poses to traditional entry-level career paths.</p><p>It is a gritty, honest look at why the rules of technology and career growth are fundamentally shifting, and why there are no easy answers for founders or the next generation of builders.</p><p><strong>Episode Highlights</strong></p><ul><li>[04:21] The Macau Arbitrage & Choosing the Right Table: Isaac explains how his time playing professional poker in China shaped his startup philosophy. It is always better to find an uncrowded, highly lucrative table than to try to be the absolute best player in a hyper-competitive room.</li><li>[22:07] Auditable vs. Probabilistic AI: Why generic LLMs fall short in corporate finance. Isaac outlines the necessity of "Auditable AI," which provides deterministic systems with complete traceability, as opposed to the probabilistic guesswork of foundational language models.</li><li>[28:30] Corporate Gerrymandering: Alex breaks down his concept of "corporate gerrymandering," which is the fracturing of companies into highly artificial, arbitrary line-item roles, and explains how AI is systematically dissolving these operational inefficiencies.</li><li>[40:09] Shifting Economic Premiums: A look at how traditional baseline white-collar skills are losing their market premium and why specialized accounting, law, or radiology work will increasingly be viewed as a historical "art form."</li><li>[52:12] The Core Instinct Crisis: Alex and Isaac tackle the generational gap left behind when AI automates entry-level tasks like basic data input or syntax coding, and how future executives must build their critical thinking skills without the traditional corporate ladder.</li></ul><p><strong>Links & Resources</strong></p><ul><li>Trullion: <a href="https://trullion.com/">https://trullion.com</a></li><li>Verissimo Ventures: <a href="https://verissimo.vc/">https://verissimo.vc/</a></li><li>Isaac Heller on LinkedIn: <a href="https://www.linkedin.com/in/isaacheller/">https://www.linkedin.com/in/isaacheller/</a></li><li>Alex Oppenheimer on LinkedIn: <a href="https://www.linkedin.com/in/alex-oppenheimer/">https://www.linkedin.com/in/alex-oppenheimer/</a></li></ul><p><strong>About Very True</strong></p><p>Hosted by Alex Oppenheimer, <a href="https://verytrue.fm">Very True</a> by Verissimo Ventures explores the honest, unvarnished stories of founders and the real problems they are solving. We look past the hype to find the truth in technology and entrepreneurship.</p><p><br></p><p><br></p>
33 total episodes available
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