Very True by Verissimo

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. 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 th...

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. 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...

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. Isaac shares his unconventional journey from playing professional poker in Macau to launching an...

In this episode of Very True , Alex sits down with Roy Rubin, Founding Partner of R2 Ventures and former founder of Magento, to dissect the shifting foundations of enterprise software. Roy shares his incredible journey from starting a freelance programming shop as a UCLA student to building Magento into an open-source e-commerce giant — funding his growth entirely through customers before eventual...

In this episode of Very True , Alex sits down with Elliot Comite, VP of Finance at Perchwell, to dissect the "full-stack" operator mindset. Elliot shares his journey from the high-stakes growth equity world at Stripes Group to the scaling trenches of Ironclad, exploring why the best finance leaders act as the translation layer between the board's "Hawkish" perspective and the team's "in-the-sauce"...

In this solo episode of Very True, Alex introduces a concept he calls Ambient Restlessness, the low-grade mental noise that modern life has wired into most of us, and makes the case that instead of fighting it, we can learn to use it. Drawing on his own experiences mountain biking, running his first half marathon at the Dead Sea, and driving between Jerusalem and Tel Aviv a decade ago, Alex builds...

In this episode of Very True, Alex sits down with Matt Pru, Founder and CEO of Stackmatix, to explore the reality of startup go to market strategies and how the rules of growth have fundamentally changed. Moving beyond the hype of endless funding rounds, Matt shares his journey from scaling MightyHive's sales from $1M to a $150M exit, to bootstrapping an agency that actually scaled down from 10 em...

In a departure from the usual startup and finance conversations on Very True , Alex shares a personal and practical framework for understanding the hidden costs of sustained stress. Whether you're navigating prolonged conflict, a crisis, caregiving, or just a heavy season of life, the biological and cognitive toll compounds in ways we rarely calculate.  Alex breaks down the actual cost of a single...

In this solo episode of Very True , Alex Oppenheimer pulls back the curtain on the "crux of his career" - the art of narrative design and the evolution of financial storytelling. Moving from his early days at Morgan Stanley to his current role as an early stage investor, Alex explores how the role of the "dealmaker" has shifted from a manual, multi person grind to an AI powered solo performance. A...

In this episode of Very True , Alex sits down with Ibrahim Cisse , VP of Finance at Descript , to explore how one of the sharpest financial operators in the game is rebuilding the role from the ground up. Moving beyond simple spreadsheets, Ibrahim has transformed AI into a genuine operating system running everything from email triage and SQL queries to contract redlines and procurement approvals d...

In this solo episode of Very True , Alex breaks down a frustrating paradox for B2B founders: why pitching undeniable efficiency and cost-savings to legacy businesses is often a total trap. If a company has a 2% profit margin, reducing their operating costs by just 2% effectively doubles their profit. It is a mathematical certainty. So why do they completely ignore you when you pitch it? Alex explo...

In the second half, Alex moves from theory to tactics. He tackles the often-misunderstood world of unit economics, the innovation of GAAP accounting, and why "Quality of Revenue" is more important than the top-line number. He also shares his framework for why data is the "blood" of a healthy corporate organism. Episode Highlights [01:50] The WeWork Warning: Alex reflects on the "dollar for 75 cent...

In the first half of this solo deep dive, Alex draws on his background in mechanical engineering to explain why a business model is like a CAD (Computer-Aided Design) drawing. If you can’t simulate your business's "tolerances" digitally, they will surely clash in the real world. Episode Highlights [01:25] The Emperor’s New Clothes Venture capital often rewards perception over value. Alex discusses...

In this episode of Very True , Alex sits down with Ariel Menche , Founder and CEO of Raftel Strategy , to explore the calculus of the modern business model: The New Net Working Capital. Following up on their first conversation, they move from theory to high stakes scenario modeling, breaking down why traditional accounting often fails to capture the reality of SaaS and AI driven companies. Alex an...

In this episode of Very True , Alex sits down with Todd Saunders , CEO of Broadlume , to explore the nonlinear path from Big Tech employee to vertical SaaS mogul. Todd shares his journey of leaving a comfortable job at Google to launch a horizontal ad-tech company, only to discover a hidden goldmine in the flooring industry, a pivot that transformed his business into a dominant market player. Alex...

In this episode of Very True , Alex sits down with Ariel Menche , Founder and CEO of Raftel Strategy , to demystify the critical difference between "accounting" and "strategic finance." Ariel shares his journey from strategy consulting at KPMG and managing budgets at WWE to becoming a go-to fractional CFO for startups. Together, they dismantle the misconception that finance is just about paying ta...

In this conversation, Alex Oppenheimer of Verissimo Ventures and Nick Fitz of Juniper Ventures discuss venture math, seed investing philosophy, building and fundies AI companies, selling secondary and much more. Just two emerging VC managers talking shop during a spontaneous car ride in San Francisco.  Keywords startups, venture capital, investment strategies, AI talent, liquidity, fund management...

In this episode of Very True , Alex sits down with Avi Moskowitz, Founder and CEO of PDQ , to explore the evolution of e-commerce from a simple "copy-paste" of retail to a data-driven, personalized experience. Avi shares his unique entrepreneurial journey—from bootstrapping an ISP and selling medical software to managing a craft beer business in Israel—and how those diverse "chapters" led him to t...

From the high-pressure grind of logistics to a strategic exit in AI: Neri Bluman joins Alex to discuss his journey from Avo to XFunnel. They dive into the "generalist" superpower, the vital importance of taking a career break, and how Neri and his co-founder Beeri built a lean, profitable engine that was acquired by HubSpot in under a year—all without sacrificing their sanity. ____________________...

Alex delves into the complexities of raising venture capital in today's market. Despite the abundance of available funds, the process remains challenging due to market idiosyncrasies. Alex shares valuable frameworks and strategies for founders to navigate the fundraising landscape effectively, emphasizing the importance of understanding the different types of conversations with venture capitalists...

What actually matters in building your career? What is the best place to start? How do you navigate this?  I have had many conversations with young people over the years on this subject, and I am happy to share some insights here. 

Startup valuations get discussed like baseball player stats, but they're much less well-defined. When primary capital is at stake, the calculations are different. Happy to share here some of those nuances and how founders and investors should approach startup valuations.  Check out the fundraising framework here https://verissimo.vc/resources-for-founders

Startup success stories are usually stories of unique circumstances and personalities - each one like a snowflake.  Startup failures fit into a handful of categories. That's what we're talking about today.  Companies with high potential that avoid the pitfalls are the ones that find success - either small, medium or large. But if you can't avoid the unforced errors, you haven't even given yourself...

We are amidst yet another swing of the pendulum when it comes to the software vs. services debate. Is it possible to have high value, low touch software? Are we better off just offering high end consulting services using custom tools?  I am excited to share my conversation with Gabi Steele, CEO of Preql who has done both as she discusses the opportunities and challenges presented by the current ar...

Legendary Silicon Valley episode illustrates this question so well, I just have to leave it here: https://www.youtube.com/watch?v=BzAdXyPYKQo (Contains expletives).  How are startups valued pre-revenue? Is it better to stay in that zone as long as possible?