Very True by Verissimo

Alex sits down with Alex De Simone, a friend since their Stanford days and a fellow mechanical engineer, for a conversation that starts with a VCR turned into a Hot Wheels garage and ends with a server rack in Santa Clara. Alex De Simone is the CEO and co-founder of Avochato, a business messaging platform coming up on ten years, and Alex is an investor. They walk through the company's origin as "C...

In this conversation, Alex reconnects with his friend Itai Joseph, filmmaker and founder of Fondu, to explore what actually goes into making video content that feels effortless, and what it takes to build a creative business without a boss. Itai shares his journey from making home movies as a kid in Zanesville, Ohio, through film school at Northwestern, to building Fondu, a remote-first creative v...

Alex and Nick Greenfield close out their three-part conversation with the episode that's most useful to anyone running or funding a company. Nick walks through the years after Lyft: a stint at on-demand laundry startup Washio, living in the Snapchat house in LA, moving to New York to join Paribus (later sold to Capital One, and whose founders went on to start Ramp), and then co-founding Candid in...

Alex sits down with Nick Greenfield for part two of a three-part conversation. This one is the Lyft story, told by someone who was inside it close to the start. Nick joined a company called Zimride out of school, back when getting into a stranger's car sounded insane to most people, and watched it pivot into Lyft. They get into what product-market fit actually feels like the day it arrives, why th...

Alex sits down with Nick Greenfield, one of his oldest friends, for the first of three conversations recorded in a single sitting. They met at Stanford in 2008 through their randomly assigned freshman-year roommates and have stayed close through nearly twenty years, several cities, and a lot of career moves. This episode is about the early part of a career and the things that never show up on a re...

In this conversation, Alex reconnects with his long-time friend Yaron Hadad, physicist, mathematician, and serial entrepreneur, to explore the changing mechanics of technology, software, and organization building. Yaron shares his journey from theoretical physics research on general relativity and Einstein's equations to co-founding Nutrino, an AI-driven personalized health platform acquired by Me...

In this solo episode of Very True, Alex makes the case that the biggest mistake an AI-powered business can make is treating itself like a SaaS business. It isn't one. This episode is the math behind why.  Every metric we learned to trust to tell us a company is healthy, net dollar retention, the magic number, LTV to CAC, was built on two assumptions: that revenue accumulates and stays, and that gr...

In this episode of Very True , Alex reconnects with his friend of fifteen years, Michael Stoppelman, recorded 7,000 miles apart — Alex in Israel, Michael in the Bay Area. Michael's path runs from a Purdue computer science and biology double-major, through Google's earliest, wildest pre-IPO days building the click-fraud detection systems that got him promoted from post-sales support into engineerin...

In this episode of Very True , Alex reconnects with old friend Nic Poulos, early stage investor at Euclid and former cofounder of Bowery, to dissect how venture capital evolved from a quirky cottage industry into a massive industrial complex. Nic shares his journey from the early days of New York’s seed ecosystem back when writing a $250k check into a B2B SaaS company was considered a novel idea t...

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...