Very True by Verissimo

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 to today's highly concentrated, hyper competitive landscape.

Alex and Nic dive deep into the evolution of vertical software, exploring how TAMs expanded beyond anyone's predictions and how AI...

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 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 ho...

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 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...

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 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...

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 eventually selling to eBay. Today, as an investor writing pre-seed and seed checks, Roy is wrestling with the same question Alex is: what actually is enterprise software anymore?

Alex and Roy dive deep into the rapid commoditization of...

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" reality.

Alex and Elliot dive deep into the psychology of the venture ecosystem, the necessity of "narrative control" during a fundraise, and the fundamental difference between building a model and building a company. They discuss...

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 a practical spectrum of focus states and shows how matching the right mental load to the right physical activity can unlock creativity, deepen learning, and replace...

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 employees to just 3 while increasing revenue.

Alex and Matt dive into the critical differences between B2B and B2C marketing, the evolution of search and social algorithms, and the "...

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 stress event (it's never just "ten lost minutes"), how chronic depletion ruins our decision-making, and the invisible "social cascade" that drains our patience right when we need it most. By understanding the physical and p...

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.

Alex breaks down the distinction between "rinsing and repeating" and true financial translation: taking a business that has never existed before and building the financial frameworks that...

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 directly from a terminal.

Alex and Ibrahim dive into the mindset shift required to move from treading water to deep operational insight. They discuss the concept of "Data as Blood," the transition from...

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 explores the psychological roadblocks that prevent massive corporations from buying logical solutions. He explains why founders need to stop pitching math and start pitching survival, recognizing that corporate culture is heavily driven...

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 cents" model and why zero-interest-rate environments can hide broken business mechanics for years.

[04:25] Defining Your "Unit": Whether it’s a contract, a cohort, or a node, Alex explains how to...

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

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 and Ariel dive deep into the working capital hole explaining why even a company with great unit economics can go bust by growing too fast. They cover the dangers of relying on...

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 and Todd dive deep into the philosophy of "Living in Sprints," discussing how high-performers navigate the intense phases of life, from the academic grind to the startup gauntlet and eventually...

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 taxes and processing payroll.

Alex and Ariel dive deep into the "arithmetic vs. calculus" of business—explaining why accounting looks backward at compliance, while true finance looks forward at exponential growth. They cover the essential "four ha...

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, secondary sales, fundraising, investment returns, decision making

Chapters

00:00 The Startup Landscape: A 100 Company Analysis
05:46 The Sweet Spot: Companies Two to Five
11:52 Moments of Liquidity: Selling Secondary Shares
17:55 The Dynamics of Fund M...

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 tackle the $270 billion problem of cart abandonment. Together, they discuss why trust and logistics are the new battlegrounds for merchants, how to listen to customers at scale using AI, and the future of "autonomous checkout."

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.

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What does it take to build a company that big tech giants want to buy? Sometimes, it starts with doing absolutely nothing.

In this episode of Very True by...

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 and the emotional dynamics involved. He also highlights the significance of aligning with the right investors and the role of junior VCs as advocates in the process.

Keywords

venture capital, fundraising strategies, market idiosyncrasies, investor alignment, junior VCs

Takeaways<...

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 a chance! 

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 array of AI tools in the data space. 

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? 

Happy to share a discussion with Yaakov Carno, founder of Valubyl, which is a leading PLG consulting agency focused on the specific bottle neck of user activation. He shares stories from the trenches of working with dozens of companies and helping navigate their product and growth optimization. 
Follow Yaakov on social media to get his latest tips and ideas on how to maximize user activation: https://www.linkedin.com/in/yaakov-carno/
https://www.valubyl.com/

Is ARR dead with the advent of AI companies? Do we even know what ARR is? Why does it matter? Why is everyone so confused about it? 
Nerding out on tech finance finance, yet again. 

related posts: 
https://docs.google.com/presentation/d/1CUxLWt16Ky5eulArPm4cTSubkZWQ8rkBDPVZWHwJxUU/edit
https://alexoppenheimer.substack.com/p/inventing-arr
https://alexoppenheimer.substack.com/p/calculus-in-saas  

Want to be the next $50Bn startup? Maybe... maybe not. 
How the economics change the reality on the ground, even at the early stage. 
Subscribe to our monthly updates here: https://verissimo.substack.com/

Today I discuss the painful reality of venture: investors are wrong a lot. They lose money. But are all mistakes created equal? Or is there a better way to be wrong. I dive in here to review a market take that I had ~3 years ago to see how things have developed in the market and in my one portfolio when it comes to the less fortunate situations in early-stage investing. 

As always, feel free to reach out with feedback or questions. 

Original piece here: https://alexoppenheimer.substack.com/p/expensive-options-and-losing-big

In this episode, I break down the Financial Operations Flow. This is targeted towards CEOs (CFOs can also listen if they want), to help business leaders better understand how to quantify the resource allocation they need to be doing all the time. 
Every business needs a digital twin... Good news: for most of them, Excel is a sufficient tool to have a huge impact - it just needs to be used correctly. 

Original post here: https://alexoppenheimer.substack.com/p/the-finops-flow

🎧 New on the Podcast: The Evolving Role of a CTO

This episode dives deep into how the CTO role evolves—from early-stage coding to scaling teams, making strategic decisions, and integrating AI without losing your technical edge.

Featuring:

💡 Key themes explored:

🎧 New on the Podcast: Legal Essentials for Founders

In this episode of the It’s All About Everything series, we dive into the legal foundations every founder should get right from day one. From filing your 83(b) on time to guiding your legal team through negotiations and keeping a clean cap table, our expert panel breaks down the critical legal decisions that can make—or break—your startup's future.

Whether you're raising your first round or scaling fast, this conversation will help you avoid costly legal pitfalls and build with confidence.

Featuring:

🎧 New on the Podcast: Tax Strategies and Wealth Management

In this episode of the It’s All About Everything series, we break down the financial essentials every founder should understand before—and after—a liquidity event. From QSBS and 83(b) elections to trust structures and the family office mindset, our expert panel shares real-world strategies to help you protect your upside and build long-term financial stability.

Whether you're preparing for an exit or just getting started, this episode will help you make smarter, more informed financial decisions.

Featuring: