Very True by Verissimo

Alex
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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.

  1. Most Finance Operators Are Treading Water. Ibrahim Automated His Way Out — With Claude Code.

    2D AGO

    Most Finance Operators Are Treading Water. Ibrahim Automated His Way Out — With Claude Code.

    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 backward-looking accounting to forward-looking business calculus, and why the most successful future founders will be those who "decog" themselves from repetitive tasks to focus on high-level judgment. Episode Highlights: [07:35] Data as the Lifeblood: Why viewing data as "blood" rather than "oil" changes how you diagnose a company’s health, allowing a single financial "prick" to reveal the state of the entire organism.[26:00] Leveraging AI for Judgment: Ibrahim explains his philosophy of automating anything that does not require high-level judgment, freeing himself to act as a generalist across sales, success, and support.[18:57] The AI Modeling Copilot: A look at why "vague prompts" fail in finance and how experts use AI to translate complex business models into daily, actionable targets.[34:08] Genesis of a Workflow: Ibrahim shares how he solved his email management pain point by building a private bot that archives, drafts, and updates his to-do list automatically.[55:00] Beyond the "Nerd Fringe": The duo discusses the necessity of collective adoption—how a company where everyone uses AI effectively can outpace legacy incumbents 10x over.[52:57] The Automation Hurdle: Practical tips for financial operators on overcoming the "initial pain" of setting up systems today to unlock limitless productivity tomorrow.Full Chapter List: [00:00] Introduction: The AI Operating System[01:42] The New Generation of Financial Operators[03:07] Ibrahim’s Journey: From Paris to Descript[05:28] Creative Finance vs. Creative Accounting[07:35] Data as Blood: The Circulatory System of Business[10:51] Bridging Structured and Unstructured Data[13:59] Transforming Customer Interactions into Insights[17:15] Building Frameworks: From PowerPoint to Excel[18:57] AI as a Copilot in Financial Modeling[24:08] Meeting People Where They Are: The Power of Context[26:00] The Future of AI Judgment and Proactivity[32:55] The Philosophy of Never Doing the Same Thing Twice[34:08] Workflow Deep Dive: Email Triage and Task Management[38:08] Automating Procurement and Legal Reviews[46:44] Case Study: Doubling M&A Value Through Insight[52:57] Quick Tips for Operators & Future ProspectsLinks & Resources: Descript: https://www.descript.com/Verissimo Ventures: https://verissimo.vc/Ibrahim Cissé on LinkedIn: LinkedIn ProfileAlex Oppenheimer on LinkedIn: LinkedIn ProfileAbout Very True: Hosted by Alex Oppenheimer, 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.

    59 min
  2. Why Math Doesn't Close Enterprise Deals (Micro Episode)

    FEB 23

    Why Math Doesn't Close Enterprise Deals (Micro Episode)

    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 by risk aversion. By understanding these psychological barriers, you can re-engineer your pitch to give companies what they need in a form factor of what they actually want. Episode Highlights: [00:00] Understanding the Profit Margin Trap: The 2% profit margin paradox. Alex explains why walking into a high-volume legacy business and pitching mathematical certainty or an overhaul to their cost structure is a trap.[01:37] Cultural Roadblocks in Legacy Businesses: The reality of the corporate survival mindset. Unlike hyper-analytical startups, the culture of large corporations is about stability and not rocking the boat. Alex breaks down the risk-reward asymmetry: why a VP won't risk getting fired over a broken process just to save the company $50 million for a standard 3% bonus.[03:45] The Wedge: Aligning Solutions with Corporate Goals: How to actually win the deal. Alex explains how to identify the acute issue that's top of mind for a legacy buyer and frame your product around volume growth (what they are comfortable with), while secretly delivering margin efficiency (what they actually need) on the back end.Links & Resources: Verissimo Ventures: https://verissimo.vc/Follow Alex on LinkedIn: https://www.linkedin.com/in/alex-oppenheimer/About Very True: 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.

    6 min
  3. Your Business Model Probably Sucks - Part 2

    FEB 16

    Your Business Model Probably Sucks - Part 2

    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 find the "least common denominator" where your revenue meets your costs. [08:00] Financial vs. Business Models: Why a three-statement model is often "made up" of GAAP innovations (like depreciation), while a business model reveals the actual economic engine. [14:20] The "Uber Playbook" & Unit Economics: A deep dive into how complex marketplaces calculate unit economics, featuring the $6,000 CAC-to-payback example. [18:45] Quality of Revenue: Alex identifies the three pillars of high-value revenue: Reliability, Profitability(Contribution Margin), and Velocity. [24:10] Data as Blood: Why finance isn't just about accounting—it’s a blood test for your company. Good data should result in "non-decisions" where the right path becomes mathematically obvious. Links & Resources: Verisimo Ventures: https://verissimo.vc/Founder Resources (SaaS Definitions): https://verissimo.vc/resourcesFollow Alex on LinkedIn: https://www.linkedin.com/in/alex-oppenheimer/Recommended Reading: The Most Important Thing by Howard MarksAbout Very True: Hosted by Alex, Very True by Verisimo 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.

    53 min
  4. Your Business Model Probably Sucks - Part 1

    FEB 12

    Your Business Model Probably Sucks - Part 1

    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 why it’s easy to get funded but hard to build something that actually makes sense financially down the road.[05:22] Why Your Business Needs a "CAD" Model Just like in mechanical engineering, if a system is too complex to hold in your head, you must model it. Alex explains how digital simulations catch "part conflicts" before you waste millions in capital.[08:14] The Marshall McCall Test "Your outline is weak, and therefore you are weak." Alex breaks down the cognitive dissonance and "fear-based laziness" that stops founders from doing the rigorous math early on.[11:53] Transitioning from Startup to Growth The pivotal moment: realizing that your product is not what you’re selling—the entire business is the product.[12:38] The "One Column Model" Masterclass A simple, actionable framework to audit your business using three elements:Independent Variables: The inputs you control.Dependent Variables: The lagging indicators and outputs.Mechanics: The equations and "physics" that connect them.Next Up: In Part 2, Alex moves from theory to the tactical math of "Units" and the "Blood" of business data. Links & Resources: Verisimo Ventures: https://verissimo.vc/Founder Resources (SaaS Definitions): https://verissimo.vc/resourcesFollow Alex on LinkedIn: https://www.linkedin.com/in/alex-oppenheimer/Recommended Reading: The Most Important Thing by Howard MarksAbout Very True: Hosted by Alex, Very True by Verisimo 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.

    13 min
  5. How Growth Can Drain Your Cash Faster than You Can Raise Money with Ariel Menche

    FEB 5

    How Growth Can Drain Your Cash Faster than You Can Raise Money with Ariel Menche

    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 LTV as a benchmark, the hidden costs of AI on gross margins, and how to build a True CAC model that tracks the actual attribution of every dollar spent. This episode is a masterclass for founders on how to stop lighting money on fire and start building a self funding growth engine. Episode Highlights: [01:05] The Modern Float: Ariel redefines Net Working Capital for the software age, explaining it not as physical inventory, but as the cash cushion required to fund the gap between spending and receiving subscription revenue.[04:02] The LTV Graveyard: Why Alex has thrown LTV in the garbage as a benchmark and how to shift your focus toward LTV as a strictly internal, cohort based operating metric.[08:31] The AI Margin Squeeze: A critical warning on how AI token costs and high touch customer success are ending the era of 99% gross margins and what that means for your unit economics.[12:25] Mastering CAC Payback: Why CAC payback is the ultimate unit economic metric and how to calculate it accurately using the inverse of your churn rate.[14:15] Building True CAC: Alex breaks down the attribution math for a 6 month enterprise sales cycle mapping marketing spend, SDR costs, and AE commissions to the actual month they occur.[20:12] The Annual Contract Hack: Lessons from the early days of monday.com on why being maniacal about annual upfront payments is the best way to solve the working capital problem.[27:44] The No Chain Bike: A powerful analogy on the dangers of venture growth: pedaling as fast as you can with marketing spend, only to realize you’re just coasting downhill without actual attribution.[29:02] The Self Funding Formula: Ariel shares his framework for calculating whether your current customer base generates enough margin to fund the acquisition of new customers without outside debt.[32:12] Three Lenses of Finance: The three types of metrics every founder needs to run a modern tech company: Accounting, Cash, and Economic metrics.Links & Resources: Raftel Strategy: https://www.raftelstrategy.com/Verissimo Ventures: https://verissimo.vc/Follow Ariel on LinkedIn: https://www.linkedin.com/in/ariel-menche/Follow Alex on LinkedIn: https://www.linkedin.com/in/alex-oppenheimer/About Very True: 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.

    34 min
  6. Living in Sprints: Navigating the Eras of a Founder's Life with Todd Saunders

    JAN 29

    Living in Sprints: Navigating the Eras of a Founder's Life with Todd Saunders

    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 to family life. They dismantle the "Golden Handcuffs" myth, debate the true definition of wealth (cash flow vs. paper equity), and explain why "valuation optionality" is often more valuable to a founder than a massive headline-grabbing valuation. Episode Highlights: [03:21] The Accidental Pivot: Todd reveals how he discovered that 30% of his ad-tech revenue was coming from local flooring stores, leading to a massive pivot from a horizontal platform to a specialized vertical SaaS juggernaut.[04:46] Escaping the Machine: Why Todd walked away from Google after only two years to chase "unlimited upside" and control his own destiny, despite having no other job offers.[11:47] The Golden Handcuffs Trap: A candid look at how high salaries in finance and Big Tech can trap talented people in lifestyle creep, preventing them from ever taking the entrepreneurial leap.[32:25] Living in Sprints: Todd and Alex discuss the concept of "sprints"—how life is defined not by a steady cruise, but by intense periods of focus (high school, banking, early-stage building) and the challenge of finding the next mountain to climb[25:11] Valuation Optionality: Why raising a "$100M Seed Round" can actually be a death sentence for a startup. Todd explains the math behind maintaining a valuation that allows for multiple exit scenarios, not just a unicorn-or-bust outcome.[49:54] The Case for Founder Secondaries: Alex argues why allowing founders to take some chips off the table early (via secondary sales) actually aligns them better with investors and allows them to play "offense only."Links & Resources: Broadlume: https://www.broadlume.com/Verisimo Ventures: https://verissimo.vc/Follow Todd on LinkedIn: https://www.linkedin.com/in/tosaunders/Follow Alex on LinkedIn: https://www.linkedin.com/in/alex-oppenheimer/About Very True: Hosted by Alex, Very True by Verisimo 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.

    54 min
  7. How Bad Finance Kills Good Companies with Ariel Menche of Raftel Strategy

    JAN 14

    How Bad Finance Kills Good Companies with Ariel Menche of Raftel Strategy

    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 hats" of a modern CFO, the often-overlooked power of net working capital (using Costco as a prime example), and why traditional SaaS metrics and benchmarking can sometimes lead founders off a cliff. Episode Highlights: [02:22] From the Ring to the Boardroom: Ariel shares his background moving from high-level strategy at KPMG to managing finances at WWE, and his eventual Aliyah to Israel to found Raftel Strategy.[16:07] Street Smarts vs. Book Smarts: The lesson Ariel learned from his father’s Brooklyn factory: "Anyone can sell something, but it’s another thing to get paid."[19:17] Arithmetic vs. Calculus: Alex explains why accounting is linear arithmetic (compliance) while startup finance requires calculus (modeling exponential growth).[21:43] The Four Hats of the CFO: Breaking down the distinct roles within the office of the CFO: Accounting, Treasury, FP&A (Financial Planning & Analysis), and Corp Dev/IR.[27:56] The Hidden Cash Engine: A deep dive into Net Working Capital, deferred revenue, and how companies like Costco use negative cash conversion cycles to fund their own growth.[36:54] The "SaaS Magic Number" Trap: Why linear growth is death in the software world, and how to analyze sales efficiency when aiming for non-linear scale.[49:07] Organizational Debt: How "garbage in, garbage out" data practices and poor chart of accounts structures can blind a CEO to the reality of their business model.[57:43] Against Benchmarking: Why comparing your unique startup to industry averages is often a waste of time compared to optimizing your internal LTV and customer cohorts. Links & Resources:Raftel Strategy: [Link to Website if available, otherwise omit]Verissimo Ventures: https://verissimo.vc/Follow Ariel on LinkedIn: https://www.linkedin.com/in/ariel-menche/Follow Alex on LinkedIn: https://www.linkedin.com/in/alex-oppenheimer/ About Very True: 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.

    1h 2m
  8. Investing in AI, Selling Secondaries and Venture Math with Nick Fitz of Juniper Ventures

    12/29/2025

    Investing in AI, Selling Secondaries and Venture Math with Nick Fitz of Juniper Ventures

    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 Analysis05:46 The Sweet Spot: Companies Two to Five11:52 Moments of Liquidity: Selling Secondary Shares17:55 The Dynamics of Fund Management and Fees26:21 The Challenges of Fundraising and Founder Empathy34:41 Navigating Ownership and Investment Strategies39:45 The Importance of Check Size and Quality in Investments

    36 min
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About

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.

Information

  • Creator
    Alex
  • Years Active
    2025 - 2026
  • Episodes
    24
  • Rating
    Clean
  • Copyright
    © 2026 Alex
  • Show Website
    Very True by Verissimo