Very True by Verissimo

Alex
  • 5.0 (1)
  • Entrepreneurship

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. 4d ago

    Growth, GTM, Marketing, Sales and Business Models that Work with Nick Greenfield

    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 2017 as a direct-to-consumer clear aligner company. Candid went from zero to a $100 million run rate in four years with 700 employees and 40 retail locations, and it was still a flawed business. Nick explains exactly why. The heart of the episode is the math. Nick and Alex break down why direct-to-consumer arbitrage collapses as you scale, why the nth customer costs so much more than the twenty-first, and how Candid's pivot to selling through dentists turned a negative $300 per customer into a positive $700 with a 4 to 6x LTV to CAC ratio. Along the way they cover the history of performance marketing, Craigslist as the arbitrage that built Lyft, Uber, and Airbnb, why direct mail is the one channel where the arb never closes, and what "growth" and "GTM" actually mean now. Nick ends with the three business models he most admires, Toast, Shopify, and Ramp, and Alex owns up to passing on the Ramp seed round. Guest: Nick Greenfield, Founder and CEO of Candid. Part three of three. Episode Highlights From Washio to Paribus to Candid: Nick's path through an LA laundry startup, a New York price-tracking company acquired by Capital One, and the founding of Candid, which claims the title of Ramp's first customer. Naivete Is Mission Critical: Nick's rule that if you want to build a small company you need to know the segment, but if you want to build a big one it's better to know nothing, because knowing the limitations keeps you from finding the massive market. Why Candid's DTC Model Was Flawed: Zero to $100 million in four years, and two problems that growth couldn't cure: a one-time purchase with no recurring component, and a medical procedure that needs in-person care. Recurring vs. Reoccurring: Alex's distinction between contractual and habitual repeat revenue, why companies delude themselves on LTV, and why Casper's one-transaction model was at least honest. The CAC Curve and the Nth Customer: Alex draws the curve, Nick does the math. When your Google click goes from $3.21 to $6.42 and seven competitors show up, the incremental profit flows straight to Google, Meta, and Amazon. Growth Is Arbitrage: Nick on the Udemy whiteboard session that taught him the model, $10 customer acquisition on Facebook in 2011, Craigslist as the arb behind Lyft and Airbnb, and why AEO and LLM optimization are today's version of the same trade. Direct Mail Never Dies: The one channel where the price is set by the post office rather than an auction, and why Capital One has spent billions on it. What GTM People Actually Do Now: Nick's honest split: the AEs are still selling human to human, and the growth and marketing people are mostly banging their heads against AI tools, with a handful finding 100x breakthroughs. Candid Today, With the Math: DTC was $2,000 revenue, $800 COGS, $1,500 CAC, negative $300 per customer. B2B is $1,500 to the dentist who charges the patient $5,000, $700 margin per case, CAC falling every year, and a 50x runway before hitting the top of the US market. Consumer Surplus: Toast, Shopify, Ramp: Why the best business models are the ones where you only win when your customer wins, why a $25 Shopify store is unbeatable, and why Ramp beat Brex on product and go-to-market despite being second. Alex Missed the Ramp Seed: "The dumber it sounds and the more impressive the founder is, that's the most interesting stuff." The lesson Alex still carries as an investor. Full Chapter List (00:00) Washio, the Snapchat house, and moving to New York for TAM reasons(01:05) Paribus, Capital One, and being Ramp's first customer(01:45) The origin of Candid: local, regulated, consumer, complex(02:41) Naivete as a founder's advantage(03:28) Zero to $100M in four years, and the two flaws in the DTC model(05:58) Recurring vs. reoccurring revenue, and the Casper Series A(07:25) Why the nth customer breaks the model(07:53) Alex's CAC curve and the sellable addressable market(08:52) Doing the math: Google clicks, seven competitors, and profits accruing to the platforms(11:47) Growth hides all, then cures all: the accumulation function(12:16) The Lyft marketing budget on Nick's personal credit card(12:19) How performance marketing enabled the consumer startup wave(14:24) The Udemy whiteboard, $10 Facebook customers, and the birth of "growth"(16:08) Growth is arbitrage: Craigslist, AEO, and being only as good as your next trade(18:00) Direct mail, the one arbitrage that never closes(18:49) What do GTM people actually do all day?(20:39) Candid today: the fastest growing clear aligner company for general dentists(22:06) B2B2C: why the end-customer CAC drops to near zero(22:39) The full unit economics, DTC vs. dentist channel(24:18) 4 to 6x LTV to CAC, and 50x room to grow in the US(26:31) The trust leverage of a patient's existing dentist(27:11) Consumer surplus: Toast, Shopify, and Ramp(28:13) Alex on passing on the Ramp seed(31:59) Why Ramp beat Brex: better product, better GTM, lower cost of capital(34:08) Shopify at $25 a month, and Alex's "Design the Wave" pricing piece(34:58) Wrap upLinks & Resources Candid: https://www.candidpro.com/Nick Greenfield on LinkedIn: https://www.linkedin.com/in/nick-greenfield-10189923/Alex's Substack piece on pricing models, "Design the Wave, Don't Just Ride It": https://alexoppenheimer.substack.com/Verissimo Ventures: https://verissimo.vc/Alex Oppenheimer on LinkedIn: https://www.linkedin.com/in/alex-oppenheimer/Earlier in the series: Part one is on the early part of a career and the case for range. Part two is the Lyft story, told from the inside. About 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.

    Growth, GTM, Marketing, Sales and Business Models that Work with Nick Greenfield

  2. 5d ago

    Early Days Lyft: When PMF is Obvious but Scaling is Still Hard with Nick Greenfield

    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 the pink mustache did real work, and how Nick more or less invented the job of launching a new city. The three episodes stand alone, so you can start with any of them. Guest: Nick Greenfield, CEO of Candid, early employee at Lyft. Episode Highlights Zimride Before Lyft: Closed ride-share networks sold to universities, a $20,000 contract at a time. It got liquidity at a few schools and was never going to be a big business. Sidecar Cracked It First: Short peer-to-peer rides got liquidity almost instantly. Lyft ran with the model, then Uber X followed. The Shift Underneath: BlackBerry to iPhone, location services, and an App Store that was under four years old. The Pink Mustache Solved a Trust Problem: Not a branding one. It made getting into a stranger's car feel light instead of weird. Two Things, and Everything Else Was Detail: Lyft competed on cheaper rides and faster pickups. Destination entry, emailed receipts, and the suggested donation all came later. Recognizing the 10x: Why operational skill can't save a business that doesn't have one, and why Alex says you know the day PMF arrives. Inventing the City Launch: Turning San Francisco's success into a repeatable playbook, driver acquisition city by city, casting calls in LA, and the guarantee "floor" that got drivers to stay. Churn, Not Acquisition, Could Kill It: The long email to Logan Green, and why keeping drivers on Friday nights was harder than finding them. What Nick Hires For Now: People who solved problems nobody knew were problems yet. Waymo: Whether the same two variables decide the next round. Full Chapter List (00:00) Cold open(01:41) Zimride: long-haul ride sharing and closed university networks(04:14) Why it worked in Europe and not in the US(05:15) Sidecar launches, and the hackathon that became Lyft(07:29) Lyft did it before Uber X(09:23) BlackBerry to iPhone: the technology shift(10:47) The pink mustache(11:37) $25 taxi to $10 Lyft(12:45) Waymo and the same two variables(13:37) Destination entry, suggested donations, emailed receipts(15:39) Alex turns down GM of Lyft SF(15:51) Reverse-engineering San Francisco and the birth of the city launcher(17:24) Drivers first, the hourly floor, then passengers(18:31) Casting calls in LA(20:02) The long email to Logan Green about driver churn(21:44) What Nick hires for now(22:00) Alex's takeaways and part three previewReferenced: Zimride, Sidecar, Uber X, Craigslist, Dropbox, Waymo. Links & Resources Candid: https://www.candidpro.com/Nick Greenfield on LinkedIn: https://www.linkedin.com/in/nick-greenfield-10189923/Verissimo Ventures: https://verissimo.vc/Alex Oppenheimer on LinkedIn: https://www.linkedin.com/in/alexoppenheimer/Next in the series: Part three is on business models, for founders and investors. About 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.

    Early Days Lyft: When PMF is Obvious but Scaling is Still Hard with Nick Greenfield

  3. Sep 7

    Why the Multi-Sport Kid Wins - Nick Greenfield on range, burnout, and the case for working too hard young

    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 resume. Nick shares how a DC baseball camp coach shaped his approach to work and life, why growing up as a multi-sport kid mattered more than going pro would have, and why choosing Ultimate Frisbee over a job in Brazil set the course for his twenties. Alex and Nick dig into range versus spikiness and whether early specialization actually builds better brains or just burns kids out. They compare notes on what really prepares you for investment banking (a rocket science class, it turns out), why looking for work-life balance at 23 is the wrong goal, and whether San Francisco's hustle culture 15 years ago looked anything like the one people talk about today. Nick closes with advice for founders who have already raised: be impatient with your business, patient with the journey, and remember that almost all the value shows up in the outer years. The three episodes stand alone, so start with whichever one grabs you. Guest: Nick Greenfield, CEO of Candid. Episode Highlights Coach Mac and the Wheel of Success: Nick traces his approach to business and life back to Home Run Baseball Camp in DC, where the coach rewarded fun, safety, hustle, and doing it the right way over how hard you threw. Range vs. Spikiness: Alex brings up the Tiger Woods and Roger Federer contrast from David Epstein's Range, and Nick makes the case that nobody actually has the data to prove single-focus specialization builds better brains. Burnout Is Real, Even for Kids: Nick describes burning himself out on baseball young enough to take a year off, and why he's letting his own kids try everything well into their teens. The Three Classes That Prepared Alex for Banking: Financial accounting, a business school valuation class, and ME 140, the rocket science capstone that taught him to gather data, build a model, present it, and pull the all-nighter. Why Balance Is the Wrong Goal at 23: Nick argues that your twenties are when you have the fewest responsibilities, the most energy, and the most pliable brain, so that's the time to push to the edge while mistakes are still recoverable. Was SF Hustle Culture Real 15 Years Ago? Nick was inside Lyft while friends were at Uber, and explains why the answer depended entirely on the company and the role, plus the math behind why some jobs really need 18-hour days. The Biggest Risk Is Not Taking One: Nick's advice for anyone early in their career, and why the ten most successful people he knows all did something their friends questioned. Patient Journey, Impatient Business: Drawing on Danaher's Mitch Rales, Nick tells founders it takes ten years just to get a business going, and Alex translates it into DCF terms: the terminal value is more than 100% of the whole thing. Full Chapter List (00:01) Cold open: why this became three episodes(01:52) Introduction and nearly twenty years of friendship since Stanford(02:59) Home Run Baseball Camp, Coach Mac, and the wheel of success(05:27) Not going pro, and choosing Ultimate over college baseball(06:20) Range vs. spikiness: Tiger Woods, Roger Federer, and Alpha School(08:20) The multi-sport kid, burnout, and raising kids without early specialization(12:26) What actually prepares you for investment banking: accounting, valuation, and rocket science(14:59) Figuring out school, pushing past your limit, and the VO2 max analogy for early careers(16:55) Why work-life balance at 23 is the wrong goal(19:53) Was SF hustle culture real 15 years ago? Uber vs. Lyft from the inside(21:31) The math behind 18-hour days and why some jobs need them(22:13) The biggest risk early in a career is not taking risk(23:51) Advice for founders who have raised: ten years just to get going(26:29) The DCF version of nose to the grindstone(27:09) NVIDIA, Jensen Huang, and what compounding looks like over decadesLinks & Resources Candid: https://www.candidpro.com/Nick Greenfield on LinkedIn: https://www.linkedin.com/in/nick-greenfield-10189923/Verissimo Ventures: https://verissimo.vc/Alex Oppenheimer on LinkedIn: https://www.linkedin.com/in/alexoppenheimer/Range by David EpsteinNext in the series: Part two is the Lyft story, told from the inside. Part three is on business models, for founders and investors. About 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.

    Why the Multi-Sport Kid Wins - Nick Greenfield on range, burnout, and the case for working too hard young

  4. Sep 2

    The Physicist who Hacked Health - Yaron Hadad

    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 Medtronic. Alex and Yaron dive deep into the sharp contrast between high-stakes, regulated medical device engineering and the move-fast mentality of software development. They debate the future of team dynamics in the era of AI, the collapse of legacy SaaS margins in favor of outcome-based pricing, and how code abstraction is redefining what it means to be a software developer. Yaron also breaks down his mental framework for becoming a "problem detector" and shares the four eternal, foundational skills that every founder and next-generation builder needs to master. Episode Highlights High-Stakes vs. Move-Fast: Yaron reflects on moving from startup speed to leading AI and data strategy at Medtronic, contrasting FDA-regulated Class 3 medical devices where zero errors are allowed against Silicon Valley's "move fast and break things" ethos. The 6-Engineer vs. 100-Engineer Problem: Alex and Yaron debate organizational bloat, Jeff Bezos's "Two Pizza Rule," and why small, lean teams leveraging AI are poised to out-execute massive corporate engineering departments. Decalcifying Internal Interfaces: Drawing from SpaceX's vertical integration model, Alex and Yaron discuss how internal territoriality and bureaucracy destroy momentum within large enterprises. The Death of "Lazy SaaS": Alex introduces his thesis on how business models are shifting away from perpetual licenses and traditional SaaS subscriptions toward outcome-based and usage-based pricing, and what that means for software margins. The Evolution of Code Abstraction: Yaron walks through the history of programming from Assembly to C, Python, and now natural language prompts, exploring how AI-driven compactification is changing the leverage of individual developers. The 4 Eternal Skills for the AI Era: Yaron outlines the core competencies that haven't changed: first-principles problem solving, human communication and trust-building, financial literacy, and cultivating a mind tuned for opportunity detection. Full Chapter List (00:53) Introduction & Reconnecting from Palo Alto to Israel(01:47) Yaron's Origins: Coding at 14, Einstein, and Theoretical Physics(02:36) Building Nutrino: Quantifying the Food Footprint(03:39) Startup Speed meets Medtronic & FDA Class 3 Medical Devices(05:23) Yaron's Current Portfolio: Beehive Software, E-Commerce, & Research(06:10) Agility vs. Scale: Is there still a 100-Engineer Problem?(09:22) Internal Calcification and the SpaceX Playbook(12:32) Defining the Enterprise: "A Company So Successful It Can Afford Inefficiency"(19:16) Pricing Volatility, "Lazy SaaS," and Collapsing Margins(24:57) Scale as a Moat: Lessons from Extreme Volume Manufacturing(29:55) Software Engineering in the Prompt Era(34:53) Advice for the Next Generation: The 4 Eternal Skills(38:02) How to Become a "Problem Detector" and Value Creator(40:49) Acute Problems vs. World-Positive ImpactLinks & Resources Beehive Software: https://beehivesoftware.com/Verissimo Ventures: https://verissimo.vc/Yaron Hadad on LinkedIn: https://www.linkedin.com/in/yaronhadad/Alex Oppenheimer on LinkedIn: https://www.linkedin.com/in/alexoppenheimer/About Very TrueHosted 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.

    The Physicist who Hacked Health - Yaron Hadad

  5. Aug 31

    Zeta: The New Magic Number - Why SaaS metrics break on AI companies, and what to measure instead

    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 gross margins are high. SaaS had both, and they were load bearing. AI has neither. Switching costs collapse to near zero when a customer can move every workload in an afternoon, and gross margin, the thing that was always solved in SaaS, is suddenly variable, not high, and moving underneath you every time a new frontier model ships. Take those two assumptions away and the inherited metrics aren't leading indicators. They're a house of cards. So Alex went looking for what to measure instead, and found it somewhere he did not expect: a mechanical engineering class about what happens when a car hits a speed bump. A company absorbing a new model release is the same physics. Zeta, the damping ratio, is the number that says whether you glide over it or get thrown through the roof. The best part is you already have everything you need to calculate it. Two streams, revenue and cost, plotted against every model release. And unlike the SaaS benchmarks, bigger isn't better here. It's about finding consistency in a dynamic system, which comes down to one question every founder should be asking: Am I critically damped, or am I getting shaken apart? Episode Highlights: SaaS was a business model, not a technology. Why talking about "SaaS vs AI" is a category error, and what actually made the SaaS gold mine work across all four DCF variables.The calculus under SaaS. The 2014 realization that ARR is the derivative of recognized revenue, why revenue is an accumulation function, and why that accumulation quietly cured almost every problem a SaaS company had.The two assumptions holding up every metric you trust. Accumulating contractual revenue and high gross margins. Net dollar retention, magic number, and LTV to CAC all sit on top of them, and none of them survive without both.What AI takes away. How switching costs collapse when everything is a prompt, why "they're losing money because people love it" breaks every law of finance, and why value is accruing to the harness, not the model.The speed bump. A sprung, damped mass hitting a speed bump, mapped onto a company absorbing a new model release. Overdamped companies barely react and get eaten on competition. Underdamped companies push everything to the newest model and watch gross margin crater. Critically damped is the whole game.Zeta as the new magic number. Why the SaaS magic number worked, why it isn't portable to AI, and why zeta is, now that Stripe's move to acquire OpenRouter and tools like Ramp mean you can read gross margin by product with a single prompt.Growth reveals problems instead of curing them. In a high-margin accumulation function, growth covers everything. Multiply an up-and-to-the-right chart by a negative gross margin, and the faster it grows, the faster it sinks.Links & Resources:  Frameworks Substack: https://alexoppenheimer.substack.com/ Verissimo Ventures Substack: https://verissimo.substack.com/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. Jul 29

    Everyone's Wrong About AI Moats — Lessons from Inside Early Google

    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 engineering, to becoming the SVP of Engineering who joined his brother Jeremy at Yelp and helped scale it into a public company. Today Michael is a Venture Partner at Verissimo Ventures, an active angel investor across hundreds of companies, and the builder of CC Marvin, an AI chief-of-staff for investors. Alex and Michael pull the thread between two boom eras twenty years apart: Google circa 2003 figuring out whether clicks, CPA, or something else entirely was the real business model, and today's AI labs wrestling with token pricing, seat pricing, and usage-based pricing. They map Anthropic's enterprise-and-coding strategy onto Google's old Android and YouTube playbook, debate whether frontier "omniscient" models will always beat cheaper specialized ones, and ask the harder question underneath it all — is software engineering as a career dissolving, or just being rebuilt around a new killer skill: product design? They close on what's actually durable in tech — chokepoints, brand, and distribution — and what founders and workers should do about the next wave. Episode Highlights [03:17] Life Inside Early Google: Michael recounts working in "Building Pi" during Google's pre-IPO days, riding Segways with Larry and Sergey, and building the click-fraud detection tools that got him promoted from support into engineering. [07:19] From Google to Yelp: How the same "defend against fake signals" instinct that shaped Google's ad business led Michael to join his brother Jeremy's scrappy local-search startup. [15:55] Anthropic's Android Moment: Michael draws a direct line from Google's Android and YouTube acquisitions to Anthropic's enterprise-and-coding land grab with Claude, and why Claude Desktop is the new "connection with the user." [29:20] The CRUD vs. Frontier Split: Why most software will run on cheap open-weight models like GLM, while a shrinking slice of high-stakes work (satellites, bikes, power plants) still demands the most expensive frontier intelligence. [40:22] The Hype/Reality Gap: If AI were truly omniscient, why hasn't it rewritten the Linux kernel or shipped a faster C compiler? Michael's reality check on how far coding agents have — and haven't — come. [51:34] Displacement or Entrepreneurship Boom?: The pair debate job-loss anxieties, why the government's own measurement systems can't be trusted, and why Michael thinks agentic AI nets out to more founders, not fewer engineers — closing with a plug for his new project, CC Marvin. Full Chapter List [00:53] Welcome & Reconnecting Across 7,000 Miles [01:42] From Purdue Biotech Dreams to Google's Early Days [03:17] Inside Building Pi: Larry, Sergey, and Pre-IPO Google Culture [05:31] The All-Star Roster: PMs and Colleagues Who Became Famous VCs [07:19] Defending the Click: Why Fraud Was an Existential Threat [09:43] Jumping to Yelp: Cracking Local's Emotional Intelligence Problem [12:45] 2003 vs. 2026: The Business Model Question Nobody's Solved [15:55] The Android Playbook: How Anthropic Is Building Its Enterprise Moat [21:27] Coding as the Universal Translation Layer [24:41] Software Engineering, Dissolved and Rebuilt by Agents [27:36] Are Coding Agent Margins Actually Durable? [29:20] The Coming Bifurcation: CRUD Apps vs. Frontier Intelligence [33:59] Beyond Coding: Specialized Models for Biology, Physics, and Earthquakes [38:13] Why Product Design, Not Code, Is the New Killer Skill [40:22] The Gap Between AI Hype and Compilers That Still Haven't Improved [42:39] What's Actually Durable: Chokepoints, Brand, and Distribution [47:48] Adapting to the Agentic Era Without Losing Your Job [51:34] The Entrepreneurship Boom & a CC Marvin Plug Links & Resources CC Marvin: https://ccmarvin.com/Verissimo Ventures: https://verissimo.vc/Michael Stoppelman on LinkedIn: https://www.linkedin.com/in/michaelstoppelman/Alex Oppenheimer on LinkedIn: https://www.linkedin.com/in/alex-oppenheimer/ About 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.

    Everyone's Wrong About AI Moats — Lessons from Inside Early Google

  7. Jul 16

    When Pattern Recognition is a Liability - How VC is updating its priors for AI and which ones still hold

    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 is now unlocking massive services budgets. They debate the shifting cultural narrative of the "founder career path," the real world limits of non technical founders "vibe coding" their own enterprise tools, and the looming DPI dilemma hanging over the venture asset class. They also pull no punches on the current state of SPVs and the reality of fund math in a polarized fundraising market. Episode Highlights [11:03] Tech as an Economic Layer: Nic and Alex discuss how technology transitioned from being a distinct investment sector to a foundational layer of the entire economy, and how that shifted VC from a niche asset class to Wall Street's darling.[14:19] The "Founder" Career Path: Is entrepreneurship a calling driven by a need to solve a persistent problem, or has it just become another corporate ladder? Alex and Nic discuss the pros and cons of the mainstreamification of startup culture.[24:14] Vertical SaaS 101: Why the historical knocks against vertical software, small TAMs and niche markets, turned out to be wrong, and how superior CAC dynamics and AI are opening up blue ocean opportunities.[30:06] The New Build vs. Buy: With the rise of Claude and ChatGPT, everyone is suddenly a developer. Nic and Alex explore the limits of "vibe coding" and why complex, enterprise ready software will always require specialization of labor.[39:35] The DPI Dilemma: A candid look at the venture liquidity crunch. Nic breaks down the regulatory and cultural hurdles of the modern IPO window, the role of strategics, and why the math just doesn't work for mega funds playing the fee game.[49:29] The Problem with SPVs: Why the current craze of hired gun SPVs creates massive misalignment with LPs, and why founders and investors need to focus on absolute value creation over manufactured markups.Full Chapter List [00:00] Introduction & High School Flashbacks[02:14] Nic’s Journey: From Tech Banking to Launching Bowery in NY[04:32] When Investment Banking Ruled vs. The Era of the Founder[07:28] Shooting Fish in a Barrel: The 2014 Series A Landscape[11:03] Software Eating the GDP & The Specialization of SaaS[14:19] Entrepreneurship as a Career Path vs. Earned Insights[21:49] Venture Capital: From Cottage Industry to Industrial Complex[24:14] The Vertical vs. Horizontal Software Playbook[28:40] AI's Expansion of Market Potential and Services Budgets[30:06] Build vs. Buy in the Era of Vibe Coding[36:22] The Power of the "From Industry" Founder[39:35] Where is the DPI? Exploring Exits, IPOs, and M&A[44:31] Fund Math: $10M Micro Funds vs. $10B Mega Funds[49:29] SPV Misalignment and the Flight to QualityLinks & Resources Euclid: https://www.euclid.vc/ Verissimo Ventures: https://verissimo.vc/Nic Poulos on LinkedIn: https://www.linkedin.com/in/npoulos/Alex Oppenheimer on LinkedIn: https://www.linkedin.com/in/alexoppenheimer/ About 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.

    When Pattern Recognition is a Liability - How VC is updating its priors for AI and which ones still hold

  8. Jul 2

    AI Companies Are Trying to Run Uber's Playbook but Missing a Critical Ingredient

    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 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.   Episode Highlights: [00:00] The Uber Playbook and the Missing Piece: Alex introduces the core strategy driving AI fundraising today and highlights the stark difference between an unoptimized business and an misunderstood business. [01:05] The Simplicity of Uber’s Unit Economics: 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. [03:45] The 20-Billion-Dollar Land Grab: 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. [08:15] AI's Reality Check - Subsidizing in the Dark: 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. [13:10] Cooking Up a New Model: 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. Links & Resources: Verissimo Ventures: https://verissimo.vc/Follow Alex on LinkedIn: https://www.linkedin.com/in/alex-oppenheimer/Uber Financials: https://docs.google.com/spreadsheets/d/19cNzPABWoB8YY8xRHA9UI6xyGdyOEFsZvXQUipwvKWg/edit?usp=sharingUnit Economics Overview: https://www.loom.com/share/aaddd4018b0a47cc80c6dd64e00846fc  Cal Newport's AI Reality Check: https://open.spotify.com/episode/4eV36PZCnUxc3TxSybfVN3?si=75131e6cd91147d9 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.

    AI Companies Are Trying to Run Uber's Playbook but Missing a Critical Ingredient
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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
    40
  • Rating
    Clean
  • Copyright
    © 2026 Alex
  • Show Website
    Very True by Verissimo

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