Very True by Verissimo

Why Good Video Looks Effortless (and Isn't)

Alex — Wed, 30 Sep 2026 16:56:40 +0300

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 video agency, out of the shift to digital storytelling during the pandemic.

Alex and Itai dive deep into the full anatomy of video production, from concept and audience to the shoot and the edit, and how generative AI is starting to remove the "no do-overs" constraint that's always made video riskier than other forms of content. They also get into the mechanics of running your own business: what to delegate, what to keep for yourself, and how to stay connected to the work that actually energizes you instead of just the work that keeps the business running.

Episode Highlights

Effortless Is the Hardest Thing to Make: Itai and Alex compare good video production to watching Roger Federer play tennis, the more natural it looks, the more work went into it.

No More Reshoots: Itai walks through how AI is changing iteration in video, letting his team regenerate a style frame instead of re-shooting an entire scene.

Naive vs. Expert: Alex and Itai debate whether building a big business requires knowing nothing about your market, while building a small, sustainable one requires knowing it intimately.

Delegate the Craft, Keep the Vision: Itai explains why he's pulled back from hands-on production to focus on strategy, AI transformation, and business development, and how founders scale by defining their role from the inside out.

Front-Load Your Relationships: Alex and Itai agree that the relationships built earliest in a career compound the most, and are often what create opportunities decades later.

Full Chapter List

(01:59) Welcome and Introduction
(02:41) Itai's Origins: Zanesville, Ohio to Northwestern Film School
(05:21) How Fondu Was Born During the Pandemic
(09:19) Building a Remote, Distributed Creative Team
(13:16) The Full Production Process: Concept to Final Cut
(20:27) How AI Is Changing Iteration in Video Production
(22:47) Naive vs. Expert: Building a Big Business vs. a Small One
(24:16) How to Start Creating Content on a Shoestring Budget
(37:22) Running a Business With No Boss
(43:11) Venture's Slow Payoff vs. Chasing Fast Outcomes
(45:31) Career Advice, Prioritization, and Front-Loading Relationships
(49:15) What Fondu Does and How to Work With Them

Links & Resources

Fondu: https://fondu.co/
Verissimo Ventures: https://verissimo.vc/
Alex Oppenheimer on LinkedIn: https://www.linkedin.com/in/alex-oppenheimer/
Itai Joseph on Linkedin: https://www.linkedin.com/in/itaijoseph/

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

Alex — Thu, 10 Sep 2026 17:52:50 +0300

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 up

Links & 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.

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

Alex — Wed, 09 Sep 2026 15:15:39 +0300

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 preview

Referenced: 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

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

Alex — Mon, 07 Sep 2026 18:40:21 +0300

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 decades

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/
Range by David Epstein

Next 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

The Physicist who Hacked Health - Yaron Hadad

Alex — Wed, 02 Sep 2026 14:50:14 +0300

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 Impact

Links & 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 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.

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

Alex — Mon, 31 Aug 2026 10:16:13 +0300

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.

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

Alex — Wed, 29 Jul 2026 14:18:49 +0300

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.

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

Alex — Thu, 16 Jul 2026 19:24:05 +0300

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 Quality

Links & 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

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

Alex — Thu, 02 Jul 2026 14:09:03 +0300

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=sharing
Unit 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.

Bet on yourself. Don't be someone's option bet.

Alex — Tue, 16 Jun 2026 11:16:42 +0300

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 walking away from a successful mid-market acquisition with nothing.

Alex breaks down the financial friction between early-stage and late-stage investing, why paper wealth metrics like MOIC are misleading, and why founders need a clean secondary strategy to protect their equity. It all comes down to one question: Are you running your own option bet, or are you somebody else’s?

Episode Highlights:

The management fee game. How venture capital mechanics can misalign a VC’s incentives with a founder’s outcome, allowing partners to build massive wealth on fees regardless of fund performance.

Clean slates vs recaps. A look at why the market aggressively floods money into unproven startups while leaving existing, operationally solid companies stranded if they carry historical valuation baggage.

The entry valuation trap. A breakdown of how over-paying on entry valuation or over-raising downstream triggers brutal liquidation preferences that wipe out founders and early seed investors at exit.

MOIC vs DPI. The critical difference between parading paper wealth and waiting for cold hard cash to hit the bank, and why great early-stage managers care about returning realized capital.

Running your own option bet. Why optimizing the middle path of $50M to $250M exits, focusing on sustainable revenue growth, and leveraging early secondary sales is the real playbook for building true generational wealth.

Links & Resources:

Substack Essay: https://alexoppenheimer.substack.com/p/thinking-about-writing-down-your

Medium Essay: https://medium.com/@Alexoppenheimer/are-recent-valuation-hits-as-unreasonable-as-they-seem-88f5ae789e92

LinkedIn Essay: https://www.linkedin.com/pulse/how-mess-up-good-company-make-any-money-along-way-alex-oppenheimer/

Verissimo Ventures: https://verissimo.vc/

Follow Alex on LinkedIn: https://www.linkedin.com/in/alex-oppenheimer/

About Very True:

No Easy Answers: A Founder’s Reality Check on the LLM Boom

Alex — Thu, 04 Jun 2026 16:56:04 +0300

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 Isaac break down why vertical SaaS moats are shrinking, the critical difference between deterministic and probabilistic AI architectures, and the structural threat automation poses to traditional entry-level career paths.

It is a gritty, honest look at why the rules of technology and career growth are fundamentally shifting, and why there are no easy answers for founders or the next generation of builders.

Episode Highlights

[04:21] The Macau Arbitrage & Choosing the Right Table: Isaac explains how his time playing professional poker in China shaped his startup philosophy. It is always better to find an uncrowded, highly lucrative table than to try to be the absolute best player in a hyper-competitive room.
[22:07] Auditable vs. Probabilistic AI: Why generic LLMs fall short in corporate finance. Isaac outlines the necessity of "Auditable AI," which provides deterministic systems with complete traceability, as opposed to the probabilistic guesswork of foundational language models.
[28:30] Corporate Gerrymandering: Alex breaks down his concept of "corporate gerrymandering," which is the fracturing of companies into highly artificial, arbitrary line-item roles, and explains how AI is systematically dissolving these operational inefficiencies.
[40:09] Shifting Economic Premiums: A look at how traditional baseline white-collar skills are losing their market premium and why specialized accounting, law, or radiology work will increasingly be viewed as a historical "art form."
[52:12] The Core Instinct Crisis: Alex and Isaac tackle the generational gap left behind when AI automates entry-level tasks like basic data input or syntax coding, and how future executives must build their critical thinking skills without the traditional corporate ladder.

Links & Resources

Trullion: https://trullion.com
Verissimo Ventures: https://verissimo.vc/
Isaac Heller on LinkedIn: https://www.linkedin.com/in/isaacheller/
Alex Oppenheimer on LinkedIn: https://www.linkedin.com/in/alex-oppenheimer/

About Very True

What Actually Is Enterprise Software Anymore? with Roy Rubin of Magento

Alex — Wed, 27 May 2026 20:15:54 +0300

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 the AI layer, exploring whether the new wave of vertical AI startups are actually just glorified system integrators (VARs). They discuss the lost art of customer-funded growth, why application software got so expensive to build, and the "premium valuation" dynamics between systems of record and work methodologies. They also get tactical about the build-vs-buy dilemma, sharing why both of them recently decided to code their own AI-agent-driven portfolio management systems rather than just writing checks.

Episode Highlights

[09:15] Customer-Funded Growth: Roy breaks down the "old-school" approach of letting your customers fund your business, contrasting it with the modern venture treadmill of fabricated valuation targets.
[13:33] The True Cost of Software: Alex questions the billions spent on R&D for application-layer SaaS and discusses David Sacks's "burn multiple" as a truer measure of operating efficiency.
[18:03] The Valuation Premium: Why companies that function as both a system of record and a work methodology historically capture the highest multiples in the public and private markets.
[23:49] The "VAR-tical" AI Era: Are vertical AI platforms true tech products, or just an enterprise sales channel (and system integrator) for underlying models like Claude and OpenAI?
[30:22] VCs Who Code: Roy and Alex discuss building their own internal operating systems to manage portfolio data, and why AI agents are changing the way non-technical founders can build software.
[43:23] Startups vs. Incumbents: Roy's take on why legacy enterprise players hold the advantage in distribution and data, and where early-stage founders should actually be placing their bets.

Full Chapter List

[00:00] Introduction: What Actually is Enterprise Software Anymore?
[02:24] Roy's Background: From Israel to LA, the IDF, and Freelance Coding
[05:06] The Early Days of E-Commerce & Discovering Open Source
[08:14] Building Magento: Customer-Funded Growth vs. Venture Capital
[10:48] Unpacking the Magic and Margins of the SaaS Business Model
[13:33] Burn Multiples and R&D Bloat in Application Software
[18:03] Systems of Record vs. Work Methodologies
[22:48] The Open Source Strategy & Building an SI Ecosystem
[23:49] "VAR-tical AI" and the Commoditization of the Wrapper
[30:22] VCs Building Software: Custom Portfolio OS and AI Agents
[38:27] Historical Technology Adoption vs. Modern Execution
[41:14] The Allure of "Boring" Picks and Shovels Businesses
[43:23] Final Thoughts: The Future of Startups vs. Incumbents

Links & Resources

R2 Ventures: https://www.r2vc.com/
Verissimo Ventures: https://verissimo.vc/
Roy Rubin on LinkedIn: https://www.linkedin.com/in/royrubin/
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.

All ARR Taste Like Chicken with Elliot Comite

Alex — Wed, 29 Apr 2026 17:08:40 +0300

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 the "Single Pane of Glass" philosophy, why all ARR "tastes like chicken" when you're looking at a P&L, and the grit required to move from analyzing businesses to actually running them.

Episode Highlights

[15:16] The Three Faces of Finance: Elliot breaks down the three roles of a growth-stage operator: hiring for the Past (Accounting/Controls), the Present (Operating/FP&A), and the Future (Strategy/Capital Markets).
[20:42] The Single Pane of Glass: Why the finance lead is the only person in the company with a truly objective view of reality, and how to use that "canonical text" to align an executive team.
[27:43] Decoding VC Psychology: A candid look at the "Default ADHD" of venture capitalists and how their herd mentality and academic pipelines influence the way they evaluate your business.
[41:10] The 5-Bullet Point Rule: How to survive the fundraising "shot clock" by distilling your business into the five key bullet points that actually end up in an investment memo.
[49:07] The "Just Win Baby" Principle: A lesson from the Al Davis school of management on why top-tier investors will often ignore "perfect comps" to simply win the deal when they see a winner.
[56:58] Defining the Strategy: Elliot’s final word on the finance leader as a "simplification engine" who helps the entire organization see the path from today to five years out.

Full Chapter List

[00:00] Introduction: 10 Years of Friendship & Shared Philosophies
[02:11] From Growth Equity to Building: Why Investing Wasn't Enough
[03:52] The Art + Science + Teamwork of the Company Side
[05:15] The Ironclad Journey: Scaling Software for 5,000-Year-Old Processes
[06:05] Bringing Tech Infrastructure to Real Estate at Perchwell
[09:36] Being "Deep in the Sauce": Why Building is Energizing
[11:21] Defining the Job: Everyone's Role is Enterprise Value
[15:16] Hiring the Past, the Present, or the Future
[17:52] Billionaires vs. Jail: Creative Finance vs. Creative Accounting
[20:42] Why All ARR Tastes Like Chicken
[25:00] The Unbundling of the Venture Capitalist: Deals vs. Sourcing
[27:43] The Psychology of the Board: Managing "Hawks"
[38:17] Narrative Control: Defining the Problem for Your Investors
[41:10] Fundraising Tactics: Avoiding the Gross Margin Rabbit Hole
[49:07] Managing Stakeholders & The "Just Win Baby" Principle
[52:59] Career Advice: Why VCs Make Surprisingly Good Salespeople
[56:58] Closing Thoughts: The Fun and Terror of Startups

Links & Resources

Perchwell: https://www.perchwell.com/
Verissimo Ventures: https://verissimo.vc/
Elliot Comite on LinkedIn: https://www.linkedin.com/in/elliotcomite/
Alex Oppenheimer on LinkedIn: https://www.linkedin.com/in/alex-oppenheimer/

Turning Ambient Restlessness into Productivity Through Movement

Alex — Wed, 15 Apr 2026 21:29:54 +0300

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 the exhausted, drained feeling of a YouTube rabbit hole with something that actually feels like an accomplishment.

This one is a departure from the usual startup and finance conversations on Very True, but the underlying framework of awareness, calibration, and turning a liability into an asset will feel very familiar.

Be sure to check out the substack here: https://alexoppenheimer.substack.com/p/the-focus-spectrum

Episode Highlights:

Introducing Ambient Restlessness: Why your brain's constant need for stimulation isn't a character flaw, and how to redirect it instead of white-knuckling your way through a deep work session you're not ready for.
The Focus Spectrum: From mountain biking at 100% locked-in to lap swimming as moving meditation, Alex maps out how different physical activities demand different levels of cognitive load and what that means for what you pair with them.
The Two Failure Modes: Why listening to an emotional audiobook while descending at 30mph is as unproductive as sitting on the couch trying to focus. Finding the sweet spot is the whole game.
Muted Sessions & Baseline Awareness: The underrated practice of going out in silence, not to be productive, but to understand where you actually are so you can make better decisions about what you're capable of.
Adding a Layer to Deep Work: Alex respectfully pushes back on the "distractions are evil" framing and proposes a semi-distracted state as a legitimate, powerful mode, especially for people who need creativity before they even know what to do deep work on.

Links & Resources:

Olo Meditation App: https://www.olo.app
Get a free WHOOP and one month free when you join with my link: https://join.whoop.com/312F8912
Cal Newport's Deep Work: https://calnewport.com/books/deep-work/
Cal Newport's Slow Productivity: https://calnewport.com/books/slow-productivity/
Substack: https://alexoppenheimer.substack.com/p/the-focus-spectrum
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.

From 10 Employees Down to 3: Scaling Sales, Search, and Social with Matt Pru of Stackmatix

Alex — Tue, 31 Mar 2026 17:30:00 +0300

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 "Sales, Search, and Social" framework every technical founder needs. They discuss why hyper targeted Meta ads are a thing of the past, the rise of Answer Engine Optimization (AEO), and why raising too much money without a validated marketing engine is one of the fastest ways to kill your company.

Episode Highlights:

[04:22] Scaling Down to Scale Up: Matt details how Stackmatix operates with just three people, handling more revenue today than when they had a 10 person team, by leveraging automation, globalization, and AI.
[05:44] The B2B vs. B2C Divide: Why B2B companies traditionally ignored marketing until Series B, while B2C companies have always relied on it to survive, and how those paradigms are shifting.
[11:38] The Evolution of Meta Ads: From demographic targeting to AEO (Answer Engine Optimization), why hyper targeted Facebook ads do not work like they used to, and how the algorithm actually works today.
[20:33] Sales, Search, and Social: The three critical pillars of go to market that every founder must understand from day one, regardless of their technical background.
[37:26] The Series B Trap: Why raising too much venture capital without an efficient, validated marketing funnel is one of the quickest ways to kill your business.
[39:19] The Better, Faster, Cheaper Model: Matt's philosophy on why AI is not a silver bullet for quality, but a necessary tool for speed and cost efficiency when paired with human judgment.

Full Chapter List:

[00:00] Introduction and Matt's Trajectory from MightyHive to Stackmatix
[04:22] The Three Phases of Agency Evolution: Globalization, Automation, and AI
[05:44] A History Lesson in Startup Marketing: B2B vs. B2C
[09:36] Targeted Advertising and The Reality of Meta Ads Today
[18:24] The Power of Being a First Mover in the AI Era
[20:33] The GTM Playbook: Sales, Search, and Social
[27:49] When to In House vs. Outsource Your Marketing
[34:48] Agency Horror Stories and the Dangers of Overspending
[37:26] Why Raising Too Much Money Kills Companies
[39:19] Redefining the Modern Agency with AI and Automation
[47:10] Closing Thoughts: Exploiting Channels and the Grind of GTM

Links & Resources:

Stackmatix: https://www.stackmatix.com/
Verissimo Ventures: https://verissimo.vc/
Matt Pru on LinkedIn: https://www.linkedin.com/in/mattpru/
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.

The Compounding Tax - What Sustained Stress Actually Costs You

Alex — Wed, 25 Mar 2026 10:06:03 +0200

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 psychological taxes of an activated nervous system, you can stop compounding the damage, recognize when taking your hands off the wheel is your best move, and find genuine ways to recover.

Episode Highlights:

The Biological Cost of a Stress Event: Why a single siren or stressor actually costs you an hour or more. Alex explains the cortisol and adrenaline spike, and why trying to immediately bounce back into deep work or sleep is a losing battle against your own biology.
The Math Nobody Does & The Social Cascade: What happens when you run a stress deficit for weeks. Alex discusses how losing your "buffer" leads to a sharp uptick in interpersonal conflict, and why everyone needs more grace exactly when nobody has any left to give.
The Decision-Making Tax: How sustained duress degrades judgment. Drawing on research and his own experience as an investor, Alex explains why analytical capacity remains while calibration fails, and why the non-decision is often the smartest decision you can make.
Release Valves, Traps, and Hobbies: Finding a place to put the pent-up energy. Alex explores the fine line between exercise as a coping mechanism and exercise as an additional stressor, the underrated restorative power of deeply absorbing hobbies (like watch collecting), and giving yourself permission to just not be productive.

Links & Resources:

Read the full essay on Substack: The Compounding Tax
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.

From 140-Hour Banking Weeks to 45-Minute AI Deep Dives

Alex — Tue, 17 Mar 2026 19:57:59 +0200

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 allow the world to understand its value. He shares a behind the scenes look at the Facebook IPO, explains why he won’t "put lipstick on a pig," and demonstrates live how AI has collapsed 30 hours of M&A work into a 45 minute strategic session.

Episode Highlights:

[16:40] Lipstick on a Supermodel: Alex’s philosophy on "massaging the numbers"—why you can’t deceive the market, but you must find the most rigorous, nuanced lens to communicate why a great business is great.
[22:10] Collapsing the Stack: A look at the "Coordination Tax" of traditional banking versus the 2026 reality where a solo performer with a "jetpack" of AI can outperform an entire analyst class.
[07:12] The Translation Layer: Why tech banking is fundamentally about being a translator between founders who live the product and buyers who need to understand it in financial terms.
[28:30] Live Case Study: Alex walks through a real time exercise using Gemini to deconstruct a 10K, find hidden synergies, and build an acquisition pitch that can double a company's exit value.
[44:15] Preempting the Objection: How founders can use AI to analyze investor transcripts, identify "lazy questions," and grab the narrative by the horns before the meeting even starts.
[52:00] Smooth Curves for Smooth Brains: A masterclass in "massaging" data through visualization—why the right chart type and the right axis can make a complex conclusion jump off the page.

Full Chapter List:

[00:53] Introduction: The Crux of a Career
[02:45] What is Investment Banking, Really?
[05:22] Lessons from Morgan Stanley: Michael Grimes & Marcy Vu
[08:50] The Facebook IPO: Inventing New Methodologies
[11:15] The Coordination Tax: Horizontal vs. Vertical Teams
[16:40] Dealing with Data: Lipstick on a Supermodel
[19:20] The Rule of Being Actually Good
[22:10] Phase 3: The Solo Performer Evolution
[26:00] Doubling Acquisition Value Through One Realization
[30:45] 2026: The AI-Empowered Solo Performer
[34:10] Live Demo: Researching Synergies with Gemini
[38:40] The CEO’s Real Job: Capitalizing the Business
[41:15] Corporate Bloat vs. AI Efficiency
[44:15] Narrative Control: Using AI to Analyze Investor Feedback
[49:00] Communication as Lossy Compression
[52:00] Data Visualization: Smooth Curves for Smooth Brains
[55:40] Conclusion: Reach Out for a Deep Dive

Links & Resources:

Verissimo Ventures: https://verissimo.vc/
Alex Oppenheimer on LinkedIn: https://www.linkedin.com/in/alex-oppenheimer/
Q&A Submission Form: https://airtable.com/appK0BtRJHKzCwC55/pagt9qDFXPvBOIajF/form

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.

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

Alex — Thu, 12 Mar 2026 19:20:27 +0200

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 Prospects

Links & Resources:

Descript: https://www.descript.com/
Verissimo Ventures: https://verissimo.vc/
Ibrahim Cissé on LinkedIn: LinkedIn Profile
Alex Oppenheimer on LinkedIn: LinkedIn Profile

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

Alex — Mon, 23 Feb 2026 22:55:47 +0200

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.

Your Business Model Probably Sucks - Part 2

Alex — Mon, 16 Feb 2026 17:00:00 +0200

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/resources
Follow Alex on LinkedIn: https://www.linkedin.com/in/alex-oppenheimer/
Recommended Reading: The Most Important Thing by Howard Marks

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.

Your Business Model Probably Sucks - Part 1

Alex — Thu, 12 Feb 2026 14:00:00 +0200

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:
1. Independent Variables: The inputs you control.
2. Dependent Variables: The lagging indicators and outputs.
3. 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/resources
Follow Alex on LinkedIn: https://www.linkedin.com/in/alex-oppenheimer/
Recommended Reading: The Most Important Thing by Howard Marks

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

Alex — Thu, 05 Feb 2026 16:38:47 +0200

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.

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

Alex — Thu, 29 Jan 2026 16:33:57 +0200

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.

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

Alex — Wed, 14 Jan 2026 17:42:34 +0200

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.

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

Alex — Mon, 29 Dec 2025 16:27:33 +0200

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 Management and Fees
26:21 The Challenges of Fundraising and Founder Empathy
34:41 Navigating Ownership and Investment Strategies
39:45 The Importance of Check Size and Quality in Investments

From Craft Beer to Autonomous Checkout: Living Life in Chapters with Avi Moskowitz, CEO of PDQ

Alex — Mon, 22 Dec 2025 17:11:16 +0200

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."

Episode Highlights:

[00:00] Intro: Alex introduces Avi Moskowitz and his non-traditional path to Silicon Valley success.
[03:11] The Early Chapters: Growing up as the son of Holocaust survivors, early ventures in shoe shining, and bootstrapping an ISP during the internet's infancy.
[05:33] The "Shut Up" Method: A critical lesson in sales: carrying index cards in his pocket to remind him to listen twice as much as he spoke.
[10:27] The Beer Bazaar Story: How running a craft beer business in Israel and personally delivering hundreds of orders during COVID exposed the "trust gap" in e-commerce.
[13:50] The Amazon Standard: Why Amazon wins on boring logistics and predictability, and why most other merchants lose customers by failing to build confidence at checkout.
[18:37] Segmentation & Personalization: How PDQ uses over 1,600 data points to treat every customer differently—customizing offers, shipping, and badges based on real-time data.
[21:01] Autonomous Checkout: The future of e-commerce where AI manages unit economics and business strategy in real-time to save sales.
[36:40] Logistics as Marketing: Why the post-purchase experience (shipping, tracking, and delivery) is more important than the product itself for retaining customers.
[51:37] The "WISMO" Plague: Why 50% of "Where Is My Order" tickets are submitted the same day an order is placed, and what that says about the state of online trust.

Links & Resources:

PDQ Website: https://www.prettydamnquick.com/
Verisimo Ventures: https://verissimo.vc/
Follow Avi on LinkedIn: https://www.linkedin.com/in/moskowitzavi/
Follow Alex on LinkedIn: https://www.linkedin.com/in/alex-oppenheimer/

It’s Never a Straight Line: Why the Path to an Exit Often Starts with a Stop - Neri Bluman of XFunnel (acq by HubSpot)

Alex — Mon, 15 Dec 2025 16:48:01 +0200

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.

______________________________________________

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 Verismo, Alex sits down with Neri Bluman, co-founder of XFunnel (a Verissimo Ventures portfolio company), which was recently acquired by HubSpot.

Neri’s journey is a masterclass in resilience and self-awareness. He takes us from his early days as a lawyer-turned-operator to the hyper-growth rollercoaster of Avo, a logistics startup that scaled to 1,000 employees before facing the harsh reality of the market. After Avo, Neri did the unthinkable for a founder: he took a full year off to reset his nervous system.

We discuss how that break paved the way for XFunnel—a company built with a completely different DNA. Neri shares the specific playbook he and his co-founder Beeri used: prioritizing profitability over massive headcount, having the "money conversation" early, and targeting enterprise giants like Wix and HubSpot not just as customers, but as design partners.

In this episode, we cover:

The Generalist Superpower: Why being "good at everything but master of nothing" is a massive asset in the age of AI.
The Avo Story: The thrill of Y Combinator, the stress of logistics, and the hard lessons learned from a down-market cycle.
The Founder’s Break: Why Neri moved to Portugal, slept for months, and why you can’t "consult" your way to mental health.
The Co-Founder "Prenup": The crucial conversations Neri and Beeri had about lifestyle, financial goals, and ego before writing a single line of code.
Answer Engine Optimization (AEO): How XFunnel identified that the internet was moving from "blue links" to "direct answers" and built the tool to serve that shift.
The HubSpot Acquisition: How selling to enterprise customers early led to strategic partnerships and, ultimately, an exit.

Links & Resources:

The Frameworks You Need to Navigate VCs and Raise Your Next Round

Alex — Mon, 01 Dec 2025 16:33:00 +0200

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

Raising venture capital is challenging despite abundant funds.
Understanding the sales process is crucial for founders.
Different VC conversations require tailored approaches.
Emotional dynamics play a role in early-stage decisions.
Aligning with the right investors is key to success.
Junior VCs can be strong advocates for founders.
Market idiosyncrasies add complexity to fundraising.
Strategic planning is essential for effective fundraising.
Founders should focus on long-term investor relationships.
Navigating VC layers requires understanding their roles.

00:00 Navigating the Venture Capital Landscape
04:29 Types of Venture Capitalists and Their Decision-Making
10:31 Strategies for Engaging with Different VC Types
18:53 The Importance of Timing and Economic Alignment
26:23 Building Relationships with Junior VCs
32:20 Final Thoughts on Fundraising and Investor Relationships

The Career Advice I Wish I got in my Early 20s

Alex — Sun, 23 Nov 2025 12:00:00 +0200

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.

Your startup isn't actually worth its last private valuation

Alex — Wed, 19 Nov 2025 15:00:00 +0200

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

Why Companies Fail and Why I Started This Podcast

Alex — Sun, 16 Nov 2025 13:40:00 +0200

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!

Software as a Service or Service as Software? How AI changes the game for data tools with Gabi Steele, CEO of Preql

Alex — Wed, 12 Nov 2025 15:20:00 +0200

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.

Is zero revenue actually better than some revenue? Maybe...

Alex — Sun, 09 Nov 2025 15:44:00 +0200

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?

PLG & User Activation with Yaakov Carno of Valubyl

Alex — Thu, 06 Nov 2025 15:25:00 +0200

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? Wait, What Even is ARR?

Alex — Sun, 02 Nov 2025 16:10:00 +0200

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

Bifurcation of an Asset Class - October Verissimo Monthly

Alex — Wed, 29 Oct 2025 17:53:38 +0200

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/

How to be Wrong in Early Stage Venture

Alex — Sun, 26 Oct 2025 18:28:48 +0200

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

The Financial Operations Flow - Comprehensive Review

Alex — Tue, 21 Oct 2025 21:17:01 +0300

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

Engineering Architecture & Scaling Teams - It's All About Everything Series

Alex — Wed, 02 Jul 2025 15:23:46 +0300

🎧 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:

Michael Stoppelman, Former SVP Engineering at Yelp
Gustav Rydstedt, Chief Architect at Chegg, former CTO & Co-founder of Verbling
Moderated by Nitay Joffe, CTO & Co-founder of ActionIQ, Partner at Verissimo Ventures

💡 Key themes explored:

Staying hands-on as a technical leader
Building process without bureaucracy
Leading with both conviction and emotional intelligence
Embracing AI while maintaining core engineering skills

Understanding Your Legal Docs - It's All About Everything Series

Alex — Wed, 02 Jul 2025 15:19:53 +0300

🎧 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:

Mordechai Hartman – Principal at Hartman Venture Advisors PLLC
Josh Eisenson – Partner at Goodwin
Maria Kuehn – Head of Legal at ActionIQ
Moderated by Alex Oppenheimer – General Partner at Verissimo Ventures

Tax Strategies and Wealth Management- It's All About Everything Series

Alex — Tue, 01 Jul 2025 16:18:55 +0300

🎧 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:

Todd Saunders – (Moderator) CEO at Broadlume (recently exited)
Tres Evans – Managing Director & Private Wealth Advisor at Morgan Stanley
Robbie Shattuck – CEO & Founder of Athos Private Wealth
Aaron Bedrick – CEO & Founder of Symphony Strategies
Max Sabert – Private Wealth Advisor at UBS