Verissimo Monthly - June 2025
The Founder Expiration Point
Thoughts on Investing and Starting Up
As a startup scales, something strange happens. The challenges don’t just grow, they compound. What starts as a tight, fast-moving team building a product turns into a complex organism with politics, legal exposure, edge-case customers, investor drama, hiring headaches, and pressure to "scale leadership."
In short: the emotional weight and headaches increase exponentially, not linearly.
At the same time, your ownership, the thing that made it all worth it in the early days, is shrinking. Even as your company’s valuation climbs, your personal equity utility curve starts to taper off. It’s now a smaller piece of a bigger pie, buried beneath a heavy liquidation preference stack and under rising board pressure. A personal $15M paper gain at Series A can feel thrilling. A marginal $50M of theoretical value at Series C (with 150 employees, 6 board members, 1,000 customers, and $80M of liquidation preference) - not so much if it costs you two years of stress, cortisol, and deferred life plans.
While the theoretical reward starts to flatten out, the risk and the stress both continue to increase non-linearly.
This leads to a predictable intersection point, what we call the Founder Expiration Point.
It’s the moment when the emotional cost starts to outweigh the economic upside. When you look at the road ahead - the next board meeting, the next 50 hires, the next midnight fire drill - and think: “The next $100M in company value just isn’t worth my next 2 years… I have $25M of equity on paper, but I’m still renting an apartment and I am exhausted.”
At that point, founders can typically do one of three things:
Step back or bring in outside leadership.
Sometimes planned, sometimes quiet. Sometimes announced as "becoming executive chairman."Push for secondary liquidity.
If the equity can’t pay you emotionally, it better start paying you financially. We are big proponents of this approach. When big funds come in with big money, they are swinging for the fences. In order to maintain alignment between the founders and big money, founders need to be able to make the mental shift from playing defense/surviving/getting to the next stage, to swinging for the fences. That shift only happens from a position of personal financial stability (i.e., start playing with house money). This doesn’t mean massive $100M generational-wealth secondaries but rather $2-5M secondaries that take the pressure off and let founders live a bit closer to what everyone else seems to think they are worth.Mentally check out.
They’re still there in body, but the spark is gone. Execution suffers. Culture drifts.
You can think of this dynamic as two intersecting curves:
The Tolerance Curve: how much pain you're willing to absorb.
The Equity Utility Curve: how much marginal personal value you're getting from your ownership.
Where they cross, that’s the expiration point.
Not every founder hits it. Some grow with the company or have boundless energy and are willing to sacrifice it all. Some bring in a great COO early. Some get lucky with timing, market, or team. But for many, especially repeat founders, this moment comes sooner than outsiders expect. For investors, this is where it all comes back to the main reason you invested: the people. Pay close attention to what is going on in their world, how they look, how they talk, and figure out solutions to maintain alignment using the tools at your disposal.
Happy Fourth of July!
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Programming, Events, Content & More
🎙 Podcast Feature:
Very True by Verissimo
Check out Verissimo’s new podcast, Very True by Verissimo, where we spotlight our It’s All About Everything founder series. Hosted by the Verissimo team, each episode features candid conversations with early-stage founders, operators, and investors shaping the future of tech. From behind-the-scenes startup stories to honest takes on scaling, fundraising, and staying resilient, Very True by Verissimo offers a real look at what it takes to build something bold.
🎧 Episode 1: Understanding Your Legal Docs
🎧 Episode 2: Tax Strategies and Wealth Management
Tech on the Rocks
Tune in to Verissimo’s Nitay Joffe, and Kostas Pardalis founder of Typedef, as they chat with tech geniuses on Tech on the Rocks - where hardware, cloud, and all things future-tech meet over a virtual drink!
🎧Episode 19: How Cloudflare Reinvents Serverless at Global Scale with Josh Howard
Portfolio Highlights
Typedef recently announced $5.5M in seed funding. The round was led by Pear VC, we participated along with Monochrome Ventures, Tokyo Black, and several angels.
Typedef is a serverless engine that helps teams run large-scale AI workflows, like summarizing documents or classifying support tickets, without building fragile, custom infrastructure. Today, many LLM applications rely on ad hoc scripts to chunk text, manage rate limits, call the models, and store results. It works, for a while, but quickly becomes brittle and expensive at scale. Typedef replaces that mess with a single declarative job: it handles batching, retries, cost caps, and output storage automatically, turning generative AI into something you can trust in production
Mixus announced a $2.6M pre-seed round, and we were proud to participate alongside Hannah Grey VC, Liquid 2 Ventures, OVTR, EverywhereVC, and FullCircleFund.
Mixus embeds AI agents into your team's workflow, blending the speed of leading models with the critical oversight of human expertise. It turns tasks that took hours into seconds, without sacrificing reliability, by addressing the demand for AI agent verifiability and control, making these tools accessible and safe for everyone.
Clara Health lets teams build HIPAA-compliant AI automations in chat, tailored to their business, with help from a network of AI experts and partners. Customers include major home-care providers in the US.
OurRitual is modernizing relationship support with a blend of expert guidance and personalized digital tools. While therapy has become more accessible, couples often lack affordable, tailored options. By combining weekly sessions with self-guided app experiences, OurRitual makes it easier for partners to build stronger, healthier relationships.
Who we are
Verissimo Ventures is a Pre-seed and Seed Venture Fund based in Israel and the US. We invest primarily in enterprise software companies and take a fundamentals-driven approach to early-stage investing. We work closely with founders to help them build the strongest, most fundamentally sound businesses with potential for explosive growth and a meaningful impact on the market.
We were founded in 2020 and are currently investing out of our $26M Fund 2.