We were wrong about who Founders House is for

Things I'm learning from conversations inside Founders House and behind the scenes of actually building.

Author

Damian Tenuta
June 08, 2026

Hey it's Damian,

I'm still buzzing from opening week at Founders House. The energy has been incredibly high.

On Friday, we packed the room for an AI build night with Cursor and NVIDIA. One of the speakers asked who actually uses AI agents day to day. I looked around a room of CTOs, VC-backed founders, and some of the sharpest operators in the city. Not even half the hands went up…

We are still sooo early.

This week I’m writing about my key takeaways from our AI night and the sales playbook Cristina Ciaravalli shared during her GTM Masterclass (former number-one seller at two fintech unicorns).

I’m also including some early reflections on who Founders House is for (it’s changing). Let's get into it.

📆 On the Calendar

Last week at the House: TechWeek Recap

We hosted our first TechWeek as an open House, and the building did not stop. The quick recap:

Investing in Health & Wellness Panel from Founders House at 22 Vanderbilt

  • Morning wellness to open the day before the sprint.

  • Founders Run + Coffee through the city.

  • GTM Masterclass with Cristina Ciaravalli, our Founding Advisor and the former number-one seller at two fintech unicorns.

  • Investing in Health & Wellness panel with Jenny Liu (Crush It Ventures), Nate Kline (Cistern Capital), and Ken Lau (Red Sea Ventures).

  • AI build night with speakers from Cursor and NVIDIA, hosted with AIExperts.com.

Last week’s Founders Run. I’ve hosted every Tuesday morning for 3 years.

Two sessions people keep asking me about: Cristina's GTM masterclass and the AI night. The takeaways from both are below.

The culture that’s emerging

People ask who the House is for. In short, the people who can’t sit still.

When we started Founders House, Louisa and I envisioned it as a place for early-stage founders to come and build together. We wanted to keep it founder-focused (founders and 2-3 founding team).

But as we’ve been meeting potential members, it’s become clear it’s not about stage, gender, age, or where you're from. We have men and women from 20 to 65.

We’ve got the exited founder building their next company; the serial entrepreneur on her fifth company; the angel investor with a builder’s spirit; the 20-year-old college dropout who went through YC.

The common thread is curiosity and energy. High-agency. The ones who would rather build than watch. The ones who want to build longterm without sacrificing their health. And yes, I wouldn’t be surprised if they couldn’t sit still in class.

The CTO of a multi-million-dollar fintech came by this week and said something that stuck with me: "What can I pick up from that corner of the world? What could I be missing?" That's the through-line in almost everyone I meet here. The most successful people I know are the most curious. They know they don't have it all figured out, and they want to be in the room where things are getting built. Not for status. To learn.

One of our founding members, an angel investor and wellness founder who'd just walked away from the PE firm he started, told me he hit a moment of "what am I doing?" and chose the more fulfilling path. I keep hearing versions of this. People with the title and the comp, trading it for something that actually pulls them.

It got me thinking about the value exchange in a room like this. What does someone who's already “made it” get from being around people still climbing?

It goes both ways: the ones who've “made it” pull energy and hunger from the people still climbing, and the young and hungry pulling late nights pick up perspective from the ones a few steps ahead. Put them in the same room and everyone walks out with more than they came in with.

That's the whole thing. It's not about status. It's about ideas and energy.

Growth through IRL, content, and AI

Back to Friday night. The night with Cursor, NVIDIA, and AIExperts.com. It was a packed room on a Friday, full of founders building instead of going out.

But the part I can't shake is that not even half of that room uses AI agents daily, and these are people who build for a living. The edge is still wide open. If you've been putting off actually using agents in your work, this is your sign. The gap between the people who use them and the people who only talk about them is about to get very large.

5 takeaways from the night you can use this week

Here's what I'd actually take home from Cursor, NVIDIA, and AIExperts.com.

A packed room on Friday night at 7pm to learn all things agents.

  1. Start in plan mode, not build mode. Adam from Cursor's first tip: before an agent writes anything, make it pull in context and ask you follow-up questions. The quality of what you get is set by the quality of the setup. Same thing when you delegate to a person.

  2. The bottleneck moved from doing to instructing. The real work now is context engineering: giving the agent the right level of information so it builds what you actually want. One of the attendees shipped a product to one of her biggest customers in about two days by feeding the agent MD files, screenshots, and a ticket it kept referencing so it never lost the thread.

  3. Make agents always-on, triggered by tools you already use. A Slack message or a pull request can kick off an agent on its own. Cursor auto-triages every code change as low, medium, or high risk, merges the low ones, and flags the rest for a human. Lucas from AIExperts runs hosted agents that keep working after his laptop closes: daily code review, a morning news digest, proactive pings. Pick one repetitive trigger in your week and put an agent on it.

  4. Delegate outcomes, not clicks. Name a workflow, then hire an agent for the job. Test whether an agent can do a real task you'd normally pay for, like support triage, bookkeeping, or content QA. If it can, that's a product or a service. The average knowledge worker loses around 32 days a year just hunting for the right piece of information. That's the opening.

  5. The moat is the harness, not the wrapper. Mahan from NVIDIA was blunt: most AI apps are thin wrappers on Claude or OpenAI. The value is building your own harness for a domain the big labs aren't focused on. And when you sell into a real company, the CIO doesn't care how slick the demo is. They want security and concrete ROI. Bring evals and numbers, or you're just another pilot that burns tokens and goes nowhere.

GTM takeaways from Cristina's masterclass

Cristina Ciaravalli ran the top sales seat at two fintech unicorns and now runs Valli Ventures. Her masterclass was the most tactical hour of the week. Here’s what I’m applying:

Cristina from Valli Ventures shares tactical insights on running GTM for startups.

  1. Sell a painkiller, not a vitamin. If you can't say what breaks when they don't buy, your positioning isn't ready. Find the one pain only you can solve. That's your wedge.

  2. Tier your accounts on day one. Without it, reps spray and pray and burn time on low-fit deals. Tier 1 gets custom everything, Tier 2 gets intentional outreach in batches, Tier 3 gets automated volume. Revisit it quarterly.

  3. Discovery is 20% talking, 80% listening. Open with a hypothesis about their problem, not a product overview. Ask what it costs them to do nothing, that's your urgency lever. Let the silence sit. The goal of the call is a second call, not a close. As she put it: no is second best, maybe is the worst.

  4. Watch the conversion between stages, not the top of funnel. If discovery-to-qualification is low, your ICP is wrong, you're talking to the wrong people. If qualification-to-negotiation is low, you haven't validated the pain or the buyer. If negotiation-to-close is low, your champion isn't selling for you when you're not in the room.

  5. Work backwards from the number, and exhaust warm intros first. $1M at a $50K average deal is 20 closes, about 80 deals in the pipe, 160 discovery calls, 3,200 contacts. Warm intros compress all of it. Her rule: work 100 warm intros before you go cold.

And one that's easy to forget: walking away from a whale can be the smart move. An 18-month deal with seven stakeholders and a custom build isn't a future customer. It's a current distraction.

A personal note

Four years ago I moved to New York and had no connections. I'm an introvert, which is a funny thing to admit as the guy who’s building a community. I didn't have a plan. I just liked running, so I started running through the city and inviting a few people along. That run became Founders Common. A few years, 20,000 people, and an amazing co-founder in Louisa later, it became Founders House.

Louisa and I instantly connected over bringing people together through wellness.

What people don't see is how much of it was content. Six months before we had a space, I posted a video about wanting to build a work and wellness club for founders. Someone who runs a private club in Midtown saw it, reached out cold, and that's how we ended up at 22 Vanderbilt. Money couldn't have bought the room. It was content and relationships.

What I've figured out is you don't build a room by being the loudest person in it. You build it by getting around people who are genuinely obsessed with what they're working on, getting out of their way, and showing up consistently enough that the right people find you. For me that's been about two hours a week on content. It's how I grew both my media company and this community, and it's the same system I’m walking through in a free live masterclass this Tuesday. If you want the system, come learn it.

How to join the community

If you're a founder who can’t sit still and wants to be around your people, apply to join Founders House → or book a day to come cowork →. We read every application.

Talk soon,

Damian