Founder Fridays No. 194
The Money Is Still Moving — Just Differently -- Agents Aren’t Copilots. They’re Replacements -- Fix the Room Before Diligence
Happy Friday.
I’ll be in the Bay Area next week click and would love to meet you. I’ll be hosting a happy hour on Wednesday night click here to sign up.
I’ll also be at the Praxis Summit. If you’re there shoot me a note. I’d love to say hi.
Q1 Startup Funding
Tech venture funding just rocketed from $5.3 billion to $36.2 billion in a single quarter, a nearly sevenfold spike that pushed total Q1 2026 capital to $39.9 billion across just 165 deals (the lowest deal count since 2016). Up rounds hit 86%, the first time they've cracked 80% since Q3 2022, and Series D and later pre-money valuations jumped from $1 billion to $2.5 billion in three months. The bifurcation is brutal though, Series B medians actually dropped from $195 million to $165 million, meaning capital is stampeding to anointed late-stage winners while mid-stage rounds get squeezed. If you're raising a Series B in 2026, you're competing against a market that's pricing your stage down 15% while writing checks 2.5x bigger one round above you, so sharpen your traction story or get creative with bridge structures before the gap widens. Cooley Go (5 min)
Agents Aren’t Copilots. They’re Replacements
Salesforce is now charging $2 per agent-completed call while Microsoft pushes Copilot at $30 per seat per month, and the gap between those two pricing models is the entire story of where enterprise AI value gets created. Per-seat productivity tools depend on rank-and-file employees actually changing how they work, but the original computing wave didn't make 1970s bookkeepers faster, it eliminated them, and executives bought in because the ROI was a brutally rational calculation on the bottom line, not a change-management gamble. That's why the most interesting AI bet right now is Palantir's ontology-driven Foundry approach, where years-long, top-down data integration engagements look like "back to the future" to SaaS investors who got addicted to organic, credit-card-driven adoption. If you're building in AI, stop pitching seat licenses to team leads and start pitching "seat-replacement" contracts to the C-suite, because the buyers willing to fund agent infrastructure care about replacing the 41% of wasted labor, not augmenting the workers doing it. Stratechery (8 minutes)
Infinite Supply Changes Everything
Every marketplace breakthrough in history — Uber, DoorDash, Indeed — came from unlocking a new form of supply. AI doesn’t just unlock more supply. In some categories, it creates supply that never sleeps, never has calendar constraints, and trends toward zero marginal cost. If your marketplace moat depends on supply scarcity, that moat is already eroding. The race to the bottom is real, but it only hits founders who mistake the AI tool for the business. The actual opportunity is positional: own the workflow before and after the transaction, not the transaction itself. Marketplaces that survive this shift will capture the awareness and consideration stages of the buying cycle — not just intent and purchase — turning search boxes into intelligent, personalized guides. The ones who don’t will watch take rates compress until the math stops working. This week, map your full demand-side workflow: what does your buyer do in the 30 days before they come to your marketplace, and the 30 days after? Pick one step in that pre- or post-transaction journey that currently happens off your platform and build or bolt on something that pulls it in. Even a lightweight AI tool that helps buyers scope, plan, or evaluate — before they transact — creates the high-frequency retention loop that makes downstream monetization inevitable. The goal is: demand comes for the AI, stays for the marketplace. Incumbents have the data and capital advantages, but they’re optimizing the existing transaction. The attack surface is the workflow around it. Founders who embed themselves in pre- and post-transaction behavior before incumbents notice will build switching costs that have nothing to do with supply depth or take rates — and everything to do with the fact that leaving means losing your whole workflow, not just your vendor list. NFX (7 minutes)
Founder FAQ: How Startups Board Members Can Be More Efficient?
Most founders treat their board like a quarterly obligation — prep the deck, survive the meeting, repeat. The counterintuitive reality: board performance is almost entirely a function of what the founder puts in, not who’s in the room. A weak board is usually a founder problem, not a director problem. The board meeting is the last place where real decisions should be made. By the time everyone is in the room, the outcome should already be known. Every major decision needs to be pre-sold one-on-one before it hits the table — not because you’re gaming the process, but because surprises in group settings create defensive reactions, not good thinking. The meeting is for ratifying, not debating. Before your next board meeting, call each member individually. Not to brief them — to ask what they’re seeing, what concerns them, what they’d push back on. Then send your pre-read 72 hours out, not 72 minutes. If you catch yourself thinking “I’ll just explain it in the meeting,” that’s the thing that’s going to derail the meeting. Resolve it on the call first. Founders who run their boards this way get something most don’t: board members who actually work between meetings. When a member feels genuinely consulted rather than periodically updated, they make introductions, flag risks early, and advocate internally at their own funds. The ones who feel like passive audience members do the minimum. The difference is entirely in how the founder runs the relationship — not in who they picked. Westaway (4 minutes)
Startup Funding Guides
I’ve put together a series of guides to equip founders to excel at fundraising. These guides break down the deal term-by-term and give you negotiation tips so that you can speak to investors with confidence.
Convertible Note: Guide / Video
Certainty in an Uncertain World
The startup journey is filled with uncertainty. A fractional General Counsel (GC) provides the certainty of on-call legal expertise. Having an experienced GC gives founders invaluable peace of mind. With a seasoned startup legal expert on demand, founders have a steady guide through uncertain legal terrain. The GC acts as a trusted strategic advisor while handling day-to-day legal tasks. This lifts a huge burden off of startup leaders, allowing them to focus on growth with legal confidence. Rather than getting bogged down in legal details, founders feel empowered delegating tasks to an expert and focusing on their vision. Founders sleep better knowing their GC can swiftly handle any legal issue that arises. If you’re curious how a fractional GC can give you peace of mind, let’s talk.