“Services” was a dirty word in venture until 5 minutes ago. Now, it feels like every VC firm has a thesis for why they’re investable in the era of LLMs. This is both exciting (because I think this view is correct) and amusing (because it became consensus overnight, like

One oddity downstream of market participants not understanding the cost of capital is the voodoo around customer LTVs and CAC payback periods. You’ve probably heard that companies should have an LTV:CAC of at least 3x, or that the “benchmarks” indicate “best-in-class” companies

Certain things that “just don’t make sense” (like many of the late-stage fundraises) are downstream of Silicon Valley’s “foie gras” problem: the set of perverse incentives, shared across many market participants, to stuff great companies with far more equity than they can

This is less a commentary on Harvey and more a commentary on the general phenomenon of best-in-class growth companies raising successive rounds at higher and higher valuations: most of these financings make no sense. Growth equity capital is very expensive. “Dilution is low” is

This is a story of why flows are often a bigger driver of valuation than fundamentals. The supply/demand dynamics in the private markets create a persistent, valuation-agnostic bid for top private companies: an order of magnitude more capital pointed at companies than the amount

The former often serves as LP marketing but is usually a symptom of deep insecurity and a desire to prove — to both themselves and the broader market — their intelligence and capabilities. It’s designed to give themselves agency and center themselves in the art of

It’s really challenging for operators to re-orient themselves away from building “normal” venture-scale startups to building the shape of company Yishan describes, because the Silicon Valley culture that nearly every founder today grew up in rewards duration-maxing and creating

When I voted in NYC this morning (PS 89 site in Tribeca), the polling workers gave me a ballot that had already been filled out -- for Zohran, of course. Gross incompetence from the polling workers at best. At worst, fraud designed to confuse voters in favor of their preferred

Leaving aside the differences between the two companies, there’s a broader point here: while both public and private investors have enthusiastically poured money into AI infrastructure businesses at sky-high valuations, they’ve had wildly different attitudes towards software

The idea that conservatives vote the way they do out of economic self-interest is a tired, pre-2015 critique. The potential consequences of Zohran’s election on the tax base/fiscal outlook for NY are obvious and problematic, but they aren’t the reason people like Bill find

No better time to announce that I’ve joined the Customer Value Fund than on the back of the news of the team’s work with Chainguard, one of the world’s leading security businesses. After spending time with hundreds of businesses as a venture investor and building one at Callin,

Financial nihilism, widespread mental illness, political violence, and AI psychosis are a scary combo. Many companies today fall neatly into two categories: those that accelerate these things and those that defend against them. Smart people should build the latter.

Stock-based compensation discourse always picks up when software falls out of favor with investors. We saw this frequently during the SaaS crash of 2022 and are seeing it again now as software names sell off due to the “AI kills software” narrative. Loud SBC discourse on X is

So much of the discourse around the challenges facing VCs focuses on the dynamic of “too much capital chasing too few deals” and the need for consolidation. Unfortunately, it misses the fact that the problem isn’t simply one of oversupply, nor one that consolidation alone can

One interesting model for the LLM war is to treat it like a dollar auction. It's unclear that the ever-increasing “bids” are worth the size of the steady-state economic prize given how fast-depreciating the models are. A lot depends on the overall macroenvironment and whether

The venture-backed, AI-enabled rollup was one of the hottest themes of 2024. There are reasons why building an AI transformation playbook and externalizing it via M&A is very exciting, even if it’s actually a terrible money-making strategy for most traditional VCs. Less

In 2023, nearly every software pitch was some “Copilot for X.” In the spring, on the heels of the Devin / Cognition launch, every founder began pitching “agents.” Now, as a natural extension of the agent wave, founders are pitching agentic labor replacements, arguing that

@taylor_jrj2012 Maybe, but its a pretty shitty business I think given the COGS for the forseeable future. @andrewziperski lays it out well here https://t.co/axqkPtufLx but I think you really gotta believe they can surpass GOOG on the other types of searches before GOOG nails answers