Day by Jay
Jackie DiMonte\ud83d\udcc8\ud83d\udcc9\ud83d\udcca
| Platform |  | Pricing | Only free issues | Publishes | Infrequently |
|---|---|---|---|---|---|
| Issues | 25 | Founded | 6 years ago | Last Issue | a month ago |
| Active | |||||
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jaydimonte.substack.comLatest Issues
The Right Conditions
There’s a graveyard of startups who were right about the future but wrong about the timing.
Webvan and Instacart both bet that consumers would buy groceries online. The difference between an $11B market cap and zero? About a decade.
It’s...
AI is coming for the jobs people actually like
We spend a lot of time talking about AI taking jobs. We spend almost none asking whether they are the right ones.
Before automated switching, there were telephone operators, plugging and unplugging cables into boards while supervisors time...
SaaS Was Never About the Software
Last week, $300B of SaaS market cap evaporated in a matter of days, marking the start of the SaaS-pocalypse. Naturally, AI was to blame. Never again will growth rates resume. Market sizes have permanently shrunk. The era of high-margin recu...
When Power Laws Collide, Incentives Do Too
VC has always been a power law business. But never more so than today.
Historically power laws described exits. Now, it’s about fundraising:
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12 firms collected 50%+ in the first half of 2025. It was 9 last year.
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63% of capital we...
AI Raises a Big Question, but Legacy Industries Have Already Answered It
AI is throwing venture investing into turmoil. Just look at DeepSeek’s bombshell. First, "GPT wrappers" were fragile; now, it’s the models themselves under question. And while hindsight is 20/20, our job is to predict outcomes today.
Soft...
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| Subscribers | Engagement | 63 | Monthly Web Visits | ||
|---|---|---|---|---|---|
| Accepts Sponsors | Estimated Cost per Ad | ||||
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Thoughts of the day, usually circulating around venture capital, engineering, and other frameworks
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