Monday, September 21, 2026
Startups
The AI backlash was always going to come — what nobody predicted was that it would come first from the generation born into the technology
The assumption seemed bulletproof. Gen Z — digital natives raised on Siri, Alexa, and algorithmic feeds — would be AI’s...
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The Weekly Notable Startup Funding Report: 4/20/26 – AlleyWatch
The Weekly Notable Startup Funding Report takes us on a trip across various ecosystems in the US, highlighting some of...
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There’s a specific kind of person who volunteers the embarrassing story about themselves before anyone else can bring it up, and it isn’t self-deprecation. It’s copyright. If they tell it first, they get to decide what it means.
Most people hear someone tell an unflattering story about themselves and assume it’s humility, or at worst, a small bid...
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The people who say they don’t care what others think are almost never telling the whole truth. What they actually did was move the audience inward, and now they perform for a private version of the same judges they claim to have escaped.
The man at the next table is explaining, with a kind of practiced lightness, that he stopped caring what people...
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The 27 Largest US Funding Rounds of March 2026 – AlleyWatch
March 2026 was a month of conviction-scale capital across the US startup ecosystem. Leveraging data from CrunchBase, I’ve identified the...
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Most men who grew up in the 1960s and 70s were taught that admitting you needed help was a character flaw. Finally, we are discovering that openness has its own kind of strength.
Here’s a stat that stopped me cold: according to the American Psychological Association, only about 1 in 3 men experiencing...
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Not everyone who avoids looking at their bank account is financially irresponsible. Some people grew up in households where money conversations preceded every serious conflict, and the avoidance is a nervous system trying to prevent a fight that already happened decades ago.
Money avoidance gets read as immaturity. The unopened banking app, the unread statement, the vague answer when someone asks how...
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Psychology says people who check on everyone else during a crisis before acknowledging their own fear aren’t selfless — they learned that being needed is the only form of safety their childhood ever reliably delivered
I was 24 years old, crawling out of an attic in Dorchester when the homeowner’s wife started screaming downstairs that...
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The Most Active Non-NYC Venture Capital Firms in Q1 2026 in New York – AlleyWatch
I analyzed recent venture funding data to identify the most active venture capital firms based outside of New York City...
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You will be forgotten by most people you know. Not because you didn’t matter but because attention is a resource and you are competing with every screen, every urgency, every crisis that isn’t you. The people who stay remembered figured out something the rest of us are still learning
Last week I ran into someone I used to work with at the consultancy. We’d shared countless lunches, inside jokes,...
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