Stephen Messer
@smesser

Big Data, Analytics, Networks

 NYC
collectivei.com
Joined March 2007
15 Photos and videos
Article

Value Venture Capital.

Name the value-venture-capital version of @sequoia . There isn't one. Name the @a16z of value venture. Also not one. Twenty-five years of this discipline applied to primary tech venture and the people

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Stop calling founders serial

@pmarca is a serial investor. @bhorowitz is a serial investor. @sama is a serial investor. @naval is a serial investor. @rabois is a serial investor. @DavidSacks is a serial investor. @bgurley is a
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The Arc of a Company's Life Now Fits Inside a CEO's First Term.

The Arc of a Company's Life Now Fits Inside a CEO's First Term Mark Leslie mapped the corporate life cycle in 2015 with a decade of tolerance built in. In 2026 the tolerance is twelve to eighteen
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Article

When AI Learns to Feel.

The room is arguing about the wrong AI. Sign the letter. Slow the models down. Save us from superintelligence. It's a great story, and it lets everyone off the hook, because the AI that should
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Article

The SaaS Debt Trap.

Marc Benioff borrowed $25 billion to buy his own stock. He cannot run that trade twice. Here's the sequence. In March, Salesforce issued $25 billion in senior debt and ran the largest accelerated
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The Hypothesis Company

Your lawyers lied to you. Every time you asked about AI, they told you to be cautious. Wait for the liability picture to clear. A few hallucinated citations made headlines, and they used those stories
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AI-First rivals are 50x faster than you. Your team's gut is why. This piece fixes that.

Your buying committee: 11 people, 11.5 months to close. Your AI-first rival: one person, one week, same decision. That's a 50x speed gap on the identical class of decision, and it's the reason a small
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Article

The One Thing AI Can’t Fake

Our AI at Collective[i] got good enough at predicting deals that people stopped arguing with it. A deal it called won, won. A deal it called dead, died. Then we found the deals it couldn't explain. A
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Your gut was your edge. AI just turned it into a weapon of mass destruction.

Two facts, same week. Only one moved a stock price. Salesforce jumped roughly 20 percent on August 27, its second-best trading day since going public in 2004. A meaningful piece of that beat was a
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The Reason Prior Tech Bubbles Broke Just Got Fixed.

Every prior tech bubble broke when VC ran out of money. This one has $725 billion reasons it won't. Here's the best way I can explain why that number matters. My nephew is a fantasy football genius.
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Great podcast with @jackmyersbiz upnextpodcast.com/episodes/4…

426. Jack Myers. Judgment is Scarce. — The Up Next Podcast with Gabriella Mirabelli

Media ecologist and futurist Jack Myers joins Gabriella Mirabelli to explain why judgment, not intelligence, is becoming the scarcest resource inside organizations. The conversation traces how AI is...

upnextpodcast.com
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AI first disrupts your company in more ways than you think
Article

The Agent Swarm Just Killed Scale as a Moat.

Ukraine is not a war story. It's a training ground. For the first time in a century, we can watch, in real time, which organizational model wins when the cost of technology collapses and the speed of
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Ten Ukrainian Drone Operators Demolished a 16,000-Troop NATO Force in Half a Day. The Same Pattern Is Already Inside Every Industry You Invest In. Most CEOs Still Cannot See It. Part One of Two.

The West Just Got Destroyed. Your Company Is Next.

Sixteen thousand NATO troops from twelve countries just got destroyed by ten Ukrainian drone operators. In half a day. It happened twice. Once in Estonia in May 2025, during a NATO exercise called
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16,000 NATO troops. 12 countries. Destroyed by 10 drone operators in half a day. Twice, a year apart. Training had to be reset three times because the troops kept dying too fast to learn. This isn't a military story. It's already happening inside your industry, and most CEOs can't see it yet. reloadnyc.com/the-west-just-…

The West Just Got Destroyed. Your Company Is Next.

Ten Ukrainian Drone Operators Demolished a 16,000-Troop NATO Force in Half a Day. The Same Pattern Is Already Inside Every Industry You Invest In. Most CEOs Still Cannot See It. Part One of Two.

reloadnyc.com
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Stephen Messer retweeted
Dave McClure
@davemcclure
Aug 17
5 big problems why VC asset class doesn’t scale well: - no debt leverage - ⁠long only, can’t hedge - ⁠pref stack / deal complexity makes valuation difficult - ⁠perpetual board seats - ⁠limited VC/LP illiquidity great soundbite: random engineer at unicorn AI startup gets better liquidity via annual employee tender offer than investors/LPs see ReloadNYC.com @smesser

Artificial CommonSense

Thoughts on AI and the changing face on the global economy Artificial CommonSense Stephen Messer

reloadnyc.com
Dave McClure
@davemcclure
Aug 17
excellent piece on how VC is getting disrupted & scaling: reloadnyc.com/tech-is-not-an… by @smesser
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Artificial CommonSense is now available across the social web, on @index@reloadnyc.com
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Was so fun to do this and I hope you all enjoy it youtube.com/watch?v=M9Nm4H5h…
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AI can automate the appearance of connection. It cannot automate trust. Gunil Chung and J. Kelly Hoey just broke down why authentic relationships are the scarce asset in an AI-first world. intelligence.collectivei.com…
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Time Kills All Deals. America's Permitting Process Is Killing Yours. reloadnyc.com/time-kills-all…

Time Kills All Deals. America's Permitting Process Is Killing Yours.

The same AI-native permitting that makes homeownership affordable again can bring manufacturing, industrial, and commercial development back to America without cutting wages, reducing protections, or...

reloadnyc.com
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The Last Great Head Fake in Software History. reloadnyc.com/the-last-great…

The Last Great Head Fake in Software History.

SaaS revenue is about to tick up. Analysts will call it a recovery. They will be wrong about what it means. The revenue comes first. The reckoning is sequential.

reloadnyc.com
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