AI INVESTORS COMPLETE THREE-YEAR CYCLE FROM DOUBT TO ECSTASY TO REGRETAI'S EXPENSIVE PROBLEM: IT COSTS TOO MUCH TO DO TOO LITTLEAPOTEX PRICES IPO AT TOP, BETS MARKET LOVES GENERICSSEQUOIA'S DUAL-PRICE EQUITY: ONE VALUATION, TWO TRUTHSTRUMP DISCOVERS SOCIALISM, CALLS IT A 'BEAUTIFUL PARTNERSHIP'AI INDUSTRY BLAMES BEIJING FOR NOTICING ITS POWER BILLSBENCHMARK DISCOVERS GROWTH FUNDS, ONLY 20 YEARS LATEGOOGLE DRAFTS WATER GUIDELINES WHILE COMMUNITIES DROWN ITS PERMITSAI INVESTORS COMPLETE THREE-YEAR CYCLE FROM DOUBT TO ECSTASY TO REGRETAI'S EXPENSIVE PROBLEM: IT COSTS TOO MUCH TO DO TOO LITTLEAPOTEX PRICES IPO AT TOP, BETS MARKET LOVES GENERICSSEQUOIA'S DUAL-PRICE EQUITY: ONE VALUATION, TWO TRUTHSTRUMP DISCOVERS SOCIALISM, CALLS IT A 'BEAUTIFUL PARTNERSHIP'AI INDUSTRY BLAMES BEIJING FOR NOTICING ITS POWER BILLSBENCHMARK DISCOVERS GROWTH FUNDS, ONLY 20 YEARS LATEGOOGLE DRAFTS WATER GUIDELINES WHILE COMMUNITIES DROWN ITS PERMITS
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Gurley Bets $22M That Government Sales Hasn't Already Failed

Pursuit joins the storied tradition of startups convinced they've finally cracked the procurement code.

Pursuit, a startup dedicated to helping companies navigate government sales, just closed a $22 million Series A led by Mike Rosengarten, co-founder of OpenGov. The round includes Bill Gurley and Jack Altman, two names with enough credibility to make this look like a serious bet on enterprise software. It is not.

The premise is eternal: procurement is broken, therefore a smart software platform can fix it. This insight has motivated roughly 1,000 failed startups since the internet began. Government agencies have procurement rules because Congress wrote them. No Series A is rewriting federal acquisition regulations. Rosengarten should know this—OpenGov made $200 million in revenue partly by helping agencies comply with the very rules Pursuit intends to bypass.

The pitch writes itself: 'We've built a better mousetrap for B2G sales.' Translation: we have a database and a dashboard. Gurley and Altman are betting that this time—unlike every other time—the mousetrap works. Their confidence is touching. The government's glacial decision-making timeline will remain glacial. The amount of paperwork will not decrease. The margins, however, will vanish.

When Pursuit's burn rate catches up with its TAM assumptions in 24 months, we'll see if Gurley has any comments about the regulatory environment's role in the failure.

💀💀💀💀  Dumb Rating: 4/5 — Messianic Hubris
⚠ Satirical commentary based on real, publicly reported news. Not financial or legal advice.
★ From the Glossary
"B2G Sales"
The fantasy that selling to government entities is a repeatable, scalable process rather than a decade-long lobbying campaign disguised as a business model.
D

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