Cailen D'Sa (@cailen) header
Cailen D'Sa (@cailen) profile picture

Co-founder @ Crew (https://teapawt.org/t.co/YGK6X1SWZI) - GTM Talent for the Top AI-Native Startups | Early @Dropbox @FrontHQ @Box @RevenueCat | Investor @retool @theZipHQ

United States
Joined November 2009
Photo by Cailen D'Sa (@cailen)Photo by Cailen D'Sa (@cailen)Photo by Cailen D'Sa (@cailen)Photo by Cailen D'Sa (@cailen)Photo by Cailen D'Sa (@cailen)Photo by Cailen D'Sa (@cailen)Photo by Cailen D'Sa (@cailen)Photo by Cailen D'Sa (@cailen)Photo by Cailen D'Sa (@cailen)Photo by Cailen D'Sa (@cailen)
Just met a company that vibe coded an entire CRM to avoid paying for HubSpot or SFDC over the last year. It’s now become a burden to maintain and missing key functionality / third-party interoperability as they scale… They’re now migrating to HubSpot. App layer is fine.
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Buy signal initiated
It is a stock-pocalypse
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Today is one of those days that remind you to be diversified ($LOW / $PEP / $HD)
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Cailen D'Sa retweeted
Millennials: The Rug Pull Generation. Study hard and you'll get a good job. 2008 financial crisis. Work hard and you'll own a home. Housing crisis. Build a career and enjoy stability. Gig economy and layoffs. Enjoy your prime years. Global pandemic. Save for your future. Inflation. Finally, AI might free us from working our lives away. Potential World War III.
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Cailen D'Sa retweeted
Every AI agent at work runs with the access of whoever set it up. That’s why security keeps saying no. Today we’re launching @mintive: every agent gets its own identity and permissions, the same way every employee does. We’ve raised $11M, with @cowboyvc leading our latest round.
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Zohran coming with receipts
Just last month, DoorDash couldn’t seem to find the money to pay their deliveristas — until our administration forced them to give back $131M+ in stolen wages and penalties. This week, they’ve managed to find $17 billion to acquire one of their main competitors. Corporate consolidation means higher prices, harsher exploitation, and greater economic inequality for New Yorkers. We’ve stood up to these giants before. That doesn’t stop now.
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Going to be fun to see people sell $GOOG for tax loss harvesting this year.
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Cailen D'Sa retweeted
As someone who has personally spent $500k / mo+ on Google Ads for years, I can tell you with certainty: This revenue growth in Search is artificial & extremely unhealthy for Google’s business long term Search volumes are declining as legacy search is being increasingly cannibalized by non-monetized LLM queries Google’s response? Manufacture revenue growth via short-sighted, highly extractive, customer-hostile tactics. I.e. charge advertisers more for lower quality clicks, including clicks they do not want and explicitly did not approve Google to charge them for A few examples to illustrate: For all of its history until recently, Google operated on a 2nd price auction model I.e. if you bid $5 CPC and the next highest bidder bids $1 CPC, Google charged you $1.01 for the click (one penny more than the 2nd highest bidder) rather than the $5 you bid This was a genius move by Google early on as it incentivizes advertisers to input their true maximum willingness to pay rather than trying to play the game of bidding low and constantly adjusting to try to stay just ahead of the next highest bidder while still not paying too much However recently, Google silently deprecated the 2nd price auction and began charging advertisers as much as their bid and budget caps allow, regardless of what anyone else is bidding It’s a short-sighted cash grab at the expense of the long term health of the advertiser ecosystem Making thing worse, Google also recently nerfed keyword targeting precision Google previously had precise keyword targeting settings that allowed advertisers pick individual search phrases to bid on, defined down to the character w/ exact match or phrase match targeting This was one of the core features that made search advertising magic, enabling advertisers to run extremely precise campaigns based on exactly what their target customer typed But now, even if you bid on a specific term or phrase using the strictest exact -match targeting settings, Google will show your ad across 1000’s of unrelated keywords, labeling them as as “exact match (close variant)” The definition of “close variant” means whatever they want it to and changes constantly. The result is advertisers get billed for clicks that are totally irrelevant to their business and that their targeting settings explicitly forbid Google from targeting. Google does it anyway and there’s no ability to turn this off So now exact match is broad match, and broad match is just meaningless spam This is all very bad for advertisers, but for Google, it allows them to show your ad and bill you for clicks across 1000x more searches that were previously going unmonetized (mainly because they’re garbage queries no one wants) This is how you grow revenue atop declining search volumes Lastly, and perhaps most egregiously, Google quietly stopped respecting budget caps by a factor of 2x. For example campaigns we’ve been running for years with $1000 daily budget caps suddenly began spending $2000+ per day And the extra spend is entirely on the garbage keywords Google arbitrarily throws in as “exact match (close variants)” which have no value to our business, but can’t be turned off Google offers no refunds nor any recourse for overspend or spend on keywords you explicitly did not target These are not the actions of a healthy business. These are the actions of company whose core business is in decline but desperately needs to pump quarterly earnings so Wall Street will continue to fund insane capex while hopefully looking through their rapidly deteriorating negative free cash flow Google operated a benevolent monopoly for the better part of 25 yrs Meaning the value Google captured from Search was but a small fraction of the value it created, and that spread produced a potential energy that justified expectations of high earnings growth far, far into the future This is now no longer the case At the alter of AI capex, Google is sacrificing the golden goose
Q2 was an amazing quarter, with our AI investments redefining what’s possible across every part of our business. Alphabet revenue grew 24% YoY and Google Cloud accelerated to 82% growth. We saw exciting momentum across the board from Search to YouTube to the Gemini app (which reached 950M monthly active users). Our model APIs are processing 22B tokens/min (up from 16B+ last quarter) driven by our workhorse Flash models. We’re also seeing great adoption of Gemini Enterprise, used by 90% of the Fortune 100, as well as strong demand for our security solutions. Outstanding results and momentum, and such an exciting moment—thanks to all of our partners and employees around the world! 🙌 About to hop on the call!
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Follow Buffet, they said.
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But yes, let’s go ahead and let Kalshi & Polymarket launch margin trading.
BREAKING: Louisiana man used credit cards to run up $88,716 in FanDuel bets
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There is no moat? CC: @GavinSBaker @jack
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😳
Brazil’s Stock Market Opens: -19.5%
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Increase the payout weights in the comp plan and you’ll immediately see reps investing the time to learn and pitch. Most reps are coin-operated at their core; otherwise they would’ve gone into other functions.
Imagine struggling to grasp the basics of Slack’s sales motion and value prop. Never change, Salesforce.
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This same guy told you that $OPEN was going to $80/share and $TEAM was a short at $70 Be careful who you follow.
I traced all 32 Wingstop store numbers ever listed under Rick Ross's family's Boss Wings companies in Wingstop's own state filings. End-2016: 21 open. End-2025: 1, in Clarksdale. 28 now listed under other franchisees. No price or reason appears in any filing.
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PSA: the companies asking you to 996/997 are the same people getting rich off secondaries on the way up then relegating you to the zombie co after a non-exclusive licensing deal
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I love how so many people on FinTwit are shocked when a company up 2000% in the last 12 months drops 10% after good earnings. The psychology of humans is interesting.
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Looks like the bottleneck bros have found a new bottleneck. How to deal with the margin calls.
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The sequel to the Covid Market Crash incoming.
PREPARE YOUR BUY BUTTON
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Overnight success: I’ve been using 1Password since 2009
1Password passes $500M in ARR, up from $400M in November 2025, driven by enterprise AI coding assistants and agents, and announces 1Password for Agents (@eschisgall / Wall Street Journal) (Visit Techmeme dot com for the link and full context!)
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I don’t care how talented you are as a product leader & visionary. You can never out-innovate interest rates.
It is difficult to exaggerate the amount of damage done to $OPEN shareholders since @nejatian became CEO (down 85%)
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