Repeat startup CEO and Founder. Lover of wine and watersports. Dad. Tweets are my own.

San Francisco, CA
Joined October 2007
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Replying to @AlaskaAir
@AlaskaAir - I am no longer a fan. 2 night in a row stuck in Seattle bar cause you cancel the flight to Santa Rosa at the last minute. Literally as we’re boarding the plane the 2nd time.
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Replying to @perplexity_ai
@perplexity_ai - your Black Friday flow is broken. Buying an M3 Macbook Air. On the Mac, selecting any other memory or storage config just ends up with a spinning cursor. On iPhone, putting the same credit card info ends up with error messages.
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No one is going to "kill" Salesforce. Hell, ACT is still around from the 80s, and doing hundreds of millions in revenue. People still use Siebel. But SFDC is definitely vulnerable from the bottom.
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If you look at every decade since the 80s, there's been a new player that's ended up taking a big chunk of the space by capitalizing on technology shifts. The 2020s will be no different.
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I have great respect @Benioff and the team there, but they are very vulnerable in the small-to-medium business market, and have too much tech debt to change anything at the core quickly.
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Replying to @lessin
LLMs are great for dealing with unstructured data like emails and transcripts, but not (currently) great at translating natural language into SQL queries and vice versa for returning the deterministic answers necessary for things like forecasting. @coffee_crm is tackling both. @salesforce will, of course, say they’re solving everything, but only by selling you another add-on to an already overcomplicated and overpriced stack that’s focused mostly on large enterprises. I know - I was previously the GM of Sales Cloud.
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You’re a fucking infant.
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😂😂😂😂😂😂😂😂😂
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Replying to @bhalligan @HubSpot
I’d still take it as a positive. It’s not like you’re sitting still…
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Replying to @AerLingus
@AerLingus - you have a plane full of very cranky passengers on flight 61 sitting on the tarmac at SFO. Let's get them to the gate.
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Replying to @auren
I’ve heard good things about Attio, but ideally want a single system for sales, support and marketing, so Hubspot or Salesforce are better fits.
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Replying to @Benioff
Too early to call checkmate. And the demo was not real time (written prompts given, voice-overs added later). Still an amazing demo, though. – at Menlo Park, CA
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I think the simplest explanation for the @OpenAI drama is a simple power struggle. Sam tried to remove a board member. She retaliated by trying to remove him. And brought whatever evidence she could of wrongdoing to support her case. #killorbekilled. CC @DavidSacks @Jason @chamath @friedberg – at San Francisco, CA
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And I think @btaylor’s announcement about his board role being transitional isn’t at all surprising. 1) He lived through the great Twitter clusterf%*!k of 2023 and probably doesn’t want to ever relive that and 2) he’s started his own company (no doubt centered around AI) and could likely be in a conflict of interest situation. @DavidSacks @Jason @chamath @friedberg – at San Francisco, CA
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Replying to @airspeedhq
@airspeedhq has been crushing it since we released our apps on @SlackHQ. Total game-changer for customer acquisition and engagement. Thank you @Benioff
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Replying to @Jason
WHEN YOU STARTED SHOUTING IN ALL CAPS
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Replying to @lochhead
@lochhead sounds like we need to do a road trip in drag. 😂 – at South San Francisco, CA
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I know you did important things in the past, but now you’re just a grumpy old man yelling at kids from the porch, @RalphNader. You don’t have a clue about entrepreneurship. – at South San Francisco, CA
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Replying to @dosberg
SwagUp – at Sausalito, CA
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