Cailen D'Sa

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Cailen D'Sa

Cailen D'Sa

@cailen

Founder & CEO at https://t.co/ZW8z1JCt2g | Early @Dropbox @FrontHQ @Box @RevenueCat | Investor @retool @productboard @theZipHQ

United States เข้าร่วม Kasım 2009
1.3K กำลังติดตาม2.4K ผู้ติดตาม
ทวีตที่ปักหมุด
Cailen D'Sa
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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Jason ✨👾SaaStr.Ai✨ Lemkin
Honestly if Meta paid $14B+ to get the Alex + Scale team to reboot their AI strategy ... Someone should pick me and Amelia up for a mere $140m or so to help them with their AI Agent strategy It would be cheap
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Techsaleshackz
Techsaleshackz@techsaleshackz·
Decagon promoing sdrs to Ent AE Are we buying this or Is this a fake title
Techsaleshackz tweet media
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Cailen D'Sa
Cailen D'Sa@cailen·
@mkobach Don’t feel bad for them - it’s still trading at 7.7x NTM And employees had the ability to sell during lockup expiration when it was trading at 13x in mid December You have to know what you own.
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Matthew Kobach
Matthew Kobach@mkobach·
Figma employees got hit with the worst 1-2 timing punch ever. Should have had a huge acquisition exit from Adode, but then the global regulatory environment killed that deal. So they go public and hit a market cap 3x of the acquisition price, and everything looks up. Then AI makes massive strides in the 6-month post IPO lockup period and the stock drops -80%.
Matthew Kobach tweet media
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Cailen D'Sa
Cailen D'Sa@cailen·
@Kellblog Don’t feel bad for them - it’s still trading at 7.7x NTM And employees had the ability to sell during lockup expiration when it was trading at 13x in mid December You have to know what you own.
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Dave Kellogg
Dave Kellogg@Kellblog·
This to me is an example of why timing is so unfair. If you look at this from the prospectie of the long-term employee / company builder, how much money they make (if they can even sell at all) is so much a function of timing, it's horrific. One reason why I liked when companies went public much earlier because it provided with the builders with more control over when they wanted to cash out all or in part.
Matthew Kobach@mkobach

Figma employees got hit with the worst 1-2 timing punch ever. Should have had a huge acquisition exit from Adode, but then the global regulatory environment killed that deal. So they go public and hit a market cap 3x of the acquisition price, and everything looks up. Then AI makes massive strides in the 6-month post IPO lockup period and the stock drops -80%.

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Cailen D'Sa
Cailen D'Sa@cailen·
@buccocapital It’s like people saying they’re working when they’re doom scrolling LinkedIn
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BuccoCapital Bloke
BuccoCapital Bloke@buccocapital·
“It organizes your files” “It prioritizes your emails” “It tells you insights about your calendar” These are not real things. They are not making you more productive. It is making you an idiot Yes, AI is great. But this is fake productivity. This is dumb. You are being dumb
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Cailen D'Sa
Cailen D'Sa@cailen·
@johnloeber They trade at 9.5x revenue, and you’re acting like they’re dead.
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John Loeber 🎢
John Loeber 🎢@johnloeber·
I feel sorry for Figma. They pulled off a generational feat, maybe the best and most admirable of its era: 4-5 years of pre-launch toil on fundamental technology, using that to launch a highly disruptive product, doing what previously was unimaginable, creating one of the few truly good pieces of software of its time. But as so often, things get good just before the end: right now Figma is looking like a fitting capstone to the pre-AI software era.
Sheel Mohnot@pitdesi

Figma got crushed on this one :/ Anecdotally seeing more companies task design work to the product team already.

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Cailen D'Sa
Cailen D'Sa@cailen·
@JaredSleeper We were using the term “prosumer” dating back to 2010 at Dropbox. What’s old is new..
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Jared Sleeper
Jared Sleeper@JaredSleeper·
This is so true. The vast majority of the hypergrowth AI companies are built on prosumer-led growth... it is arguably the only way to have "best in class" growth today. They are either prosumer (Lovable, Replit, Cursor, OpenEvidence, Suno, Higgsfield, n8n, Claude, OpenAI), prosumer-like usage dynamics with enterprise SLA aircover (Abridge, Harvey, Cognition, etc.) or somehow derivative of the insane level of usage of/investment in the above (FAL, Temporal, Mercor, etc.). Doesn't mean there aren't great businesses that are being built the old-fashioned way (enterprise sales, heavy integrations, etc.) but it is just going to be hard for those businesses to keep up with the PLG of the above when a new model release can send usage absolutely vertical for a few months.
Nikita Bier@nikitabier

For the rest of the year, the word for everyone working at the frontier of AI will be: Prosumer

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Cailen D'Sa
Cailen D'Sa@cailen·
@harleyf Every startup I’ve met who uses them has had a terrible experience.
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Cailen D'Sa
Cailen D'Sa@cailen·
@haridigresses @Workday As a multi-time past admin of rippling, I can confidently say that they’re almost as bad as workday. Terrible UX / Support is god awful
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hari raghavan
hari raghavan@haridigresses·
This is the beginning of the end for @Workday. Charging for data use and egress is the sort of rent-seeking behavior that companies employ when they've run out of innovation DNA. Hey Workday — it's not *your* data, it's your *customers'* data, and they can do whatever they want with it. If you want to block the "parasites", maybe just build a better product instead of engaging in anti-competitive practices (hi @FTC!). If you think you command the same pricing power with @HiBob_HR and @Rippling nipping at your heels, you're in for a rude shock. And just wait until someone builds an open-source Workday (I would bet this is a thing in the next few years). PS: Rippling also exhibits similar (in fact, worse) closed-platform tendencies, and I think it's a big mistake. I hope they change this philosophy. Open ecosystems tend to win in the end.
hari raghavan tweet media
Garry Tan@garrytan

Recent earnings call, Aneel Bhusri of Workday says startups with AI agents are "parasites" This is what system of record incumbents really think of startups. The war is just beginning. The facts: the user data belongs to the users, not the incumbent software vendor.

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deep
deep@fs_newsletter·
@WisemanCap PT $150 lol. Never going above $100
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Kaushik
Kaushik@WisemanCap·
$TEAM attractive entry point amid 'overly bearish' valuation - Truist We had a call with TEAM to discuss the impact of the company's recent lay-offs, changes to the model, their outlook for FY26 & 27, and more. At current levels, we believe that the valuation reflects an overly bearish growth outlook for the company... We see an attractive entry point with shares trading at 3.1x EV/CY26E Sales, well below the peer average of 5.9x, despite Atlassian’s mid-teens subscription growth profile and an expanding enterprise footprint. The recent restructuring enhances visibility into margin improvement and creates a clearer path toward GAAP profitability, which we believe is underappreciated in the current multiple. We also believe that TEAM possesses unique enterprise data assets, including workflow, collaboration, and system-of-record metadata across Jira, Confluence, and JSM, that could drive incremental value in the AI era. While the company still needs to execute on cloud migrations and broader AI monetization, we see a more efficient cost structure, strengthened enterprise motion, and AI-driven product opportunities supporting multiple expansion over time. PT $150
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Cailen D'Sa
Cailen D'Sa@cailen·
@gokulr Since Atlassian did this, their stock crashed another 20% 😂
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Gokul Rajaram
Gokul Rajaram@gokulr·
Terminating founder/leadership 10b5-1 sales is a really strong signal of belief, even more than stock repurchases. ---- This morning (March 16, 2026), Intuit announced that it intends to substantially accelerate its share repurchases, by utilizing up to the $3.5bn that remains in its current authorization. In addition, Intuit's executive leadership team and company founder are terminating all outstanding pre​-​scheduled stock sale plans established under Rule 10b5-1. Intuit called out that it believes its current stock price is meaningfully misaligned with the company's fundamental value, and is pursuing these actions in alignment with that view. To put the plan into perspective, Intuit repurchased $1.8bn in Intuit shares in FY 1H26 (a 40% increase y/y), and if Intuit utilizes all $3.5bn remaining under the authorization, that would represent nearly double the buybacks done in FY25.
Gokul Rajaram@gokulr

Intuit’s distribution moat One of the most powerful moats for software is a proprietary distribution channel. Intuit has incredibly sticky and loyal mindshare and distribution among the CPA community. When I was doing my startup, I tried to use another accounting software, but my CPA forced me to cancel that other subscription and switch to Quickbooks. It was an eye opening attestation to the strength of their hold on CPAs. I think Intuit will be extremely hard to displace as the accounting platform of choice for SMBs.

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Cailen D'Sa
Cailen D'Sa@cailen·
@jasonlk But they said most people will pay less. The equivalent of the billionaire tax in SaaS
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Jason ✨👾SaaStr.Ai✨ Lemkin
Man Clay got SO much more expensive with new "better value" pricing. 2x-3x more for us, I think. When pricing gets more complicated, it almost always means it's also gotten more expensive. At least for most.
Jason ✨👾SaaStr.Ai✨ Lemkin tweet media
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Cailen D'Sa
Cailen D'Sa@cailen·
@p_millerd If you’re FIRE, you’re def not trying to live in SF. Much better spots
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Paul Millerd
Paul Millerd@p_millerd·
i know at least 2-3 people who are hoping for a layoff that work at meta many of these people are already FIRE (as long as they stop desiring a SF homeownership at least haha)
Paul Millerd tweet media
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