Mike Cannon-Brookes

Co-Founder and CEO, Atlassian · 2 appearances on the record.

computed by AI from the episodes · how this works → · full disclaimer →

founderexecutiveinvestor@mcannonbrookes ↗LinkedIn ↗atlassian.com ↗Wikipedia ↗

He co-founded enterprise software giant Atlassian in 2002 alongside Scott Farquhar, scaling products like Jira, Confluence, and Trello globally. Outside of software, he is an active climate-tech investor known for backing Sun Cable and driving shareholder campaigns to accelerate decarbonization.

47statements → 17claims → 5claims resolved → 80%fully supported → 3.81/5average certainty → 2.34/5average debate potential → 4.1/5argument clarity · the sources → 83said about them ↓

4 supported 1 partly supported 0 contradicted 1 not yet assessed 11 not checkable as stated how the 17 claims stand · each chip opens the sources

10 predictions · 7 assertions · 7 opinions · 16 insights · 7 disclosures · every statement was checked. The predictions and assertions are the 17 claims: statements the public record can support or contradict. 5 are resolved, 1 is not yet assessed, and 11 name no date, number or outcome precise enough to check. Everything else (opinions, insights, what ifs, disclosures) can never be settled by the record, so it carries no assessment.

The record, in short

What the tape says about how Mike argues and how the claims held up. Everything they said, and everything said about them, is in the tabs below.

Their most notable supported claim

Assertion Supported

Cannon-Brookes: Some Atlassian AI features are 1,000x cheaper to run today

“Some of our features are a thousand times cheaper to run than when we introduced them today.”

Mike Cannon-Brookes Feb 12, 2026 ▶ 19:02 Anthropic's Super Bowl Ad: Who Won & Lost? | Sierra Hits $150M ARR: Is Customer Support Too Crowded? · 20VC with Harry Stebbings

Expressed certainty vs assessment result

none yet certainty 1

none yet certainty 2

100% certainty 3

100% certainty 4

75% certainty 5

weighted support: a fully supported claim counts one, a partly supported claim counts half. Each filled bar is clickable and opens exactly those claims; "none yet" means nothing said at that certainty level has resolved yet

Argument clarity: do they answer the question? how? →

4.1 / 5 directness 4.2 · coherence 4.3 · precision 3.8 · compression 3.5

redirected or did not address 2 of 38 assessed questions (5%). Watch them ▸

This is a score against a rubric. It is not a rank. Every host question → answer exchange is scored with names hidden on directness, coherence, precision and compression, 1–5 each, on meaning alone: disfluencies are ignored, and only raw unedited episodes count. This is the score that measures thought. Every scored exchange, scores shown → · The rubric and its checks →

How they sound: speaking style how? →

280 words/min while actually speaking · 12.6 um and uh per 1k words · 12.5 false starts per 1k · 27.2% of pauses land inside a clause

Measured by listening to the audio itself: 10,576 words across 1 episode of raw-level tape, transcribed verbatim with every um and uh kept, each one attributed only where the alignment onto our timed stream is unambiguous. These are measurements of speaking style. We do not rank them: across this corpus, fluency and argument quality are nearly uncorrelated (ρ≈0.2), and smooth talking does not signal clear thinking. How it's measured →

How the interview went all their pushback → series average →

Across 2 rated episodes:

host pushback ▾ 5/10

pushed back at the host ▾ 4.5/10

setup questions received 40%

host pushback: the hardest questions Harry asked, tap to play ▶ 7:41“Do you not think that consulting services pie actually goes up?” ▶ 29:25“So why do you think we should give up on TAM?” ▶ 29:27“Just because it goes from 200 to 600 doesn't mean we should give up on TAM.” ▶ 10:39“When I reflect on your last 18 months, respectfully, and I hope this isn't rude of me, it's probably the most aggressive, but also obvious example of, like, founder mode in action.…” ▶ 21:16“When I hear you talk about the centrality of design there, I think about Satya Nadella's statement Business applications will collapse right in the agent era. They are essentially …” ▶ 38:19“If this is true that switching costs is actually incredibly low, are these fundamentally good businesses?”

when Mike pushed back ▶ 11:00“I'm gonna violate the old media rule, never disagree with journalists, but you said you're not a journalist, that's all right.” ▶ 49:34“I don't know that I think unconstrained is useful. I'm not trying to challenge the question either. I, I think unconstrained thinking is not particularly useful, right?”

What they said47 What others said83 Episodes2

Everything Mike Cannon-Brookes said on 20VC that made the record, most notable first. Filter by type, assessment or year in the ledger →

Opinion

Cannon-Brookes: The idea that software is dead is ludicrous

“The idea that software as a category is dead is ludicrous to me.”

Mike Cannon-Brookes Feb 12, 2026 ▶ 0:00 Anthropic's Super Bowl Ad: Who Won & Lost? | Sierra Hits $150M ARR: Is Customer Support Too Crowded? · 20VC with Harry Stebbings

Insight

Cannon-Brookes: Technology's fundamental role is to change and expand TAM

“Our whole job in technology is to change TAM, actually.”

Mike Cannon-Brookes Feb 12, 2026 ▶ 29:53 Anthropic's Super Bowl Ad: Who Won & Lost? | Sierra Hits $150M ARR: Is Customer Support Too Crowded? · 20VC with Harry Stebbings

Opinion

Cannon-Brookes: VCs back OpenAI at huge valuations for logo marketing

“One thing that they don't say is a lot of VCs want the loose side on the wall, so when you walk into the office, on the wall is a nice logo that says, oh, you invested in OpenAI. You invested in Anthropic. Well, if you put money at three hundred fifty billion,…”

Mike Cannon-Brookes Feb 12, 2026 ▶ 1:00:17 Anthropic's Super Bowl Ad: Who Won & Lost? | Sierra Hits $150M ARR: Is Customer Support Too Crowded? · 20VC with Harry Stebbings

Opinion

Cannon-Brookes: Being public makes Atlassian a better company

“We're a better company because we're a public company. Like we have become a better business, right? We're better at forecasting. We're better at planning. We're better at executing.”

Mike Cannon-Brookes Feb 12, 2026 ▶ 1:11:59 Anthropic's Super Bowl Ad: Who Won & Lost? | Sierra Hits $150M ARR: Is Customer Support Too Crowded? · 20VC with Harry Stebbings

Prediction Not checkable as stated

Cannon-Brookes: Most tech assets are currently vastly overvalued

“One of the only predictions I think I would make accurately is 10 years from now, we'll look back and say, man, you remember that era? That was crazy. Most of the things are vastly overvalued.”

Mike Cannon-Brookes Oct 13, 2025 ▶ 0:05 Atlassian CEO, Mike Cannon-Brookes on Why Everything is Overvalued & Are We in an AI Bubble · 20VC with Harry Stebbings

Prediction Open · timeframe Oct 2030

Cannon-Brookes: Atlassian will employ more software engineers in 2030

“Five years from now, we'll have more engineers working for our company than we do today. More software developers working for our companies. We will create far more. They will be more efficient.”

Mike Cannon-Brookes Oct 13, 2025 ▶ 26:47 Atlassian CEO, Mike Cannon-Brookes on Why Everything is Overvalued & Are We in an AI Bubble · 20VC with Harry Stebbings

Insight

Cannon-Brookes: Co-CEO success requires equality in age, life stage, and equity

“Having two equal parties, I think, in motivation, experience, we've always talked about this, is a really important part of what made it successful. And by equal, yes, equal, I don't know, shareholding-wise, equity-wise, but equal in terms of age, life stage, …”

Mike Cannon-Brookes Oct 13, 2025 ▶ 4:05 Atlassian CEO, Mike Cannon-Brookes on Why Everything is Overvalued & Are We in an AI Bubble · 20VC with Harry Stebbings

Opinion

Cannon-Brookes: Outlier AI Winners Will Outweigh Overvalued AI Losses

“Most of the things are vastly overvalued, probably true. Some of the things will be worth far more and are undervalued, and the far more is probably overweight all of the things that are overvalued, like as classically happens, right?”

Mike Cannon-Brookes Oct 13, 2025 ▶ 14:46 Atlassian CEO, Mike Cannon-Brookes on Why Everything is Overvalued & Are We in an AI Bubble · 20VC with Harry Stebbings

Insight

Cannon-Brookes: Anyone claiming to know AI's long-term business model is lying

“Where the monetary value and the fundamental value lies on the far end of it, in terms of how the business models shake up, if you think about the search era and advertising and all these things, right, I don't think that's known. I think anyone who tells you …”

Mike Cannon-Brookes Oct 13, 2025 ▶ 15:49 Atlassian CEO, Mike Cannon-Brookes on Why Everything is Overvalued & Are We in an AI Bubble · 20VC with Harry Stebbings

Prediction Not checkable as stated

Cannon-Brookes: Specialized apps won't be replaced by a single AI agent

“I don't think we know in the AI era if all those apps just disappear into some godlike Siri agent that we just talked to. I, I'm not a believer in that world view. I don't think it's likely to happen. I do think AI is going to have to change all of those appli…”

Mike Cannon-Brookes Oct 13, 2025 ▶ 22:51 Atlassian CEO, Mike Cannon-Brookes on Why Everything is Overvalued & Are We in an AI Bubble · 20VC with Harry Stebbings

Prediction Not checkable as stated

Cannon-Brookes: Tech industry will hire far more entry-level software engineers

“I think we'll have far more of them. Maybe that's a bold bet.”

Mike Cannon-Brookes Oct 13, 2025 ▶ 32:01 Atlassian CEO, Mike Cannon-Brookes on Why Everything is Overvalued & Are We in an AI Bubble · 20VC with Harry Stebbings

Opinion

Cannon-Brookes: Atlassian won't pay 10x for AI tools without 10x productivity

“No, probably not. I mean, maybe if they gave me 10 times the productivity.”

Mike Cannon-Brookes Oct 13, 2025 ▶ 35:14 Atlassian CEO, Mike Cannon-Brookes on Why Everything is Overvalued & Are We in an AI Bubble · 20VC with Harry Stebbings

Prediction Not checkable as stated

Cannon-Brookes: Proliferation of AI software will scale startup services tenfold

“If you have far more technology, you're going to have, instead of running, I don't know, say you're a medium sized startup and you have a hundred different services running, you're going to have a thousand services. So the permutations and combinations and fin…”

Mike Cannon-Brookes Oct 13, 2025 ▶ 36:54 Atlassian CEO, Mike Cannon-Brookes on Why Everything is Overvalued & Are We in an AI Bubble · 20VC with Harry Stebbings

Insight

Cannon-Brookes: Enterprise AI deployment will take longer than expected

“The speed with which AI can be understood and deployed successfully by companies, customers, is something that is going to take a lot longer to really play through. Because the delta between magical demos and actual value delivered is quite high in a lot of ca…”

Mike Cannon-Brookes Oct 13, 2025 ▶ 58:41 Atlassian CEO, Mike Cannon-Brookes on Why Everything is Overvalued & Are We in an AI Bubble · 20VC with Harry Stebbings

Assertion Supported

Cannon-Brookes: Some Atlassian AI features are 1,000x cheaper to run today

“Some of our features are a thousand times cheaper to run than when we introduced them today.”

Mike Cannon-Brookes Feb 12, 2026 ▶ 19:02 Anthropic's Super Bowl Ad: Who Won & Lost? | Sierra Hits $150M ARR: Is Customer Support Too Crowded? · 20VC with Harry Stebbings

Assertion Partly supported

Cannon-Brookes: Atlassian gross margins increased over the past six quarters

“Our cogs has gone up, or rather cogs has gone down, right? Our gross margin has gone up. Last six or seven quarters.”

Mike Cannon-Brookes Feb 12, 2026 ▶ 19:12 Anthropic's Super Bowl Ad: Who Won & Lost? | Sierra Hits $150M ARR: Is Customer Support Too Crowded? · 20VC with Harry Stebbings

Disclosure

Cannon-Brookes: Only four public CEOs remain from 2020 SaaS peer group

“In COVID in 2020, we formed a group of SaaS CEOs. I think there were 16 of us that got together, we'd meet on Zoom every single week, right? At one stage, 10, 11 of us were public, maybe more, we all had earnings calls, and you know, it was a really good thera…”

Mike Cannon-Brookes Feb 12, 2026 ▶ 24:28 Anthropic's Super Bowl Ad: Who Won & Lost? | Sierra Hits $150M ARR: Is Customer Support Too Crowded? · 20VC with Harry Stebbings

Insight

Cannon-Brookes: Software engineering is output-constrained as roadmaps never end

“The difference with something like software or engineering is it's creation, right? It's how much can you make, right? The roadmap is never finished. You can keep creating more.”

Mike Cannon-Brookes Feb 12, 2026 ▶ 43:40 Anthropic's Super Bowl Ad: Who Won & Lost? | Sierra Hits $150M ARR: Is Customer Support Too Crowded? · 20VC with Harry Stebbings

Opinion

Cannon-Brookes: Public software firms neglecting AI R&D are in trouble

“I would argue if you're a public company today and you're not spending a lot of money on fundamental kind of new R&D around AI and your product category, you're probably in trouble.”

Mike Cannon-Brookes Feb 12, 2026 ▶ 1:10:13 Anthropic's Super Bowl Ad: Who Won & Lost? | Sierra Hits $150M ARR: Is Customer Support Too Crowded? · 20VC with Harry Stebbings

Insight

Cannon-Brookes: Spending 100% of your time working causes worse decisions

“I think if you spend a hundred percent of your time at work, you make worse decisions.”

Mike Cannon-Brookes Feb 12, 2026 ▶ 1:22:16 Anthropic's Super Bowl Ad: Who Won & Lost? | Sierra Hits $150M ARR: Is Customer Support Too Crowded? · 20VC with Harry Stebbings

Disclosure

Cannon-Brookes: Atlassian decided early on against training foundational AI models

“Firstly, very early on, we thought there would likely be multiple foundational models that were competing. And hence we've built our technology to be multi-model on purpose in almost every way, and that we were not going to make foundational models. It's unlik…”

Mike Cannon-Brookes Oct 13, 2025 ▶ 18:33 Atlassian CEO, Mike Cannon-Brookes on Why Everything is Overvalued & Are We in an AI Bubble · 20VC with Harry Stebbings

Prediction Not checkable as stated

Cannon-Brookes: AI interfaces will evolve far beyond simple chat boxes

“I don't believe the world will just end up as a chat box. Otherwise, we'd all just use the terminal on our computers, but it is an entry point, and so there's a lot of foundational design being done, really fascinating, good design all over the place.”

Mike Cannon-Brookes Oct 13, 2025 ▶ 20:05 Atlassian CEO, Mike Cannon-Brookes on Why Everything is Overvalued & Are We in an AI Bubble · 20VC with Harry Stebbings

Insight

Cannon-Brookes: Design becomes the primary software moat as AI explodes output

“There will certainly be far more software. It's probably a fairly safe assumption. Far more technology. What differentiates it is probably how it feels and how it works. And that's very hard to copy, right?”

Mike Cannon-Brookes Oct 13, 2025 ▶ 20:32 Atlassian CEO, Mike Cannon-Brookes on Why Everything is Overvalued & Are We in an AI Bubble · 20VC with Harry Stebbings

Prediction Not checkable as stated

Cannon-Brookes: AI Software Will Not Dynamically Regenerate Every Screen Interface

“In theory, AI can generate some code, write the code to create a new interface for every single screen you look at, right? I don't think we'll probably see that. It'll be too discombobulating for users. They'll get lost. They'll be like, wait, everything's mov…”

Mike Cannon-Brookes Oct 13, 2025 ▶ 24:10 Atlassian CEO, Mike Cannon-Brookes on Why Everything is Overvalued & Are We in an AI Bubble · 20VC with Harry Stebbings

Show 23statements(23 left)

The other half of the tape: Mike Cannon-Brookes's own voice is left out of every number here. Other people bring the name up 81 times in 26 episodes on 20VC. 2 statements on the record name them. every mention, with the transcript →

Who brings them up most Harry Stebbings 31 Jason Lemkin 15 Scott Farquhar 9 Jeff Lawson 6 Miles Clements 5 Rory O'Driscoll 2 Jean-Michel Lemieux 2 Heather Fernandez 2

Statements about Mike Cannon-Brookes, by other people (2)

Opinion

Clements: Never bet against Atlassian co-founder Mike Cannon-Brookes

“Never bet against Mike Cannonbrooks. Absolutely not.”

Miles Clements Mar 9, 2026 ▶ 41:48 "Cursor is Dead" is Total BS: Here is Why | Miles Clements · 20VC with Harry Stebbings

Prediction Not checkable as stated

Lawson: Atlassian and Mike Cannon-Brookes will stay aggressive on acquisitions

“So I think Mike will be one of the more aggressive on the acquisitions front because they've always been and so I think it's in the DNA of Atlassian, so I do think we are looking at one of those, even if I am not fully on board with the most recent.”

Jeff Lawson Sep 11, 2025 ▶ 1:10:05 OpenAI’s $10BN Secondary Sale, Ramp Hits $1BN ARR & Brex Hits $700M · 20VC with Harry Stebbings

Every mention by year

mentionsepisodesper episode tap a year for its mentions

2026 36 mentions in 15 episodes 2 per episode

"Cursor is Dead" is Total BS: Here is Why | Miles Clements · 20VC with Harry Stebbings Mar 9, 2026 · 13 mentions · from 30:53
Thrive Raises New $10B Fund | OpenAI Buys OpenClaw | Stripe at $140B: Is Adyen Wildly Undervalued? · 20VC with Harry Stebbings Feb 19, 2026 · 6 mentions · from 17:33
Canva Slashes Growth | Talent Exodus at Google | Revolut's $50B CEO Package | Musk's $55B Terrafab Aug 12, 2026 · 3 mentions · from 27:15
Anthropic Raises $30BN at $900BN Price | SpaceX Files S1: How Does it Trade | Cerebras Smashes Day 1 · 20VC with Harry Stebbings May 21, 2026 · 2 mentions · from 18:26
Citrini Research Breakdown: Agents, "Ghost GDP", Consumer Spend | Figma Earnings Beat · 20VC with Harry Stebbings Feb 26, 2026 · 2 mentions · from 22:47
Anthropic Buys Compute From Elon & Commits $200BN to Google | Cerebras IPO | Ramp Raises at $40BN · 20VC with Harry Stebbings May 14, 2026 · 1 mention · from 22:03
Anthropic's Raise & What It Means for Potential IPO? Mag7: Google & Amazon Up, Meta & Microsoft Down · 20VC with Harry Stebbings May 7, 2026 · 1 mention · from 43:15
Anthropic Raises $45B but Falls Short on Compute & Thoma Bravo Hand Back Medallia Keys to Creditors · 20VC with Harry Stebbings Apr 30, 2026 · 1 mention · from 10:10
7 more episodes that year, every mention in 2026 →

2025 17 mentions in 5 episodes 3 per episode

OpenAI’s $10BN Secondary Sale, Ramp Hits $1BN ARR & Brex Hits $700M · 20VC with Harry Stebbings Sep 11, 2025 · 7 mentions · from 55:57
OpenAI's Multi-Billion Deal with AMD & Polymarket, Vercel and Supabase Raise Mega Rounds · 20VC with Harry Stebbings Oct 9, 2025 · 4 mentions · from 30:59
The Impact of H1B Visas on Startups in the US & NVIDIA Invests $100BN Into OpenAI · 20VC with Harry Stebbings Sep 25, 2025 · 4 mentions · from 1:24:41
Base44’s Founder, Maor Shlomo on How Vibe Coding Will Kill SaaS · 20VC with Harry Stebbings Nov 24, 2025 · 1 mention · from 12:02
OpenAI Restructuring: Who Wins and Who Loses & Mercor Raises $350M at a $10BN Valuation · 20VC with Harry Stebbings Oct 30, 2025 · 1 mention · from 1:05:00
every mention in 2025, scene by scene →

2024 2 mentions in 1 episode

Jean-Michel Lemieux: Three Product Decisions Every Team Needs to Make | E1129 · 20VC with Harry Stebbings Mar 20, 2024 · 2 mentions · from 4:34
every mention in 2024, scene by scene →

2023 21 mentions in 1 episode

Scott Farquhar: Founding Atlassian; How We Scaled to a $50B Valuation; The 4 Jobs of a CEO | E1070 · 20VC with Harry Stebbings Oct 9, 2023 · 21 mentions · from 0:23
every mention in 2023, scene by scene →

2021 1 mention in 1 episode

20VC: Why and How The Best Companies Build Economies Around Themselves, When, Why and How To Build Effective Partner/Channel Networks & The Power of Compounding Growth in SaaS with Jay Simons, General Partner @ Bond Jun 10, 2021 · 1 mention · from 27:22
every mention in 2021, scene by scene →

2018 2 mentions in 1 episode

20VC: Lessons From Scaling Trulia to IPO, How To Maximise Your Impact within Your Organisation and Why No One Is Ever 100% Ready For The Next Job with Heather Fernandez, Founder @ CEO @ Solv Aug 24, 2018 · 2 mentions · from 23:07
every mention in 2018, scene by scene →

2017 1 mention in 1 episode

20VC: Accel GP, Rich Wong on When Is The Right Time To Scale A Startup, Optimising Initial vs Follow-On Investment Decision-Making & The Globalisation of VC In Recent Years Dec 4, 2017 · 1 mention · from 5:41
every mention in 2017, scene by scene →

2016 1 mention in 1 episode

20VC: Rob Go @ NextView on WTF Is Seed Investing Today and Why Raising Too Much Money Can Harm Your Startup May 16, 2016 · 1 mention · from 0:53
every mention in 2016, scene by scene →

Appearances (2)

Episode	Date	Speaking time
Anthropic's Super Bowl Ad: Who Won & Lost? \| Sierra Hits $150M ARR: Is Customer Support To	Feb 12, 2026	35m
Atlassian CEO, Mike Cannon-Brookes on Why Everything is Overvalued & Are We in an AI Bubbl	Oct 13, 2025	45m

Mike Cannon-Brookes

The record, in short

Their most notable supported claim

Expressed certainty vs assessment result

Argument clarity: do they answer the question? how? →

How they sound: speaking style how? →

How the interview went all their pushback → series average →

Statements about Mike Cannon-Brookes, by other people (2)

Every mention by year

Appearances (2)

Turn any episode into a week of clips.