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Prediction Open · timeframe Sep 2030
Lawson: AI will decimate SaaS seat bases and human workflow roles
“The thing I would say though about any company in SAS today, and Atlassian is a Prime example of this is they are primed for, ah, disruption right now because AI is going to decimate their seat base for their products. It'll decimate the roles people are playi…”
Jeff Lawson Sep 11, 2025 ▶ 59:19 OpenAI’s $10BN Secondary Sale, Ramp Hits $1BN ARR & Brex Hits $700M · 20VC with Harry Stebbings
Opinion
Farquhar: AI startups without customer data move slower than incumbents
“If you're an AI startup and you don't have access to customer data and customers to test with, that can actually make you move slower.”
Scott Farquhar Oct 9, 2023 ▶ 26:57 Scott Farquhar: Founding Atlassian; How We Scaled to a $50B Valuation; The 4 Jobs of a CEO | E1070 · 20VC with Harry Stebbings
Insight
Lemkin: Bootstrapped SaaS startups risk falling behind venture-backed rivals
“Maybe it's not even until after five or ten million where if you don't have capital, you can't all be Atlassian or Qualtrics. Or, and they fall behind competitively. And I think that's the trap of the fallacy of the lifestyle-esque business, right? Where media…”
Jason Lemkin Aug 11, 2023 ▶ 32:24 DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings
Prediction Not checkable as stated
Reyes: AI will disrupt Agile methodology, challenging incumbents like Linear and Atlassian
“I will say, though, that one of the things that is pretty clear to me is that the way we build software is fundamentally changing, and I think that Agile might be one of the things that gets hit with this new way of developing, and that makes me think that the…”
Eno Reyes Aug 29, 2026 ▶ 1:21:29 Should American Enterprises Work With Open-Source Chinese Models? | Only 10% of Neo-labs survive
Prediction Not checkable as stated
Developer-focused SaaS seat pricing faces permanent assault from AI agents
“A lot of their revenue is still developer focused, which, where I think the seat is under assault, a permanent, permanent assault, the seat is.”
Jason Lemkin Aug 12, 2026 ▶ 1:24:35 Canva Slashes Growth | Talent Exodus at Google | Revolut's $50B CEO Package | Musk's $55B Terrafab
Opinion
Abrahami: Atlassian Is Vulnerable to AI Replacement by Developers
“And when I look at it at Atlassian, I think that the customers are the ones that are more likely to build things with code code, right? Because with code code, because they are developers, right? So I'm always in, in a bit of a concern there because I'm like, …”
Avishai Abrahami Jul 13, 2026 ▶ 9:10 Wix Founder: Will Base44 Win the Vibe-Coding Wars? | The Truth About the Economics of Vibe-Coding · 20VC with Harry Stebbings
Opinion
Lemkin: Atlassian and Monday threatened as AI agents bypass project tools
“The public markets have the right idea, but the wrong direction. The public markets think vibe coding and Claude are their threat. No, the threat is what the agents pick. And actually, if you look at overall, the markets are, they almost get it right. They're …”
Jason Lemkin Apr 30, 2026 ▶ 9:00 Anthropic Raises $45B but Falls Short on Compute & Thoma Bravo Hand Back Medallia Keys to Creditors · 20VC with Harry Stebbings
Opinion
Lemkin: Meta and Atlassian layoffs are voluntary, not financially forced
“Neither of these companies has to lay off anybody. Okay. Atlassian has substantial free cashflow meta. I don't know. They're in the, their free cashflow is dip, but it's still like in the mid forties, right? They don't have to do this.”
Jason Lemkin Mar 19, 2026 ▶ 10:27 NVIDIA Predicts $1TRN in Revenue: Everything You Need to Know From GTC & Anduril Lands $20B Contract · 20VC with Harry Stebbings
Opinion
Jason Lemkin: Atlassian is the single best public SaaS value pick
“As an armchair, if we're abstracting away from everything else, this is the best pick on the list because it, of the ones that have been beaten down the most, it's the one that's accelerating. None of the rest are accelerating. So if you had to be simplistic, …”
Jason Lemkin Feb 26, 2026 ▶ 1:13:55 Citrini Research Breakdown: Agents, "Ghost GDP", Consumer Spend | Figma Earnings Beat · 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
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
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
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 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
Lemkin: IPO markets evaluate efficiency at listing, ignoring capital raised history
“The IPO markets don't care. They actually don't care whether you raise nothing right in primary like Atlassian or whether you raised a crap load like rubric. Or whether you raised almost nothing like Klaviyo and then a bunch and then all, and then burn nothing…”
Jason Lemkin May 27, 2024 ▶ 44:27 Jason Lemkin: Why Pricing is Worse Than Ever and There is More Funding Than Ever | E1157 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Lemieux: Shopify prioritizes shipping on quality, while Atlassian prioritizes speed
“And I think the non-overlapping I saw the most from the inside was Shopify will ship on quality. Atlassian will ship on speed.”
Jean-Michel Lemieux Mar 20, 2024 ▶ 7:32 Jean-Michel Lemieux: Three Product Decisions Every Team Needs to Make | E1129 · 20VC with Harry Stebbings
Insight
Lemieux: Shipping software reduces risk far more than planning
“We've all been, I think, indoctrinated into planning reduces risk, and I think shipping reduces risk. So as a company, your job is to reduce the most risk possible. And I just really believe shipping does that.”
Jean-Michel Lemieux Mar 20, 2024 ▶ 20:51 Jean-Michel Lemieux: Three Product Decisions Every Team Needs to Make | E1129 · 20VC with Harry Stebbings
Opinion
Farquhar: Atlassian built a better product than Slack in many cases
“In, in many cases, I think against Slack, we had a better product.”
Scott Farquhar Oct 9, 2023 ▶ 16:57 Scott Farquhar: Founding Atlassian; How We Scaled to a $50B Valuation; The 4 Jobs of a CEO | E1070 · 20VC with Harry Stebbings
Insight
Farquhar: Doubling a 10-person engineering team yields zero net productivity gain
“And when you double that team, You actually don't get any more productivity because when you double the team, they now need to document things. They now need to work like, you know, separate the code out. They needed to start micro, you know, microservices and…”
Scott Farquhar Oct 9, 2023 ▶ 32:46 Scott Farquhar: Founding Atlassian; How We Scaled to a $50B Valuation; The 4 Jobs of a CEO | E1070 · 20VC with Harry Stebbings
Prediction Open · timeframe Oct 2028
Farquhar: Atlassian will never require employees to return to offices
“We made the decision that we would never require someone to come back into an office”
Scott Farquhar Oct 9, 2023 ▶ 27:47 Scott Farquhar: Founding Atlassian; How We Scaled to a $50B Valuation; The 4 Jobs of a CEO | E1070 · 20VC with Harry Stebbings
Assertion Partly supported
Farquhar: Accel won Atlassian's initial round at $405M valuation
“And the valuations we got back varied between, there was one sort of high hundreds. There was three of them ended up in the two to three hundred million dollar range. And Excel, who ended up you know, winning for us came back at four hundred and five million U…”
Scott Farquhar Oct 9, 2023 ▶ 12:39 Scott Farquhar: Founding Atlassian; How We Scaled to a $50B Valuation; The 4 Jobs of a CEO | E1070 · 20VC with Harry Stebbings
Disclosure
Farquhar: Atlassian's $10/Seat Model Is Less Vulnerable to AI Than $150+ Competitors
“If you're, you know, a 152 hundred dollars a seat, like you've got a much bigger pricing model change to worry about than if, like the last thing does, we charge 10 dollars a seat, and then how much is going to be augmented by AI versus replaced by AI.”
Scott Farquhar Oct 9, 2023 ▶ 38:54 Scott Farquhar: Founding Atlassian; How We Scaled to a $50B Valuation; The 4 Jobs of a CEO | E1070 · 20VC with Harry Stebbings
Insight
Howie Liu: Except Atlassian, Every Enterprise Product Eventually Needs Top-Down Sales
“Save for Atlassian, I think every great enterprise product eventually has to, you know, be sold to a senior, a strategic buyer, right? In the enterprise”
Howie Liu Aug 25, 2023 ▶ 33:04 Howie Liu: Decoding Airtable's $11B Valuation; The Impending AI Revolution in Enterprise | E1053 · 20VC with Harry Stebbings
Prediction Open · timeframe May 2027
O'Driscoll: Atlassian will never be a 5x or 10x AI growth company
“Taking it last, for example, I don't think it's like, it's not going to 10 X from here, right? It's not, and it's never going to be a AI first, you know, five X, 10 X growth company.”
Rory O'Driscoll May 7, 2026 ▶ 45:19 Anthropic's Raise & What It Means for Potential IPO? Mag7: Google & Amazon Up, Meta & Microsoft Down · 20VC with Harry Stebbings
Opinion
Rajaram: Monday.com has a much weaker defensibility score than Atlassian
“Monday probably has a score of one, I think. They have a workflow mode. I'm not sure if they have the other modes. So you're right. Monday, in theory, has a much weaker score, I guess, than Atlassian on this.”
Gokul Rajaram Mar 16, 2026 ▶ 13:29 Gokul Rajaram: How to Analyse for Durability and Defensibility in a World of AI · 20VC with Harry Stebbings
Opinion
Rajaram: Atlassian possesses at least three core software defensibility moats
“Atlassian has, you could argue they have proprietary data. Now they need to use that data to build products. They have unique proprietary data on all the code out there because it's being checked in. There's a lot of stuff they have, which they need to use for…”
Gokul Rajaram Mar 16, 2026 ▶ 12:52 Gokul Rajaram: How to Analyse for Durability and Defensibility in a World of AI · 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: 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
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
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
Prediction Not checkable as stated
Cannon-Brookes: AI vibe coding will lead to far more generalists at Atlassian
“If you ask me, in Atlassian, I will end up with far more generalists. People, I will end up with a wider organization, and people will do far more things, and their jobs will hopefully be more fulfilling because of it, right?”
Mike Cannon-Brookes Oct 13, 2025 ▶ 29:35 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
Disclosure
Mike Cannon-Brookes: Atlassian is currently launching a vibe coding environment
“I'm in Barcelona and we're launching one at the moment.”
Mike Cannon-Brookes Oct 13, 2025 ▶ 28:39 Atlassian CEO, Mike Cannon-Brookes on Why Everything is Overvalued & Are We in an AI Bubble · 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
O'Driscoll: Atlassian's M&A spree will not make it an AI leader
“Look, it's not going to make them, quote, an AI leader, but it, you know, they're doing the smart thing that existing corporations do, buying relatively new technology to, you know, to try.”
Rory O'Driscoll Sep 25, 2025 ▶ 1:23:46 The Impact of H1B Visas on Startups in the US & NVIDIA Invests $100BN Into OpenAI · 20VC with Harry Stebbings
Assertion Supported
Gonto: 80% to 85% of top PLG revenue comes from enterprise accounts
“If you look at all of the companies like Atlassians of the world, like the Twilios of the world, Outsido, or even Bursell, most of them, what ends up happening is that 80, 85% of the revenue comes from mid-market and enterprise, 15% come from SMBs, but that 15…”
Martin Gontovnikas (Gonto) Feb 14, 2024 ▶ 40:38 Martin Gontovnikas (Gonto): The Biggest Mistakes Startups Make When Scaling into Enterprises | E1115 · 20VC with Harry Stebbings
Disclosure
Farquhar: Atlassian Is Not Building Proprietary Large Language Models
“So we don't have to make the huge list and investments of you know, building our own large language model or building, you know, our own thing across So across, you know, data sets.”
Scott Farquhar Oct 9, 2023 ▶ 25:08 Scott Farquhar: Founding Atlassian; How We Scaled to a $50B Valuation; The 4 Jobs of a CEO | E1070 · 20VC with Harry Stebbings
Insight
Farquhar's framework for overcoming sunk cost fallacy in product decisions
“It ended up not being a hard decision because the way I looked at it was, you know, could I look my staff in the face and say that the next five years of their life was going to be the biggest impact to humanity working on this product?”
Scott Farquhar Oct 9, 2023 ▶ 33:48 Scott Farquhar: Founding Atlassian; How We Scaled to a $50B Valuation; The 4 Jobs of a CEO | E1070 · 20VC with Harry Stebbings
Assertion Not publicly verifiable
Farquhar: Benchmark declined splitting Atlassian's initial round with Accel
“And actually like we went back to Peter Fenton at Benchmark was, I think the runner up bidder. And we went back to Excel and said, Hey, look, all things considered, maybe we should get two VCs or, you know, in there, even though there was a huge difference in …”
Scott Farquhar Oct 9, 2023 ▶ 14:25 Scott Farquhar: Founding Atlassian; How We Scaled to a $50B Valuation; The 4 Jobs of a CEO | E1070 · 20VC with Harry Stebbings
Insight
Farquhar: Scaling shifts leadership mistakes from commission to omission
“When you're small as a company, or what I found when we were small as a company, the mistakes are mistakes of commission. Like, you do something stupid that didn't make sense, or you invested time in something that ultimately was a waste of time. I think when …”
Scott Farquhar Oct 9, 2023 ▶ 16:14 Scott Farquhar: Founding Atlassian; How We Scaled to a $50B Valuation; The 4 Jobs of a CEO | E1070 · 20VC with Harry Stebbings
Insight
Farquhar: Heavily funded startups outpace bootstrapped rivals in crowded markets
“I think it depends on what you're going after and the niche or niches Americans say that you're going after, because if there are thousands of other companies or dozens of other companies going after the same customer that you are, And they've raised 10 times,…”
Scott Farquhar Oct 9, 2023 ▶ 4:08 Scott Farquhar: Founding Atlassian; How We Scaled to a $50B Valuation; The 4 Jobs of a CEO | E1070 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Farquhar: Connectivity gains from in-person work events decay over 4-5 months
“How long does it take to return to baseline? It's four to five months actually before that returns to the baseline.”
Scott Farquhar Oct 9, 2023 ▶ 30:08 Scott Farquhar: Founding Atlassian; How We Scaled to a $50B Valuation; The 4 Jobs of a CEO | E1070 · 20VC with Harry Stebbings
Assertion Supported
Simons: Atlassian never followed the 'triple, triple, double, double' growth model
“And, you know, Atlassian, you know, was never a triple, triple, double, double, double company. It was this kind of methodical, reasonable grower.”
Jay Simons Jun 10, 2021 ▶ 31:05 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
Opinion
Fernandez: Advice that multitasking is ineffective ignores working parents and executives
“The one that causes me to roll my eyes the most profoundly is that multitasking is ineffective, clearly written by someone who is not a mother of three kids, a CEO of a company, and sitting on the board of Atlassian.”
Heather Fernandez Aug 24, 2018 ▶ 26:01 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
Insight
Reyes: Widely disliked enterprise software is durable because of underlying systems of record
“I think that the biggest thing is when people say, I hate that software and everyone buys it, that's probably a pretty good business, because they're not buying the software, they're buying what's underneath of it, and that to me is actually much more durable …”
Eno Reyes Aug 29, 2026 ▶ 1:20:39 Should American Enterprises Work With Open-Source Chinese Models? | Only 10% of Neo-labs survive
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
Disclosure
Cannon-Brookes: Accel's $60M Atlassian investment in 2010 was 100% secondary
“When the Excel guys invested in Atlassian, right? It was all secondary. They put sixty million bucks in 2010. And they bid highest of the five VCs.”
Mike Cannon-Brookes Feb 12, 2026 ▶ 33:16 Anthropic's Super Bowl Ad: Who Won & Lost? | Sierra Hits $150M ARR: Is Customer Support Too Crowded? · 20VC with Harry Stebbings
Disclosure
Cannon-Brookes: Anthropic is one of Atlassian's largest AI models
“We use Anthropic a lot. It's one of our biggest models. We use, you know, multiple models which I think is what most good SaaS vendors are doing within their customers' choices, right? Like we use a lot of Gemini, a lot of Anthropic. We have a whole bunch of L…”
Mike Cannon-Brookes Feb 12, 2026 ▶ 2:42 Anthropic's Super Bowl Ad: Who Won & Lost? | Sierra Hits $150M ARR: Is Customer Support Too Crowded? · 20VC with Harry Stebbings
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