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Prediction Open · timeframe Jul 2027
SpaceX, Anthropic, and OpenAI IPOs will exceed all past tech IPOs combined
“We're going to see three trillion dollar plus IPOs over the coming months. It's never happened before. The value of SpaceX plus Anthropic plus OpenAI will be more than all the other tech IPOs combined ever.”
Jason Lemkin Jul 8, 2026 ▶ 45:45 Agents Didn't Kill Sales. They Just Exposed It with SaaStrAI CEO and Founder Jason Lemkin
Prediction Not checkable as stated
Lemkin: Four Upcoming Tech Mega-IPOs Will Eclipse All IPOs Since 2000
“SpaceX, Anthropic, OpenAI, we'll add in Databricks, we'll have Arsan, one of the co-founders here in about half an hour after this. That's going to create more market value, more value, and more wealth than every other IPO since 2000.”
Jason Lemkin Jun 11, 2026 ▶ 13:41 $4 Trillion in IPOs, $100B in M&A, and Why B2B Spend is Booming
Prediction Not checkable as stated
Benioff: Microsoft's Partnership With OpenAI Will Turn Into Direct Competition
“Microsoft is a company that wants to own it all, control it all. If they see a hot company or a hot startup, they ask themselves, hey, why is that not in our world? And in the case of they, usually they like To either try to feign an acquisition and then based…”
Marc Benioff May 2, 2025 ▶ 10:14 AI, M&A, and the Future of SaaS: Lessons from Marc Benioff, Salesforce CEO, Co-Founder and Chair
Prediction Not checkable as stated
Ripabelli: 99.9% of OpenAI and Anthropic users will not stay on DeepSeek
“But I think in two months, I think, 99.9% of the people who are using Anthropic and OpenAI today is going to go back to using their products, not DeepSeek's model.”
Victor Riparbelli Jan 31, 2025 ▶ 13:54 The Future of AI in B2B SaaS: Insights from Synthesia and Theory Ventures. Hosted by Jason Lemkin
Prediction Open · timeframe Dec 2032
O'Driscoll: OpenAI and Anthropic Revenues Won't Match AI CapEx Until 2031-2032
“The stunning thing is it takes until 2031 or 2032 before The revenue from those two companies surpasses the total capex.”
Rory O'Driscoll Jul 15, 2026 ▶ 6:56 Software Isn't Dead. It's Gotten Harder with Scale Venture Partners' Rory O'Driscoll
Prediction Not checkable as stated
O'Driscoll: Foundation model makers will probably continue capturing the delta value
“The truth is they are the apex predator of this distribution. They are the guys who have taken the value, the delta value, and probably will continue to do so under those forecasts.”
Rory O'Driscoll Jul 15, 2026 ▶ 11:26 Software Isn't Dead. It's Gotten Harder with Scale Venture Partners' Rory O'Driscoll
Prediction Not checkable as stated
O'Driscoll: OpenAI, Anthropic, and Gemini will capture oligopolistic foundation model profits.
“There's no doubt that a two-way or a three-way dominance of the foundation model category will be between OpenAI and Tropic and Gemini with maybe some other players. They will dominate that. They probably will have, you know, oligopolistic profits.”
Rory O'Driscoll Jul 15, 2026 ▶ 27:51 Software Isn't Dead. It's Gotten Harder with Scale Venture Partners' Rory O'Driscoll
Prediction Open · timeframe Jan 2031
Lemkin: Anthropic and OpenAI Will Reach Trillion-Dollar Valuations
“Anthropic isn't topping out at a billion. OpenAI isn't topping at a billion. They're topping at a trillion.”
Jason Lemkin Jan 2, 2026 ▶ 14:04 AI + B2B in 2026: Find the Tailwinds or Get Left Behind | Jason Lemkin
Assertion Not checkable as stated
Maggie Hott: OpenAI has a 100% win rate on enterprise pilots
“We have a hundred percent win rate on pilots”
Maggie Hott Dec 24, 2025 ▶ 27:29 Why OpenAI Doesn't Pay Sales Commission (And Why It Works) with OpenAI GTM Leader Maggie Hott
Insight
Lemkin: VCs now target trillion-dollar outcomes instead of billion-dollar exits
“VCs are now looking for trillion dollar outcomes. People have decided that every couple of years, there'll be another open AI. Not every week. There'll be a trillion dollar company.”
Jason Lemkin Aug 27, 2025 ▶ 10:18 What Happens When AI Kills Your SaaS Growth? Live Q&A with SaaStr CEO and Founder Jason Lemkin
Opinion
Hott: OpenAI Launched the Fastest-Growing Enterprise Application in History
“OpenAI already had the fastest growing consumer application in history, and then this brand new team that we built, we believe launched the fastest growing enterprise application in history.”
Maggie Hott Aug 6, 2025 ▶ 28:55 How to Build Top-Performing Sales Orgs with OpenAI's GTM Leader Maggie Hott
Opinion
Ripabelli: Enterprise AI spending is driven by fear, not clear buyer need
“There's this weird thing in AI right now where it's very fear driven, and people are very willing to part ways with their money, both on consumer side, but also businesses to try out new things, right? Because everyone is scared that their business is going to…”
Victor Riparbelli Jan 31, 2025 ▶ 30:26 The Future of AI in B2B SaaS: Insights from Synthesia and Theory Ventures. Hosted by Jason Lemkin
Assertion Not checkable as stated
Grill: Many Enterprises Buy ChatGPT Enterprise Without Defined Use Cases
“There's a lot of companies right now that, and this is a luxury to be in this position, but for something like ChatGPT Enterprise, they are purchasing without a defined use case in mind”
Dominic Grill Jun 28, 2024 ▶ 18:06 Mastering SaaS Sales Hiring, Customer Retention, and Growth with OpenAI, Retool, and 20VC
Insight
Tamir: Direct OpenAI or Anthropic APIs outperform cloud intermediary platforms
“Using a first party solution with say OpenAI or with Anthropic is going to have different performance, different latency than if you do it via an intermediary, like a cloud. So you maybe get some simplicity by not having to onboard different vendors and differ…”
Mike Tamir Apr 26, 2024 ▶ 14:53 How Shopify Implements AI Across Sales and Product with the Head of AI at Shopify
Opinion
O'Driscoll: OpenAI and Anthropic Prove Software Is Not Dead
“What they don't mean is software dead because OpenAI and Entropic are software, and they are most definitely not dead.”
Rory O'Driscoll Jul 15, 2026 ▶ 14:13 Software Isn't Dead. It's Gotten Harder with Scale Venture Partners' Rory O'Driscoll
Insight
Anderson: Wrapping third-party AI APIs will not cut it by 2026
“If you are going to build an AI application today, you can't simply say, hey, we've got all these APIs. OpenAI has APIs. Done. We'll connect them. We've got an AI application. That is not going to cut it in 2026. To be AI native, actually have to change the ar…”
Ryan Anderson Jan 14, 2026 ▶ 10:16 10 Things To Do Right Now to Become AI Native with Filevine's CEO & Founder
Insight
Maggie Hott: Never do software pilots without direct executive training participation
“You should not be doing a pilot unless you have that executive buy-in and sign off. In our case, we make sure that executives are sitting through a training Of ChatGPT, otherwise we're not doing a pilot. They have to be involved in it.”
Maggie Hott Dec 24, 2025 ▶ 28:07 Why OpenAI Doesn't Pay Sales Commission (And Why It Works) with OpenAI GTM Leader Maggie Hott
Disclosure
Hott: Working in AI Is a Privilege Leaving No Room for Mediocrity
“I have no tolerance for mediocrity anymore. When you are stared in your life with something like this, what is, which is probably one of the worst things I will ever go through, and then I was able to beat it created this intolerance for people who do not give…”
Maggie Hott Dec 24, 2025 ▶ 4:59 Why OpenAI Doesn't Pay Sales Commission (And Why It Works) with OpenAI GTM Leader Maggie Hott
Disclosure
OpenAI's GTM leader works seven days a week and every night
“Most days I will work seven days a week, and I will work bizarre hours, and if it's, you know, Tuesday night watching TV with my husband, unfortunately, that just doesn't happen. Like, we, I leave the office by four 30 every single day, but you better believe …”
Maggie Hott Dec 24, 2025 ▶ 17:13 Why OpenAI Doesn't Pay Sales Commission (And Why It Works) with OpenAI GTM Leader Maggie Hott
Assertion Not checkable as stated
ChatGPT receives hundreds of millions of healthcare queries every week
“When we look at the queries that come into ChatGPT, we get hundreds of millions of healthcare queries every single week.”
Maggie Hott Dec 24, 2025 ▶ 33:54 Why OpenAI Doesn't Pay Sales Commission (And Why It Works) with OpenAI GTM Leader Maggie Hott
Assertion Supported
OpenAI deploys HIPAA-regulated AI technology across UCSF
“We now have in America, it's HIPAA, I'm not sure if it's the same out here, but a HIPAA regulated version of our technology, and we are already selling this to physicians, to doctors, UCSF, it's a top leading hospital in America. Every single person there has …”
Maggie Hott Dec 24, 2025 ▶ 34:21 Why OpenAI Doesn't Pay Sales Commission (And Why It Works) with OpenAI GTM Leader Maggie Hott
Assertion Partly supported
Lemkin: Datadog Manages All DevOps for OpenAI and Accelerated Growth
“Datadog has accelerated. Because it sells to all those leaders because it does all DevOps for open AI.”
Jason Lemkin Oct 5, 2025 ▶ 4:20 Is The Classic GTM Playbook Really Dead? with SaaStr CEO and Founder Jason Lemkin
Opinion
Lemkin: Top AI Companies Rely on Traditional SaaS GTM Leaders
“If you look at who is running go-to-market at some of the hottest AI companies from open AI to anthropic on down, you'll see folks that spoke at Saster in the past few years. You will see the exact same people essentially running the same playbooks they ran be…”
Jason Lemkin Oct 5, 2025 ▶ 3:09 Is The Classic GTM Playbook Really Dead? with SaaStr CEO and Founder Jason Lemkin
Insight
Lemkin: Traditional SaaS playbooks still work with intense PMF
“I actually think the traditional playbook act, not with saying what Kyle and I talked about this morning. If you have intense product market fit, it works fine. Open AI is doing field events. Open AI is doing webinars. Open AI has as swag open. I mean, but ope…”
Jason Lemkin Aug 27, 2025 ▶ 12:25 What Happens When AI Kills Your SaaS Growth? Live Q&A with SaaStr CEO and Founder Jason Lemkin
Assertion Not checkable as stated
Hott: OpenAI Long Customer Pilots Increased Deal Sizes by 5x
“And we found that by doing long intensive pilots, our deal sizes went up by about five X, which is pretty incredible.”
Maggie Hott Aug 6, 2025 ▶ 35:21 How to Build Top-Performing Sales Orgs with OpenAI's GTM Leader Maggie Hott
Disclosure
Harmon: OpenAI frequently lowers prices with upgraded models without raising them
“OpenAI has certainly done that many more times than twice a year. We typically launch a model and then weeks or months later launch another version of it that's even better and lower the price and then lower the price again. I think that really speaks to the s…”
Allison Harmon Dec 3, 2024 ▶ 23:47 How to Leverage Pricing and Packaging to Drive Revenue with Miro, Loom, OpenAI, and Splunk
Disclosure
Riparbelli: Synthesia concedes general AI video to focus on talking avatars
“For us, we think, well, we're not, not going to be the best in the world at general AI video, like Sora style from OpenAI. What we think we can be the best in the world at are people presenting to the camera, and that is a huge category. And so if we focus all…”
Victor Riparbelli Sep 18, 2024 ▶ 19:44 From 0-50,000 Customers: How to Build a GenAI Company for the Enterprise with Synthesia's CEO
Assertion Not checkable as stated
Grill: OpenAI's enterprise projects with Klarna and Spotify took nine months
“When we talk about some of these companies like Klarna or Spotify or Morgan Stanley that have really done something transformational, I think we all have to keep in mind, we started those projects probably nine months ago, and it takes time and iteration in or…”
Dominic Grill Jun 28, 2024 ▶ 9:29 Mastering SaaS Sales Hiring, Customer Retention, and Growth with OpenAI, Retool, and 20VC
Insight
Grill: Enterprises validate on frontier models before optimizing costs with smaller models
“You start and validate with the most reasonable And the most intelligent, the frontier model, in our case, GPT-FORO. But once you've validated that the use case is possible, then you try and cost optimize and look for if you can still accomplish that with the …”
Dominic Grill Jun 28, 2024 ▶ 16:31 Mastering SaaS Sales Hiring, Customer Retention, and Growth with OpenAI, Retool, and 20VC
Disclosure
Grill: OpenAI turns down direct account team support for smaller enterprise customers
“We have to. Yeah, absolutely. It doesn't mean that we don't turn them down from a technology perspective, but it means that we can only work with them directly with an account team at a certain level of scale.”
Dominic Grill Jun 28, 2024 ▶ 6:01 Mastering SaaS Sales Hiring, Customer Retention, and Growth with OpenAI, Retool, and 20VC
Insight
Grill: Companies rush into sales verticalization too early without product alignment
“My hot takes, I think companies rush to verticalization a little too early. And I do think you have to really understand what your overall value proposition and get your core sales motion going before you just rush to verticalization. Because the challenge tha…”
Dominic Grill Jun 28, 2024 ▶ 29:43 Mastering SaaS Sales Hiring, Customer Retention, and Growth with OpenAI, Retool, and 20VC
Insight
Grill: Enterprise AI innovation comes from business units, not ML teams
“One is that a lot of large enterprises think that the innovation is going to start with their machine learning team or their data science team. And what we're seeing a lot of innovation happen is actually at the line of business level, the people that are clos…”
Dominic Grill Jun 28, 2024 ▶ 8:41 Mastering SaaS Sales Hiring, Customer Retention, and Growth with OpenAI, Retool, and 20VC
Assertion Supported
Lemkin: OpenAI conducts annual tender offers paying engineers millions
“OpenAI for engineers does tender offers every year, where you make millions of dollars a year from working in Open.”
Jason Lemkin Feb 2, 2024 ▶ 11:10 2025 State of SaaS: Trends and Predictions with SaaStr CEO and Founder, Jason Lemkin
Assertion Supported
OpenAI finished training GPT-4 in August 2022, holding it six months for safety
“We actually finished training GPT-IV in August last year, but we waited a little while before releasing it. When we first tried it out, we were all quite flabbergasted by how powerful it was, and we decided to sit on it almost six months to make sure that it w…”
OpenAI's Head of Sales Oct 20, 2023 ▶ 2:34 The Chat GPT Growth Story: How AI is Changing the Way We Work with OpenAI's Head of Sales
Insight
O'Driscoll: Vertical AI apps combining sensors with models are highly defensible
“If you're doing kind of a combination of software and sensors, you've got something that's obviously manifestly different. You know, you've got maybe visual sensors. You've got touch sensors. You got something out there that says, oh, but I ain't going to star…”
Rory O'Driscoll Jul 15, 2026 ▶ 19:28 Software Isn't Dead. It's Gotten Harder with Scale Venture Partners' Rory O'Driscoll
Insight
Lemkin: Goal-seeking AI agents cut corners by doing minimal work
“Agents are goal-seeking, right? Most of them under the hood are clawed. It'll be more, we use Gemini ourselves too. We'll use more open ad. Most of them are clawed, but it doesn't matter. They're goal-seeking. And that still creates a certain laziness, which i…”
Jason Lemkin Apr 22, 2026 ▶ 3:53 Managing 20+ AI Agents: Lazy Agents, Our $500K AI Bill, Stealth Churn & the Death of 60% Solutions
Disclosure
LaRoute: I have stealth churned off ChatGPT since December
“I hate to say that I've stealth churned off ChatGPT, but I literally just looked. I haven't used it since December.”
Amelia LeRutte Apr 22, 2026 ▶ 29:37 Managing 20+ AI Agents: Lazy Agents, Our $500K AI Bill, Stealth Churn & the Death of 60% Solutions
Assertion Partly supported
OpenAI, Slack, Figma, and Airtable all started without sales commissions
“So with OpenAI, with Slack, many other, Airtable, Figma, New Relic, there's tons of companies out there that all started with this model of full salary, and it's a, you know, a normal living salary like you would give to any other product manager, marketer, en…”
Maggie Hott Dec 24, 2025 ▶ 11:08 Why OpenAI Doesn't Pay Sales Commission (And Why It Works) with OpenAI GTM Leader Maggie Hott
Insight
Hott: Rushing Back to Work After Cancer Surgery Compromised Health Pointlessly
“I rushed back to work a month after surgery. Even Stanford was like, no one's ever gone back after a month, but we had a new chief customer officer at OpenAI, and I wanted him to know me. He'd already been there for a month, and I just needed to make sure he k…”
Maggie Hott Dec 24, 2025 ▶ 5:56 Why OpenAI Doesn't Pay Sales Commission (And Why It Works) with OpenAI GTM Leader Maggie Hott
Assertion Supported
Lemkin: OpenAI Relies on Customer Pilots to Close Enterprise Deals
“OpenAI does pilots now. OpenAI, the hottest company on planet earth. Are you another video to close big deals? They have to do pilots.”
Jason Lemkin Oct 5, 2025 ▶ 6:40 Is The Classic GTM Playbook Really Dead? with SaaStr CEO and Founder Jason Lemkin
Opinion
OpenAI Reinforcement Fine-Tuning Makes Domain-Specific Models Viable for Vertical Apps
“In the last few months, OpenAI shipped reinforcement fine tuning, which is kind of a new way of fine tuning that they offer. And it's actually quite good. And so it actually is starting to seem again being able at least to not pre-train, but fine tune data on …”
Jacob Effron Aug 13, 2025 ▶ 10:32 Redpoint Ventures Playbook: How Top VCs Are Really Investing in AI with Jacob Effron
Assertion Not checkable as stated
Hott: OpenAI's GTM team scaled from 10 to 500 people in two years
“In two years, we have gone from 10 to 500 people, and we are going to keep on going.”
Maggie Hott Aug 6, 2025 ▶ 20:34 How to Build Top-Performing Sales Orgs with OpenAI's GTM Leader Maggie Hott
Disclosure
Hott: OpenAI Merged API and ChatGPT Enterprise Into 500-Person Team
“So, earlier this year, we basically collapsed both of these orgs. We took 500 people, most people who had only been to the company for a few months, and we brought them into one single unified go-to-market org.”
Maggie Hott Aug 6, 2025 ▶ 29:16 How to Build Top-Performing Sales Orgs with OpenAI's GTM Leader Maggie Hott
Assertion Not checkable as stated
Tunguz: AI for sales lead analysis works accurately 80% to 85% of the time
“But if I use ChatGPT or OpenAI or a call recording software to determine what's going on with a lead or customer prospect, state-of-the-art says it'll work somewhere between 80 to 85% of the time.”
Tomasz Tunguz Oct 24, 2024 ▶ 1:55 The State of SaaS Go-to-Market l Theory Ventures General Partner Tomasz Tunguz #saas #b2bsaas
Insight
Grill: Very few companies have a serious strategy for deploying AI
“It's been shown actually multiple times that lots of companies have interest in AI. But very few companies actually have a serious strategy in place around how to go in and deploy and make use of the technology.”
Dominic Grill Jun 28, 2024 ▶ 6:55 Mastering SaaS Sales Hiring, Customer Retention, and Growth with OpenAI, Retool, and 20VC
Disclosure
Hott: Customization is the top priority for ChatGPT Enterprise
“We've shared pretty broadly that the single biggest thing that we are working on right now is this idea of customization.”
Maggie Hott Dec 8, 2023 ▶ 10:27 The Where, When, and How of AI with Theory Ventures, Open AI, MotherDuck and Lamini
Disclosure
Hott: OpenAI is building a self-serve ChatGPT version for SMBs
“The other thing that we are also building right now, which is really exciting is a business version. So more of a self-serve version for SMBs.”
Maggie Hott Dec 8, 2023 ▶ 10:58 The Where, When, and How of AI with Theory Ventures, Open AI, MotherDuck and Lamini
Assertion Not checkable as stated
Rosenthal: OpenAI's early sales model was oversold, unscalable consulting
“On my first week, I walked in the door and the first meeting I came into, they said, we have oversold our license model and we need you to help us undo it. When I dug further into this, I understood we were actually selling services. So we were saying, hey, bu…”
OpenAI's Head of Sales Oct 20, 2023 ▶ 4:45 The Chat GPT Growth Story: How AI is Changing the Way We Work with OpenAI's Head of Sales
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