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Insight
Lemkin: Highest-usage SaaS customers often have the strongest incentive to leave
“And the folks with the highest usage may actually have the most incentive to leave. It's not a clear correlation to success, right?”
Jason Lemkin Aug 5, 2026 ▶ 26:56 The Agents #12 - Our AI Agent Rewrote Our App Without Telling Us
Insight
Lemkin: Customers Prefer High-Performing AI to Mediocre Human Account Managers
“Customers will prefer, prefer a great eye to a mediocre human. They'll prefer a great eye that solves their problem today, that knows the answer, to someone that has to get an engineer and an appointment to you next week, that doesn't know, that says I'm just …”
Jason Lemkin Jun 11, 2026 ▶ 25:55 $4 Trillion in IPOs, $100B in M&A, and Why B2B Spend is Booming
Insight
Adams: Companies must part ways with a third of staff for AI
“Like a third of your company, you need to part ways with them. They're not fit for this new world. They don't want to build the same way you want to build. They don't like fast, crazy fast pace. They don't like chaos.”
Paul Adams Jan 28, 2026 ▶ 12:39 Why Most SaaS Companies Will Fail at AI (And How to Avoid It) with Intercom's CPO
Insight
Anderson: SaaS incumbents should monitor API traffic and copy successful AI features
“The AI traffic is going to reveal something to you. You will review, reveal promising areas for new development. You will all of a sudden see very early on. Which products are gaining traction, and you should 100% copy those products. You should copy those pro…”
Ryan Anderson Jan 14, 2026 ▶ 21:29 10 Things To Do Right Now to Become AI Native with Filevine's CEO & Founder
Insight
Lemkin: A B-Plus AI Handles Sales Leads Better Than Humans
“It's better to give a precious lead to an ad to a B plus AI than to give it to someone in sales. That's going to quit, not show up or screw up the deal.”
Jason Lemkin Oct 5, 2025 ▶ 45:20 Is The Classic GTM Playbook Really Dead? with SaaStr CEO and Founder Jason Lemkin
Insight
Nithrakashyap: Ignore startup advice to say no; say yes to everything
“I know there's this advice that say no to a 95%. I don't believe in that. I think you have to say yes to yes to everything, right? Because if you lose, if you miss a large fortune, 500 customer, it may be a hundred K deal down the road. That's a 20, 30 X lifet…”
Arvind Nithrakashyap Jun 25, 2025 ▶ 8:24 AI and Cybersecurity: Scaling Rubrik to a Billion Dollar Enterprise with Rubrik's Co-Founder and CTO
Insight
Lemkin: RTO mandates are about supervising mid performers, not collaboration
“It doesn't, you don't need to return to office for high performers. The best people will get it done. They'll get it done from Antarctica or they'll get it done in the office, but the mid performers just don't work from home, right? They barely work. And so th…”
Jason Lemkin Feb 19, 2025 ▶ 21:49 The 2025 SaaS Vibe Check: What Founders Need to Know Right Now with SaaStr Founder Jason Lemkin
Insight
Mooney: In vertical SaaS, product, sales, and support must replace customer success
“So the like simple framework here is that the product owns success. So this means that It should be so aligned and so good with your verticals needs that it doesn't need translation and it doesn't need somebody to come back in and say, Hey, we noticed you're n…”
Marchelle Mooney Jan 14, 2025 ▶ 30:25 10 Ways Sales is Different in Vertical SaaS with Mangomint's VP of Sales
Insight
Lemkin: Cutting sales headcount in half increases revenue at $50M ARR
“The tactical answer for more kumbaya people is probably cut half your sales team. This always works. Concentrate your leads in tougher times. It may not work at Matt. Maybe it doesn't work at zoom info scale, but even at fifty million, it's going to work.”
Jason Lemkin Oct 18, 2024 ▶ 35:52 The Future of AI and Sales in SaaS with Henry Schuck, CEO of ZoomInfo and SaaStr CEO Jason Lemkin
Insight
Lemkin: SaaS companies must compete in categories where they lose most deals
“You gotta play in categories where you lose most deals to win. This is a weird thing. You gotta play in categories where you lose most deals.”
Jason Lemkin Oct 18, 2024 ▶ 39:07 The Future of AI and Sales in SaaS with Henry Schuck, CEO of ZoomInfo and SaaStr CEO Jason Lemkin
Insight
Lemkin: SaaS growth slowdowns stem from lost product-market fit, not macro
“If growth has slowed, it is not a downturn or macro. It's a little bit of it. It is that you have fallen out of product market fit. If two years ago you were growing a hundred percent and today you're growing. It is not just the market. It is that you do not h…”
Jason Lemkin Oct 15, 2024 ▶ 41:35 The Era of HyperFunctional SaaS is Here l SaaStr CEO and Founder Jason Lemkin
Insight
Stebbings: Multi-stage VC employees must chase hype deals to get promoted
“If you are a strategic person in a multi-stage fund, getting into one of these hot deals is what's going to get you the promotion. Doing the slightly off the beaten track, but amazing company that might take three or four years to get to product market fit, or…”
Harry Stebbings Aug 30, 2024 ▶ 23:52 Navigating Fundraising and the VC Landscape Today with 20VC and Visionaries Club
Insight
Lemkin: Failed hires are always the founder's fault, never the employee's
“It's always your fault when someone doesn't work out... It's you didn't do the work. You didn't figure out if they were the right fit. They never know. You can never know enough about a company before you join. It's impossible.”
Jason Lemkin Mar 20, 2024 ▶ 41:31 Advice Every SaaS Founder Needs to Know to Scale to $100m with Sam Blond and Jason Lemkin
Insight
Cabane: Monetization must precede open-source acquisition motions
“Monetization comes first, open source for acquisition comes second. Other way around is, like, super hard, my opinion, huh?”
Guillaume Cabane Feb 7, 2024 ▶ 26:46 Mastering High-Volume, Low-CAC Marketing: Strategies from Gorgias, Vercel, and Hypergrowth
Insight
Lemkin: SaaS sales and marketing has not gotten more efficient since 2005
“So far, since I've been involved in SAS since 2005, we have not gotten any more efficient. In sales and marketing, we've gotten more efficient at other things.”
Jason Lemkin Dec 29, 2023 ▶ 19:10 Why the Future of Customer Success, Sales & Marketing Has Changed with SaaStr CEO Jason Lemkin
Insight
Lemkin: SaaS products that cannot self-renew 80% of deals are failing
“I think if you have humans in a renewal, you're you have failed your customers. You have failed your customers. If you need sales or success or account, it doesn't mean that the margin, you don't need help. I'm not saying you don't need to parachute in on 10% …”
Jason Lemkin Dec 29, 2023 ▶ 25:40 Why the Future of Customer Success, Sales & Marketing Has Changed with SaaStr CEO Jason Lemkin
Insight
Roberge: Top AI talent beats mediocre teams with trillions of data records
“So if you had to choose between having an A plus AI tech talent team with millions of records of data, and you were going against a mediocre AI tech talent team with trillions of data that the startup wins. And that starts to make sense with the diminishing re…”
Mark Roberge Nov 17, 2023 ▶ 20:44 Who Will Win the Go-To-Market AI Race? with Stage 2 Capital Co-founder Mark Roberge
Insight
Seibel: Hiring a designer for a startup pitch deck is a mistake
“If you need a designer to build a slide deck, you're doing it wrong. And here's an even deeper, more important point. Your designer has no idea what the most interesting and important points of your pitch are. So if you hand them your pitch to design, they wil…”
Michael Seibel Oct 5, 2023 ▶ 25:13 How To Perfectly Pitch Your Seed Stage Startup With Y Combinator's Michael Seibel
Insight
Lemkin: SaaS founders should avoid non-performance layoffs given recurring revenue visibility
“They're tough on all of us, and I really think as founders, we should do everything humanly possible to have no non-performance layoffs. I mean, we have recurring revenue. You should be able to predict the next quarter or two. You should be a little embarrasse…”
Jason Lemkin Oct 3, 2023 ▶ 12:36 2024 SaaS Landscape: Why 2024 Could be Pretty Darn Good for SaaS IPOs with SaaStr CEO Jason Lemkin
Insight
Lemkin: How SaaS companies unethically brute-force high Net Retention Rates
“You can brute force high NRR with longer term deals. You can brute force NRR if you threaten customers when they leave with an inability to get their data. You can brute force NRR by having out of bound price increases, 30 or 40% a year.”
Jason Lemkin Aug 3, 2023 ▶ 27:28 The Most Important SaaS Metrics with Monday.com Co-Founders and SaaStr Founder Jason Lemkin
Insight
Parker Conrad: Silicon Valley's startup focus orthodoxy is wrong and limiting
“This conventional wisdom is wrong or at least extremely limiting, and there exists a set of companies that could be built that are often not built that break this rule.”
Parker Conrad Jun 27, 2023 ▶ 2:06 Rippling CEO Parker Conrad's Theory of the Compound Startup: Disrupting How We Think About Software
Insight
Lemkin: Startups Slowing to Zero Growth Lost Product-Market Fit
“With a few exceptions, I don't have any empathy for startups that had decent growth during 2021 and have slowed to zero. Ok, I don't have any empathy. You really have no customers? Really none? No. What it really means is your product wasn't valuable enough. I…”
Jason Lemkin Jun 16, 2023 ▶ 18:22 Why The Era of Efficient Growth is Now: The State of the Market with SaaStr CEO Jason Lemkin
Insight
Delatorre: Startups cannot scale from $20M to $100M on PLG alone
“But you don't get from 20 to a hundred on PLG because, you know, to get from 20 to a hundred, you're probably doing bigger deals, and you're doing bigger deals at bigger companies, and so PLG makes for a great meeting, and you know, I think in a hundred, if yo…”
Carlos Delatorre Jan 27, 2022 ▶ 17:21 Scaling Your Startup 10x From $20M to $200M with Sapphire, Lightspeed, TripActions, and 6Sense
Insight
Barrett: Hiring outside VC executives caps internal talent and drives them away
“How many of those same people just brought in some kind of outside executive from their VCs? Yeah, you just fucked your entire company. Because by doing that, you just indicated to every one of your employees, you cannot grow here. That we value skills that yo…”
David Barrett Nov 17, 2021 ▶ 29:45 The Highs and Lows of Fundraising from Founders That Have Raised $1B w/ Calendly, Coda, LaunchDarkly
Insight
Hoffman: 10x hires almost certainly have glaring faults
“If you want to hire a 10 Xer, that person will almost certainly have glaring faults. Anyone that you could hire without glaring faults will be at best good. They will not be great.”
Auren Hoffman Apr 18, 2021 ▶ 3:18 How to Build a Unicorn in 8 Simple Charts with SafeGraph
Insight
Hoffman: Leaders should delegate functions they are good at, not weak at
“Instead, delegate things that you're good at. This sounds really strange, so let me explain. The things that are the easiest to delegate are the things that you're already good at. You know how to do these things really well. You might already be an expert in …”
Auren Hoffman Apr 18, 2021 ▶ 4:10 How to Build a Unicorn in 8 Simple Charts with SafeGraph
Insight
Hoffman: Most VC rejection reasons, especially TAM concerns, are lies
“The reason that most VCs give you a no is lies, and especially the reason of total addressable market in your TAM.”
Auren Hoffman Apr 18, 2021 ▶ 17:04 How to Build a Unicorn in 8 Simple Charts with SafeGraph
Insight
Lawrence: Hire a VP of Sales at $8M to $10M ARR
“Like, I have an opinion. It should be between eight to 10 in ARR. If you want a really solid VP of sales, they're gonna want to come in. They don't want it to be too scrappy, and they don't want it to be too far ahead”
Jennifer Lawrence Sep 19, 2019 ▶ 31:07 How to Hire a Great VP of Sales with SaaStr + Duo Security
Insight
An 'A' investor provides capital, signs paperwork, and stays quiet
“An A investor gives you money, signs paperwork when you want them to, and shuts the fuck up. That's an A. There's a lot of room below an A. There's not a lot of room above.”
Michael Seibel May 8, 2019 ▶ 8:40 A Decade of Learnings from Y Combinator's CEO Michael Seibel
Insight
Seka: White men hold the most impactful voices in diversity advocacy
“If you are a white person, and my god, if you are a white man, which I love white men, I'm married to one, I'm made to, I'm down with it, right? I like them, but you have the most important voice in this, because no one expects you to say anything.”
Leila Seka Apr 29, 2019 ▶ 11:54 How we did it: Gender Equality, Equal Pay, and Racial Equality with Salesforce
Insight
Western: Founders amass more wealth through frequent, smaller startup exits
“We think that most founders can actually use the overfocus on growth to their advantage, like a judo artist, either by more often choosing the lifestyle option, or by having a more sober approach to their relationship with their companies and with VCs, by actu…”
Alex Western Jan 29, 2019 ▶ 18:20 Is Growth Bad for Startups?
Insight
Cohen: Servant leadership leads founders to do scut work and burn out
“This crappy word, servant leadership, it leads to stuff like this. This is the scut work that needs to be done, and I can do it, so I'll do it so the team doesn't need, doesn't have to do it. That sounds altruistic, and what it does is burn you out because you…”
Jason Cohen Jan 8, 2019 ▶ 25:04 From Burn-Out to $100M in ARR with Jason Cohen, Founder of WP Engine
Insight
Lemkin: Expanding to NYC instead of SF is European SaaS's biggest mistake
“Unless your customers are in New York, unless you're doing financial services or some parts of ad tech or otherwise, going to New York is the worst idea. you get none of the, almost none of the benefits of being in the Bay Area. You don't get the customers he…”
Jason Lemkin Mar 17, 2018 ▶ 1:55 SaaStrPRO AMA with Jason Lemkin
Insight
Lemkin: Abandoning free trials leads to broken onboarding and mediocre software
“Once you give up free trials, you will never go back, and you will be able to have terrible onboarding, and you will be able to have all this friction behind the scenes, and you will be able to have many broken processes and things, and you will never build gr…”
Jason Lemkin Mar 17, 2018 ▶ 32:12 SaaStrPRO AMA with Jason Lemkin
Insight
Barrett: VCs make money deploying capital, not on exits
“But the VC business model is they get paid when they invest. And so it actually, they don't really make money on the exit. Like, there's the carry, they would say, at the very end.”
David Barrett Jan 8, 2018 ▶ 13:41 Good Intentions, Bad Advice: How to Keep Your Board Aligned with Your Vision
Insight
Barrett: Hiring outside executives tells top internal talent to leave
“The second that you hire in, you know, sort of that, that, that pro who comes in above everyone else, you've just told everyone else in your company, fuck you. There's no way you can ever grow in this company. Because we have just hired someone above you whose…”
David Barrett Jan 8, 2018 ▶ 36:27 Good Intentions, Bad Advice: How to Keep Your Board Aligned with Your Vision
Insight
Reina: LLMs struggle in sales because they only produce within-distribution results
“I do still believe that, like, AI agents are not that good today actually at doing something that is very relationship driven. But they're getting much better at it, right? So, like, the problem is when you look at LLMs, they look at the distribution site, and…”
Carles Reina Sep 9, 2026 ▶ 33:36 CRO Confidential: 0 to $600M in Under 4 Years. The ElevenLabs GTM Playbook with Carles Reina
Insight
Lemkin: Raising API prices to offset lost seats will accelerate CRM churn
“I think it is a self-inflicted wound for a lot of systems of record and SaaS centers as they jack up the prices because seats are going down and agents are going up and they jack up the price for access. It's incense us finally to put more and more of our data…”
Jason Lemkin Aug 28, 2026 ▶ 12:27 Who Owns Your Data Now? Agents vs. Systems of Record on The Agents #013
Insight
Lemkin: Software vendors will lose if AI cannot autonomously execute APIs
“You're going to lose in the vendor war if you're not the one that not just is recommended in AO, but where the agent says, I will just do it with this API.”
Jason Lemkin Aug 28, 2026 ▶ 51:25 Who Owns Your Data Now? Agents vs. Systems of Record on The Agents #013
Insight
Bialecki: Headless software is the new default as user interfaces become infrastructure
“What we tend to think of as software. I now think of as its infrastructure. It's just a means to an end. So if you build some amazing UI, that's great. Like there might be, there are a lot of humans that will still use that some AIs, but the reality is like he…”
Andrew Bialecki Aug 14, 2026 ▶ 18:32 Agents Are Your New Power Users: How Klaviyo CEO Andrew Bialecki Is Remaking a $1.4B Business
Insight
Bialecki: Fuzzy human workflow interfaces fail when deploying AI agents
“I know this feels, look, a lot of humans, we're used to these kind of fuzzy interfaces, and then we'll meet, we'll have meetings to kind of figure out what he's first going to do. I think that it's not a great way to work, honestly, and it doesn't work with ag…”
Andrew Bialecki Aug 14, 2026 ▶ 26:40 Agents Are Your New Power Users: How Klaviyo CEO Andrew Bialecki Is Remaking a $1.4B Business
Insight
Bialecki: AI agent products requiring manual implementation are dead on arrival
“I think for a lot of agents, if you can't try that product out of the gates and it requires an indication, you're dead on arrival.”
Andrew Bialecki Aug 14, 2026 ▶ 36:25 Agents Are Your New Power Users: How Klaviyo CEO Andrew Bialecki Is Remaking a $1.4B Business
Insight
Lemkin: Context-rich AI agents act as proactive team members, not tools
“What's changed is the agents have so much context. They're aware of so much that every single day when you log in, especially with you, when you log in with 10 K now our AI VP of revenue, it has new things that wants to build and do. It's not a software tool. …”
Jason Lemkin Aug 5, 2026 ▶ 6:37 The Agents #12 - Our AI Agent Rewrote Our App Without Telling Us
Insight
Lemkin: AI agents autonomously selecting software lock vendors out of deals
“The agent made the call for a heat map vendor We'd never heard of, and we didn't even need to do more diligence. You trusted the agent. Someone lost a 50, 20, a twenty-k deal out there to an agent, and you, they were never, and this paid vet, this other, this …”
Jason Lemkin Aug 5, 2026 ▶ 17:13 The Agents #12 - Our AI Agent Rewrote Our App Without Telling Us
Insight
Lemkin: Running Claude over Replit via MCP forces cleaner code completion
“These models are goal-seeking, right? And they want to finish projects. So Replit just wants, Amelia, you know this, Replit wants to finish. Replit wants to finish, and so does CloudCode if you use it on an own. But when, but if you use Cloud on top of it coun…”
Jason Lemkin Jul 17, 2026 ▶ 6:27 How Agents Will Steal Your Customers. Plus: The $10K App Our Agent Replaced and the $14 Migration
Insight
Lemkin: Software Moats Are Shallower in the Age of AI
“Moats still exist in the age of AI, but they're just like shallower, so you better fucking deliver value.”
Jason Lemkin Jul 17, 2026 ▶ 35:30 How Agents Will Steal Your Customers. Plus: The $10K App Our Agent Replaced and the $14 Migration
Insight
O'Driscoll: VCs Are Hedging Between Foundation Models and SaaS
“No one knows the answer and most VCs are betting both ways. They're chucking a bunch of money in at a modest 300 or six hundred billion pre at Antropic. And at the same time, they're doing a whole bunch of investments that only make sense if in fact there is r…”
Rory O'Driscoll Jul 15, 2026 ▶ 14:46 Software Isn't Dead. It's Gotten Harder with Scale Venture Partners' Rory O'Driscoll
Insight
O'Driscoll: One-Third of Plain Vanilla SaaS Is Threatened by AI
“And then there's about a third way you're absolutely threatened, where you are typically what we call plain vanilla SaaS. You automate a workflow, and then you either got to move and survive, or you're going to be dead, right?”
Rory O'Driscoll Jul 15, 2026 ▶ 24:22 Software Isn't Dead. It's Gotten Harder with Scale Venture Partners' Rory O'Driscoll
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