The Ledger

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Opinion
Lemkin: GitLab is not really a SaaS company
“GitLab just IPO to sixteen billion. It's not really a SaaS company.”
Jason Lemkin Dec 9, 2021 ▶ 35:53 Ask Me Anything About Customer Success with SaaStr CEO Jason Lemkin and ChurnZero CEO You Mon Tsang
Opinion
Ghodsi: All proprietary software is vulnerable to disruption by open source
“In fact, I think open source has the potential to replace pretty much any software that's, Any proprietary software that exists on the planet today is, you know, in a really vulnerable state in the sense that it can be disrupted by an open source version, righ…”
Ali Ghodsi Dec 7, 2021 ▶ 17:12 The Future of AI, Open Source, and Enterprise SaaS with Databricks CEO Ali Ghodsi
Opinion
Lemkin: Reduced VC collaboration is strictly better for founders
“Without question. And without question, it's better for founders. Without question. Every element of venture that is, and I'm being binary when it's off course more subtle than this, but every much of the collaboration in venture did not benefit founders, righ…”
Jason Lemkin Nov 30, 2021 ▶ 5:03 Scaling a Successful SaaS Sales Team w/ 20VC Founder Harry Stebbings and SaaStr Founder Jason Lemkin
Opinion
Lemkin: Multi-billion-dollar VC funds do not care about losing $20M checks
“The funds are so big, and they're raising funds every 12 months, right? In my, we have different portfolios. In my portfolios, when the multi-billion dollar funds have come in and led the A or the C, they're barely invested. They're, and you know what? They do…”
Jason Lemkin Nov 30, 2021 ▶ 36:43 Scaling a Successful SaaS Sales Team w/ 20VC Founder Harry Stebbings and SaaStr Founder Jason Lemkin
Opinion
Barrett: High startup valuations are bullshit caused by excess stimulus money
“I just think it's all bullshit. Like, I think the reason the valuations are high is because there's a shit ton of money in the markets, and it has no place to go. Like, there's, we just printed, what, three and a half trillion dollars of stimulus money out of …”
David Barrett Nov 17, 2021 ▶ 2:26 The Highs and Lows of Fundraising from Founders That Have Raised $1B w/ Calendly, Coda, LaunchDarkly
Opinion
Barrett: High-Funded SaaS Startups Rely on Burning Cash, Not Acquisition Innovations
“Most of the companies rating it as shit tons of money, they, they're not using, like, novel customer acquisition techniques that couldn't have worked 20 years ago. They're just willing to lose more money on it. And then the VCs are willing to allow them to los…”
David Barrett Nov 17, 2021 ▶ 4:15 The Highs and Lows of Fundraising from Founders That Have Raised $1B w/ Calendly, Coda, LaunchDarkly
Opinion
Barrett: Raising a gigantic VC war chest ruins company culture
“This whole idea of getting a gigantic war chest, I think that's bullshit. Like, I think that it's just a big waste of money and capital, and it just, like, ruins your company's culture.”
David Barrett Nov 17, 2021 ▶ 11:52 The Highs and Lows of Fundraising from Founders That Have Raised $1B w/ Calendly, Coda, LaunchDarkly
Opinion
Barrett: In startup funding rounds, VCs always win and employees rarely win
“Again and again, every single big round we have, the employees get fucked. And there's a whole bunch of reasons for that. It's like the VCs always win. The founders sometimes win. The employees rarely win.”
David Barrett Nov 17, 2021 ▶ 30:26 The Highs and Lows of Fundraising from Founders That Have Raised $1B w/ Calendly, Coda, LaunchDarkly
Opinion
Barrett: Avoid venture capitalists as long as possible
“I would avoid the VCs as long as possible, because they're the devil. Now, don't get me wrong, sometimes you need to do a deal with the devil, but you're probably gonna get fucked in the process.”
David Barrett Nov 17, 2021 ▶ 43:38 The Highs and Lows of Fundraising from Founders That Have Raised $1B w/ Calendly, Coda, LaunchDarkly
Opinion
Butterfield: Microsoft Teams competes primarily with Zoom rather than Slack
“Teams, which is the real alternative in some sense, although I think it's much more of a competitor to Zoom or other voice and video calling services than it is a Slack.”
Stewart Butterfield Apr 28, 2020 ▶ 25:47 Taking Care Of Your Team and Your Customers with Slack | SaaStr Software Community
Opinion
Gunderson: Most Silicon Valley VCs have no understanding of tech
“When I first came out, I was like, holy shit, most of these VCs have no, you know, no idea in regards to tech”
Eric Gunderson Aug 28, 2018 ▶ 12:25 Bootstrapping vs Fundraising
Opinion
Barrett: A predatory executive class exploits startups with false credentials
“There's a whole class of people out there preying upon startups that will just come in with amazing credentials and a willingness to obliterate whatever's in their way and because it's not their company in the first place.”
David Barrett Jan 8, 2018 ▶ 38:00 Good Intentions, Bad Advice: How to Keep Your Board Aligned with Your Vision
Opinion
Fraden: 50% of the fastest-growing SaaS companies turned out to be garbage
“I bet if you went back over the last five years and looked at the top three or four companies in each of those five years that were at that point in time the fastest growing SaaS companies in history, I bet a solid 50% of those companies turned out to be garba…”
Russ Fraden Dec 20, 2017 ▶ 13:28 How the Relationship Changes Between CEO and VP Sales After Funding
Opinion
Siroker calls Adobe's marketing cloud a poorly integrated 'Franken-suite'
“Adobe you know, has a product that, you know, has been evolved through acquisitions, which turns what they're offering into what our customers tend to describe as a Franken-sweet. It's a bunch of products that don't really integrate well with one another.”
Dan Siroker Jul 7, 2017 ▶ 5:22 How to Break Out and Really Scale
Opinion
Lemkin: AI SDR emails beat 99% of humans but lack deep context
“The artisan Monaco agent force emails. They're all better than a human, which is all that really matters today as we record this, right? They're better than 99% of humans. But they're not great like that RepliDeck. None of them are great.”
Jason Lemkin Aug 28, 2026 ▶ 36:17 Who Owns Your Data Now? Agents vs. Systems of Record on The Agents #013
Opinion
Lemkin: Custom AI tools outperform $50k to $80k commercial SaaS solutions
“Is that listen, you could buy this functionality exists in other products, or you could buy it for 50 grand or 80 grand a year today, right? But because it is a well-known body of software, Claude knows it. So Claude can just build it for you. Buy, don't build…”
Jason Lemkin Aug 5, 2026 ▶ 14:19 The Agents #12 - Our AI Agent Rewrote Our App Without Telling Us
Opinion
Lemkin: Claude's MCP capabilities threaten dedicated agent orchestration startups
“It is a threat to folks that are building these sort of agent substrates, which is that we, listen, every time we talk about our agents and stuff, a bunch of folks will tweet back or say, Hey, listen, I've got the substrate. I've got the, I've got a way to con…”
Jason Lemkin Jul 17, 2026 ▶ 15:01 How Agents Will Steal Your Customers. Plus: The $10K App Our Agent Replaced and the $14 Migration
Opinion
Millions Need Video, but Only Hundreds of Thousands Want to Prompt
“We made a bet that number of people who need social media video, number of people who want to sell is probably tens of millions of users, but number of people who want to learn prompt engineering is probably hundreds of thousands.”
Alex Mashrabov Jul 10, 2026 ▶ 9:52 $0 to $700M ARR in 16 Months. Inside Higgsfield's AI Growth with Alex Mashrabov, co-founder and CEO
Opinion
Lemkin claims it is entirely impossible to build sales relationships over Zoom
“I think it is impossible to build a relationship on zoom.”
Jason Lemkin Jul 8, 2026 ▶ 13:28 Agents Didn't Kill Sales. They Just Exposed It with SaaStrAI CEO and Founder Jason Lemkin
Opinion
Buyers re-evaluating every 8-10 months means there is no AI land grab
“I, I'm not sure that there's a land grab in AI today. Because there's a counter trend, which is that so many folks I know of who are blowing up here, who are doing five million their first month, ten million their first two months. Customer, there is budget fo…”
Jason Lemkin Jul 8, 2026 ▶ 41:14 Agents Didn't Kill Sales. They Just Exposed It with SaaStrAI CEO and Founder Jason Lemkin
Opinion
Lemkin: AI Agents Expanded Customer Support and Legal SaaS Markets 100x
“These Sierra Decagons, and also legal Harvey, these were niche markets before agents. These were niche markets that are like 10 to a hundred times larger because the agents add so much value.”
Jason Lemkin Jun 11, 2026 ▶ 47:52 $4 Trillion in IPOs, $100B in M&A, and Why B2B Spend is Booming
Opinion
Masad: Many software engineers are laggards in adopting AI agents
“I actually think engineers are laggards. Not all engineers, but like a lot of engineers are because they're kind of tied to their workflows.”
Amjad Masad Jun 9, 2026 ▶ 2:49 What Agents That Actually Work Look Like Right Now with Replit's CEO and Founder
Opinion
Masad: Replit's memory compaction algorithm beats Claude's
“We actually think ours is much better than Claude and many others on the market.”
Amjad Masad Jun 9, 2026 ▶ 6:24 What Agents That Actually Work Look Like Right Now with Replit's CEO and Founder
Opinion
Masad: AI agents face a huge hype gap and disillusionment trough
“I think agents, the hype in agents versus the reality is huge. Like, there's a huge delta, and eventually there's going to be this trough of disillusionment.”
Amjad Masad Jun 9, 2026 ▶ 39:16 What Agents That Actually Work Look Like Right Now with Replit's CEO and Founder
Opinion
Lemkin: 99% of successful GTM agents are optimized around Salesforce
“In GTM, I think, 99% of the agents that are working today, that are successfully are optimized around Salesforce.”
Jason Lemkin May 12, 2026 ▶ 56:08 Our AI is Hiring! Would You Work for One? And Are Autonomous Agents ... Safe? The Agents #005
Opinion
Lemkin: Marketo API Fails for AI Agents, Graded a 'C'
“If you go down to Marketo where the API doesn't work, right? You can find it down in the C's or even search for it. It will explain to you if you want to build an agentic product, don't use Marketo.”
Jason Lemkin May 6, 2026 ▶ 23:45 Why Your Next Hire Should Report to an AI, Tragedy Apps, and Too Many AI SDRs? | The Agents #004
Opinion
Wilson: Reaching $100M ARR with Two Reps Is Unrealistic for Most
“That's why I don't really buy yet into, okay, we're gonna have two reps, and we're gonna get to a hundred million, like, sure, that works if you're lovable, like, that can work with the right business, but a lot of us do not have that business, so to hold ours…”
Ashley Wilson Apr 1, 2026 ▶ 33:20 How AI Is Rewiring Sales: Quota, Retention & Follow-Up with Agentforce, Momentum, Mangomint + SaaStr
Opinion
Lemkin: Current AI SDR tools cannot autonomously auto-segment effectively
“None of the AI tools we use today, which are all great, but none of them can really use AI to auto segment in a way that can deliver these results.”
Jason Lemkin Mar 18, 2026 ▶ 19:43 10 Things to Know Before You Deploy Your First AI SDR
Opinion
Lemkin: All third-party AI agents are less secure than Salesforce
“The honest truth is no agents, no third party agents are more secure than Salesforce. They're all less secure is the reality of it.”
Jason Lemkin Mar 4, 2026 ▶ 35:32 The Top 5 Issues Managing Multiple AI Agents in Production
Opinion
Lemkin: Inbound AI is the lowest-hanging fruit for 98% of software companies
“I'll tell you the lowest hanging fruit for 98% of folks out there. I know I use different nomenclatures than some is adding AI to inbound.”
Jason Lemkin Jan 21, 2026 ▶ 34:51 The Present and Future of AI in Sales and GTM with SaaStr's CEO and Owner's CRO
Opinion
Lemkin: Agentforce takes more setup work but outperforms in production
“Asian force is more work to set up than the rest of the agents, but it is good or better in production. It is as good because they're all good. Okay. All the good ones are good. They're all kind of the same. The emails are pretty similar, right? It is better b…”
Jason Lemkin Jan 21, 2026 ▶ 45:50 The Present and Future of AI in Sales and GTM with SaaStr's CEO and Owner's CRO
Opinion
Lemkin: Customers Rejected Microsoft's $20 Per Month Word Copilot
“No one wanted to pay an extra 20 bucks a month to talk to word. Okay. That was the great innovation. And even Microsoft couldn't get people to buy that. It doesn't work. No one wants a mediocre co-pilot.”
Jason Lemkin Jan 2, 2026 ▶ 46:06 AI + B2B in 2026: Find the Tailwinds or Get Left Behind | Jason Lemkin
Opinion
Lemkin: Enterprise Demand for Salesforce's Agentforce is Just Getting Started
“I'm not telling you to go buy public stocks, but I'd be long on Salesforce, even if the market wasn't true this year, because it's just getting going with the spike. The demand is just getting going.”
Jason Lemkin Jan 2, 2026 ▶ 47:56 AI + B2B in 2026: Find the Tailwinds or Get Left Behind | Jason Lemkin
Opinion
Ibarra: AI Lets Companies Clone A-Players and Make Them S-Tier
“I think there is now, I think, a clear path to where I'm seeing in these platforms. You can clone all your best A players, right? Take all the best A players on your team across marketing, sales, CS, sales, rev ops, and make them S tier with AI. I truly believ…”
Amelia Ibarra Nov 21, 2025 ▶ 7:36 6 Months Later, How Our AI SDRs Actually Work as AI Runs GTM with SaaStr's CEO and Chief AI Officer
Opinion
Ibarra: Expecting immediate ROI and headcount cuts from AI is false
“Jason's point on like immediate ROI and headcount is a hugely false expectation that I hope nobody has on this call, but if you had it maybe going into this, can kind of course correct on where you're going to see lift.”
Amelia Ibarra Nov 21, 2025 ▶ 12:34 6 Months Later, How Our AI SDRs Actually Work as AI Runs GTM with SaaStr's CEO and Chief AI Officer
Opinion
Queener: Anthropic's MCP is destroying historical software integration walled gardens
“MCP, if you don't, haven't dug into it, is game changing. It is destroying historic walled gardens from an integration perspective.”
Brett Queener Oct 31, 2025 ▶ 8:19 Why Only “WTF” Products Can Survive Today with Brett Queener Partner at Bonfire Ventures
Opinion
Queener: Startups must work in-office because rapid iteration requires it
“You're going to be in the office. We're going to iterate because the iteration loops are so fast in this new era. It's just not going to work otherwise.”
Brett Queener Oct 31, 2025 ▶ 16:50 Why Only “WTF” Products Can Survive Today with Brett Queener Partner at Bonfire Ventures
Opinion
VCs Have Zero Interest in Classic SaaS Companies Growing 80%
“There is no interest in classic SAS companies from VCs growing at pretty good rates. If you're growing 80% at twenty million or 70% at fifty million, it's not cool, dude, but there, no one's going to fund you. Nobody.”
Jason Lemkin Oct 22, 2025 ▶ 40:14 The State of AI + Software: Where It’s Going - Fast
Opinion
Lemkin: Vibe coding apps like Salesforce in 10 minutes is dangerous bologna
“There's a lot of stuff on social media about, Hey, you can just vibe code your own HubSpot or Salesforce. You can vibe code your own notion. It will take. 10 minutes. That's Sony baloney. And it is almost dangerous Sony baloney because it's not just startups t…”
Jason Lemkin Sep 12, 2025 ▶ 2:55 The Complete Guide to Vibe Coding without a Developer with SaaStr CEO and Founder Jason Lemkin
Opinion
Sloan: PPC advertising can no longer buy growth for B2B marketers
“And PPC is no longer the way that we can buy our way. We have to figure out a new way.”
Sydney Sloan Sep 10, 2025 ▶ 7:07 Swapping Notes on the AI Revolution in Marketing with G2's CMO Sydney Sloan
Opinion
Cursor's Jacob Jackson: AI Tools Have Already Accelerated Many Developers Over 2X
“I think many people have been accelerated more than two X by this technology already. And the technology is only going to get better. So I think comparing it to the developer salary is the right way to look at it.”
Jacob Jackson Sep 5, 2025 ▶ 8:37 Anthropic, Cursor, FaL & Bessemer Venture Partners: The Realities of Scaling AI
Opinion
Lemkin: Only 20% to 30% of VCs still back classic T2D3 growth
“If you're triple, triple, double, double, as hard as that is, as hard as that is, maybe only 20 to 30% of the investors that would have been interested, 18 months ago today, 20%, 20, 30%.”
Jason Lemkin Aug 27, 2025 ▶ 9:00 What Happens When AI Kills Your SaaS Growth? Live Q&A with SaaStr CEO and Founder Jason Lemkin
Opinion
Trillions in App Value Remains Even If AI Models Stop Improving
“That even if you froze the model capabilities, there's trillions and trillions of dollars of applications just waiting to be discovered here.”
Jacob Effron Aug 13, 2025 ▶ 4:06 Redpoint Ventures Playbook: How Top VCs Are Really Investing in AI with Jacob Effron
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
Lemkin: Most CMOs excel at two functions and are mediocre elsewhere
“Most CMOs have like two or three things they like to do and the rest, they sort of hand off to their team or are mediocre at it.”
Jason Lemkin Jul 16, 2025 ▶ 16:28 Marketing in the Age of AI with Wiz's CMO Raaz Herzberg
Opinion
Levie: Model Context Protocol integrations enhance rather than erode enterprise software moats
“I would actually argue that MCP is a thing that only enhances the underlying moat. Because data wants to be free. That doesn't mean that there's no moat around managing the data and making it useful. It wants to be incorporated in some other workflow. So for u…”
Aaron Levie Jul 2, 2025 ▶ 25:44 Why Enterprise AI Adoption Is Moving 5-10X Faster Than Cloud with Box 's Aaron Levie and IBM's VP AI
Opinion
Rangan: Modern software products must have embedded AI, not separate SKUs
“There were a lot of folks building an AI skew with an AI price and like a separate thing that you would do. And I think for us it is, did anybody buy black and white TV after a color TV came out? The answer is no. So you, when after AI, there is no product tha…”
Yamini Rangan Jun 4, 2025 ▶ 22:09 AI and The Future of Sales, Marketing & CS with HubSpot CEO Yamini Rangan
Opinion
Rangan: Enterprise software requires both co-pilots and autonomous agents
“In the industry, there's just a lot of confusion about what is a co-pilot? What is an agent? Do you need both? And there's a fight over. You don't need co-pilots. You only need agents. And the simplified version is you actually need both. Co-pilots help you do…”
Yamini Rangan Jun 4, 2025 ▶ 23:00 AI and The Future of Sales, Marketing & CS with HubSpot CEO Yamini Rangan
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