The Ledger

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why aren't all 44 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 0 checkable ones are still open, waiting for their date. predictions held up or didn't; assertions are supported or contradicted. on every card: ▮▮▮▮▮ certainty · ▮▮▮▮▮ debate potential. speakers are clickable

Opinion
Lemkin: VCs tweeting about buying public tech stocks are losers
“And so when I see VCs on Twitter talking about how they're looking at buying some shares of Shopify, honestly, I think they're losers.”
Jason Lemkin Feb 3, 2023 ▶ 25:56 What Venture Looks Like In 2023 | SaaStr Founder Jason Lemkin + 20VC Host Harry Stebbings
Opinion
Deeter: Cloud leaders are superseding FAANG as tech growth drivers
“Our thesis internally is that those horizons and the growth rates of those markets are starting to pull back, and that you see a changing of the guard. And it's really the cloud basket, and we pulled out six names in particular with Microsoft, Twilio, Shopify,…”
Byron Deeter Oct 14, 2021 ▶ 5:09 State of the Cloud 2021 with Bessemer Venture Partners | SaaStr Software Community
Assertion Not publicly verifiable
Shopify sees an 80% annual merchant churn rate, warns Romain Lapeyre
“What was interesting is that the yearly churn is 80% for Shopify. It's pretty frightening, because at the end of the year, there's only going to be 20% of the stores that work here at the beginning of the year that will still be around and still be your custom…”
Romain Lapeyre May 15, 2019 ▶ 5:36 Lessons from Gorgias: How to Close your First 1000 Customers Based Solely on Data
Opinion
Lemkin: Shopify and Toast Would Be Mediocre Without Merchant Services
“Toast and Shopify is, if they were just software, they're pretty mediocre businesses, but they figured out how to add merchant services and payments and payrolls, and all the vertical SaaS companies are doing that.”
Jason Lemkin Jun 11, 2026 ▶ 29:25 $4 Trillion in IPOs, $100B in M&A, and Why B2B Spend is Booming
Insight
Benioff: Enterprise AI Requires a Unified Data Layer Connecting All Stores
“Whether it's Databricks or Snowflake, whether it's Shopify, whether it's BigQuery, whether it's All S three, all the places where you're storing data through your company, all of that needs to be one consistent data layer for that agent to be able to really be…”
Marc Benioff May 2, 2025 ▶ 36:17 AI, M&A, and the Future of SaaS: Lessons from Marc Benioff, Salesforce CEO, Co-Founder and Chair
Assertion Not checkable as stated
Padelford: Early Shopify won $50K deals against $900K Salesforce enterprise contracts
“The average enterprise deal in e-com at that time in history, you had Salesforce doing deals at eight, 900,000 dollars a year that we could do at 50.”
Loren Padelford Oct 8, 2024 ▶ 19:19 The Secrets to Selling and Scaling in Vertical SaaS with Slice's CRO
Insight
Tamir: On-premise infrastructure is cheaper for AI training if already established
“Maybe you buy your own infrastructure, which is also a cheaper answer. If you have, if you already have an infrastructure, an on-prem infrastructure system, that's really going to depend on what your AI training expectations are anticipated.”
Mike Tamir Apr 26, 2024 ▶ 13:36 How Shopify Implements AI Across Sales and Product with the Head of AI at Shopify
Assertion Supported
Lemkin: 70% of Klaviyo's Revenue Comes from Shopify Customers
“Klaviyo, which was the only IPO of this year is marketing just for e-commerce. In fact, Klaviyo really is just marketing only for Shopify customers. 70% of Klaviyo's almost one billion in revenue only not only comes from e-commerce, it only comes from Shopify”
Jason Lemkin Dec 28, 2023 ▶ 8:08 Is AI the Only Thing in SaaS that Anyone Cares About Anymore? AMA Part 1 w/ SaaStr CEO Jason Lemkin
Insight
Lemkin: Platform apps struggle unless they have day-one high attach rates
“There's these day one high attached vendors that make these applications blow up and the rest struggle, which doesn't mean you shouldn't do them, but it does mean it probably can't be everything for you.”
Jason Lemkin Dec 28, 2023 ▶ 13:26 Is AI the Only Thing in SaaS that Anyone Cares About Anymore? AMA Part 1 w/ SaaStr CEO Jason Lemkin
Insight
Job interviews are notoriously poor predictors of actual candidate performance
“Interviews are not that good at predictor performance. Actually, it's on the slide. and it's really just a way for you to figure out if somebody might be a fit for you. And so the shorter you can make that process, like I wouldn't recommend hours or hours lon…”
Farhan Thawar Feb 12, 2021 ▶ 17:07 How to Build a Great Intern Program from Scratch | @shopify VP of Engineering Farhan Thawar
Assertion Contradicted
Lemkin: Shopify data showed the pandemic software surge ended by summer 2020
“The twenty-twenty-one buying boom didn't end until Q one or Q two of twenty-twenty-two, but that's because they're a lag. If you go back and look, for example, at Shopify data and Shopify was very public. Shopify said in the summer of twenty-twenty, this is ov…”
Jason Lemkin Jul 8, 2026 ▶ 30:32 Agents Didn't Kill Sales. They Just Exposed It with SaaStrAI CEO and Founder Jason Lemkin
Assertion Supported
Lemkin: Shopify's 31% growth at $11B run rate is fastest in 3 years
“Shopify yesterday announced they crossed eleven billion dollar run rate, eleven billion dollars from Shopify. And It's accelerating. It's growing to 31% at 11.2 billion. That's even better than it sounds because that means it's added over three billion of new …”
Jason Lemkin Feb 19, 2025 ▶ 7:15 The 2025 SaaS Vibe Check: What Founders Need to Know Right Now with SaaStr Founder Jason Lemkin
Insight
Lemkin: SMB agencies standardize on one platform despite better competing products
“What they don't realize with SMBs is that like agencies and dev shops, They just pick one. They don't have time to learn for email marketing partners. They don't care if something's better than Shopify. I don't care. Shopify is number one.”
Jason Lemkin Dec 13, 2024 ▶ 26:57 From Outbound to Channel Partnerships: Your Burning Sales Questions Answered by Jason Lemkin
Assertion Partly supported
BILL has roughly 80% gross margins compared to Shopify's 50%
“It took forever, but as a result, you've got, you have, like, 80% gross margins. Shopify is like 50, toast is 30.”
Jason Lemkin Oct 22, 2024 ▶ 29:07 Approaching Half a Million Customers: How to Win in SMB | BILL CEO and Founder René Lacerte
Assertion Supported
Klaviyo holds roughly 60% market share in the Shopify ecosystem
“They have probably 60% market share in the Shopify ecosystem.”
Jason Lemkin Oct 22, 2024 ▶ 46:39 Approaching Half a Million Customers: How to Win in SMB | BILL CEO and Founder René Lacerte
Insight
Bialecki: Software architecture should be platform-agnostic with an indirection layer
“First is I think you definitely want to build, I think it's a good idea to build, you know, your underlying tech so that it's kind of agnostic, right? So there's a level of indirection in between what you solve for and the other folks that today and tomorrow c…”
Andrew Bialecki May 19, 2024 ▶ 32:52 Klaviyo's CEO Founder on the Journey to an $800,000,000 ARR Leader in Marketing
Insight
Lemkin: Shopify and Salesforce app ecosystems are dominated by the top 10
“When you look at partner ecosystems and we could flip it around and talk about Klaviyo's partner ecosystem too, it's almost always a long tail distribution. You could have a thousand apps on Shopify or Salesforce, but it's probably 10 that get half the install…”
Jason Lemkin May 19, 2024 ▶ 17:36 Klaviyo's CEO Founder on the Journey to an $800,000,000 ARR Leader in Marketing
Opinion
Bialecki: Shopify pioneered the developer ecosystem playbook that others now copy
“And again, I give Shopify a lot of credit for it. They, I think we're early to this game of realizing developers and building ecosystem mattered. I think a lot of folks have now tried to rinse and repeat their playbook.”
Andrew Bialecki May 19, 2024 ▶ 34:56 Klaviyo's CEO Founder on the Journey to an $800,000,000 ARR Leader in Marketing
Assertion Contradicted
Lemkin: Nearly 70% of Shopify merchants use Klaviyo
“Klaviyo owns marketing. About almost 70% of everyone on Shopify uses Klaviyo.”
Jason Lemkin May 3, 2024 ▶ 13:37 The 3 SaaS Metrics That Matter in 2024 with SaaStr CEO and Founder Jason Lemkin
Insight
Tamir: Search must balance direct and complementary relevance for optimal revenue
“And maybe what you would want to do is have one metric that shows for direct relevance and another that shows complementary relevance, right? And then it is somewhat a product decision of how much you want to balance these, but it's also something that you can…”
Mike Tamir Apr 26, 2024 ▶ 23:20 How Shopify Implements AI Across Sales and Product with the Head of AI at Shopify
Insight
Tamir: Search retrieval models learn most from near-miss negative training examples
“If I search for boots and I show a Christmas tree, that's not gonna, the model's not gonna learn much from saying, oh, that was wrong, right? It's gonna learn a lot more by showing its sneakers or by showing its sandals and saying that's because it's closer to…”
Mike Tamir Apr 26, 2024 ▶ 35:52 How Shopify Implements AI Across Sales and Product with the Head of AI at Shopify
Insight
Tamir: Per-token commercial LLM costs are unscalable for every enterprise query
“And if you pay a commodity LLM, which right now does usually beat out open source LLMs, you're going to end up paying per token and you can't scalably, if you have the right size of a business, do this for every query or every kind of use case.”
Mike Tamir Apr 26, 2024 ▶ 32:23 How Shopify Implements AI Across Sales and Product with the Head of AI at Shopify
Insight
Tamir: Successful ML teams require serving engineers and embedded product managers
“You need to have engineering for serving. You need to have your ML scientists and engineers, and you need to have product. You need to have product every year in the trenches with your ML builders.”
Mike Tamir Apr 26, 2024 ▶ 25:42 How Shopify Implements AI Across Sales and Product with the Head of AI at Shopify
Prediction Partly held up
Nahigian: Gorgias aims to automate 50% of merchant interactions within 12 months
“Initially it started to automate seven percent of tickets. It's gotten up to 18% today. They think within the next six to 12 months they'll be able to automate 50% of the back and forth interactions between e-commerce merchants and their end customers.”
TJ Nahigian Mar 1, 2024 ▶ 25:38 6 Questions Founders Should Ask Themselves to Drive Value from Generative AI with Base10 Partners
Insight
Robust internship programs make hiring experienced full-time employees significantly easier
“The other thing I found interesting is whenever I've had a really robust internship program, I find that it's easier to hire full times. And I think that's a combination of things, whether it's greater, a better sense of how to onboard, or even thinking throug…”
Farhan Thawar Feb 12, 2021 ▶ 5:16 How to Build a Great Intern Program from Scratch | @shopify VP of Engineering Farhan Thawar
Insight
Interns should have the exact same standing and access as full-time employees
“You have to think of them as your full times, and if you think of them as your full times, you should be taking their suggestions and feedback. You should be unblocking them. They should have the same level of access as everybody else.”
Farhan Thawar Feb 12, 2021 ▶ 9:25 How to Build a Great Intern Program from Scratch | @shopify VP of Engineering Farhan Thawar
Disclosure
Bernshteyn: Amazon manages tens of billions of dollars through Coupa
“You know, it's interesting with Shopify and Amazon. I mean, these are our customers, you know, Amazon runs the tens of billions they managed through Coupa.”
Rob Bernshteyn Jul 29, 2020 ▶ 13:40 What’s Changed Since March 15 The Cloud at Hyperspeed. The World in Flux.
Assertion Not publicly verifiable
Ferrara: Shopify grew ARR from $12M to $24M on just $2M burn in 2011
“One example I'll give of one of the best companies out there on this metric was Shopify, which is a company that in around 2011 had about twelve million of ARR. Over the next 12 months, they added Another twelve million of ARR, and it cost them two million to …”
Alex Ferrara Oct 30, 2019 ▶ 25:18 State of the Cloud 2019: Europa Edition | SaaStr Software Community
Assertion Partly supported
Lemkin: Box, HubSpot, and Shopify IPO'd at roughly $800M valuations
“When Rory invested in box with Aaron, when Rory's invested in HubSpot, those are pretty good ones. Shopify. These guys all IPO'd around a hundred million in revenue growing really fast off in 50, 60, 80% at like eight hundred million valuations.”
Jason Lemkin Aug 27, 2025 ▶ 7:02 What Happens When AI Kills Your SaaS Growth? Live Q&A with SaaStr CEO and Founder Jason Lemkin
Assertion Partly supported
Stripe's 2017 enterprise push was driven by Shopify, Lyft, and Squarespace
“So for Stripe in that first camp, this was back in 2017 that we started our foray into enterprise, and it was the Shopify's, the Lyft's, Squarespace's were all growing up, bringing in adult CFO's, contemplating IPOs, and so they had a bunch of demands.”
Jeanne DeWitt Grosser Feb 12, 2025 ▶ 4:59 The Playbook for Going Upmarket with Stripe's CBO and Checkr's COO
Disclosure
Lemkin: Gorgias has 16,000 Shopify customers, approaching $100M revenue
“I'm on the board of a company called gorgeous. Which is the largest contact center in e-commerce. And they've got about 16,000 Shopify customers coming up on a hundred million in revenue.”
Jason Lemkin Jun 26, 2024 ▶ 29:10 Forget the SaaS Gloom and Doom. Just Build. with SaaStr CEO and Founder, Jason Lemkin
Insight
Tamir: Gap between ML loss metrics and product goals determines AI success
“There, that gap between what I want to mathematically measure, which is how the machine is going to learn based on that error and what my actual product result is. Really matters.”
Mike Tamir Apr 26, 2024 ▶ 11:10 How Shopify Implements AI Across Sales and Product with the Head of AI at Shopify
Insight
Tamir: Rigorous evaluation culture is critical as non-experts deploy pre-trained AI models
“Having that strong culture to back up the performance of your model before you go into release is probably one of the biggest issues in terms of having a strong ML culture when you're, as it gets easier and easier for non-experts to start leveraging these tool…”
Mike Tamir Apr 26, 2024 ▶ 18:08 How Shopify Implements AI Across Sales and Product with the Head of AI at Shopify
Assertion Supported
Lemkin: Two-Thirds of Shopify Revenue Comes from Financial Services
“Two thirds of Shopify revenue comes from payments and financial services, not from software, right?”
Jason Lemkin Dec 28, 2023 ▶ 9:08 Is AI the Only Thing in SaaS that Anyone Cares About Anymore? AMA Part 1 w/ SaaStr CEO Jason Lemkin
Assertion Not checkable as stated
Lapeyre: 700k of 2M Shopify Stores Form Gorgias's TAM
“So for us, we sell mostly to Shopify stores. There are about two million of them. I think there's about like 700 K of them that are on our TAM.”
Romain Lapeyre Feb 11, 2022 ▶ 3:03 Acquiring 10,000 SMB Customers Solely from Data with Gorgias' CEO Romain Lapeyre
Assertion Not checkable as stated
Shopify stores account for approximately 95% of Gorgias's business
“We focus on Shopify right now. It's about like, 95% of our business, and we're starting to go on Magento and e-commerce and build those partnerships there.”
Romain Lapeyre Feb 11, 2022 ▶ 42:27 Acquiring 10,000 SMB Customers Solely from Data with Gorgias' CEO Romain Lapeyre
Assertion Supported
Shopify partners generated $12B in 2020 versus Shopify's $3B in revenue
“Shopify had almost three billion in revenue in 2020. And over twelve billion is what Shopify partners generated for themselves through the Shopify partner program that same year.”
Amanda Malko Dec 1, 2021 ▶ 16:26 The State of Software Buying From SMB to Enterprise with G2's CMO, Amanda Malko
Assertion Supported
42,000 Shopify partners referred at least one new customer in 2020
“42,000 partners in their community referred at least one new customer to Shopify that same year.”
Amanda Malko Dec 1, 2021 ▶ 16:40 The State of Software Buying From SMB to Enterprise with G2's CMO, Amanda Malko
Assertion Supported
D'Onofrio: Shopify grew 80% in 2020 to almost $3 billion
“In 2020, it actually grew an incredible 80% In the new normal to almost three billion of revenue.”
Mary D'Onofrio Mar 14, 2021 ▶ 30:02 The State of the Cloud: 2021 with Bessemer Venture Partners | SaaStr Software Community
Assertion Supported
Shopify's Dev Degree pays university tuition while students complete their internships
“Shopify has a, has an interesting program called dev degree. And what dev degree is, it's a program in conjunction with a few schools whereby you get your university paid for and you do your internships all at Shopify.”
Farhan Thawar Feb 12, 2021 ▶ 44:40 How to Build a Great Intern Program from Scratch | @shopify VP of Engineering Farhan Thawar
Disclosure
Deeter: Bessemer invested in Twilio, Shopify, and Pinterest during 2008 crisis
“Three in the Bessemer portfolio alone, we had Twilio, Shopify, and Pinterest were all, you know, seed and series A investments coming out of that O eight crisis.”
Byron Deeter Mar 27, 2020 ▶ 22:20 The Current State of Venture Capital and Cloud | SaaStr Software Community
Assertion Supported
Shen: Shopify grew from $12M to $24M ARR burning only $2M
“Well, if you take a look at Shopify, they were twelve million ARR in year one, and grew to twenty four million ARR in year two. And so they had an increase of twelve million in net new ARR, but only burned two million to do it. And so they had a six X BVP effi…”
Christina Shen May 20, 2019 ▶ 25:16 State of the Cloud 2019 from Bessemer Venture Partners
Assertion Supported
Deeter: Over half of Shopify's revenue comes from payments
“Now, for those of you that look at the public filings of Shopify another proud Bessemer alumni portfolio company, they're trading at ten billion dollars plus. And over half of their revenue today is from this emerging category of payments.”
Byron Deeter May 3, 2018 ▶ 23:55 State of the Cloud: 2018 Edition
Assertion Supported
Justin Betakure: Coinbase, Shopify, and Brex use remote-first models with hubs
“Remote first is what Coinbase and Shopify and Brex are doing, where they run the entire company remotely from asynchronization to all hands done remotely, but they have hubs where you can, almost like a cafe, where you can go in and visit colleagues or even do…”
Justin Betakure Mar 11, 2022 ▶ 3:47 How Hybrid is Working in Practice: What the Data Shows | Raise Comm. Real Estate CEO + President
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