The Ledger
Every statement that passed quotation and attribution checks. Mix any filter with any other: certainty 1/5, debate potential 5/5, or both at once.
why aren't all 21 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
Grady: Passing on Segment and Revolut Series A rounds were terrible mistakes
“I met both of them at the Series A, and both of them told me the entire story in like five or 10 minutes. And it was super clear. And at the end of the five or 10 minutes, I couldn't think of any questions to ask because they had already answered any question …”
Lemkin: Twilio Has Failed to Profit From Segment After Multi-Billion Acquisition
“It hasn't been able to make segment, make any money. Which it's paid billions of dollars for.”
No SaaS firm Cabane advised reached $50M ARR on a single channel
“And I have never seen a companies I've worked with, neither at Segment or at Drift, Gorgias, or Ram, and not in one of the companies I engage with, where we were able to get to fifty million on one channel. Not one.”
Niparko: Moving quickly is the key to unlocking higher product quality
“I think one of the things that we've learned at segment is that the faster you ship, the faster you learn all of the ways in which you were wrong. And all of the ways in which you can make it right. Reality and customers and procurement teams are very unforgiv…”
Grimshaw: Applying Stripe's Playbook to Segment Was Detrimental
“At Segment, there was a lot of pressure, and we did also in a positive way, learn lots of lessons from Stripe, but we were very different to Stripe, even though we would develop a sole product. And too much of the Stripe lesson was Detrimental actually to bein…”
Executives lacking humility have peaked in capacity and must be replaced
“I think if someone lacks humility, at least on some of those dimensions, yeah, they're not going to grow, so they're stagnant in their capacity, whatever that is. So to me, it's a huge warning sign, actually. If there's someone in the company or one of my dire…”
Verna: Segment closed enterprise deals using billboards outside target offices
“The, when they wanted to close an enterprise contract, they would buy a billboard right in front of that office and they would put their ad on that billboard addressing that company specifically. And it would be like the cheapest way to close a six, seven digi…”
Segment tracked engineer job changes using LinkedIn URLs for reverse attribution
“That's what we found at Segment. Really crazy attribution logic, where we found engineers across jobs by, and that's the unique lesson, keying not on the link, not on the email, because the email changes, domain changes, not on the name, that's not relevant, o…”
Zapier refused Segment's enterprise feature requests to maintain strict SMB focus
“I have one example. Zapier did that for very, very long. I talked to the Zapier founders. I talked to Mike when I was at Segment, and I wanted enterprise features, and he said, gee, we love you, but I'm sorry. We're not going to build those features. I'm like,…”
Twilio CEO Jeff Lawson spent 18 months convincing Reinhardt to sell
“No, you know, it took Jeff about 18 months to convince me that it was the right thing to do.”
Siroker: Optimizely tried and failed to acquire Segment
“Another example is segment. That's something, another area where it was adjacent to what we're doing. We tried to acquire them. They were later stage. Then they said, no, they ended up being successful.”
Niparko: Segment shifted resource allocation from 90/10/0 to 30/40/30 during expansion
“In the early days, that segment would swing pretty wildly between, you know, 90, 10, zero, really honing our, the quality of our core product in the early days to really periods of innovation where we're trying to Expand, build new products, and really solve n…”
Niparko: Segment over-focused on expansion over core integration quality
“And so I think there were periods where, you know, we weren't investing the right focus in integration quality. And I think that ended up showing up in some really hard conversations that we had with customers and realizing that we had probably been too focuse…”
Niparko: Segment never had a traditional Chief Product Officer
“At Segment we had a bunch of really technical founders, right? So we had four very talented, very product-focused, and very technical founders. We also brought in product-focused engineering leaders early on. We never really had a CPO in the traditional sense.”
Dorfman: Never build processes or teams before defining the problem
“Do not ever build a process or a structure or a team or anything until you know what problem you're trying to solve.”
Dorfman: Selling new software categories requires driving behavior change
“Selling into a new category is really challenging. It's a different type of challenge retools, a new category segment was a new category. You're not just selling a point solution. You're not just selling a product. You have to create budgets. You have to creat…”
Depth-first research builds superior mental models faster than surface learning
“I guess the way I approach things is very depth first. I think using a narrow curiosity to maximum benefit to just go insanely deep, In an area. So like, for example, if I have a meeting on diversity, equity, and inclusion, I'll go try to like read a few piece…”
Evaluate unfamiliar roles via output metrics or aggressive deep-dive learning
“Yeah, one way is to black box it and basically say, what is the outcome of great marketing? What's the outcome of great engineering? And measure the black box and not bother to inspect inside as to whether the box isn't, like, being done well internally, right…”
Grimshaw names GitHub, Segment, Benchling, and Monzo as top investment returns
“I think if you looked at Realized, it would probably GitHub or Segment. If you look at Unrealized, maybe Benchling or Monzo,”