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.

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why aren't all 15 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
Shah dislikes legal AI, but invested in Ironclad for Jason Boehmig
“I actually hate the space that he's in. He's kind of in the legal kind of AI space. I don't like that market, but Jason is so compelling that it's just a pleasure to work with someone like him.”
Semil Shah Oct 23, 2017 ▶ 25:53 20VC: Semil Shah on How To Raise An Institutional Venture Fund, Why LPs Mostly Have Reserve Allocation Theory Wrong & Why IPOs and Acquisitions Are Severely Constrained
Insight
Boehmig: Extending job offers without complete conviction is a mistake
“If you have an iota of doubt in the hiring process, and you feel like you could not be that disappointed if this person didn't join, anytime that we haven't gotten to complete certainty, I think is a mistake. And you should almost be heartbroken if the person …”
Jason Boehmig Oct 4, 2019 ▶ 20:11 20VC: How To Drop The BS and Relationship Build With Investors, What Investors Can vs Cannot Help Your Company With & Why When There Is Doubt There Is No Doubt In Hiring
Prediction Not checkable as stated
Boehmig: Legal tech adoption will increase during an economic downturn
“And I'll actually say that I'm excited for a recession or a downturn, because legal is a extremely counter cyclical industry. And I think now that we've established ourselves as a market leader within our vertical, that we're going to see a lot of folks actual…”
Jason Boehmig Oct 4, 2019 ▶ 15:57 20VC: How To Drop The BS and Relationship Build With Investors, What Investors Can vs Cannot Help Your Company With & Why When There Is Doubt There Is No Doubt In Hiring
Assertion Supported
Ironclad built an AI product named Jurist that competes with Harvey
“And in addition to contract management, which is a much, you know, bigger thing, we also have this AI product that we've built. It's called Jurist, which is a Harvey competitor. It's pretty cool. And it's grown real quick.”
Jake Saper Mar 10, 2025 ▶ 1:24:39 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Disclosure
Jake Saper lost the Ironclad deal to Jess Lee at Sequoia
“The first deal I lost, I think I've lost two or three deals in my career so far. The first deal I lost was Ironclad. And I lost it to Jess Lee at Sequoia.”
Jake Saper Mar 10, 2025 ▶ 1:22:48 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Disclosure
Saper: Top Emergence investments like Zoom were expensive, but Veeva wasn't
“They are not always expensive, but they are often expensive. So if I look back at our portfolio, Gusto was expensive. Zoom was expensive. Yammer was expensive. A lot of the good ones, Ironclad was expensive. But some of them weren't. Viva wasn't expensive beca…”
Jake Saper Mar 10, 2025 ▶ 24:25 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Assertion Supported
Ironclad has surpassed $100 million in annual revenue
“The company's now north of a hundred million in revenue.”
Jake Saper Mar 10, 2025 ▶ 1:24:07 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Insight
Boehmig: Treat VC board member selection like hiring key team members
“I really look at our board members as Being parts of the team and putting just as much effort into hiring them as we do with a normal team member.”
Jason Boehmig Oct 4, 2019 ▶ 26:05 20VC: How To Drop The BS and Relationship Build With Investors, What Investors Can vs Cannot Help Your Company With & Why When There Is Doubt There Is No Doubt In Hiring
Insight
Boehmig: Early startup hires are sold on team dynamics over company vision
“And if we look at our second employee, it was someone that I had worked with at a previous job, and we just got along great. And that teamwork vibe was the selling point there, as opposed to even the vision of the company at that point. So super hustly and net…”
Jason Boehmig Oct 4, 2019 ▶ 17:29 20VC: How To Drop The BS and Relationship Build With Investors, What Investors Can vs Cannot Help Your Company With & Why When There Is Doubt There Is No Doubt In Hiring
Insight
Boehmig: Hyper-local geographic constraints accelerate early startup product iteration
“So that rapid iteration and actually constraining ourselves to a really small geographic area, I think, helped us move a lot faster than companies that are trying to go on a much larger scope right from the beginning.”
Jason Boehmig Oct 4, 2019 ▶ 10:57 20VC: How To Drop The BS and Relationship Build With Investors, What Investors Can vs Cannot Help Your Company With & Why When There Is Doubt There Is No Doubt In Hiring
Disclosure
Boehmig: Early advisors told Ironclad not to sell to the legal vertical
“A lot of people told us to not sell to the legal vertical. You know, these people haven't bought software before. They're not going to be the base for building a game-changing technology company. It's kind of a backwater. Don't do that.”
Jason Boehmig Oct 4, 2019 ▶ 7:07 20VC: How To Drop The BS and Relationship Build With Investors, What Investors Can vs Cannot Help Your Company With & Why When There Is Doubt There Is No Doubt In Hiring
Assertion Not publicly verifiable
Boehmig: Ironclad's sixth hire rose from data entry to head of support
“When we look at employee six, who joined right after Toby, doesn't have a college degree, started doing data entry for us for, I think, 10 bucks an hour, and was so thoughtful and humble and motivated and competent at doing that, that we just kept giving her m…”
Jason Boehmig Oct 4, 2019 ▶ 19:19 20VC: How To Drop The BS and Relationship Build With Investors, What Investors Can vs Cannot Help Your Company With & Why When There Is Doubt There Is No Doubt In Hiring
Insight
Boehmig: Reducing complex legal work to checklists maximizes impact
“If you can reduce routine work to a simple checklist and do the same thing each and every time, it's one of the best ways to have an impact in anything from surgical outcomes to legal transactions. And so what ironclad does is actually puts a checklist for eac…”
Jason Boehmig Oct 4, 2019 ▶ 35:25 20VC: How To Drop The BS and Relationship Build With Investors, What Investors Can vs Cannot Help Your Company With & Why When There Is Doubt There Is No Doubt In Hiring
Disclosure
Boehmig: Ironclad initially aimed to be the top contract platform in SoMa
“And so we actually set up with this goal to become the number one contract platform in Soma. And that was all we cared about. We just wanted to be the number one contract platform in Soma.”
Jason Boehmig Oct 4, 2019 ▶ 10:21 20VC: How To Drop The BS and Relationship Build With Investors, What Investors Can vs Cannot Help Your Company With & Why When There Is Doubt There Is No Doubt In Hiring
Assertion Not checkable as stated
Boehmig: How to build a CEO leadership style as an introverted founder
“This is part of my own personal journey as a CEO is I don't think I'm a typical CEO. I'm kind of an introvert. I'm almost a little shy in many ways. And I don't think that I fit the classic mold of a CEO, but I've looked at other CEOs and I've been able to tak…”
Jason Boehmig Oct 4, 2019 ▶ 8:50 20VC: How To Drop The BS and Relationship Build With Investors, What Investors Can vs Cannot Help Your Company With & Why When There Is Doubt There Is No Doubt In Hiring
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