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.

clear all ✕

why aren't all 18 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

Insight
Bookman: Reversing OpenGov's Remote Policy Because In-Office Productivity Is Far Superior
“And the reality is I was dead wrong. We're getting back into the office. The collaboration, the productivity, like, it's not even close, and it's very painful getting back into the office, and you know what is worse than that? It's not getting back in the offi…”
Zachary Bookman Dec 6, 2024 ▶ 1:12:48 Zachary Bookman: Why Valuations and Fundraising are BS | E1235 · 20VC with Harry Stebbings
Opinion
Lonsdale: Lean startup methodology is useless for complex enterprise companies
“The whole lean startup movement I thought was bullshit when it was happening in terms of the things I wanted to do. There definitely was a lean startup movement. Didn't make sense at all for the areas I wanted to work on and focus on. You couldn't have done a …”
Joe Lonsdale Jul 7, 2020 ▶ 15:19 20VC: 8VC's Joe Lonsdale on How To Foster Contrarian Thinking Within Venture Partnerships, Why The Best VCs Are Company Builders & Why It Is Not Possible To Build Multi-Billion Dollar Companies and Have Worklife Balance
Insight
Bookman: Multi-billion dollar exits do not move the needle for top VCs
“OpenGov's been quite successful, but it doesn't move the needle. It's a couple billion dollar type exit. That's not what you're in the game for.”
Zachary Bookman Dec 6, 2024 ▶ 10:14 Zachary Bookman: Why Valuations and Fundraising are BS | E1235 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Bookman: Marc Andreessen walked out of board meeting exactly at scheduled end
“I scheduled a two-hour board meeting, and the board was opening up, a lot of give and take, big discussion going on, some important issue, so I decided to let it run, and at, you know, maybe it was 10 a.m. To 12 p.m. At 12 p.m., Mark literally just pulls his c…”
Zachary Bookman Dec 6, 2024 ▶ 56:50 Zachary Bookman: Why Valuations and Fundraising are BS | E1235 · 20VC with Harry Stebbings
Insight
Bookman: Startups should launch secondary product lines as early as possible
“I think is, is the earlier, the better.”
Zachary Bookman Dec 6, 2024 ▶ 29:26 Zachary Bookman: Why Valuations and Fundraising are BS | E1235 · 20VC with Harry Stebbings
Disclosure
Bookman felt for years that building OpenGov ruined his career
“The short answer is yes. Basically all the time. I don't know how I kept going because I felt for years like I destroyed my career. I'd made the worst set of decisions.”
Zachary Bookman Dec 6, 2024 ▶ 31:19 Zachary Bookman: Why Valuations and Fundraising are BS | E1235 · 20VC with Harry Stebbings
Disclosure
Bookman: Cashed out 49% of his vested equity in OpenGov
“I took out 49% of my vested equity.”
Zachary Bookman Dec 6, 2024 ▶ 43:38 Zachary Bookman: Why Valuations and Fundraising are BS | E1235 · 20VC with Harry Stebbings
Insight
Bookman: M&A should drive product innovation rather than just revenue acquisition
“M&A can be innovation. It's not just buying for customers or revenue. We don't even do that. We buy for product quality and adjacency, and it jumpstarts the innovation.”
Zachary Bookman Dec 6, 2024 ▶ 18:03 Zachary Bookman: Why Valuations and Fundraising are BS | E1235 · 20VC with Harry Stebbings
Opinion
Bookman: Rippling executes acqui-hires whereas OpenGov acquires built products
“By the way, I think the guys at Rippling are doing something slightly similar. They're gathering founders, and they're, some of these have subject matter expertise, some don't, and it's a, they're acquihiring, and we're doing product acquisitions.”
Zachary Bookman Dec 6, 2024 ▶ 19:47 Zachary Bookman: Why Valuations and Fundraising are BS | E1235 · 20VC with Harry Stebbings
Insight
Bookman: Hire growth-mindset up-and-comers over playbook-driven executives
“I've changed my mind on up and comers. I spent a lot of time hiring, been there, done that. And I've grown a little tired of it. And I all, I see the value of promoting from within. I see the value of hiring people that are geniuses and want to work like all t…”
Zachary Bookman Dec 6, 2024 ▶ 1:01:51 Zachary Bookman: Why Valuations and Fundraising are BS | E1235 · 20VC with Harry Stebbings
Assertion Partly supported
Bookman: OpenGov was valued at $210M before its $1.8B acquisition
“A group in Tampa, the Weatherford capital. It was at two 10 pre-Harry just five years ago, and we just got marked, you know, in February at 1.8, so.”
Zachary Bookman Dec 6, 2024 ▶ 16:42 Zachary Bookman: Why Valuations and Fundraising are BS | E1235 · 20VC with Harry Stebbings
Insight
Lonsdale: For-Profit Startups Generate Greater Positive Impact Than Non-Profits
“OpenGov actually had more positive impact than the nonprofit ever could, because with OpenGov, you can get a bunch of best engineers, a bunch of the best business and salespeople, and you actually can get something that's self-sustaining to go to thousands of …”
Joe Lonsdale Mar 11, 2024 ▶ 49:03 Joe Lonsdale: The Future of TikTok; Is it a Danger to US National Security? | E1125 · 20VC with Harry Stebbings
Assertion Not publicly verifiable
Bookman: OpenGov ARR grew from $110M during deal talks to over $150M
“When we did the price negotiation, we were probably one 10, one 15, something like that. Very quickly, we've surpassed one 50.”
Zachary Bookman Dec 6, 2024 ▶ 41:40 Zachary Bookman: Why Valuations and Fundraising are BS | E1235 · 20VC with Harry Stebbings
Disclosure
Bookman: OpenGov ignores inbound sales leads from outside its core US ICP
“We literally, we get an inbound, if you gave me an inbound from the central office of the UK, we're not responding. We're not responding. Our sellers, they can't prospect outside the ICP segmentation.”
Zachary Bookman Dec 6, 2024 ▶ 28:45 Zachary Bookman: Why Valuations and Fundraising are BS | E1235 · 20VC with Harry Stebbings
Disclosure
Bookman: OpenGov maintains gross retention in the mid-to-high 90s
“I'll take ours in the mid to high nineties.”
Zachary Bookman Dec 6, 2024 ▶ 6:23 Zachary Bookman: Why Valuations and Fundraising are BS | E1235 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Bookman: OpenGov Took Five Years to Find Real Business Traction
“We were, we actually came out of the gate selling about a year in, but we were selling 5000 dollar software, 10,000 dollar software, transparency reporting. It was kind of a political sale. Governments would buy it to show off the data in their 3040 year old E…”
Zachary Bookman Dec 6, 2024 ▶ 1:37 Zachary Bookman: Why Valuations and Fundraising are BS | E1235 · 20VC with Harry Stebbings
Assertion Not publicly verifiable
Bookman: OpenGov generated $20M in revenue while burning heavily in 2019
“I was probably in the twenties, if I remember correctly, and I was burning cash like a drunken sailor.”
Zachary Bookman Dec 6, 2024 ▶ 16:56 Zachary Bookman: Why Valuations and Fundraising are BS | E1235 · 20VC with Harry Stebbings
What-if
Bookman: OpenGov Would Have Died in 2014 Without Unfair Advantages
“If we didn't have some of these unfair advantages, we would have been dead pretty early, like in 2014 or 15.”
Zachary Bookman Dec 6, 2024 ▶ 32:34 Zachary Bookman: Why Valuations and Fundraising are BS | E1235 · 20VC with Harry Stebbings
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