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 26 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

What-if
Lavingia: Tesla and AngelList would have failed if founders could not code
“Like in the instance that Elon didn't know how to code, Tesla would have died. You know, in the instance of Naval knowing, not knowing how to code, AngelList would have died.”
Sahil Lavingia Jan 13, 2023 ▶ 1:09:36 Sahil Lavingia Gets Radically Honest
What-if
Andy Dunn: Would not raise venture capital if building Bonobos again
“No, I w I wouldn't have done it. If I could go back, I think there's so many Problems with raising money.”
Andy Dunn Sep 8, 2022 ▶ 30:00 Investing in Mental Health & Embracing Vulnerability with Andy Dunn
What-if
Howard Lindzon: Robinhood wouldn't exist if Vanguard hadn't hoarded its technology
“There should be no Robin Hood. There should be no any of this stuff. It should all still be CNBC and Vanguard and Goldman Sachs. They just didn't give their technology. They hoarded the technology.”
Howard Lindzon Nov 11, 2021 ▶ 44:04 Disruptive Innovation & Unbundling The S&P 500 With Howard Lindzon | Where It Happens
What-if
Isenberg: AI video editing saves hundreds of thousands of dollars
“This is something that would have cost hundreds of thousands of dollars to make, and using Fable with, ah, to video edit is totally possible.”
Greg Isenberg Jun 11, 2026 ▶ 2:58 Claude Fable 5 is BACK
What-if
If founded today, Duolingo would be a conversational AI tutor
“I think if Duolingo were to start today, it might look something more like this.”
Greg Isenberg Dec 3, 2025 ▶ 21:28 10 Unknown Apps Making $50K+ MRR (Copy Them)
What-if
Greg Isenberg: AI reduces plugin development costs from $500K down to $5K
“That I would have never been able to build two years, three years ago, because it probably would have cost me 500 K million dollars, and I wouldn't know if people actually would use the product because it's like a nicer version of something that's popular and …”
Greg Isenberg Jun 13, 2025 ▶ 25:51 How I Use AI & Reddit to Find $1M+ Startup Ideas (FULL Blueprint)
What-if
Isenberg: An acquirer could have crowdfunded $50M on Twitter to buy Mint
“If you were able to say, I got mint for twenty five million dollars or fifty million dollars and you went to Twitter, like in other places, like you probably could have raised that money to buy it.”
Greg Isenberg Jan 11, 2024 ▶ 27:28 $1M Startup Trends For 2024, With Michael Karnjanaprakorn
What-if
Torenberg: David Perell should have taken equity instead of selling courses
“He could have, instead of teaching people how to write, he could have gone to people who either, you know, are big on other platforms or just have really valuable service businesses like you know, financial wealth managers or accountants or lawyers or whatever…”
Erik Torenberg Jan 5, 2024 ▶ 29:58 How To Build A Million-Dollar Media Empire | Erik Torenberg
What-if
Huber: Without his Twitter audience, his net worth would be 90% lower
“If I didn't have Twitter, we would probably own about 10 self-storage facilities right now instead of 61. My net worth would be about 10% of what it is right now.”
Nick Huber Dec 22, 2022 ▶ 40:58 How Nick Huber Built His Wealth: From Sweaty Startup to Real Estate Investor
What-if
Wilkinson: Moving to San Francisco would have prevented building a profitable business
“I don't think I'd have a profitable at scale business today if I had moved to San Francisco.”
Andrew Wilkinson May 19, 2022 ▶ 24:18 Why You Need A Digital Detox with Andrew Wilkinson
What-if
Schneider: AI and Ephemeral Postgres Cut Data Cleaning From Hours to Minutes
“What have used it would have taken me probably five hours historically to like clean the data appropriately. And I smashed that out in like probably 20 to 30 minutes.”
Cody Schneider Mar 2, 2026 ▶ 40:13 Claude Code & MCPs built my $145K marketing machine
What-if
Isenberg: My First Million Succeeded Because of The Hustle Partnership
“My first million wouldn't be where it is today, in my opinion, if it wasn't for its partnership with the hustle.”
Greg Isenberg Jan 5, 2024 ▶ 12:38 How To Build A Million-Dollar Media Empire | Erik Torenberg
What-if
Isenberg: Late Checkout lost $3M+ in 2023 revenue by staying lean
“We basically had full utilization of our team the entire year, and we lost at least three million dollars of revenue. If we just would have not listened to this advice, we would have had three plus more million dollars in the bank.”
Greg Isenberg Dec 28, 2023 ▶ 6:15 My Biggest WINS & REGRETS Of 2023
What-if
Self-publishing 'The Art and Business of Online Writing' out-earned traditional deals
“Even if it's self published, art and business of online writing, self published. It's made me way more money than if I would have gotten a publishing deal for it. And everyone in the online writing world references it.”
Nicolas Cole Aug 3, 2023 ▶ 53:18 Status Games, Fame, and the Truth about FIRE
What-if
Sharma: Any pioneer mattress brand would have struggled like Casper did
“If Casper didn't exist, like whoever the next company was that did it, They would have had the hardest time and, you know, ended up in the same position.”
Nik Sharma Apr 20, 2023 ▶ 10:53 The Secret Strategies of Top DTC Brands with Nik Sharma
What-if
Josh Dorkin says BiggerPockets would have succeeded without his 100-hour weeks
“I would have been fine if I had worked a little less hard, to be honest, but you do have to put the time in.”
Josh Dorkin Mar 3, 2023 ▶ 1:02:45 From Zero to 2M+: How Josh Dorkin Built the Bigger Pockets Community
What-if
Lavingia: Gumroad would have failed if he could not write code
“So if I didn't know how to code, you wouldn't be listening to this today. Gumber would be dead.”
Sahil Lavingia Jan 13, 2023 ▶ 1:09:18 Sahil Lavingia Gets Radically Honest
What-if
Isenberg: Late Checkout rejected a Twitter buyout, dodging Elon Musk's layoffs
“Twitter, Twitter offered to buy us in, in, in, and, you know, we thought about it in, and I'm happy we didn't because we probably would have gotten fired by Elon cause he fired a lot of people.”
Greg Isenberg Jan 5, 2023 ▶ 6:44 Reflecting on a crazy 2022
What-if
Pal: Holding initial $200 Bitcoin beat his massive 2020 re-entry by 5x
“I went back and looked at if I'd just kept my initial investment at 200 bucks, I would have done, I can't remember them, five times better. Even though the size that I added in March, 2020 was massively larger than the first size.”
Raoul Pal Aug 18, 2022 ▶ 22:03 Investor Psychology & Trading on the Future With Raoul Pal
What-if
Saltarelli: Manufacturing plant returns fail under a five-year horizon
“Do you think that we would have ever built a manufacturing plant if we had a five-year business plan? Absolutely not. You could not make the returns work.”
Nick Saltarelli (Nick Salto) Jun 23, 2022 ▶ 43:02 How to Build a Brand of the Future
What-if
Isenberg: Tai Lopez NFT would succeed better with 300 mints
“If I was Tai Lopez, I wouldn't have created such a big collection. I think it's like 8600 or something like that. And I would have just focused on like 300. People like his odds of success would have been way higher higher if he just would have taken the club …”
Greg Isenberg Mar 24, 2022 ▶ 25:15 How to Engineer Serendipity | Matt Mullenweg, Automattic
What-if
Nikita Bier: TBH Would Have Failed If Launched on First Try
“If we just struck it on the first try, I think it would have crashed and burned really quickly.”
Nikita Bier Feb 15, 2022 ▶ 8:25 Will Meta Bounce Back? (with Nikita Bier) | Where It Happens | Bonus Episode
What-if
Ohno: NBC should have hired creators over investing in Snapchat
“And I thought it was like, well, why would they just give the money to a public company versus going directly to the creators themselves? The top, top 50 creators in the world, right? Speak different languages and saying, we're going to give you all access rig…”
Apolo Ohno Dec 10, 2021 ▶ 29:44 Buying the X Games with Olympic Icon Apolo Ohno | Where It Happens
What-if
Rogenmoser: Jasper wouldn't exist without spotting GPT-3 demos on Twitter
“If I hadn't been on Twitter six months before we launched Jasper, I wouldn't have seen GPT three come out. I wouldn't have seen some of the cool demos and I wouldn't have thought, well, I think we could do that for marketing content.”
Dave Rogenmoser Mar 30, 2023 ▶ 4:09 Master the Art of AI-first Products with Dave Rogenmoser's Winning Formula
What-if
Greg Isenberg: Uber would have failed starting as UberX in Europe
“I feel like if Uber would have started in, you know, in Paris or London as UberX. It wouldn't have worked.”
Greg Isenberg Dec 3, 2021 ▶ 22:12 Reinventing Home Ownership and Concierge Businesses With Sam Parr | Where It Happens
What-if
Diego Perez: I should have prioritized building a newsletter in 2016
“And I think, looking back, I feel like if I would have done things differently, I would have definitely put a lot more emphasis on building a newsletter in like starting in 2016, as opposed to starting in 2020.”
Diego Perez (Yung Pueblo) Oct 5, 2023 ▶ 11:02 How To Build An Audience From Scratch | Yung Pueblo
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