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 24 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
Soininen: Playven could have raised its bridge round at $8M
“We could have, ah, gone to them at eight and we probably should have, ah, we like.”
Topias Soininen Mar 3, 2025 ▶ 12:48 #44 Is This Sports App the Next OpenTable?
What-if
Bill Smith: Shipt and Landing would have failed if launched two years later
“The timing of everything that I created, if you just rolled it forward two years, it wouldn't have worked. In, InSight wouldn't have worked. Shipt would have missed, completely missed the window. Even landing, we would have missed the window because there's ju…”
Bill Smith May 8, 2024 ▶ 40:02 Startup Funding Competition: Can This Founder Raising Venture Capital Secure a $550M Exit.
What-if
Qleek founder claims they would have raised heavily during NFT boom
“Like, if we would have survived COVID, or if COVID didn't happen, the NFT thing would have happened, and then we would have raised so much money.”
Ismail Salhi Mar 4, 2025 ▶ 11:15 #108 Qleek Pt. III: A Postmortem and a Comeback
What-if
Diamond: Sudden Coffee should have used crowdfunding to avoid massive dilution
“I mean, you could have probably launched a crowdfunding campaign, come back around and raise money at a much higher valuation, but you know, you're, cause like right now you're deluding yourself by like, you're giving up like half the company.”
Howie Diamond Mar 3, 2025 ▶ 15:29 After the Pitch: Sudden Coffee
What-if
Diamond: Sudden Coffee surrendered too much equity instead of crowdfunding
“I mean, you could have probably launched a crowdfunding campaign, come back around and raise money at a much higher valuation, but you know, you're, cause like right now you're deluding yourself by like, you're giving up like half the company.”
Howie Diamond Mar 3, 2025 ▶ 18:24 #10 Sudden Coffee
What-if
Wiseman: Would have passed on KAV Sports without workplace safety vertical
“I also thought, I mean, if he hadn't talked about the workplace safety element, like I would have been an out for sure, just not a big enough market.”
Will Wiseman Mar 26, 2025 ▶ 28:01 Will VCs Bet $3M on This Custom Helmet Startup?
What-if
Diamond Would Have Invested If Locker Raised $1M at $6M-$7M Cap
“If she came in and was like, I'm raising a million on six or seven million cap, and we are going to get to half a million users, and here's how we're going to do it, and she had that conviction, I would be more inclined.”
Howie Diamond Mar 4, 2025 ▶ 17:11 #125 Locker: The Future of Online Shopping
What-if
Bobbi Racette says Hyatt's complex terms required a $250,000 investment, not $25,000
“And to be honest, like, if he was coming in at 200 or 250 or something like that, then I would obviously have, I would have totally educated and thought, okay, you know what, like, this is probably good. Because he's coming in as, you know, a higher investor, …”
Bobbi Racette Mar 3, 2025 ▶ 25:32 #82 A Deal Too Perfect to Pass Up
What-if
Jillian Manus would have invested in Tot Squad at lower valuation
“If she had come in, I think we probably would, well, I would have been in, I would have been in, but I think she did not understand, and I'm trying to understand who advised her.”
Jillian Manus Mar 3, 2025 ▶ 18:27 #71 Raising Kids Is Hard. So Is Raising a Startup.
What-if
Nadel: I would have passed if I knew ad revenue lacked traction
“If I had, during the pitch, if I had fully understood, if we had talked about and I understood that, you know, the advertising piece of it representing 60% of revenue had no traction yet, or none to speak of, then I would have either passed or pushed back on t…”
Phil Nadel Mar 3, 2025 ▶ 25:43 #58 Park Your Pooch Here
What-if
Kassam: Giving up 10% equity is costlier than O'Leary's royalty deal
“Giving away, you know, Robert's deal, if I had given away 10% of Monty Kidd's would have been So much more expensive than the royalties that Kevin is asking for. I mean, you know, 10% of Monty kids in several years out is going to be so much more valuable than…”
Zahra Kassam Mar 3, 2025 ▶ 36:00 #56 Shark Tank vs. The Pitch
What-if
Kesserwani: Cushion's existing waitlist represents $1M in potential revenue
“Just our waitlist today, if we were to monetize this, represents a million dollars in revenue. If you were just to, like, scale this out.”
Paul Kesserwani Mar 3, 2025 ▶ 17:31 #51 This Bot Can Fight Your ATM Fees
What-if
Nadel: A brick-and-mortar retail plan would have triggered an immediate pass
“If he said he wanted to go brick and mortar retail, I'd be like, no way.”
Phil Nadel Mar 3, 2025 ▶ 21:30 #49 Nuts Can Kill. Are Seeds the Answer?
What-if
Manus would invest in Playven at a $4M to $4.5M valuation
“If this was at four million, I would definitely come into this, or 4.5.”
Jillian Manus Mar 3, 2025 ▶ 20:14 #44 Is This Sports App the Next OpenTable?
What-if
Phil Nadel: I would not have invested without key hire Eric
“And I'll tell you, I would not have said yes if he hadn't hired Eric already.”
Phil Nadel Mar 3, 2025 ▶ 22:08 #25 Rex
What-if
Manus: All investors would have backed Lunar Wireless at lower valuation
“If you had stayed at 14 or whatever it was we all actually would have gone in.”
Jillian Manus Mar 3, 2025 ▶ 22:48 #22 Investor FOMO: Lunar Wireless
What-if
Howie Diamond Would Consider Locker at $1M on $6M to $7M Cap
“If she came in and was like, I'm raising a million on six or seven million cap, and we are going to get to half a million users, and here's how we're going to do it, and she had that conviction, I would be more inclined.”
Howie Diamond Nov 16, 2023 ▶ 17:02 $3M on the Line! Can AI-Powered Shopping Assistant Disrupt E-Commerce with Social Shopping Startup?
What-if
Hudson: Gemist is worth $100K at a $10M post-money valuation
“Clean 10 posts with, like, good founder ownership, I would have put in a hundred K.”
Charles Hudson Aug 23, 2023 ▶ 20:45 "Jewelry Industry Digital Transformation Needed: Can Shopify Jewelry Save the Day?"
What-if
Charles Hudson would have invested $100K at a $10M post-money valuation
“Clean 10 post with, like, good founder ownership, I would have put in a hundred K.”
Charles Hudson Mar 4, 2025 ▶ 20:45 #115 Gemist: The Crown Jewel of Venture
What-if
Charles Hudson passes on Fleeting due to navigation startup portfolio conflict
“So I have an investment in a trucking navigation company that I'm sitting here listening. I'm like, it's either very complimentary or like very competitive. And I can't sort that out. And I really liked your answer on autonomous. And if I did not have a confli…”
Charles Hudson Mar 3, 2025 ▶ 11:09 #89 A Big Bet on an Ex-Trucker
What-if
Nadel: Would not have invested in Rex without key executive hire
“And I'll tell you, I would not have said yes if he hadn't hired Eric already.”
Phil Nadel Mar 3, 2025 ▶ 19:13 I’ve Looked Death in the Eye
What-if
Zloof: Sudden Coffee Should Have Hired Chemical Engineer Two Years Earlier
“You know, I think we should have you know, two years earlier, like, hired a chemical engineer and started researching this from the beginning, but we were trying to sort of play it safe and iterate a little bit more”
Joshua Zloof Mar 3, 2025 ▶ 27:52 After the Pitch: Sudden Coffee
What-if
Schwartz: Collapsed acquisition would have more than doubled investor money
“They would have more than double. Yeah.”
Alon Schwartz Mar 3, 2025 ▶ 21:53 #93 David vs. Godzilla
What-if
Diamond: Would have passed on Snapchat 5 to 7 years ago
“If, when I was getting, if I were to get pitched, if Snapchat pitched to me, you know, five, seven years ago, I would have passed, because I didn't get it, and I'd be kicking myself for passing, right?”
Howie Diamond Mar 3, 2025 ▶ 16:25 #45 Whatever Happened to Virtual Reality?
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