The Ledger, every show

Every statement that passed quotation and attribution checks, across all 44 shows. Pick shows below, then mix any filter with any other.

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THE PITCH Opinion
Diamond: Hershberg's 20% equity versus PE's 80% is egregious
“You only own 20% of the company. Meanwhile, the original partners of the brewery own 80% of the company. It's our opinion that, like, fundamentally those numbers are a bit egregious, and we think, like, they literally should be swapped.”
Howie Diamond Mar 4, 2025 ▶ 27:29 #119 Amateur Golf Society: Venture Capital vs. Private Equity
THE PITCH Prediction Not checkable as stated
Howie Diamond: Teamable could be a $500M to $1B exit
“Like, I do think it's overvalued, but I do think that this could be one of those opportunities where it's like a half a billion to a billion dollar exit, if not more, based on your hustle, based on, you know, all the things that you've said, based on your attr…”
Howie Diamond Mar 3, 2025 ▶ 17:39 #12 "I Don't Need Your Money" Teamable
THE PITCH Disclosure
Diamond: Alpha Bridge is earmarking $1M for founder wellness platform
“So we're earmarking a million dollars from the fund we justify because we feel like we're gonna get into the best deals based on this program.”
Howie Diamond Mar 3, 2025 ▶ 7:37 #100 When Investors Take the Hot Seat
THE PITCH Prediction Not checkable as stated
Howie Diamond: Outlines won't achieve mainstream adoption due to high prices
“I don't see the mainstream adoption for this product because the price is way too high and way too premium for me to To get involved in this because I just think it's going to be a very, very small select people who care about the environmental impacts to get …”
Howie Diamond Mar 4, 2025 ▶ 10:13 #123 Outlines: A Venture-Backed Shower Curtain?
THE PITCH Prediction Didn’t hold up
Howie Diamond: Ride iQ will take our money in 18 months
“They'll take our money in a year and a half from now. ... They will. Trust me.”
Howie Diamond Mar 4, 2025 ▶ 16:37 #121 Ride iQ: Peloton for Horses
THE PITCH 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
THE PITCH Opinion
Diamond: Blockchain is a paradigm shift comparable to mobile and cloud
“But I think the blockchain is a paradigm shift. I mean, there is the mobile computing paradigm shift. There was the cloud computing paradigm shift. I think the blockchain is a new paradigm shift.”
Howie Diamond Mar 3, 2025 ▶ 22:04 #50 Ticket Scalpers, Beware! Blockchain Is Coming for You.
THE PITCH Prediction Not checkable as stated
Diamond: Atomos Will Either Go to Zero or Reach $20 Billion
“This is a company that will go to zero or it'll be a 20, twenty billion dollar company.”
Howie Diamond Mar 3, 2025 ▶ 22:17 #48 Will This Space Startup Make It off the Ground?
THE PITCH Opinion
Diamond: Playven cannot successfully do both SaaS and a marketplace
“You're doing two things, and I don't think you can do both.”
Howie Diamond Mar 3, 2025 ▶ 16:02 #44 Is This Sports App the Next OpenTable?
THE PITCH Opinion
Diamond: Valuation cap differences between $10M and $15M do not matter
“At the end of the day, it's actually not going to matter in terms of whether it's 1011, 12, or 15. It's actually not going to matter.”
Howie Diamond Mar 3, 2025 ▶ 21:45 #12 "I Don't Need Your Money" Teamable
THE PITCH 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
THE PITCH Insight
Diamond: Customer LOIs are meaningless without signed contracts
“Like, to me, LOIs are, I mean, those are, that's bullshit.”
Howie Diamond Mar 3, 2025 ▶ 26:27 #8 FightCamp (formerly Hykso)
THE PITCH Insight
Diamond: Bridge Rounds Include High-Performing Outliers, Not Just Distressed Startups
“There was a negative stigma attached to the term bridge, and now people are calling it post seed, seed extension, whatever. C two. There are companies that are in these bridge rounds that are distressed companies that are looking for an influx of capital to he…”
Howie Diamond Mar 3, 2025 ▶ 4:03 #100 When Investors Take the Hot Seat
THE PITCH Assertion Not checkable as stated
Diamond: Our Post-Seed Cohort Delivered 2X to 2.5X Markups in 12 Months
“And we started seeing this crazy performance From this particular cohort of companies that we were investing in, anywhere from like, two X to 2.5 X over the course of 12 months from when we invested to Series A.”
Howie Diamond Mar 3, 2025 ▶ 4:25 #100 When Investors Take the Hot Seat
THE PITCH Disclosure
Diamond: Alpha Bridge will not invest in seed rounds
“We start building the relationship in the seed. We won't invest, but we'll start building rapport with the founder.”
Howie Diamond Mar 3, 2025 ▶ 8:18 #100 When Investors Take the Hot Seat
THE PITCH Prediction Open · timeframe Mar 2035
Diamond: In 5 to 10 years everyone will own in-home VR
“Just like you have a video game console, you have a at home entertainment console, everyone's going to have a VR in their homes, a VR headset. But I think we're a ways away from that. You know, I think we're like five or 10 years away from that, lowering that …”
Howie Diamond Mar 3, 2025 ▶ 18:33 #4 Skylights
THE PITCH Opinion
Diamond: iMirror Features Can Easily Be Done on an iPad
“Everything you described can happen on an iPad, but you're focused, you're saying that it should happen in a, on a mirror, on a wall. Yeah. That's not convincing to me.”
Howie Diamond Mar 3, 2025 ▶ 11:28 #2 iMirror
THE PITCH Opinion
Diamond: Outlines won't reach mainstream adoption due to its premium pricing
“I don't see the mainstream adoption for this product because the price is way too high and way too premium for me to get involved in this because I just think it's going to be a very, very small select people who care about the environmental impacts to get ove…”
Howie Diamond Nov 1, 2023 ▶ 10:03 "VCs Debate: Is This Recyclable Shower Curtain the Future of Circular Economy Home Products?"
THE PITCH Prediction Didn’t hold up
Howie Diamond predicts Ride IQ will take his money in 18 months
“They'll take our money in a year and a half from now.”
Howie Diamond Oct 18, 2023 ▶ 16:35 1. "This Startup Pitch for Equestrian Tech Just Changed the Game for Horse Training Technology!"
THE PITCH Opinion
Howie Diamond argues Ride IQ warrants a $6M valuation due to slow growth
“Their margins are great, their growth is not. So like six, between six and seven makes sense.”
Howie Diamond Oct 18, 2023 ▶ 18:45 1. "This Startup Pitch for Equestrian Tech Just Changed the Game for Horse Training Technology!"
THE PITCH Insight
Diamond: High Engagement Rivals Pinterest Even Without Direct Purchase Conversion
“I don't even care so much about the conversion into an actual purchase, but if, like Pinterest, there's people who go on there every day four times a day and never purchase anything, but that engagement is really powerful.”
Howie Diamond Mar 4, 2025 ▶ 8:35 #125 Locker: The Future of Online Shopping
THE PITCH Opinion
Diamond: Raising $3M at $10M to $15M Valuation Will Be Tough
“I think it's going to be difficult to raise three million dollars. I mean, not impossible. I mean, I've seen crazier things happen, but in this market environment, based on where you are raising three on a 10 or 15 is going to be tough.”
Howie Diamond Mar 4, 2025 ▶ 12:07 #125 Locker: The Future of Online Shopping
THE PITCH 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
THE PITCH Opinion
Diamond: Boxing as a sport has hit a low point
“Boxing actually, as a sport, has also hit a low.”
Howie Diamond Mar 3, 2025 ▶ 13:45 FightCamp: A Name Change, A Game Change
THE PITCH Disclosure
Diamond: Passes on Hykso over narrow total addressable market concerns
“To me, I worry about, like, the, like the total addressable market, like the TAM. I think for me, it's a little too narrow, so I'm gonna pass.”
Howie Diamond Mar 3, 2025 ▶ 17:28 FightCamp: A Name Change, A Game Change
THE PITCH Disclosure
Diamond argues valuation caps do not matter when investor conviction is high
“Whether it's six million, whether you're raising at a five million cap or a six million cap or a ten million dollar cap right now, if I have that conviction, I'm not too concerned.”
Howie Diamond Mar 3, 2025 ▶ 20:15 #51 This Bot Can Fight Your ATM Fees
THE PITCH Disclosure
Diamond prefers to wait 12 months and pay double for proven data
“And so I can sit back and wait eight to 12 months, see how this develops, see the new implementations. See how the customers are responding. Really get some accurate data here and see what the real numbers are. And then I'll pay more. I'll pay double.”
Howie Diamond Mar 3, 2025 ▶ 20:37 #51 This Bot Can Fight Your ATM Fees
THE PITCH Assertion Partly supported
Diamond: Fluffy Pony's rival blockchain ticketing startup closed a $10M round
“He partnered with some, he partnered with the ex-CEO of, I believe, Ticketfly, and he also partnered with the ex a good friend of mine who started Redbox Tickets, and the three of them got together and are doing the exact same thing and just closed, like, a te…”
Howie Diamond Mar 3, 2025 ▶ 11:17 #50 Ticket Scalpers, Beware! Blockchain Is Coming for You.
THE PITCH Opinion
Diamond: Bandwagon's rival blockchain startup is one to two years ahead
“They're very well funded, and I feel like they're a year or two ahead of you, and I didn't get into their last round because I was staying away from blockchain.”
Howie Diamond Mar 3, 2025 ▶ 15:45 #50 Ticket Scalpers, Beware! Blockchain Is Coming for You.
THE PITCH Prediction Didn’t hold up
Diamond: Hughes will easily raise his $1.5M round for Bandwagon
“I think he'll raise this round, no problem. He's great. He'll get to 1.5, and then we'll see where it goes.”
Howie Diamond Mar 3, 2025 ▶ 21:59 #50 Ticket Scalpers, Beware! Blockchain Is Coming for You.
THE PITCH Opinion
Diamond: The space market is $500 billion, not $350 billion
“And they're understating the market. I don't think it's three hundred fifty billion dollar market. I think it's a half a trillion dollar market.”
Howie Diamond Mar 3, 2025 ▶ 22:21 #48 Will This Space Startup Make It off the Ground?
THE PITCH Opinion
Diamond: AR and VR are on the hype cycle's upward slope
“And I think ARVR is, is on the upward slope of enlightenment right now.”
Howie Diamond Mar 3, 2025 ▶ 23:32 #45 Whatever Happened to Virtual Reality?
THE PITCH Opinion
Diamond: Unsound unit economics is a pervasive problem across meal delivery startups
“And this is something, by the way, that every food delivery and meal delivery subscription or on demand or whatever company deals with, right? This is like a pervasive problem In this space.”
Howie Diamond Mar 3, 2025 ▶ 18:40 #9 Tuckrbox
THE PITCH Disclosure
Diamond: Passing on Hykso due to narrow total addressable market
“To me, I worry about, like, the, like the total addressable market, like the TAM. I think for me, it's a little too narrow, so I'm gonna pass.”
Howie Diamond Mar 3, 2025 ▶ 17:01 #8 FightCamp (formerly Hykso)
THE PITCH Insight
Diamond: Casino players hate winning jackpots because it breaks their flow
“When you're in the zone as a player, and you, when you win money, when you actually win a jackpot or you win, they are upset because it takes them out of the zone. It's not actually about winning or losing. It's just about a departure from their life.”
Howie Diamond Mar 3, 2025 ▶ 22:51 #6 Guru Games
THE PITCH Assertion Not checkable as stated
Diamond: FitGuard lacks a working prototype after three and a half years
“It's been three and a half years, and you don't, you still don't have a working prototype.”
Howie Diamond Mar 3, 2025 ▶ 24:38 #5 FITGuard
THE PITCH Prediction Not checkable as stated
Diamond: Locker will struggle raising $3M at $10M-$15M valuation
“I think it's going to be difficult to raise three million dollars. I mean, not impossible. I mean, I've seen crazier things happen, but in this market environment, based on where you are raising three on a 10 or 15 is going to be tough.”
Howie Diamond Nov 16, 2023 ▶ 11:58 $3M on the Line! Can AI-Powered Shopping Assistant Disrupt E-Commerce with Social Shopping Startup?
THE PITCH 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?
THE PITCH Opinion
Diamond: Amateur Golf Society could reach $100M enterprise value at $30M revenue
“Typically, if someone says they're looking to build something really quickly and flip it, I would be out. But at a three million dollar price point, and with what you need to achieve to get to that thirty million dollar revenue mark, which I think could transl…”
Howie Diamond Sep 20, 2023 ▶ 18:05 "Startup Funding Secrets: Will This Golf Tech Pitch Convince VCs to Invest?"
THE PITCH Assertion Not checkable as stated
Diamond: Board majority can remove founder Dan Hershberg at any time
“They can vote you out tomorrow.”
Howie Diamond Sep 20, 2023 ▶ 21:56 "Startup Funding Secrets: Will This Golf Tech Pitch Convince VCs to Invest?"
THE PITCH Disclosure
Howie Diamond commits $30,000 to Babyscripts
“I'm even smaller than Jake, so I write 25 to 50 K checks, but I think that those are the types of projects that I like to put myself into, that I like to participate in, you know, not only as an investor, but also as a partner to sort of help, because that's w…”
Howie Diamond Mar 3, 2025 ▶ 21:28 #1 Babyscripts
THE PITCH Disclosure
Diamond: Invested in personal finance management app Albert
“I'm in a company called Albert. That's a personal financial mention. And yeah, they're great.”
Howie Diamond Mar 3, 2025 ▶ 11:06 #51 This Bot Can Fight Your ATM Fees
THE PITCH 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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