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.
why aren't all 88 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 3 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
Ehrenberg: Polymarket and Kalshi Are Pure Regulatory Arbitrage Plays
“This is the purest regulatory arbitrage play of all time. Okay. If you can look at the cumulative market cap of regulated sports betting and look at how it has dropped in response to the rise of Polymarket and Calci, who are not subject to the same rules and r…”
Ehrenberg: I Would Spend Almost No Time Investing in Pure AI
“I'm not in pure tech anymore, but if I was, I would literally be spending almost no time in pure AI.”
Ehrenberg: Andreessen Horowitz and Insight Partners Are Corporations, Not Venture Firms
“Yes, you're going to have more of the Andreessen's and the insights and these platforms that they're not really venture firms. They're Corporations that are multi-stage investment firms. That have some venture, that have some growth, that have some pre-IPO, an…”
Ehrenberg: Traditional LP structures are completely broken
“So LP structures, traditional LP structures are completely broken.”
Ehrenberg: Underperforming VC Firms Face a Slow-Motion Train Wreck
“I think there is a whole swath of the industry that is going, it's like a slow motion train wreck. They are not going to be able to raise new funds.”
Ehrenberg: Tiger Global and Coatue face horrific portfolio markdowns ahead
“You know, their mark to market now, the next couple of years is going to be horrific. They're going to see huge markdowns on a huge swath of their companies, a bunch of stuff that they had counted on to go public isn't going to go public.”
Ehrenberg: Broad VC platform services are useless at the seed stage
“And the bottom line is at the very early seed stage where you're just trying to prove out the experiments. None of this crap matters, right? Conversely, once you've proven the experiments and you've got a real company and you've got a company that is worthy, t…”
Ehrenberg: State Gaming Tax Hikes Drive Consumers to Offshore Markets
“And the more that, you know, Illinois jacks up rates, In state, A, those, the regulated sports, the sports books that are subject to these rates reduce investment in the state, handle those down, tax revenue goes down, and those customers that are now getting …”
Ehrenberg: Top VC Firms Will Maintain Premium Fees Due to Outperformance
“It's going to be just like hedge funds. You know, look at Sequoia. The best firms charge premium fees and will be able to get it because on an after fee basis, they still outperform.”
Ehrenberg: Very early stage artisanal venture capital will never be scalable
“That's the thing is very early artisanal VC is not scalable and it never will be. People have tried and they have failed.”
Ehrenberg: Inflow of sovereign and family office capital into VC is permanent
“If there's no going back because there are now these much larger firms that are institutionally investable that can take sovereign money and, you know, massive family office money in that trend, that wave is just going to continue.”
Ehrenberg: Late-Stage Venture Capital Will Face Hedge Fund-Style Fee Compression
“So what I would expect is a normalization that would look a lot like the hedge fund industry where smaller Longer dated, higher returns, differentiated managers will still command premium fees, and then more mature strategies, late-stage growth, pre-IPO, massi…”
Ehrenberg: Mid- and late-stage venture will face greatest disruption
“The greatest disruption in a way is going to be in the mid and late stage venture scene where managers are going to want to and need to gather enormous amounts of assets.”
Roger Ehrenberg: Continuation Funds Will Be the Primary VC Liquidity Source
“I think probably the greatest source of liquidity now is going to be continuation files, and it's going to be existing portfolios, raising money from net new investors, yet it reflects today's valuations, and you basically get fresh capital to join the partner…”
Ehrenberg: Continuation Funds Exploit Venture Capitalists' Desperation for LP Liquidity
“Because there has been so little liquidity for so long, some managers are desperate because they're under tremendous heat from their LPs. To get blood from a stone, right? And then you've got continuation fund managers that are deeply aware of the phenomenon I…”
Ehrenberg: Selling Trade Desk Early Was Undeniably The Right Decision
“Let me tell you, the downside regret versus the upside opportunity cost. Like, we made the right trade. It's not even a question.”
Ehrenberg: Sports Team Prices Will Keep Rising as Institutional Capital Enters
“No. Because of something we talked about earlier, which is with this tremendous influx of institutional capital and with pro teams, pretty soon the NFL, I would guess, becoming PE investable, return expectations are going to come down and prices are going to g…”
Ehrenberg: Peak market fear will cut seed valuation caps under $10M
“When the fear really hits, the really smart seed stage investors are going to go in hard. Because that's when you get the best opportunities. You get great founders, and you get great businesses at prices that are a half. Of what companies were getting, you kn…”
Ehrenberg: Series B startups growing under 100% will not get good terms
“If you're a series B company and you're not growing a hundred percent year on year, are new investors going to be throwing term sheets at you in this environment? I don't think so. Certainly not at the prices that those founders would want.”
Ehrenberg: Seed investors should almost never join pay-to-play rounds
“What the data shows is that, and this is a hard thing to stomach, it almost never makes sense to participate in a pay-to-play as a very early investor. Almost never.”
Ehrenberg: FTC regulatory scrutiny will block FAANG M&A acquisitions
“I'm not sure the FTC is going to let those deals happen. So that adds a curveball in M&A that we have not had easily in a generation, which is this very, very restrictive regulatory environment where a bunch of the logical buyers, the FAANGs, for instance, are…”
Ehrenberg: Tech PE will fill M&A void but pay lower valuations
“And maybe what that speaks to, Harry, is a further rise of firms like Vista and Insight. So you have tech PE start to step into the shoes of M&A. The issue there, though, is they don't pay as much. Somebody like Vista, you know, they have accumulated a bunch o…”
Ehrenberg: Concentrated seed portfolios best deliver 3x to 5x net returns
“What that really led me to believe when I looked at modeling portfolio construction around the time that I started IA was that a much more concentrated strategy than a more traditional strategy. 40, 50, 60 portfolio constituent approach was what I felt had the…”
Ehrenberg: IA Ventures limits portfolios to 25 companies per fund
“Our adaptation of that is, you know, we're a very small firm taking an artisanal approach to venture investing where, you know, Brad, Jesse, and I, we have no junior people. We each do our own work. That by going deep in two to three companies a year each over…”
Ehrenberg: Seed VC signaling risk is a red herring for Series A
“The notion of misalignment is somewhat of a red herring because smart investors will see what we're seeing and that if the company hasn't done well, Then they're not going to be able to raise anyway.”
Ehrenberg predicts the VC industry will consolidate into a barbell model
“I think it really is, is going to, that the industry is going to look like a barbell, and I've long thought you'll kind of have firms that are really focused on helping build companies at the seed stage and proving out their businesses, and then you'll have la…”
Ehrenberg predicts a major shakeout among growth-stage VC funds
“I mean, I think there's going to be a real shakeout because I think that there are relatively few growth funds that are going to be able to hit the return objectives to kind of justify LP investment.”
Ehrenberg: Complex term sheets and document obscurity in VC mean nothing
“I spent 12 of my 18 years in the derivatives markets, and I know that mystery and seeming obfuscation and complexity adds mystique. It's such bullshit. It's like the hardest part of VC is finding great people who are aligned on the challenging mission that's i…”
Ehrenberg: Big Tech Will Increasingly Buy AI Startup Assets and Talent
“Essentially it's an asset purchase. And I think that's something we'll continue to see more and more of”
Ehrenberg: Game Changers Will Concentrate 75% of Capital Into 3-5 Companies
“I'm following a similar playbook of three to five companies out of the 20 to 25 companies constituting 75% of the capital. Deployed.”
Ehrenberg: Game Changers Invested $1.5M at $10M Post-Money Valuation
“We just wrote a 1.5 check at a 10 post. So, 15% ownership in a really, really cool analytics company that, yeah, is disrupting a seriously stodgy and screwed up sector that I think is generalizability outside of that space.”
Ehrenberg: Early-Stage Venture Capital Will Never Be Commoditized
“Venture is never going to be commoditized. Maybe mid and late stage will feel more like institutional asset management, but I think incubation, pre-seed, and seed will always occupy a different place.”
Ehrenberg: Corporate venture LPs are cyclical and fair-weather investors
“So I think that corporates, I don't even need to make the argument. They are fair weather and they are cyclical. So as a generalization, there are obviously a few that are in it for the long haul, but it is very much a fruit of the day.”
Ehrenberg: Venture Capital Returns Below 10% Fail to Compensate for Illiquidity
“If you could get risk adjusted returns of. 12 to 15%, that's pretty freaking good. If it's below 10%, then you're not getting paid for the risk. Right, so there's, it's what is the premium that you're willing to accept Above liquid strategies over long periods…”
Ehrenberg: Venture Capital Requires a 500-700 Basis Point Illiquidity Premium
“If you're getting paid 500 to 700 basis points for illiquidity, and you're a, either a perpetual institution by charter or just so massive that you effectively act like that, then Yes, that occupies a perfectly fine place in your portfolio.”
Ehrenberg: Clubhouse Was Light Years Away From Public Market IPO Readiness
“And let's just pick on Clubhouse since you raised it. If you had taken a deep breath, looked at an offer, said, huh, from an IPO readiness perspective, where is this company? The objective answer to that question is no fucking where light years away.”
Ehrenberg: Secondaries Are Now the Only Way to Recycle Capital
“Really, the only way to get that recycling now is through secondary.”
Ehrenberg: IA Ventures Turned $5.2M in The Trade Desk into $300M DPI
“I think that we ended up returning five to six X net on that one trade. It was a two hundred and fifty million dollar fund. So 5000005.2 million turned into net two 50 to three hundred million DPI.”
Ehrenberg: Holding The Trade Desk Longer Would Have Added 5x-10x Fund Return
“We could have held onto TTD and returned another five to 10 X of the fund.”
Ehrenberg: Sports franchises are poorly managed with room for improvement
“They are not managed as well as you would think. There's a lot of room for improvement.”
Ehrenberg: A Trump presidency would ease FTC antitrust policy and unlock M&A
“Yes, certainly with a different head of the FTC, it's, I mean, the pendulum has swung all the way in the other direction. I think you could argue that antitrust was extremely weak for a generation, and now it's swung all the way in the other direction, so I wo…”
Roger Ehrenberg: Fund managers raising capital must be shocking and ignore playbooks
“Be different. Take risk. Don't play it safe. Have a deeply held thesis and just put it out there. Be shocking. Don't be a sheep. Don't follow the playbook.”
Ehrenberg: The best founders use VCs for psychological support, not dependence
“I think the best founders aren't dependent. I think the best founders benefit from really good VCs to act as a sounding board, especially in those earliest days and to give them honestly, empathy and psychological support, because that is often the hardest thi…”
Ehrenberg: VCs Are Value-Destructive Unless Humble About Their Limitations
“I don't know about the percentage, Harry, but I do think that there is something to the general view that VCs think a lot of themselves and probably attribute more skill than they act to themselves than they actually have. I think unless a VC is, is proactivel…”
Ehrenberg: 2022 market downturn resembles 2001 dot-com crash, not sudden shock
“The difference between this and say, 87 and 97 with LTCM is that, you know, this is not a shock. This is not an episodic jolt. This is much more akin to a one when you had valuations getting stretched to the point of just lacking reason.”
IA Ventures funded The Trade Desk when outside investors refused
“Yet, you know, the insiders were confident that Jeff Green, Dave Pickles, and the team were on the right track, and that they were doing something truly differentiated, and they were executing well. It just was in an unsexy area at a really bad time, and we co…”
IA Ventures invested over 10% of its $50M fund into The Trade Desk
“So we co-led seed, and then it leads into two small bridges. So when the dust settled, we ended up having 2.2 million out of a fifty million dollar fund in the company. So that was still, you know, under It wasn't until after they had taken off like a rocket s…”