Mar 5, 2025 · 27m · tbpn
Packy McCormick Breaks Down Ramp's New $13B Valuation and Where He's Investing Right Now.
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Investor and Not Boring author Packy McCormick joins hosts Jordi Hays and John Coogan to discuss Ramp's valuation trajectory, the operational leverage enabled by AI software, and modern venture capital strategies across deep tech, media, and crypto.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. The hosts hold 51.6% of the talking time here. How this is scored →
The hosts as informed peer 5.1 Guest teaching 3.4 Guest disagreement 1.7 The hosts pushing back 1.7
speaking balance: gold is the hosts, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 18:24 Packy dismisses Substack bundling viability
Packy firmly dismisses the popular proposal that Substack should bundle top creators into a single subscription, arguing creator egos and bespoke sponsor dynamics make it unworkable.
Hardest push from the hosts ▶ 18:00 Coogan presses on Substack aggregation modelCoogan directly challenges Packy by asking why Substack should not aggregate creators into a single $20/month bundle rather than letting individual writers monetize externally.
Biggest teaching moment ▶ 18:24 Packy explains why creator ad networks failPacky educates the hosts on creator economics, explaining why top brands partner with bespoke creators rather than programmatic ad networks.
The host holds their own ▶ 2:39 Coogan breaks down down-round mechanicsCoogan displays deep startup finance knowledge by dissecting cram downs, pay-to-play provisions, and founding equity wiped out in 2023 tech down rounds.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | The hosts as informed peer | Guest teaching | Guest disagreement | The hosts pushing back | Why |
|---|---|---|---|---|---|---|
| Ramp's Valuation Trajectory and Tech Down Rounds | 6 | 3 | 1 | 1 | Coogan demonstrates detailed market expertise by detailing the brutal mechanics of 2023 tech down rounds, including pay-to-play terms, cram downs, and founder dilution. Packy provides historical valuation context for Ramp's early funding rounds. | |
| The Ramp Safety Dilemma and Financial Automation | 3 | 1 | 1 | 1 | The exchange is lighthearted and collaborative as the hosts riff on 'Ramp safety' and AGI parallels. Packy joins the bit with jokes about running out of atoms in the universe and personal anecdotes about his father. | |
| Macro Investment Outlook and Humanoid Robotics Froth | 5 | 4 | 2 | 2 | Hays introduces market top indicators and checks BMW's market cap against humanoid robotics valuations. Packy provides a reasoned investment framework analyzing the $45T human wage TAM against the severe competitive risks in hardware robotics. | |
| Lean Startup Leverage and Challenging Incumbents | 5 | 3 | 2 | 1 | Hays highlights Packy's thesis on lean software leverage citing Cursor's ARR efficiency. Packy expands on this, highlighting that smaller teams can now attack massive entrenched incumbents like K-12 education rather than just building lean apps. | |
| AI Writing Tools and Common Model Artifacts | 6 | 3 | 1 | 2 | Packy critiques common LLM quirks such as repetitive em-dash usage and the overuse of 'delve'. Coogan demonstrates technical domain knowledge by proposing an explanation rooted in Kenyan RLHF training datasets and hashtag artifacts. | |
| Substack Media Models and Platform Bundling | 5 | 5 | 3 | 3 | Coogan challenges Packy on whether Substack should build a unified subscription bundle and ad network. Packy pushes back, explaining how creator egos and ad network misalignment cause bundling models to break down in practice. | |
| Category Dominance Investing and Biotech Realities | 6 | 5 | 2 | 2 | The hosts cite Sebastian Mallaby's venture writing and contrast software with hard tech physics constraints. Packy honestly outlines his boundary conditions as an investor, admitting he avoids early science risk in biotech without specialized genomics partners. |
Statements from this episode (13)
Hays: Ramp's down round was caused by market conditions, not poor performance
“The ramp down round was directly tied to the market, not business performance, which is why they're back above that last, you know, financing, just given that you know, they were taking that down round while still putting up ridiculous numbers.”
Hays: Humanoid Robot Startup Raising at $40B With One Customer
“And we got humanoid robot companies with one customer raising at forty billion.”
McCormick: AI Will Produce a Couple of $10T Companies
“There's probably going to be like a couple of 10 trillion dollar AI companies that are going to pay for the whole thing.”
McCormick: Humanoid Robotics Will Erode Margins Into Consumer Surplus
“Humanoids scare the hell out of me as an investor, because it's like this really impossibly hard thing to do with a lot of really, really smart people working on it, where like, if you pull off this impossible thing, then you're competing against these 10 othe…”
McCormick: Large VC funds will survive while emerging funds fail
“I think it's like a really, I think like the big funds are actually super well positioned and all, there's going to be a lot of these like emerging ish funds who try to compete who I just think it kind of like wiped out.”
Coogan Predicts General Catalyst Will Go Public
“I think there's going to be a general catalyst going public.”
Hays: Cursor is generating $100M ARR with 20 employees
“And I think we're really seeing that right now in AI where you have companies like cursor, a big one, you know, with 20 people doing a hundred million of ARR.”
McCormick: Startups can put K-12 education on a Moore's Law curve
“And I think they actually can, you can like put education on a Moore's law, like cost curve and get, make education better for less and less money.”
McCormick: Creator egos make Substack newsletter bundles nearly impossible
“That actually I think in practice, like when you, when you're like dealing with people who have kind of like egos and think that their own thing is like the thing most important are really, really, really hard to pull off in practice. Like I wouldn't want to b…”
McCormick: Cancer is probably gone in 10 years
“I think a hot take would be cancer is probably gone in 10 years, I think is one of my favorite hot takes. There's just so many different attacks on it, and CAR T cell therapies are doing well, and it's a matter of kind of scaling, scaling those out.”
McCormick: Not Boring Capital is shifting toward Series A rounds
“I'm trying to make actually moving closer to the series a now and like not doing deep tech because like, I'm not the guy to underwrite the science. And if I'm like the investor that you're calling to have something that has a bunch of science risk in it, like …”
McCormick: In five years much of finance will run on blockchains
“And I think it's like some point in five years, a lot of finance is going to run on Solana on ETH maybe on sweet or, you know, like a lot of, I think it's inevitable that, that more and more. Finance will move over to crypto stable coins and having Stripe behi…”