Jun 19, 2025 · 1h 9m · news
Chime IPO: Are IPOs Hotter Than Ever? · 20VC with Harry Stebbings
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In this episode of 20VC, host Harry Stebbings sits down with venture capitalists Jason Lemkin Lemkin and Rory O'Driscoll O'Driscoll, alongside Handshake founder Garrett Lord, to dissect Meta's massive $14.8 billion transaction with Scale AI, evaluate shifting fintech valuations, debate founder CEO continuity, and analyze signs of a potential IPO market resurgence.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 14.2% of the talking time here. How this is scored →
Harry as informed peer 4.4 Guest teaching 4.3 Guest disagreement 3.3 Harry pushing back 3.7
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 58:10 Rory Rejects Host's Question Premise
Rory directly rejects Harry's prompt comparing Glean to Dropbox, calling it an irrelevant question due to fundamental differences in enterprise software systems of record.
Hardest push from Harry ▶ 15:28 Harry Refuses Founder PR AnswerHarry forcefully interrupts Garrett's boilerplate corporate PR response to restate the real operational lesson regarding startup capital survival.
Biggest teaching moment ▶ 58:00 Rory Educates Host on Enterprise Software QuadrantsRory breaks down enterprise software architecture to show why overlay AI agents and systems of record operate on completely different competitive vectors.
Harry holds his own ▶ 35:52 Harry Demonstrates Media & Mindshare ExpertiseHarry pushes back on Rory's facial expression and skepticism by explaining how continuous funding announcements build brand momentum and mindshare on social channels, convincing Rory to agree.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Unpacking Meta's $14.8B Deal with Scale AI | 3 | 4 | 1 | 2 | Harry introduces the $14.8B Meta/Scale AI deal and asks open questions to Garrett and the panel. Garrett and Rory break down the mechanics of the deal and the underlying PhD data labeling business, while Harry mostly facilitates. | |
| Future of AI Training Data and Spend Reallocation | 7 | 4 | 2 | 5 | Harry steps in with a clear, sharp thesis explaining Mark Zuckerberg's rationale for the Scale transaction, pointing out it represents less than one percent of Meta's market cap and buys PR messaging and talent. Rory explicitly validates Harry's analysis as accurate. | |
| Would You Sell Handshake for $4 Billion? | 6 | 2 | 3 | 7 | When Garrett responds to a question with boilerplate company mission PR, Harry directly interrupts and rejects the framing, asserting that the true takeaway is staying alive and managing cash. Harry asserts strong podcast leadership and tactical startup knowledge. | |
| LP Liquidity and Bypassing the DOJ | 5 | 4 | 3 | 3 | Harry guides the discussion onto LP liquidity and specific VC fund returns, citing Accel's return figures. Jason and Rory engage in a detailed discussion on antitrust workarounds and customer trust erosion. | |
| The Philosophy of Founder CEO Continuity | 4 | 5 | 2 | 2 | Harry prompts a discussion on founder CEO replacement by asking Rory if he has ever fired a founder. Rory and Jason deliver nuanced insights on board dynamics and the high failure rate of replacing founders. | |
| Fintech Valuations: Ramp vs. Brex vs. Mercury | 7 | 4 | 3 | 7 | Harry challenges Rory's dismissive reaction regarding Ramp's continuous fundraising rounds, arguing that fundraising acts as a crucial PR engine to maintain relevance and mindshare. Rory concedes that Harry's insight is correct. | |
| AI Heat: Perplexity, OpenAI, and Defense Tech | 3 | 5 | 7 | 2 | The panel debates OpenAI's defense deal and its ongoing friction with Microsoft. Jason forcefully disagrees with Rory's claim that Microsoft holds leverage, resulting in a strong guest-versus-guest contrarian debate. | |
| The IPO Resurgence: Chime and Gusto | 6 | 4 | 4 | 7 | Harry refuses to accept Rory's claim that recent tech IPO pops do not influence late-stage tech company decision-making. Harry argues the new market data creates fresh pricing confidence, forcing Rory to admit 'I'll give you that.' | |
| The Old Guard vs. The New Guard: Glean and Dropbox | 2 | 7 | 7 | 2 | Rory dismisses Harry's question comparing Dropbox to Glean as conceptually flawed and irrelevant to enterprise software categories. Harry accepts the critique lightheartedly. | |
| The Future of Slack and the Salesforce Ecosystem | 3 | 5 | 2 | 2 | Harry asks if Slack's best days are behind it following Salesforce's API restrictions. Jason schools the room on Slack's continued double-digit growth relative to Salesforce's single-digit core growth. | |
| Kalshi Quick-Fire: Apple's U.S. Manufacturing Prospects | 3 | 3 | 2 | 1 | Harry hosts a rapid-fire prediction segment on Apple US manufacturing and S&P index movements. The conversation is lighthearted and collaborative as the guests share personal portfolio allocations. | |
| Kalshi Quick-Fire: Will a Chinese AI Model Take the SOTA Crown? | 4 | 5 | 3 | 4 | Jason argues strongly for Chinese AI model capability, rapidly convincing Rory to switch his stance on Kalshi odds. Harry teasingly points out Rory's quick shift in opinion. |
Statements from this episode (33)
Lemkin: Scale AI is a dead man walking without its founders
“There's no way that scale can recover from losing its founders. I love you, but it's a dead man walking instantly.”
O'Driscoll: Microsoft holds leverage in ambiguous situations because it isn't existential
“In situations of ambiguity, the person who has the most leverage has the best chance to win, and I would argue Microsoft has quite a lot of leverage because it's not existential for them, especially now.”
Lemkin: Scale AI revenue will rapidly decline following Meta deal
“If only OpenAI is committed to maintaining that, As a partial presence, I assume the revenue will decline rapidly, right?”
O'Driscoll: Scale AI reached $800M to $900M revenue before Meta deal
“It's an amazing business. It grew to eight, nine hundred million dollars.”
O'Driscoll: Meta took 49% non-voting Scale AI stake for $14 billion
“Facebook slash Meta announced a fascinating transaction whereby they, that definitely is a bit of a head scratcher, whereby they invested fourteen billion into scale AI, took 49% non-voting control, allowed the other investors to literally take that money back…”
Lemkin: Investors should challenge founders to sell to test their conviction
“I tell all founders to sell now, by the way. I just, I, only as a challenge. I'm not saying you shouldn't take this fake offer, but this is my, this is what I, my life lesson. I tell you to take it. And then if you come back the next day and say what you just …”
O'Driscoll: Founder responses to hypothetical buyout offers are completely useless
“My observation is no one's opinion on what they would do at a hypothetical, hypothetical offer is worth a damn. And what people actually do when the money comes into view tends to be very different on both sides.”
O'Driscoll: Venture capital liquidity in 2025 will be significantly higher
“Look, there's no doubt that liquidity this year is gonna be way up on the last couple of years.”
O'Driscoll: Scale AI cannot sell to LLM providers competing with Meta
“Practically speaking, it's hard to imagine an independent, viable business selling to the LLMs who are the competitors to your 49% owner, where your founder and charismatic CEO is currently working.”
Stebbings: Accel made $2.5 billion and Paige Craig 1,000x on Scale
“Excel made 2.5 billion dollars. Well done, Daniel Levine. Amazing seed bet early. Paige Craig led a pre-seed, a thousand extra turn.”
O'Driscoll: Surprising a founder with termination is a massive board failure
“If you walk in and fire a founder or any CEO and they're surprised, you have massively failed as a board member because you didn't have the guts to tell them in advance you're worried.”
Lemkin: 90% of B2B tech IPOs retained their founder CEO
“I did analysis of all the B to B IPOs. Okay. Of the IPOs. 90% still had the founder CEO as CEO, and as near as I can tell, all but one had an elective step down, ok?”
Lemkin: There is no hope for B2B startups without founder CEOs
“If we're aiming for these great outcomes and nothing else matters today in the B to B world, Then if the founder CEO is out, I'm out because there's no hope in B to B. This is just my view. If the founder CEO is out, I'm out.”
O'Driscoll: Sequoia missed Facebook because Zuckerberg feared Mike Moritz replacing him
“Part of the reason that Sequoia aren't in Facebook is residual frustration with Mike Moritz for prior, you know, prior situations where they had in fact made a CEO change”
Stebbings: Mercury generates $500 million in revenue at a $3.5B valuation
“Brex is like 10, 11. And Mercury's at three and a half, with 500 in revenue”
Lemkin: Ramp raised $200 million at a $16 billion valuation
“Here's the thing, it's two hundred million at sixteen billion.”
Lemkin: Mercury's underlying banking relationships are worth zero dollars
“I don't think Mercury's bank relationships are worth anything, Harry. I think they're worth zero.”
Lemkin: Private markets irrationally ignore gross margins when applying ARR multiples
“I still feel like for startups, we're giving Revenue valuations that don't have an adjustment for different ways their comps trade in the private markets. And if ramp is in a space that's two to four X revenue at when it's public or whatever that you could loo…”
Lemkin: Microsoft has no leverage over OpenAI because AGI is imminent
“The reason I think they have no leverage is because I think that whatever AGI is, we're going to be there pretty soon.”
O'Driscoll: AGI's arrival will be defined by Microsoft and OpenAI litigation
“My comment is we're going to hit AGI when Microsoft and OpenAI litigate what OpenAGI is.”
O'Driscoll: Tech companies with $200M to $500M ARR are preparing IPOs
“I think it's much more true for the whole flotilla of companies in that 200 to four or 500 range who have been trying to figure out where to go and can now see some kind of exit. For those folks, everyone is dusting off their plans.”
Lemkin: Databricks recently held an analyst summit and is IPO-ready
“Literally the fact that this last week they had an analyst summit where they went through all their metrics, their revenue, their growth rate through through an entire group of investors and analysts says to me, they will decide one data file and it will just …”
O'Driscoll: Scale passed on Gusto after underestimating the founder and market
“I think I underestimated both the founder and the openness of the market to switch and I'll say something else, the willingness of investors to pay up quickly for that, such that it got outside my price range very quickly, right? Stuff happens, you know, and y…”
O'Driscoll: Dropbox lacks a significant enterprise customer base compared to incumbents
“Your right to win is predominantly in your existing customer base, and ServiceNow is a big one, and Salesforce has a big one, and brutally in the enterprise, Dropbox doesn't.”
O'Driscoll: A perfect product wouldn't win Dropbox new enterprise customers over Glean
“Even if Dropbox had shipped a perfect, hear me out, even if Dropbox had pitched a perfect functionally equivalent product to Glean, it would mean that for their existing business customers, which is a smallish percentage of their total business, they would win…”
Lemkin: Slack and Tableau are growing faster than core Salesforce
“All of their, not all of them, but the light, so many of the acquisitions, Slack, even Tableau, which I think was founded in the fifties. They're actually all growing faster than the core Salesforce. So like, we can say, oh, Slack isn't what it was, which it i…”
Lemkin: Slack faced an existential ceiling by refusing to become multi-product
“My view, Stuart is a generational founder, right? Did it multiple times. Did the kind of CEO we'd all love to work for, right? But I think deep down in his heart, he didn't want to do multi-product or they would have been multi-product. Like it had an existent…”
Lemkin: Apple will announce US iPhone assembly operations within the year
“I think, listen, I don't, I would have to do more analysis to see if, it's not possible, right? If it's close to impossible, but announcing it and beginning a process, you might have to do it. You just might have to do it. I'm going to go yes.”
O'Driscoll: Tim Cook will not announce impossible US iPhone assembly operations
“I think politically it would be smart to announce it, even though it's impossible. I think Tim Cook is such a straight shooter that he just couldn't pull it off with a straight face because everyone was, no, it's absolutely bullshit.”
O'Driscoll: Investors should be judged by portfolio positioning, not public opinions
“I think when people ask, especially investors, their opinion on shit, the correct answer is, don't even answer that question. The real question is, where is your position?”
O'Driscoll: Personal portfolio allocation is 75% equities and almost zero bonds
“And I'm with Jason, I'm about 75% equity, mildly terrified, you know, almost nothing in bonds and then rest in short-term and weird stuff.”