Aug 7, 2025 · 1h 28m · news
Figma's 250% Pop - The Greatest IPO Mispricing Ever? Meta & Microsoft Blowout Quarters: Broken Down · 20VC with Harry Stebbings
Rory O'Driscoll · 36m spoken Brian Halligan · 20m spoken Jason Lemkin · 16m spoken Harry Stebbings · 6m spoken
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of 20VC, Harry Stebbings hosts Rory O'Driscoll O'Driscoll, Jason Lemkin Lemkin, and Brian Halligan to break down Figma's massive 250% IPO pop, the inner workings of public listings, corporate compensation design, macro tech trends in AI, and evolving venture capital strategies.
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 7.6% of the talking time here. How this is scored →
Harry as informed peer 2.9 Guest teaching 4.8 Guest disagreement 2.8 Harry pushing back 2.2
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 1:24:11 Rory Rejects Benchmark Gossip Framing
Rory forcefully rejects Harry's attempt to link Benchmark's fund discipline to specific partner departures, calling the premise presumptuous and refusing to comment on personal personnel moves.
Hardest push from Harry ▶ 1:24:11 Harry Presses Rory on Benchmark DeparturesWhen Rory tries to dismiss the question about Benchmark's strategy, Harry refuses to drop the issue and restates his challenge regarding partner defections.
Biggest teaching moment ▶ 1:50 Brian Explains Night-Before IPO Banker TacticsBrian educates the host and room on how investment bankers attempt to favor hedge fund clients during pricing allocations while founders push for long-only institutional investors.
Harry holds his own ▶ 54:40 Harry Confronts AI Spending with Hard Meta StatsHarry demonstrates deep financial preparation by confronting the panel with Meta's specific earnings metrics to question the long-term sustainability of AI capital expenditures.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Video Hook & Guest Previews | 2 | 7 | 1 | 1 | Harry introduces the episode enthusiastically and asks a broad framing question about Figma's IPO pop. Brian takes over, educating the room on the intense night-before pricing negotiations with investment bankers. | |
| The Myth of Underpricing & Engineering the Pop | 3 | 6 | 2 | 1 | Harry asks whether Figma was fundamentally mispriced or if it was exuberance. Rory and Brian elaborate on how order books work and how engineered small pops can unexpectedly explode. | |
| Institutional Price Targets & The Non-Deal Roadshow | 1 | 5 | 1 | 0 | Rory and Brian explain institutional price targets and non-deal roadshows. Harry remains passive as the guests share stories about acquiring long-only institutional backers. | |
| Direct Listings & The Public Market FOMO | 5 | 6 | 4 | 5 | Harry questions whether direct listings should replace traditional IPOs. Rory directly pushes back on Harry's framing, prompting Harry to counter with examples like Circle and CoreWeave. | |
| IPO Timing & Capital Table Defense | 2 | 5 | 2 | 1 | Brian and Rory analyze Zendesk versus HubSpot IPO timing and cap table defense against activists. Harry makes minimal interjections. | |
| NYSE Inside Baseball & IPO Night Celebrations | 1 | 4 | 1 | 0 | Brian shares colorful anecdotes about NYSE floor mechanics and waiting hours for opening prices to settle. The dynamic is purely conversational storytelling. | |
| Dilution and Rethinking CEO Compensation | 3 | 5 | 2 | 2 | Harry redirects the conversation to Dylan Field's compensation package. Brian educates on why modern RSU compensation disincentivizes CEO risk-taking compared to ISOs or PSUs. | |
| The Flaws of Stock Price Triggers | 1 | 6 | 2 | 0 | Rory explains how stock price performance targets broke down in Figma's case due to the immediate pop. Brian explains HubSpot's alternative net-new ARR metric. | |
| Growth Round Moonshots & Recutting Comp | 2 | 5 | 5 | 1 | Jason describes growth round moonshot packages. Rory forcefully disagrees with Jason's assertion about VCs waiving criteria, predicting CEOs will demand package recuts. | |
| Public Markets: The New Source of Cheap Capital | 3 | 5 | 3 | 2 | Harry prompts the panel on whether Canva should go public immediately. Rory explains how public markets currently offer cheaper capital than private growth rounds. | |
| Dispelling the Fear of Activist Investors | 3 | 4 | 3 | 2 | Harry asks how to reassure founders terrified of public activist investors. Brian and Rory explain that VCs are actually a bigger daily hassle than public shareholders. | |
| The Joy of IPO Day & Autopilot Liquidity | 2 | 4 | 2 | 1 | Brian describes the joy of IPO day and his automated monthly share selling strategy. Harry jokingly asks about personal net worth and share holdings. | |
| The Story of HubSpot's Series C | 4 | 5 | 4 | 5 | Harry presses Rory on his exact multiple for HubSpot's Series C. Rory stonewalls Harry's return question, while Brian tells the story of Scale stepping up during a recession. | |
| Building a Massive Business in SMB | 2 | 5 | 2 | 1 | Brian explains his decision to target SMBs over enterprise CIOs. The panel explores how unit economics make SMB models viable. | |
| Pre-Canned AI for Small Businesses | 4 | 4 | 3 | 3 | The panel discusses SMB AI tools before Harry transitions to Meta's earnings, citing specific financial stats regarding EPS and free cash flow. | |
| AI CapEx: Real Frontier vs. Tech Bubble | 3 | 5 | 5 | 3 | Harry references David Cahn's CapEx piece. Rory delivers an analysis of tech CapEx versus app revenue, teasing Harry with jab about European economic lag. | |
| Old School Tech Growth & Oracle's Resurgence | 3 | 4 | 4 | 3 | Brian notes surprising stock growth in legacy tech like Oracle and SAP. Harry asks Rory to pick CEO of the Year between Satya and Zuck, which Rory refuses to answer. | |
| Satya Nadella's Re-Founder Playbook | 1 | 5 | 2 | 0 | Jason argues Satya Nadella deserves CEO of the Year due to navigating corporate bureaucracy to secure the OpenAI deal. The host listens as guests discuss. | |
| Cognition's Rumored Valuation & The Windsurf Drama | 4 | 5 | 3 | 4 | Harry brings up Cognition's acquisition rumors. Jason breaks down the unusual employee buyout terms, prompting Harry to question the true logic behind the deal. | |
| The Realities of Custom Acquisition Deals | 2 | 4 | 2 | 1 | Rory uses literary references to explain the vulnerability of non-key employees in unconventional tech deals. Harry enthusiastically reacts to the quote. | |
| Ramp's $500M Series E & Credit Float Capital | 5 | 5 | 4 | 5 | Harry asks whether Ramp's rapid fundraising reflects capital needs or late-stage excess, challenging whether high-valuation rounds are 'suicide rounds.' Rory refutes the premise. | |
| CRV's Downsizing & The GP Carry Incentive | 5 | 5 | 3 | 5 | Harry introduces CRV's fund downsizing and directly asks Jason if he regrets launching an opportunity fund. Jason responds with candid financial realities of GP carry. | |
| Specialist vs. Full-Stack Venture Funds: Benchmark's Strategy and Talent Retention | 6 | 5 | 6 | 7 | Harry presses Rory on whether Benchmark's fund caps led to star partner defections. Rory rejects the personal gossip framing, but Harry re-engages to force a discussion on specialist versus platform funds. | |
| Choosing Future Guests: Marc Benioff and Jeff Lawson | 2 | 2 | 1 | 0 | Harry asks for future guest recommendations. Jason suggests Marc Benioff and Jeff Lawson, and the episode wraps up collaboratively. |
Statements from this episode (65)
O'Driscoll: Figma's $98 IPO pop only happened because it priced at $38
“The 98 price only happened because the IPO happened at 38.”
Halligan: IPO pricing and allocations are decided the night before listing
“So, first of all, you're making the decision on the price and who the investors are the night before the IPO.”
Halligan: HubSpot's IPO order book was 40x oversubscribed
“Because we were 27 X over subscribed. You know, I think it was 40 X over subscribed.”
Halligan: HubSpot rejected Morgan Stanley's $24 IPO pricing advice
“We wanted to go out at 25. Morgan Stanley said we should go out at 24. And the reason we should go out at 24 is Fidelity has told us That they're in at 24, they're out at 25. Ok, and you really want Fidelity, because Fidelity has trillions of dollars, and they…”
Halligan: Morgan Stanley and Fidelity aligned to lower HubSpot's IPO price
“I don't think there was collusion going on, but definitely Morgan Stanley and Fidelity were on the same side of the table trying to get us to sell at a lower price.”
Halligan: Figma CEO Dylan Field decided IPO pricing, not bankers
“The founders make the decision on what the price is. So Dylan decided at the end of the day.”
Halligan: Companies engineer IPO pops to retain long-term institutional investors
“Part of it also is you want to pop. You want Fidelity and T. Rowe and these long lonely folks to come in and right out of the gate, feel good about their investment. You want them to hold for decades and decades and decades.”
O'Driscoll: Figma's 250% IPO pop was largest since 1999
“Instead of getting, let's call it, the designed 15, 20% pop that makes everyone feel good, you ended up with this absurd 250% pop, right, which is clearly off the charts. I mean, I think it's the largest pop since 1999.”
Jason Lemkin: Startup Employees Care About Stock Value, Not Dilution
“But we forget about the employees don't care about, they don't even know what dilution is. All they care about is what happens with their stock.”
Rory O'Driscoll: Figma Did Not Leave $3 Billion on Table in IPO
“The people who said, oh, Figma left three billion dollars on the table because they could have got 95 dollars a share, are talking out of their ass. Because I can guarantee you, the order book, I think it was one of the prices, 35, 38, whatever it was, there w…”
O'Driscoll: Figma IPO Buyers Set Exit Price Targets Under $110
“All those big buyers who came in at Figma at 38, before they buy, they have an internal process with a price target to exit. None of those price targets are going to be more than a 110 bucks a share.”
Brian Halligan: 'Long-Only' Institutional Funds Actively Trade Public Positions
“People would say long only. They're not long only. They do sell. They come in and out of HubSpot. I see them coming in and out.”
Halligan: Big institutional investors own roughly 90% of HubSpot stock
“It's very little of HubSpot is owned by mom and pop, owned by Harry Stebbings, buying Harry Stebbings's mom. It's like, 90% these big institutional investors.”
O'Driscoll: Direct listings fail to prevent periodic post-IPO price pops
“It may well be that Megapops are a natural intermittent consequence of the IPO process, and that Direct listing doesn't solve that part of the problem.”
O'Driscoll: Startups raise unchanged follow-on rounds weeks after big-name leads
“It's like in the venture equivalent that we're seeing now, you know, the way we're seeing it now when someone really big brand name Does a round. Like, six weeks later, many of these companies are doing a follow-on round. Nothing's changed.”
Brian Halligan: Direct listings are risky unless you're Google or Facebook
“I think the direct listing is like, you're a little bit scared. You're not going to get those long loneliness. You're not going to properly market it to them. And it's seven percent to the bankers in the grand scheme of things. It's not that much. I think it's…”
Halligan: Zendesk never secured long-only investors due to shaky IPO timing
“Zendesk at the time went out. And it was just, it was timing, and it was just a shaky week that they went out, and they just didn't get, they didn't get the big long onlys, and they had a good story, and they didn't get them, and they never really got them. Th…”
Halligan: NYSE and NASDAQ are identical except for ringing NYSE's bell
“You can do NASDAQ or New York Stock Exchange virtually exactly the same, except with the New York Stock Exchange, you get the ring the bell. That's why we picked New York Stock Exchange.”
O'Driscoll: Post-IPO dinners exist to placate founders after bankers underprice IPOs
“My mental model on the dinner is the bankers have just screwed you over for a buck a share, and in return, they buy you a very expensive dinner, and they liquor you up so you forget.”
Halligan: RSUs dampen risk-seeking behavior in tech CEOs compared to ISOs
“It just creates sort of a risk averse behavior in the CEO. Like it's basically cash comp goes up and down a little bit, let's say, but an ISO you're swinging for the fences. Like you've got a strong incentive to swing. And so it's really had a dampening effect…”
Halligan: Ultra-wealthy CEO compensation must be pegged to net worth
“But you kind of have to peg the comp to the net worth. Same thing with Elon Musk. Like if you paid Elon Musk, like Mary Barra makes twenty nine million dollars a year. You think Elon cares about twenty nine million dollars a year? So you have to kind of comp i…”
O'Driscoll: 2021 executive stock price targets like Airbnb's will never be hit
“All the ones that were put in place in 2021 Are stranded, because all those price targets, like the Airbnb price targets, ain't ever going to happen now.”
Halligan: HubSpot ties executive comp to net new ARR and earnings floors
“The way Hellspot does it is on net new ARR. And an earning, like a floor earnings number.”
O'Driscoll: Founders Will Ask VCs to Waive Missed Stock-Price Targets
“My prediction is, and again, I'm often disagreed with on this on comp committees, because I've done some of these where I've tried to make them on tangible targets. What will happen when you do the stock price ones is if the company is doing really well, but t…”
Lemkin: VCs Will Not Waive Unearned Stock Compensation Triggers
“I'll bet you nickels to dollars that doesn't happen because founders are just signing up. I don't know what Brian you see at Sequoia, but founders are signing up for crazy stuff these days. They're signing up for massive stuff. And I don't think a lot of grouc…”
Halligan regrets early HubSpot secondary stock sale to Sequoia Capital
“When we did our round, it was Sequoia. Sequoia came to us and said, we'd like to buy some of your shares in retrospect. It's a horrible financial decision for me, but it was good at the time. And I saw, I forgot a couple million dollars worth of HubSpot shares…”
Halligan: Current Venture Capital Valuations Are 'A Little Bubbly'
“I think the valuation is very high right now across venture. So we'll see how this thing plays out. I think it's a little bubbly right now”
O'Driscoll: Private rounds were cheaper than public capital for three years
“For the longest time, the private round, the money in the private round was cheaper and less hassle for the last three years than the public's.”
O'Driscoll: Cheap capital is now in public markets, making IPOs imperative
“At a highest level, the cheap money is now in the public markets, and Brian's right, you'd be an idiot not to go for it.”
Rory O'Driscoll: Startups needing capital in next two years should raise now
“Like, if you need to raise money in the next two years, now would be a really good frickin' time.”
Brian Halligan: Activist investor horror stories are rare and public markets are rational
“Public investors, like there's so much written about what happened with Zendesk or Autodesk, or these really bad things that happen. It's pretty rare. And I have found that public investors be pretty rational.”
Halligan: Going public will be a top three day in founder's life
“You're exhausted, but the day you go public is going to be one of the top two or three days of your life. It is an amazing day.”
Halligan: Sells fixed number of HubSpot shares monthly to avoid signaling market
“I sell the same number of shares every month since we went public. And the reason I do that is I don't want people to think, I don't want to signal something. If I make a big buy or a big sell, it's going to signal something.”
Every major Sand Hill Road VC rejected HubSpot's 2009 Series C
“It was in the throes of the recession back in and we went up and down Sand Hill road, like Darmesh and I get off the plane from Boston, landed in Sand Hill road. We're like, we got this. We're going to go up and down. It's like 20 meetings. And we go all 20 me…”
Scale Venture Partners invested in HubSpot, Box, DocuSign, and RingCentral in 2009
“Yes, I remember that was in O-Nine. We did HubSpot, Box, DocuSign, and I think RingCentral.”
Rory O'Driscoll: The best time to buy is when nobody else is buying
“The time to buy is when everyone else is not buying, especially when, let's put it out there, you're just little old scale, and you're not Sequoia who came in afterwards.”
HubSpot grew from $1B at IPO to $25B in public markets
“Yeah, the smart money on HubSpot was in the public since we went from a billion dollars to 25. In a relatively short period of time.”
Brian Halligan: Sequoia's strategy of holding post-IPO stock will succeed long-term
“And I think Skoy is really smart. I suspect HubSpot was one of the reasons why they said, Let's hold these companies after they go public. It's back in some cases, but I think it's going to work over the long haul.”
Halligan: Selling software to corporate CIOs is soul-crushing work
“I had spent my entire life Doing the soul crushing exercises of selling to CIOs, and it's just a soul crushing work.”
Halligan: Silicon Valley has a wrongheaded bias against building for SMBs
“There's a big echo chamber in Silicon Valley and big negative bias towards SMB, but you can make it work in SMB. HubSpot and Shopify have shown it. Block has shown it.”
Halligan: Prosumer and Enterprise AI Succeeded, but SMB AI Lags
“The stuff I see, Jason, is there's a ton of prosumer stuff that's working. Lovable's working. Reflet's working. Gamma's working. Like, so many prosumer things seem to be working. And then enterprise is working. You're right. I haven't seen much in between.”
Lemkin: VCs Should Rush Capital into Uncracked B2B SMB AI Market
“So I just think this AI B to B SMB, It's something that hasn't been cracked to Rory's point, and I think we should all just rush all our capital into that.”
Rory O'Driscoll: SMBs want enterprise software features, but tightly packaged and priced
“Anything the big companies have, the small and mid-sized companies want too. They're not different. They just need it packaged tightly and priced tightly so they consume, consume of it in bite-sized chunks.”
Rory O'Driscoll predicts SMBs will adopt pre-packaged AI within two years
“So over the next couple of years, it may well be, as I say, for things like phone answering, simple order dispatch, that there'll be a whole, whole bunch of pre-canned, pre-baked, This is how it works, Mr. SMB. Just turn it on, and you too can sound like a big…”
O'Driscoll: Meta's strength stems from core ads, not AI
“This isn't a AI enabled success. This is, I have an awesome existing business, and it kicks off so much money that I'm allowed spend that money on building this great AI vision, and I can probably do that for as long as my existing business kicks off cash.”
O'Driscoll: Hyperscalers' AI spend is funded by core cash flow
“My big takeaway is not all the AI stuff is working for the hyperscalers. My big takeaway is all their existing businesses are working so well and kicking off so much cash that they can keep doing this for the next year, and they said they're going to keep doin…”
Rory O'Driscoll: AI App Revenue Maxes Out at $30B Against $600B CapEx
“You still add up all the apps revenue, and it probably comes to 25, thirty billion dollars maximum, and the capex to build that is running between four and six hundred billion dollars.”
Rory O'Driscoll: AI App Revenue Will Reach $300B–$400B in 10 Years
“If you fast forward 10 years, that 25, thirty billion of apps, wherever, and you could easily be three, four hundred billion dollars.”
Halligan: Shopify is the only SaaS stock outperforming Oracle and SAP
“If you go from that date and you look at you look at Oracle and you look at SAP, they're both growing, like, 230%. The only SaaS company since August 22 It's growing faster. Shopify. They're growing 300%. So they're outpacing HubSpot, Salesforce, Adobe Box, At…”
Brian Halligan names Nvidia's Jensen Huang as CEO of the Year
“I think the CEO of the Year is Jensen. And I like them, but the other thing I like about Jensen is sort of rethinking the role of the CEO. He's rethinking the CEO playbook. I think he's a pretty good inspiration for CEOs out there today.”
Rory O'Driscoll: GPUs and foundational models dominate the AI tech stack over applications
“I think that the two people who have, the two categories in the stack that didn't meaningfully exist at scale in SAS and cloud land that exists now are the GPUs, which is all Jensen and the models. Neither of those kind of categories even existed. And obviousl…”
Lemkin: Adobe's shift to the cloud required three years of internal convincing
“Adobe just trying to go to the cloud took three years of convincing everybody, okay?”
O'Driscoll: Microsoft's post-OpenAI deal execution under Nadella has been perfect
“If you accept the constraint, That you can't build the core technology internally, which is what Microsoft Had to accept, and he accepted, right? Execution since then has been perfect.”
Rory O'Driscoll on why private AI valuations escalate rapidly during fundraising
“Demand is high for premium assets, so it's a little like it's the private IPO. You float a price of a hundred, and you end up at one 50. You close the price of ten billion, you end up at 15. I think there's just a lot of demand for premium, perceived premium A…”
Lemkin: Cognition mandated 80-hour weeks and laid off 30% of acquired startup
“Well, I guess today, Cognition laid off 30% of the folks they bought, and they offered to buy out all the other 200 employees. They gave them a nine-month package. They told them they either had to work 80 hours a week, six days a week in the office, or they s…”
Rory O'Driscoll: Non-standard acquisition deals leave non-key employees vulnerable
“If you're not one of the key players, the minute you move away from the cap table to, you know, making it up as you go along, if you're not one of the key players, you're very vulnerable to, you know, you're basically, Depending on the kindness of strangers, a…”
Lemkin: Clay raised $100M at a $3B valuation
“Clay just did around at three billion, which is a stunning growth too, right? But they sold a hundred million, right?”
O'Driscoll: High valuations only harm startups if they must raise again
“Raising money at too high a price is only, quote, suicide if you have to raise again. If you don't have to raise again, and all you do is have some investors who've overpaid, and they take four or five years to grow into that valuation, well, that's tough shit…”
O'Driscoll: Ramp is generating $700M to $800M in revenue
“Like, I've heard they're doing roughly seven, eight hundred million dollars.”
Lemkin: VCs should size funds smaller to enter carry mode faster
“Normal times you want to optimize your fund size to achieve the maximum carry you can in a given time, right? And then just go raise another, right? In an ideal world, you might even raise the fund a year, right? So you can get into carry mode as quickly as po…”
Lemkin: Opportunity funds were not worth the extra effort for 15% returns
“Wasn't worth it For me to do the opportunity funds. It's not enough. Like I'll make like 15% more money. It's not enough money, right?”
O'Driscoll: Opportunity funds fail without $20B portfolio mega-winners
“Unless you end up with one of the very few companies that are not just amazing, but are super amazing, where they can be a twenty billion dollar outcome, your ability to deploy lots of capital relative to your early stage fund is actually much smaller than you…”
Jason Lemkin: Benchmark is no longer in top VC conversations on X
“If you look on social media, benchmark isn't listed the way Andreessen and Sequoia was like it was a generation ago. It's just not, does it matter? Harry, Harry's built a big brand. He's concerned. It matters. You could argue both sides, but when the industry …”
Rory O'Driscoll: Specialist VCs face deal-loss risk; mega-funds risk subpar returns
“The risk you face as a specialist is you get crowded out by the noise, and people don't know you're amazing enough, and therefore you lose some of the at-bats to the people who have more brand. The risk you face as a brand is in your wild urge to put all the m…”