Sep 22, 2023 · 48m · more-or-less
#15: Instacart’s Fake IPO and Why Hiring in Tech Is So Broken · More or Less Podcast
0:00 / 0:00
▶ Watch on YouTube →
gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of More or Less, the co-hosts critique unoriginal Big Tech executive hiring, examine the enduring dominance of Silicon Valley over tax-haven hubs, and unpack Instacart's humbled IPO to debate the distortions of late-stage private venture capital.
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 99.3% of the talking time here. How this is scored →
The hosts as informed peer 4.7 Guest teaching 4.1 Guest disagreement 3.4 The hosts pushing back 3.7
speaking balance: gold is the hosts, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 37:05 Life360 counterargument against public market rigor
Brit directly challenges Dave's assertion that public listing enforces healthy rigor, citing her actual board tenure where compliance burdens detracted from operating momentum.
Hardest push from the hosts ▶ 18:12 Calling out event hypocrisyJessica forcefully rejects Sam's dismissive stance on tech networking by pointing out that his calendar is packed with Hollywood VCs and university talks.
Biggest teaching moment ▶ 28:10 Dissecting the fake IPO architectureSam educates the table on how late-stage private checks and controlled floats create artificial day-one pops rather than genuine public market liquidity.
The host holds their own ▶ 20:46 Inside reporting on Instacart board turmoilJessica establishes domain authority by sharing The Information's scoop on Apoorva Mehta clashing with Sequoia over IPO timing prior to Fiji Simo's appointment.
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 |
|---|---|---|---|---|---|---|
| More or Less Animated Title Sequence and Podcast Branding | 1 | 1 | 1 | 1 | Lighthearted housekeeping and playful banter as Jessica broadcasts from the back of her hot car while the group jokes about car sponsorships and audio quality. | |
| Broken Tech Hiring: Big Tech Executive Recycling and Gerontocracy | 5 | 5 | 4 | 4 | Jessica brings reporting on executive poaching between Amazon and Microsoft, while Sam and Dave debate whether big tech hiring is becoming an uninspired gerontocracy versus hiring for potential. | |
| The Florida Venture Taboo, Tax Optimization, and Miami Boomerang | 6 | 5 | 4 | 4 | The panel discusses old VC taboos against Florida investments, with Sam contrasting the margin-optimizing mentality of tax-havens against Silicon Valley's pie-growing mindset, while Jessica notes The Information's reporting on the Miami boomerang. | |
| Silicon Valley Resurgence: Event Culture, Sales Leadership, and Networking | 5 | 4 | 4 | 5 | Jessica calls out Sam's hypocrisy for attending networking events right after mocking SV event culture, while Brit pushes back that great sales leaders must be everywhere. | |
| Instacart’s Fake IPO and the Late-Stage Valuation Collapse | 7 | 6 | 4 | 5 | Jessica breaks down insider reporting on Instacart's board clashes and IPO mechanics, while Sam argues the listing is fundamentally a fake IPO structured with insider support rather than broad institutional market appetite. | |
| The Great Debate: Early IPO Rigor Versus Private Capital | 7 | 6 | 5 | 5 | Dave argues that early IPOs enforce business discipline, while Brit counters with her firsthand Life360 board experience showing public compliance can impede growth. Jessica cites Reed Hastings's perspective on early public accountability. | |
| Final Takeaways, Production Banter, and Next Episode Tease | 2 | 2 | 2 | 2 | Brit humorously wraps up the episode by contrasting concise summaries against long-winded male pontificating as Jessica signs off ahead of upcoming travel. |
Statements from this episode (16)
Jessica Lessin: Amazon Poached Microsoft's Chief Product Officer for Hardware
“Yeah, well, we know where Sam thinks, but also for those who like such intrigue, Amazon poached Microsoft's chief product officer as their new head of hardware, so I think that's always funny to me, these big companies poaching from each other.”
Jessica Lessin: Former Flexport CEO Dave Clark Will Return to Big Tech
“Well, I, it's interesting because like Dave Clark, the who ran Amazon e-commerce left to go to Flexport and is now on the market. It's a big question where he's going to end up, but I think he's going to end up at like, One of the exact same companies.”
Hiring For Experience Defends the Floor; Hiring For Potential Plays to Win
“Yeah, it depends that you're defending the floor or you're trying to win, right? Like, this is like, defend the floor, be boring move.”
Big Tech's 'Fat and Rich' Senior Managers Must Be Replaced
“But then I think there's this whole senior level of managers who are kind of fat and rich, you know, in like the tech world. And they're good people. They're smart. Like they're fine. But like figuring out how to get them out and get like the young hungry buck…”
Lessin: Facebook was originally incorporated as a Florida LLC
“Facebook was originally a Florida LLC, right?”
Historical VC Rule: Avoid Startups in Las Vegas, Santa Barbara, or Florida
“Don't invest in companies based in Las Vegas, Santa Barbara, or Florida. Rationale was that people love those places for lifestyle, and you don't want an entrepreneur who thinks about work-life balance.”
Florida Founders Are Tax Optimizers; Silicon Valley Founders Grow the Pie
“The Florida signaling is, right? Basically, you like no income taxes, right? You're an optimizer. You want that last dollar, right? Well, that's, but why is crypto? It's like the same thing with, like, crypto is all in Puerto Rico. Like, all these crazy, like,…”
Fiji Simo Rescued Instacart, Making It Profitable Within Two Years
“I just want to give credit to Fiji who came in to this business while it was down, like shrinking, 16% year over year within two years, got it profitable, had like five straight quarters of growth, took it public.”
Less Than 1% of Founders Taking Companies Public Are Female
“One of like less than one percent of the founders who took a company public in the last 10 years were female.”
Every Instacart Investor Since 2015 Is Underwater Post-IPO
“Basically everyone, everyone since 2015 is underwater.”
Instacart’s Debut Is a 'Fake IPO' Driven by a Tiny Float
“This is, like, a fake IPO, right in terms of how it's being structured. Like, yes, they need to get public, and they're getting public, and they're technically public. Yes, all true. Tiny float, right? You know, set it up, you know, set it up in a way where, l…”
Sam Lessin: Meta, Google, and Amazon will be uncapped AI winners
“The big platforms, the Facebooks, sorry, the Metas, the Googles, the Amazons, are really going to be obviously huge winners from AI, and there's no cap on how big they can get anymore.”
Sam Lessin: Lyft has financially been a huge disappointment for dollars invested
“Lyft has obviously been financially a huge disappointment, right? Like for dollars invested, like some people might've gotten rich on it by timing it right and being in and out and lucky. But the reality is, is Enormous amount of money went in, far more than t…”
Sam Lessin: BuzzFeed trades at 33 cents with a $50M market cap
“You know, you can look at all these IPOs, my favorite being Buzzfeed trading at 33 cents right now down from 10 dollars. It's like, you know, Buzzfeed's entire market cap is fifty million dollars, right?”
Falling Tech Stock Prices Create Downward Spirals That Ruin Hiring
“In practice. What actually happens a lot of time is price equals quality. So like the price goes down and then you can't hire anyone, right? Ironically, people want to work at like the thing where like you get all the job applications and the stock price is to…”