Jessica Lessin (@Jessicalessin) header
Jessica Lessin (@Jessicalessin) profile picture

Working for a better journalism future. Founder, @theinformation. Founder, @lessinmedia. Co-host @moreorlesspod

San Francisco
Joined September 2007
Photo by Jessica Lessin (@Jessicalessin)Photo by Jessica Lessin (@Jessicalessin)Photo by Jessica Lessin (@Jessicalessin)Photo by Jessica Lessin (@Jessicalessin)Photo by Jessica Lessin (@Jessicalessin)Photo by Jessica Lessin (@Jessicalessin)Photo by Jessica Lessin (@Jessicalessin)Photo by Jessica Lessin (@Jessicalessin)Photo by Jessica Lessin (@Jessicalessin)
This week on More or Less we got @parkerconrad to say the quiet part loud. Parker: the VCs who promised mass engineer unemployment within 9 months were flat wrong — "the biggest load of bullshit." Salaries are higher, the market is tighter, and a great engineer is worth MORE today than a year ago. Argue with him, not me. His moat thesis for the agent era is sharper than it sounds: the winner isn't who solves problems best, it's who SEES the problem first. If you're waiting for the customer to ask, someone else already solved it. My version: I gave a private URL key to my raw notes file to my entire fleet of agents. They check it every minute or two and compete to finish tasks I never assigned. Most of what comes back is useless. Doesn't matter — directionally it's the whole game. And yes, Parker confirmed you can set up lottery compensation in Rippling today: minimum wage + a 5% shot at $1M every pay period. Jess says it's horrible for employees. I say everyone's already on Polymarket — people desperately want to be paid randomly. Go listen, then come fight in the replies.
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I haven’t stopped thinking about @parkerconrad’s point that companies will win if they help people FIND problems to solve faster. With AI, lots of companies will be able to SOLVE problems. But detecting them before people know they exist will be key. Fun pod this week. Thanks for joining me and @lessin @parkerconrad!
Replying to @parkerconrad
@parkerconrad, founder of Zenefits and now CEO of Rippling, joins @lessin and @Jessicalessin. No Morins this week. A year ago VCs were telling him software engineering was months away from mass unemployment. His update: salaries are higher, the market is tighter, and a great engineer is worth more today than ever. He argues the only moat left in AI is seeing the problem before your customer does. That good gross margins can be a sign nobody's actually using your product. And that Rippling isn't a software company at all. @lessin counters with his own setup: a private notes file he hands to four different agents, so they race each other to finish things he never asked them to do. @Jessicalessin brings the mood from New York, where the money people don't think the $8 trillion CapEx bill pencils out, and financing is about to get much harder. Plus Deel fighting a federal grand jury subpoena, Anthropic's IPO date, and Sam's plan to pay people minimum wage with a 5% shot at a million dollars. New episode out now. Topics: 01:14 Parker Conrad joins, no Morins this week 02:13 Everyone watched the election on prediction markets, not TV 04:09 The blue wave, and why the market went up anyway 07:48 Hyperscalers, data centers, and builds that just got harder 09:27 California's wealth tax fails 10:24 Why paper billionaires can't pay a wealth tax 12:17 The financing trick where one investor sets the headline price 13:06 New York's mood: AI financing is drying up 13:45 Sam: we've run out of money in the world 15:09 Parker: good gross margins can be a bad sign 15:30 Anthropic's IPO date and OpenAI's approach to margins 16:44 Rippling's IPO plans and the public market retirement community 18:26 The SaaS apocalypse that didn't happen 19:00 "Rippling is not a software company" 20:29 AI for boring: government forms, faxes and fraudulent audits 25:36 The only moat left is seeing the problem first 28:01 Sam's notes file and the agents that compete over it 29:32 Instinct keeps asking Jess the same question 30:02 Today's agents are shitty assistants 30:49 Permissions architecture as the real advantage 32:21 Where Rippling makes margin and where it makes zero 33:19 Usage pricing and deleting the bottom half of a job 34:36 What you're really selling is a promotion 36:04 Software written at installation time 37:26 Why you shouldn't vibe code permissions 38:07 AI is excellent at using software, humans are not 39:42 Should an AI negotiate your pay? 41:05 Rippling's $17M seed and two years before the starting line 42:07 Why reversibility decides how fast you can move 44:52 The Deel lawsuit and a federal grand jury subpoena 46:06 Sam: your job doesn't look fun to me 48:40 The engineer layoffs that never came 49:25 Random reward payroll, a very bad idea 51:26 Overrated and underrated in Silicon Valley 54:01 Sam's New York Marathon 55:14 Starting a company: the narrow ray of daylight
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Jessica Lessin retweeted
Scoop: Microsoft said in earnings it spent $5 billion less on capex than expected bc data center capacity it was planning to rent wasn’t ready on time. Microsoft didn’t name the ā€œthird partyā€ behind those delays, but one of them is Iren. theinformation.com/briefings…
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This was super fun. Don't miss @parkerconrad on @MoreorLessPod tomorrow!
Tomorrow's More or Less is the Less-ins (me and @Jessicalessin) with probably the number-one revenge founder of all time @parkerconrad...
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Always fun to be live from NY on @squawkbox
ā€œI think relative to OpenAI, it’s a pretty efficient business,ā€ says @Jessicalessin of Anthropic ahead of its IPO: cnb.cx/4zvEzeX
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Jessica Lessin retweeted
Our roundup of how Tuesday's election will affect the tech sector, including: - The prospect of AI legislation given Trump's veto power - Why hyperscaler stocks are going up and neoclouds are going down - The ramifications for Elon Musk - How 2028 presidential prospective candidates are already getting advice on their AI platforms - A very, very bad night for crypto W/ @nickwingfield and featuring @bradrcarson, @JayCarney and @adamkovac theinformation.com/articles/…
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Jessica Lessin retweeted
NEW: Palo Alto Networks' deal machine also doesn't stop. Next on the list is Clutch Security, an AI agent security startup for ~$500M. via @theinformation
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Today made me think back to last week when I interviewed Amanda Peterson Corio, who is responsible for powering all Google's infrastructure. I asked her if Google would acquire more companies in the pipeline directly. She said: "We're constantly evaluating what makes most sense, where does it bring in-house efficiencies at scale, and, and where does it not? Where is someone else better to do it outside of a company? I don't have an answer for you today, but we're always evaluating that."
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Jessica Lessin retweeted
Your company went public at $185, soared to $311, now the stock is at $90. Your RSU is taxed at IPO price. In the old days when you can't sell for at least 180 days, you should be pretty unhappy right now. But thanks to the increasingly popular *staggered* lockup, some may actually be fine! theinformation.com/newslette…
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Wild chart here.
Apollo is poised to control $75 billion worth of AI chips through deals with SpaceX and Anthropic. That would give the private equity giant a bigger chip stockpile than any neocloud and put it behind only the major hyperscalers. Read more: thein.fo/4ixcAFH
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Ok, it is obviously early to say this but I think the market reaction today points to the fact that investors have a very nuanced lens on the AI trade -- which could be good news for those worried about an eventual huge crash. Rather than a big wipeout of everything today, we're seeing the market trade up a little, hyperscalers up a little, chips down and neoclouds down. That suggests that the ai trade doesn't play just one way which is probably good news for those who are concerned that weakness in some companies could pull the whole market down. Obviously, major changes in the macro, revenue growth halts, etc could still collapse the whole pie. But the way things are trading now (with a relatively modest shock) suggests a more nuanced picture.
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The fact the market is up right now means investors don't think the data center bans are going to fundamentally delay the big hyperscalers on infrastructure. That's interesting.
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Jessica Lessin retweeted
You can't make this up: Our latest investigation into how expensive high-bandwidth memory chips get smuggled to #China from #SouthKorea. The trick? Pair them w/ cheap server chips to avoid export detection; solder the memory chips off the cheap server, viola. via @theinformation
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