Kevin Weil

Operator in Residence, Scribble Ventures · 1 appearance on the record.

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Kevin Weil is an executive and product leader who served as Chief Product Officer at OpenAI, President at Planet Labs, VP of Product at Instagram, and SVP of Product at Twitter. He also co-founded Meta's Libra/Novi cryptocurrency project, advises and invests with Scribble Ventures, and sits on the board of Cisco.

16statements → 1claims → 1claims resolved → 4.25/5average certainty → 2.19/5average debate potential → 4.2/5argument clarity · the sources → 9said about them ↓

0 supported 1 partly supported 0 contradicted how the 1 claim stands · each chip opens the sources

1 assertion · 4 opinions · 6 insights · 3 disclosures · 2 what ifs · every statement was checked. The predictions and assertion are the 1 claim: statements the public record can support or contradict. 1 is resolved. Everything else (opinions, insights, what ifs, disclosures) can never be settled by the record, so it carries no assessment.

The record, in short

What the tape says about how Kevin argues and how the claims held up. Everything they said, and everything said about them, is in the tabs below.

Argument clarity: do they answer the question? how? →

4.2 / 5 directness 4.2 · coherence 4.7 · precision 4 · compression 3.7

redirected or did not address 5 of 41 assessed questions (12%). Watch them ▸

This is a score against a rubric. It is not a rank. Every host question → answer exchange is scored with names hidden on directness, coherence, precision and compression, 1–5 each, on meaning alone: disfluencies are ignored, and only raw unedited episodes count. This is the score that measures thought. Every scored exchange, scores shown → · The rubric and its checks →

How they sound: speaking style how? →

274 words/min while actually speaking · 18.5 um and uh per 1k words · 16 false starts per 1k · 32.6% of pauses land inside a clause

Measured by listening to the audio itself: 8,902 words across 1 episode of raw-level tape, transcribed verbatim with every um and uh kept, each one attributed only where the alignment onto our timed stream is unambiguous. These are measurements of speaking style. We do not rank them: across this corpus, fluency and argument quality are nearly uncorrelated (ρ≈0.2), and smooth talking does not signal clear thinking. How it's measured →

How the interview went all their pushback → series average →

Across 1 rated episode:

host pushback ▾ 4/10

pushed back at the host ▾ 1/10

setup questions received 60%

host pushback: the hardest questions Harry asked, tap to play ▶ 6:19“From the outside, and maybe this is naive, it looked like a reactive move from, like, towards Snapchat's, obviously, stories which were phenomenally successful. Is that true?” ▶ 10:30“Can I ask, does that, does that work when you're testing new products? And what I mean by that is with the boldness and decisiveness, it goes against the gradual release iteration …” ▶ 49:22“What's been the biggest miss and what did you learn from that?”

when Kevin pushed back ▶ 10:53“Well, so this is one of my personal product beliefs. Testing doesn't mean, timidity.”

What they said16 What others said9 Episodes1

Everything Kevin Weil said on 20VC that made the record, most notable first. Filter by type, assessment or year in the ledger →

What-if

Weil: Instagram Stories would have failed with a timid, experimental rollout

“If instead we'd done the timid thing and put it like in the back of a third tab and like, well, if people find it, we'll do a one percent experiment and maybe it'll work. Like it never would have taken off.”

Kevin Weil Oct 7, 2022 ▶ 10:15 Kevin Weil: Lessons from Leading Product at Instagram & Twitter | 20VC #934 · 20VC with Harry Stebbings

What-if

Weil: Directly plopping Snapchat Stories into Instagram would have failed

“But I think if you had just taken stories and like plopped it in the middle of Instagram, it wouldn't have worked.”

Kevin Weil Oct 7, 2022 ▶ 7:36 Kevin Weil: Lessons from Leading Product at Instagram & Twitter | 20VC #934 · 20VC with Harry Stebbings

Assertion Partly supported

US State Department asked Twitter to reschedule maintenance during Arab Spring

“Someone from the State Department reached out, and this is a public story, so I'm not saying anything that can't be said. Someone from the State Department reached out and said, wait, wait, you can't go down at, you know, two a.m. Pacific. That's the middle of…”

Kevin Weil Oct 7, 2022 ▶ 28:07 Kevin Weil: Lessons from Leading Product at Instagram & Twitter | 20VC #934 · 20VC with Harry Stebbings

Insight

Weil: Effective organizations alternate leadership tiers between instigators and harmonizers

“You want alternating skills, just like you were saying, you want alternating skills, and he kind of classified people into, like, you know, are they kind of I'm trying to remember the word he used I don't remember, he had a provocative word for it, but basical…”

Kevin Weil Oct 7, 2022 ▶ 34:20 Kevin Weil: Lessons from Leading Product at Instagram & Twitter | 20VC #934 · 20VC with Harry Stebbings

Disclosure

Weil passed on investing in former colleagues who built successful startups

“There are a couple of companies that I chose not to invest in because they were founded by people whose work that I just, that, that I worked with and for whatever reason in that environment weren't amazing. And so I made the assumption that that was them, not…”

Kevin Weil Oct 7, 2022 ▶ 49:25 Kevin Weil: Lessons from Leading Product at Instagram & Twitter | 20VC #934 · 20VC with Harry Stebbings

Opinion

Weil: Venture capital industry is fifty-fifty on hard work versus hype

“Less hype, more hard work for founders. I think the industry's kind of fifty-fifty there, you know. Some people are in, like, hustling every single day for the right things and helping their portfolio companies, and others are not.”

Kevin Weil Oct 7, 2022 ▶ 54:24 Kevin Weil: Lessons from Leading Product at Instagram & Twitter | 20VC #934 · 20VC with Harry Stebbings

Opinion

Weil: Instagram co-founder Kevin Systrom is the best product editor

“He's the best editor I've ever seen.”

Kevin Weil Oct 7, 2022 ▶ 4:18 Kevin Weil: Lessons from Leading Product at Instagram & Twitter | 20VC #934 · 20VC with Harry Stebbings

Disclosure

Weil: Instagram explicitly credited Snapchat when launching Stories

“When we launched stories, the number one thing we made sure to say was like, kudos to Snapchat. You invented this format.”

Kevin Weil Oct 7, 2022 ▶ 6:41 Kevin Weil: Lessons from Leading Product at Instagram & Twitter | 20VC #934 · 20VC with Harry Stebbings

Insight

Kevin Weil: A/B testing is orthogonal to product boldness

“Testing doesn't mean timidity. You can always use the fact that you're testing something and you can run an AB test to test something, 99% and have a one percent hold back. You don't have to test one percent in Australia, right? Testing gives you data. You can…”

Kevin Weil Oct 7, 2022 ▶ 10:58 Kevin Weil: Lessons from Leading Product at Instagram & Twitter | 20VC #934 · 20VC with Harry Stebbings

Insight

Kevin Weil: Qualitative feedback gets lost in large-scale data

“It's really important to have lots of data because data tells you important things. There's no excuse for not knowing data, but I actually really think anecdotal feedback is valuable because a lot of times the anecdotes can get lost in the in the data itself, …”

Kevin Weil Oct 7, 2022 ▶ 12:28 Kevin Weil: Lessons from Leading Product at Instagram & Twitter | 20VC #934 · 20VC with Harry Stebbings

Insight

Weil: Rigid product strategies require product-market fit; early startups pivot frequently

“Like you invest in the early stages in companies and they're going to pivot three times before they find anything. So laying out a strategy and sticking to something, it assumes that you have some degree of product market fit.”

Kevin Weil Oct 7, 2022 ▶ 18:08 Kevin Weil: Lessons from Leading Product at Instagram & Twitter | 20VC #934 · 20VC with Harry Stebbings

Insight

Weil: Scaling leaders must consistently repeat core priorities over presenting new ideas

“And in actuality, especially as your organization grows, it's really important to just say the same things over and over again. And so you got to make sure that those are the right things that you're sticking to the points that really fundamentally matter that…”

Kevin Weil Oct 7, 2022 ▶ 19:57 Kevin Weil: Lessons from Leading Product at Instagram & Twitter | 20VC #934 · 20VC with Harry Stebbings

Disclosure

Kevin Weil: Scribble rejects investments requiring stacked assumptions for 100x outcome

“So our litmus test is what do you have to believe for this company to be a hundred X their current size or current valuation? And if in the, if it's sort of like, well, you have to believe that this thing, this one thing goes really well, then you can build a …”

Kevin Weil Oct 7, 2022 ▶ 40:50 Kevin Weil: Lessons from Leading Product at Instagram & Twitter | 20VC #934 · 20VC with Harry Stebbings

Opinion

Weil: Ron Conway and Benchmark succeeded with opposite investing philosophies

“In the same way you can look at like what Ron Conway has done and what Benchmark has done. They've both been massively successful and their investing philosophies could not be more different.”

Kevin Weil Oct 7, 2022 ▶ 43:33 Kevin Weil: Lessons from Leading Product at Instagram & Twitter | 20VC #934 · 20VC with Harry Stebbings

Opinion

Weil: Peter Fenton, David Rosenblatt, and Carl Bass are top board members

“I'll give you three, actually. Peter Fenton, David Rosenblatt, and Carl Bass. Peter and David are on our board at Twitter. Carl's on the board at Planet. Because every single one of them, they are available whenever you need them. They're dedicated. They're ju…”

Kevin Weil Oct 7, 2022 ▶ 53:48 Kevin Weil: Lessons from Leading Product at Instagram & Twitter | 20VC #934 · 20VC with Harry Stebbings

Insight

Weil: Ask references what peers say to surface candidate weaknesses

“People are hesitant to say themselves necessarily to say something, you know constructive or negative about a person. But if you say like, you know, what are their peers say about them? Everyone can say, oh, their peers say.”

Kevin Weil Oct 7, 2022 ▶ 35:21 Kevin Weil: Lessons from Leading Product at Instagram & Twitter | 20VC #934 · 20VC with Harry Stebbings

The other half of the tape: Kevin Weil's own voice is left out of every number here. Other people bring the name up 9 times in 5 episodes on 20VC. every mention, with the transcript →

Who brings them up most Harry Stebbings 4 David Lieb 3 Todd Jackson 1 Jag Duggal 1