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Agrawal: Twitter planned 20-25% headcount cut just before Musk acquisition
“Like one weird anecdote that I think out there, but not understood is that the three days after we signed the deal to sell the company, which was a Monday, Thursday was a earnings call. And there was a whole plan to really Like trim the company down by about 2…”
Parag Agrawal Aug 14, 2025 ▶ 12:04 Twitter's former CEO on rebuilding the web for AI | Parag Agrawal (Co-founder and CEO of Parallel)
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Cramer: Sentry targets every customer of rival startups reaching $10M ARR
“If you get, I don't know, say your ten million in revenue, we will come after every logo you have. We haven't done it that much, but we have gone after two companies, and they basically don't exist anymore.”
David Cramer Jun 19, 2025 ▶ 1:38:01 How rejecting conventional wisdom grew Sentry to a $3 billion company | David Cramer (Co-founder)
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McCabe: Intercom stack ranks all employees quarterly using an algebraic score
“The manager simply rates the employee's performance against their goals for the quarter, because we set goals every quarter, and their behavior against each value from one to five. Plugs that into a little form. Some very basic algebra is done. Spits out a num…”
Eoghan McCabe Sep 5, 2024 ▶ 20:09 Rebooting Intercom: Eoghan McCabe on Defying Silicon Valley Orthodoxy | Co-founder & CEO
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McCabe: Intercom enforces quarterly bottom-tier quotas with fast-track termination PIPs
“So imagine two percent of people got the bottom rating, but I, my, by my own appraisal, look around the organization and say, this is not good enough. I want three, four, five percent of people to get the bottom rating. Then you're very prescriptive about what…”
Eoghan McCabe Sep 5, 2024 ▶ 20:50 Rebooting Intercom: Eoghan McCabe on Defying Silicon Valley Orthodoxy | Co-founder & CEO
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McCabe: Cut Intercom headcount by 27% and removed most HR upon return
“When I went back, I decreased the size of the company by 27%. Got rid of most of HR. Got rid of most of our policies and practices and all the grown-up stuff.”
Eoghan McCabe Sep 5, 2024 ▶ 37:08 Rebooting Intercom: Eoghan McCabe on Defying Silicon Valley Orthodoxy | Co-founder & CEO
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Sager: Plaid intentionally avoids running at 100% capacity to preserve agility
“Hey, I really don't ever want to be at like right at a hundred percent capacity. I'm willing to pay for some inefficiency so that as the market evolves, as our product evolves, et cetera, like I have the capacity to kind of adjust to it in real time, much more…”
Eric Sager Jul 16, 2026 ▶ 25:23 Why great leaders make themselves obsolete | Eric Sager (COO, Plaid)
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Copplestone: Supabase compensates sales reps strictly on incremental usage uplift
“Yeah, on the incremental uplift only, which I think is the big difference from what was traditionally done. You know, on a PLG motion, you could easily say, ah, get a salesperson and so on, like, reach out to anyone and then you pay them on, on the revenue gen…”
Paul Copplestone Jun 25, 2026 ▶ 51:02 The egoless culture that built Supabase | Paul Copplestone (Co-founder, CEO)
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Shiebler: Artemis evaluates all technical architecture by AI coding tool accuracy
“When we make architectural decisions, the first question that we ask is, is this an architectural decision that will increase or decrease the capability of AI tools to have the, to make the right answers?”
Dan Shiebler Apr 21, 2026 ▶ 19:52 Inside Artemis' "AI vs AI" war | Shachar Hirshberg & Dan Shiebler (Co-founders, Artemis)
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Hirshberg: Every Artemis engineer runs four to eight parallel cloud coding instances
“So today everyone is basically having like, let's say four to eight cloud code instances running in parallel, building the system, working on shipping four to five features simultaneously.”
Shachar Hirshberg Apr 21, 2026 ▶ 21:32 Inside Artemis' "AI vs AI" war | Shachar Hirshberg & Dan Shiebler (Co-founders, Artemis)
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Kreps: Confluent relegated its core cash-cow product to engineers' spare time
“Originally it was like a small group that was working on the cloud offering. And then we were like, no, okay, everybody. Only does the cloud thing, and we will work on the software product in our spare time. Team by team, which is a very dangerous thing to do,…”
Jay Kreps Mar 26, 2026 ▶ 52:21 How to build a company when you’re not an optimist | Jay Kreps (Co-founder and CEO, Confluent)
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Board misalignment over long-term vision was a factor in selling AppDynamics
“But if I have investors who don't want to do that for the longterm, we want to do in something different vision for what the company should be. Then you're kind of misaligned and that creates a big execution and uncertainty and risk. Unfortunately, we had thos…”
Jyoti Bansal Nov 19, 2025 ▶ 39:05 How Harness runs 16 “startups within a startup” at scale | Jyoti Bansal (Co-founder and CEO)
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Kanter: Stedi gives identical support to $500/month and seven-figure clients
“We don't have a different support program, any internal designation for support between customers who pay us seven figures per year and customers who pay us 500 dollars a month. This is the exact same support.”
Zack Kanter Nov 6, 2025 ▶ 1:10:37 How to build a company you’ll run forever | Zack Kanter (Founder and CEO of Stedi)
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ClassDojo mandates that over half its workforce must be former founders
“We basically just had the mandate. We're like, look, we're like more than half the company is going to be founders. I think it was more than two thirds at some point, but it's like, I'm one half is going to be founders or founding team members.”
Sam Chaudhary Sep 3, 2025 ▶ 1:09:32 Starting an education giant in a “bad market” | ClassDojo’s story | Sam Chaudhary (Co-founder & CEO)
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A lead investor attempted to halve Canva's valuation on signing day
“It was all rosy until the final day when they had to sign the long docs, everyone else had signed, everyone else had put in money. And this investor came back to us and said, you know what? We think we overvalued you. We think we can get better deal. How about…”
Cameron Adams Aug 20, 2025 ▶ 1:00:48 How Canva leveraged unconventional growth levers to grow to $42B | Cameron Adams (Co-founder & CPO)
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Younis: Applied Intuition's culture is closer to Elon's X than Google
“On the spectrum of like Google to, you know, working for Elon at X, like we're more on the Elon X. I don't, we're not anywhere near there, but we're more towards that than being like Google.”
Qasar Younis Aug 1, 2025 ▶ 40:48 Inside the ex-YC partner’s $15B self driving car company | Qasar Younis
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Braintrust built a terrible go-to-market motion to test product strength
“I wanted at Braintrust to, again, in the spirit of skepticism, Build a terrible go-to-market motion early on, but make the product, make Braintrust only successful if the product was so good that despite being grossly incompetent at selling and marketing our p…”
Ankur Goyal Jul 24, 2025 ▶ 29:30 What Braintrust got right about product-market fit | Ankur Goyal (Founder and CEO)
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Cramer: Sentry refused Uber's lucrative enterprise contract to avoid on-premise software
“Uber actually did pay for a year for a support contract. And it was a lot of money. It was a big, big contract for us. And we did, we chose to not renew it. And I'm like, I don't want to be in that business. I don't want to sell on-prem software. I don't want …”
David Cramer Jun 19, 2025 ▶ 38:49 How rejecting conventional wisdom grew Sentry to a $3 billion company | David Cramer (Co-founder)
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Cramer: Tracking startup adoption matters more than daily revenue or sales forecasts
“I actually, I could not tell you any of the day of the week, how much money we make. I can give you rough ballpark numbers of how many customers we have, and if we are growing net customers or not, and I can probably tell you we're probably missing sales forec…”
David Cramer Jun 19, 2025 ▶ 1:13:58 How rejecting conventional wisdom grew Sentry to a $3 billion company | David Cramer (Co-founder)
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Busque: 100% of Guideline's 401(k) plans require automatic enrollment
“Today. A hundred percent of our plans are auto enrolled. So we don't have anybody that's opted out. If you don't want auto enrollment, you don't get a guideline plan.”
Kevin Busque Feb 20, 2025 ▶ 48:32 Inside Guideline's mission to modernize 401(k)s | Kevin Busque (Co-founder and CEO)
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Clay combines AE, SDR, and sales engineer into one GTM engineering role
“We do sales through this, you know, we call it go-to-market engineering. And so this is collapsing three different roles into one. An AE, an SDR, and a sales engineer all into one role. And this is a person who's a bit more technical and background, who is goo…”
Varun Anand Jan 23, 2025 ▶ 45:14 Clay's unconventional path to $1.25B: Rethinking GTM, pricing, and enterprise sales | Varun Anand
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Handy: dbt Labs replaced its entire executive leadership team over 18 months
“The initial leadership team that I had grown the business with scaled for a long way, but over the past 18 months, I've replaced every single person that reports to me with like the folks that can scale to the Next level.”
Tristan Handy Dec 19, 2024 ▶ 39:24 Building a $4B data platform: Inside dbt Labs' unconventional path | Tristan Handy (Founder & CEO)
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Moore: Early on, Crossbeam refused product demos unless two partner companies attended
“We didn't do product demos or sales calls. Unless two companies were on them at the same time.”
Bob Moore Sep 19, 2024 ▶ 1:00:50 How to find — and keep — product-market fit | Bob Moore (Crossbeam, RJMetrics, Stitch Data)
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McCabe: Intercom eliminated peer and self-reviews for formulaic values-based evaluation
“When I went back to Intercom, I found a culture I didn't like. And I ripped up the old values, wrote new values. And rather than these values be motivational posters, and I did specifically design them tongue-in-cheek as motivational posters I made them execut…”
Eoghan McCabe Sep 5, 2024 ▶ 19:22 Rebooting Intercom: Eoghan McCabe on Defying Silicon Valley Orthodoxy | Co-founder & CEO
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MacInnis: All teams at Rippling are deliberately kept understaffed
“All of our teams at Rippling are pretty deliberately understaffed and people feel it and they'll complain about resourcing, but like at the end of the day, a team of five that ought to be seven is way better than a team of nine or 10 that ought to be seven.”
Matt MacInnis Apr 25, 2024 ▶ 17:18 How to be effective up and down the org chart | Matt MacInnis (Rippling, Inkling, Apple)
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MacInnis: Parker Conrad approves every Rippling expense over $5
“Parker still approves every expense over five dollars personally. He still runs payroll for the whole company globally in our product.”
Matt MacInnis Apr 25, 2024 ▶ 24:45 How to be effective up and down the org chart | Matt MacInnis (Rippling, Inkling, Apple)
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Amin: Clay drove growth by forcing all customer support into public Slack
“Eventually the way that we got a ton of customers was actually by cutting off all of the different ways that we supported customers. So we basically pushed all of our customers into the same channel. So anyone that would sign up to Clay, we would say, join our…”
Kareem Amin Jan 18, 2024 ▶ 30:06 A product-market-fit masterclass | Kareem Amin (Clay)
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Narkhede: Confluent chose not to separate on-prem and cloud sales teams
“We actually decided to not split it. And that was because we ultimately wanted to transition to a cloud first business. So we put in a, instead a lot of thought and a lot of investment in sales enablement you know, internal education of why this is important, …”
Neha Narkhede Dec 8, 2023 ▶ 39:08 Winning with open and closed source products | Neha Narkhede (Co-founder at Confluent and Oscilar)
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Zima: Looker deprioritized app crashes for two years to build features
“Whereas like I had to go to the support team over and over again for probably a period of two years and say the app crashing is not a priority right now because I want to do more feature work and we can suffer through this and I know it's bad, but I don't thin…”
Colin Zima Oct 12, 2023 ▶ 37:41 How to leverage intuition, customer support, and raw effort | Colin Zima (Omni & Looker)
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Siroker: Rewind published its unredacted investor pitch deck and video on Twitter
“That's why I announced and shared our investor deck unredacted. I didn't hide any numbers. You know, you can find it on Twitter, you know, seven minute pitch you know, millions of people have seen it.”
Dan Siroker Sep 14, 2023 ▶ 52:00 AI Hot Takes and Unusual Twitter Fundraising Strategies with Dan Siroker (Rewind AI)
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Parikh pushed Zuckerberg to prioritize engineering efficiency over pure product features
“You know, I remember talking to Mark and Mark was like, yeah, we can, you know, we have money, so we should just build features and we should put all the engineers working on product. And I said, cool, but I'm going to work on efficiency because I'm not going …”
Jay Parikh Aug 27, 2026 ▶ 1:02:57 The most expensive mistake in outsourcing your tech stack | Jay Parikh (EVP CoreAI, Microsoft)
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Noronha: Gamma rejected the standard vertical SaaS playbook despite investor pushback
“We bet early on and pretty consistently on building a horizontal product rather than a vertical one that was focused on a specific persona, and it was actually a source of constant tension in fundraising and a lot of our early debates because I think there's s…”
Jon Noronha Jul 24, 2026 ▶ 9:50 How Gamma pulled off their AI pivot | Jon Noronha (Co-founder and CPO of Gamma)
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Sager: Plaid will accept account unprofitability to ensure customer success
“There's just, there's almost no amount of money, right, that I wouldn't reasonably spend to make sure that one of our customers gets to a good outcome. And even if that makes that account unprofitable, That experience will kind of resonate across the rest of t…”
Eric Sager Jul 16, 2026 ▶ 34:29 Why great leaders make themselves obsolete | Eric Sager (COO, Plaid)
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Moreno deterred Windsurf executive conflicts by intentionally annoying both parties
“One of the things I used to say at Windsurf, and we haven't had to do this yet at Parallel, But I would say I don't ever want a debate or a conflict between my directs to come to me, because if it does, I will intentionally make a decision that's designed to a…”
Graham Moreno May 21, 2026 ▶ 33:55 Why old-school sales work still wins in the AI era | Graham Moreno (Head of GTM, Parallel)
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Xero built and shuttered an experimental AI chat-based accounting app
“So for example, we took a bet where we said, and I did this, I'm like, I don't want to wake up in two years and find out that the entire App is agents in a chat. So we're going to go off and build our own app on the side. That is where you're going to do accou…”
Diya Jolly Apr 30, 2026 ▶ 27:20 AI killed the product roadmap | Diya Jolly (CPO & CTO of Xero)
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Jolly secretly called in sick as a director to protect thinking time
“When I was a director, I literally would call in sick to get my thinking time once in a while, because I'm like, I just like, there's like, and I would tell my manager, I'm doing this because you'll respect the fact that I'm, I need to get stuff done, and I ne…”
Diya Jolly Apr 30, 2026 ▶ 54:06 AI killed the product roadmap | Diya Jolly (CPO & CTO of Xero)
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Chris Degnan historically disliked hiring enterprise sales reps who came from Oracle
“I didn't traditionally, you came from Oracle and I didn't, I don't, I didn't traditionally like hiring Oracle people.”
Chris Degnan Feb 26, 2026 ▶ 41:31 Snowflake’s first sales hire on scaling from $0 to $3.5B | Chris Degnan (Former CRO, Snowflake)
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Grosser: Vercel deployed AI lead qualification agents matching human SDR performance
“I launched a GTM engineering team in the first six weeks on the job at Vercel. So basically, we took Three sales engineers were like, congrats, you're now founding members of our GTM Eng team, where we're gonna go bring agents to bear across everything in GTM.…”
Jeanne DeWitt Grosser Feb 5, 2026 ▶ 33:14 Executive Function: Build systems that can decide without you | Jeanne DeWitt Grosser (COO, Vercel)
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Grosser: Stripe executives donated headcount across P&Ls to self-solve budgets
“Stripe got much, much, much more rigorous about the budget is the budget, like, the, we've got headcount OpEx, and, like, that will be the number that we have collectively as a company. And across the course of the year, opportunities would emerge that you wou…”
Jeanne DeWitt Grosser Feb 5, 2026 ▶ 43:22 Executive Function: Build systems that can decide without you | Jeanne DeWitt Grosser (COO, Vercel)
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Varanasi: Meter focuses on a 25-year horizon rather than five-year goals
“I don't care about Where meter ends up in five. I care about where it ends up in 25. But at the same time, the next few hours also really matter to me.”
Anil Varanasi Dec 10, 2025 ▶ 2:54 Building Meter for decades, not an exit | Anil Varanasi (Co-founder and CEO)
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Varanasi: Meter plans to develop proprietary ASICs and custom chips
“Over time, we can go even further down the stack where we should go make our own ASICs, our own chips.”
Anil Varanasi Dec 10, 2025 ▶ 5:17 Building Meter for decades, not an exit | Anil Varanasi (Co-founder and CEO)
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Varanasi: Meter's in-house chip plans will take eight years to yield
“Yeah, we have plans underway. We think we can do some great work there, but by the time we realize that it will take another eight years, I think from now before this will even be fruitful at all.”
Anil Varanasi Dec 10, 2025 ▶ 32:21 Building Meter for decades, not an exit | Anil Varanasi (Co-founder and CEO)
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Meter aims to decouple management from decision-making authority
“And one of the things we're trying to do, and I don't know how successful we will be over the next five to seven years is, the other thing we disagree with in this vein, somehow people have bundled management and authority together in one. We're trying to deco…”
Anil Varanasi Dec 10, 2025 ▶ 56:15 Building Meter for decades, not an exit | Anil Varanasi (Co-founder and CEO)
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Anil Varanasi talks to his 24 direct reports every few days
“All the two dozen I talk to at least every two, three days.”
Anil Varanasi Dec 10, 2025 ▶ 1:01:59 Building Meter for decades, not an exit | Anil Varanasi (Co-founder and CEO)
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AppDynamics fired Netflix as a customer to protect its engineering capacity
“Some point in time, and that was the hardest decision I probably ever made, we decided to lose them. They were so much bigger than our customer number, you know, like they were customer number one in terms of their size, and our customer number two to 20 combi…”
Jyoti Bansal Nov 19, 2025 ▶ 7:58 How Harness runs 16 “startups within a startup” at scale | Jyoti Bansal (Co-founder and CEO)
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Harness completely rewrites all acquired startup codebases within six months
“Whenever we acquire a small company, we rewrite the code completely in six months to on our platform. So the, all the old code goes away on our platform.”
Jyoti Bansal Nov 19, 2025 ▶ 58:48 How Harness runs 16 “startups within a startup” at scale | Jyoti Bansal (Co-founder and CEO)
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Stedi threw away its entire codebase roughly eight times before public launch
“It took four and a half years for us to launch anything publicly. And what you don't see during that time was that we threw away everything that we had built completely, every line of code, maybe eight times.”
Zack Kanter Nov 6, 2025 ▶ 30:11 How to build a company you’ll run forever | Zack Kanter (Founder and CEO of Stedi)
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Kanter: Stedi de-scopes features until they are barely usable by one customer
“If the, if there is the option to ship things Incrementally. It is, I think, virtually always better. And that's how we ship things now. Like we ship, we don't ship big bang features. In fact, like we de-scope features to the point of where we're, where we thi…”
Zack Kanter Nov 6, 2025 ▶ 49:49 How to build a company you’ll run forever | Zack Kanter (Founder and CEO of Stedi)
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Kanter: Stedi tells new hires on day one that everything is their fault
“On everybody's first day at Steady, I say, welcome to Steady, everything's your fault now. And then I say it's not as bad as it sounds, actually, everything's your fault now also. You know, everything's your fault, and your manager's fault, and everything kind…”
Zack Kanter Nov 6, 2025 ▶ 1:01:47 How to build a company you’ll run forever | Zack Kanter (Founder and CEO of Stedi)
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