Steve Kerr says Roger Federer taught his Warriors team the secret to sustained success wasn’t outworking everyone, it was building a life around your craft you never want to escape from “I’ll tell you a great story about Roger Federer. We were playing in China with the Warriors in 2017. Roger was in Shanghai for the Masters tournament, so we invited him to come speak to the team.” “Draymond Green asked him, ‘How do you sustain success? How have you managed to win majors 20 years after you first won one?’ Everyone was expecting him to say, ‘I work harder than everybody,’ the will, all the clichés.” “Roger Federer says, ‘I get up every morning and I make breakfast for my kids. Then I take them to school and drop them off. Then I go practice tennis for about two hours, and I’ve figured out a really good routine where I don’t destroy my body, but I can get all the work in I need.” “‘Then I go have lunch with my wife. In the evening, we cook dinner together. The kids are all home from school. We ask them about school. There’s so much joy in the house. We put them to bed, and then I put my head on the pillow and go, “Man, that was just a great day.” And I’ve been doing that for 20 years.’” “And it was like, yes. That’s it. That’s the formula. That’s what leads to sustained success. He loves tennis. He loves his family. He loves life. It’s not outworking everybody and banging your head against the wall, ‘I’m going to be better than everybody.’ It’s allowing your natural talent to shine through with a work ethic, with a great family life, with perspective, with peace, with mindfulness.” “It’s perspective. It’s joy. It’s passion. It’s mindfulness. It’s an awareness that we are truly lucky. To get the most out of ourselves, it’s our daily rituals and experiences and love and joy.”

My conversation with @dougleone, partner at @sequoia. 0:00 How to Dominate for Decades 3:17 Turning Fear Into a Tailwind 5:40 Immigrant Drive, Hard Work & the Beach Club 12:19 Simplifying Life & Choosing Discomfort 14:37 The Homeless Sequoia Partner With No Plan B 16:49 Stepping Down, Coming Back & Starting Over 20:04 Why AI Is Different From Every Previous Technology Shift 22:13 Doug's Three Investment Heuristics 23:52 The Cost of Selling Great Companies Too Early 25:39 Helping Founders Turn Products Into Businesses 28:28 David Vélez, Nubank & the Psychology of Founder Support 32:25 Why Founders Must Remain the Soul of the Company 36:13 Torturing Yourself Into Greatness 39:57 Don Valentine, Succession & the Sequoia School of Hard Knocks 44:28 Staying Grounded & Developing a Sniffer for People 47:46 Hypercompetitive With a Heart of Gold 50:13 Fred Luddy, Israeli Founders & Radical Directness 52:28 Trust Is the Accelerant of Business 59:57 Starting From Zero & Hunting for the Next Great Founder 1:05:59 Architect Your Board Like Your Product 1:10:24 Truth, Disagreement & the Art of Difficult Feedback 1:13:43 Humanity, Introversion & the Value of Relationships 1:18:18 What Doug Learned From Michael Moritz Includes paid partnerships.

An underrated life decision is living very close to the people you love.

Today we reduced headcount by 22%. The business is the strongest it's ever been. So I think it's important to be direct about what I'm seeing and why. First, I made this decision and I own it. I did it because the way to operate at the highest level of productivity is changing, and to win the future, ClickUp needs to change with it. Second, this wasn't about cutting costs. Most savings from this change will flow directly back into the people who stay. We'll be introducing million-dollar salary bands. If you create outsized impact using AI, you'll be paid outside of traditional bands. Most importantly, I have the deepest gratitude for those affected. We're doing this from a position of strength specifically so we can take care of people properly. Everyone affected receives a package aimed at honoring their contributions and easing the transition. I only see two options: wait for this to play out gradually in the market or be honest about what I'm seeing and act proactively. THE 100X ORGANIZATION The primary change is that we're restructuring around what I call 100x org. The goal is 100x output. The roles required to build at the highest level are fundamentally different than they were a year ago. Incremental improvements to existing systems won't get us there. We need new ones. That means creating enough disruption to rebuild rather than iterate on what's already broken. The common narrative is that AI makes everyone more productive. It doesn't. Many of the workflows of today, if left unchanged, create bottlenecks in AI systems. These roles will evolve. But waiting for that to happen naturally means falling behind now. The 100x org is actually heavily dependent on people - infinitely more than today. This is only possible with 10x people that have embraced and adopted new ways of working. THE BUILDERS, AGENT MANAGERS, AND FRONT-LINERS — THE BUILDERS: 10X ENGINEERS I don't think most companies have internalized what's actually happening with AI in engineering. The common narrative is that AI makes all engineers more productive. That may be true in isolation, but at an organization level - that is the farthest thing from reality. Here's what we've validated recently at ClickUp: the great engineers, the ones who can orchestrate, architect, and review, are becoming 100x engineers. They're not writing code. They're directing agents that write code. The skill is judgment. AI makes the best engineers wildly more productive, and everyone else using AI slows these engineers down. Think about it - the bottlenecks are (1) orchestration - telling AI what to do, and (2) reviewing - what AI did. Everything is leapfrogged and no longer needed. So who do you want orchestrating and reviewing code? And how do you want your best engineers to spend their time? If your best engineers are spending time reviewing other people's code, then this is inherently an inefficient bottleneck. These engineers can review their agent's code much faster than reviewing human code. The new world is about enabling your 10x engineers to become 100x. The wrong strategy is to push every engineer to use infinite tokens. Companies doing this are celebrating 500% more pull requests. But customer outcomes don't match the volume of code being generated. I call this the great reckoning of AI coding, and every company will face this soon if not already. More code is just another bottleneck to the best engineers, and ultimately to your company's impact as well. — THE BUILDERS: 10X PRODUCT MANAGERS Product management and design roles are merging. Designers that have customer focus, become more like product managers. And product managers that have intuition for UX become more like designers. The bottleneck of user research is gone. It takes us just one mention of an agent to kickoff research and analyze results. The bottleneck of product <> design iteration is also gone. The product builder iterates on their own, along with agents and skills that ensure alignment with quality and strategy. Also controversial today - I believe that the wrong strategy is to have your PMs shipping code - that just introduces another bottleneck that the best engineers will waste their time on. To be clear, PMs should be coding but they should do this in a playground to iterate, validate, and scope. That code should not go to production. Everything outside of managing systems, orchestrating AI, and reviewing output becomes a bottleneck. That's why the other roles that are critical along with these are the systems managers (to reduce bottlenecks) along with a bottleneck you can't replace - customer meeting time. — THE SYSTEM MANAGERS Ironically, the people that automate their jobs with AI will always have a job. They become owners of the AI systems - agent managers. We have many examples of these people at ClickUp. The underlying systems in which we operate are absolutely critical to get right. I think most companies are delusional to think they can iterate on existing systems and compete in this new world. You must create enough disruption so that old systems are deprecated entirely. If there's any definition for 'AI native' that's what it is. — THE FRONT-LINERS In a world that will become saturated with AI communication, the human touch will matter more than anything to customers. This is a bottleneck that you shouldn't replace - even when agents are high enough quality to do video meetings. One-on-one meeting time with customers is something that shouldn't be automated. The systems around the meetings should be - so that front-liners spend nearly 100% of their time with customers. REWARDING 100X IMPACT In a world where companies are able to do so much more with less, where does that excess money go? In our case, much of the savings in this new operating model will flow directly back to those that enabled it. We must reward people that create productivity accordingly. This aligns incentives on both sides. Plus, in a world where your best people create 100x impact, you can't afford to lose them. You should aim to retain these employees for decades. The context they have and their ability to efficiently orchestrate and review will be nearly impossible to replace. Compensation bands of today should be thrown out the door. We're introducing $1 million cash/year salary bands with a path available to nearly everyone in the company if they produce 100x impact by creating or managing AI systems. THE FUTURE Nearly every company will make changes like these. The ones that do it proactively will define what comes next. The future is not fewer people. It's different work, new roles, and better rewards for those who embrace it. We're already seeing entirely new roles emerge, like Agent Managers, that didn't exist a year ago. ClickUp is positioning to lead this shift, not just internally, but for our customers too. I've never been more certain about where we're headed.