Attracted to complex problems... Cofounder & CTO @SensCy, Former Cyber Command & Intel, USMC Vet, Poker Player, Stock Trader, EV=Expected Value

Joined August 2013
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Pinned Tweet
1 Jan 2022
How To Build a Great Team —a thread (1) Articulate the mission: express where you are taking them and why it matters.
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Last night my son broke the 13-14 State Record in the 50 Long Course Butterfly. It was a surreal moment. Swim training is tough - 3 hour practices 6 days a week - so proud of him.
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This is an important read.
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.
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This is worth your time.
My conversation with Marc Andreessen (@pmarca), co-founder of @a16z and Netscape. 0:00 Caffeine Heart Scare 0:56 Zero Introspection Mindset 3:24 Psychedelics and Founders 4:54 Motivation Beyond Happiness 7:18 Tech as Progress Engine 10:27 Founders Versus Managers 20:01 HP Intel Founder Legacy 21:32 Why Start the Firm 24:14 Venture Barbell Theory 28:57 JP Morgan Boutique Banking 30:02 Religion Split Wall Street 30:41 Barbell of Banking 31:42 Allen & Company Model 33:16 Planning the VC Firm 33:45 CAA Playbook Lessons 36:49 First Principles vs. Status Quo 39:03 Scaling Venture Capital 40:37 Private Equity and Mad Men 42:52 Valley Shifts to Full Stack 45:59 Meeting Jim Clark 48:53 Founder vs. Manager at SGI 54:20 Recruiting Dinner Story 56:58 Starting the Next Company 57:57 Nintendo Online Gamble 58:33 Building Mosaic Browser 59:45 NSFnet Commercial Ban 1:01:28 Eternal September Shift 1:03:11 Spam and Web Controversy 1:04:49 Mosaic Tech Support Flood 1:07:49 Netscape Business Model 1:09:05 Early Internet Skepticism 1:11:15 Moral Panic Pattern 1:13:08 Bicycle Face Story 1:14:48 Music Panic Examples 1:18:12 Lessons from Jim Clark 1:19:36 Clark Versus Barksdale 1:21:22 Tesla Versus Edison 1:23:00 Edison Digression Setup 1:23:13 AI Forecasting Myths 1:23:43 Edison Phonograph Lesson 1:25:11 Netscape Two Jims 1:29:11 Bottling Innovation 1:31:44 Elon Management Code 1:32:24 IBM Big Gray Cloud 1:37:12 Engineer First Truth 1:38:28 Bottlenecks and Speed 1:42:46 Milli Elon Metric 1:47:20 Starlink Side Project 1:49:10 Closing Includes paid partnerships.
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Dave Kelly retweeted
U.S. President Donald Trump is threatening to block the opening of the Gordie Howe International Bridge, which he had endorsed in 2017 during his first term. Former Michigan Governor Rick Snyder helped broker the deal with Canada to build the bridge. @VassyKapelos asked him if he was surprised by Trump's change in position. #cdnpoli #ctvpp More: ctvnews.ca/video/shows/power…
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3 Aug 2025
This is crazy! Wow!
Facebook once bought a VPN app for $120M and turned it into a surveillance tool that spied on 33M users' entire phones for years. This app helped Zuck buy WhatsApp for a whopping $19B and break Snapchat's encryption. Thread
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Dave Kelly retweeted
As a physician and a swimming coach, I feel the need to chime in here. All of the known performance enhancing drugs which (by definition) are known to be effective, and when taken in significantly high enough quantities, are also known to be unsafe. We cannot rely on the swimmers who use these drugs, nor their coaches, to accurately monitor the quantities of drugs being taken nor the adverse effects on their health the drugs may be causing. With the Enhanced Games, a swimmer's speed is taking a higher priority over the athlete's safety. At The Race Club, we believe that the safety and well-being of the athlete should take the highest priority. We learned from training 52 Olympic swimmers that excellent nutrition and taking safe, approved supplements in recommended doses can help the athlete's performances . We condemn the use of illegal PED's. Today, at The Race Club, we teach mostly 8-18 year old swimmers to get faster and, more importantly, to become better people. We teach all five disciplines of swimming: fundamental technique, dryland, nutrition, recovery and mental training. The Enhanced Games goes against everything we teach. Imagine how the suggestible mind of a young 10 year old swimmer, dreaming to become the fastest swimmer possible, will be influenced by the Enhanced Games. Shame on those involved with these Games. Yes, at the World Aquatic and Olympic Games competitions, sadly, cheating does occur. The solution to that problem is not to create an Enhanced Games, putting athletes at unnecessary risk. The solution lies in doing a better job of identifying the cheaters and having them, and those involved with them, suffer significant consequences for doing so. Gary Hall, M.D. @enhanced_games@Olympics
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Dave Kelly retweeted
22 May 2025
WSJ on Jony Ive and Sam Altman’s OpenAI device: • The product will be capable of being fully aware of a user's surroundings and life, will be unobtrusive, able to rest in one's pocket or on one's desk, and will be a third core device a person would put on a desk after a MacBook Pro and an iPhone. • The Journal earlier reported that the device won't be a phone, and that Ive and Altman's intent is to help wean users from screens. • Altman said that the device isn't a pair of glasses, and that Ive had been skeptical about building something to wear on the body. via: wsj.com/tech/ai/what-sam-alt…
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17 Apr 2025
RT @JamesClear: Don't let the hope of finding a better way prevent you from starting down the best path you know of right now. This day won…
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17 Apr 2025
This is great advice. For most of us, it took a lifetime to learn!
17 Apr 2025
Most founders I mentor are overwhelmed, unfocused, and on the verge of burnout. I sat down with two founders in Bali who reminded me of myself 14 years ago. Here’s the advice I gave them (that I wish I knew in my 20s):
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16 Apr 2025
This injects catastrophic cybersecurity risk to all businesses. Here’s why: The CVE (Common Vulnerabilities and Exposures) is the backbone of the entire vulnerability ecosystem. It’s the notification process that tells us which software / firmware / hardware we own that has a security flaw exploited by cyber criminals. It also tells us how to close the vulnerability. Without this system in place, every business will have major blind spots in thier cybersecurity posture and be at significantly greater risk of suffering a cyberattack.
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Dave Kelly retweeted
13 Apr 2025
if you are interested in infrastructure and very large-scale computing systems, the scale of what’s happening at openai right now is insane and we have very hard/interesting challenges. please consider joining us! we could desperately use your help.
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12 Apr 2025
C’Mon April, start Apriling!
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10 Apr 2025
These tweets seem to never age well.
3 Apr 2025
Not a time to buy the dip.
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4 Apr 2025
If you want to go off the grid, change your name to Null.
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3 Apr 2025
Not a time to buy the dip.
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2 Apr 2025
Next time you think you need that Google job to be someone, always know that the ultimate status would be forcing Google to buy your company (or displacing them all together).
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Dave Kelly retweeted
you someone @X can we help long time user @alphatrends get back his account that was hacked today now just crypto phishing scam pinned
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31 Mar 2025
Not too bad considering all the uncertainty.
31 Mar 2025
And just like that, Q1 is officially over! 🎉 We survived (barely)... The S&P 500 declined by 5%, marking its worst quarterly performance since Q3 2022 📉
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31 Mar 2025
My son’s generation are digital indigenous people.
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Dave Kelly retweeted
30 Mar 2025
The big insurance companies and the PBMs they own, create almost all of the complications. They are able to do so because they control the flow of patients for hospitals/providers and drug manufacturers. They are the gatekeepers for trillions of dollars of healthcare spending. Everyone has to kiss their ass and accept the complications. They do this via their control of networks of providers and drug formularies. That's it. It's a simplification. But if we End their control of networks and formularies , healthcare can be transparent and affordable. Then the only question becomes how do patients that can't afford their care pay for it Answer: We use the trillions we just saved to help them.
30 Mar 2025
Healthcare is a very simple business. We go to the Dr. The Dr tell us what we need (if anything). The ONLY questions are: 1. What does it cost 2. How will the patient pay for it Everything else is a complication. Unfortunately, those complications have removed all alignment between patients and the economics of healthcare
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