Serial Entrepreneur. Investor. Trustee @WhitneyMuseum, Former Entrepreneur-in-Residence @HarvardHBS. 🇺🇸🇵🇷🇪🇨

New York, USA
Joined November 2006
David Cancel retweeted
Olo turns 21 today. On 9.21.2006, @GMA and a young reporter named @DavidMuir, now anchor of @ABCWorldNews, broke the story by delivering text-ordered coffees to the anchor desk of @DianeSawyer and @RobinRoberts. Six million viewers for six-person @Olo. What a ride! 🚀
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David Cancel retweeted
Dan Wolchonok
@danwolchMar 31
Today's meeting tools give you a transcript, but nobody tells you how you did. I'm so excited to announce Work Coach (a new mac meetings app). Work Coach helps you by: - Observing you in meetings (interviews, 1:1s, sales calls, team meetings) - Analyzing how you show up to those meetings - Identifying opportunities to improve - Replaying the exact moments from your meetings where it happened - Role play conversations (intros in an interview, asking for a raise, etc) - Interviewing your coworkers to get feedback that you're not getting I'll put the download link below.
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David Cancel retweeted
2025 had the lowest rate of - mass shootings since 2006 - homicides since 1950s - teenage pregnancy in recorded history - suicides since 2020 - road fatalities since 2019 - drug overdose deaths since 2019 - alcohol consumption in recorded history - inflation since 2020
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David Cancel retweeted
We just raised $20M (Menlo, Sequoia, Felicis, Snowflake, Databricks) and launched Kai—the first superintelligent AI co-worker for customer success. It shouldn't take 100 people to serve 1,000 customers. Kai knows every customer, acts instantly, never drops the ball. Agency.inc fortune.com/2025/11/12/elias…
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David Cancel retweeted
Most people have no idea what it actually takes to be a founder. They talk about vision, grit, or passion. Those words are props. What you really sign up for is a life where every decision feels like it costs something real. You will spend years being misunderstood. By your team, your family, even the people you hire to help you. You will fail in public and still need to keep the energy up in private. Every founder lives with the weight of knowing that you can do everything right and still get crushed by luck, timing, or somebody else’s mistake. Founders aren’t braver than anyone else. They just get used to uncertainty, then stop waiting for clarity. Most of your wins won’t feel like wins at all. The first revenue will be too small. The first team will outgrow you or leave. The first product that feels right will barely matter to the market. You will doubt yourself in private, sometimes every week. The founders who last figure out how to keep moving while the ground shifts underneath them. Most outsiders want the founder badge but none of the scars. They want the upside, not the drag. The hardest part is sticking around after every plan gets blown up and you have to rebuild with less optimism and more scar tissue. What makes it work isn’t relentless hustle or some mythical trait. It’s learning to make peace with constant discomfort, and then making decisions anyway. If you need constant reassurance, you’ll give up before the real work begins. If you want everyone to like you, you’ll never make the calls that matter. If you can’t handle months where nothing feels certain, this life will eat you alive. But if you can hold your own in chaos, get better at being wrong, and still want to show up and try again, you just might have a shot at building something that matters. That’s what it actually takes. And nobody cares until you make it work.
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David Cancel retweeted
Dear Founders, Take money off the table in the next round. Love, Brian.
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David Cancel retweeted
I often re-read @natfriedman's personal website (former Github CEO)
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David Cancel retweeted
If a few of you are up, would love for you to try an early alpha version of what I've been vibe coding on. A domain suggestion tool. agent.ai/agent/domain-sugges… Super-easy, you enter an idea/concept and it generates a list of domains and their prices (on the major marketplaces). Note: It takes about 30 seconds to run (it's putting the LLM through its paces).
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David Cancel retweeted
Buffett: "Who you associate with is enormously important. And don’t expect to make every decision right on that. But your life is going to progress in the general direction of the people you work with, admire, and befriend." Charlie Rose Interview 2009:
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David Cancel retweeted
Waiting for certainty is the fastest path to irrelevance.
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David Cancel retweeted
Starting today: if you’re building something important and need the best talent - join us. And if you’re among the best and looking for a new challenge… take our test! (And if you’re interested in games, puzzles, talent, etc, apply to help us build!) MeritFirst.US
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David Cancel retweeted
Complaining is not a strategy.
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David Cancel retweeted
Geniuses are busy. Sages are hard to find. Children are easily distracted. Books will be there for you. Night and day without complaint, and without judgment.
Spend your time in the company of geniuses, sages, children, and books. @naval
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Great entrepreneurs aren't born, they are forged in the fire of Mount Doom. Like a diamond, we are slowly crushed. By overwhelming people problems. Incentives misalignments. Terrible business models. Toxic employees. This happens for decades, until one day, we reach our final form. Our spidey sense becomes finely tuned and our mistakes become less disastrous. But if you become even remotely complacent, you're in for a treat. Every time you take a breath and think "ah, I've arrived!" reality will punch you in the face. Your business will get disrupted. The person you trusted to do a critical job will let you down. You'll miss something in a contract that costs you millions. Get sued by a patent troll. This is why they pay us the big bucks. After all, as my friend @jzbecker put it: "Entrepreneurship is the art of getting fucked over, then getting back on the horse, over and over again, forever."
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For Seed investors in 2024, only 2 Things Matter: (1) Survivability and (2) Optionality for ‘Infinite Outcome’…
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David Cancel retweeted
I got a new job 🚨 who dis?!?
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Marc Andreesen is on point 🎯 @pmarca
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David Cancel retweeted
Elon has shown us this week what the future looks like. Robovan and robotaxis, humanoid robotics, green parks instead of parking lots, tunnels, rockets that are fully reusable and chopstick shenanigans. All of it sci-fi, but greater, and here, and incredible.
Mechazilla has caught the Super Heavy booster!
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David Cancel retweeted
👇🏽
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David Cancel retweeted
Really good advice from a really good introvert.
Successful Introvert Is Not An Oxymoron Many years ago I used to believe that being an introvert was a weakness in the business world. I grew up in India in the 1980s and back then, it was assumed that business people were extroverts (though I hadn't really even heard of the word back then). Self-promotion felt uncomfortable. Networking events drained me. I worried that my quieter nature would hold me back. But what I have learned over the years: What if I reframed "self-promotion" as simply educating others about the work my team and I were doing? This lesson and shift in perspective changed everything. I've had some modest success (as the co-founder of @HubSpot). Here's how introverts can thrive in business: 1) Leverage writing skills for thoughtful communication 2) Use listening as a superpower in negotiations 3) Recharge strategically to maintain energy By embracing these strengths, I've seen introverts become some of the most impactful leaders and innovators. The key is authenticity. Don't try to be an extrovert. Lean into your natural abilities. Introverts: Your quiet power is needed in business and the world. How have you leveraged your introvert strengths in your career? --- Note: This post was drafted with agent .ai (my latest passion project) h/t to @lennysan for his episode with @debliu_
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