Building RUVs and more for startups @rollupshq. Small angel investor. Dad. Prev: 2x founder and prior Special Forces medic (18-D).

Joined December 2014
292 Photos and videos
You keep your seat at the table by creating more successes, not tapping the sign of your previous ones.
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I see AI is being intro'd to a very SOF problem: having to tell your own coworkers to get the F out of the room because the next part is NOFORN.
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How to ragebait a VC - Which podcast gave you that opinion? - How would you add value if you found a way to be valuable? - You look like you make all of the 2 but none of the 20. - Sorry, we aren't raising from you right now. - Which AI model did you use to vibe code your firm's website? - What startup role would you take if they'd have you?
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Founder hack: form a startup as an LLC first, then convert to a C‑corp once the LLC is worth several million (but under the QSBS $75M cap) so that the higher fair market value becomes your “basis” for QSBS and you can exclude up to 10x that amount from federal tax on exit, potentially turning hundreds of millions of gain into 0%-tax QSBS instead of being limited to the flat $10–15M cap. You're welcome have a good weekend.
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Look at that subtle off-white coloring. The tasteful thickness of it. Oh my God, it even has an animated mesh background. Very nice,@tryramp.
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Anthropic was right. The secondary trading platforms are part of the problem. Here's an example from one platform: 1. "structured via a forward contract, the standard approach given the company's transfer restrictions". 2. rounded share count to disguise seller ID, presumably from the company
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Most AI agents are throatless. A throatless agent is one you can’t choke when it messes up. It just says: “sorry, LLMs make mistakes 🤷” That works for low-stakes tasks. Not for high-stakes ones. Startups don’t love paying law firms $500/hr to click around in Carta to update their cap table, a task easily done by AI agents today. But they still do it bc they’re not just buying labor. They’re buying accountability, a throat to choke when a multimillion dollar cap table mistake happens. If the cap table is wrong and it blows up later, the law firm shares the risk. AI agents don’t. For AI to win high-stakes workflows, it’s not just about making the harness/ouput better. The agent itself also has to stand behind its output. Not “heads up, this might be wrong.” More like: “this is correct, and if it’s not, we’ve got you covered.” They’ll have a throat to choke. And it'll be worth it bc these are the high value workflows. If you’re building in this direction, I’m writing angel checks.
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There's this AI agent startup that automates company operations. Their biggest blocker to growth has been showing potential customers just how powerful their solution is. Like the "Alexa problem" - you stare at the little device, and you don't know what it can do, so you just ask it about the weather repeatedly. To overcome the blocker, they have started launching entire startups that sell real products online, generate real revenue, and real customer support emails. And then they automate it all. Their first startup is currently selling a CPG good online, without much human involvement at all. Their revenue growth rate is back on track since they started showcasing their automated startups to potential customers. The whole pitch is now "be like this startup." I think we'll see more of this.
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Yep
We just raised $4.3M from @generalcatalyst with participation from @gokulr, @toddgoldberg, @rahulvohra, @aarthir to build an AI-native consumer brands company that owns, launches and operates brands end-to-end. Consumer brands are still built with fragmented teams, slow feedback loops, and manual workflows. We’re replacing that with a unified stack of AI agents that owns and operates our brands. We’re building the AI-native Procter & Gamble - powered by agents, not org charts. If you want to solve hard agentic problems and move atoms at the speed of bits, come join us. It’ll be fun!
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Anthropic $30B ARR Slack acquired for $27B DO YOU KNOW HOW MUCH COOLER SLACK WOULD BE IF ANTHROPIC ACQUIRED IT INSTEAD OF SALESFORCE?!
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nice, @mercury
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"The Roman Army proved a leader can only control eight people. Nothing has changed since"...not exactly. The military adopted context windows and decentralized decision making a long time ago: See "Commander's Intent" It's how decentralized decision making is done despite what the military's "org chart" might imply. Before any mission or order is given, the Commander sits down and literally writes out the mission's "context": - Why the mission exists - The non-negotiable actions that must happen - What the battle space should look like when it's done That context is understandable two levels down, is inserted into the top of every order, backbriefed by the team, and memorized. Teams empowered with the Commander's Intent are expected to make real-time decisions on the ground themselves. So before building your company's own AI Jarvis, take a sec to do a quick check in with yourself to ensure you're doing the basics right: Have you clearly communicated your Commander's Intent to the team? Do they know exactly what the world looks after you've succeeded? Have you given them the freedom and flexibility to run with your intent?
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Starlink for the win. We were in very remote Patagonia when I got sick and needed antibiotics. We rode horseback to a outpost with Starlink, had a video consult with a Chilean doc, got the Rx, and some guy brought it to me on a 4 wheeler next day. Honestly a better healthcare experience than in the states lol.
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Founders, see how @cjpedregal paired their big round announcement with a meaningful product release? Be like Chris.
Replying to @cjpedregal
We’ve noticed lots of teams are finding ways to use Granola’s context across their company. So today we’re making that much easier by launching APIs, expanding our MCP, and introducing Spaces: a new way to share context with your team. Read more: granola.ai/blog/series-c/
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Amiright that coffee makers are either $300 for one that breaks annually or $12,000 for a good one?
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Instead of decoupling from QSBS tax benefits, NYC should reward exiting founders with an additional 15% bonus on liquidity proceeds paid for by the losers who created no shareholder value that year.
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How to spot a founder: "Someone who has internalized the rules so much that he can feel where they bend, where they want to break, where the new thing is hiding inside the old one. A transcendent ideal, reached from the inside, against every possible taste of his time."
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"Look we saw Ramp Sheets, and honestly it was sick, so we reactively pulled this forward on our roadmap. We hope you* enjoy it. *Agent Mode is generally available... for 365 copilot premium super duper plus customers in select markets within select regions of certain planets that may or may not be within this solar system."
Agent Mode in Excel is now generally available on desktop & web. Learn more from our very own @tmobrien on how he uses it:
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