Brian Simmons
@brian2346
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CPTO @tryfondo Past: VP Product/Engineering @ScaleFactor, Founder @EventSlice, @Spiceworks tweets are my own, TarHeel.
Austin, TX
Joined October 2009
RT @jasonlk: The hardest part of all of this isn't shipping code. Or winning the deal. Or raising capital. It's getting really, really good….
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Founders: the most generous tax break in America just leveled up.QSBS changes = $2M+ in additional tax-free upside on your exit. Huge shoutout to @tryfondo’s Jake Wedig for breaking it all down 👇.
It’s official - last week QSBS got a massive upgrade . Founders, early employees, and investors now get even more tax-free upside when their startup exits: $2M+ in savings. The most generous tax break in America 🇺🇸 just got more generous. Here’s what changed (shout out to Jake
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RT @davj: America just handed founders a tax break to build wealth, fast:. 🇺🇸 Corporate tax rate: 21%. 🇺🇸 QSBS limit: $15M. 🇺🇸 Partial gain….
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I agree and when it comes to workflows and deep domain expertise, @tryfondo has this in spades ♠️.
. @levie has a great rationale for b2b software sticking around. Companies are not buying bits, they're buying an operational workflow coming from deep domain understanding. But that argument doesn't hold for my individual needs. I know what I want best.
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Completely agree. This is a subtle but important point. AI doesn’t need to perfectly match humans to drive massive value. It just needs to help, and in many cases, that’s already enough to change workflows, reduce costs, or create entirely new experiences. The bar isn’t.
+1 for "context engineering" over "prompt engineering". People associate prompts with short task descriptions you'd give an LLM in your day-to-day use. When in every industrial-strength LLM app, context engineering is the delicate art and science of filling the context window.
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Slightly used, emotionally damaged. Comes with unpaid parking tickets and a copy of the Constitution. 😂
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D-Day reminds us of the power of bravery and resolve. On this day, 81 years ago, thousands stepped into history with courage that still inspires generations. Grateful for their service. Proud of their legacy.
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That moment when both internal and external customers love the release: .Me, pretending to be humble while mentally accepting my imaginary Product Grammy.
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We’re moving from human in the loop to AI in the lead. The next wave of software isn’t just AI powered, it’s AI native, where humans shift from operators to orchestrators. UX, infra, and trust all get reimagined in this paradigm.
Initially we thought the future of software was AI to help humans do work. But it’s actually inverted. Instead, the future will be software for humans to manage AI Agents do work. This will cause us to rethink what the design of software is going forward.
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Absolutely. The most enduring tech companies don’t just solve current problems, they create new standards for how entire industries operate. The key is staying curious, close to customers, and willing to challenge what’s “normal.”.
The thing some people get wrong in thinking about AI is imagining the world as a zero sum system where we can only create a certain amount, and so AI creating means taking something away from people working. This is entirely the wrong way to think about AI, and the economy.
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Every time we release something, this is me and @davj says, "This is a decent first version." 🤣🤣 Kidding of course!
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RT @moanasudha: I saw a PM working today. No @grok. No @chatprd .No @NotionHQ Doc. Just sat there writing PRDs from scratch on MS word. Lik….
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Normal first principles: break things down to atoms and build up. AI first principles: assume intelligence is cheap, fast, and always improving. The deeper truth?.AI compounds. Every mistake is a training example. Every user makes it smarter. The more it’s used, the more it.
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All the energy around MCP is deserved. For accounting and fintech, it’s not just hype, it’s how we are going from brittle workflows to agents that reason, route, and act across complex systems. @tryfondo is building for that future now!.
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Going out of my way to get home from San Francisco via Seattle has some small perks! Cc: @AlaskaAir
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RT @tryfondo: Not all events move the needle. This one did. Thanks to @stripe sessions for making space for real conversations https://t.co….
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RT @tryfondo: San Francisco. Founders. Fundraising. Live from Founders Network fnIRL! 📍. fnIRL brought FN’s online mentorship to real life….
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