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<div style="display: none; max-height: 0px; overflow: hidden;">Vertical software stocks are down 43% from their highs. DevTools are down 21%. The gap doesn’t track with which sectors AI can actually replace </div>
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<h1><strong> TLDR Founders <span id="date">2026-02-09</span></strong></h1>
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<strong>Reid Hoffman sends 100+ messages a day. He stopped typing 75% of them (Sponsor)</strong>
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Co-founder of LinkedIn, partner at Greylock. Founders don't have time for dictation tools that don't work.<p></p><p><a href="https://tracking.tldrnewsletter.com/CL0/https:%2F%2Fref.wisprflow.ai%2Ftldr-founders/3/0100019c428405f3-89b41505-5342-461e-a714-51181ce594f7-000000/bM6-xlaDpFT4ZU-9rqiCkSs3Lv5IFdGJyWZOxVo1TRA=443" rel="noopener noreferrer" target="_blank"><span><strong>Wispr Flow</strong></span></a> is different:</p>
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<p>"People go from skeptical to instantly obsessed with Wispr." — Reid Hoffman</p>
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<strong>How Markets Price AI Risk (3 minute read)</strong>
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Vertical software stocks are down 43% from their highs. DevTools are down 21%. The gap doesn't track with which sectors AI can actually replace - it correlates almost perfectly with growth rates. Slow growers (8-11%) are getting crushed while faster growers (21-22%) are holding up. The market isn't pricing in AI disruption. It's pricing in who can outrun it.
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<strong>Churn/Retention in the Era of AI (2 minute read)</strong>
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AI companies are fighting churn and facing a retention apocalypse. The real retention curve starts when the hobbyists leave, leaving only the people who've integrated AI into actual work. AI churn is higher because it's easy to buy and cancel, and many trials reflect curiosity more than long-term commitment. Companies that win move upmarket, build for habitual workflows, and add services/FDEs on top of AI.
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<h1><strong>Strategies & Tactics</strong></h1>
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<strong>Uplevel or Replace? A CEO's Dilemma at Series B (5 minute read)</strong>
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ZoomInfo was built from $0 to IPO, and its founder has a nuanced take on the "when do you upgrade your early team" question. His answer: every exec was a first-timer once, and external hires aren't automatically better. The real question is whether someone can do what the business needs for the next 12-24 months, not whether they've done it before.
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<strong>Endgame Play (8 minute read)</strong>
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Modern systems optimize by simulating terminal states, collapsing openings and middlegames into scripted execution, from chess engines to modern warfare and AI strategy. This endgame-first reasoning treats real-world uncertainty as a series of bottlenecks to skip, rewarding fluency in simulation over engagement with unresolved complexity. The failure mode emerges when actors mistake the ability to model outcomes for proximity to them, abandoning the middlegame where risk, ambiguity, and real consequences still concentrate.
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<strong>Two Modes of Storytelling: Studio and Newsroom (6 minute read)</strong>
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Studio mode focuses on slow, deliberate storytelling with deep craft and novel perspectives, producing rare, timeless content that gains momentum through careful refinement. Newsroom mode prioritizes fast, responsive storytelling, engaging with ongoing conversations and surfacing insights while the moment is alive. The most effective storytellers cycle between the two, letting newsroom responsiveness inform studio work and studio depth amplify newsroom relevance, creating a feedback loop that balances craft with timeliness.
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<strong>Stop losing deals to forgotten follow-ups. (Sponsor)</strong>
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<strong>Fulcrum (Tool)</strong>
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The Agentic Debugger for AI Systems.
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<strong>Klaus: (Tool)</strong>
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Get your OpenClaw Personal Assistant in 5 minutes.
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<strong>Skillkit (Tool)</strong>
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Package manager and CLI for creating, storing, and distributing reusable skills and instructions across multiple AI coding agents.
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<div style="text-align: center;"><strong><h1>Miscellaneous</h1></strong></div>
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<strong>You can build a $10B+ company fully remotely (16 minute read)</strong>
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All large companies work remotely - the only people truly working 'in person' at any of these companies are the ones sitting within earshot. Everyone else is collaborating through screens. Hire people with agency who want to work hard. Employees who prefer remote work just want to do their best work in an environment that suits them.
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<strong>The Incompetent Confidence Complex (5 minute read)</strong>
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Why do we consistently reward confidence over competence, and how does Dunning-Kruger play out in startups? The best operators don't start confident - they iterate until they actually know what they're doing, and the real confidence follows naturally.
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<strong>Boil the Ocean (4 minute read)</strong>
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<span style="font-family: "Helvetica Neue", Helvetica, Arial, Verdana, sans-serif;">
The old adage was "don't boil the ocean." With artificial superintelligence on the horizon, it's time to retire that phrase entirely. The fear of the future is directly proportional to the smallness of your ambitions. If your plan is to maintain the status quo, AI is terrifying. If your plan is to build something dramatically bigger, it's the best news you've ever gotten. This is Jevons Paradox for everything: when a resource becomes dramatically more efficient, you don't use less of it, you use vastly more.
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<h1><strong>Quick Links</strong></h1>
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<strong>The circular logic of our metrics (4 minute read)</strong>
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Design Thinking's vocabulary shift led stakeholders to misuse terms like "intuitive" as shorthand for "familiar."
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<strong>Dear SaaStr: What's the #1 Reason You See Sales Reps Fail These Days? (3 minute read)</strong>
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Seasoned sales reps fail most often because they insist on using their own playbooks instead of adopting the startup's proven process and framework.
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<strong>Will Vertical AI Survive? (8 minute read)</strong>
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Foundation model vendors are rapidly verticalizing, compressing the window for Vertical AI companies that rely on short or medium “last-mile” workflows.
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