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<div style="display: none; max-height: 0px; overflow: hidden;">Every AI market feels crowded because only a few players can win. Speed of shipping is an advantage but not a durable one </div>
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<h1><strong> TLDR Founders <span id="date">2026-06-17</span></strong></h1>
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<strong>Webinar: How I Used AI to Automate Sales Ops and Scale to Multi-Million ARR (Sponsor)</strong>
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Scaling sales ops usually means more headcount. Plane co-founder Staszek Kolarzowski (YC '17) took the opposite route: he built an AI engine to run his, on the way to multi-million ARR. In this <a href="https://tracking.tldrnewsletter.com/CL0/https:%2F%2Fplane.zoom.us%2Fwebinar%2Fregister%2F6017799011146%2FWN_bfVwvAK9TvGtavsDhp2Xtg%3Futm_source=TLDR%26utm_medium=newsletter%26utm_campaign=2026-06-17_Primary_Plane%26utm_content=Body_founder_founder_webinar%23%2Fregistration/1/0100019ed57b7b16-ceb8d473-01ff-4fad-9539-a2b3b61cde63-000000/f5A7pXlcgYIlfTJCOnHH9TeVd6HBE7vWcbT7lkPCFSY=452" rel="noopener noreferrer nofollow" target="_blank"><span>founder-to-founder webinar</span></a>, he'll give live demos of what's in production today and what you can build yourself. You'll walk away knowing how to:
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<li>Run growth experiments that track campaign performance and flag issues before they hit results</li>
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<li>Monitor pipeline health, auto-build win plans, and surface deal gaps before they stall</li>
<li>Calculate commissions accurately and sync them straight to payroll</li>
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<strong>How to compete in "crowded" AI markets (4 minute read)</strong>
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<span style="font-family: "Helvetica Neue", Helvetica, Arial, Verdana, sans-serif;">
Decagon CEO Jesse Zhang argues every AI market feels crowded because only a few players can win, and walks through the brutal customer-service AI sales cycle where Decagon gets compared to Salesforce and Google adding AI, pre-AI Intercom, AI-natives like Sierra, and the customer's own MVP. Speed of shipping is an advantage but not a durable one, because AI tools have compressed build-and-copy timelines so much that a feature lost in a deal goes straight onto every competitor's roadmap.
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<a href="https://tracking.tldrnewsletter.com/CL0/https:%2F%2Fvinvashishta.substack.com%2Fp%2Fai-cant-survive-your-c-suites-magic%3Futm_source=tldrfounders/1/0100019ed57b7b16-ceb8d473-01ff-4fad-9539-a2b3b61cde63-000000/1PcztHH9RYwfUsFWJwOrTyiDmFgNPuLPVVgJywpx_uk=452">
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<strong>AI Can't Survive Your C-Suite's Magic Thinking (12 minute read)</strong>
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Corporate culture and agenda setting have failed engineering organizations. Data wrangling and cleansing have become more about making the data align with the business rather than making data more valuable to improve decision-making. Executives are relying too much on magic thinking. Shareholders and the board are now holding CEOs accountable for choosing evidence over comfort to right the ship.
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<h1><strong>Strategies & Tactics</strong></h1>
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<strong>How to Pivot Well (12 minute read)</strong>
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The iconic stories of the Web 2.0 era give founders the hope that unimaginable riches are just an iteration away. AI makes faster pivots more possible. Knowing when to pivot, how fast, and toward what has become a core skill for founders in the AI era. This post looks at what founders need to think about when considering a pivot.
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<strong>A technical guide to building your own learning loop (39 minute read)</strong>
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The winning move in AI now is to build a learning loop on top of the best model. This allows data and usage to compound into IP that nobody can rent back to you. This post looks at why this should be done and provides a blueprint for how to create a winning learning loop.
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<strong>How Rivian plans for stuff that doesn't exist yet (6 minute read)</strong>
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<span style="font-family: "Helvetica Neue", Helvetica, Arial, Verdana, sans-serif;">
Rivian needed a new factory for its cheaper SUV, so it built the car in the old one and pocketed $2.25 billion. Its CFO's rule is to wring every last drop out of what you already own before you pour concrete, the hardware version of staffing for the work you have, not the work you hope to get. The new model pulled profitability forward instead of pushing it out, because sharing the factory spread fixed costs over more cars and made the older lines cheaper too. Revenue tripled in two years while operating costs held flat. Sometimes the cheapest way to grow is to not build the new thing.
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<h1><strong>Tools & Resources</strong></h1>
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<strong>Your next enterprise customer is already here (Sponsor)</strong>
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<span style="font-family: "Helvetica Neue", Helvetica, Arial, Verdana, sans-serif;">
Startups in this program have closed deals with customers like Visa, Meta, Unilever, GM, AstraZeneca and Walmart.<br>Build with the coding assistant used by 90% of the Fortune 100.<br>Scale on AI-ready cloud infra backed by enterprise-grade security, privacy, and governance.<br>Sell on Marketplace.<p></p><p><a href="https://tracking.tldrnewsletter.com/CL0/https:%2F%2Fwww.microsoft.com%2Fstartups%2Fapply%3Fwt.mc_id=tldrfounders_2_061726_newsletter_startups/1/0100019ed57b7b16-ceb8d473-01ff-4fad-9539-a2b3b61cde63-000000/84CfgjXfD1GJgyioBSt-cVA5OEhUwLYBNghH4s3J4qI=452" rel="noopener noreferrer nofollow" target="_blank"><span>See why founders choose Microsoft for Startups.</span></a>
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<strong>GLM-5.2 (Hugging Face Repo)</strong>
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Z.ai's GLM-5.2 flagship model marks a substantial leap in long-horizon capability over GLM-5.1. It has a solid 1M-token context window and new capabilities. Its improved architecture reuses per-token FLOPs by 2.9x. The model has been released under an MIT open-source license.
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<strong>ChatGPT Opens Ads for All: How to React to This Shift (8 minute read)</strong>
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Self-serve access to ChatGPT Ads is now open to all advertisers in the US. OpenAI crossed $100 million in annualized ad revenue in six weeks with less than 20% of eligible users seeing ads daily. 85% of free and Go tier users are eligible to see ads. OpenAI has confirmed rollout to Canada, Australia, New Zealand, the United Kingdom, Japan, South Korea, Brazil, and Mexico.
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<div style="text-align: center;"><strong><h1>Miscellaneous</h1></strong></div>
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<a href="https://tracking.tldrnewsletter.com/CL0/https:%2F%2Fwww.saastr.com%2Fdo-you-treat-your-20-year-customers-worse-than-your-new-ones%2F%3Futm_source=tldrfounders/1/0100019ed57b7b16-ceb8d473-01ff-4fad-9539-a2b3b61cde63-000000/BuV2kToQJT1UjpvCbHLfFxGAOlZjVK5vn2TQRQszoNQ=452">
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<strong>Do You Treat Your 20-Year Customers Worse Than Your New Ones? You Probably Do (5 minute read)</strong>
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<span style="font-family: "Helvetica Neue", Helvetica, Arial, Verdana, sans-serif;">
Lemkin names the "20-year tax" where loyal customers get squeezed because they've already signed, integrated, and trained their teams while new logos get war rooms, CEO involvement, and free custom integrations, a pattern running through nearly every pre-AI B2B company where the CSM rotates every 14 months and nobody remembers the case studies or referrals.
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<a href="https://tracking.tldrnewsletter.com/CL0/https:%2F%2Fcommoncog.com%2Fthere-are-many-configurations-of-business-that-work%2F%3Futm_source=tldrfounders/1/0100019ed57b7b16-ceb8d473-01ff-4fad-9539-a2b3b61cde63-000000/mL33UIG6c0W3b9qnexUs_gKi32v3vrOYSvqGdNfB740=452">
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<strong>There are many configurations of business that work (12 minute read)</strong>
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<span style="font-family: "Helvetica Neue", Helvetica, Arial, Verdana, sans-serif;">
The venture-backed rocketship is just one way to build a company, and you absorbed it without noticing. Patagonia stopped chasing growth, let customers set its pace, and added a mission that cost real money, and its near-death cash scares went away. Warren Buffett took the cash off a dying textile mill's books, bought stocks with it, and grew Berkshire into a giant without raising a dollar of venture money. "Raise, grow fast, exit" is a script, not a law, and there are far more ways to win than the one everyone copies. The startup is one configuration. Is it the right one for the life you want?
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<strong>How to Calculate Compute-adjusted LTV (13 minute read)</strong>
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Compute-Adjusted LTV is a new metric that measures fixed or semi-fixed AI revenue with variable compute costs.
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<strong>Does the Rule of 40 Work for Hardware? (6 minute read)</strong>
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The Rule of 40, useful in SaaS for balancing growth and profitability, often misrepresents hardware companies due to longer development cycles and upfront costs.
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<strong>Slop is a bad story (3 minute read)</strong>
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<span style="font-family: "Helvetica Neue", Helvetica, Arial, Verdana, sans-serif;">
Slop has nothing to do with AI and everything to do with story.
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<a href="https://tracking.tldrnewsletter.com/CL0/https:%2F%2Fwww.thisisgoingtobebig.com%2Fblog%2F2026%2F6%2F16%2Fclimbing-the-wrong-mountain-when-founders-build-around-familiar-problems%3Futm_source=tldrfounders/1/0100019ed57b7b16-ceb8d473-01ff-4fad-9539-a2b3b61cde63-000000/vECVXSnEVfYJYRgJqGy4ZOvtp6LTDgf43JU9hqZZyVQ=452">
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<strong>Climbing the Wrong Mountain: When Founders Build Around Familiar Problems (6 minute read)</strong>
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<span style="font-family: "Helvetica Neue", Helvetica, Arial, Verdana, sans-serif;">
The sequence of mountains is when founders fixate on the mountain in front of them, putting everything they have into climbing it, only to realize there are other mountains behind it.
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