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<div style="display: none; max-height: 0px; overflow: hidden;">LinkedIn released its 2025 Top 50 US Startups list, ranking companies by employee growth, engagement, and talent demand </div>
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<h1><strong> TLDR Founders <span id="date">2025-10-20</span></strong></h1>
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<strong>AI pricing strategies from Andreessen Horowitz's Martin Casado (Sponsor)</strong>
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If you're struggling to figure out your AI pricing, this <a href="https://tracking.tldrnewsletter.com/CL0/https:%2F%2Fmetronome.com%2Fwebinars%2Fmonetization-operating-model-webinar-series%3Futm_campaign=monetization-wp%26utm_medium=newsletter%26utm_source=tldr-founder%26utm_content=/3/0100019a0183d46f-80188e29-a39b-4d9b-8969-738ab0573ff0-000000/KzCXx5w-2rme-hCKiQTJSalE9YYnpRXVMS0l5h_hwlg=427" rel="noopener noreferrer nofollow" target="_blank"><span>live webinar</span></a> is for you. Martin Casado, General Partner at Andreessen Horowitz, will share new monetization strategies that go beyond flat fees and subscription models.
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<p>This session will look at <a href="https://tracking.tldrnewsletter.com/CL0/https:%2F%2Fmetronome.com%2Fwebinars%2Fmonetization-operating-model-webinar-series%3Futm_campaign=monetization-wp%26utm_medium=newsletter%26utm_source=tldr-founder%26utm_content=/4/0100019a0183d46f-80188e29-a39b-4d9b-8969-738ab0573ff0-000000/ikNDjR5j_Pmzq-ZkInQDiP4H0IttGw548EJuQRjQakA=427" rel="noopener noreferrer nofollow" target="_blank"><span>how companies like OpenAI are building monetization infrastructure</span></a>, and why AI is forcing every SaaS company to reinvent its own pricing and billing. Topics include:</p>
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<li>Why AI is accelerating the shift from pure subscription models to results-based and hybrid monetization models</li>
<li>How fast-growing AI companies are aligning product, finance, GTM, and engineering</li>
<li>How to treat pricing like a product to enable experimentation and scale</li>
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<strong>Startups Investing in Startups (5 minute read)</strong>
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When startups start acting like VCs, something's shifted. Vercel, barely past $200M in revenue, is now using investor cash to fund other startups, calling it ecosystem building. Maybe it's smart positioning in the AI infrastructure race, or maybe it's the oldest sign of a bubble.
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<strong>Is AI Adoption Slowing Down? (3 minute read)</strong>
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What if the AI boom isn't cooling off, just maturing faster than expected? Ramp's latest data shows paid AI adoption dipping again, even as retention jumps from 60 to 80 percent. Tech and finance lead the pack, but most industries still haven't caught up. The surprise is that companies aren't buying less, they're buying smarter. For founders, the gold rush phase is ending. The next wave belongs to products that prove lasting, repeatable value.
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<a href="https://tracking.tldrnewsletter.com/CL0/https:%2F%2Fwww.linkedin.com%2Fpulse%2Flinkedin-top-startups-2025-50-us-companies-rise-linkedin-news-hox6f%3Futm_source=tldrfounders/1/0100019a0183d46f-80188e29-a39b-4d9b-8969-738ab0573ff0-000000/FsxJ513fY0UvMgwTrjZ6_R0-EWpmFJYd0wSc95H1ytY=427">
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<strong>LinkedIn reveals 2025 Top 50 US startups (10 minute read)</strong>
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LinkedIn released its 2025 Top 50 US Startups list, ranking companies by employee growth, engagement, and talent demand. AI-focused firms like Anthropic, Character.AI, and Replit dominate the top spots, reflecting hiring momentum across the sector. Security startup Chainguard secured the No. 18 position after raising $356 million and reaching a $3.5 billion valuation.
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<div style="text-align: center;"><span style="font-size: 36px;">🧠</span></div>
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<h1><strong>Strategies & Tactics</strong></h1>
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<a href="https://tracking.tldrnewsletter.com/CL0/https:%2F%2Fhealthvc.substack.com%2Fp%2Finvestor-churn-why-founders-lose%3Futm_source=tldrfounders/1/0100019a0183d46f-80188e29-a39b-4d9b-8969-738ab0573ff0-000000/CRXrtqajN3fdT9zfZFqcWLs4iTLYSzQDj4PS0E7UGZQ=427">
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<strong>Investor Churn (4 minute read)</strong>
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<span style="font-family: "Helvetica Neue", Helvetica, Arial, Verdana, sans-serif;">
Your failed round might not be about your product - it could be about your process. Sixty percent of interested investors drift without ever saying no. They stop replying, delay calls, and ghost quietly. Investors see hundreds of deals quarterly. If your communication rhythm breaks, you slide from active to maybe-later. In healthtech, this gets worse because investors already expect slow timelines, so any process sloppiness signals you'll struggle with execution too. Attention decay is the real enemy - momentum leaks silently between interactions, and once that energy disappears, it's almost impossible to reignite
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<a href="https://tracking.tldrnewsletter.com/CL0/https:%2F%2Fwww.dearstage2.com%2Fp%2Fbuilding-outbound-from-scratch-a%3Futm_source=tldrfounders/1/0100019a0183d46f-80188e29-a39b-4d9b-8969-738ab0573ff0-000000/QQTNj8RqQtpgOfJaiKib3nzw57RZhvtQN6b9iM4TwhA=427">
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<strong>Building Outbound from Scratch: A Founder's Playbook (5 minute read)</strong>
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Three weeks perfecting cold email copy. Zero emails reaching inboxes. Salesmotion learned outbound the hard way - messaging doesn't matter when everything bounces to spam. Once they fixed deliverability, the actual sequence became clear. Build your account list first, maybe 200 companies that look like your best customers. Then work on infrastructure - validate emails, warm domains, send 10 per day max while you test. After that works, test messaging in small batches against specific personas. Track who responds from your target accounts, not just total replies.
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<a href="https://tracking.tldrnewsletter.com/CL0/https:%2F%2Fwww.lennysnewsletter.com%2Fp%2Feveryone-should-be-using-claude-code%3Futm_source=tldrfounders/1/0100019a0183d46f-80188e29-a39b-4d9b-8969-738ab0573ff0-000000/HdtITdEkszN8SL4UZNYjq-vvl9su2QHZ8hDS2bKCBJY=427">
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<strong>Everyone should be using Claude Code more (5 minute read)</strong>
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<span style="font-family: "Helvetica Neue", Helvetica, Arial, Verdana, sans-serif;">
Claude Code offers versatile AI capabilities for non-technical users, running locally to manage tasks like file organization, image enhancement, and video downloads. It excels in handling large files efficiently and performing tasks beyond cloud-based AI tools. Users share creative applications, including generating domain names, synthesizing customer call transcripts, and creating self-driving documentation.
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<div style="text-align: center;"><span style="font-size: 36px;">⚒️</span></div></div>
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<h1><strong>Tools & Resources</strong></h1>
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<strong>Promptless (Tool)</strong>
</span>
</a>
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<span style="font-family: "Helvetica Neue", Helvetica, Arial, Verdana, sans-serif;">
Promptless is an AI teammate that proactively drafts and updates customer-facing docs based on product changes and team activity.
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<strong>Pythagora (Tool)</strong>
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<span style="font-family: "Helvetica Neue", Helvetica, Arial, Verdana, sans-serif;">
Pythagora is an all-in-one AI dev platform that builds full web apps from scratch through natural language, handling specs, frontend, and backend in hours.
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<strong>Cekura (Tool)</strong>
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<span style="font-family: "Helvetica Neue", Helvetica, Arial, Verdana, sans-serif;">
Cekura helps AI teams launch and monitor voice and chat agents 10x faster with automated QA, simulation, and real-time performance monitoring.
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<div style="text-align: center;"><span style="font-size: 36px;">🎁</span></div></div>
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<div style="text-align: center;"><strong><h1>Miscellaneous</h1></strong></div>
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<span>
<a href="https://tracking.tldrnewsletter.com/CL0/https:%2F%2Finvesting101.substack.com%2Fp%2Fmomentum-moat%3Futm_source=tldrfounders/1/0100019a0183d46f-80188e29-a39b-4d9b-8969-738ab0573ff0-000000/yRe63PuDUOeuuHADRcCxY9ST2zU4mGKZa7ow7Y-GuG0=427">
<span>
<strong>Momentum != Moat (6 minute read)</strong>
</span>
</a>
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<br>
<span style="font-family: "Helvetica Neue", Helvetica, Arial, Verdana, sans-serif;">
An a16z partner just claimed momentum is the only moat that matters - get to $2M ARR in ten days or you're not interesting. Sounds exciting until you notice this mindset is poisoning an entire generation of companies. When billion-dollar funds only care about triple-digit growth rates, they're effectively declaring that 95% of successful business outcomes shouldn't exist. Wealthfront took 17 years to hit $308M revenue and $123M profit - that's a fantastic business, but to momentum investors it's a failure. The worse problem is that momentum attracts competition like blood in water. Legal AI, code gen, AI copywriters - every hot category now has five companies racing to $100M ARR while burning unsustainable amounts on compute and customer acquisition.
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</span>
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<span>
<a href="https://tracking.tldrnewsletter.com/CL0/https:%2F%2Fhellooperator.substack.com%2Fp%2Fdolly-parton-has-an-opinion-on-how-to-improve-your-culture-ede7085dd914%3Futm_source=tldrfounders/1/0100019a0183d46f-80188e29-a39b-4d9b-8969-738ab0573ff0-000000/j-2OKW8StNV7WsBfX1wMamvQKz22aAasDv4CzXroEYU=427">
<span>
<strong>How To Build Core Values That Mean Something (4 minute read)</strong>
</span>
</a>
<br>
<br>
<span style="font-family: "Helvetica Neue", Helvetica, Arial, Verdana, sans-serif;">
Dolly Parton accidentally wrote the best business advice ever - find out who you are and do it on purpose. Many companies build culture by measuring employee satisfaction scores or forming wordsmithing aspirational phrases about who they want to become someday. That's backwards. Your core values already exist in how your best people behave currently.
</span>
</span>
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<span>
<a href="https://tracking.tldrnewsletter.com/CL0/https:%2F%2Fnews.crunchbase.com%2Fdiversity%2Fgoverning-ai-companies-california-partners-project-illumyn%2F%3Futm_source=tldrfounders/1/0100019a0183d46f-80188e29-a39b-4d9b-8969-738ab0573ff0-000000/cw3OSzg5aA2FuUUHg6YIMlYGvVW1U-NIMl7gDbFhgzQ=427">
<span>
<strong>Who Is Governing AI Companies? For Nearly Half Of AI Startups In California, The Answer Is Only Men (10 minute read)</strong>
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</a>
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<br>
<span style="font-family: "Helvetica Neue", Helvetica, Arial, Verdana, sans-serif;">
A study of 140 AI companies in California revealed that women occupy only 15% of board seats in private AI startups, and 43% of these companies have no women on their boards. The lack of gender diversity stems from structural biases favoring executives and investors, areas where women are underrepresented, and behavioral biases that prioritize familiar candidates over diverse talent. The study suggests that appointing independent directors and expanding search networks can help improve board diversity.
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</span>
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<div style="text-align: center;"><span style="font-size: 36px;">⚡</span></div></div>
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<h1><strong>Quick Links</strong></h1>
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<a href="https://tracking.tldrnewsletter.com/CL0/https:%2F%2Ffs.blog%2Fbrain-food%2Foctober-19-2025%2F%3Futm_source=tldrfounders/1/0100019a0183d46f-80188e29-a39b-4d9b-8969-738ab0573ff0-000000/Wdfny5qRNQIbLR_wr0C0DBi4gxftZR3l3u4aYrksG0I=427">
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<strong>Life Rewards Repetition (1 minute read)</strong>
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<span style="font-family: "Helvetica Neue", Helvetica, Arial, Verdana, sans-serif;">
Founders romanticize novelty, but most progress comes from compounding small, repeatable motions.
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<span>
<a href="https://tracking.tldrnewsletter.com/CL0/https:%2F%2Fnickgrossman.xyz%2Fthe-internets-next-business-model-a-conversation-with-cloudflares-matthew-prince%3Futm_source=tldrfounders/1/0100019a0183d46f-80188e29-a39b-4d9b-8969-738ab0573ff0-000000/VFjOhQG93h6wcVzqOCwiSwklZxJ8mJ0to0IJCuw87ZE=427">
<span>
<strong>The Internet's Next Business Model: A Conversation with Cloudflare's Matthew Prince (3 minute read)</strong>
</span>
</a>
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<br>
<span style="font-family: "Helvetica Neue", Helvetica, Arial, Verdana, sans-serif;">
Matthew Prince of Cloudflare highlights a shift from search engines to AI-driven "answer engines," challenging the current internet business model.
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<a href="https://tracking.tldrnewsletter.com/CL0/https:%2F%2Fbryce.medium.com%2Fa-process-for-having-it-all-with-jason-jacobs-b23158c65806%3Futm_source=tldrfounders/1/0100019a0183d46f-80188e29-a39b-4d9b-8969-738ab0573ff0-000000/Tcehlq9At3Hc2nugrZWWPqLDu_dAkwm5CfSxKJX6N1U=427">
<span>
<strong>A Process for Having it All with Jason Jacobs (4 minute read)</strong>
</span>
</a>
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<br>
<span style="font-family: "Helvetica Neue", Helvetica, Arial, Verdana, sans-serif;">
Jason Jacobs, a successful founder of Runkeeper, is developing processes to balance entrepreneurship with personal fulfillment.
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