Silicon Hills Lawyer https://siliconhillslawyer.com/ A top-tier Startup Lawyer helps Startups and Founders safely navigate high-stakes legal and financing issues, while keeping VCs honest. Fri, 16 Jan 2026 15:22:39 +0000 en-US hourly 1 61507486 Should VCs Control Your Startup’s Lawyers? https://siliconhillslawyer.com/2026/01/15/should-vcs-control-startups-lawyers/ https://siliconhillslawyer.com/2026/01/15/should-vcs-control-startups-lawyers/#respond Thu, 15 Jan 2026 19:05:20 +0000 https://siliconhillslawyer.com/?p=4042 Related Reading: Negotiation is Relationship Building With this being my 15th year as an Emerging Companies (“Startup”) lawyer, now as a partner at the country’s leading company-side boutique law firm in the space, I can say definitively that one of the defining questions of my career has been: Whom should a startup’s lawyers really work for? […]

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]]> https://siliconhillslawyer.com/2026/01/15/should-vcs-control-startups-lawyers/feed/ 0 4042 Startup Founders Using ChatGPT and Gemini for Legal https://siliconhillslawyer.com/2025/10/22/startup-founders-chatgpt-gemini-legal/ https://siliconhillslawyer.com/2025/10/22/startup-founders-chatgpt-gemini-legal/#respond Wed, 22 Oct 2025 20:08:00 +0000 https://siliconhillslawyer.com/?p=4008 Related Reading: Legal AI and the Future of Startup Law TL;DR: No matter how much it might horrify conservative lawyers, founders are going to use AI for some legal tasks, and it’s actually an upgrade from what they’ve been doing previously for low-stakes issues (just Googling and winging it). But there are a few things […]

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]]> https://siliconhillslawyer.com/2025/10/22/startup-founders-chatgpt-gemini-legal/feed/ 0 4008 Seed-Stage Startups Should Shrink Their Option Pools https://siliconhillslawyer.com/2025/05/13/seed-startup-shrink-pool-safes/ https://siliconhillslawyer.com/2025/05/13/seed-startup-shrink-pool-safes/#respond Tue, 13 May 2025 16:10:01 +0000 https://siliconhillslawyer.com/?p=3941 Background reading: Reserve an Option Pool; Not an Ocean Pre-Seed Funding with Post-Money SAFEs: Revisited in 2024 You only get 100% of your cap table to give away (or keep), and the sad fact is founders make all sorts of tactical errors that needlessly give up points to investors and other parties. Sometimes those errors […]

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]]> https://siliconhillslawyer.com/2025/05/13/seed-startup-shrink-pool-safes/feed/ 0 3941 Legal AI and the Future of Startup Law https://siliconhillslawyer.com/2024/10/15/legal-ai-future-of-startup-law/ https://siliconhillslawyer.com/2024/10/15/legal-ai-future-of-startup-law/#respond Tue, 15 Oct 2024 18:11:12 +0000 https://siliconhillslawyer.com/?p=3841 It’s been a while since I’ve written on legal tech and startup law, and given recent developments in AI, it feels like an update is in order. For context, I’m a Partner and legal CTO at Optimal, an elite boutique law firm focused on ECVC, M&A, and Tech Transactions for VC-backed startups. We’re about 20 […]

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]]> https://siliconhillslawyer.com/2024/10/15/legal-ai-future-of-startup-law/feed/ 0 3841 Pre-Seed Funding with Post-Money SAFEs: Revisited in 2024 https://siliconhillslawyer.com/2024/07/09/startup-seed-post-money-safes-2024/ https://siliconhillslawyer.com/2024/07/09/startup-seed-post-money-safes-2024/#respond Tue, 09 Jul 2024 23:30:27 +0000 https://siliconhillslawyer.com/?p=3789 There are few markets that evolve faster than the world of startups, for unsurprising reasons. I figured it was time to revisit some of my writings on seed and pre-seed funding given how much the market has evolved since 2019-2021, when I last wrote about this topic in depth. First, a brief history: 1990s – […]

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