Sandy Parakilas

Thrilled to announce that Together Fund is investing in Sentra, alongside a16z speedrun! You track results in Jira. Decisions in Notion. Conversations in Slack. But the reasoning, the debates, trade-offs, and context behind why you chose A over B, disappears into what we call "Dark Matter." A decision made in March looks insane by July because no one remembers the constraints that made it smart. I lived this firsthand at Twitter scaling from 800 to 8,000 employees, and at Google while launching AI Overviews to billions at planet scale. The problem isn't process. Process is compensation for something deeper: organizational amnesia. An organization’s "Systems of Record" doesn’t solve this, they encode it. They store what happened, never why. That's why we are investing in Sentra. Sentra is the always-on collective memory that eliminates organizational amnesia by maintaining accurate context for all members and agents, functioning as an operational nervous system. It connects to every channel where work happens, meetings, Slack, email, code commits, docs, calendars, and treats them not as artifacts to search, but as living signals to synthesize. The fleeting and the permanent, unified into a memory that understands. The founding team is built for this: - Jae Gwan Park (CEO): Product-first founder, memory systems research at UofT and MIT - Ashwin Gopinath (CSO): Former MIT professor, created "Reflexion" (NeurIPS 2023), agents that learn from mistakes, 2x founder - Andrey Starenky (CTO): Early Vapi engineer, ex-IBM, built to process enterprise-scale data firehose Together is an operator-led fund. We invest in problems we've lived. This is one of them. Many congrats Jae, Ashwin and Andrey, we are so excited to partner with you! Read the full thesis: https://lnkd.in/gixj9cE4 Book a demo: https://www.sentra.app/ #OrganizationalMemory #AI #Sentra #TogetherFund #a16z #ContextGraphs

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Project Vend reads less like a capability story and more like a governability story. Phase two improved because institutional scaffolding (tools, procedures, role separation) reduced predictable judgment failures—persuasion, compliance blind spots, boundary confusion, values drift. The board-level question isn’t “can an agent run a business?” but “what governance primitives must exist before we delegate authority.” Until incentives, escalation rights, and refusal boundaries are structurally enforced—not merely prompted—agents remain high-performing managers, not autonomous executives.

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Building a startup is hard. It is especially hard in a country like Nigeria, where the ecosystem is yet to mature, and there are still many challenges to navigate. It is confusing, lonely, and full of uncertain decisions. Founders, especially early-stage founders, need as much support as they can get. Not “inspire to perspire” posts, but practical support on hiring, operations, funding, customer research, and navigating the regulatory landscape. Too many founders are surrounded by noise, surface-level advice, and generic content that does not reflect their current realities. What they need is a community that understands exactly what they are going through and can offer context that is immediately useful. Sierra Collective exists to be that community. A space where founders learn from one another’s live experiences and shorten the painful trial and error that usually defines the early stages of building. At Sierra, we believe that the most valuable support comes from those who are active in the trenches, navigating the same obstacles. If you are an early-stage founder, you should join the Sierra Collective. You do not have to figure everything out alone. As the African proverb says, “If you want to go fast, go alone. If you want to go far, go together.” Join Sierra: https://lnkd.in/d-Nzmtkq

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California just handed cities a new enforcement tool to track your Airbnb. SB 346 took effect January 1, 2026. Now any California city can demand that Airbnb and Vrbo turn over detailed information about every listing: addresses, booking nights, and compliance status. This isn't theoretical. Cities like Los Angeles and San Francisco have been waiting for exactly this kind of authority. If you operate STRs in California, the compliance conversation starts with your registration. Is it current with each municipality where you operate? Does your listing display the correct permit number? Local occupancy limits vary significantly by city, so what flies in San Diego might get you fined in Santa Monica. Then there's the tax question. Platforms collect state lodging taxes automatically, but many local taxes are still your responsibility to remit. Documentation matters when audits come knocking. The broader trend is clear. 2025 saw more states tighten platform accountability. Louisiana now requires Airbnb and Vrbo to collect and remit sales tax as accommodation intermediaries. New York counties are building registries with detailed booking data requirements. Here's what I'm seeing with STR operators who stay ahead of this: they're using AI to handle the communication burden that compliance creates. Automated guest messaging about local quiet hours, occupancy limits, parking rules. Compliance gets you legal. Automation gets you sane. The operators who survive 2026 won't be the ones who ignored the regulatory shift. They'll be the ones who got compliant and then freed themselves from the operational weight of staying that way. Is your STR portfolio ready for January audits? And more importantly, is your communication system ready to support the guest experience while you focus on the business side? If you're curious what AI-assisted guest communication looks like for STR operators, I'm happy to walk through it. Drop a comment or send me a DM.

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U.S. energy demand is surging — don’t get left behind. New gas projects and large industrial loads are reshaping power markets at breakneck speed. In this high-stakes landscape, timely and accurate data is essential. Halcyon’s Data Products, powered by a regularly updated authoritative data catalog of 4.5+ million documents from all 50 public utility commissions, ensure you always have the latest energy market intelligence. Download this guide to see how AI can help power sector stakeholders find new growth opportunities first.

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🔓 New Tool for Transparency Advocates in California 📂🔍 I’m excited to share FOIAFastLane California — a custom GPT I created to help you draft, refine, and appeal California Public Records Act (CPRA) requests with ease and legal accuracy. Whether you're: ✔️ A journalist chasing accountability ✔️ A lawyer or activist demanding public records ✔️ A citizen curious about local government ✔️ Or a business seeking competitor intelligence -- this GPT guides you step-by-step through crafting effective, statute-based CPRA requests. 🧠 Built on the full CA Government Code §§ 7920.000–7931.000 & caselaw 🛠️ Drafts requests, explains exemptions, and helps push back on denials 📤 Accessible to anyone with a browser and a question 🔗 Try it here → https://lnkd.in/gY_w6RK6 Pro tip: After generating your first CPRA request, ask ChatGPT to expand upon it with relevant statutes and caselaw, and then ask it to "pressure-test" the request for anything that might be missing. If you want expert guidance on CPRA requests, or FOIA in general, visit www.foiafastlane.com

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Seattle VC panels are not exactly known for being spicy, which is why my AMA with Brooke and Rolanda at AI House last night was so refreshing. We got into the questions founders are too embarrassed to ask out loud. How do VCs actually decide behind closed doors? What counts as traction when you have zero revenue? Is enterprise SaaS dead? Do Seattle founders actually have a shot against the Bay Area? A few takeaways that stood out: ✅ Associates can't get to yes without a partner sponsor — but partners often can't reach deals without associate diligence. Arm them with the facts to fight for you internally. ✅ Expect 50-70 investor conversations before a term sheet. Send your deck a day early but assume nobody read it 😎 ✅ Enterprise SaaS isn't dead, but it's shifting from seat-based to usage and outcome-based pricing. Large orgs still need governed software. ✅ Traction isn't just revenue. How excited are your customers? Would they advocate for you? Paying pilots with automatic, KPI-specific conversion > free trials, every time. ✅ Learning slope > starting background. The strongest founders they've backed adapted fast — not started perfect. Brooke and Rolanda WILL take a second meeting even if you whiff the first one! ✅ Seattle has fantastic enterprise buyers and founders with sales relationships into them. But the equity-vs-cash culture gap is real, and hiring against big tech is still hard. What made it different was how candid Brooke and Rolanda were about what actually happens after your pitch ends, aka the internal deal dynamics most founders never see. Shoutout to the room full of 100+ early-stage founders who went against the Seattle grain and asked hard questions live to the VCs. That energy is what makes AI House work. Huge thanks to Brooke B. (FUSE) and Rolanda Fu (Madrona) for keeping it real! More AMAs like this coming. Tag a founder who we should invite for the next one! #AIHouse (photo credit to Jonathan G. Blanco 🛠)

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Really important point Dave. Regulations may force change, but trust is what sustains platforms longterm. Privacy first, on-device protection shows that safeguarding children doesn’t require surveillance alone and that’s a critical distinction more developers need to understand and adopt.

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Today we’re sharing some big news. Ando raised a $4M seed round, led by Slow Ventures, with participation from Blitzscaling Ventures, Zero Capital, Monochrome Capital, Gaingels, Mana Ventures, Fireroad, and additional investors. Hourly work powers a huge part of the economy but scheduling is still a mess. Too often, staffing doesn’t match real demand, shifts change at the last minute, and workers are left trying to juggle childcare, commutes, school pickup, and second (or third) jobs. That chaos is expensive for businesses and brutal for workers. Ando exists to make hourly work more predictable. We use AI to forecast demand for each location and help teams build schedules that fit real people. We’ve been in the field with enterprise customers for over a year, and the early traction is encouraging: - 90%+ daily demand accuracy  - 100% conversion from presentation → pilot → paid platform - 100% retention so far In some locations, customers have seen $60K–$80K in incremental revenue (results vary and aren’t solely attributable to Ando) Most importantly, this is about treating workers’ time like it matters. If you’re working multiple jobs, a last-minute schedule change isn’t a small inconvenience, it can blow up your week. This funding will help us expand our forecasting and scheduling platform and scale deployments with enterprise customers. Grateful to our investors, advisors, customers, and team. And if you’re an operator or leader living this problem every day, I’d love to connect. Full release below. https://lnkd.in/gyYjqmts #Ando #AI #ArtificialIntelligence #WorkforceAI #FutureOfWork #LaborTech #RestaurantTech #RetailTech

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We're back with another Startup Radar post highlighting up-and-coming early stage Seattle-area tech companies. Vercept, led by Kiana Ehsani, is building a new computer interface with help from AI and just released more details about its product. CHASSY, led by Chuka Okoye, just raised $1.2 million to help companies operate software for robotic fleets. Haply, Inc., led by Prasad Anguluri, helps Homeowners Associations manage resident requests, policies, and maintenance. Context Nature, PBC, led by Ephi Banaynal dela Cruz, helps finance and tax professionals identify clean energy tax credits. Axtrolite, led by Atul Alatkar, is a stealthy startup in the real estate property management sector. Read more about the startups and founders: https://lnkd.in/gEf4agqj

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