William Gaybrick

🚨NEW EPISODE: Recorded live at FUTURE TITANS 2026 - Jeff Perry of Carta sat down with the iconic Seth Levine, co-founder of Foundry. Seth has been in venture for 25 years, built Foundry from scratch as an emerging manager himself, and has backed about 50 emerging manager funds through his fund of funds. He has genuinely seen every side of this table. They went deep on building Foundry, why VCs are in the influence business, not the decision business, and why the concentration problem in venture is not only bad for LPs, but also for the innovation ecosystem overall. And why Seth's new book, Capital Evolution, is so important for the future of America. 🎧 Links to listen... Apple: https://lnkd.in/ehQUQ2EM Spotify: https://lnkd.in/eU4FExpg

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Great conversations at our WillowTree Ventures dinner with leaders across fintech and AI. A few themes stood out strongly: enterprises are leaning into AI for real efficiency gains, product and engineering orgs still set the agenda, and the whitespace in “boring” industries is wider than most people assume. It’s clear that the next breakout companies in AI for financial services won’t come from the obvious places. Thanks to everyone who joined - excited to keep working alongside founders building in these non-obvious, high-impact wedges.

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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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Every hire, product feature, and GTM experiment is a capital allocation decision, most teams just don’t call it that. I’m kicking off a 3-part series on capital allocation for founders, operators, and finance leaders with a simple question: ➡️ Will the next $1 you deploy become worth more than $1? Series overview Part 1: defines the core concept + the math Part 2: where capital goes + how to measure whether it’s working Part 3: AIMS framework for communicating allocation decisions to management teams and your board Part 1 (attached here) lays the practical foundation: 🔹 The $1 invested test and ROIIC vs. hurdle rates (scoreboard vs. decision lens) 🔹 A lightweight “investment brief” to evaluate bets (GROW / BUILD / BUY) 🔹 The small metric toolkit that translates finance into operating decisions (NPV / payback / ROIIC / incremental margin) 🔹 Early-stage proxies when DCF inputs are unknowable (burn multiple + revenue quality) 🔹 Operator “vital signs” to spot drift early (profit engine, leverage, cash conversion, optics) Series Roadmap ✔️ This series (Parts 1–3): breadth-first. shared, lightweight framework to define value creation, choose decision-grade metrics, and communicate tradeoffs clearly ✔️ Next series: depth-first. momentum drivers + operational decisions that need near real-time measurement to spot drift early and course-correct fast Read Part 1 here and Part 2 and 3 on substack. Next Series will be out next week. 💰 What’s one bet you’re funding right now, and how will you prove it’s working?

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Pumped to double down on the overlooked software founders who have their head down delivering the future in their industries—especially those tired of choosing between bootstrapping or taking excessive VC $$ with boom or boost expectations. Onward!

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At Vibe Capital, we believe we're at a major inflection point. For the last 40 years, the highest-leverage work was in manipulating bits. That era is maturing into a utility. The new frontier is the physical world, and the race to program it has begun. In my latest Dave's Quick Hits newsletter, I map out the three fundamental stacks for rebuilding reality: 1. The Biological Path: Using AI to turn evolution into an engineering discipline, creating new materials and medicines at an incredible speed. 2. The Mechanical Path: Deploying AI-directed robots and self-replicating factories to trigger a new industrial explosion. 3. The Cybernetic Path: Building the final API to the brain, merging human cognition directly with our biological and mechanical creations. The generational alpha won't come from funding the next app, but from financing the means of physical creation. You can read the full analysis and the investment theses for each path here. https://lnkd.in/gAXNDaZF #FrontierTech #VentureCapital #Investing #DeepTech #AI #Manufacturing #Biotech #vibecap #vibecapital

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Don't Build a Better Wheat Farm" - Why Defensibility Stakes Are Higher in Deep Tech Just published a new piece on my "Ignore the Confusion" blog, building on thoughtful insights from Eric Ver Ploeg at Tunitas Ventures about startup defensibility. Eric's core thesis: Too many startups pitch like wheat farmers - "huge TAM, slow incumbents, growing market, domain expertise" - but fail to think through long-term defensibility until it's too late. From a deep tech perspective, the stakes are even higher: ** Unlike software, deep tech founders must commit to defensibility strategies from day one - their funding depends on it ** Patent vs. trade secret decisions are often difficult to reverse and shape your entire competitive strategy ** Even "picks and shovels" providers (the tools that make industries more efficient) become commodities without proper moats The key insight that resonates: Defensibility can't be retrofitted. Whether you're building software or deep tech, your moat must be architected into the business model from the start. Thanks to Eric Ver Ploeg for sharing these insights on startup strategy and letting me build on his framework from a deep tech lens. Read the full post: https://lnkd.in/dEj_iF-Q #DeepTech #StartupStrategy #Defensibility #VentureCapital #Innovation

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An emerging VC manager's fundraising lessons... the first two funds are a grind. Now, we’re on our third fund, it feels like we’re almost over the hump, but fundraising never gets easy for most of us. I want to congratulate the emerging VC firms presenting at this year’s RAISE Global conference. As former RAISE presenters, and (soon-to-graduate) emerging managers, we thought we’d share this LP Translator, a lighthearted guide to decoding what LPs really mean during the fundraising process. Fellow GPs, which ones did I miss? 👇 The LP Translator 📣 "Let’s stay in touch.” Translation: We’re not interested. “We want to see your track record develop.” Translation: Either we don't believe in your strategy, or we’re focused on managers with more buzz. “We’re not allocating to new managers right now.” Translation: We’re not allocating to you right now. "Show us your deals so we can get to know you.” Translation: We’d like free co-invests if you get something hot. “We need to see more DPI before we commit.” Translation: We don’t really understand VC, but we’re pretending to. “We’re fully allocated for this year; check in early next year.” Translation: Next year we’ll still be fully allocated (just not to you). “Call us before final close.”  Translation: I’m too polite to say no at this time, so I’m kicking the can down the road. “Your fund is too small.”  Translation: Okay, that one might actually be true (for some LPs). “We went through your data room and want to meet face-to-face.” Translation: We’re genuinely interested, keep going! “Can you send us your LPA for signature?” Translation: Let’s go! 🚀 -------------------------- Fundraising is a long game, longer than we ever expected. We're now seeing how LP relationships are built across several funds, not several months. If they’re investing time to learn about you and your strategy, that’s your best signal of real interest. #emergingmanager #venturecapital #LP #RAISEGLOBAL

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Big milestone for Firmable. We’ve raised $14m Series A led by Airtree. Sales has moved through a few big waves: intuition-led, CRM-led, data-led. We’re now entering the next one – intelligence-led sales. The opportunity isn’t just better data. It’s turning that data into clear direction and action, without adding more work for sales teams. That’s what we’re building at Firmable: a foundation of trusted external data, layered with intelligence that helps sellers know who to focus on and when. Led by Airtree, this round supports our expansion across Asia and into the US – and accelerates the build-out of AI agents that take the admin work off sales teams so they can focus on what they do best. Proud of the team, grateful to our customers and investors. We’re just getting started. Read the exclusive in the AFR. https://lnkd.in/gr66uknb Leigh Jasper | Tara Salmon | Karthik Venkatasubramanian| Chester Thompson| Chath Widanapathirana

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Dayna Grayson is a leading VC who has “sat in every chair” at a young age. She founded Construct Capital with Rachel Holt, an early leader at Uber. Together, they are tackling the digitization of industry. Dayna will discuss macro trends, what it takes to be a founder, and the potential for AI. She is one of the few who have successfully blended a career of operations and investing.  Check out our discussion at: https://lnkd.in/eYBUGjbW #leadershipdevelopment

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💡Emerging GP Fundraising Insight #8: Rolling Closes Keep You Moving Small funds can't always afford to sit still until the target is hit. Rolling closes let you start deploying earlier, build a track record, and show momentum to prospective LPs. One GP told me that for Fund I ($5M target), he took capital as it came, signed, wired, and got to work. It wasn't perfect, but it kept the lights on and the deals moving. Sometimes the "sign and wire as it comes" approach is the only way to get moving. Takeaway: Momentum is a fundraising asset and rolling closes can help you keep it. Has anyone here used rolling closes as a strategic advantage?

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If you know... A 10x engineer Who loves the speed and intellectual challenge of early stage but also Wants job stability and Equity diversification then This is the one job that checks all of their boxes

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Two weeks ago on Swimming with Allocators, we sat down with David Clark, CIO at VenCap, to talk about what decades of venture data can teach allocators. One takeaway that stood out: discounts don’t matter as much as people think in venture secondaries. Because venture is such a power-law asset class, outcomes are driven by exposure to a few massive winners. Whether a stake is bought at a small discount, or even a premium, often matters far less than the quality of the underlying company and its upside. Great conversation on venture returns, manager selection, and the nuances of how allocators should think about secondary investments. 👇 Link in the comments.

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Summary: The venture firm CRV has raised $750 million for its 20th flagship fund, which will focus on investing in early-stage startups, particularly in the consumer and devtools sectors. Key takeaways: CRV's new fund is smaller than their previous one, but still received strong demand from investors. The firm has a history of successful investments, with 80 startups eventually going public since its founding in 1970. CRV is shifting its focus away from late-stage rounds, citing lower overall returns, and towards seed and Series A investments. Counter arguments: Some may argue that CRV's decision to not raise another late-stage fund could limit its opportunities for growth in the future. The success of the new fund will ultimately depend on the performance of the startups it invests in, which can be unpredictable in the volatile tech industry. #venturecapital #fundraising #startups https://lnkd.in/g8d-N9jX

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Our WillowTree Ventures dinner brought together an incredible group of fintech and AI operators. What struck me most was the consistency across perspectives: AI is finally unlocking tangible value in workflows, personalization is becoming real, and some of the biggest opportunities sit in the corners most people overlook. Founders building for financial services and enterprise AI deserve more conversations like these. Grateful to everyone who made time, and if you’re tackling one of these “non-sexy but massive” markets, let’s talk. Here are some key takeaways - AI is still about efficiency. The most serious near-term initiatives focus on automation, workflow augmentation, and operational leverage across teams. - Tech orgs continue to control the AI agenda. Budgets and decision-making largely sit with product and engineering, who are driving both exploration and implementation. - Personalization at scale is becoming real. There was broad agreement that AI can finally enable true 1:1 experiences in products and services, not just improved segmentation. - The most interesting opportunities are in “boring” corners. Non-traditional and overlooked segments are wide open for AI. “Non-sexy is sexy” may define the next wave of category creators. - Crypto is still early in the enterprise. Despite broader excitement, real day-to-day adoption remains nascent and uneven.

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I recently joined Tim Tonella on the VENTURE 2 VICTORY podcast for a thoughtful conversation on where we are in the software cycle. Find the full episode here: https://lnkd.in/gdSGXXDZ

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Thrilled to announce our investment in CtrlB! Privilege partnering with founders like Adarsh, who are deeply obsessed with the problem they’re solving - a true force of nature. CtrlB is redefining enterprise observability, building a next-gen telemetry engine that makes search up to 10x faster and 90% cheaper. In an era where enterprises generate terabytes of data every day, CtrlB is closing the gap with a fundamentally new approach to ingesting, indexing, and querying petabyte-scale data - enabling teams to gain real-time visibility without trade-offs between cost and speed. #funding #startups

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I spoke with Christien Louviere of BDE Capital about his journey from a $330mm exit to becoming an independent sponsor. Christien shared excellent insights for folks looking to partner with business owners, rather than buy sellers out completely. Below are a few of the topics we covered: - Why he moved from “zero-to-one” startups to a buy-then-build strategy - How Christien's background shaped a focus on growth vs. cost-cutting - Why 20–40% rolled equity is central to his deal structures—and how it builds trust with sellers - Using scenario analysis with AI tools to evaluate management teams and uncover hidden key-person risks - How to identify when a $3–5M EBITDA company truly has a middle management layer—or is still founder-reliant For anyone investing in or buying small businesses, Christien’s approach provides a fresh lens on growth, alignment, and deal structuring. 🎥 Watch the full interview here → https://lnkd.in/ekfkaiej 🎧 Listen on Spotify: https://lnkd.in/e86Agx6V

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