Jeff Titterton

Love it or hate it, being in the SF Bay Area is still one of the biggest hacks for First Builders to discover huge opportunities before anyone else. But what can you do if you’re not here? Cecilia for example moved here in 2001 and instantly joined Yahoo after feeling the palpable energy around early internet. And it’s been nonstop ever since as she later joined Amazon, Cruise, Replit, and her own breakout company GC AI. She credits a lot to the emerging tech density and optimism in the Bay Area. But she also mentions additional ways people can identify these opportunities early on: - Follow intuition around big waves - Follow your envy - Never lose curiosity - Watch the teen hackers - Talk to peers early and often (builds long term networks/insights)

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The Equity team at TechCrunch put together one of the better breakdowns I've heard on the Google-Wiz close this week. If you're in enterprise tech and haven't listened yet, make 20 minutes for it. Shardul Shah (Index Ventures, early Wiz backer) reframed the deal in a way most coverage hasn't. He didn't position it as a cybersecurity story. He positioned it as what happens when AI, cloud, and security spend all converge on one company at the right moment. The part that landed hardest for me: Wiz became a $32B company because most enterprises moved to cloud faster than they built the controls to manage it. The governance layer got skipped. And then they had to buy it back at a price that made history. I support the teams who see this playing out with AI every week. Agents shipping, copilots rolling out, automation programmes kicking off — while governance, observability, and compliance are still somewhere between "next quarter" and "whose budget is that?" EU AI Act enforcement starts in August. That's not theoretical. The Wiz story is a reminder that the unsexy work — assurance, operating models, the governance no one puts in a keynote — is consistently where the value ends up. It's exactly the gap we're focused on at @OnStak. 🎧 https://lnkd.in/eE2ycW3s

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This really resonates. When Samuel Giraldo Hoyos, Rodrigo Burgos and I launched Aloi, we weren’t tax ops insiders—and that was the point. Fresh eyes let us challenge the “this is just how it works” mindset: manual workflows, fragmented data, reactive compliance. We’re rebuilding tax ops with an AI-first approach so large enterprises can become exponentially better at compliance, control, and audit defensibility. Rene Arturo Díaz García Ian Yoav Escobar #TaxOps #EnterpriseAI #FinanceOps #Compliance #Automation

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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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Last year’s Series A was a milestone, but it wasn’t a stopping point. As proof that we’ve only been moving faster than before, I’m excited to share that Numeric raised a $51M Series B, led by investors like IVP, Menlo Ventures, Founders Fund, and more. Over the past year, we've launched AI-powered flux analysis that accountants actually trust, built out cash management tooling, and worked with some of the best finance teams in the industry. This raise funds what’s next: more AI agent capabilities, building a strong finance data layer, and expanding the team. If you're interested in working on hard problems in finance infrastructure, let's talk. More on the round: https://lnkd.in/gvkWqiDx

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I'm bullish on the impact of the internet. Even more bullish on the impact of web-native, browser-native payments and the endless possibilities for builders around the world to build a true internet economy. Excited that x402 is now live on Stellar!

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The SMS interactions between brand & consumer contain incredibly rich context for 1:1 personalized commerce experiences. Postscript is the platform enabling such experiences. On this week's episode, Rishabh and I sat down with Adam Turner to explore how SMS evolved from an abandoned-cart afterthought to a 1:1 sales & marketing channel. We covered: - Category creation and the rise of the “SMS marketer” - Compliance and quality as product design principles - Moving from broadcast to conversational journeys - Building distribution in the Shopify ecosystem, then scaling a sales-led motion - Where AI has augmented vs reinvented both marketing products and teams Link in comments

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Twilio's Sam Richardson predicts that narrative and storytelling will become the differentiator for brands trying to cut through noise. Read more here: https://lnkd.in/gxZiguzq

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Don’t think of who you can replace with AI, think of what you and they could do better with AI. There are lots of intangible functions people do outside of their defined job descriptions.

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Trek.iQ is moving fast, and our latest milestone just poured fuel on the fire. We’ve secured our first investment. Early-stage startups are built on belief. Belief in the problem you’re solving, belief in the team, and belief that the work matters. Our mission with Trek.iQ is to make accessibility in public spaces more visible, measurable, and actionable. Too often accessibility is treated as an afterthought. We’re building tools to help change that. To you Lopsii Olagoke: thank you for believing in the vision and in what we’re building. To everyone who has supported Trek.iQ so far - advisors, partners, early users - this milestone belongs to you as well. If you believe that innovation is meaningless if it isn't accessible, let’s talk. Onward 🚀

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I spoke w/ Cloudflare co-founder & CEO Matthew Prince for the latest ep of the Slow Hunch podcast. Since 2010, Matthew and his team have built Cloudflare into one of the most important companies on the internet: powering and protecting vast portions of global traffic. I’ve known Matthew since Union Square Ventures’ investment in Cloudflare’s Series C back in 2013, and it was really fun tracing his slow hunch, right from those early days. We covered: - how he met co-founders Michelle Zatlyn and Lee Holloway - the early experiments and risks that shaped Cloudflare - stories from the company’s pre-IPO days - the decision to make encryption free - how their infra ended up running 2 of the internet’s 13 root servers - his thoughts on AI (esp the transition from a search-driven internet to an answer-driven one) Hope you enjoy!

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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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Essential services are under more strain and complexity than ever—but most still operate with limited visibility, reacting to failure instead of anticipating it. At BrightAI, we’re changing that. With $51M in Series A funding co-led by Khosla Ventures and Inspired Capital, we’re scaling Physical AI to bring real-time observability to the physical world—so essential services can act before things go wrong, not after. We’ve spent the past few years proving what’s possible—now it’s time to scale. Thanks to Dina Bass for the thoughtful writeup in @Bloomberg: https://lnkd.in/gisEct4G Grateful to Upfront Ventures—and especially our board member Nick Kim—for being such thoughtful, steady partners in this work, and to BoxGroup, Marlinspike, and Rsquared VC for their participation in this round. Because when the systems that support daily life run with preventative monitoring, everything else grows stronger.

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I rarely make predictions, but... No company founded after 2026 will organically grow to more than 10k FTEs. The leverage of rapid iterative decision loops by teams using best-in-class AI has reached escape velocity over traditional economies of scale.

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Founders: every rule (about fundraising and everything else) is artificial and meant to be broken. For example, consider the “rule” that the lead investor should invest at least X% of the entire round. It’s BS. For example, the amazing Kirsten Green led Bonobos’ $30m Series C round with $1m (and helped the founder raise the remaining $29m). Ignore the so-called rules. Do the right thing for your company. Be the exception.

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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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One of my favorite podcast conversations to date. Our VP of DevX and Self Service, Sanjay Sarathy, sat down with Neil C. Hughes on Tech Talks Daily recently to talk about what actually makes product-led growth work long-term. Key insight: Sustainable growth comes from doing the unglamorous work early --building trust, optimizing unit economics, saying no to vanity metrics. It's rare to hear this level of honest conversation about scaling PLG from bootstrapped to $150M+ ARR. Worth a listen: https://okt.to/3Rlsam

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AI is changing the structure of most companies we see. Lots more coming from us on how startups can build faster, leaner teams -- and where we see all of this going. Great piece from Pete Flint to kick it off: https://lnkd.in/dcUebcJj

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