James Kawas

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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Seed fundraising hasn’t gotten easier. After reviewing thousands of early-stage companies, one pattern is obvious: most founders don’t fail at seed fundraising because their idea is weak — they fail because they misunderstand how seed rounds actually get done. 👉 That’s why we put together the LvlUp Ventures Guide to Seed Fundraising. It’s not a hype piece. It’s the exact mental model we see strong founders use when they raise efficiently and get back to building. Some of the core takeaways: 🔹 Raise when you have momentum you can explain, not just a polished deck 🔹 Size your round to buy 12–18 months of real progress — not optionality theater 🔹 SAFEs and notes are tools, not shortcuts; understand how they compound dilution 🔹 One committed investor changes everything — momentum beats perfection 🔹 Speed and clarity matter more than squeezing every last point of valuation 🔹 The goal isn’t “winning the round” — it’s setting up the next phase of the company This is the guide we wish more founders read before starting outreach — not halfway through a messy raise. 👇 Question for founders raising right now: What’s been hardest for you — getting in touch with investors, structuring the round, or keeping momentum once conversations start? 👇Want the Full LvlUp Ventures Guide to Seed Fundraising? 👍 Like this Post 💬 Comment “Fundraising” ✅ I’ll DM you the guide and share next steps to get reviewed by LvlUp’s Investment Committee and our 25+ VC partners. #Fundraising #VC #Startup #Seed #EarlyStage #VentureCapital #StartupFounders #Founders #RaisingCapital #Startups #SaaS #Tech #CPG #B2B #Entrepreneurship #BuildInPublic #FundraisingTips #VCInsights

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I’m thrilled to officially announce our $3M seed investment in Propel People, a company we built inside the 1848 Ventures studio to tackle one of the biggest challenges facing the #construction industry today: the skilled #labor shortage. For small and medium-sized contractors, hiring isn't just a challenge. It's the number one threat to their growth, profitability, and safety. With 94% of contractors struggling to find qualified workers, it’s clear that traditional hiring methods aren't built for the trades. That’s why we built Propel People. It’s a mobile-first, AI-powered hiring platform designed for how construction actually works: in the field. By leveraging smart candidate ranking, instant #SMS-based screening, and a fully #bilingual interface, Propel helps contractors build great crews faster and more efficiently. I’m also thrilled to formally announce that industry veteran Dexter Bachelder is at the helm as CEO. Having worked with Dexter and the team over the last few months, we've already seen the impact of his leadership. His 25 years of experience scaling construction tech companies will be instrumental as Propel People enters this initial stage of growth. This investment reinforces our core thesis at 1848 Ventures: building AI-native companies that solve fundamental pain points for the #SMBs that form the backbone of our economy. A huge congratulations to Dexter and the entire Propel People team on this milestone. We are incredibly proud to partner with you to support the people who build our world. Read the full announcement below. #constructiontech #venturecapital #seedfunding #ai #skilledtrades #smb

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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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I’m thrilled to announce defy.vc’s investment in Birches Health as part of their $20M combined Seed and Series A funding round, alongside incredible partners like AlleyCorp, General Catalyst, Will Ventures, and others. As someone deeply passionate about backing companies that tackle important problems for our society, I couldn’t be more excited about what Birches is building—a national virtual clinic dedicated to treating gambling addiction and related behavioral disorders like gaming, sex, porn, and internet addictions. What excites me most is Birches’ innovative health assurance model: proactive, accessible, and affordable care that’s evidence-based and delivered right at home. With the explosion of legal sports betting—think nearly $1.5 billion wagered on this year’s Super Bowl alone—we’re staring down a looming public health emergency. Traditional options like hotlines or generic therapy fall short for this high-acuity issue, but Birches changes that by offering specialized therapy from trained clinicians, multimodal treatment, and peer support, all covered by major insurers like United Healthcare, Cigna, Aetna, and Blue Cross Blue Shield. It’s available in all 50 states, breaking down geographical and financial barriers that have left so many without help. The impact is already profound: 96% of patients report an improved quality of life, and 94% give Birches a 5/5 rating. By partnering with state governments, payors, and policymakers, Birches is pushing gambling addiction into the spotlight of behavioral health conversations, where it’s been neglected for too long—often leading to shame, worsened outcomes, and higher suicidality risks. This funding will supercharge their growth: expanding the provider network, boosting clinical excellence, scaling infrastructure, and deepening insurance and state partnerships to meet surging demand. Very excited to partner with Elliott Rapaport and the entire Birches team! See more about our POV in the blog post linked in the comments. #GamblingAddiction #BehavioralHealth #HealthTech #VentureCapital #Innovation

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Fundraising isn't dating. It's a sales funnel. And most founders don't track it, so 3 months go by while they're still "in conversations." Here's the brutal math (seed round, current selectivity): 100-200 investor outreaches → 15-20% reply rate → 15-30 first meetings → 5-10 partner meetings → 1-3 term sheets → 1 close If you're not tracking conversion at each stage, you're not fundraising. You're hoping. Founders who close faster don't have better luck. They have better systems: 1. They track the funnel weekly Where are leads dying? Outreach, first meeting, partner meeting? Each bottleneck has a different fix. 2. They iterate the narrative Every week: one sharper answer to the question that killed the last meeting. 3. They batch meetings 10 meetings in 2 weeks beats 10 meetings over 2 months. Compression creates urgency. Urgency creates leverage. 4. They treat "no" as data A fast no is worth more than a slow maybe. It frees you to find the real yes. If your fundraise feels stuck, stop asking "Who else can I talk to?" Start asking "Where is my funnel breaking?" I stress-test fundraising packages for founders. Deck, model, cap table, assumptions. You get a written findings memo and a 90-minute call showing you what breaks before investors do. Link in comments. #fundraising #seedstage #venturecapital #startups

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Over the past few years, fundraising has become significantly tougher, especially for smaller funds. This, unfortunately, is the case even for VCs delivering solid returns. In my recent Crunchbase piece, I talk about how emerging managers can survive (and even thrive!) in a challenging fundraising environment. I discuss why the process today is more about familiarity than performance, and highlight places where managers should look for capital that others ignore. Check out the full column via link in comments. Curious to hear from other managers who have recently raised successfully. Which part of this rings true?

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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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Founders: At seed and A, pick your VC partner based on who can increase your odds of success the most. After that, optimal combo of brand + dilution can become the dominant factor. But at seed + A, a lead who can be a strong sounding board, can help recruit an exceptional team, someone who’ll be there for you through thick and thin does matter.

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If you’re going to raise capital, please for the love of sanity know what round you’re in. “But Shuaaaannnn we have a team and an MVP for our AI for dumpling yield optimization. We're raising seed.” Great. What traction do you have? Idea stage with a dumpling wannabe MVP? Thought so. Every founder thinks they’re raising seed the moment the product sort of works and their cofounder stops crashing the demo. But that’s a passion project with a GPU bill. Not seed. Investors specialize by stage for a reason. If you're raising seed, you should talk to seed investors. But before you do that, it helps if you’re actually… you know… at seed. Because a typical seed company often looks more like this: About $250k+ in monthly GMV for marketplaces. About $30k+ in MRR for SaaS. Meaning people are using it. People are even paying for it. And they are coming back for it. Not: A landing page. A Notion roadmap. A waitlist full of your friends. And a pitch deck with a very confident TAM slide. The round you’re raising isn’t what you call it in the headline of your deck. It’s what the numbers say it is. #startup #founders #venturecapital

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