John Cowgill

Kettleborough VC has been active for ~6 years, invested in ~30 companies, gone through ~80 funding rounds, witnessed ~12 exits including ~4 instances of partial principal erosion, seen ~4 seed to $100M journeys, tracking ~29% XIRR across the portfolio. A couple of IPOs from the portfolio surely seem very much in line ahead.

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Exciting news! We just sent out the inaugural newsletter for Future Frontier Capital, our pre-seed venture fund backing frontier tech startups. As I hit "send," I realized how launching FFC parallels the path of the founders we support. Starting FFC has required the same passion, perseverance, and self-belief that drive entrepreneurs. Just like a startup, getting a VC fund off the ground demands relentless hustle—building the brand, perfecting the pitch, and networking tirelessly. There are constant challenges that test your resolve and endless hours of unglamorous work behind the scenes. And perhaps most daunting - the self-doubt, wondering if you're crazy for attempting something so bold. Pushing through that negative self-talk requires unshakable faith in your mission. Raising this VC fund reminds me of starting our IP strategy and patent analytics firm two decades ago. It’s a powerful reminder of the perseverance, creativity, and resilience needed to turn an ambitious idea into reality. This experience makes us more empathetic partners, ready to support the founders we back. Our work is just beginning, and this inaugural newsletter underscores our commitment to supporting frontier tech startups every step of the way. #startups #VentureCapital #EmergingManagers #Entrepreneurship #InnovationMindSet

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I recently saw this metric from Carta’s 1Q24 VC Fund Report, which is very concerning. DPI... is nowhere to be found in earlier vintages that probably should start showing DPI. Funding early-stage projects is great, but ultimately, these venture dollars need to exit their investments and pay back their limited partners. That’s where the metric Distributed to Paid-In Capital (DPI) comes in. While managing a fund, we get interim measures during the life of the fund (e.g. IRR, MOIC), but ultimately, “you can’t eat IRR.” If you want to build a lasting venture capital organization, you need to start showing DPI for your fund. Keep in mind that this is traditional VC data from Carta, and is not strictly crypto venture. Crypto venture tends to get liquidity earlier (tokens) and things tend to go parabolic sooner (faster, more unicorns) - but I’d wager that the data here is somewhat similar for Crypto VCs… Not as much DPI as there should be from these earlier vintages. Read the full article, as well as a recap of all the crypto fundraising rounds for August, here: https://lnkd.in/g3eVJ-iF

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Want a front-row seat to the frontier of tech? We’ve got the role (or two) for you! We’re expanding our frontier-tech team at Blackbird by hiring a Frontier Tech Investments Associate and Foundry Fellows! Got questions? We've got answers... 1️⃣ What are the roles? 🧪 Associate = a full-time VC investment gig in our Blackbird Investments team, working directly with me. We’re looking for someone with a science and/or engineering background and more curiosity than they can handle. You’ll grow your own investment brand and practice, support our portfolio founders, and will help build Foundry, our early-stage frontier-tech accelerator. ✨ Foundry Fellow = a casual/contract gig in our Blackbird Investments team, ~15h per week for 3 months. The Fellowship is ideal for PhD students and ECRs who want to learn more about startups and VC. You’ll go deep on emerging areas relevant to your expertise (or curiosity!), get a front-row seat to groundbreaking companies in those areas, build out your non-academic network, and develop a solid writing practice. 2️⃣ Why are you hiring? We love frontier tech, and we’re ready to grow our team. 3️⃣ Wow, it’s so great that you’re starting to look at deep tech! Look, we get it: we don’t make a lot of noise about our frontier tech investing. Buuuut we’ve been deep-tech investors since we backed Tim Kentley-Klay to found Zoox back in 2014—we’ve been on incredible journeys with PsiQuantum (building the world's first utility-scale quantum computer right here in Australia!), Inventia Life Science (transforming drug discovery with high-fidelity cell models), Remedy Robotics (surgical robots for remote endovascular procedures), Opto Biosystems (minimally-invasive neural implants to treat cancer), and more. We believe that frontier technologies, and great frontier-tech investing, will be part of the solutions to the greatest problems humanity faces today. 4️⃣ When do applications close? May 31st at 11:59pm AEST. 5️⃣ I have more questions! I’m sure you do! Clare Birch and I are hosting an AMA to answer any and all questions about these roles. Want to know what a week in the life of our team looks like? What’s keeping us up at night? What our ideal candidate looks like? Come along and find out - registration link in the comments 👇 Apply for these roles: Associate - https://lnkd.in/gCfj4EUJ Foundry Fellowships - https://lnkd.in/gj6ATZVZ If you know anyone that we should meet, send me their details! Cameron Elise Ben Andrew Robin Joseph Adelaide James Olivia Lucinda Raghav Jesse Christie Mohamed Tom Amee Pablo Haya Loong Hon Joshua Benjamin Megan Harry Denzil Matthew Diana Daniel Tom Deanna Justin Amar Lilly Stone Thomas

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A new era of deep tech has emerged. First time funds will raise “unheard of” amounts of capital to fuel next gen deep tech startups - producing outsized, superior returns for LP’s compared to the rest. Prudent investors will act on this data and shift investment strategy as LP’s or risk being left behind savvy wealth managers and CIO’s / FO’s who saw this trend begin 4 years ago.

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Ross Haleliuk posted the fantastic article below. This is the world where I live day-to-day. At TechOperators, we invest mostly in early-stage cyber, but we do things a little differently, and we believe there are ways to invest successfully outside of pure Power Law math. The article argues that many security problems are too small for VC. I agree. I often try to convince bootstrapped founders not to raise venture because doing so can turn a successful, slow-growing bootstrapped company into a failed venture-backed company because, despite a large infusion of capital, it couldn't double every year. VC is not monolithic--not by stage, strategy, or style. Venture is often equated with "Tier 1 Venture". Ross argues that VC is not always great for early-stage cyber--and he is right. Bootstrapping AND VC work when incentives are aligned. Does it work for an early-stage VC with a <$200M fund to invest in several early companies at reasonable valuations, setting up the conditions for reasonable exits that pay off for both investors and founders? Yes. Does it work for $800M funds investing in seed stage at $100M+ valuations? Well, that depends! Power law says it does (for VC), but the unfortunate externality is that these rounds destroy companies and founder equity more often than not. There is a role for patient capital in this ecosystem to fuel successful companies that retain exit optionality as they scale--driving exit value for both founders and investors.

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Insightful breakdown from my great Partner Omri Amirav-Drory on the simple factors that really separate the top 1% of investors from the rest, and how more operators should become investors! https://lnkd.in/gEiZdT2h

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The state of venture capital is wild right now. We are witnessing a surge of innovation across the spectrum: - Funds merging - VC doing PE - PE doing VC - Secondary funds - Buyout funds - Spin-out funds - Debt funds - Continuation funds - Infrastructure funds - GP turnover - Hard Tech surging - Family Office uptick

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DeepCast shipped a number of really cool new features recently in advance of a broad outreach push to podcast listeners. One new feature is our new Daily DeepDigest tool that sends you a concise daily email including any new episodes from the trailing 24 hours from any podcasts you Subscribe to (on DeepCast). Think daily podcast cliff notes or podcast news ticker tape, with a hint of Morning Brew various brews or PitchBook News—it's increasing information throughput when you're pressed for time. And this feature is rapidly evolving to distill other key extractions from shows you're already interested in, but also exposing you to other shows you might be unfamiliar with that also have nuggets to share—and thus increasing your aperture yet still conscious of your time. Want to go deeper on any given episode? Click the episode detail and you're off to an episode on DeepCast, where you can subsequently read a longer form distillation of that episode or go straight to the source and listen to the episode. (And podcaster friends, these pages are definitely increasing indexing and thus Google entry points to your shows!) I'm loving this feature as a user, personally. Can't wait to see what others think! #BuildingInPublic #Podcasts #AllTheWorldsInformation #HowYouWantIt

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As a VC, there are times when you have to choose between prioritizing returns and supporting the founders you work with. It’s not easy because we have a fiduciary duty to our LPs, which, in our case, are primarily non-profits, to maximize returns. At Eniac, we play the long game: if we do what’s best for our founders, it will ultimately benefit our brand, reputation, and relationships, which will be best for our LPs in the long run.

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Despite the headwinds many software companies (even public ones) are facing today, there are still those that are delivering great results. Check out how the top decile companies in our Beyond Benchmarks survey are performing. And don't forget to review the full report for many more insights on the state of private software businesses.

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Today, GTMfund’s is excited to announce to launch of Operator, its first incubated company. Max Altschuler (founder of GTMfund) teamed up with co-founder Adam M. (design engineer and 0-1 builder) and co-founder Mark Kosoglow (Outreach employee #1 and former SVP of Global Sales) to create Operator.ai alongside an insanely talented team Pleasant Middelhof, Jeremy Jonas, Carl Gunderson. We've entered a period called “The Great Ignore”. Spam and irrelevant, poorly-automated outbound campaigns are running rampant.   Operator gives you an easy-to-use Growth Engineer that allows you to build and enrich lists with accurate data, and run experiments and queries using AI to generate highly targeted outreach.    Check out their website to get updates, early access, and see how they are taking the world back to 2 touches meant to attract buyers into conversations that convert, instead of 20 touches meant to make sure you hit your activity number: https://www.operator.ai/

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Founders, besides valuation and terms, board members can make or break your company so make sure you factor that in when selecting your next investors. #Governance #VC #BoD

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✨ Breaking: Category Ventures Announces New Fund.- Category Ventures Category Ventures is a $160 million venture capital fund launched by Villi Iltchev. The fund focuses on pre-seed and seed-stage startups in enterprise software applications, infrastructure, developer tools, and artificial intelligence, with investment checks ranging from $1.5 million to $5 million. https://lnkd.in/dbw8mY6h Please share to let other #Founders know For the ❤️ of Startups #Fusion42 #Startups #Venturecapital

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A bit of a tribute to founders / humbling reminder for investors at the start of '25: I've looked at thousands of early-stage fundraising decks over the past two years. In stereotypical fashion, I can typically tell within 30 seconds (2-3 seconds per slide) if I'm going to dig in, and if it's a company I'd be interested in investing in. Over the last two months I have been working on a project with a really cool company who is raising a Series A. I've been supporting on building the deck, data room, etc. So I've been fully back in the early-stage operator seat. And let me tell you. It is SO MUCH HARDER than investing. I sent the deck to some investor friends for feedback. I really value their opinion. Their feedback was stuff that I tell founders all the time about their decks. But I flat out missed it when putting this deck together. Startups are so much easier said than done. It's really hard being in the arena. Founders live there every day. Cheers to you.

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In addition to building our own VC practice at AAF Management Ltd., we’ve invested in 37 VCs since 2017. Here is what, I believe, it takes to build a multi-vintage, early-stage, venture franchise: 𝟭- 𝗦𝗵𝗼𝘄 𝗙𝗼𝗰𝘂𝘀: hyper-focused GPs build longevity and consistency in their businesses. If you pitch LPs saying you will invest in early stage consumer but end up doing late stage consumer that’s a massive red flag. Stay germane to your mandate and strategy. 𝟮- 𝗔𝗿𝘁𝗶𝗰𝘂𝗹𝗮𝘁𝗲 𝗮 𝗨𝗻𝗶𝗾𝘂𝗲 𝗩𝗮𝗹𝘂𝗲 𝗣𝗿𝗼𝗽𝗼𝘀𝗶𝘁𝗶𝗼𝗻: the market is crowded with venture firms, articulate your differentiated value proposition to LPs and founders. Don’t try to be everything to everyone. Focus on 1-2 value propositions to your stakeholders and execute them with excellence and defensibility. 𝟯- 𝗚𝗲𝘁 𝗕𝗲𝘁𝘁𝗲𝗿 𝗮𝘁 𝗦𝘁𝗼𝗿𝘆-𝗧𝗲𝗹𝗹𝗶𝗻𝗴: we tell stories everyday. Raising capital for a fund and building your venture firm requires that same story-telling skillset. Tell consistent narratives to the market to help build your own brand as well as your firm’s brand. 𝟰- 𝗟𝗲𝘃𝗲𝗿𝗮𝗴𝗲 𝘆𝗼𝘂𝗿 𝗦𝘂𝗯𝗷𝗲𝗰𝘁-𝗠𝗮𝘁𝘁𝗲𝗿 𝗘𝘅𝗽𝗲𝗿𝘁𝗶𝘀𝗲: if you possess subject-matter expertise in a certain vertical, domain or industry, you already own a defensible moat. Accentuate that to your advantage when building your firm, raising capital from LPs and winning deals from founders. 𝟱- 𝗠𝗮𝗶𝗻𝘁𝗮𝗶𝗻 𝗮 𝗖𝗼𝗹𝗹𝗮𝗯𝗼𝗿𝗮𝘁𝗶𝘃𝗲 𝗡𝗮𝘁𝘂𝗿𝗲: early stage venture is a highly collaborate asset class. Keep your ego at the door, you will never be able to do everything it takes to build a firm alone. Leverage LPs, partners and founders for deal flow sourcing, diligence and overall industry best practices. 𝟲- 𝗙𝗶𝗻𝗱 𝘆𝗼𝘂𝗿 𝗣𝗿𝗼𝗱𝘂𝗰𝘁-𝗠𝗮𝗿𝗸𝗲𝘁-𝗙𝗶𝘁: in quintessential startup vernacular, ideally find your product-market-fit by the time you launch your second fund. You need product-market-fit before you scale your AUM, grow your team and carry more fiduciary responsibility. 𝟳- 𝗞𝗲𝗲𝗽 𝘆𝗼𝘂𝗿 𝗣𝗮𝘁𝗶𝗲𝗻𝗰𝗲: early stage VC investing is a marathon. Patience will reward you personally, professionally and financially. Build mental, physical and psychological stamina to endure the inherent ebbs and flows of your entrepreneurial journey. 𝟴- 𝗧𝗵𝗶𝗻𝗸 𝗟𝗼𝗻𝗴-𝗧𝗲𝗿𝗺: early stage VC investing is the archetypal long-term financial asset. Think in 10 year increments for your firm’s grand vision, think in 4 years for a given fund’s investment period and think in quarters when reporting material updates on your portfolio to your LPs. 𝟵- 𝗛𝗮𝘃𝗲 𝗙𝘂𝗻: if instant gratification, short feedback loops and a constant need for reaffirmation is what you are looking for in a career then early stage VC investing will not fulfill you. Have fun building, and as Naval Ravikant once said: "𝙗𝙚 𝙖𝙣 𝙤𝙥𝙩𝙢𝙞𝙨𝙩𝙞𝙘 𝙘𝙤𝙣𝙩𝙧𝙖𝙧𝙞𝙖𝙣." Finally, and most importantly, be authentic and true to yourself. #firmbuilding #entrepreneurs #VC

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