Riley Hughes

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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Silicon Valley Slackers: Myth or Reality? We sat down with Menlo Ventures’ Deedy Das to discuss his viral tweet about underworked engineers earning $300K+ and the phenomenon’s broader implications. Mouse Jigglers & Ghost Engineers: Deedy shares wild stories of remote workers gaming the system, from "working" in Mexico for years to productivity software catching patterns of inactivity. Misaligned Incentives: Deedy argues that middle managers prioritize headcount over productivity, creating an environment where underperformance is overlooked. Measuring Productivity: Lines of code and git commits aren’t enough. Engineering productivity remains complex and difficult to quantify, so there’s no silver bullet. Viral Backlash: Deedy’s anecdotes sparked heated debates in tech, with some engineers admitting to coasting while others criticized him for "narking" on the culture. Should companies rethink how they measure and incentivize performance?

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We recently had an opportunity to gather with finance leaders based in Utah, all the way from public company CFOs to finance leaders of fast growing Series A-stage startups. It was a great discussion with a great group. A couple things stood out for me from the discussion: 🤖 A handful of these leaders mentioned that they are starting to see some tangible productivity gains from the AI in their organizations, mainly around developer productivity and getting more done with less. It still felt early, but interesting to hear anecdotes of the promise of AI being realized. ✂️ On behalf of our portfolio companies, we asked what it takes takes to sell software into their organizations given the current economic environment. Their feedback confirmed a lot of what we were hearing from our B2B portfolio companies: ▪️They are looking to consolidate vendors, it's very unlikely (if not impossible) they would approve a net new vendor unless it is replacing another tool/service they can cut from the budget ▪️ROI is extremely important. They are looking for tangible evidence that the tool will drive revenue and/or reduce costs. ▪️The mentality of "everyone gets a seat" is over. They are looking for justification for why certain teams and individuals should get a license. ▪️ They are approving every purchase. Just assume the CFO is a part of the buying committee even if it isn't obvious. Bring the CFO in early to the buying process and arm the internal champion with the ROI case along the way. Really grateful for this group for gathering and sharing their insights!

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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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About to go live... Startup Studio portfolio VC fund. $8.5 mil. with room to oversubscribe. All deals warehoused and ready to allocate. Built in equity on day 1. Low 1 time management fee. $35k minimum investment. 506c so accredited investors only. GP's are personally invested. Multi tiered exit strategy in place. Liquidity options available at year 2. *** This presentation of Sidecar Portfolio Fund (the “Company”) is for information only and shall not constitute an offer to buy, sell, issue or subscribe for, or the solicitation of an offer to buy, sell or issue, or subscribe for any securities in any jurisdiction in which such offer, solicitation or sale would be unlawful.***

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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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Did you know that YC founders get a secret weapon… and it’s not what you think. “Bookface” is YC’s internal social network. It was needed because YC had funded larger batches and the hardest part of a community is knowing who is in it and who you can trust and ask for help. On the platform, founders share real methods and advice that would break if it were shared widely It’s secret knowledge shared with a trust-first community - answering 80% of the questions a founder can have about building and selling a product, be it to clients, candidates or investors. Before the platform, if you had a B2B startup, you had to reach out cold to potential customers. Now there are over 1000 YC companies you can sell your service to and all of their contact information is in Bookface. As a result, YC alumni companies are often over 50% of your new sales during YC. It’s superpowers like this that make YC deals so attractive compared to the norm. You are investing in a founder with a 10x network already!

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What a week this has been for innovative companies in Seattle (first Smartsheet and now OctoAI). Today NVIDIA made public the news that they have acquired Madrona portfolio company OctoAI. Partnering with the founders since Day 1 (ok Day -1) has been one of the greatest experiences of my life. Luis Ceze, Jared Roesch, Tianqi Chen, Jason Knight, Thierry Moreau and Carlos Guestrin were all involved in the research and insights that helped create the TVM open source technology at the University of Washington computer science school and then the creation of OctoAI back in 2019 to drive commercial impact with this technology. From sorting out the terms of the original "pre-seed" round over a bottle of Caymus Vineyards wine to helping Amazon Web Services (AWS) understand the dynamics around the open source movement in Applied AI to learning our way in to product-market fit with the BEST inference optimization service available (OctoAI can help customers find their optimal fit of performance, customization, and cost), OctoAI has been the best! The company has helped set the table for AI-driven innovation for the years ahead and they will be a perfect compliment to the many capabilities at Nvidia. Luis, his leadership team, the board (including Carlos Guestrin Lip-Bu Tan and Mike Dauber) and so many "friends of OctoAI" know what a motivated, talented and authentic group of people are associated with this company. It is inspiring to see an acquisition at a total deal value of over $250 million in this highly dynamic and fast-moving phase of AI disruption. It is even more exciting to anticipate what will be possible with innovations powered by AI models and related technologies in the years ahead. Madrona has been investing in Applied AI for over a decade and we truly believe that we are just getting started! One of the hardest judgement calls as an investor and board member is to assess the benefits and risks of selling a company at a key inflection point in the journey. Nvidia made a compelling case that the impact for the OctoAI team and technology would be maximized within the market leader for AI infrastructure. I will be rooting every day that they all maximize this impact in the months and years ahead!

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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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Reality Engagement —— I started PHX Ventures because I want to help founders in Arizona build high-growth software companies that achieve venture scale. I can handle the good, bad, and ugly of company building. I’ve lived it. I can handle losing money. I don’t like it, but I can handle it. I can handle bad news and disappointment. Company building is a roller coaster. I can handle a changing market and new competitors. Market opportunity and market dynamism go hand in hand. I can handle co-founder breakups and key team member departures. It’s not great but it’s fairly normal. I can handle bad quarters and product problems. Stuff happens in startups. What I can’t handle is a lack of engagement with reality. Willful ignorance or disregard for data won’t make your business better. If the math of your business is telling you something is broken then it means something is broken. Let’s just fix it. And let’s fix it right now. Let's at least try. I love optimism. But I love realism even more. Broken things tend not to fix themselves. In my experience, the best founders have the highest engagement with reality. Just tell me what about your current reality is giving you angst. Tell me the problems in the business. Just tell me. Don’t sell me. Tell me. I can handle it. And maybe I can help. #founders #startups #b2b #saas

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👀 Founders who are the right fight for the Community VC forums and Iceberg 👀 The most successful founders—the top 0.1%—achieve remarkable outcomes by systematically building vast networks of investors and supporters, leveraging them for capital, promotion, and critical resources. Companies like Zeroco (raising $5m in 7 hours from 3082 supporters) and Superhuman (raising $75m off the back of a 50k person waitlist) are prime examples. However, most founders: 👉 Lack the experience, network, or structured approach to replicate this success 👉 Spend 10+ hours a week chasing support (emailing, booking meetings, having pointless conversations) with little predictability or payoff 👉 Leave untapped value on the table with their investors and advocates That’s why we’ve built Community VC as a growth engine and Iceberg, a supporter CRM designed to replicate Zeroco and Superhumans’ success by helping founders attract, nurture, and activate their first 10, 100, and 1,000 supporters. In the past 6 months we have supported 30+ companies in building their supporter base to close capital for less than 3 hours per week (compared to 10 normally) and we’re still improving. We have 100 founders working with us and 500 on our waitlist. Every week we are receiving 10+ new sign ups, with zero marketing spend so far. A recent example of ROI on 10 nurtured supporters through our ecosystem by a founder: ✅ 3 months ✅ 15 hours total spent nurturing ✅ 50 referred deals ✅ $24,500 revenue 💯 That’s $326 per hour per advocate nurtured in revenue 💯 Plus investment of $25,000 Imagine if a founder who was gearing up for a raise of any type had an army of 100 or 1000 people who could be activated at an even better ROI with an automated, personalised system... How? 👉Founders uncover investors through their own network, via Community VC and other channels by distributing their Iceberg profile links 👉The link collects supporter data and adds them to the systematised Supporter CRM 👉The founders are prompted with evolving best practice investor comms to nurture and engage the supporters for help and capital Not only are founders attracting more supporters than they ever were, they are closing capital faster and with more aligned people with Community VC and Iceberg. 🕐Why now? The future of outsized returns will come by supporting small teams who can achieve huge amounts in extremely niche sectors, with much less funding. They will achieve this through leveraging AI and leveraging their community.

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When I created Founders Game, I wanted a space to empathize with founders at my level. That's why we required founders to have either raised $1M, or generated $500K ARR to even apply. Now, we're opening it up founders at all levels. If you want to join the closed beta, leave a 2 sentence pitch of your startup in the comments below.. I'll be DMing select pitches with a link to an application.

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Successful Exit from a Failed Start-up? Sometimes, a VC's goals may not align with those of the Founder. In this scenario, there's still an opportunity. Even in Europe, more and more funds and companies are becoming interested in acquiring small, stable SaaS startups.

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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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Huge opportunity

Series A investors - if a cofounder has just left a company when you invest, what % of equity is acceptable for them to leave with? (At seed, I like to see any "dead equity" at <6% pre raise and am curious if it's higher at A since more work has been done)

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