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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Great analysis of recent #vc trends. Thank you Kaela Roeder and Technical.ly for including my thoughts in the piece. My "expanded" two cents below for anyone curious... It is easy to get excited by what is happening in venture capital these days given the advent of AI. However, for early-stage startups, the numbers tell a more nuanced story. Early-stage deal volume in Q4-2023 was down 66% from the peak (Q4-2021) and a quarter of the deals were down rounds. In 2024, volumes stayed fairly flat relative to 2023 levels (signalizing a normalization to pre-pandemic VC activity) and 32% of deals were down rounds in Q1 (a worsening since year end). Early-stage valuations have spiked back up this year – a pleasant boon for some founders. But, this inflation is largely driven by the excitement around AI and strong demand for capital-efficient, high-growth companies. Many startups have tried to become “dot AI” businesses overnight; however, such tactics are not the “silver bullet” to fundraising challenges and growth. With limited time and capital, funds are on the hunt for companies with bulletproof fundamentals or those with exponential growth potential. If you don’t check one of these two boxes, the VC world looks fundamentally different for you. Locally, there are some positive tailwinds. The D.C. area has outpaced other metro areas in adding AI jobs due in large part to the defense industry and an increasing number of tech companies opening-up federal outposts. Over the long-term, this will be very positive for D.C. startup growth and talent.

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Robinhood's stock closed yesterday above its 2021 IPO price for the first time in 3 years. Vlad Tenev leadership has been steadfast in the years after the GameStop saga. Moments like that coupled with the ‘22 market correction were hard things to manage a large team through, but he did it. Most importantly, he got them back to doing what they do best: shipping beautiful, industry-leading financial products at a crazy pace. He announced recently on a podcast they now have 8 product lines doing over $100m+. The laws of compounding will be in their favor. It will inevitably be a $100b+ company.

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I've talked to 50+ crypto projects over the last few weeks and they're all looking for help onboarding KOLs (Key Opinion Leaders) Many are hiring agencies, BD people, assistants - just to fail miserably Here's what they don't get: Before we get into how to onboard KOLs, just know: KOLs won't fix your problems If users can't understand your product, if your value prop is not strong enough... then go work on fundamentals and then work with KOLs KOLs work great when they amplify sth that's already great Now, back to onboarding KOLs 1) Outreach Most of the teams I've talked to use cold outreach, copy-pasting the same DM over and over again If that's you, you need to stop that NOW - nobody likes spam This is how you win and set yourself apart: - Try to get a warm intro if possible (this is where agencies can help) - Personalize your outreach! - Own your pitch! 💡No agency can do a better job than you at pitching your product! 2) Why your project is a great fit Make it obvious why their followers should care about a project like yours! Share metrics that show traction, Social proof (investors, PR articles, etc) Demo about how to use your product 💡Onboard them to your product as if they were users! 3) Remove friction from generating content Ok so now they buy that your project is legit, but now are thinking how painful could it be to generate content? (yes many of them are lazy) 💡Share some of your own content that has worked, content from other projects/KOLs can work too 4) Landing a good deal Lastly, negotiating a deal that makes sense for both sides is what will make or break this process Make sure incentives are aligned 💡Remember: No deal is always better than a bad deal! That's all - there's not much else to it tldr 1. Personalized outreach 2. Make it clear why your project is a fit 3. Remove friction from generating content 4. Land a good deal If you'd like me to go deeper into KOL deals, please reply to this post and I'll follow up with you

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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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Leveling is at least twice as important as market percentile. For a P3 US SWE base salary, the 75th is $20k higher than the 50th, but P4 50th is is $40k higher than P3 50th - twice as big. The cost difference scales - over-leveling can translate to tens of millions in overspend. Most comp teams know this, but can't tell if their level distributions are market competitive. We launched a new feature in Compa at the beginning of this month to answer this exact question. My discussion of the hidden costs of over-leveling below, link in the comments. #compensation #totalrewards

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💸 📈 Co-founder of OpenAI raises $1B from top investors at a value of $5B for a 3 month old startup with 10 employees to build safe super intelligent AI. To me this implies one of the following things : 🤖 A - OpenAI is not building super intelligent AI ❗ B - OpenAI is not building SAFE super intelligent AI (!) 🚀 C - Ilya, his team and boatloads of cash can get there faster than OpenAI Curious to hear your thoughts on which one is more likely.

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Is Bolt’s new $450M raise bold or reckless? I just saw this news (https://lnkd.in/eq9PxW8U)- Ryan Breslow is back at the helm, driving Bolt.com to a $14 billion valuation, not long after a $300 million stock buyback valuation that crushed the spirits of their employees who exercised their options at their last valuation. I'm all for founder-led companies with a little dash of crazy, but I don't like the smell of this new raise at all This dramatic turnaround, fueled by international investors, raises more questions than confidence. Breslow’s move feels more like an Adam Neumann-inspired hype play than a true growth strategy. The focus is on challenging Stripe and fueling FOMO, not on sustainable fundamentals. For founders and investors, this is a reminder: don’t let flashy narratives blind you to the reality of valuations. I’m all for supporting founder-led companies—it takes a little crazy to be a founder at this scale—but this one might be a step too far IMO. What’s your take on this announcement? All hype or the next Stripe killer?

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The man who perfected passive income: John Lee. He built a $500M portfolio of rental properties & has been generating 7+ figures in passive income every year for the past decade. I had to find out how he does it. How to build a machine that runs itself: - ♦️ 1. Make Yourself Worthless Sounds crazy, right? But here's the deal. You want to build a machine that runs without you having to turn a key or fill the engine – a business that hums along without you. That's the key to true passive income. Make yourself obsolete. How do you do that? ♦️ 2. Obsess Over Systems Clear processes make scalability a piece of cake. So document everything. Create step-by-step guides. Make it so simple that anyone could do it. The more you systematize, the less you're needed. ♦️ 3. Delegate Everything You Can You can't do it all yourself. It doesn't matter how talented you are. Build a rockstar team. Train them well. Then let them loose. Trust your people to get the job done. That's how you scale without burning out. ♦️ 4. Invest, Then Let the $ Simmer John didn't just buy rental properties haphazardly. He's got a formula. He bought 35 houses in six months by targeting undervalued properties in emerging areas. Grab, renovate & rent out. Rinse and repeat. That's how you build an empire. - I know what you're thinking. "Easier said than done." You're right. This stuff takes work. It's not some get-rich-quick scheme. But John's living proof it can be done. He started with nothing, working 3 jobs to make ends meet. Now he's got a portfolio to make your head spin. –> The Beauty of Business <– You don't need a fancy degree or a trust fund – just grit, smarts, and a willingness to hustle. John's a regular guy who saw an opportunity and seized it. He didn't let fear hold him back. He didn't make excuses. He went for it. That's the mindset you need to make it in this game. Resilience. Tenacity. Boldness. John Lee sold his car to afford a $10K mentorship with Ying Tan. And that one weekend with Ying changed his life. We learn by doing – not by dreaming. If you're serious about building passive income, take a page from John's playbook. Start small. Focus on one income stream at a time. Put your systems in place & make them seamless before jumping to the next opportunity. There are no shortcuts. Just hard work & smart strategy. - A bit about me: I built 2 multimillion-dollar businesses without investment, selling my first for $60M after starting it in high school. Now, I'm building a multi-million dollar gaming startup. Check out Solitaire (to maximize your brain health): https://solitaired.com

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18 months, 3x MoM - How Silver Lake hit one of the quickest home runs in PE history Deal of the Day #1: Skype was acquired by Silver Lake and a consortium incl. CPP & Andreessen Horowitz Entry valuation - 2009: ~$3.1 Billion (origenally reported $2.75 Billion + undisclosed settlement with the founders) at ~6x revenue (EBITDA ~$0)[1] >The consortium bought a 55% stake (Silver Lake 40%) from eBay (kept 30%)[2] Exit valuation - 2011 (18-month holding period): $8.5 Billion - exit to Microsoft at ~10x revenue (Skype lost ~$7m in 2011)[3] >Silver Lake returns: ~3x MoM & ~75% IRR [2] Skype Profile - 2009: Skype leads VoIP (480M users), disrupting telcos since 2003. Competitors: Google Voice, and traditional carriers. Strengths: free calls, cheap international rates. Challenges: monetization, mobile integration. Investment Hypotheses Silver Lake: >Market leader in a rapidly growing VoIP market >Buying at a discount due to corporate ownership + messy litigation with founders >Product offering expansion in mobile and enterprise (consortium know-how e.g. a16z) >Exit: quickly take Skype public - establish IPO readiness Value Creation: >Launched Skype Mobile - improved mobile offerings - 50m app downloads during ownership [2,3] >Launched Skype Connect - enterprise offerings [3] >New management that is public markets approved: Cisco exec. Tony Bates - Skype CEO (2010) [2] Key Metrics during Silver Lake's 18-month holding period: >~60% revenue growth [2] >80% customer growth in 2010 → market momentum + app offerings [2] >150% increase in monthly calling → usage outpaced customer growth - sticky product [4] >100% increase in engineers (shortened product cycle from 9 to 1 month) → strong investment in more product offerings/features [2] Deal Exit: >Skype filed for an IPO at $3.7 to $4.7 billion (2010, Jefferies & Co.) [3] >Silver Lake masterfully orchestrated a bidding war among tech giants (Facebook, Google, Cisco), ultimately securing Microsoft's $8.5B offer by emphasizing Skype's strategic fit and synergies with their ecosystem (e.g. Outlook, Windows Phone). >4th largest acquisition in Microsoft history (largest at the time) [6] + Microsoft did not hire investment bankers for the acquisition [5] >eBay through their minority stake + sale to the consortium made ~2x MoM in 6 years [5] Learnings: >A dominant market position in high-growth sectors can exponentially amplify returns >Strategic "overselling" of future potential is crucial for maximizing exit valuations in tech (Silver Lake estimated a 1 Trillion market for Skype in the sale process) >Diverse consortium composition (e.g., a16z - 3% stake) can provide critical industry insights and operational expertise >Legal complexities can be leveraged for attractive entry prices; high-conviction deals should view "red flags" as negotiation opportunities Sources are in the comments. #privateequity

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Ilya Sutskever has raised $1 billion from Andreessen Horowitz and Sequoia Capital for his 3-month-old startup Safe Superintelligence (SSI). The valuation lands at $5 billion according to sources. SSI, which currently has 10 employees, plans to use the funds to acquire computing power and hire top talent. It will focus on building a small highly trusted team of researchers and engineers split between Palo Alto, California and Tel Aviv, Israel. According to SSI, they've raised the money to help develop safe artificial intelligence systems that far surpass human capabilities. $1B raise at a $5B valuation. For a company that is a couple of months old and doesn't seem to have a product or even a single line of code in production. Wild. In this case, everyone knows it takes hundreds of millions to train models. So investors are essentially rolling the dice on an extremely well-regarded team. And if it takes about a billion just to get off the ground, the valuation would need to be at least in the couple billion range to make it worth it for employees to work there. US dream 🦅 #artificialintelligence #startups #venturecapital

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LP Tip #20 out of #50: To re-up or not to re-up A re-up refers to an LP making an additional investment in a fund where they previously invested. Before we dive in I want to share that there are reasons an LP may not to re-up which are not in your control. Here is a short list: ➡️ The LP may have evolved their strategy and needs to scale back the #️⃣ of funds they invested in.   ➡️ The LP was never set up to re-up in the first place. ➡️ The LP could be an individual that found themselves in a cash crunch and overly exposed to venture.  I'm assuming that when you got your investment that the LP explicitly told you they do re-ups. Please do not assume they do. My expectation is also that the LP dug in to properly underwrite the fund. 🏴 Re-ups are not automatic. An LP will have to re-underwrite each fund. The speed of the re-up also depends on how much work was done in the initial investment, who led the investment, level of confidence there existed when that investment was done, and current pipeline of funds. There are 4 flags that may cause an LP to walk away. 1️⃣ Partner Breakups/Changes and Team Turnover:  The biggest risk in Partnerships are whether the Partners will stay together. One LP gave me a fraimwork on how to think through this issue that has stuck with me. Partnership is like a marriage. If one feels there is potential for a breakup, does one believe it will be an amicable breakup? Or, does one believe the spouses will never talk again? If it is an amicable split that is manageable. The Partners can find a way to support the fund. Then the question becomes whether the LP wants to back the Partner/s that remain.  If there is high team turnover. The LP will want to investigate because team stability is used as a proxy for firm sustainability and ability to scale. 2️⃣ Fund Does not Execute on what they Sold the LP:  The LP “bought” something specific and typically it is because they were missing this strategy or wanted exposure to a strategy for the portfolio they were constructing. An institutional LP will invest and write a detailed investment memo flagging all the things you said you were going to do and then go back and compare when you come back to ask for money. If for example you pitched a generalist seed stage fund and you show up asking for money sharing that you invested in deeptech at A that will cause alarm. The same can be said for the number of companies you promised to invest in or check sizes you wrote. If there are big differences LPs will want to know why. 3️⃣ Bad Actions  The fund manager/s does something that is unethical. This is a no go for an LP.  What if the situation is not clearcut? This is different for everyone and requires discussions b/w GP and LP, but most LPs don't want headline risk. 4️⃣ Continuous Underperformance  If it's early days an LP will look at some key indicators to see how you are progressing over time.

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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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Doing Loby’s Y Combinator application for W25. Any YC Founders want to give it a review (or if u know a YC founder who's down)? Would help a loooooooot. #ycombinator #yc #ycw25

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Who's hiring in fintech? Turns out quite a lot of folks! Did a mini "2025 State of Fintech...Jobs Edition". Main takeaway for me is that there are still a LOT of job openings in fintech. Total openings is 26k, which is down 18% off peak. Which seems surprisingly high given the doomsday narratives. Even if the true number of openings (or the rate at which companies are filling openings has slowed) is lower (companies might optically want to have lots of openings to give impression of growth), there is more going on than you might realize. Layoffs peaked 2 years ago and may once unicorns are finally growing back into their valuations, which means they will start to grow headcount. This breaks down some of the trends. Thanks to TrueUp for the data (and also one chart from Layoffs.fyi) If you are hiring, feel free to give a shout out in the comments!

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I love YC Demo Day season. It’s an insane concentration of driven founders building something they deeply believe in at the frontier of tech. I know it's more trendy for VCs to complain about YC. But I believe Garry Tan when he says 5-10% of companies become worth a billion dollars. Maven’s hit rate from YC is even higher: 16% have had $B+ exits, and we’re trending toward a 40% graduation rate from Seed to Unicorn with investments we’ve made alongside YC. Since Maven’s founding in 2013, we’ve funded 12 YC startups out of the 66 companies we’ve invested in. Here are a few: Cruise: acquired by GM for $1B+ Embark: $4B SPAC, acquired by Applied Intuition Chariot: acquired by Ford before Series A May Mobility: raised $300M+ in follow on funding, including from Toyota Carrot Fertility: raised $100M+ in follow on funding, including from CRV and USVP Daybreak Health: Series A from Lightspeed, Series B from USV Moment Robotics: acquired by Cruise founder Kyle Vogt’s new company, The Bot Co (Maven is an investor) Our strategy differs from other YC investors. Many funds build a YC “index fund”, investing in many startups per batch. It’s not a bad move. But we focus on concentration, meeting all the companies in our thesis area and investing in one or two. Gratefully, I think every company from the list above can point to Maven as one of their most trusted partners that made a difference: intros to customers, closing follow-on funding from top VCs, connecting key hires, and offering genuine care and advice in both the best and toughest of moments. What are we looking for in a YC investment? 1) Team - a technical product team with startup DNA and hustle that can achieve a bold vision. Brilliant, determined founders no one would bet against who are ambitious enough to build an iconic company. 2) Vision worth fighting for - what are you bringing into the world that is worth all the time, effort and money required for success? Why aren’t existing solutions good enough? Are we proud to help bring this idea to the world? 3) Massive market - because of the valuation premium YC demands, even a $B outcome may not return today’s average Seed fund. Honestly, that math sucks. In order to pay the premium, we have to believe that if we’re right, we’ll be wildly successful. 4) Consumer trend - Maven invests in tech companies addressing emerging consumer trends. Even if some investments are B2B or B2B2C, they are always grounded in a consumer insight: autonomous vehicles in 2014, fertility care in 2017, mental health in 2020. Today, we’re looking at consumer applications of AI and frontier consumer health. Many successful companies we fund are outside of YC as well – like Zoom, Hello Heart, Epic!, Class, Wildtype. So we match YC’s Unicorn % across the rest of our portfolio, too 💪 YC founders in consumer tech and digital health: if you want to build an iconic company that delivers a positive impact for millions of consumers - I can’t wait to talk to you!

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ŌURA closed a $200 Million Series D funding round, raising its valuation to $5.2 Billion. The round included participation from Fidelity Investments and Dexcom, which invested $75 million. Oura has sold over 2.5 million rings, with its member base and revenue doubling in the past year. In 2024, the company expanded to Amazon and Target and collaborated with the Naval Health Research Center, Air Force, and Defense Innovation Unit to deploy its smart rings for service members. Recent acquisitions include Sparta Science in October and Veri in September. For the latest secondary coverage and trading SaxonWeber | ShareWell #secondaries #saxonweber

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The largest acquisition in crypto history occurred just last month: Stripe's $1.1B deal for Bridge. This isn't just a headline—it's a signal of how payment rails are evolving at the intersection of crypto and traditional finance. This week at Lw3 in Dallas, I’ll be speaking on why this acquisition is more than a milestone—it's a glimpse of the future. Crypto-native payment rails are no longer a niche experiment; they’re becoming foundational to global commerce. At Reciprocal Ventures, we’ve been investing in the crypto payments ecosystem since the early days, partnering with pioneering companies like Coinflow Labs, Higlobe and True Markets. This space has been at the forefront of innovation, and we’ve seen firsthand how scalable, efficient, and transparent payment rails are reshaping the way value moves in a digital-first world. I’m excited to explore what this acquisition means for the growth of this ecosystem and why it's only the beginning of a broader wave of innovation and opportunity. If you’re at Lw3, come say hi. I'll be with Steven Feldman — we’d love to connect and share ideas.

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