Zach Kamran

A common mistake early-stage VCs make is confusing good decisions with good outcomes. Good outcomes don’t always mean good decisions—luck often masks flawed reasoning. Focus on process over outcome bias. Invest in strong decision-making frameworks, not just duplicating “wins.”

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Every VC claims they have an edge, but from where I sit as an LP, it’s clear: the next generation of fund managers will need stronger arguments than 'working very hard' or 'being helpful for founders' to raise money. The best fund managers will set themselves apart with these three non-obvious skills: 1. Cultural fluency - Some of the best startups come from immigrant founders, but they’re navigating a system that isn’t always built for them. VCs who know how to build trust, understand their challenges, and support them where it matters will unlock incredible opportunities. 2. Downstream sales: There’s more money than ever chasing top founders, and the best deals are going to the VCs who founders actively want to work with. It’s not just about pitching; it’s about being the one they call first because they know you’ll add real value. 3. Value-add 2.0: Founders don’t need more generic advice. The best VCs create real pull by building opportunities—whether that’s connecting the right dots in their portfolio or unlocking new markets—that founders actually want and can’t find anywhere else. This is what LPs should focus on when backing funds—it’s what separates good from great. ---- Interested in investing in VCs & startups? let's connect.

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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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The VC funding model when everything works out fine... In real life: Only a few startups make it! So if you are considering going the VC route: Have a backup plan!

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Nice overview of how we're using data to inform how we invest in early-stage founders. We'll be announcing more this summer but we're seeing some really interesting early data. https://lnkd.in/exU_Juf5

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VC platform teams rarely add meaningful value to portfolio companies. They’re mostly a tool for GPs to justify raising larger funds and collecting higher management fees.

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Startup decks vs Business plans. It's accepted that a startup needs a deck. Dax Dasilva of Lightspeed Commerce made an important point on 20VC. Writing a business plan - including financial projections - is an important step. It requires discipline. It provides a rigorous framework for thinking deeply about the problem you're trying to solve. Harry Stebbings countered that he doesn't even want to see a deck since it's all dreams. We spent a lot of time and energy on our business plan with the expectation that we would show it to no one ever. The business plan was part of our roadmap for the company. We researched customers - including having 50+ conversations. We wanted to understand them: their background, their interests, their presence on social media. We also wanted to understand how they were evaluated by leadership and how integrated they were with the business of the company they were protecting. We researched pricing both with potential customers and other products in our industry to find out if OpEx or CapEx was a better fit. How did they buy today? How would they like to buy? We did market research to understand the verticals and map the right entry point - we were wrong but that doesn't reduce the value of the research. We looked at competitors in depth to understand what they were seeing that we weren't. Dax is right. This is an invaluable document that should be updated every year - the company is changing, the market is changing, there's more feedback about price and ICP. It's not for sharing with the outside world. It's a map for driving forward. Decks won't get you investment - VCs invest in people. We make decks but we know they don't tell our story. The deck is a calling card. Dax and Harry are both right. https://lnkd.in/e25M82xY

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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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I met the ex-Squarespace CEO. His new startup raised $227M. He ditched SaaS when every VC said not to. He trusted his gut—then grew to $150M in 2 years: Dane Atkinson was the CEO of Squarespace from 2007-2011. He grew it from $2M-$15M in revenue. In 2019, he founded Odeko & raised $6M from tier 1s like First Round Capital. The idea was to build B2B SaaS to help coffee shop owners predict future sales. But the owners didn’t care— they had bigger problems. Suppliers changed prices without warning. Deliveries didn’t come on time. Sometimes, deliveries didn’t come at all. Dane knew he needed to do more than sell software. He needed to take over the entire logistics back end & give independent coffee shops the same logistical support that Starbucks has. So he told his VCs— and they hated it. B2B SaaS is the holy grail— recurring, predictable, high margin. The new model would be capital-intensive, with lower margins, lower multiples. It was a huge mistake. It was also exactly what customers needed. So like a good founder, he rented a truck— and did it anyway. He took over his customers’ entire supply chain. High-risk high-reward. And his customers loved it. And then, just as things were starting to work, COVID came. Every coffee shop shut down. Revenue immediately dropped to $0. Dane was forced to cut his team from 40 to 15. “We didn’t know if the industry was going to be around.” Fortunately, a few months later, coffee shops started opening back up. The disruption in the status quo turned out to be a tailwind. COVID was a reset. And coffee shops were willing to try something new. So Odeko went from 50 customers at the start of 2020 to 600 by the end of that year. By the end of 2022, they had over 10,000 customers. From $0 to $150M in revenue in 2 years. “When something really works, it just works. It was the same thing at Squarespace. We all could have just gone to a beach, and that thing would have just kept on growing, and kept on printing out money.” Here are the 3 key things that Dane got especially right: 1/ To this day, Dane has a rule that he has to have coffee at a coffee shop every day. He has to talk to a customer every day. Staying close to customers means he’s never led astray. It means he’s always on top of what customers need. 2/ He keeps feedback loops tight. By staying close to customers he notices issues faster. He implements solutions faster. He doesn’t get bogged down in red tape. 3/ He trusted his gut. Founders are founders for a reason. Advice is useful, but you can't let anyone decide for you. Like Dane said, as a founder, “All you have is your instinct”. /// Listen to the full episode with Dane on The Product Market Fit Show. #startups #venturecapital #founders

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Please go through our GP, Gautam Kapur’s thoughts on founder’s deep understanding of the problem v/s potential market opportunity! Chanakya | Puneet Malik | Gautam Kapur

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A couple of years ago, I published a post On YC batch quality at scale that showed the upward trend in Y Combinator startup outcomes despite a massive increase in YC batch sizes over time. While it’s counter-intuitive to many investors, YC has managed to only maintain but improve the quality of startups it admits into the program even as batch sizes have increased from a dozen or so companies in the early years to 200+ today. My previous post measured YC batch quality simply by the percentage of startups from each batch that made it onto YC’s Top Companies list ($150M+ valuations) or became unicorns ($1B+ valuations). While these are great measures of YC startup success, they are retrospective in nature, since it takes several years for YC startup valuations to mature. Since Rebel Fund maintains the most comprehensive database that exists of YC startups, founders, and outcomes outside of YC itself, we’re in an excellent position to not only look at retrospective measures of YC startup quality like valuation growth, but also prospective measures like overall company and founder quality…

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Allocate just released an analysis on a dataset of 253 venture funds, with only pre-2019 vintage years being included. The analysis shows a clear negative correlation between high risk / high reward investment profiles and size of venture fund, i.e. the smaller the funds, the higher the performance, but also the higher the risk. Two ways that LPs can mitigate the higher risk of smaller funds: 1. Diversify across more emerging managers, and 2. Invest across vintages with said managers. Here are the details: Small Funds (0-100MM): Mean TVPI: 4.3 Standard Deviation: 2.4 Median Portfolio Companies: 26 Mid-Sized Funds (100-250MM): Mean TVPI: 3.6 Standard Deviation: 2.0 Median Portfolio Companies: 24 Mid-Large (250-500MM): MeanTVPI: 3.0 Standard Deviation: 1.2 Median Portfolio Companies: 35 Large (500MM+): Mean TVPI: 2.7 Standard Deviation: 0.9 Median Portfolio Companies: 43

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Closing out on YC W24 batch with the ever-present question: Are YC Valuations Too High? 🔥The same burning question resurfaces whenever Y Combinator unveils its latest batch. At Acacia, we dive into this semi-annual debate with a nuanced perspective. 🎓Start with the fundamentals of SAFE agreements, which cap the price of equity in future priced rounds. Valuations are not being set, but expectations sure are. 👩‍🍼Next acknowledge that many YC companies are in their nascent stages, often pre-revenue and reliant on their first external capital, usually from YC itself. 🤝Not only are valuations not being set, but YC isn't setting them. Founders set caps and target raise amounts considering market trends, YC terms, feedback from angels and VCs, and more. With a low acceptance rate and strong historical track record, YC founders ask for more (right or wrong.) 👉The process is intricate and merits a careful approach from investors like Acacia, who invest in companies, not an entire batch. 🎰 Often, we encounter YC startups asking for valuations that seem to include every possible future success. Our Investment Committee carefully considers whether the price reflects real-world potential or an over-optimistic scenario. Companies that rank strongly on revenue but are fully priced at 40x or higher multiples risk being priced to perfection. The biggest risk here is being set up for down rounds, as companies can miss growth targets for many reasons (recently, macroeconomic factors like interest rate spikes.) 🎯As we navigate the complexities of startup valuations, particularly those emerging from YC, our goal at Acacia isn’t just to invest. It’s to partner with companies whose potential to grow and succeed aligns realistically with our assessment and market trends. 🎤What’s your take on YC valuations? Have you experienced similar questions or challenges in your investment decisions? Share your thoughts below.

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Fundraising Realities The Bar Is High, and Here's Why Even in a year when my fund was closing 20+ deals, I personally only invested in 1-2 startups annually. Smaller VC teams?  They might only do 3-5 deals per year or skip investing altogether for months. This is why fundraising is so challenging.  You’re not just competing with other startups.  You’re competing to be the best founder an investor has seen in the past 6+ months. There’s no room for winging it.  You have to consistently prove you’re the top choice  - Across multiple months.  - Across multiple pitches.  - Across multiple rounds. 🔑 So, how do you become the one investors say yes to?  It’s not luck it’s systems. Here’s how to build one:  1️⃣ Get Introduced by Trusted Connections  The best way to stand out is to be vouched for by someone the investor already respects. Relationships matter. 2️⃣ Craft a Narrative That Makes You Unforgettable  Investors hear dozens of pitches every week. What makes you different? Highlight your expertise, vision, and traction with clarity and confidence. 3️⃣ Run a Process That Shows You’re Exceptional  Investors aren’t just assessing your startup they’re assessing you. A disciplined, transparent, and well-organized fundraising process sets you apart. 🚀 Fundraising isn’t just about asking for capital’s about showing why you’re a founder worth betting on. Great outcomes are built on great systems that make yours count.

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Dan Primack had some pointed criticism for #VC yesterday in his Axios Pro Rata newsletter (a daily must read IMO 😤). In short, the model doesn't work if it can't produce exits for LPs. Don't blame public markets (which are at all-time highs) for the lack of liquidity either. 📈 💸 Instead, this is a "liquidity drought of your making" where "...swinging for the fences on every pitch, rather than taking the single or double that's available" is the only way out when you invest at "sky high valuations." 😰 "A whopping 37% of "unicorns" are being held for at least nine years by VC funds, including 13% that are past the 12-year mark." 😳 ⌛ Is he right? Is VC at a dire inflection point? Or is Primack prematurely hitting the panic button? 🚨 https://lnkd.in/dts92pXr

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Why do 99% of YC founders fail post-demo day? Ever notice how startups in Y Combinator operate? They work backward over 3 months, go full throttle, and by the end, many land major funding.  But what happens after the big launch? This initial momentum tends to wear off, and most companies get trapped in a slump, almost like quicksand - slowly and steadily but not realizing you're unable to get out. At Oliv, we fell into the same trap—a massive build-up, then a dip in energy, followed by another scramble to get things going again. It wasn’t sustainable. That’s when we decided to convert YC training into a process. We decided to do a launch every 8 weeks. Why 8 weeks? And why not the standard 3 to 6 months? For a start-up at our stage, we need to ideate fast and execute even faster. This sweet spot gives us just the right amount of time to plan, ideate, and execute—all with a laser focus on our next big goal. No more long lulls or lost momentum. Here’s our approach: - OKRs: After each launch, the team sets clear OKRs for the next launch. It’s all about aligning with the big picture while keeping it actionable. - Tailored sprints: Marketing thrives on weekly sprints for agility, while engineering goes bi-weekly to dive deep into complex tasks. And this is why it works,  - Complete visibility: We see everything in motion at a glance—team objectives, progress, and any bottlenecks. Decisions get made faster, and issues get resolved quicker. - Velocity, not speed: While we want to execute faster, launches help us tweak and realign in the direction the market needs us. - Accountability becomes habit: With structured sprints, everyone stays aligned, transparent, and accountable. No one’s coasting—ownership is built into the process. Switching to 8-week sprints wasn’t easy, but it’s been a game-changer for us at Oliv.  We’re no longer just launching products—we’re consistently delivering results, staying energized, and reaching the potential we knew was there.

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