When a smaller fund loses an investor to a bigger, more established one, it’s easy to assume it’s just about brand or scale. Often, the real moment it’s decided is quieter: an investor asks to see exactly how decisions get made, and a strong story doesn’t carry the same weight as something you can actually show. This isn’t about bigger …
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When a fund launches, it usually decides upfront how much of its total money to set aside – or “reserve” – for investing more in its strongest companies down the line. That number is a genuine, informed guess made before there’s any real evidence to go on. The tricky part isn’t deciding it – it’s finding time, later, to check …
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Almost every fund eventually has a company raise money again at a lower valuation than before – a “down round” – or fail to raise at all. That’s just how startup investing works, not a sign anyone did anything wrong. What actually helps in that moment is being able to look back at your own reasoning clearly. And keeping that …
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The Follow-On Decision Nobody Wants to Own When a company you’ve already invested in comes back asking for more money – a “follow-on” – that decision usually has to happen fast, often in the middle of everything else you’re juggling. It’s not that funds don’t want to plan ahead here. It’s that planning ahead means knowing exactly how every company …
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The Power Law Lie GPs Tell Themselves Venture returns genuinely follow a power law – a small share of deals drive most of the gains. But funds routinely misuse that fact to excuse loose screening, on the logic that “one winner covers everything, so early diligence doesn’t need to be rigorous.” The data on who actually wins under the power …
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Why Your Best LP Update Is Boring The LP updates that build the most trust over time aren’t the ones with the most exciting news – they’re the ones with the most predictable structure. Same format, same cadence, no surprises buried in paragraph four. That consistency is a proxy LPs read for something bigger: whether the fund behind the update …
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Why “We’re Building an AI-Native Fund” Is Becoming Part of the Fundraising Pitch “AI-native” used to be an internal ops decision – which tools the team happened to use. It’s increasingly showing up inside the fundraising pitch itself, because LPs are starting to read a fund’s AI infrastructure as a proxy for speed, consistency, and reporting quality. The risk is …
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Why Emerging Managers Are Winning LP Trust With Better Systems, Not Just Better Numbers Institutional LPs are concentrating capital with established firms and putting first-time managers through operational due diligence that goes far beyond thesis and track record – data rooms, decision logs, reporting cadence. The emerging managers actually closing capital right now aren’t out-pitching the big funds; they’re out-organizing …
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The Anti-Portfolio Problem: What Your Fund’s Passes Say About Its Judgment Every fund has an anti-portfolio – the deals it passed on that later became huge wins for someone else. Bessemer famously publishes theirs. Most funds never study their own, because reviewing a pass takes deliberate effort and reviewing a win doesn’t. That’s backwards: passes are the highest-signal dataset a …
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The Deal Champion’s Blind Spot: Why the Person Who Loves a Deal Can’t Be the One Who Clears It The partner who sourced a deal and wrote the memo has already invested identity and reputation in it before the IC meeting starts – which makes them structurally unable to grade it neutrally, no matter how disciplined they are. Formally assigning …
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