Essays on business and technology. Never more than a single screenshot. Subscribe here: screenshotessays.com

Joined July 2020
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How SaaS wins in the AI Era
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New investment: @coplane
I'm excited to share that we've raised $14M to build CoPlane, led by @RibbitCapital with @Stripe, @OptumVentures, and @TerrainCap. More on the raise and what we're building: coplane.com/perspectives/ann…
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18 Nov 2025

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It’s Kingmaking Season Again We’re seeing more startups raise back-to-back rounds at increasing valuations, each trying to brute force their claim on an important market. It feels a lot like 2020/2021 when every day, another “king” was crowned in your inbox via Term Sheet or Pro Rata. Search those emails today and you’ll notice how few of the would-be kings became real ones. In AI, it's still early, with a lot of game left to play. Yes, capital is helpful, but you can't shortcut the process by fundraising or being loud. Instead it's best to recognize kingmaking for what it is: a distraction to see through rather than truth.
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It’s earlier than you think
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Today Parallel @p0 launches. At @terraincap we are proud to have backed @paraga and team from the start.
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Artificial Intelligence Underwriting Company (AIUC) launches today. We @terraincap are thrilled to work with @runekvist, @bradr, @rajivdattani and the AIUC team.
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Base Power was @terraincap's very first investment — made shortly after forming the firm. We are thrilled to triple down in their Series B.
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Introducing Free Agency
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Bootscaling and the Reckoning for Seed VC
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We at @terraincap are thrilled to back @amather and the Eternal team.
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New @ScreenshotEssay today: How to Identify Enduring Winners vs. Bridge Solutions in AI
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Beepers, Fax Machines, DVRs and the AI era of Bridge Solutions
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Calling your shot stands in stark contrast to a sea of vague missions from tech giants today. Take one whose mission is “revolutionizing commerce globally.” How will employees know if their mission has succeeded or failed? Perhaps that is the point. In 2008 big banks were thought to be too Too Big to Fail. Today, big tech has become Too Bland to Fail. In contrast, those who call their shot put a stake in the ground. They may succeed. They may fail. But there is no ambiguity about if they delivered on their one shot. This is the opportunity for startups. To move people to action today requires a specific goal with high stakes — championed by founders who point to the possible. Collectively, these founders take our gaze from the glidepath of the present and point it toward the catalysts of the far future. As the world searches for belief, they will find it in these companies.
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AI is a Platform Shift like PC, Web, and Mobile.
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New @ScreenshotEssay today: The Algorithm is You: Bing Chat and Sydney
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Rinsed Raises $12M Series A from Bedrock and Founders Fund
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New @ScreenshotEssay today: Vertical Fintechs are 21st Century Bank Branches
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