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Startup Finance Insights

Practical perspectives on planning, fundraising, forecasting, finance systems, and building a stronger startup finance function.

Get thoughtful startup finance insights for founders and operators, including planning, fundraising, forecasting, and finance systems.

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  • What Investors Want to See in Your Use of Funds

    What Investors Want to See in Your Use of Funds

    Most use-of-funds slides are too vague to help anyone make a decision. They say things like: 45% product, 35% sales and marketing, the remaining 20% operations. That may look tidy, but it does not tell an investor what the round actually buys. For a seed to Series A founder, use…

  • The One-Page Monthly Finance Dashboard I Want Founders to Run

    The One-Page Monthly Finance Dashboard I Want Founders to Run

    If your “dashboard” is a pile of charts, you don’t have a dashboard. You have a spreadsheet museum. A founder dashboard is useful only if it helps you make decisions this month: what you can afford, what is changing, what is constrained, and what you need to do next. Here’s…

  • 10 Finance Documents That Keep Your Fundraise Moving

    10 Finance Documents That Keep Your Fundraise Moving

    If you are seed to Series A and you plan to raise in the next 3–6 months, here is the uncomfortable truth: Most fundraising timelines slip because the founder story is unclear or the follow-ups take too long. You cannot control investor calendars. You can control whether your finance answers…

  • The Better Way to Think About Startup Runway

    The Better Way to Think About Startup Runway

    Most founders know their runway. Fewer know what decision the runway is supposed to support. “We have 14 months of runway” sounds clear, but it can hide the questions that actually matter: What milestone does that cash need to reach? When do we need to start fundraising? Which hires are…

  • The Automation Trap: Clean the Clogged “Pipe” First

    The Automation Trap: Clean the Clogged “Pipe” First

    As a Fractional CFO, I’m often brought into startups at a pivotal moment: the transition from “survival mode” to “scaling mode.” The first thing founders usually ask for is automation. They want real-time dashboards, AI-driven forecasting, and push-button expense management. They want to go faster. The problem? Automation is a…

  • Anthropic just raised $30 Billion. The CEO says they could still go bankrupt.

    Anthropic just raised $30 Billion. The CEO says they could still go bankrupt.

    Raising $30 billion doesn’t eliminate existential risk. In AI, capital buys time, not certainty. While the headlines are obsessed with the $380B valuation, Dario Amodei is focused on a much darker reality. In his recent interview, he didn’t sound like a founder doing a victory lap; he sounded like a…

  • Why January 31st is the Most Underrated Deadline in Your Startup’s Calendar

    Why January 31st is the Most Underrated Deadline in Your Startup’s Calendar

    The champagne corks have long since popped, and the “New Year” buzz has faded into the reality of execution. For most founders, January 31st is just another day of shipping product or chasing leads. But for a Strategic CFO, today is a pivotal “pivot point.” It represents the first hard…

  • Tailwind’s 80% Revenue Crash Reveals Fintech’s Next Big Opportunity

    Tailwind’s 80% Revenue Crash Reveals Fintech’s Next Big Opportunity

    Earlier this month, Tailwind Labs, creators of one of the most widely adopted CSS frameworks in history, announced layoffs affecting 75% of its engineering team. The reason? An 80% year-over-year revenue collapse, despite record usage of Tailwind CSS. A tool that achieved near-ubiquitous product-market fit suddenly found its business model…