Five Questions Before Raising Capital

Nathan lists five key questions founders must answer before seeking investment to decide the best path.

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Should you raise money or bootstrap your business? It’s one of the biggest questions every founder faces — and the wrong decision can shape the entire future of your company.

In this episode, I share the lessons I’ve learned from speaking with hundreds of founders about funding, and what I’ve personally applied in building Foundr and my ecommerce brand, Healthish.

You’ll learn when it makes sense to take on capital, when to stay independent, and how to make this decision from a position of strength — not pressure.

Here’s what you’ll take away: • The real trade-offs between funding and bootstrapping (speed vs. control) • Why money amplifies what already exists — and can’t fix bad unit economics • What investors actually look for: traction, margins, and market size • 5 questions to ask before raising: Do I need funding to scale or survive? Is this a $1B opportunity? Do I have product-market fit? • Real founder stories — including Toy Guru’s Shark Tank collapse and BigCommerce’s billion-dollar exit — that show both paths in action • Creative alternatives to equity funding: Kickstarter, grants, partnerships, and strategic capital

If you’re stuck wondering which path to take, this episode will help you make a clear, confident decision based on your goals — not hype.

This is a brand new solo series I’m testing, and I’d love your feedback. Email me directly at nathan@foundr.com — I read every reply. Hope you enjoy it.

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