When Pitching, Be Like Gandalf

Pitching investors can feel like an epic journey—full of challenges, uncertainty, and the need to inspire belief in something bigger than yourself. So why not take a page from one of the greatest mentors of all time?

As we enter a heavy season of pitching, here are some lessons I’ve learned—through both experience and a little wisdom from The Lord of the Rings.

1. Be Confident in Your Plan

"A wizard is never late. Nor is he early. He arrives precisely when he means to."

Investors don’t always know the right answer, but they do want to believe that you do. Confidence isn’t about arrogance, it’s about conviction. When Gandalf reassures Frodo that wizards are never late, he’s not just making an excuse. He’s projecting certainty, even in the face of doubt.

When pitching, you must approach every question with that same level of confidence. Investors are skeptics by nature, and they can sense hesitation. If your plan feels weak, under-researched, or uncertain, they will pick it apart. But remember: you are likely more of an expert in your target market than they are. Own that expertise.

2. Give an Air of Inevitability

"Things are in motion that cannot be undone."

Investors want to invest in unstoppable founders. They know that backing a startup means committing for years. They need to believe that, whether they invest or not, this company is going to succeed—and they’d be foolish to miss out.

A great pitch doesn’t just highlight potential; it makes investors feel like they are witnessing momentum. They should walk away thinking:
"This is happening. The only question is whether I get on board now or regret it later."

Be unstoppable.

3. Listen and Be Coachable

"Faramir, tell me everything."

While investors may not be experts in your exact business, they see everything. They spot patterns across multiple industries, companies, and market cycles. Many of them got into investing because they love working with founders and want to help.

But here’s the key: being coachable does not mean being a pushover.

Great founders listen actively and ask smart questions. They extract value from investors’ insights but don’t blindly follow every piece of advice. The best investors want you to challenge ideas, push back when needed, and show your own reasoning.

4. Investors Invest in Lines, Not Dots

"I am Gandalf the White."

Your pitch is not a single, isolated moment—it’s part of an evolving narrative. Investors rarely write checks after just one meeting. Instead, they track founders over weeks, months, or even years, looking for signs of progress.

Just as Gandalf transforms over time, your company’s story should evolve with each investor touchpoint.

Final Thoughts

A pitch isn’t just a transaction; it’s the beginning of a long-term relationship. Investors invest in people and stories, not just slides and metrics.

Too many founders get distracted by making the “perfect” deck when what truly matters is building belief in yourself, your vision, and your team.

So next time you pitch, channel your inner Gandalf.