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Startup Pitches and Nesting Dolls

Great entrepreneurs are great storytellers. And they always have a concise story that fits the current circumstance, ready at a moment’s notice.

Bret Waters
3 min readJun 1, 2023


In the fundraising world, pitching tends to be a series of meetings in increasing length. First the proverbial elevator encounter, where you only have time for a sentence or two that will get you the first formal meeting. Then that first meeting might be a few minutes over Zoom. Then maybe an invite to actually come into the office for a half-hour in-person meeting. Then, hopefully, an invite for an hour-long meeting with the other partners.

In each case, your desired outcome is exactly the same: to leave them intrigued enough that they want to have another meeting.

It occurred to me the other day that this is a little like those Russian nesting dolls. You need a one-sentence pitch that opens up to a one-minute pitch that opens up to a 3-minute pitch that opens up to a 10-minute pitch, etc.

In my current Stanford course we’re working on a fictional venture. The one-sentence pitch is:

For busy people who want to eat healthy, we are developing a subscription-based service that delivers fresh, healthy breakfasts directly to your home or office.

Then the one-minute pitch is:

I’d like to tell you about a very cool new healthy startup opportunity. We all know that the medical research says we should all eat a healthy breakfast every day. We know that. Our moms told us that. But the reality is that we’re busy and it’s hard to find the time to prepare a healthy breakfast every morning. But let me ask you a question: You pay for a gym membership in order to be healthy, so why wouldn’t we pay for a breakfast membership That’s why we’re launching a new subscription based service that delivers fresh, healthy breakfasts directly to your home or office. The best part of our startup idea is that the economics are really solid — the fact that it’s subscription-based means that we know the exact production numbers in advance every week, which makes our meal prep and delivery much more efficient than on-demand services. And, of course, subscription revenue is the best kind of revenue. I’d love to have a meeting and tell you more.

If you want to see the 3–minute, with slides, it’s here. You get the idea.

The point is this: Every great entrepreneur has the ability to tell a crisp, clear, and compelling story about what she’s working on, and why it matters. And every great entrepreneur is nimble enough to tell that story within the confines of the time available, with the desired outcome always being to leave the audience wanting to hear more (ie, get another meeting).

So in your head you need to have a set of pitches that fit inside each other.

Sort of like those Russian nesting dolls.

This article was merged into my new book, The Launch Path, now available on Amazon.



Bret Waters

Silicon Valley guy. Teaches at Stanford. Eats fish tacos.