One of the skills I am most grateful for the opportunity to hone during Y Combinator was the ability to pitch an idea or present a demo very quickly to a wide range of people. Our experience forced us to elevator pitch Wufoo constantly to other hackers, entrepreneurs, investors, students, potential employees, marketers, lawyers and a good number of eccentric nay-sayers. During our weekly dinners, we were constantly introducing and reintroducing and practicing and rehearsing and playing with wordings, phrases and approaches to make our application interesting, compelling and in the end exciting enough to stick around and hear more about. With 10 other companies with fantastic ideas and applications of their own in the room, it was a Darwinian environment that made everyone’s pitching skills evolve quickly.

Yes, it helped that Paul Graham was essentially our coach (he’s brutally honest once he gets to know you and if you’ve ever heard him talk about an idea, you’ll learn something about generating genuine excitement in others), but it was practice that helped the most in the end. The following are links to some of the best advice I’ve come across to dealing with pitches and demos. Essentially, it’s the stuff to practice over and over again.

The Best Stuff First

If you’re a book person then I highly recommend you read Made to Stick : Why do some ideas thrive while others die? by the brothers, Chip and Dan Heath. If you like books by Malcolm Gladwell and Seth Godin, you’ll love this book. It’s one of the few marketing books I’ve ever enjoyed reading and the advice and case studies they present are surprising, fun and just plain practical.

If you’re only going to check out two links from this list, however, about pitching your ideas, then please read How to Pitch an Idea by Scott Berkun and How to Present to Investors by Paul Graham. Berkun and Graham aren’t newbies when it comes to getting people to hear them out and follow through. Best part: their writing is clear, insightful and also practical on the topic. Can’t ask for too much more.

Advice from Magazines

That is unless you want to hear what a corporate presentation coach has to say on the topic. Gallo wrote a short piece in Business Week titled Mastering the 30-Second Pitch. It’s simple stuff, but good for review. For more check out his book and his online site at

I also enjoyed the 3 part series, Perfecting Your Pitch by Bill Joos in FastCompany. Bill is the vice president of business development for and therefore has plenty of street cred in regards to hearing people explain day in and day out about the next exciting thing. Here they are in quick reference formation: Part One: Assume Short Buildings, Part Two: The Horse Race, and Part Three: The Overview Overview

Learn from Hack Day

Hack Day is a Yahoo! organized event where attendees were encouraged to create web applications that utilized one or more of Yahoo’s APIs and open source libraries. In the end, the Hack Day concluded with a hack demo session, which forced people to present their implementations in 90 seconds or less. A perfect constraint for optimal seduction. Attending this event is obviously preferred, but reading about the experience second-hand isn’t too bad either. Here’s some blog posts that were pretty solid presenting lessons learned from the event:

Listen to Great Storytellers

In the end, a great pitch is really about great storytelling and if you can’t tell a joke or even a simple story about something interesting that happened in your life, good luck getting a date never-mind an investor. Best thing to do, is to learn from the masters. My favorite storytellers are on the radio and my favorite stories come from This American Life, which is a weekly radio program containing touching and compelling anecdotes focused around a theme. Hosted by Ira Glass, it’s an amazing experience every week and I’m glad to see that they’ve successfully translated it to television as well. Here’s some storytelling advice from Ira via Youtube: Part 1, Part 2, Part 3, and Part 4.

In addition to listening to This American Life, you should also watch the great presentations that take place at conferences like TED, GEL and Poptech. There’s some great alternatives to your standard PowerPoint bullets in those videos.

HTML Form Builder
Kevin Hale

Pitching Ideas Roundup by Kevin Hale

This entry was posted 3 years ago and was filed under Notebooks.
Comments are currently closed.

· 1 Comment! ·

  1. Nivi · 3 years ago

    I use David Cowan’s approach for every single investor pitch:

    This is the best way to pitch investors by far.