Answering Steve Blank’s burning questions

This week the legendary Steve Blank and I had another one of our fireside chats. I’ve had the privilege of doing these every few years, and without fail, every time I learn something. Steve’s a prolific writer with at least four books, hundreds—if not thousands—of blogs, articles, and posts, and is considered by many of us as the father of modern entrepreneurship. But one nugget from Monday’s chat is particularly profound for entrepreneurs pitching to investors and anybody communicating for a specific purpose.

Steve Blank & JD Schramm

We covered lots of ground in our hourlong chat, but when I asked him what advice he has for entrepreneurs when pitching, he essentially said:

Forget about the long pitch decks and templates.

When he hears a pitch, he said he looks for the answers to just three questions:

• Tell me what you thought on day one and found out you were wrong.

• Tell me what you’ve learned from that experience.

• Tell me why you think this idea can scale.

The simplicity of these three statements gets to the very heart of successful entrepreneurship and, I think, successful communication. It shows vulnerability—we got something wrong. It shows curiosity—we learned from our mistakes. And it shows ambition—why we can scale.

Those of us who see pitches on a regular basis are all too familiar with the confident swagger of “let me tell you why we’re great.” It’s refreshing to consider, as Steve Blank does, the power of simply being authentic about what you got wrong, what you learned, and how those insights will lead to your success.

This conversation reminded me of former American Express CEO Harvey Golub’s opening at NYU Stern each time he came to speak. He’d ask the class “Do you want me to tell you about one of my greatest successes or one of my greatest failures?” You can guess the outcome. Never once did students request that he share a success. They consistently wanted to know about his failures, and he shared them along with what he learned from them.

Whether or not you are an entrepreneur, consider where in your communication you can share what you got wrong and what you learned. And for the entrepreneurs still with me, also be ready to share how these lessons will help you scale.

JD’s Recommendations: what I’m reading, hearing, and seeing:

• Reading: Marc Champagne’s Personal Socrates is a treat and offers questions to ponder (or better yet answer in your journal) to upgrade your life. (Thanks Bronwyn!)

• Hearing: Admittedly Sam Paar & Shaan Puri are a bit of “tech bros,” but I’ve begun to treasure listening to My First Million. Episode 436 is Shaan’s masterclass on pitching.

• Seeing: My friend Sara Lomelin’s TED Talk, Your Invitation to Disrupt Philanthropy, provides a compelling alternative view to charitable giving.

Thanks for enjoying my newsletter. If you have ideas for topics, drop me an email.

As always, jds

P.S: At this writing, space remains in all three of the Realize the Result one-day workshops that my husband Ken and I created. Consider joining us for an incredible day to help you achieve mastery in your next presentation. We’re offering this on April 26 in KC, May 24 in NYC, and June 8 in SF. (We chose cities you will know by their acronyms!)