Everyone loves a good story. (Source.)

Pitching your business is the easy part.

In 7 years of venture capital, I’ve come to appreciate a few hard lessons about pitching. One of those is that, for all but a few masterful storytellers, pitching yourself is harder than pitching your business.

Businesses can be placed into neat, little categories like business model, market size, and barriers to entry. Most MBA’s learn these basic components of a pitch in their first year. Harvard Business School even has an event called the Business Speaking Competition (a.k.a. the B.S. Competition), wherein a student must deliver a business pitch for a fictitious product, without seeing the slides beforehand. The pitches are often more convincing than you’d think (*see footnote below*) because the components of a standard business plan are so similar.

Unlike business plans, humans are remarkably different than one and other. I see significant variability in how people talk about themselves, and the majority do a mediocre job getting their story across. It’s easy to assume that you’ll be great at telling your own story since, by definition, you’re more intimately familiar with it than anything else; but, it’s not your story you need to worry about — it’s how your telling of it communicates your enthusiasm, qualifications, authenticity, and motivations.

If you want these points to resonate more clearly, I’d suggest a few best practices that I’ve extracted from the best personal story tellers I know:

  1. Assume the recipient of the pitch knows nothing about you. By starting from scratch, you level the playing field and are assured that no important part of your story will go unheard. Do this even for people that were introduced to you by a close mutual friend.
  2. Tell your story in chronological order. The human brain is wired for storytelling. In fact, a good story, with narrative tension and resolution, has been shown to boost oxytocin levels in the brain of the recipient. Good storytellers, quite literally, give their audience a contact high. Don’t short circuit this natural advantage by jumping around too much out of order, even if you are interrupted.
  3. Use company names and titles. If you say you “worked at a startup,” the first thing the recipient will think is, “Which one?” Now she’s no longer listening to you. Ditto for title. If you don’t say what you did at that company, now she's wondering about your role. Even if a particular job wasn’t impactful, or particularly prestigious, you’re always better putting the facts on the table when you walk through your story.
  4. Focus on outcomes. For each job you mention, it’s best to hit upon at least one measurable outcome — sales numbers, product growth, hiring numbers, etc. Quote results that are meaningful and stick in the recipient’s brain. If the recipient needs to talk to a colleague about you, she’s probably going to find it easiest to cite this hard data.
  5. Explain your motivations for making decisions. So, you decided to leave an engineering role and become a product manager in your next job. Why? Your motivations are probably indicative of future behavior. Make sure you contextualize these decisions for the recipient, or she will fill in the blanks herself…perhaps incorrectly.
  6. Keep in mind the “So, what?”. Anything you emphasize needs a reason behind it, in the context of the pitch. If you spend a few minutes discussing a past decision or a role, you need a purpose for doing so, e.g. “I want this person to know I’m deeply technical,” or “I want this person to understand that I’m really swinging for the fence on this new company.” Be intentional with those purposes.

If you rehearse your own story with the same rigor as your business pitch, and you abide by these guidelines while doing so, your story will ring truer and stick in the brain of the person hearing it.


* Shout out to my friend John Coleman, who won the B.S. Competition in 2009 by pitching “Robot Vending Machines.” When you watch this video, remember that he is seeing each slide for the first time as it advances:


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