Aaron ShermanWhether you’re in the board room or a classroom, Aaron Sherman wants to help you tell your story. Aaron’s a tech wizard who’s spent years at Vistaprint, which prints business cards, stationary and invitations on-demand. Now he’s striking out on his own with a new product called Storyboard That. I asked him about the new venture and the joys of entrepreneurship.

Tell me about Storyboard That. What does it do, and who is it aimed for?

Storyboard That is a deceptively simple product to rapidly create storyboards with no artistic skill. I say the product is deceptively simple because it is so easy and fun to use, it is easy to forget how truly powerful it is.

Most people are visual people and communicate best via storytelling. When you can share a storyboard in seconds, the recipient grasps tremendous amounts of context and the implications of what you are sharing. They’re ready to jump into the conversation with you. Trust me, it is glorious.

We actually have two very distinct target audiences. On one side of the spectrum we have teachers who have their students create storyboards. In the time it took to do this interview, a French teacher had her students practice dialogs, a civics teacher had students create public service announcements on recycling, and a second grade teacher in Texas used Storyboard That like a modern day diorama.

The other big audience is for businesses, especially in product development. By using storyboards, companies can rapidly document scenarios of how their customers interact with their product. Seeing how all the pieces go together offers new insights. To make it easier the website offers many “fill in the blank” storyboards to get people started with a strong mental framework.

What attracted you to the idea of Storyboard That?

This is going to sound really corny, but I love to create things and see how people play with my creations. Storyboard That is the ultimate representation of this trait in me. I have created a product that allows other people to be innovative and create their own visions. Of all the creations I have ever been a part of, this is the most powerful and most empowering for other people. It is also off to a promising start as my most successful.

You started working at Vistaprint when it was a small company and helped set up their international offices. Now you’re starting up a business of your own. What is it about start-up companies that’s attractive to you?

I love the small company atmosphere. Storyboard That is actually the fourth company I have started, and I also worked at a startup during high school and most of college. In a small company there is a very personal connection, and everyone feels like they are in it together, and there is an infectious desire to win. What I love most, though, is the conversation Monday afternoon about the latest idea, then having a new version of the product out Wednesday and having results the following Monday. When you see results that fast and know you helped make it happen, that’s just heaven to me.

You’ve been around the world for your job. What’s your favorite place that you’ve visited?

I have been incredibly fortunate with the amount of travel I have done over my lifetime.  I think my favorite place is Southeast Asia. Beyond the amazing food, breathtaking scenery and generous locals are the backpackers. When you are traveling and meet someone is who is taking a year off to see the world and relax it makes you examine your own life and your own aspirations. Do you want to work all day nonstop in an office, or is there a very real tradeoff on leaving early and sitting in a park with the trees?

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Four Questions is a weekly interview column featuring interesting people connected with the Greater Boston Jewish community. Find past columns here. Have an idea of someone we should interview? Email Molly!

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