Tips for Inspiration and Creativity from the Founder of

by / ⠀Entrepreneur Interviews Startup Advice / May 30, 2022
mountain sunrise

Tell us a little about Grasshopper. Where did it come from and where is it today?

We started in 2003 as GotVMail Communications and re-branded as Grasshopper in May of this year. Our virtual phone system is used by tens of thousands of entrepreneurs to make starting and growing their small businesses easy. It helps them sound more professional and stay connected to callers, wherever they are. Our goal is to become the global brand for entrepreneurs and that takes a lot of creativity. We recently launched our second product, Chargify, to make it easy for web 2.0 entrepreneurs to charge customers and gain business intelligence. And over the next year, we plan to release more tools that empower entrepreneurs to succeed.

How do you find inspiration and creativity for your company?

My best ideas don’t come from a clichéd “ideation session” or a set time of day; they happen when I’m outside the office. So I travel. A lot, if for no other reason than to get the creative juices flowing. There’s a reason why the top floors of a building are the most expensive to occupy, why top executives have the best views of the city, and why city planners and military generals create models to stare down at: When you have a bird’s eye view of the world, it’s a lot easier to put challenges into perspective and strategize your way around obstacles. Having a bird’s eye view of the world lets you see what’s both immediately in front of you as well as what’s on the horizon. Combine that with a plane moving 500 miles an hour and a good book, and you get the perfect storm for new ideas and creativity. For inspiration, I look at companies doing great things, reading stories about successful entrepreneurs, and how everyday challenges create opportunities.

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Why is travel so great? Is sitting in the office all day that bad?

Without experiencing new cultures, different views, new cities, and languages, how can you gain insight and perspective? When you’re stuck on a topic, have writers’ block, or can’t find a solution to a problem, what better way to resolve things than to step out of the office, go for a drive, get on a plane, or travel somewhere, anywhere, for the answers? Sitting at the office is great for execution. But to really get creative, you need to get out of the office.

When we needed a new brand for our first Grasshopper Labs product, Chargify, it came to me while on a flight to Los Angeles. The roots of our re-brand came while sitting on a train from Boston to New York. If I look at any idea I’ve come up with over the past six years, nine times out of ten, it’s been while traveling. Just today for example, while on a flight back to Boston, I thought of our next big campaign for 2010.

This whole concept of “shutting off”  and putting away outside communication is nonsense. I’m not telling you to take a holiday. I’m telling you to work from the air, in another city, on the train, or somewhere you’ve always wanted to go. Expand your mind. Take in new cultures. And read. If you’re in retail or package design, why haven’t you gone to Japan yet for inspiration? In fashion? Surely you’ve been to Paris, Milan and Melrose in Los Angeles. You’d be amazed what removing yourself from every day work does for your company.

How often do you travel? What are some of the coolest spots you have been?

I travel about two dozen times a year, mostly between Boston, NYC, and Los Angeles, and once or twice a year to Europe and the Middle East. Every year I also try to visit a new city. Last year St. Barth’s was a great place to relax and read and this year I got a lot of design inspiration from Stockholm. Next year I’ll be checking out Buenos Aires.

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How do you spread this creativity and innovation atmosphere around your company? Do you do anything specific to encourage employees to think outside the box?

I try to lead by example through new campaigns, bringing in really smart people to work with, and getting everyone else involved and contributing ideas. I don’t force creativity as everyone is different and ideas can come up any time, but I do ask a lot of questions and encourage people to read good books. Our re-branding campaign and Entrepreneurs Can Change the World movement was a collaboration of a lot of people at the company and it set the bar high for future campaigns. And every quarter more than half the company reads a new book for inspiration and ideas are posted to our internal wiki. In addition, always being entrepreneurial is in our DNA. Not only is it one of our core values, it’s also reflected in our work environment. The office is a fun place to work at, very flexible, and even has a picnic area with Astroturf and a Wii room to inspire creativity. 

A lot of young entrepreneurs have tight budgets. Travel may not be an option. What do you suggest?

Get out of the office. Go to a café. Take a drive. Go to the park. Work from a local hotel lobby for the day. Plus, travel doesn’t have to be centered on remote locations, and doesn’t even have to be expensive. Visit a local city you’ve never been to. Find out how they’re different there, or how they’re the same. The key to these kinds of activities is being the silent observer. And even if you can only travel somewhere once a year, it’s well worth the expense. After all, you’re the CEO. You need to be creative, so consider it the cost of doing business.

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What are some tools that will help entrepreneurs take their business on the road?

First, my virtual phone system from Grasshopper (of course). My extension forwards calls to my cell phone anywhere in the world, and our Voice to Text feature converts my voicemails to text so I can read them from my BlackBerry. A Kindle from Amazon to put all your books on is great. A good laptop with an aircard for internet access. Web Outlook from RackSpace for email. Trillian for IM. Basecamp from 37 Signals for collaboration. And I just recently started using Twitter last week (follow me @staghaddos).

What are some books entrepreneurs should read to spark that innovation?

Some books I love are Buzzmarketing by Mark Hughes, Eating the Big Fish by Adam Morgan, ViralLoop by Adam Penenberg, Buyology by Martin Lindstrom, and Word of Mouth Marketing by Andy Sernovitz. And for a quick read, Who Moved My Cheese by Spencer Johnson does a great job and putting change into perspective.

Make sure to have something to take notes with. Ideas come and go quickly, so write them down. I email myself notes on my BlackBerry. For every book I read, about two dozen emails fill up my inbox with ideas.

Interview with Siamak Taghaddos co-founder of – virtual phone system, toll free numbers and voicemail.

About The Author

Matt Wilson

Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.


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