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Entrepreneur Narratives: How Siamak Taghaddos of Grasshopper Did It

Editor’s Note: This is a new Q&A series from StartUp Beat that features entrepreneurs who have successfully guided their startups (or multiple startups) to maturity. It is a complement to StartUp Beat’s coverage of early-stage startups and an effort to provide further insight into the experiences of tech entrepreneurs.

Bio: Siamak Taghaddos is the co-founder and CEO of Grasshopper, a company which has empowered over 100,000 entrepreneurs to start and grow their businesses with a Virtual Phone System. A lifelong student of marketing, Siamak is one of the youngest CEOs to be named to Inc. Magazine’s 500 fastest growing companies and is the founding supporter of National Entrepreneurs Day. Find Siamak on Twitter - @siamak.

SUB: What was your first entrepreneurial venture?

Taghaddos: I had a few random ones growing up including computer repair “firm” in middle school but my first real venture was PagerWholesale.com. After someone difficulty finding a cheap pager on a high school kid’s budget I found a cheap distributor in California, setup a website, and resold pagers throughout the US to kids and small businesses. A few years later I sold the site to the distributors and founded Grasshopper./p>

SUB: What prompted you to start Grasshopper in the first place?

Taghaddos: Running Pagerwholesale.com in high school wasn’t easy. Customers would call my house, my mom answered the phone with my little sisters screaming in the background. I knew there had to be a better way but couldn’t find a good solution. There were a few companies offering virtual office systems which I used and resold for at first, but the opportunity to create a solid company serving entrepreneurs like myself and the kids I saw running businesses from college was big.

SUB: Was there a point at which you knew Grasshopper would hit it big?

Taghaddos: Even before I started. Something always told me the demand for virtual phone systems would be big.

SUB: Was there a “tipping point” (for lack of a better term) when Grasshopper really picked up steam and where it started growing exponentially?

Taghaddos: We were profitable 2 months after launching and getting signups every day so there was always steam and exponential growth.

SUB: What were the first steps you took to establishing Grasshopper?

Taghaddos: At the same time I wanted to create a Grasshopper-like service, my business partner today was looking to do the same thing. So when we met at college randomly and saw our skills complemented each other, it was a simple hand-shake to get started. He immediately started figuring out the technology while I focused on the business side and getting the startup capital we needed.

SUB: If you had it to do over again, what would the first concrete step to establishing Grasshopper have been?

Taghaddos: I wouldn’t do it any different.

SUB: What were the most significant obstacles to growing Grasshopper to maturity?

Taghaddos: We needed $1.5 million to start Grasshopper and did it with less than $300k, so bootstrapping a telecom with everything involved on the infrastructure side was difficult but an amazing learning opportunity. It also took a few years for us to sharpen our skills running a business.

SUB: What kinds of outside funding did you raise?

Taghaddos: Self-funded with family help.

SUB: What was the metric/milestone that indicated to you that Grasshopper had moved past startup stage?

Taghaddos: When we outgrew our shared office space with our fourth employee and moved into our own office.

SUB: What were the most important lessons you learned about entrepreneurship while building Grasshopper?

Taghaddos: Being resourceful and depending on no one except yourself and your co-founder. Also, a founder with a good eye for design and great designers to implement their vision is a tremendous asset to any company. Just look at Apple.