A Case Study: How The Best Entrepreneurs Manage Risk

Lewis Schiff interviews Jere Simpson, Kitewire and Netpure - Business Brilliant podcast

I interviewed Jere Simpson, the founder & CEO of Kitewire, a software design company that counts the FBI, Homeland Security, The Pentagon, Bank of America, Samsung and Amazon among its clients. Like a lot of entrepreneurs, Jere’s always busy juggling multiple projects. I caught up with him upon the launch of netpure, a new venture that represents the next step in his entrepreneurial journey. I quickly realized that there’s a lot to learn from Jere.

Jere’s success story is like a lot of other entrepreneurs. He started a B2B services company because it allowed him to start small, first with himself as the head programmer, adding on more staff as he found more work. No factories or expensive equipment required. He was selling time for money.

Kitewire grew quickly, but would not scale beyond a certain size. Jere knew that his employees had a value many times higher than their salary, but he couldn’t really give them the compensation that he wanted to in a time and materials market. In order to take his business to its next level of success,, he needed to make a shift in his business approach.

The next step in Kitewire’s evolution was a savvy one. “We started listening in to our customers’ needs. What did they need that people aren’t making, and that we had the experience to make? We thought that the products business would be a way better business to be in than selling labor,” Jere says. Kitewire began experimenting with the B2B market. They came up with a mobile security and mobile device management product, and started shopping the idea around to a selection of potential clients. “We thought that if we could just knock down one really big client, we could pay for the whole workforce, and anything we made past that would be extra profit” Jere told me. They began working on this product while simultaneously pitching potential clients. They found a client who showed interest and agreed to partially cover the expenses for the remainder of the development. In this way, Kitewiremoved up a level in terms of risk management – they began to build capacity first, while also confirming the existence of a market for their product.


After finding some success in the B2B market, Jere took Kitewire to the next level of risk management with netpure – a “build-it-and-they-will-come” model for the consumer market. With the Kitewire’s netpure child-safe internet solution, Jere is hoping to reach a far bigger market – a customer base numbering in the hundreds of thousands or more. The journey of Kitewire is a great example of the way that business owners evolve over time in the ways that they manage risk. Jere is learning how to manage risk better and better as he matures as a business manager and gains the experience needed to know when his company is ready to take the next step – and in which direction.

Risk is part of entrepreneurship. And the best entrepreneurs are the best risk managers. The trick is to look for or create opportunities with a comfortable balance between risk and reward. You may not bet your whole company on an untested product or service for a market that may not even exist, but you also shouldn’t cling too tightly to a model that is holding you back from any growth or innovation. What’s the next big leap in your entrepreneurial journey?

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