When serial entrepreneur Jamie Siminoff came to talk with students at Providence’s Met School recently, he emphasized two characteristics that every successful entrepreneur must have – passion and focus.
“Once you get into something, it’s got to be your life – it’s got to be your passion,” he told them. “You need a crazy passion.” He added: “It can’t be about money, because you’ll never stay in the business.”
Siminoff knows what he’s talking about. The 31-year-old is CEO of PhoneTag, a New York-based company that has pioneered the use of speech recognition technology to convert voicemail messages to text. The company has been adding subscribers at a rapid rate, and last year PhoneTag’s success led Crain’s New York Business to name Siminoff one of the city’s top entrepreneurs.
But PhoneTag is not the first company Siminoff has started – in fact, it’s his fourth. “Everyone thinks of lots of ideas for businesses,” he said, but most people don’t actually start them.
While an undergraduate at Babson College in Wellesley, Mass., Siminoff started an electronics-distribution firm. He later founded a consultancy, and then a company that eventually merged with the global telecommunications-services firm Nobel. Siminoff said he likes businesses where he can “set it and forget it” – do the work of starting it up, and then let it continue on and make him money.
Siminoff’s visit to The Met was the brainchild of Jodie Woodruff, director of The Met School’s Center for Entrepreneurship. After seeing the young CEO’s story on the BNET.com show “Dog and Pony,” Woodruff began using him as an example in the classroom, and eventually decided to send him an e-mail inviting him to speak to her students.
“Jamie’s presence in school was exciting,” said Dennis Littky, co-founder and co-director of The Met School. “He showed the students how a regular guy, by working hard, not taking ‘No’ for an answer, and following his passion, could be very successful.”
He certainly had an attentive audience in the ninth- to 12th-graders in the school’s entrepreneurial program, who peppered him with questions about starting his own business, his hopes and fears and some of the basics of adulthood.
Although he made sure to focus on the rewards of being an entrepreneur, Siminoff was honest about the challenges it involves, saying he never forgets that 70 percent of businesses fail, but also never lets it hold him back. Flexibility is key, he said. “Whatever you have, use it to your advantage.”
Starting a new business often involves lifestyle sacrifices, he said, recalling his first years out of college, when he was building a business, had no salary and still was living with his parents. He wondered if he had made a mistake in turning down a lucrative financial job.
“Being an entrepreneur is not about being the boss. It’s about being the guy who takes the trash out at 10 o’clock at night,” he said. “In some ways, you’re the lowest person.”
The hardest part of starting a new business is not getting the money, Siminoff said, but putting together an initial action plan that works. As an example, he pointed to a deal he made for one of his earlier companies with the telecom firm Vonage. The contract’s terms were well below the cost of running the company, and when the costs didn’t come down he was forced to wiggle out of the contract.
On the other hand, Siminoff stressed the importance of not talking yourself out of starting a business by inflating the risks involved. “Look at what your real risk is,” he said. “A lot of people over-think their risk.”
Siminoff also emphasized the need for good associates to whom responsibilities can be delegated. “People are not scalable,” he said. “You need to have other people.”
After his visit, Siminoff wrote a short post on his blog – jamessiminoff.com – about his visit to, as he put it, “this truly incredible high school. Let’s just say I was blown away.”
The Met said Siminoff may be a judge for the entrepreneurial program’s next business plan competition, and expressed interest in sponsoring students who want to go to college for entrepreneurship. •
