Lessons Learned: SimulScribe CEO James Siminoff on raising too much money

Shortly after SimulScribe CEO James (Jamie) Siminoff co-founded his company, an article in the New York Times gained the voice-mail transcription startup a lot of attention.

While many startup execs would kill for that situation, Siminoff explains in this interview with Vator.tv's Bambi Francisco how it led to SimulScribe accepting more angel investor money -- $4 million -- than it needed at the time.

"You take money when you can get it," Siminoff says, while adding that the large amount of cash was a mixed blessing.

While it helped the company grow quickly to revenue stage, SimulScribe soon found itself at a size that was tough to sell to investors when it started thinking about another financing round: too big for seed investors, but not so large that Series A investors were interested.

"The middle is a tough place to be," says Siminoff, who's on his third trip down the startup path.

The company, founded on just $200,000 put up by Siminoff and co-founder Mark Dillon, is now generating $2 million in revenue.

Still, "it would have been nice to have just raised about $500,000" in its second seed round, then have done a Series A round, "to put the right group (of VCs) together," Siminoff says. 

To hear more about the company's software, which lets users read their voice mail rather than having to wade through all their phone messages, you can watch this Vator.tv interview.

Other pieces of advice from Siminoff:

- don't give up, because "you only fail if you stop,"

- don't get too excited by the highs or down on the lows, and

- admit mistakes quickly and correct them.