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The pivotal moment that inspired Boardroom Insiders to bootstrap their way to success

At the Bull City Ventures annual conference in Raleigh a few years back, Lee Demby heard the story of a man whose fundraising pitch was rejected 38 times in a year. Two years later, that same man sold his business for $85 million.

“It was a pivotal point,” says Demby, co-founder of Boardroom Insiders. “I called [my co-founder] Sharon and told her, ‘This is a make-or-break moment.’ I can go out and kill the company by trying to raise money, or I can spend that energy, bootstrap it and continue to get customers.”

It’s a question all startup founders face at one point or another: Do you seek outside investment (and accept everything that comes with that)? Or do you bootstrap (and accept full responsibility for your business’s financial stability)?

And it Demby and his co-founder, Sharon Gillenwater, came face to face with that questions five years into building Boardroom Insiders, a database of executive profiles designed to help sales professionals sell.

The idea for Boardroom Insiders came more than eight years ago, when Gillenwater was asked by the CEO of Sun Microsystems to put together a dossier of people attending a CIO golf tournament. The 200 bios she researched and composed became the foundation of the database she created with Demby that now includes over 16,000 profiles of C-suite executives in Fortune 500 and Fortune 1,000 companies.

These profiles are invaluable to sales and marketing professionals as they seek to pitch to industry executives, a population that is notoriously difficult to sell to. The concept behind the database of profiles is to simplify the pre-sales call preparation for sales professionals while maximizing the background knowledge on each potential customer.

The database includes biographies of the top five C-level executives — CEO, COO, CFO, CIO, and CMO — and focuses heavily on technology companies. Customers pay an annual subscription to access the bios, a fee that includes credits to request new bios not currently in the database.

When the duo met in 2010, Gillenwater had 800 profiles completed. Putting in place a sales and marketing strategy, they grew exponentially as customers requested and suggested additional biographies.

Then, in 2015, the founders went in search of funding. About the same time, Demby attended the conference in Raleigh that would shift their focus entirely. The story of that man with three dozen rejections inspired them to bootstrap, and the company has done so ever since.

“If you’re going to [fundraise], do it very early when you don’t know much about your business,” he said. “The daily grind of going out, prospecting and trying to grow your business while at the same time trying to raise money is exhausting.”

Headquartered in Fort Mill, Boardroom Insiders is growing their team of eight full-time employees, they also have 10 to 15 contractors around the country. Demby is president of the organization and handles all the day-to-day functions, including leading sales efforts. Gillenwater works from San Francisco managing the editorial side, including serving as editor-in-chief and marketing lead. Recently, they partnered with Dualboot Partners – a Charlotte-based strategy, design and engineering services firm – to maintain their platform.

The company has hit its stride, but that took time — more time than Demby expected.

“On the heels of participating in a successful exit of a very similar business model, I thought entrepreneurship would be easier,” he said. “I thought we would sacrifice for a year, and within two years, we would have it under control. In reality, it took five years to become profitable.  Just because you did it before does not mean the next time will be a slam dunk”.

Now, his advice for new entrepreneurs is to embrace uncertainty and make quicker decisions.

“Be extremely comfortable with ambiguity,” he said. “A lot of entrepreneurs get stumped, whether they are bootstrapping or fully funded — because when you are not making any money it is easy to panic and pivot in a lot of directions with very little data or insight.  Not everyone can do it, but the more you can let things play out, the more confident you’ll be in your pivots.  Timing is everything.”

This story was written by David Stunja and Lexie Banks.

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