Tips from the Top: HeadRoom Event Spotlights Entrepreneurial Success

by i2n staff

An out-of-work tech salesman turned global watch manufacturer and industry tastemaker. A dyed-in-the-wool introvert who launched a first of its kind networking platform, helping more than 400 more users establish effective business relationships. A corporate marketing executive who quit on the spot when his boss demanded one too many flights out of state (and away from the kids).

These were a few of the people who shared their entrepreneurial success stories at HeadRoom in Media on Oct. 22. An evening downpour didn’t stop more than 40 aspiring entrepreneurs, small business owners, and startup enthusiasts from converging at the coworking office for the event.

“This series is about showcasing some of the best entrepreneurs in our community, allowing them to tell others about their eventful and often adventurous path to ultimate success and personal fulfillment,” said event organizer and HeadRoom founder John Tooher. “There are a lot of people who are curious about starting their own business. And we want to encourage that energy.”

The panelists included:

  • Josh Irons, CEO of River Avenue Digital, a digital-first marketing agency that brings clarity to digital marketing and client acquisition strategies
  • Sara Rosenberg, founder and ‘Connector-in-Chief’ of Powermatch, a business networking platform
  • Ellen Thompson, CEO of ResultsRepeat, whose companies have been listed on Philadelphia 100 fastest growing companies 9 times
  • Chris Vail, serial entrepreneur and founder Lew & Huey and NTH, two wrist watch microbrands that have grown by double digits each year since 2012.

Topics of discussion ranged from why they chose to start a business to their first big break and common mistakes they see other entrepreneurs making.

John Tooher, far left, leads the panel discussion “Tips from the Top” at HeadRoom in Media

The panelists talked openly about their own mistakes, and in some cases the temptation they felt early on to give up. One example: a panelist admitted not knowing he had to pay income tax—and then received five-figure tax bill in his first year. Many, too, agreed that their company had pivoted significantly from its initial concept, and that that adaptability was key to success.

But, they each agreed, now that they had a taste of being their own boss, they could never go back. “I hope it works out, because by now I’m completely unhireable,” joked Chris Vail. “There is no backup.”

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