Because wealthy entrepreneuers need a hand, too

Married to the idea: When serial entrepreneur Ashley Heather and his wife, Diana, had their third child, they moved their life from NYC to the Hamptons -- and Heather's innovation lightbulb lit up.

The “flip” came around 2014, after Ashley John Heather and his wife, Diana, welcomed their third child.

Heather, a Brit who emigrated to the United States around 2000, had lived his entire U.S. life in New York City. But it was two years since he’d sold his successful e-commerce startup Dotbox to NYC holding company MDC Partners, about that long since he’d bought the house in the Hamptons, a few too many months of “the whole weekend thing,” he said, living and working in the city and trekking out east for down time.

When the young family grew again, Ashley and Diana “flipped our lifestyle,” Heather told Innovate LI, moving full-time to Southampton – where the kids now attend public schools – and working largely from home, with the occasional city trip to manage White Space Group, the mogul’s circa-2007 digital-creative agency.

The Hamptons Shuffle proved an eye-opener for the entrepreneurial émigré, who soon discovered that when it came to home-based businesspeople on the East End, he wasn’t alone.

“I was finding other people like me out there, who were entrepreneurs who worked from home,” Heather noted. “But there was no central community for them. That’s where i-Hamptons was born.”

Officially launched in March, i-Hamptons – a White Space Group spinoff – is self-billed as “the Hampton’s first community and resource guide for local entrepreneurs,” according to the organization’s website, busily “aggregating all resources that are useful to local entrepreneurs.”

“I call it a movement,” Heather noted. “The movement is about connecting together entrepreneurs and trying to identify the resources they need to be successful.”

In concert with The Spur – Heather’s 8,000-square-foot “private co-working and entrepreneurs club,” slated to open in Southampton next summer – i-Hamptons essentially aims to do what the LaunchPad Long Island network, the Digital Ballpark in Plainview and other startup-support systems have done for Island entrepreneurs, only to do it on the East End, not traditionally known as a hotbed of invention.

Even Heather admits the Hamptons is known better as “the place with the lawyers and the accountants and the weekend homes” than as an innovation hotspot. But that just adds to i-Hampton’s ambitions, according to the founder, who’s out to both organize the Hamptons’ entrepreneurial community and to grow it.

“The people exist,” Heather said. “We have our home offices or we all work at Starbucks. I’m bringing these people together.

“I’m also creating a resource so people will be more attracted to moving out here,” he added. “I want to bring additional families and entrepreneurs out to the Hamptons by showing they can do it, they can be out of the city and live at the beach with the good schools and still be successful in business.

“We’re all living in the digital economy now.”

First resort: Heather senses an entrepreneurial shift toward “resort towns.”

Heather hosted an i-Hampton launch party at a private home in July and a fundraising event for The Spur at the Southampton Social Club in early September (while he has self-funded i-Hamptons so far, he’s looking to raise about $4 million for the co-working space renovations, which include the creation of roughly 20 private offices, a movie theater and other amenities).

Both of the events were well-attended, according to the entrepreneur, who notes “more than 400 members have already joined the movement” – a running start for i-Hamptons’ under-construction entrepreneurial database, the heart of the resources-driven support system.

“The best part is, we are attracting all kinds of members,” Heather noted. “The techy people building in their garage. Small business owners. I have some investors.”

Growing the ranks remains a top priority, he added, and a challenge, since “this kind of innovation talent is different than what the Hamptons is known for.”

But membership is likely to swell around i-Hamptons’ next networking event, “Riptide: Hamptons Sink or Swim,” a “Shark Tank”-like entrepreneurial pitch-a-thon offering $100,000 in seed funds.

The event, scheduled for November (location TBD), will help build the i-Hamptons brand – and further promote The Spur, which in addition to flexible co-working spaces and a 70-seat theater will also feature a health-and-wellness studio, a “speakeasy bar” and other comforts when it opens in mid-2018.

Heather believes fate has dropped him on the doorstep of a golden opportunity. His personal family dynamics brought him to the beach, and introduced him to likeminded entrepreneurial thinkers there, precisely when the nation’s urban-centric society is poised for “a flip-flop” – with digital connectivity, self-driving cars and other technologies slowly shifting commercial focus away from cities and toward “resort towns,” according to the entrepreneur.

“People will spend more time in their resort homes than their city homes, because of the time saved and conveniences like self-driving cars, which will make resort towns more attractive,” he predicted. “People’s second homes will become their first homes.”

And that means a model like i-Hamptons – beefing up business-building resources in places where startups don’t necessarily need financing, but still need a networking boost – could become common, “if the one in the Hamptons works,” Heather noted.

“I’m trying to create the connective tissue between the 20-year-old who has an education but no job out east, the 40-year-old who has experience and is building a business and needs resources, and the retired 60-year-old who is successful and wants to stay connected to business but doesn’t know how,” Heather said. “This will be a community for those three groups to network, provide mentorship and grow together.”


What’s It? Networking hub/resources aggregator for Hamptons-based entrepreneurs

Brought To You By: Serial entrepreneur Ashley John Heather, who successfully flipped and is excited about the coming flop

All In: “Less than six figures,” self-invested by Heather, mostly to host launch and branding events

Status: Database growing, co-working space renovating, momentum building

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