Craziest Place to Close a Deal

Making a Deal on a Biplane Deal

In a biplane, on a fishing boat and hanging out at a bar all sound like great places to be with friends and family, however for these entrepreneur’s they did more than just “hang out”, they made business deals that lead them to making thousands of dollars. Meet these entrepreneur’s and the craziest places they made deals:

  • Name: Lia Grimanis
  • Company: Up With Women

Every year, Lia Grimanis challenges herself to do something daring — go on a shark-feeding expedition, learn to pilot a helicopter, climb inside a glacier. “It was how I readied myself for whatever challenge lay ahead,” she said.

Risk-taking is a quality that helped Grimanis through some of the toughest periods of her life — like growing up below the poverty line and living in a homeless shelter as a teen.

In June 2011, she was working as an independent consultant when a tech company approached with a job prospect.

“They flew me to England to finish the final negotiations. So I took the opportunity to also fulfill a lifelong dream of wing walking on a plane.”

In fact, Grimanis was strapped to the top of a biplane and about to take off when her phone rang. “I wouldn’t have heard it if I was already in the air,” she said.

She took the call, talked through the fine points and accepted a contract position at the firm — and then the plane took off.

Making a deal in a helicopter deal

  • Name: Jim Angleton
  • Company: Aegis FinServ Corp.

In June 2012, Jim Angleton was stuck in Miami traffic when a helicopter whizzed by. It sparked an idea.

Angleton’s financial advisory firm was in the process of closing a $15 million deal for its new headquarters.

“In South Florida, the tax rates for such deals are very high,” said Angleton. “We had sticker shock when we realized how much we’d be paying in taxes.”

He thought about flying all parties to the Bahamas to avoid U.S. taxes. “But it would have cost us $100,000,” he said.

But when he heard the helicopter fly by, he thought: Why not rent a helicopter, fly offshore to the international shipping lane and sign the deal in the air?

“We were 3.5 miles out, hovering 500 feet above water, with six people in the helicopter,” said Angleton. The entire trip took 20 minutes and cost him $23,000.

“But we saved more than $400,000 in taxes, and we didn’t break the law,” he said.

  • Name: Chris Herbert
  • Company: Phone Halo

Chris Herbert never would have guessed that a friend’s bachelor party would yield an investment in his startup.

Herbert co-founded Phone Halo, which makes wireless tracking devices that attach to easily lost items like wallets, keys or remote controls.

Last year, Herbert joined a group of friends for a surfing trip to the central coast of California. On the beach, they met another surfer.

“I threw him a beer and we all went surfing,” Herbert said. Later that day, Herbert found out the man was an angel investor looking to put money in a startup.

“I had just returned from a business trip and still had all the paperwork I needed in my car,” Herbert said. “I whipped out the term sheet and we struck a deal for a $25,000 investment.”

  • Name: Bill Bauer
  • Company: Royce Leather

A family vacation last June produced “one of the oddest coincidences in my life,” said Billy Bauer, a marketing director at his family’s company Royce Leather.

“My family are big outdoorsy people,” he said. “Fishing is what we look forward to doing wherever we go on vacation.”Bauer was on a marlin fishing trip off the coast of St. Martin when he got into an argument with his brother over a new wallet they’d developed with built-in GPS and theft-protection technology.A buyer for a major industry catalog was also on the boat. “He overheard us talking about our wallet and wanted to know more,” said Bauer.

That conversation led to a $40,000 deal.

Read about more crazy places and where other deals were made from money.cnn.com.

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