04/07/2014 09:47 BST | Updated 03/09/2014 06:59 BST

An American Entrepreneur in London

She had no idea that this was going to be the plane ride that changed everything.

Penny Wing had recently quit her job as a statistical analyst in engineering after agreeing to marry the President of the company. On that plane ride from New York to Los Angeles in 1980, she sat next to the owner of a travel company.

She mentioned that she was recently out of work. She also mentioned that while she had an American accent and passport, she had lived in 36 different places by the time that she was 21.

By the time the plane had landed, he had convinced her to come and work for him. She spent the next eight years in the incentive travel industry, honing her skills and learning the space.

In 1988, she started her first company in her living room with $30,000 in savings.

Two decades later, she has started and sold three companies in the incentive travel space, the last one selling for $15 million.

We were lucky enough to host Penny and her business partner Oliver Codrington at a recent Escape the City event ("How to Start & Sell a $15 Million Company") and I walked away thinking about American optimism, a Fleetwood Mac song, and how so much of life only makes sense when you read it backwards.

That American Optimism

Being neither American nor British, I only started noticing the cultural differences between the two after spending a few years in London, where I spent large amounts of time around both groups. As British comedian Tom Cowell put it:

"Americans are so wonderfully, sincerely down-to-earth, we have trouble believing it. To the cynical British mind, any genuine pleasure in meeting a new person is a sign of potential mental illness. But Americans actually want to make new friends. They want to get along with you, stranger. It makes one's like infinitely more interesting to have an American around, because you meet EVERYONE. It's like permanently going through life with a puppy, or the latest iPhone."

Life has been more interesting with Penny around. I've known Penny for over a year, after meeting her on our Startup MBA. She has taught me that learning how to start a successful business is largely about learning to become a successful founder.

Ideas are a dime a dozen - anyone can steal your idea. But every business is a reflection of the founder's ability to execute. Mindset steers that ability. So maybe learning how to start a business is about learning how to groom your mindset to become better at improvisation, which is essentially what entrepreneurship is.

When I stereotype the American startup founders I've met in London, I notice the gene that they seem to share with Penny - that American go-getter "shoot for the moon and even if you miss, you'll land among the stars" mindset. (Somewhere, my British friends are rolling their eyes at that cheesy quote.) Americans don't seem scared of their own idealism, whereas in British culture, I find brazen optimism often equated with stupidity.

While I barely passed physics and never read The Secret, I do believe in the law of attraction. From listening to Penny's life story the other night I became convinced that a huge part of her success would have come from the positive force field that her "Dreams? I got 'em! Failure? I'll recover!" mindset must create: resilience is a necessary entrepreneurial trait.

"Go Your Own Way"

Although Fleetwood Mac's song is about a breakup, whenever I hear it, I always think about Richard Branson, Steve Jobs, Blake Mycoskie and Miki Agrawal.

Entrepreneurship is about paving your own path, going your own way, making money and creating a life in the way that you define for yourself, instead of relying on an employer. Maybe that's why it has so much appeal for a generation who has less faith in institutions than they do in themselves.

This goes for the bigger actions like starting a company as a deed in itself, but it also applies when it comes to how you handle each new pitch and client. When you're an entrepreneur, you don't have a manager telling you how you should be doing things. You've got to figure it out yourself and the more willing you are to do things differently, the more likely you are to stand out.

Penny won her early clients not by sticking to the rules but by deliberately breaking them (after she had spent years learning them).

In the incentive travel industry, the 'typical' pitch to a Fortune 500 company tended use a 50-page typed up proposal. "We will take your group to (this city) using (this hotel) with (this budget)." (Expanded upon for fifty pages. Of text.)

Penny understood that travel was a sensual experience. For a proposed trip to Mexico, she walked into the boardroom with an entire Mariachi band, a tray of Enchiladas and a sign that say "Going for the whole Enchilada".

The proposal was a visual storyboard full of pictures, and simple one-page budget. She walked out with a million dollar contract.

Penny decided to start up another venture (Brojure) last September when CBS Television asked her to create an event for them. She decided to hire a developer to create a piece of software so in a moment of creativity, she could quickly design a digital storyboard herself without a graphic artist and have it on her customer's desk the next morning. That idea developed into a rich content proposal e-magazine.

"I wanted to deliver a Vogue-type proposal to inspire my customers," she says. It turned out that several companies from wedding planners to real estate to yacht brokers loved the software. Brojure is cloud-based, simple to use and visually appealing.

Life, backwards

Karma obviously isn't a financing strategy discussed in business textbooks, but it's one explanation for a bizarre set of events that occurred at the outset of Penny's first company.

She had just gone to pitch for a large client who wanted to award her the work but couldn't do so because "you're a scrappy startup, this is a huge account, we'd love to give you the work but we can't".

"Not to worry! I'll be back next year and I'll win that work next year, as I'll be bigger then!" Penny replies. (American optimism. See above.)

But she didn't have to wait a year.

The next week after the meeting, Penny was hosting a friend and lent her the car along with some cash. To thank her, her friend bought her single rose and a one-dollar lottery ticket.

The lottery ticket won Penny $250,000. The news was printed in the local paper. The Fortune 500 client saw the news in the local paper and called Penny back and awarded her the work. Even though Penny never used the $250,000 to finance the company, the fact that she was now "financially stable" meant that she could be awarded the work.

From the plane ride to the lottery ticket, Penny's story is a reminder that so much of life only becomes clear when you view it backwards. It's impossible to see, looking forwards, what the future holds - even though that's what so many people come to our events aiming to discover - secret 'tips', instruction, guidance.

Ultimately Penny's success seems to stem from a trust in something larger than what the eye can see. Like Steve Jobs once said:

"You can't connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something -- your gut, destiny, life, karma, whatever. This approach has never let me down, and it has made all the difference in my life."


Escape the City is an online community dedicated to helping corporate professionals to do something different. We run regular offline events via The Escape School - the career, life and startup education you never got at school.