Shaw certainly fits the bill. He has a Harvard Business School MBA, runs 5k every day and has been a top exec at Skype and O2. But there is a lot more to him than meets the eye.
It is a surprise to learn Shaw's first jobs while at high school in Arizona were as a gardener, cleaner and door-to-door salesman.
Shaw's parents had their own retail furniture business, and observing them evidently played a big part in his formative years. In fact, seeing how hard they worked put him off being an entrepreneur.
Cleaning job 'real eye opener'
The cleaning job was evidently a hugely instructive experience for Shaw – in particular observing the founder and how she grew the company to about 60 employees over the two years he was there.
"I watched her be incredibly successful. But, she got involved with the wrong crowd. She started taking drugs. She did some very stupid things. Over a two year period, it went from amazing boom to not receiving my very last pay check, which was just as I was going off to university, thinking, I need this money," he says.
Shaw also says he found the experience of going into people's homes as a cleaner to be "a real eye opener".
"Some people were wonderful. Some people were just rude, obnoxious, even abusive," he says.
Shaw spent four years studying business, economics and Spanish at Washington University in Missouri, an experience he "absolutely loved". A particularly fond memory was meeting the famous Argentine writer Jorge Luis Borges.
After graduating, Shaw headed to Los Angeles to work for Ernst and Young (then Ernst and Whinney). He'd been accepted onto an MBA programme at Harvard Business School, but had been told to get two years' experience before enrolling.
Although he "hated accounting", Shaw loved the experience of living in Los Angeles in his early 20s. He lived with two friends in West LA, about two miles from the beach.
"You just got this real melting pot of different ethnicities, different foods, and the beach is nearby. If you want to go skiing, the mountains are not far away. Loved it," Shaw says.
"We had an amazing time, we threw amazing parties. We lived on Barrington Avenue in West L.A. and all of our friends called us the Barrington Boys. It was just a wonderful place to live," he laughs.
A 'lovely English woman'
When the two years were up, Shaw headed to Boston to take his MBA.
"I loved Harvard Business School. I hated Boston. But the one really good thing about it is that's where I met my wife which is why I'm here [in the UK]," he says.
At first Shaw was worried he wouldn't enjoy the course. Half of the grade is based on exams and the other half is based on class participation, so he decided to turn up half an hour early on his first day to secure a good seat.
"I walked in, classroom of 90, there were five empty seats. The first people arrived at 5am to get the best seats. Theoretically that's the middle where you're in the professor's eye line more regularly.
"You know, I mean, I'm thinking, "Is this what I left Los Angeles for?" To come to this?" he says.
On the plus side this meant Shaw sat in the empty seat next to a "lovely English woman" called Lesley.
"It took me four months to ask up enough courage for her to go out on a date with me. And she said no. But very American of me, two weeks later I did try again and she said yes," he says.
After getting engaged, the pair moved to San Francisco, where Shaw worked for American Express, eventually becoming vice president.
Moving to the UK
With his wife's visa due to expire, the couple had to return to the UK. Thankfully both were lucky enough to be able to continue working for the same companies during the process.
"We thought we'd be here for a few years, and here we are 25 years later. This is home. This is my life. London is my city, my three sons are here," he says.
Shaw moved from American Express to investment firm Charles Schwab, but decided to quit the financial sector after the dotcom bust.
This is the point where Shaw decided to move into the technology sector, specifically NTL (now owned by Virgin Media).
He was one of six directors, running London and the southeast. But within six months the company had to file for Chapter 11 bankruptcy. "It was becoming profitable, but it was running out of cash. We had to start a turnaround," he says.
Shaw's next role was CEO of a late-stage startup with 150 employees called MobileWay.
"That was my first real taste of being the CEO, being accountable to a board of directors. I never worked so hard in my entire life," he says. This also proved to be his first of three startup exits.
"I got my equity. Sadly it wasn't enough to retire forever on some exotic island. But it was a good taste of the startup world and it was my first real exposure to Silicon Valley," he says.
Shaw's next move was back into a bigger corporate environment as chief marketing officer of O2 (now Telefonica).
It's thanks to this that Shaw has his name on the contract for 'The O2', then called the Millennium Dome, in 2005.
"That's where ideas like priority ticketing were born, because the whole focus at O2 for me at the time was, don't just focus on the new customers and customer acquisition, it's how do you drive customer loyalty? How do we keep existing customers happy?" he says.
Much to his relief, the deal ended up being a success. In fact, it's recently been extended for another 10 years.
"We were so pleasantly surprised at how people embraced calling it the O2. We thought it would take years. And it took months," he adds.
Shaw's next role, as global innovation director, saw him set up a fund to invest in startups and launch incubators. "The seedlings of Wayra started when I was there," he says.
"There were a lot of senior people at Telefonica who didn't quite get what I was trying to do. There was one gentleman who did. His name was Jose Maria Alvarez-Pallette, who is now their chief executive," Shaw adds.
After a couple of years Shaw moved to Skype to run its EMEA division and set up a mobile department.
"It is a fascinating company. I loved it. But I had four bosses in the span of two and half years while I was there. So there was a lot of management team turnover," he says.
Shaw left when Microsoft acquired the business: "That was my third exit, thank you Microsoft. That was wonderful! Many of us did very well from that. But I thought: 'three times lucky. I'm not going to do the corporate gig anymore'," he says.
Tech London Advocates
Sadly at that time Shaw's wife's health took a turn for the worse. "I decided to be a bit more grounded in London, and to be around my wife. Some months are good. Some months are not so good. She has a chronic form of leukaemia, which makes her immuno-suppressed," he says.
They now spend a lot more time together. They visit the theatre every week, have regular nights in watching the telly (the BBC's Line of Duty is a favourite) and see a lot of their sons Matt, Chris and Daniel.
Choosing to travel a bit less ultimately contributed to the creation of Shaw's latest venture: Tech London Advocates. The independent group, launched in 2013, brings together individuals working in tech in the private sector with the aim of promoting London as a tech hub. It's free to be a member, and advocates join via introduction.
"When I turned 50 [in 2012], I became an entrepreneur for the first time. I was nervous about it. But I am accountable to myself. I have some wonderful people who work with me," Shaw says.
TLA has gone from under 100 to over 4,600 advocates in just four years, has over 30 sub 'working groups' and affiliate groups in eight other countries to promote their local tech sector.
"It's got all the high profile people and leaders and names that you know, but it has all kinds of people: artists, students, secondary school teachers, designers. People from all walks of life that really, I think, make the DNA of the group. It’s wonderful," Shaw says.
Shaw is generally unremittingly positive about London and the tech sector. However he admits it is far from perfect. Although he doesn't specify the company, Shaw says he was bullied in one of his roles previously.
"I should have left sooner. I was bullied verbally and mentally. I wasn't the only one, quite a few of us were," he sighs.
"People deal with it, they have mortgages to pay and kids to feed. But I think I my biggest regret was not pushing back more firmly. Or making a decision sooner rather than later to say: 'I'm outta here. This is fucked up. I don't want to be a part of this'," he adds.
Shaw has learned to trust his own gut instincts over the years in response, he says.
"It's taken me years to feel confident enough to that point where I could trust it if something is not right inside. Some people you don't have to say that to. Some of the young entrepreneurs I meet, they're like that and they're 22. And I'm like "God, I hate you!" Shaw laughs.
At 54, Shaw says he is at the "highpoint" of his career.
He adds: "I set a benchmark for myself. When I turned 50, I said that when I turn 60, I want London to be known as a world-class and world-leading technology hub. That is my gift to give back to London, which has been great to me. This is one of the best cities in the world, if not the greatest".