TVC068 Play Bigger Influencer Al Ramadan

al ramadan business vitality category ceo entrepreneurs fitpreneur influencers leadership play bigger podcast silicon valley success tech Dec 03, 2016

TVC068 Play Bigger Influencer and Innovator, Silicon Valley's Al Ramadan

Welcome back to the Influencer Fitpreneur Series. 

I'm honoured to have a special guest on the show,  Play Bigger co-author and true innovator, Al Ramadan.  

Co-founding partner at Play Bigger Advisors, Al has been a CEO, Entrepreneur, Operating Executive and Sailing Technologist.

He is also a mentor, father and favourite uncle to an ever-growing circle of next-generation superstars.

I met Al when we were both on a fabulous island in the Pacific, Namotu, and he was just about to launch his new book - Play Bigger; how Pirates, Dreamers and Innovators Create and Dominate Markets.

A true definition of a Fitpreneur,  I hope you enjoy listening to this episode, as much as we did recording it.

Al in San Fran and me sitting on the opposite side of the globe in Australia. At the time of this podcast recoding, Play Bigger was announced as one of the top 5 in leadership and strategy books in the US for business.

It's been a hell of a journey. Al Ramadan

An Influencer From The Start

In the early '90s Al applied data science to Australia's Americas Cup by showing data along with video - an innovation in sports performance analytics. As a result of this work, Al co-founded Quokka Sports, which pioneered data-intensive sports immersion on the Internet and revolutionised the way people experienced sport.

He then joined Macromedia - and Adobe,  after Adobe acquired Macromedia, where he spent almost ten years changing the way people think about great digital experiences on the Web and on then-new mobile devices.

At Adobe, Al led teams that created the Rich Internet Applications category and helped develop the discipline of experience design.

Collaboration and Consciousness

In 2011 Al started up his current big project, the company Play Bigger Advisers, with his 2  'brothers in life',  Dave Patterson and Chris Lochhead. This new project meant the reach of knowledge and shared experience was going to go broader and make a bigger impact than ever before.

 "At Play Bigger, we help those that are already successful in venture capital, already established, take their businesses to the next level, to the ultimate transcendence"

Play Bigger authors Dave Peterson, Christopher Lochhead, Al Ramadan, and Kevin Maney

Al states that working in co-category design is a unique discipline. It's a new thing, just like product design, company design, industrial design, experience design, all of these design methodologies have appeared over the course of the last 20 or 30 years. 

The wonderful thing about silicon valley and everything else is creating something before the market even knows where to put it, and that's often the challenge of innovative minds, is that they have an idea that doesn't fit in a box yet.  

People,  when purchasing, like to think in categories, so you may not realise it but category design is one of the leading product development areas in our day to day world.

From cereals to diary products, washing products to bikes and cars.  For example an SUV is a category. 


Writing Play Bigger The Book

Due to their innovation and experience in Category Design,  Play Bigger advisors were repeatedly asked by people to do projects and they just couldn't accept them - "we were too busy". So this sparked the idea for Play Bigger the book.

"We all thought collectively, the right thing to do is to try and get this discipline articulated in the form of a book". 

The next step: Collaboration on a whole new level.

Al, Chris and Dave, bought in legendary author, Kevin Meaney who wrote the definitive guide to IBM and many other great books.

The 4 of them spent 9 months working on this project.

  • The team approached writing the book like you would write an album. When it was live, published and reached the top seller charts in America for Leadership, they were able to recognised the effort they had put in and the impact they had created.
  • Their publisher for Harper Collins in New York quoted "it's not very often we choose authors where there's 4 of them, it's a really unusual scenario".  It worked.

It worked because we were great friends, Chris, myself, and Dave. It was one of those events and projects in life where you look back and think, "Oh my gosh, you know, we really did something," and you can hold a chunk of book in your hand, sort of say, "Here it is, it's all written down."

Every CEO and entrepreneur looking to reimagine their business can learn from this book. Play Bigger is for thought leaders and innovators with a track record for intuition and market awareness, looking for a framework and new perspective on category design.

Blending Healthy, Wealthy, Wise

Al loves the outdoors and remote expeditions. He has hiked the historical trails, sailed in the Sydney / Hobart yacht race, surfed Mavericks, lived on remote atolls in the Pacific and Indian oceans and can often be found bombing back country lines around Tahoe on a split board.

The Play Bigger advisers team all value this need to step away and ensure moments to calibrate and be creative.

The outdoors and 'off the grid' about regenerating, getting creativity back and just switching off.

Some of Al's trips have included hiking the John Muir trail -  a 22 day hike along the spine of California called the Sierra Nevada Range - are just as much about a connection to deeper wisdom as it is to a love of adventure.

...Hiking the John Muir trail in 2010 was my thing for myself... It's insane, it is one of the greatest things that you can do in your life, it is a remarkable journey.  350 km's plus or minus, and you go across the big passes of the Sierra and you ultimately finish the trek on top of Mount Whitney, which is 14,500 feet, plus or minus. The highest mountain, or the roof of North America, as we call it. That was an incredible exercise, I had friends join me all the way along, bringing supplies in and taking stuff out.


Listening to yourself and the market:  3 Key Play Bigger Tips from Al for CEO's and Entrepreneurs

1. Listen to your gut: The thing that's most missing in the world is insights, someone sees a problem, whatever it might be. The guys at Uber thought it would be standing on a corner, trying to hail a cab was a dumb idea, and they created this whole new thing, they had this founding insight.

  • Al's advice; If you really feel like you have identified a problem and you've got a solution or an idea for a solution, get out there and do it. There's nothing stopping you from doing that.

2. Trust your crazy ideas and work on them until they are tried, tested, tried tested and be prepared to try and test again. Plug into the community that make the decisions, the influencers and the investors and the idea makers. Share and refine with those whom you trust.

  • It's not like it's a simple exercise either .. I had to pitch to 20 different VCs the idea of Quokka before one of them even returned anything after the meeting.
  • That's part of the gauntlet that you have to run as one of these crazy entrepreneurs, and it's also part of the whole process. Every time you meet somebody, they critique it, say, "That's dumb, or this is silly," or whatever you thought about this. That just improves the way you think about this, and so if you've got it in your head, we call it a founding insight.

3. Think about what others need - not what you want to sell.  The fundamental element in success is recognising a key problem that exists and creating a viable solution for it.

  • Before anything else can happen, you've got to see a problem, whether it's a market problem or a technology problem, and then you've got to get after it and try and solve it.

 Pressing Pause

When C-Suite individuals exude consistent qualities of being ultimate leaders in business and in life. Healthy, Wealthy and Wise.  I personally,  call this the leadership trifecta.

A Fitpreneur. In fact that's the core of what I coach with CEO's and high achieving entrepreneurs. It doesn't need to elude you - it's about mastering the flow along the way.

Al is one of those unique people who never stops learning, applying, creating and giving back. Of pressing pause and being curious about what else is possible.  It is a privilege to have  guests like Al on the show.

For all his success, the ventures and the journey,  Al has a resounding authenticity and connection to those around him and what he does.

  • If you have any questions, comments, feel inspired or want to get in touch please leave a comment.
  • Links for the book and more details about Play Bigger can be found below.


It's not everyday we get to hear from people who are pioneers in their field; not early adopters, but the creators.  I hope this podcast with Al has inspired you to think big, to think categories and designing a life and a business you love.

Leave a review here on iTunes or subscribe for more.

Yours in Vitality



Play Bigger the Book

Amazon Play Bigger


Play Bigger official


John Muir Trail 

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Nov 01, 2023