Executive Leadership Programs



12 people. 1 garage. Endless creation.

You gain so much power from a mastermind event. It’s a chance to bring together people from all kinds of industries and backgrounds. Guards drop, hard questions get asked and passions soar.

Find out about the 3 biggest takeaways from Shawn Shepheard’s mastermind event hosted at LinkedIn headquarters in Toronto.

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From the Huffington Post

My Confessions After Committing to a Mastermind Business Group

For a long time it was snake bites. After that it was death by drowning. In between I defaulted to various embarrassing social scenarios.

Our mind can create all types of fears… some of them real, others not so much.

When it comes to my new career, I have been fearful from the start.

A few years back I decided to take the plunge, throw social norms to the wind and left my long-time career as a journalist.

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From the Huffington Post

Stop Acting So Small- Why Business Dreams Die

Is this another one of those inspirational, rah-rah, let’s all be positive and chase our dreams quote?

Yes. It is.

Are you rolling your eyes?

If I read this 5 years ago, I would have felt that this was just another fluff saying for people who didn’t live in reality.

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Team Leadership Programs
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Shawn Shepheard - Business Strategist

Book a Complimentary
Strategy Session Now


Shawn taught us about presentation skills. He was exemplary in preparation and execution. We changed our behaviour with how we create presentations. The prework he developed made our training session very productive. Shawn's follow-up was astounding. He asked us how well we were implementing the new skills we acquired. He also provided numerous published references for us to use to keep the training alive.

Post one year training, Shawn supplied further resources, and reminded us of the main tenets of our training. There are not a lot of sessions I have had where I am using the material immediately and am still using it today (as well as the rest of group trained).

The preparation, execution and follow-up, are some I have not seen with other training/educating organization. Shawn is a wealth of information.

—Richard Forster
National Sales Director for Animas Canada

I had the privilege of hiring Shawn to coach my team here at LinkedIn and it was very successful. He received the highest NPS score of the year. Shawn offers a unique perspective and brings content to the table in a way that is both engaging and easy to replicate. I've also had the opportunity to work with Shawn outside of my current role and will continue to do so into the future.

—Perry Monaco
Manager of Customer Success

Business Strategist
and Coach

Shawn and I have worked on and on for more than a decade. And through that decade, I opened two restaurants in New York City, given two stars by The NY Times, featured in an international documentary, wrote a critically acclaimed best selling cookbook, left a relationship that was not working and now I’m well on my way to becoming POTUS! Well, that last part isn’t in my sights but knowing Shawn, if it were, he’d help me get there. Now, my dreams have always been my own, and he helped me prioritize what was important, encouraged me and helped me get to my dreams with integrity and character. Now, in my second act of this three act play, I’m working with him to find out what I want to commit to as my next projects. I can’t wait to see what’s next.

—Nicole Ponseca
Founder - Maharlika Filipino Moderno NYC
As seen on The Chew, New York Times, The Huffington Post, Time Out New York

My professional success and personal sanity this year can be directly attributed to Shawn's coaching. No self-help, productivity, or leadership book will provide the personalized actionable items to uncover what matters - it's Shawn's guidance and accountability that will transform the way you think. His coaching sessions have been a key component to fundamentally changing the way I not only work, but live purposefully.

—Christel Marchand Aprigliano

I attended Shawn Shepheard’s Mastermind session at a point when I was in the process of changing my business model. I thought it might help me with the change but I had no idea how much it would help. Shawn’s coaching helps you to think about the very core of your issues, both professional and personal and to confront them and deal with them. The session was of immeasurable assistance.

—Robert Stevenson
Whitecrest Consulting

Plus Much More


Topics Inlcude

  • Being Remarkable & Standing Out from The Crowd
  • Making Strategic Focus A Daily Habit
  • Re-Imagining Work – What is Possible Now?
  • Developing a Coaching Mindset
  • Breakthrough Thinking


Clients Include


For several years the highlight of our annual conference has been Shawn Shepheard. The audience is laughing one moment, dabbing at a tear the next and all the while being challenged and inspired. He delights all ages and backgrounds and his message is universal. At a recent conference, an octogenarian said, "Shawn teaches me something new about life each time and I am so energized now!!!" And THAT is why we have him back each year.

—Casey Truffo
Be A Wealthy Therapist
Orange County, California

Diabetes Speaker, Author & TV Host

Sugarfree Shawn

The Latest Episode of Sugar Free Shawn


See the full list of shows


Life is Sweet book

“If everyone laughs at you and thinks you’re crazy, that’s a sign it’s a good idea.”

— Shawn Shepheard

It’s Christmas morning. And instead of sitting under the tree opening presents, you’re sitting in a doctor’s office absorbing the news that you have Type 1 Diabetes. Probably not the best gift you’ve ever gotten.

So what do you do?

If you’re Shawn Shepheard, you decide to squeeze every last drop of joy out of every moment you have on this planet.

And then, you go back for seconds.

“Life is Sweet” is a look at some of the most heartwarming, hilarious and flat-out insane moments of the life of internationally-known speaker and star of “The Sugar-Free Shawn Show,” Shawn Shepheard – a life lived right up to the edge, and occasionally, over it.

Highlights include:

  • The time he took over a good friend’s radio show. And bombed. Badly.
  • His first near-death experience.
  • The time he got a roomful of stuffed-shirt business execs to shake their booties to ABBA’s “Dancing Queen” – and accidentally launched a company tradition.
  • The time he went shoe shopping for his first pair of high heels.
  • His second near-death experience.
  • The time he shot the first episode of his brand new show…with a bunch of zombies in the background.
  • And more…

Packed with real-life stories, anecdotes and observations, “Life is Sweet” will inspire you, surprise you, and most of all, make you laugh till you cry.

But sorry – tissues are not included.

Buy Now – $13.99