Back in 1977, Billy Starr hopped on his bicycle and went for a ride. His mother had just died from melanoma and pushing the limits of the physical body helped Starr grieve the loss of his mother.

On one rather strenuous ride, Starr had an idea. He and his friends would make a weekend of cycling, but instead of just pushing their physical and mental limits, their pedaling efforts would go to raise money for cancer.

Starr had found a deeper purpose in life. It was now time for him to live intentionally and embrace it.

“I was an athlete. I wanted to merge some of the things that I had embraced as an athlete: the commitment, the sweat equity, the teamwork, the camaraderie (all of the things I had enjoyed about sport) and commit it to a higher purpose,” said Starr on arecent interview.

This year, Starr and his team over at the Pan Mass Challenge have set the bold fundraising goal of $45 million for Dana-Farber Cancer Institute and the Jimmy Fund’s lifesaving mission to conquer cancer.

Starr and his friends are inevitably responsible for the “a-thon” fundraising strategy popular in endurance sports like running, cycling, triathlon, or obstacle course racing.

What makes the Pan-Mass Challenge different from the many other “a-thons” out there is that fundraising is the core purpose of the event. And, of course, Starr created this fundraising model well before computers were in our living rooms (or in our pockets for that matter).

“But, most importantly, this ride, while being an inspirational physical, spiritual and emotional weekend, put fundraising at the center of the event. This was not about awareness. You carried a commitment,” says Starr.

Perhaps you have a cause that you too wish to fundraise for. In that case, here are five tips that Starr shared with me to have a successful fundraising event.

 “You got to do what you love.” @JeffreySlayter

“You only have so much life, so whatever you can do to create your own thing, get out and do it.” @JeffreySlayter

“That’s what it’s like as an entrepreneur – you have no idea if it’s going to work out and just put yourself out there and trust.” @JeffreySlayter


Let’s fly all the way over to Australia where Jeffrey Slayter now calls home. Jeffrey’s got a really unique background. Born in Hawaii into a family of entrepreneurs, Jeffrey eats, breathes and sleeps entrepreneurship, especially when he’s not surfing.

There’s so much I can say about this guy, but in short, he started up a bunch of businesses that have not only done a whole lot of good in the world – kudos to that – but also made quite a bit of money as well – double kudos to that.

His purpose-driven mission has brought him on the stage with Sir Richard Branson, Tim Ferriss, Tony Robbins – I mean, there’s so much that we could talk about today on the show.

Let’s have fun and dive into what’s got Jeffrey fired up lately.

It’s time to get real and vulnerable with Jeffrey Slayter – unplugged.

To learn about Jeffrey’s latest project, head over to

Jeffrey Slayter

On this Coffee Chat:

  • “No matter what, persistence, in the end, will win.”
  • Creating something out of nothing
  • Ideas are a dime a dozen, but execution is everything.
  • Anyone can become an entrepreneur
  • Finding what you’re here to do, not what the world is telling you to do
  • Having a daily routine – eating healthy food, listening to podcasts
  • Jeffrey’s Ayahuasca experience
  • What Ayahuasca can do for your business (and your personal life)
  • The future of conscious enterprise
  • “I’ve learned how little I actually know, and I’m okay with it.”


P.S. Are you on the mailing list?

CTA 650

I stare at a blank screen, my fingers hovering over ASDFJKL;. The cursor taunts me with its consistent blink, blink, blink.

Resistance… the plague which stops creators from creating, stops writers from writing, stops changemakers from changing, and stops entrepreneurs from launching.

Have you ever come up with an idea and felt such an incredible rush of adrenaline that you needed to grab the dinner napkin and nearest pen so you can scribble down the thought in your head?

What happens so often though is that we come up with these ideas and then just as they rise in a mist of fury, they just as soon fizzle as the resistance blows in like a trade wind.

What is resistance?

– Self doubt
– Overthinking
– Not knowing where to start
– Questioning your purpose
– Fear
– Feeling overwhelmed by responsibilities
– Time

My point in a shareable tweet: “Learn to recognize the resistance and say, ‘No, thank you. I’d rather move onward.”

 “There’s a difference between watching your life go by from the sidelines and just jumping right in and being a full participant in it.” @robertdomingo


Joining us in this episode of The Traveling Cup is Robert Domingo. Robert is the creator of Mid-Life Round-the-World – one man’s journey of preparing for, embarking on and returning from a mid-life round-the-world trip.

We are going to dive into his journey of how he came to go on traveling around the world, his passion for storytelling and balancing passion and practicality.

Traveling was something he’s always dreamed of but wasn’t able to do, being stuck in a job he just couldn’t quit. His blog tells his story of how he was able to do finally it and the stories and adventures he went through while traveling.

Robert Domingo

On this Coffee Chat:

  • Finding the courage to let go of things that hold you back
  • Taking risks and handling doubts
  • On traveling: “The worst case scenario when I come back is that I’ve gotten to see the world.”
  • How you can make the most out of your experience after traveling
  • Having a portable lifestyle business
  • Helping others fulfill their wanderlust
  • The balance between passion and practicality
  • How do you differentiate yourself from other entrepreneurs?
  • Getting over shyness and making connections


P.S. Are you on the mailing list?

CTA 650

 “The highest will and the highest purpose that any of us can assign ourselves to is finding our own happiness” @larendeeroos

The level of happiness and inner peace a person carries is not directly proportional to the size of their bank account. @dawndcoach


Join me in New York City where Larendee Roos and Dawn Doherty help executives maximize their leadership potential, all the way down to their spirit. They are the leaders of spirit-based business. That’s right – spirit-based business. Something I haven’t heard of very much before but after learning about it from Larendee, I love it.

We’ll be diving into what a spirit-based business is all about and finding happiness and peace in your own business.

Larandee Roos and Dawn Doherty

On this Coffee Chat:

  • A shoutout to Ken Woolley, a serial entrepreneur
  • The importance of mentorship in finding your purpose
  • The meaning of “relaxing into happiness”
  • What is a spirit-based business?
  • Transforming your life to transform your business
  • Finding your purpose and helping others discover theirs
  • How to deal with thought clusters or conditioned ways of thinking that are not serving you to move forward
  • How to attract people with similar goals
  • The secret to attaining sustainable wealth
  • The three questions you should be asking yourself
  • Finding what inspires and energizes you every day
  • Developing the trust muscle in business


Send your tweets over to @MarkWGuay and tell us how you are relaxing into happiness!

P.S. Are you on the mailing list?

CTA 650

The key to knowing your purpose is to believe you have one. We all have a purpose and sometimes the purpose is to grow. As long as you are growing as a person, you are on the purpose path.

My path to purpose was carved even before I could properly spell purpose as a child when I quit school at the age of 5.

Knowing school wasn’t for me was a affirmation that I needed to pay attention to every single thing I am going to do because it is going to be different. Do you have to be different to become consciously aware of your purpose? No. It’s a great thing that we’re all born different, saves us a lot of time!

Most people are afraid, afraid to speak their minds simply because it’s different to popular opinion.

Not going to school gave me the luxury of experimenting, spending more than eight hours of the day exploring what I’m passionate about or rather, what gets me excited. Of course I wasn’t left off the hook by my parents, so I had to learn grade 10 textbooks without learning anything formally even once. This was one of the defining moments for my purpose; I never quit education and I wasn’t about to start now. Taking this exam and applying to college really made me question what my purpose was in order to determine which course to take up.

When you’re committed to plan A you no longer need a plan B.”

Shannon Hernandez joins me on the podcast today to share her story of transforming education. Shannon is a former teacher of 15 years who wrote an expose’ about her trials as a teacher and has gone on to create The Writing Whisperer and the Transforming Public Education Podcast.

She’s an education reform activist who follows the yogic lifestyle, dives into vegetarian and vegan cooking, and often writes for The Huffington Post about the healing power of journaling, and the importance of self-care and self-reflection. 

We dive deep into her story of reinventing herself and the three key decisions she made before taking the leap into entrepreneurship. 

Screen Shot 2015-05-01 at 9.33.03 PM

On this Coffee Chat:

  • Why Shannon left her job as a public school teacher and reinvented herself
  • Smart content marketing
  • Thinking long-term and making decisions short-term
  • What to do when when you have a bad boss
  • Building a freelancing portfolio


(Psst: Email me a screenshot of you leaving an iTunes review of the podcast and I’ll send you a copy of Michael’s book. Ends June 1st)

P.S. Are you on the mailing list

CTA 650