Courageous Conversation

A series of new technologies, financial psychologies and philosphies, so you can get better equipped on shifting and if not transforming your relationship to money, your wealth and your worth. So what do you say? Why don't we play together? Join me live every week as we bring you The SPORT of RICH.

Courageous Conversations - Episodes

EPISODE 1 – April 17, 2020

The Courageous Conversation this week is with former NBA player, Miami Heat alumni — Robert Hite.

Having the opportunity to have played with hall of fame NBA players, and a serious injury forcing a courageous conversation, learn how Robert made the transition to life after basketball and the re-invention of who he was financially. He is currently part of the ownership group of the Big 3 League with Ice Cube and is making waves in high end residential real estate in Miami. Learn from Robert’s experience of being humble, being committed to the deal, and why progress is more important than perfection.

EPISODE 2 – April 24, 2020

Behind every great man is a great woman. This week’s guest is Elena Cardone, the wife of the creator of the 10X empire, Grant Cardone. In a candid and unapologetic conversation, Elena speaks about maintaining a child like quality that anything is possible, and maintaining the drive of grizzled vets that you are going to do something or die trying. In this interview with Richard, Elena speaks about a crucible moment she had in 2008, and how making the choice to support Grant is one of the reasons she was able to accomplish more as a woman than choosing to remain in the strong independent mindset. It’s a story explained with great passion, the importance of pivoting, creating bigger goals for yourself, and truly illuminating the importance that women play not only in their relationships with their family, but in the greater context of the world. Need an example of thinking big? See what Elena thinks is possible within the next 5 years.

EPISODE 3 – May 1, 2020

Emilie Goldblum is a retired Canadian Olympic gymnast, and she speaks this week, to the power of knowing why you do something, having a mentor, and why you should just do something even if you don’t know how when you start out. Emilie is an example of how what you experience doesn’t define who you are, and she speaks openly about her own methods for holding herself to account for what she wants to achieve. She is the loving wife of Hollywood actor Jeff Goldblum and the mother of 2 children. In a courageous conversation, learn how she is a strong support and provider of structure for the family, and some of the small things she has newfound gratefulness for during the California lockdown.

EPISODE 4 – May 8, 2020

General (Ret.) Rick Hillier was a General in the Canadian Armed Forces and worked with the UN and other international organizations. In a wonderful display of being precise and accurate, General Hillier speaks about his motivation for becoming a soldier from the ripe age of 8 years old. A student of not only military history, but of figures from the past, the General speaks to the power of learning from those who have walked the same road before you and learning from their mistakes. Directly commenting on leadership, Rick outlines the things that get in a leader’s way, as well as the direct attack he used to become a great leader. This week be inspired by stories of bravery and know that a leader has but a single mission – people.

EPISODE 5 – May 15, 2020

Today’s guest is an actress, philanthropist, and mother of 3 — Finola Hughes. A truly free-spirited artist as a poet, musician, and actress, Finola speaks candidly of how the lockdown has affected her and made her aware of areas in her life that she didn’t like — but took action to change. She explains different perspectives from dealing with a sick child, helping the hungry in the nation, pondering home dwellers versus doctors on the front line, and why this lockdown time shouldn’t be wasted or forgone without self reflection. Inside reflection, people can identify what fears they have and Finola discusses times in her life where she missed an opportunity because fear made her say no.

EPISODE 6 – May 22, 2020

If you haven’t heard of Maximillion Cooper chances are you aren’t a car person, but Max’s creative touch spans creating the Gumball 3000 Series, and designing for brands such as Kappa, Puma, Adidas, and Hublot to name a few. A down to earth fellow with a penchant for creative art, married to pop star Eve, and father to 4 children, Max is an example of not knowing how to start but choosing to be in action anyway. Max tells his story of not knowing what to do at 18 when he went to a famous fashion school in Britain, but knew he had a passion for art and for racing cars, which he eventually did for Porsche. Lean in and hear about the power of proximity, relationships, taking on new challenges, and setting goals for yourself.

EPISODE 7 – June 5, 2020

He’s got flash and pizazz and passion to light you up. The guest this week is Karl Wolf, musical artist, writer, and producer and winner of MTV awards, Junos, and the lot. In a passion filled courageous conversation, Karl speaks about his story of fleeing Lebanon during the war, finding his passion, resolving to work at his passion no matter what or how long it was viable, and persisting in the music industry even though no one cared at the start. It is an inspiring story, and Karl is a living example of how setbacks can become stepping stones, how he broke into the music industry by the power of proximity, and that your passion literally fuels you to work like a tank. An added bonus: find out what he thinks about the next lyrical movement in music against the backdrop of the US protests.

EPISODE 8 – June 12, 2020

Vinay Virmani is the guest for this week’s Courageous Conversation. He is a Canadian actor and movie producer, and the Chief Content Creator for the brand Uninterrupted, a brand made by and for athletes to empower their voice to empower others. Vinay paints an interesting perspective about diversity in the movie industry and brings forth insightful thoughts on branding and telling your story so that it is the story that gets retold in the world. Discover how vitally important a vision of the future can be when the present is tough. Get your pen ready and take notes about how the digital world is changing content and content consumption, and the importance of inspiring stories.

EPISODE 9 – June 26, 2020

Vitor Belfort is a Brazilian MMA fighter who made a huge splash onto the UFC at 19 years old knocking out Tank Abbot. He was well known as being always in the best of shape and was a champion. Fighting takes a lot of grit, and even though technology was seemingly fighting Vitor by dropping his signal, his grit and persistence and commitment to the call made his few short moments extremely impactful. Vitor was a live example of commitment driving actions. He practices what he speaks and is continually stretching himself, believes you should invest in the dreams of your family, and is crystal clear that one of the Gracie brothers was a tremendous mentor and spoke words of life and encouragement over him. One thing you can quote from Vitor, “Your dreams have to be big and your sacrifices bigger.”

EPISODE 10 – July 1, 2020

Vitor is back by popular demand and once again persevered through some initial technical difficulties. Vitor explains clearly that he knows his purpose and that it isn’t negotiable. He speaks openly about his faith based approach to intentions, actions, having righteous relationships, and doing the right thing. He is a family man and hits the nail on the head about how critical it is to choose the right spouse for you. He is unwavering in stating that the world needs leaders who live what they preach and that where the struggle is lives great victories. Pay special attention to his awareness of close relationships and being of purpose to other people. This courageous conversation is a gem.

EPISODE 11 – July 10, 2020

Today’s courageous conversation is with the man leading all things sales and marketing at Cardone – Dave Robards. It is amazing to hear the transparency with which he tells his story of moving from high school dropout to a top 1% earner. He is open about bad decisions in his past, and how being consistent and frequent in learning from Cardone U literally changed his life 7 years ago. Tune in for a passionate and entertaining story filled with struggles and victories. Learn how the 3 parts of a game work to stop you or propel you inside of the 10X ideology, and why you should view the problems that arise as a result of the game you are playing. Be ready, be inspired.

EPISODE 12 – September 11, 2020

The man and the legend of late-night talk shows, our courageous conversation today is with Larry King. Larry is 86 years old and remains witty and sharp of mind. You know what else he is? Himself, and no one else. This is a key point that King expresses, be yourself, be truthful, be humble and just do stuff because you want to not because you are worried about another person’s reaction. He is a great-grandfather and has an indominable spirit for life, proof of which is surviving many strokes and heart attacks and still working on his newest project – the Millionth Question podcast. It is a great talk, full of passion, and lots of encounters from Larry’s large library of experience.

EPISODE 13 – September 18, 2020

The courageous conversation today actually takes place twice – first with the street basketball YouTube phenom The Professor and second, with hall of fame boxing referee Joe Cortez. The Professor is bubbling with excitement for the work that he does, and his story provides a great example of noticing an opportunity back in 2006 on YouTube, finding people who can help him understand social media, and being intentional in using it to grow his brand. What is one of The Professor’s key messages? Be very active and keep it simple to start.

The second guest is Joe Cortez, a hall of fame referee who has been in the ring for 176 championship bouts. He is full of gusto and is an uplifting spirit. In this conversation, his experience being around champions will illuminate why you need grit, why you need a plan to stick to, and why you must prepare for the unexpected. Put your seat belts on and get ready to move fast.

EPISODE 14 – October 2, 2020

The conversation today is full of courage. The guest is David Falk, agent to the stars and top athletes, and the first agent to negotiate a $100M in the NBA. He is a first generation American of Polish heritage, and he speaks of himself as always wanting to lift the standard. David speaks to his first agency job with no pay, and when he started earning a little, he still had 2 jobs but high job satisfaction. These are just a part of David’s story which took root at 12yrs old when he knew he wanted to be a lawyer and had a passion for sports. He shares a lot of his experiences for you to learn from, touching on subjects such as mentors, networking, ethics, passion, and how being forthcoming of his intentions helped him sell his business FAME, for $200M.

EPISODE 15 – October 9, 2020

He’s made you tear up from laughter, and he can play dramatic roles too. Today’s guest was in the Scary Movie franchise and White Chicks - it is Marlon Wayans. He is a lot more than that as you will hear in this courageous conversation. Mindset. Hard work. Graciousness. Getting up after getting knocked down. Leaving a legacy. A father with a commitment to being a role model for his children and all the youth he speaks to, acknowledging the importance of mentorship, the gravity of a strong family unit, Marlon’s story of emerging from the projects of NYC to a sought-after Hollywood star is filled with gold nuggets.

EPISODE 16 – October 16, 2020

This man needs no introduction – he is the former heavyweight champion of the world – Mike Tyson. As you watch this conversation with Iron Mike, keep in mind the teachable lesson that Richard puts forth as the primer, the Tyson code he calls C4 – Courage, Clarity, Chaos, and Consistency. Listen to the honest and humble Mike Tyson speak of the importance that Cus played as a mentor in his success, why consistency plays such a crucial role, and how he learned to control his ego. Mike remains inspired, is jumping back in the ring to fight Roy Jones Jr, remains a student of life, is facing fear head on, and is trying to be a good role model. It is a great talk.

EPISODE 17 – October 23, 2020

We have a double feature for you today. Two gentlemen from humble beginnings who understand what it means to struggle, worry about the next meal, persevering, and being amazing performers. Today the courageous conversations are with Isaac Calpito (aka. Isaac Boots) and the Human Highlight Reel former NBA superstar Dominique Wilkins. Isaac is the creator of the Torch fitness movement and he talks about knowing his passion at 18 years old and leaving the day after high school graduation for NYC not knowing what to do but willing to work hard. Learn how Isaac is giving back, engages and cares about all the people he encounters, and using technology to run his businesses.

Dominque Wilkins earned his nickname at 17 but it stuck, and now he is releasing a movie about the making of who he is as a man. He was raised by a single mother of 8, was the man of the house at 12, and left home at 16. His story is inspiring and the grace and certainty he speaks with is on full display. He was strong for his family, a giver throughout his life, and remains involved in charitable endeavors. If there were qualities the greats encompassed they are, never quit, and believe in yourself even when no one else does. A bonus: check out what he thinks is a terrible quality of the new generation of players.

EPISODE 18 – October 30, 2020

Today’s guest is the Founder and CEO of BRON Studios, which produced the hit movie Joker, - Canadian businessman Aaron Gilbert. An intense but laid-back speaker, Aaron talks about how he got into the arts from a young age. On top of that, Aaron was building and trading stuff as a kid which is surely a precursor to his entrepreneurial spirit. Inside the movie industry, he speaks about the problem he saw and how he fixed it, which is how he founded BRON with his wife. His story will highlight key principles of saying yes to opportunity and figuring it out along the way. Challenges abound in producing movies and attracting content, talent, and money and Aaron highlights the advantages of being consistent and being clear as necessary qualities to solve problems.

EPISODE 19 – November 6, 2020

TheArsenale is a unique and powerful brand of high end and creative stuff, and the mastermind behind it is here for a courageous conversation – Patrice Meignan. He loves cars, art, and futuristic things, and he has found a way to commercialize his passion, so much so, that companies call him to reengineer their most prized brands. Pat is prepared, he loves his craft, and is a big believer that you should have big dreams and not be shy about sharing them, in fact you should be selling them. Pat exemplifies having strong commitment, faith in himself, what its like to literally work from 0, and the benefits of having a connection to history and heroes. A man of the present and future, learn how Instagram has helped him attract enormous business.

EPISODE 20 – November 13, 2020

If you have ever wondered if you could make your brain work better, then today’s conversation is for you. Jim Kwik is the author of the book Limitless, and he tells a heartfelt story about his journey from 3 severe brain injuries before age 12, to taking care of his aunt who developed Alzheimer’s, to currently being a teacher in demand of how to make your brain learn more, better and faster. You are going to ascertain what it means to face fear head on, using your fears as rocket fuel, and how we can truly change how we think. Tune in and see what Jim ponders is possible to better ourselves, our minds, and our school systems. As he so aptly says, “we learn to earn to make a return.”

EPISODE 21 – November 20, 2020

You are in for a treat today! NBA all star, slam dunk champ, and recently crowned NBA Champion Dwight Howard of the L.A. Lakers is our special guest. This is a heartfelt and courageous conversation with Dwight whose experiences will highlight for you some spectacular ups and downs – things you will not hear anywhere else. At 15 he learned how quickly life can change from up to down. Vicariously get a sense of how bad things got for Howard when he couldn’t eat sitting up or tie his shoes before a game. Notice the difference in his career from when his ego went from being the boss to being controlled. Best of all, immerse yourself in how Dwight turned his life around by turning to his faith in God, and how giving himself up to be in service to others, he gained his life back, his family, and achieved his ultimate athletic goal – the NBA Championship.

EPISODE 22 – December 18, 2020

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EPISODE 23 – January 22, 2021 (Season 3)

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EPISODE 24 – January 29, 2021

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Richard Dolan

Instructor / Facilitator

WEALTH MANAGEMENT, MERCHANT BANKING BEGINNINGS & EXPERTISE Starting in the wealth management industry in 1992, Richard started his career as a cold call cowboy making three hundred cold calls a day every day for a Bay Street firm. Following a ten-year record of raising over $3B in assets, Richard was invited to design and deliver a certificate program at Schulich School of Business (Executive Development Centre) York University on the subject of marketing and selling wealth management services. To date Richard has raised over $7B in assets worldwide and coached hundreds of financial advisors, wealther managers and family offices.