Randall Kaplan is joined by serial entrepreneur and media personality Kevin O’Leary.  Known to many as Mr. Wonderful on SharkTank, Kevin talks about how his unique life experiences made him the successful entrepreneur and investor he is today. 

In this episode, Kevin and Randall talk about Kevin’s upbringing and what Kevin learned from his mother about financial independence and investing.  Kevin shares stories about the moment he knew he needed to work for himself, the greatest lesson he learned in business school, and his first entrepreneurial success.  Kevin also talks about why culture matters in business, entrepreneurship and investment strategy, and much more. 

Topics Include: 

• Growing up with an alcoholic father.
• How Kevin’s childhood experience informed how he thinks about investing.  
• When he decided to become an entrepreneur.  
• His first success as an entrepreneur.  
• Overcoming dyslexia and education.  
• Investment strategy and entrepreneurship.  
• The war of business.  
• What he learned as an intern at Nabisco.  
• Women in finance and investment.  
• Cryptocurrency, decentralized finance, and NFTs.  
• The value of failing as an entrepreneur.  
• And other topics...

Kevin O’Leary is a serial entrepreneur, best-selling author, and investor.  Kevin was a co-founder of Softkey Software Products (later The Learning Company) which Mattel bought for $4.2 billion1999.  Today he leads the O’Leary Financial Group, including O’Leary Funds, O’Shares EFTs, O’Leary Publishing, and O’Leary Ventures.  He is also the founder and Chief Sommelier of O’Leary Fine Wines. Kevin is fondly known as “Mr. Wonderful” on ABC’s Shark Tank, is the host of the CNBC show Money Court, and is also a host and personality on Discovery’s Project Earth and CBC’s Dragons’ Den.  Kevin’s is also the author of three best-selling books about financial literacy.

Resources Mentioned:
nft.com

Coaching and Staying Connected:

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You probably know Chris Voss as the FBI Hostage Negotiator that wrote the best-selling book Never Split the Difference.

What you probably don’t know about Chris is that he grew up an average kid in the Midwest.  There was nothing extraordinary about him, he claims.  He wasn’t popular, academically gifted, or notably athletic.

But there is one thing that sets Chris apart from the rest, and he is well aware of what it is – a commitment to getting better every day.

No matter where you are in life, Chris has tools to help you unlock your potential.

In this episode, Randall Kaplan and Chris Voss talk about reframing setbacks as setups that lead to something better.  They discuss the two caveats for taking advice from someone, the three techniques to a safe resolution, and the exponential benefits of incremental improvement.  Chris shares how his experience in hostage negotiation has transferred to business and provides actionable techniques for negotiating in both our personal and professional lives.

Topics Include:

• Post-traumatic growth.
• Victim mentality and bullies.
• Negligible shifts that can result in major differences in outcome.
• The “win or learn” mindset.
• Ways to unofficially recruit a mentor.
• Mirroring, labeling, and delivery in negotiations.
• Lessons from hostage negotiation that taught Chris about preparation and making mistakes.
• The art of listening.
• The ability to say no and protect your time.
• The value of kindness.
• The ways to lead a team.
• The most valuable investment you can make.
• And other topics...

Chris Voss spent 24 years working for the FBI in their crisis negotiation unit.  He was the FBI's chief international hostage and kidnapping negotiator where worked on more than 150 cases, including the 1993 world trade bombing and the 1996 TWA flight 800 explosion.  He is the recipient of the Attorney General's Award for Excellence in Law Enforcement and the FBI Agents Association Award for Distinguished and Exemplary Service.  Today, he is an adjunct professor at Georgetown University School of Business and a lecturer at USC Marshall School of Business.  He's the CEO of the Black Swan Group, which provides training, negotiation, and leadership skills for executives. He is also the author of the bestselling book Never Split the Difference: Negotiating as if Your Life Depended on It.

Resources Mentioned:
Chris’ Website
Sign Up For Chris’ Weekly Newsletter
Book: Never Split the Difference by Chris Voss
Beyond Board Website
Sarah Zapp’s Website

Coaching and Staying Connected:

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Randall Kaplan is joined by professional NHL hockey player and Olympic athlete Bobby Ryan. They discuss how, at age 10, Bobby and his family lived in hiding under an assumed name for years after his father tried to murder his mother and escaped bail, Bobby’s rise to becoming an NHL All-Star, his battle with alcoholism, his views on why you need to eliminate the takers in your life, and much more.

Topics Include:
Separating great athletes from elite athletes.  Excelling at hockey from an early age.  Going 39-0 with the LA Kings junior team.  Winning a national championship at age 12. Being drafted as the second overall pick in the NHL as an eighteen-year-old.  Shifting goals and priorities with age.  Learning about work ethic and dedication from his parents.  Asking for help when you can’t stop drinking.  Making a comeback and being a leader.  And other topics...

Bobby Ryan is a professional NHL hockey player who has played for the Anaheim Ducks, Ottawa Senators, and Detroit Red Wings.  He began his hockey career on the Los Angeles Kings junior team, winning a national championship at age 12.  Bobby has also represented the United States in international and Olympic hockey, winning a silver medal in the 2010 Winter Olympics.  After taking a leave for substance abuse in 2020, Bobby was awarded the Bill Masterton Memorial Trophy, an annual award to the NHL player who best exemplifies the qualities of perseverance, sportsmanship, and dedication to ice hockey.

Coaching and Staying Connected:

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Randall Kaplan is joined by Ben Sherwood to discuss what is missing from the conversations and books on excellence. They discuss pursuing your dreams when the odds are overwhelmingly against you, the murder of journalist David Kaplan while Ben was sitting next to him in a car during the Bosnia-Herzegovina conflict, canceling the hit sitcom Roseanne in 2018 when he was in charge of ABC Television, moving from coast to coast several times to pursue professional opportunities balances against personal and family needs, and much more.

Topics include:
Explaining why love is the greatest motivator. Learning guiding principles for making career decisions. Becoming a Rhode Scholar.  Admiring Robert Iger, former long-time CEO of Disney.  Starting Mojo, Ben’s newest business venture. Learning the significance of patience and self-forgiveness in our pursuit of excellence.  Explaining the value of kindness and generosity.  Understanding the meaning of what it means to live your deepest questions in life. And other topics…

Ben Sherwood is an award-winning journalist, the former executive producer of Good Morning America, the former president of ABC News and CEO of Disney-ABC Television Group, and the former Co-Chair Hulu. He is also the author of four best-selling novels and a non-fiction book titled The Survivors Club: The Secrets and Science That Could Save Your Life.  Ben is also the founder of MOJO, a coaching app for parents designed to revitalize youth sports.

Coaching and Staying Connected:

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Randall Kaplan is joined by award-winning journalist Lara Logan to discuss the crisis in Afghanistan, the importance of critical thinking, the pursuit of truth in the age of misinformation, the courage to speak your mind even when it’s unpopular, the fear of reporting from dangerous war zones in times of conflict in locations around the world, the experience of being a sexual assault and rape victim, today’s current events which she calls the “fight of our lifetime,” and much more.

Topics Include:
Lara’s early life growing up in apartheid South Africa.  Providing her thoughts on the presentation of opinion as fact and how it is killing American media and sowing division. Sneaking into Afghanistan and Egypt during extremely dangerous circumstances when her boss refused to “send Barbie to war.”  Experiencing a brutal attack and rape and what it taught Lara about life, death, personal choice, and integrity.  Fighting and beating breast cancer.  Making mistakes as a journalist, the importance of saying your sorry when you’re wrong, and the consequences from reporting errors regarding the Benghazi attack. Defining success in her life today.  Discussing what Lara would do if she were was the President of the United States.  And other topics...

Lara Logan is an award-winning journalist who has been reporting from war zones around the world for more than twenty years. She has covered stories during times of conflict in Afghanistan, Iraq, Egypt, Kenya, Liberia, and many other countries. She spent 16 years at CBS news serving in a variety of roles including Chief Foreign Affairs Correspondent and a 60 Minutes Correspondent.  Lara has been the recipient of many awards for her journalism including three Emmy Awards, two Edward R Murrow Awards, and the prestigious Daniel Pearl Award for Outstanding International Investigative Reporting. Lara has spent more time reporting in Afghanistan during the last twenty years than all but a few reporters. She is currently the host of Lara Logan Has No Agenda for Fox Nation.

Coaching and Staying Connected:

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Randall Kaplan is joined by Strauss Zelnick to discuss his role as an executive leader in the world of entertainment and media. They discuss what to prioritize when starting a new career, sacrificing security to pursue your dreams, the value of work ethic and grit in the marketplace, and much more.

Topics Include:
Why your salary shouldn’t be your top priority when starting a new career. The detriments of modern helicopter parenting. Cultivating the skill of deep listening. The significance of earning money early in life. Why Strauss chose to pursue a business degree when breaking into the world of entertainment. Gracing the cover of Men’s Health Magazine at age 61. Prioritizing healthspan. Using fitness to build relationships. And other topics...

Strauss Zelnick is an American businessman and entrepreneur. He is the former VP of Colombia Pictures, one of the largest film production companies in the world, and the former chairman of media conglomerate CBS Corporation. Strauss is the founder, chief executive officer (CEO), and managing partner at ZMC (ZelnickMedia Corporation), a private equity firm managing roughly $775 million. Strauss is also the Chairman and CEO of Take-Two Interactive, a video game holding company based in New York City.

Coaching and Staying Connected:

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Randall Kaplan is joined by Anthony Scaramucci to discuss rising through the ranks of global finance as a blue-collar kid from Long Island, balancing the pursuit of our dreams with our personal obligations, what he learned from his 11-day stint as the White House Communications Director for President Trump in July 2017, and much more.

Topics Include:
Growing up in a blue-collar family. Anthony’s early jobs and entrepreneurial aspirations. Failing the Bar Exam.  Lessons learned from being hired and fired at Goldman Sachs.  Anthony’s involvement in NY politics.  The importance of growing your network.  Public speaking and performances.  Getting clear on what it means to pursue excellence in your life.  Philanthropy, and other topics.

Anthony Scaramucci is the founder and co-managing partner of SkyBridge Capital, an investment firm that manages over $10 billion.  He is the founder of the prestigious SALT Conference, a global thought leadership and networking forum encompassing finance, technology, and geopolitics.  In 2016, he was ranked number 85 in Worth Magazine's Power 100, a list of the most powerful people in global finance.  Anthony is a member of the Council on Foreign Relations (CFR), Vice-Chair of the Kennedy Center Corporate Fund Board, a board member of the Business Executives for National Security (BENS), and a Trustee of the United States Olympic & Paralympic Foundation.

Coaching and Staying Connected:

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What does it take to become one of the most iconic and successful venture capitalists of all time?  How does a commitment to freedom and trust empower us to think big and drive progress?
 
Meet Tim Draper.  An early investor in Hotmail, Skype, Tesla, Space X, Twitter, Robinhood, Coinbase, and other industry-disrupting companies, Tim began his venture capital journey at age 27 and never looked back. In this episode, Tim breaks down for listeners why thinking for yourself will be the most valuable skill in the 21st century, how cryptocurrency could forever change the economy as we know it, what selling condoms can teach us about running a business, and much more.

Topic Include:
The impending automation revolution, and how to prepare for it.  What selling apples as a kid taught Draper about politics. The importance of heroes and superhero figures.  The unique curriculum of Draper University.  Cryptocurrencies and the future of bitcoin.  The art of cold calling, and the ability to close.  Working with Elon Musk.  The value of mentorship, and other topics.

Tim Draper is a true visionary.  A third-generation venture capitalist, Tim is one of the most successful venture capitalists of all time.  In 1999, Tim created the first Silicon Valley venture capital firm to raise a global venture capital fund.  He was an early investor in bitcoin and has been among its greatest proponents since 2010.  He is the author of How To Be The Startup Hero: A Guide and Textbook for Entrepreneurs and Aspiring Entrepreneurs.  Tim is also the founder of Draper University whose mission is to ignite the entrepreneurial spirit of students from around the world and prepare them for success in the real world.

Resources Mentioned:
How To Be The Startup Hero, by Tim Draper
Draper University

Coaching and Staying Connected:

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Randall Kaplan is joined by Brad Keywell to discuss what it takes to achieve excellence at the highest level as an entrepreneur.  In this episode, Brad shares with listeners how to out-work and out-hustle the competition, why he channels his entrepreneurial drive into disrupting industries, how he grew Groupon from 124 employees to 5,100 employees in a single calendar year, and much more.

Topics Include:
Brad’s five keys to success.  Brad’s early business ventures, including a greeting card business he started at age six.  The power of preparation.  Brad’s mentorship under Sam Zell.  The lasting influence of loving, supportive parents.  Tangible versus intangible skills.  Fundamental truths about parenting.  Working with the energy of fear.  Choosing business ventures as an entrepreneur.  Overcoming early failures.  Focusing on what you can control.  Balancing individual needs and collective needs.  Mental health, self-care, philanthropy, and other topics.

Brad Keywell is an incredible entrepreneur who has co-founded a variety of companies including Echo Global Logistics, Enterprise Transportation, Uptake, and most famously Groupon.  He is currently the CEO at Uptake, which reached the $2 billion valuation faster than any other tech company in history - and was a Co-Founder of Groupon, which at the time reached the $1 billion valuation faster than any other company in history.  In 2019, Brad received the Ernst & Young World Entrepreneur of the Year Award, becoming one of only three American winners in the award’s 21-year history.  He is the co-founder of Lightbank, a venture capital firm with $360 million under management that specializes in making venture capital investments in "disruptive" technology companies in the United States.  Brad is also the founder of Chicago Ideas Week, a week-long conference bringing together thought leaders and innovators from around the world to speak on a variety of topics - and he has also signed The Giving Pledge, promising to give away at least half of his wealth to charitable causes.

Coaching and Staying Connected:

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Randall Kaplan is joined by global superstar Sharon Stone to discuss what it took for her to achieve excellence in Hollywood as an outsider, how she managed to claw her way back from a crippling brain aneurysm, why being of service goes hand-in-hand with pursuing excellence, and much more.
 
Topics Include:
Growing up dirt poor.  Sharon’s early jobs and experiences as a model.  Challenges as a woman and an outsider in Hollywood.  The need to constantly prove yourself as a woman.  Setting clear goals and pursuing dreams.  The primacy of professionalism and kindness.  The challenges of being a global superstar.  The prevalence of sexual assault in the US.  Finding ways to be of service every day.  Sharon’s charity and philanthropic work.  And other topics.

Sharon Stone achieved global superstardom for her performance in the blockbuster film Basic Instinct and has appeared in over fifty-two movies.  She has won 43 awards for her acting including a Golden Globe for Best Actress in a Motion Picture and an Academy Award nomination for the film Casino.  Sharon is intimately involved in humanitarian and philanthropic efforts, and received the Nobel Peace Summit Award in 2013.  In March of 2021, Sharon released The Beauty of Living Twice, an autobiography that details her life and the incredible challenges she’s managed to overcome.

Resources Mentioned:
The Beauty of Living Twice by Sharon Stone
Teenline, emotional support line for youth – 1.800.852.8336
Hotline for victims of domestic abuse – 1.800.799.SAFE (7233)
Homeless Not Toothless
Planet Hope

Coaching and Staying Connected:

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