Being nice at all costs will do nothing but leave you with resentment at the end of the day, which is why today’s guest advocates for practical optimism and kind candor instead. In this inspiring episode of Betting on Yourself, we are joined by the inimitable Gary Vaynerchuk, a born entrepreneur, chairman of VaynerX, and CEO of VaynerMedia. Gary fills us in on his entrepreneurship journey, starting at the ripe age of six, and explains how betting on himself from a young age has continued to pay off throughout his life. We discover how he decides where to place his bets, how he handles criticism, and why he chooses to live his life in the “purple.” Gary also shares his take on the fine line between optimism and delusion and why he feels it’s dangerous to coddle your kids. Tune in to hear all this and more, including Gary’s top tips for creating authentic content and comporting yourself with kind candor!

Key Points From This Episode:

• What “betting on yourself” means to Gary Vaynerchuk.
• How betting on himself from a young age has paid off.
• Examples of how trusting his intuition has served him.
• How he draws on history to make decisions about where he places his bets.
• Why Gary considers NFTs to be a profound technology.
• How he handles criticism.
• Gary shares his most significant moments of betting on himself.
• His courage to be misunderstood and take judgment in his stride.
• Why he lives his life in the purple, politically speaking.
• The danger of over-coddling your kids.
• The fine line between optimism and delusion.
• The gift of parenting with practical optimism.
• Gary’s tips for creating authentic content.
• What success means to him at this stage of his life and career.
• The dangers of being nice at all costs.
• The value of kind candor.

Links Mentioned in Today’s Episode:

Gary Vaynerchuk
Gary Vaynerchuk on LinkedIn
Gary Vaynerchuk on Twitter
Gary Vaynerchuk on Instagram
VaynerX
Michael Redd
22 Ventures

Betting on yourself takes courage and you might not always win, but if you take the losses and try to persevere, the wins will be so much sweeter. Today’s guest has truly gone through it all regarding founding startups and is refreshingly honest about the challenges, making it his mission to help other founders navigate the tricky and mysterious terrain of startups, with a focus on self-care and cumulative success. Wil Schroter is an entrepreneur and the Founder and CEO of Startups.com. He has founded no less than seven startups and after pushing through multiple failures, he is finally at a place where he is content. Wil tells us what ‘betting on yourself’ means to him and he takes us back to a moment when he made the biggest bet on himself. We discover what gives him the impetus to create, how his difficult childhood bread a survivor’s instinct, why he believes that school is not for everybody, and how he is able to stay motivated during difficult times. In our conversation, we unravel the nuances within entrepreneurship as a glamourized profession and explore some of the common misconceptions about startups. You’ll get a better understanding of the founder/investor dynamic, why innovation in raising capital is a necessity during a recession, how the internet has changed over the past 25 years, and why self-care is essential for any entrepreneur. We end by discussing the curse of 37, what Wil is currently working on, and the advice he would give to his 16-year-old self. If you're looking for a candid account of what it’s really like to build a startup, this episode is for you!

Key Points From This Episode:

• Introducing today’s guest, the Founder, and CEO of Startups.com, Wil Schroder 
• A shoutout to Wil for helping out host launch his investment career.
• What ‘betting on yourself’ means from Wil’s perspective. 
• The moment when he took a massive bet on himself. 
• Where he got the impetus to invent and create. 
• A difficult childhood and betting on yourself as a means of survival. 
• Why Wil believes that school is not for everybody, but learning is.
• The nuances within entrepreneurship as a glamourized profession. 
• What helps our guest push through difficult times: unadulterated fear. 
• Common misconceptions around entrepreneurship.
• How he was motivated at the beginning of his entrepreneurial journey. 
• Understanding the founder/investor dynamic. 
• Why you need to be innovative in raising capital during a recession. 
• How the internet has been revolutionized in the past 25 years. 
• Wil’s initial response to the first signs of success. 
• Why self-care is important for any entrepreneur. 
• The curse of 37 and how a severe panic attack changed everything for Wil. 
• His current business with other entrepreneurs. 
• Our guest's natural affinity as a creative and his love for building.  
• The advice Wil would give to his 16-year-old self. 
• The happiness and content that Will now feels!

Links Mentioned in Today’s Episode:
Wil Schroter on Twitter
Wil Schroter on Instagram
Wil Schroter on LinkedIn
Startups.com
Startup Therapy Podcast
Founders Group on LinkedIn
Michael Redd
22 Ventures

Today is a very special episode as we welcome to the podcast NBA legend and friend of the host, Cuttino Mobley. Cuttino mentored our host during their playing days, and after giving us his definition of ‘betting on yourself,’ he talks about the responsibility of blessing others when you’ve been blessed with unique gifts and talents. He explains how the talent-filled city of Philadelphia influenced his extraordinary career and what it was like being groomed by the likes of Scottie Pippen, Hakeem Olajuwon, and Charles Barkley. Cuttino tells us about the pain he experienced not being considered in the first-round draft and the joy he felt after being picked in the second. Our guest then reveals the secrets to succeeding at such a high level, why you need to obsess over what you want to become, and how he has gone on to help other men become the best version of themselves. In a moment of vulnerability, Cuttino opens up about his premature retirement and what it has been like transitioning into The Big3. To find out more about how basketball has changed as a game, how to move past mental incarceration, and how death can unify a brotherhood, tune in now to listen to the inspirational Cuttino Mobley! 

Key Points From This Episode:

• Introducing our guest, NBA legend and friend, Cuttino Mobley.
• How Cuttino mentored and encouraged our host while they were playing in the NBA. 
• Our guest’s definition of ‘betting on yourself’.
• The responsibility to bless other people when you have unique gifts and talents. 
• Looking back at his life and the time when Cuttino took the biggest bet on himself. 
• How the talent-filled city of Philadelphia influenced his journey and career. 
• Cuttino walks us through his decision to join Rhode Island. 
• The feeling of missing out on the first-round draft and being selected in the second. 
• What it was like playing with and being mentored by Scottie Pippen, Charles Barkley, and Hakeem “Dream” Olajuwon. 
• The level of focus required to succeed at the highest level: be obedient to your discipline. 
• Obsessing over the thing you want to become and studying it.  
• The impact coach Rudy Tomjanovich had on Cuttino’s career. 
• How basketball is different now from when our guest and host played the game. 
• What it was like for our guest to sign a mega-deal after being a second-round pick. 
• Cuttino’s thoughts around his premature retirement from basketball. 
• How he transitioned into The Big3 and what he’s experienced during his involvement. 
• Kobe’s passing and how the NBA brotherhood has strengthened as a result. 
• Mental incarceration and how men need to start being okay with not being okay. 
• Why Cuttino loves fatherhood and helping men become the best version of themselves.  
• The advice he would give to his six-year-old self. 

Links Mentioned in Today’s Episode:

Cuttino Mobley on Twitter
Cuttino Mobley on Instagram
Cuttino Mobley on LinkedIn
Sean Colson on Twitter
Tyson Wheeler on Twitter
Cameron Pooler on Instagram
Alvin Williams on Twitter
Hakeem “Dream” Olajuwon on Twitter
Michael Redd
22 Ventures