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

You can't control what happens to you in life, but you can control how you choose to respond. Today, we are joined by a true American hero who knows this all too well: former US Navy SEAL Commander Dan Cnossen. Thanks to his sheer mental resilience, Dan overcame the monumental setback of losing both of his legs in combat in Afghanistan in 2009, going on to become a seven-time Paralympic medalist, a three-time Paralympian, and the Best Male Athlete of the 2018 Paralympic Games. During our conversation, Dan shares his story and highlights the critical role that goal setting has played in his life. Tuning in, you'll find out how the intensity of his Navy SEAL training taught Dan to incorporate short-term goals and keep the fire of motivation alive, as well as how it prepared him for the challenges of turning his life around post-injury. We also discuss the powerful sense of agency that comes with choosing how you respond to events beyond your control, the importance of doing what you love, and so much more! Make sure you don't miss this inspiring interview with a man who bet on himself, put in the work, and proved to all of us that anything is possible.

Key Points From This Episode:

• What it means to Dan to bet on himself: having faith in himself and trusting the process.
• The strong values and work ethic his family instilled in him from a young age.
• A reflection on what inspired Dan’s decision to serve his country as a Navy SEAL.
• Find out how goal-setting has been a source of motivation for Dan.
• Dan speaks candidly about the moment he lost both his legs to an IED in Afghanistan.
• Unpacking the grit and resilience it took for him to overcome this monumental setback.
• How pain forced him to narrow his focus, shift his perspective, and create momentum.
• The power that can come from choosing how you respond to events beyond your control.
• What drew Dan to the cross-country skiing and marksmanship of the biathlon.
• Crossovers between his Navy SEAL training and training for the Paralympics.
• Insight into the attitude that Dan adopted when he received the Purple Heart medal. 
• What’s next for Dan as he retires from the biathlon to focus on telling his story.
• The advice he would give his 16-year-old self: do what you love!

Links Mentioned in Today’s Episode:
Dan Cnossen
Dan Cnossen on LinkedIn
Michael Redd
22 Ventures

"If you don't believe in yourself, who else will?" Inspired by his hardworking single mom, Corey Avinger has been betting on himself since day one, whether in school, sports, or business. After constantly being in the minority before college, the impact that attending an HBCU (Historically Black Colleges and Universities) had on Corey drove him to found an apparel company called Support Black Colleges. The company's mission is to uplift, support, and encourage others to attend HBCUs, and in the past two years, the phrase 'support Black colleges' has been Googled more than ever before (a fact that Corey is very proud of and rightly so!). Tune in today to hear about how Corey and his company have contributed to the HBCU community and the ups and downs he has experienced along the journey to get to where he is today! 

Key Points From This Episode:

• Why we shouldn't look outside of ourselves for approval. 
• How Corey's fundraising campaign to get back into college took off. 
• Corey shares how his mom inspired him to bet on himself.
• The gift that Corey has for connecting with people. 
• Origins of Support Black Colleges, Corey's apparel company.
• Some of the goals that Corey has achieved in the past few years. 
• An example of the positive mindset with which Corey approaches a challenge.
• The importance of influencer marketing to Support Black Colleges.
• How attending Howard University (an HBCU) impacted Corey's life.
• A Google statistic that Corey is very proud of.
• The value of connecting with people face-to-face.
• Corey's definition of leadership. 
• Why entrepreneurship isn't for everyone. 
• Corey shares what keeps him motivated. 
• Advice from Corey to his 16-year-old self. 
• The importance of practicing self-care. 

Links Mentioned in Today's Episode:

Support Black Colleges
Support Black Colleges on Instagram
Corey Arvinger 
Corey Arvinger on Instagram
Teyana Taylor
Michael Redd
22 Ventures

Welcome back to Betting on Yourself! Today’s guest, Doug Ulman, who has survived cancer, not once, but three times, has used his unique experience to make a profoundly positive impact on the world by making a career out of fighting cancer. Doug is the former CEO of Livestrong, a founder of the Ulman Foundation, and the current CEO of Pelotonia. During today’s conversation, he tells his own story, inspiring listeners to believe that anything is possible. We hear about his work as a leader within Pelotonia, and the unlikely experiences he had climbing Kilimanjaro, meeting Dan Rather, and coming to understand the incredible value of self-care. Doug believes that if you don’t take care of yourself, you can’t function effectively, and you definitely can’t lead! Sometimes you learn this lesson the hard way, but it’s not selfish to take time for yourself, and if you don’t, you end up in a downward spiral.  Join us to hear more from today’s amazing guest!

Key Points From This Episode:

• An introduction to today’s guest: three-time Cancer survivor, former CEO of Livestrong, a founder of the Ulman Foundation, and the current CEO of Pelotonia, Doug Ulman. 
• What betting on yourself has meant to Doug in his life: anything is possible! 
• How being diagnosed with cancer has brought an incredible long-term benefit into his life.
• Why it is impossible not to ask the question of ‘why me?’ when you are diagnosed with cancer.
• Why it is beneficial to overcome this phase quickly: you may never know!
• The debt of gratitude he owes his parents for teaching him the values of service and gratitude.
• How having had cancer has altered his relationship with fear.
• Why the shock of being diagnosed with cancer showed him that anything is possible.
• His experience of being on a team while playing sports and how it made him an optimist.
• Choosing to be transparent with his audience as the CEO of Pelotonia.
• The platform that Pelotonia provides for people to share stories and make a difference.
• The privilege of being a leader within Pelotonia.
• His predictions for the future of nonprofits and why the separation between businesses is not sustainable.
• The importance of self-care in all the work that he is doing and how he came to realize that it isn’t selfish.
• The phrase ‘walk if you can, run if you must’ from soccer, and how it has inspired him.
• Doug shares the Dan Rather story.
• Climbing Kilimanjaro and how team spirit helps us to move forward.
• Advice he would give to himself: know that challenges you face seem much bigger at the time than before you overcome them.
• How exercise acts as a way to escape the chaos of the world for Doug.
• Where to find Doug Ulman online.

If you're a fan of the show don’t forget to follow to hear new episodes and Rate or Review us wherever you tune in!

To ask a question, read the transcript, or learn more, visit MichaelRedd.com.

Links Mentioned in Today’s Episode:

Dan Rather
Ulman Foundation
Livestrong
Pelotonia
Doug Ulman on Twitter
Michael Redd
22 Ventures

Our guest today is none other than Don Yaeger, the multiple New York Times bestselling author, inspirational keynote speaker, executive coach, and so much more! In this episode, Don shares his journey of accidentally falling into journalism and going on to work his dream job as the Associate Editor of Sports Illustrated, before making a risky career pivot at age 45. You’ll learn about the challenges of his transition, the importance of being coachable, and what makes consistency the hallmark of greatness. Don has encountered some extraordinary people in his life, and he shares his remarkable experience of being mentored by the legendary Coach John Wooden, as well as the profound advice he received from Walter Payton in the last few weeks of his life. You’ll also hear a detailed account of the time he scored on Michael Jordan, plus so much more! Make sure not to miss this inspiring conversation about curiosity, humility, legacy, and everything in between!

Key Points From This Episode:

• Don Yaeger’s approach to bettering himself through curiosity.
• His inspiring story of betting on himself and making a career pivot at age 45.
• How he accidentally fell into a career in journalism and how it shaped him as a risk-taker.
• Don’s transitional experience of stepping out of his dream job.
• The value of coaching and the importance of being coachable.
• A common trait possessed by great athletes and coaches: the ability to manage adversity.
• Don’s perspective on leadership in these tumultuous times.
• His experience of being mentored by the legendary Coach John Wooden.
• What makes consistency the hallmark of greatness.
• The challenge of building a routine in today’s world.
• Invaluable advice Don received from Walter Payton in the last few weeks of his life.
• Don’s thoughtful approach to meeting and interviewing extraordinary people.
• Don recounts the time he scored on Michael Jordan.
• What ‘legacy’ means to him, both personally and professionally.
• His advice for his 16-year-old self: slow down!

If you're a fan of the show don’t forget to follow to hear new episodes and Rate or Review us wherever you tune in!

To ask a question, read the transcript, or learn more, visit MichaelRedd.com.

Links Mentioned in Today’s Episode:
Don Yaeger
Don Yaeger on LinkedIn
Don Yaeger on Instagram
Don Yaeger on Twitter
Michael Redd
22 Ventures

Nick Potts was financially stable and working in a job that he loved when he got the itch to start his own thing. Armed with valuable experience from working in the healthcare sector and driven by his desire to have a meaningful impact on people’s lives, Nick emptied out his savings, moved into a trailer in his parent's backyard, and founded his first company, ScriptDrop. Taking the lessons that he learned from starting his first company two years ago, Nick went on to found a second startup, Gifthealth! In today’s episode, Nick explains how his two companies are transforming the healthcare industry by alleviating the pain points that prevent people from accessing the medication that they need. Nick also shares how his mindset has allowed him to get as far as he has, why fear is not a part of his vocabulary, the value that he places on building relationships, and the benefits of having “some level of almost arrogance” as an entrepreneur! 

Key Points From This Episode:

• Nick shares what it means to him to bet on himself.
• The massive bet that Nick took on himself a few years ago.
• Valuable lessons about hard work that Nick learned from his mom and dad.
• Why Nick moved from Nashville to Ohio, and the first job he got after moving.
• The necessary amount of arrogance is required to be a successful entrepreneur. 
• What excites Nick most about what he has created.
• How Nick’s experience at CoverMyMeds inspired him to found ScriptDrop.
• Lessons that Nick learned through the founding of ScriptDrop.
• Where Nick’s relationship with his co-founder began.
• The benefits of working with people who you enjoy spending time with.
• Statistics that highlight the scale of the medication distribution problem.
• The mission behind Gifthealth.
• Examples of the points of friction that prevent people from accessing the medication they need and how Gifthealth eliminates these points of friction.
• What drives Nick to do the work he does.
• Why raising funding for Gifthealth was so much easier than it was for ScriptDrop.
• How Gifthealth has grown since its founding.
• Nick’s approach to raising capital. 
• A message from Nick to his younger self.
• Plans that Nick has for the future of Gifthealth.
• How the entrepreneurial ecosystem in Columbus has evolved since Nick moved there. 

If you're a fan of the show don’t forget to follow to hear new episodes and Rate or Review us wherever you tune in!

To ask a question, read the transcript, or learn more, visit MichaelRedd.com.

Links Mentioned in Today’s Episode:

Nicholas Potts on LinkedIn
Nicholas Potts on Instagram
Gifthealth
Gifthealth on Instagram
ScriptDrop
Michael Redd
22 Ventures