Betting On Yourself

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: 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: 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: 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: 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: 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: 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: 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: 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

Joining us in conversation today is Lacey Picazo, award-winning creative and Founder of ZoCo Design. In this episode, Lacey fills us in on why we need to set our own table and approach entrepreneurship with humility. We discuss the implications of planning too far ahead and touch on how to manage fear when building a business. Lacey also guides us through the practical aspects of hiring and prioritizing culture, while balancing work life with home life. Lacey is someone who truly understands the human aspect of both design and business, with a focus on user experience, and who has a refreshing openness about challenges and values. If you’re wondering how to maintain valuable connections with both clients and employees while prioritizing what’s meaningful to you and avoiding overworking, this episode is for you. Key Points From This Episode: 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: ZoCo Design Lacey Picazo on Instagram Lacey Picazo on Twitter Lacey Picazo on LinkedIn Michael Redd 22 Ventures

Traditional capitalism forgets an important variable: happiness. Today's guest believes that the true purpose of business is to uplift the experience of existing, not to make owners wealthier or produce ever-cheaper goods and services, but to elevate others to elevate himself. Tuning in, you'll hear from entrepreneur, speaker, and bestselling author, David Meltzer about his life's mission to empower over one billion people to be happy! David is the co-founder of Sports 1 Marketing and formerly served as CEO of the renowned Leigh Steinberg Sports and Entertainment agency, which was the inspiration behind the movie Jerry Maguire. His simple yet powerful mission has led him on an incredible journey to provide one thing: value, and in all of his content and communication, that is precisely what you'll find! His books, Compassionate Capitalism, Connected to Goodness, and Game-Time Decision Making, blend spirituality with business insight to offer practical advice and helpful guidance for today's entrepreneurs. In this episode, we delve into David's extraordinary career and how his upbringing shaped his trajectory and outlook on life. He describes how adopting an abundance mindset has helped him contribute to society by sharing his wealth and success and how he learned the value of going the extra mile every day and what it takes to be a servant leader. If you're ready to uncover your potential and learn how to bet on yourself, this episode is for you! We hope you'll join us. Key Points From This Episode: 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: David Meltzer David Meltzer Email David Meltzer on Twitter David Meltzer on LinkedIn David Meltzer on Instagram Compassionate Capitalism Connected to Greatness

The road to success in the world of entrepreneurship is not easy, and it is definitely not clear. It takes a strong determination and commitment to your goals to navigate the unknown territories we will encounter along the way. Today, our guest is such a great example of this kind of bravery and self-belief. David Shands is an author, speaker, community builder, and the man behind the incredibly popular Social Proof podcast! We had a great conversation today, unpacking David's attitude towards business, the emphasis he puts on achieving goals constantly, the role of his faith, and how he suggests people get over their fear of failure. David shares so much wisdom, touching on the process of evaluation, the constant rise of podcasting, and much more, so make sure to join us today! Key Points From This Episode: 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: David Shands on Instagram Social Proof Podcast Sleep Is 4 Suckers David Shands on Twitter LeBron James Los Angeles Lakers Golden State Warriors The Cheesecake Factory Michael Redd 22 Ventures

It can be tricky knowing when to bet on yourself, especially if you're at the start of a successful career and feel an inner calling to change course drastically. No one knows this better than today's guest Jason Y. Lee. Jason is the founder of Jubilee Media, a company that creates original videos about meaningful human experiences and strives to create a movement of young changemakers through radical empathy. When Jason decided to pursue content creation full-time, he worked at a prestigious consulting firm and earned a six-figure salary. It took a lot of courage to leave all that behind when YouTube was only starting as a platform. In our conversation, Jason talks about how he made the difficult decision to bet on himself, what motivated him, and why his definition of success is by making a positive impact. He describes how being the son of immigrant parents shaped his worldview, hopes that their children would follow a more conventional path, and why their decision to come to America is a crucial example of betting on yourself. Tuning in, you'll hear Jason break down how he founded Jubilee Media, the intense soul searching that preceded it, and the vital role his wife played in its growth and success. By betting on himself, Jason has built an incredible business, connecting people when our political divisions are at a historic high. We hope you'll join us for this inspiring conversation full of valuable insights and radical honesty! Key Points From This Episode: 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: Jason Y. Lee on LinkedIn Jubilee Media Jubilee Media on LinkedIn Jubilee Media on Instagram Michael Redd 22 Ventures

Today's episode is all about how coming together can create a rising tide for everyone, and building bonds that can support us all as we move forward through the uncertainties of life and business. Joining Michael on the show today is Tom Krouse, the CEO of Donatos, and Ron Jordan, the CEO and Chairman of Jordan Hospitality Group! We get to talk about the special partnership between today's panel, and why it goes beyond the simple definition, to something more like family. The conversation covers a great deal of ground with these two inspiring individuals, touching on the importance of culture and a nurturing environment, our guest's histories, professional challenges in the last couple of years, as well as their aspirations going forward with their partnership. The theme of community is a recurring one, with both Tom and Ron touching on how important it has been to them and their development over their careers. We also talk a little about the ethos at Donatos and how innovation and consistency have driven their Founder, Jim Grote to establish such a strong brand. To hear it all, and take part in a fabulous conversation with Ron and Tom, be sure to press play! Key Points From This Episode: 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: Ron Jordan on LinkedIn Tom Krouse on LinkedIn Donatos Jordan Hospitality Group Donatos on Instagram Jim Grote Alex Shumate Grote Company Sonoma Flatbreads Red Robin Michael Redd 22 Ventures

Title: Coach Scoonie Penn: How to Walk Into the Unknown (and Win) Artist: Michael Redd Scoonie Penn, former college and professional basketball player, Director of Player Development at the Ohio State University, and Assistant Coach for the NBA’s Memphis Grizzlies, joins Michael on the podcast today. “People will tell you that you’re not capable, or that it’s not going to work, but you need to believe in your own strengths and abilities. I love betting on myself.” - Coach Scoonie Penn They discussed Scoonie’s long and successful career in basketball, walking into the unknown, how he grew up at a young age, going to the NCAA Final Four, the NBA Draft and playing in Europe, and his natural talent for leadership. As you’ll hear, Coach Penn is a fearless, hilarious, and Godly man. His version of betting on himself has always been about going all in, taking extreme responsibility, and being able to look at himself in the mirror at the end of each day. In this episode Michael and Coach Penn talked about: 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. Resources: Coach Penn on InstagramMichael Redd on Instagram

Title: Thaddeus Young: Doing Whatever it Takes Artist: Michael Redd Thaddeus Young is a legendary Georgia Tech Alum, Power Forward for the San Antonio Spurs, accomplished entrepreneur, and founder of the Young for Youth foundation, joins Michael on the podcast today. “There’s no running, there’s no hiding, I’m doing whatever it takes.” - Thaddeus Young They discussed Thad’s career as a professional athlete in the NBA, his tough childhood growing up in Memphis, the influence of his extraordinary mother, his incredible longevity at the pinnacle of athletic competition, and his remarkable success as an entrepreneur. Thad is a talented, even-keeled, relentless, and humble man of faith. He’s also a guy with a BIG heart. You can hear it in his voice, how grateful he is for his life, his family, and his friends. In this episode Michael and Thaddeus Young talked about: 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. Resources: Thaddeus Young on InstagramMichael Redd on Instagram

Title: T.J. Ford: The Willingness to Risk Everything Artist: Michael Redd T.J. Ford, former NBA point guard, founder of the T.J. Ford Academy, and -- most importantly -- my former Bucks teammate, joins Michael on the podcast today. “You need to be willing to risk everything if you want to be the best in the world.” - T.J. Ford They discussed T.J.’s career and mindset as a professional athlete, his origins playing 3-on-3 in the early years, his first “break” as a player, his incredible high school years, the long road to the NBA, and his inspiring post-retirement work with the T.J. Ford Academy. As you’ll hear, T.J. is a very cool, courageous, and Godly man. His version of betting on himself was always about doing everything he could to take care of his family, even in the face of serious physical challenges. In this episode Michael and T.J. talked about: What betting on yourself means to himWhat it meant coming from a basketball familyWho inspired him as a young manHis two high school championshipsHis early struggle with spinal stenosisThe importance of making bold decisionsHis viral moment, before viral moments existedHow he approached the NBA as an underdogThe mindset of the epic comebackHow he thinks he’d fare in today’s NBA gameThe story of the T.J. Ford AcademyThe advice he’d give his sixteen-year-old self 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. Resources: T.J. Ford on InstagramMichael Redd on Instagram

Title: Tzvi Twersky: If You Don’t Bet On Yourself, Who Will? Artist: Michael Redd Tzvi Twersky, legendary marketer in the sports world and now sports marketing lead at Tik Tok, joins Michael on the podcast today. “If you don’t bet on yourself, who will?” - Tzvi Twersky They discussed Tzvi’s incredible career as a writer, editor, publisher and world class marketer, how he started from nothing, his close working and personal relationship with Kobe Bryant, our take on winning an NBA championship vs. playing on the US Olympic Team, and the love of our true national game: basketball. Tzvi is an insanely creative, talented, and driven man. He’s also a man of amazing spirit. He’s one of those people that others respect AND love, which is a rare combination in the brutal world of business. In this episode Michael and Tzvi Twersky talked about: 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. Resources: Tzvi Twersky on InstagramMichael Redd on Instagram

Title: Iyin Aboyeji: The Challenges are Always The Opportunities Artist: Michael Redd Iyin Aboyeji, named one of the Top 100 most influential Africans by New African magazine, and co-founder of Andela, Flutterwave, and Future Africa, joins Michael on the podcast today. “The challenges are always and forever the opportunities.” - Iyin Aboyeji They discussed Iyin’s decision to commit his talents and career to the future of Africa instead of Silicon Valley, honing his professional goals, his incredible startup success, building the first “unicorn” company on the African continent, and his childhood growing up as a Pastor’s kid. Iyin is a man of true and deep faith, and one who is extremely accomplished in business. His transformative vision for the future of Africa is incredibly inspiring and completely practical. This is a special episode of the podcast. In this episode Michael and Iyin Aboyeji talked about: 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. Resources: Iyin Aboyeji on TwitterMichael Redd on Instagram

Title: Coach Chris Holtmann: Choose to Challenge Yourself Artist: Michael Redd Chris Holtmann, Head men’s Basketball coach at The Ohio State University and former All-American basketball player at Taylor University, joins Michael on the podcast today. “I have not been afraid to take risks.” - Coach Chris Holtmann They discussed Coach Holtmann’s lifetime decision to always challenge himself and avoid comfort, the importance of great mentors, the unbelievable faith and grit of his wife, and his unorthodox path to becoming a world-class basketball coach. Chris is a humble, intelligent, and extremely accomplished man who has taken interesting and unconventional risks his entire life. His story can help us all to remember that our futures are in God’s hands, we only need to do our very best every day, then leave the rest to Him. In this episode Michael and Coach Holtmann talked about: What betting on yourself means to himWhy he’s never been afraid of riskHow his family has impacted his life choicesHis greatest professional influencesThe importance of service and humilityWhy no task is beneath the truly greatWhy he took a “step back” in order to go forwardYour responsibility is consistent and daily workThe reality of seeking out a major coaching jobThe days of “transactional coaching” are overThe advice he’d give his sixteen-year-old self 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. Resources: Coach Holtmann on TwitterMichael Redd on Instagram

Title: Kevin Poston: Don’t Cheat Yourself Artist: Michael Redd Kevin Poston, legendary sports agent for over 30 years, sports marketing expert, named by Sports Illustrated as one of the most influential minorities in sports, and Michael’s beloved agent during his time in the NBA, joins Michael on the podcast today. “My father was the greatest man I’ve ever met. Nobody else even comes close. And my mother? My mother was my heart.” - Kevin Poston They discussed Kevin’s extraordinary professional and personal life, his early failures that led to incredible success, our professional relationship and the NBA, the influence of his parents, his decision to go to law school, and his rise to becoming one of the greatest sports agents in the world. Kevin is a man who is full of hard-won experience and endless professional intelligence. He also cares. His passion and love for his family, his clients, and his work shines through his words. If you need an injection of practical wisdom, professional guts, and real love into your day, this is your episode. In this episode Michael and Kevin talked about: 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. Resources: Kevin Poston on InstagramMichael Redd on Instagram