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Betting On Yourself

62 Episodes

29 minutes | Sep 5, 2022
Gary Vaynerchuk: Proving Them Wrong
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 VaynerchukGary Vaynerchuk on LinkedInGary Vaynerchuk on TwitterGary Vaynerchuk on InstagramVaynerXMichael Redd22 Ventures
46 minutes | Aug 29, 2022
Wil Schroter: Learning From the Bets You Lose
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 TwitterWil Schroter on InstagramWil Schroter on LinkedInStartups.comStartup Therapy PodcastFounders Group on LinkedIn Michael Redd22 Ventures
37 minutes | Aug 22, 2022
Cuttino Mobley: You Have a Responsibility to Bless Others
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 TwitterCuttino Mobley on InstagramCuttino Mobley on LinkedInSean Colson on TwitterTyson Wheeler on TwitterCameron Pooler on InstagramAlvin Williams on TwitterHakeem “Dream” Olajuwon on TwitterMichael Redd22 Ventures
33 minutes | Jul 25, 2022
Dan Cnossen: Choose Your Perspective
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 CnossenDan Cnossen on LinkedInMichael Redd22 Ventures
40 minutes | Jul 18, 2022
Corey Arvinger: Lead Through Your Actions, Not Your Words
"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 CollegesSupport Black Colleges on InstagramCorey Arvinger Corey Arvinger on InstagramTeyana TaylorMichael Redd22 Ventures
32 minutes | Jul 11, 2022
Doug Ulman: Anything Is Possible
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 RatherUlman FoundationLivestrongPelotoniaDoug Ulman on TwitterMichael Redd22 Ventures
35 minutes | Jul 4, 2022
Don Yaeger: Cultivating Curiosity
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 YaegerDon Yaeger on LinkedInDon Yaeger on InstagramDon Yaeger on TwitterMichael Redd22 Ventures
34 minutes | Jun 27, 2022
Nick Potts: Some Level of Almost Arrogance
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 LinkedInNicholas Potts on InstagramGifthealthGifthealth on InstagramScriptDropMichael Redd22 Ventures
45 minutes | Jun 20, 2022
Lacey Picazo: Setting Your Own Table
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: An introduction to today’s guest, Lacey Picazo, founder of ZoCo Design. What ‘betting on yourself’ means to Lacey: realizing your own power. How wanting to do things differently motivated her to start her business. Why it is so important to be humble and ask for help. Managing fear and choosing not to focus on what could go wrong.  The difference between UX and UI.  The founding principles of ZoCO: human-centered design. Why she believes that experience is one of the number one drivers towards business and technology.  The many hats you have to wear in the beginning phases of your business. How, as the business grows, you need to learn how to delegate and share responsibility. Hiring people who are smarter than you in order to make delegation easier. Why she would rather be a thought partner than constantly resolve problems.  How she goes about intentional hiring, and what happens when you trade on your values. The value they place on growing the skillsets of their team members through training, round tables, and design assemble, as well as bringing experts in. Reinforcing values through human storytelling within ZoCo.  Their target client: head of product at a customer-centric software company. Supporting female leadership within the workforce. Parenting, entrepreneurship, and business ownership.  The role of peer feedback in supporting work-life balance and gaining perspective. Advice she would give to her 16-year-old self: ask yourself, is this something only I can do, is this something I want to do, and is this something that has to be done?  ZoCo’s goal to work with amazing people seeking to solve problems.  Lacey’s aim to be a visionary and to wear fewer hats within ZoCo, in order to find balance. 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 DesignLacey Picazo on InstagramLacey Picazo on TwitterLacey Picazo on LinkedInMichael Redd22 Ventures
39 minutes | Jun 13, 2022
David Meltzer: Elevating Others to Elevate Yourself
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: How David's life changed when his mother encouraged him to bet on himself. His mother's influence on his trajectory, both in business and in life. The extraordinary value of going the extra mile every day, not just once in a while. Discover where David's faith-based passion for people comes from. What it means to be a true servant leader and how David defines happiness. The important roles that identity and self-awareness play in "getting out of your own way." The five levels of betting on yourself: do, say, think, believe, and feel! Insight into the incredible challenges David has had to overcome along the way. How to shift out of an ego-based consciousness and go from liability to accountability. The critical role that self-awareness and introspection play on this journey. The biggest lesson (not regret) that David took from his journey: ask for help! Hear the remarkable story of how David came to partner with Warren Moon. What is next for David, from more content plays to more mastermind teachings! 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 MeltzerDavid Meltzer EmailDavid Meltzer on TwitterDavid Meltzer on LinkedInDavid Meltzer on InstagramCompassionate CapitalismConnected to Greatness
25 minutes | Jun 6, 2022
David Shands: Playing to Your Strengths
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: David explores the idea of betting on yourself and his experiences of taking this kind of chance.  The ethos of risk-taking and circumstances that gave David this ability.  How David's faith has laid the foundation for his life and success.  The transition that David made from working at The Cheesecake Factory into the world of entrepreneurship. Why David found himself starting his own podcast! Thoughts on commitment issues and how these can stand in the way of success. David weighs in on the concept of failure and common reasons for people missing their goals.  Entrepreneurship and identity; David's thoughts on accepting weaknesses and finding ways to learn.  A multilayered definition of success from David!  How to stay mindful of the different demands we have on our time.  The process of self-evaluation and the importance of this on a continual basis.  David's thoughts on the idea of podcasts replacing music!  We get some insight into the morning meetups that David hosts.  The advice that David would give his younger self about trust. David shares some of his goals for the future and what he still hopes to achieve. 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 InstagramSocial Proof PodcastSleep Is 4 SuckersDavid Shands on TwitterLeBron JamesLos Angeles LakersGolden State WarriorsThe Cheesecake FactoryMichael Redd22 Ventures
39 minutes | May 30, 2022
Jason Y. Lee: Shedding the Need for Validation
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: Introducing today's guest Jason Y. Lee, founder of Jubilee Media. What it has meant for Jason to bet on himself and pursue a non-traditional path. How Jason's parents bet on themselves but wanted a more conservative trajectory for their children. Jason's definition of success and why it's all about having a positive impact. The challenge of embracing our own identity and not being defined by the expectations of others. The early success Jason experienced in life and business while working at Bain and what it meant for him to listen to his inner voice.  How to determine what you want and when to listen to your inner voice. The monumental decision Jason and his brother made to quit their respective jobs and create Jubilee Media. The mindset you need to have when facing doubt and fear. Why Jubilee Media is all about radical empathy and creating human connection. Jason's thoughts on being named an influencer of the year and why he is trying to shed the need for validation. How the COVID-19 pandemic affected talent retention and company culture. Hear what Jubilee Media has coming up, including a new documentary! 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 LinkedInJubilee MediaJubilee Media on LinkedInJubilee Media on InstagramMichael Redd22 Ventures
38 minutes | May 23, 2022
Ron Jordan and Tom Krouse: The Power of Partnerships
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: An introduction to the partnership that has brought us together for today's episode!  The family values that Tom brings into his work and business.   Ron's early memories of his grandfather and how this inspired his work ethic and determination. Tom's reflections on navigating the last two years and the challenges of the pandemic.  We hear from Ron about dealing with adversity at this point in his career.   The seeds of Ron's involvement and partnership with Donatos.   Innovation and consistency at Donatos; how Jim Grote prioritized delivering to his customers.   Looking to the future and finding the best route for growth at Donatos and beyond.  Challenges in scaling a business like Donatos, that has strict standards of quality.   Why impact is at the top of Ron's list and his ongoing mission in his career. 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 LinkedInTom Krouse on LinkedInDonatosJordan Hospitality GroupDonatos on InstagramJim GroteAlex ShumateGrote CompanySonoma FlatbreadsRed Robin Michael Redd22 Ventures
39 minutes | May 16, 2022
Coach Scoonie Penn: How to Walk Into the Unknown (and Win)
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: What betting on yourself means to him Pushing himself at a young age Being a leader within his family and in sports How he began to surpass his peers in playing What his best coaches did for him How to do the work when you can’t work The NBA draft and his time in Europe His future goals as a coach The 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 Penn on Instagram Michael Redd on Instagram
47 minutes | May 9, 2022
Thaddeus Young: Doing Whatever it Takes
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: What betting on yourself means to him His tough upbringing in Memphis The business influence of his uncle His greatest inspiration in life Leaving college basketball after one year His early entry into the NBA Draft What it was like to finally get into the NBA His struggle to make his mark in the early years of playing How he handles adversity How playing the game has changed over 15 years His drive as an entrepreneur The 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: Thaddeus Young on Instagram Michael Redd on Instagram
50 minutes | May 2, 2022
T.J. Ford: The Willingness to Risk Everything
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 him What it meant coming from a basketball family Who inspired him as a young man His two high school championships His early struggle with spinal stenosis The importance of making bold decisions His viral moment, before viral moments existed How he approached the NBA as an underdog The mindset of the epic comeback How he thinks he’d fare in today’s NBA game The story of the T.J. Ford Academy The 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 Instagram Michael Redd on Instagram
31 minutes | Apr 25, 2022
Tzvi Twersky: If You Don’t Bet On Yourself, Who Will?
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: What betting on yourself means to him How he got his first job as a sports writer The “angle” that took him to the pinnacle of pro sports How to get where you want to be Why he invests in people and relationships first Who inspired him the most as a young man His friendship and work with Kobe Bryant What people don’t know about NBA players His current work with Tik Tok What continues to drive him every day The 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: Tzvi Twersky on Instagram Michael Redd on Instagram
42 minutes | Apr 18, 2022
Iyin Aboyeji: The Challenges are Always The Opportunities
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: What betting on yourself means to him His original desire to be accepted by Silicon Valley His ultimate commitment to Africa Thinking about the challenges in Africa His incredible success in multiple startups What it’s like growing up as a Pastor’s kid Lessons learned from his mother and father His vision for the future of Africa Building the first “unicorn” company in Africa The aggregation of capital and the allocation of capital The 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: Iyin Aboyeji on Twitter Michael Redd on Instagram
41 minutes | Apr 11, 2022
Coach Chris Holtmann: Choose to Challenge Yourself
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 him Why he’s never been afraid of risk How his family has impacted his life choices His greatest professional influences The importance of service and humility Why no task is beneath the truly great Why he took a “step back” in order to go forward Your responsibility is consistent and daily work The reality of seeking out a major coaching job The days of “transactional coaching” are over The 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 Twitter Michael Redd on Instagram
39 minutes | Apr 4, 2022
Kevin Poston: Don’t Cheat Yourself
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: What betting on yourself means to him What early failure taught him about himself His early entrepreneurial efforts How he learned his “why” His decision to go to law school The advice that changed the course of his life How his wife “out-negotiated” him His rise as a sports agent How he negotiated over one billion dollars in contracts The 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: Kevin Poston on Instagram Michael Redd on Instagram
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