Betting On Yourself
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Betting On Yourself episodes

  • 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 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

    26 min
  • 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 LinkedIn
    Jubilee Media
    Jubilee Media on LinkedIn
    Jubilee Media on Instagram
    Michael Redd
    22 Ventures

    39 min
  • 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 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

    39 min
  • 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
    39 min
  • 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
    48 min
  • 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
    51 min
  • 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
    32 min
  • 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
    43 min
  • 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
    41 min
  • 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
    39 min

About Betting On Yourself

From the publisher's feed

Michael Redd, former NBA All-Star turned world-class investor, unpacks the stories of successful entrepreneurs and athletes who risked everything to get where they are today. Betting On Yourself…