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Betting On Yourself

Betting On Yourself

Michael Redd

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 explores how these incredible successes built their legacies by taking their success into their own hands.
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Top 10 Betting On Yourself Episodes

Goodpods has curated a list of the 10 best Betting On Yourself episodes, ranked by the number of listens and likes each episode have garnered from our listeners. If you are listening to Betting On Yourself for the first time, there's no better place to start than with one of these standout episodes. If you are a fan of the show, vote for your favorite Betting On Yourself episode by adding your comments to the episode page.

Betting On Yourself - Hamet Watt: Navigating Entrepreneurship
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07/27/20 • 41 min

Venture capitalist, serial entrepreneur, and Founder of Share Ventures, Hamet Watt, hit pause to rap with host Michael Redd about what it takes to navigate the waters of entrepreneurship, how to wire your business for success, and his optimism for the future of “inclusive innovation” and solving social justice problems.

"Being able to find your way out of situations that you think are impossible, is what inspires you to take bigger risks knowing that you're gonna get out if it happens again." – Hamet Watt

Prior to helping co-found both MoviePass and bLife (a wellness innovation company acquired by Canary Health), Hamet was an Entrepreneur In Residence with True Ventures.

Hamet was also a Board Partner at Upfront, a VC company that “...strives to invest in companies that consciously work to build diverse teams,” and founded NextMedium, the first full-service platform for buying, selling, and measuring product placement across entertainment content.

He has advised Nielsen Media Research in the development of their first product placement measurement service for network and cable TV, and was General Partner in the New Africa Opportunity Fund, the first US-backed venture fund investing in post-apartheid South Africa.

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

In this episode Michael and Hamet talked about:

  • How to tamp down pessimism and focus on the future
  • Hamet’s definition of entrepreneurship and why you need to have agency
  • Traits that VCs look for in entrepreneurs (and their inherent biases)
  • Why “...your dream will only go as far as your team”
  • The importance of being a problem solver in business
  • And using data to shave the failure rate for new companies

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

Resources:

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Betting On Yourself - Erica Williams Simon: Take a Leap of Faith
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06/22/20 • 39 min

Founder and CEO of Sage House, entrepreneur, and author, Erica Williams Simon, chatted with host Michael Redd about betting on yourself as a way of life, taking a leap of faith early in her career, and why developing a “sixth sense” is so important for finding your calling.

"The contingency plan is you, and needs to be one tied to who you are." – Erica Williams Simon

The social critic, media personality, and reformed Washington politico has been a lifelong civil and human rights activist. Through her company, Sage House, Erica helps people and brands “uncover wisdom for living and working in a modern world.”

Her recent book You Deserve the Truth (Simon & Schuster), is described as, “Part memoir, part blueprint [to help] a diverse young generation of dreamers and doers understand the power of story: how to see it, understand it and master it for better lives - and a better world.”

The former Head of Creator’s Lab for Snapchat is also a popular moderator and interviewer, host of the popular podcast The Call with Erica, and creator and host of the Rosario Dawson produced digital talk show The Assembly.

She has been featured on The Today Show, O Magazine, and The Washington Post and is a frequent TV commentator.

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

In this episode Michael and Erica talked about:

  • Why she quit a career in politics – with no backup plan – to follow her true voice
  • The importance of vision, wonder, and curiosity on her journey
  • How her father’s last words guide her life’s calling
  • The power of self-actualization and her definition of success
  • Why the older you get, the smarter your parents’ wisdom becomes
  • And creating new paradigms for betting on yourself

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

Resources:

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Betting On Yourself - Gary Vaynerchuk: Proving Them Wrong
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09/05/22 • 28 min

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

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Betting On Yourself - Iyin Aboyeji: The Challenges are Always The Opportunities
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04/18/22 • 42 min

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:

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Betting On Yourself - Steven Lim: Reaching Millions by Tasting Food
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02/08/21 • 51 min

Steven Lim, owner of Watcher Entertainment, and the creator/host of the YouTube series “Worth It,” joined host Michael Redd to talk about second-guessing himself, taking risks when he wanted to play it safe, and rejecting – then accepting – a job offer that would ultimately open the door to his viral online success.

“I didn’t start making videos because I wanted to make cat videos... I came here because I wanted to make really meaningful, impactful videos about culture, identity, and food.” – Steven Lim

On his wildly popular Buzzfeed YouTube series “Worth It” – gearing up for Season 9 – Steven tastes pricey food from all over the world. A long way from his hometown in Ohio, he now impacts millions with his work and world travel, including Japan, where he ate the best meal of his life.

Watcher Entertainment was launched in January 2020 by Steven Lim, Ryan Bergara, and Shane Madej. Their production studio created the viral shows Worth It and BuzzFeed Unsolved, “... and is focused on creating television-caliber, unscripted series in the digital space.”

Note: Due to technical difficulties this interview was recorded on Zoom.

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

In this episode Michael and Steven talked about:

  • How a career in chemical engineering took an about-face
  • Why he started making YouTube videos on his phone
  • Making an impact with your platform for a greater purpose
  • Why his vision and values validated his intuition as a content creator
  • How to get syndicated on Hulu and Amazon
  • Why “taste is the language everyone speaks”
  • And more!

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

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Betting On Yourself - Christoph Sonnen: Waiting for the Perfect Wave
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01/11/21 • 40 min

Entrepreneur and venture capital expert, Christoph Sonnen, reunited with host Michael Redd to talk about his road to success and what betting on yourself really means to him.

“Great business ideas are like surfing. You won’t make it if you’re too early, you won’t make it if you’re too late.” – Christoph Sonnen

Christoph is the co-founder and CEO of leAD sports accelerator and is also a partner at ADvantage Sports Tech Fund, joining forces with Jeremy Pressman and friend Michael Redd with a commitment to invest in early-stage tech companies shaping the future of sports.

Over the last 20 years, he has founded, managed, and sold several businesses, structured funds, investments, and accelerator projects.‍ He is passionate about building the right team and believes in having the vision to be able to see the next big thing.

A world-class surfer, Christoph compares entrepreneurship and building a business to waiting for the perfect wave. That success is not so much about being the best, but knowing when to make your move as you see it.

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

In this episode Michael and Christoph talked about:

  • How great business ideas are like surfing
  • Why startups need to learn how to hold their breath underwater (without panicking)
  • Takeaways on Christoph’s first (and last) job at Red Bull
  • How he combined sports, tech, and his venture experience to great success
  • What the future of sports tech looks like
  • The challenges and rewards of venture life
  • And more!

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

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Betting On Yourself - Cuttino Mobley: You Have a Responsibility to Bless Others
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08/22/22 • 36 min

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

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Betting On Yourself - Dan Cnossen: Choose Your Perspective
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07/25/22 • 33 min

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

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Betting On Yourself - Don Yaeger: Cultivating Curiosity
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07/04/22 • 34 min

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

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Betting On Yourself - Ron Jordan and Tom Krouse: The Power of Partnerships
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05/23/22 • 38 min

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

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FAQ

How many episodes does Betting On Yourself have?

Betting On Yourself currently has 62 episodes available.

What topics does Betting On Yourself cover?

The podcast is about Business, Education, Self-Improvement, Podcasts and Entrepreneurship.

What is the most popular episode on Betting On Yourself?

The episode title 'Wil Schroter: Learning From the Bets You Lose' is the most popular.

What is the average episode length on Betting On Yourself?

The average episode length on Betting On Yourself is 43 minutes.

How often are episodes of Betting On Yourself released?

Episodes of Betting On Yourself are typically released every 7 days.

When was the first episode of Betting On Yourself?

The first episode of Betting On Yourself was released on May 11, 2020.

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