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Betting On Yourself

Business & Economics Podcasts

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.

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.


United States


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.




Achea Redd: Fear-"less”

Mental health advocate, award-winning author, and influencer, Achea Redd, spoke with host and husband Michael Redd about her own journey from diagnosis to recovery, and her mission to help end the stigma associated with seeking mental health care, especially for women of color. “We have to let go of who we think we should be and embrace what is.” – Achea Redd Achea Redd is the author of “Be Free. Be You,” and founder of the non-profit, Real Girls F.A.R.T. – a space designed to empower and...


Lindsay Karas Stencel: Shatter the Glass Ceiling

Venture capitalist and attorney, Lindsay Karas Stencel, chatted with host Michael Redd about how success in competitive athletics translates to business success, her journey from elite athlete to high-powered lawyer, and her passion for supporting emerging and diverse voices in business and beyond. “I’ve always liked the idea of taking a concept and applying capital and talent and to turn that into what ultimately, in the best-case scenario, becomes a successful, high-growth company....


Charli Cohen: Always Trust Your Instincts

British fashion designer and entrepreneur, Charli Cohen, spoke with host Michael Redd about blending the digital and physical worlds, the value of staying small and agile through the pandemic, and how trusting her instincts has had a huge impact on fashion. “This whole COVID situation has been quite a leveler for the industry and been a way for smaller, more agile brands to stand out and innovate during this time.” – Charli Cohen Charli planned her first fashion collection at the age of 13...


Jeremy Pressman: Don’t Be Afraid to Fail

Venture capitalist and professional basketball player, Jeremy Pressman, rapped with host Michael Redd about his vision for the future of sports, and how his passion, drive, and ethos have helped shape his career. “Here you’re taught, you should, and you can ... fail time and time again. It’s a good character-building experience.” – Jeremy Pressman After a successful college stint at Yeshiva University Jeremy pursued a basketball career in Israel. Jeremy is a veteran of Israel’s Artzit...


Gene Smith: Focus On Yourself First

Senior VP and Athletic Director for The Ohio State University, Gene Smith, talked with host Michael Redd about his passion for helping student-athletes thrive, his journey from Eastern Michigan to Ohio State, and why it’s OK to be selfish sometimes. “Self-awareness is critical. Then you have to make sure you pay attention to your teammates. You’re not going through that challenge alone, so you need your teammates to be the best they can be… but it starts with me.” – Gene Smith Named “one...


Mike Su: Trust the Process

The tech entrepreneur and Director of the Yellow Accelerator at Snap Inc., Mike Su, chatted with host Michael Redd about how his career started with a comic book company, why taking the right risks strengthens your entrepreneurial drive, and choosing “the road less traveled.” “This moment has shown the importance of when leaders rise and leaders falter, in times of crisis … When the future’s uncertain, who are the ones that are willing to have difficult conversations, to point to things...


Jared Sullinger: Having the Right Mentors

Former Boston Celtics standout and NBA free agent, Jared Sullinger, got honest with host Michael Redd about surrounding yourself with the right people, the hardest part about going pro at a young age, and how to rekindle your motivation. “You have to play every game like it’s your last because you never know what’s going to happen.” – Jared Sullinger Coming out of his incredible, undefeated final year of high school Jared was a 2010 McDonald's All-American co-MVP, James A. Naismith Award...


Clark Kellogg - Let Humility Be Your Anchor

CBS College Basketball Analyst, and former NBA player and executive for the Indiana Pacers, Clark Kellogg, spoke with host Michael Redd about his time in the league, his dedication to a career as a top TV sports broadcaster, and how his faith has played a role in his success. “Don’t be afraid of the work, or the time it might take to hone your craft. Sports – basketball in particular – taught me some of those things as I transitioned from being on the court, and between the lines, to being...


Jason Day: Focusing on Your Mental Game

Former World No. 1 ranked pro golfer and philanthropist, Jason Day, took a break from the links to chat with host Michael Redd about his humble beginnings and rise to the top of the golf world, what it takes to persevere through injury, and his admiration of his mentor Tiger Woods. “I’m addicted to the process of getting better.” – Jason Day The Australian professional golfer and PGA Tour member is a former World Number 1 in World Golf Ranking. From 2015 to 2016 he was considered the best...


Spencer Dinwiddie: The Journey Is the Reward

Entrepreneur, VC, and NBA star, Spencer Dinwiddie, took some time to chat with host Michael Redd about his challenges along the journey to pro basketball, what it means to surround yourself with the right people, and being “... a tech guy with a jumper.” “Basketball is just the tip of the iceberg. Off the court, I build businesses that improve the lives of others and make the world a better place.” – Spencer Dinwiddie An “unstoppable force,” both on and off the court, Spencer currently...


Hamet Watt: Navigating Entrepreneurship

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...


Brett Kaufman: The Secret Sauce for Success

Real estate developer and CEO, Brett Kaufman, took time to chat with host Michael Redd about entrepreneurship as a form of creativity, how he decided to build “communities centered on wellbeing, expression, and impact,” and his passion for creating “spaces that optimize the human experience.” "The building is just the beginning. The true value is what happens in and around it. We design communities for individuals who seek something more." – Brett Kaufman Brett is a “champion of...


Josh Childress: Create as Much Impact as You Can

The venture capitalist and former NBA journeyman, Josh Childress, spoke with host Michael Redd about his winding path from Compton to Stanford, the NBA, and beyond, why he went back to college (twice) after pro sports, and his passion for real estate, investing, and community redevelopment. "I wanted to shift from receiving checks to writing them.’" – Josh Childress Josh was a standout basketball star in high school and college – named a McDonald's High School All-American, AP first-team...


Chris Broussard: Being True To Yourself

Fox Sports analyst, commentator, and radio host, Chris Broussard, took time out to chat with host Michael Redd about his path to becoming an influential voice in sports journalism, how betting on himself has allowed him to remain objective, and his involvement with the K.I.N.G. Movement. "When I talk to young people I say, ‘There’s a fine line between confidence and arrogance … and you have to learn how to walk it.’" – Chris Broussard Chris is a longtime sports journalist, best known for...


Nate DeMars: How to Carve Out Your Niche

Founder and CEO of Pursuit: Suiting the Next Generation, Nate DeMars, spoke with host Michael Redd about his slow evolution of confidence to finding success, the unlikely stepping stones that helped him build a remarkable career, and how to carve out a niche that you're passionate about. "Run in the direction of the things you’re excited about … but know that when you get there, it’s going to look very different than how you thought it would look." – Nate DeMars The entrepreneur started...


Erica Williams Simon: Take a Leap of Faith

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....


Jason Ross: Success Doesn’t Happen Overnight

The founder of JackThreads and serial entrepreneur, Jason Ross, spoke with host Michael Redd about his early days as a broke entrepreneur, the big gamble of launching (and selling) his own startup, and what it takes to survive the ups and downs of the business world. "I wrote the business plan and spent two and a half years just working out of my house to get it started." – Jason Ross Named after his grandfather, Jason founded JackThreads in 2008 – a members-only flash sale site for the...


Mike Conley Jr.: How to Be a Fearless Competitor

NBA point guard for the Utah Jazz and all-time leading scorer for the Memphis Grizzlies, Mike Conley Jr., joined host Michael Redd to talk about how to develop a winning mentality, why preparation and mental toughness are the keys to great achievements, and his journey as a pro athlete. “The reason players aren’t afraid is they don’t think of the moment. For me, you don’t let the moment overtake you, you don’t think about the score, you don’t think about failure. You think about the...


Ray Allen: On Playing the Long Game

Two-time NBA champion, Hall of Famer, and fellow Olympic gold medalist, Ray Allen, joined Michael to reminisce about what it takes to play the long game in basketball, life, and the discipline required to be a champion. “I believe that everything that I learned in my career, everything that sustained me for 18 seasons, it’s important to pass that along,” – Ray Allen Allen is a 10-time NBA All-Star considered by many to be the greatest three-point shooter of all-time. He was inducted into...


Jeni Britton Bauer: Succeeding Against the Odds

In the inaugural episode of Betting On Yourself the founder and Chief Creative Officer of Jeni’s Splendid Ice Creams, Jeni Britton Bauer, joined Michael to speak about the story of her success, the definition of "betting on yourself," and the early life struggles that motivated her. “No one else makes ice cream like Jeni Britton Bauer.” – Food & Wine Magazine The James Beard award-winning ice cream maker and entrepreneur is a pioneer of the widely copied, ingredient-driven, artisan ice...