Betting On Yourself

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 plays for the NBA’s Brooklyn Nets and played college basketball for the Colorado Buffaloes where he earned first-team all-conference honors in the Pac-12 as a sophomore in 2013. 

His story of perseverance began after injuring his anterior cruciate ligament (ACL), and missing most of his junior year in college. He was determined to speed his recovery and was selected in the second round of the 2014 NBA draft.

During the 2016-2017 season, all-star weekend, he won the NBA skills challenge, and the following season was a top 5 passer and a top 5 isolation player. The day after scoring a career-high 39 points in a win over the Philadelphia 76ers, he signed a three-year contract extension with the Nets.

Spencer has launched three businesses and partnered with a fourth that aim to accomplish his mission to give back to communities in need, including The Dinwiddie Family Foundation, Project DREAM, DREAM Fan Shares, and The Cred Partnership.

His mission is “... to build companies that create value in the world and that strive to make the lives of others better.”

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 Spencer talked about:

• How resiliency and a no regret attitude are essential to success
• Why startups are not for the faint of heart
• When to bet on yourself and go for the broke on your own terms
• Why staying true to yourself, owning your differences, and chasing your passions leads to excellence
• How Spencer has been a trailblazer for empowering a generation of NBA players
• And more hot takes on the state of the world and business!

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

Resources:

• SpencerDinwiddie.com
• Spencer Dinwiddie on LinkedIn
• Spencer Dinwiddie on Twitter
• Michael Redd on Instagram

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:

• Upfront's Hamet Watt Launching New Startup Studio
• Hamet Watt on LinkedIn
• Hamet Watt on Twitter
• Michael Redd on Instagram

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 innovative, curated communities filled with purpose” and the founder and CEO of the Columbus, Ohio based Kaufman Development, who has worked in real estate development for 20 years. Over that time he has developed, leased, and/or sold over 10,000 homes and developed a variety of commercial, retail, land, and office projects.

He’s also a philanthropist who has dedicated much of his professional life to helping community organizations and Kaufman Development has donated numerous resources to philanthropic organizations including Besa, KIPP Journey Academy, Community Shelter Board, Ohio State University Star House, Hunger Alliance, Ronald McDonald House, OSU James Cancer, Columbus Jewish Federation, and many others.

Kaufman is a lauded and award-winning community leader who “... has been recognized as one of the top 50 leaders in the region for his ability to drive innovation within his organization, impact his employees and the community-at-large... In 2015 and 2016 Brett [was] honored with Smart 50 and Fast 50 awards and was recently listed at #657 on the Inc. 5000.”

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 Brett talked about:

• The freedom of betting on yourself
• How to succeed in business with nothing but a piece of paper and an idea
• Why embracing the things that make you different (and stepping into fear) can be so empowering
• On finding tools to uncover your deeper identity and the power of daydreaming
• The critical importance of mentorship, the essence of entrepreneurship...
• And more!

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

Resources:

• LiveKaufman.com
• Brett-Kaufman.com
• Brett Kaufman on Instagram
• Brett Kaufman on Twitter
• Michael Redd on Instagram

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 All-American, Pac-10 Conference Player of the Year, and the Pac-10 Conference Tournament MVP as a junior at Stanford in 2004 – who was selected with the sixth overall pick in the 2004 NBA draft by the Atlanta Hawks.

He has played in the NBA with the Atlanta Hawks, Phoenix Suns, Brooklyn Nets, and New Orleans Pelicans, and traveled the globe playing professional basketball for teams in Greece, Australia, and Japan.

Childress, after being waived by the Brooklyn Nets in 2013, enrolled back at Stanford and graduated with his degree in sociology in August 2013. He is currently enrolled in a Masters program in Real Estate at Georgetown.

His over 10 years experience as a venture capitalist and real estate investor, and his passion for community building and philanthropy, led him to co-found LandSpire Group, an LA-based “...real estate investment fund that revitalizes communities of color that were once defined by small businesses, livable-wage jobs, and a thriving middle class.”

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 Josh talked about

• Josh’s trailblazing journey from pro basketball to successful businessman
• When Michael and Josh both realized a desire to leverage their influence to give back to the community
• How dealing with adversity early on drove Josh to succeed
• Why Josh turned down a $35M NBA deal to play basketball in Greece
• On going from the pro level as an athlete to a novice venture capitalist
• The critical importance of mentors and giving back
• And more!

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

Resources:

• Josh Childress
• LandSpire Group
• Josh Childress on Instagram
• Josh Childress on Twitter
• Michael Redd on Instagram

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 his coverage of the NBA, and has contributed to The New York Times, ESPN The Magazine, ESPN.com, and has appeared as an analyst on ESPN's SportsCenter, NBA Countdown, First Take (alongside FS1 colleague Skip Bayless – whom he joins regularly as a contributor on Undisputed), and NBA Fastbreak.

The Fox Sports 1 commentator also co-hosts a radio show and podcast with fellow FS1 sports analyst Rob Parker on FOX Sports Radio that “... takes listeners through the biggest hits in sports.” The Odd Couple with Chris Broussard & Rob Parker can be heard on FOX Sports Radio and Sirius XM Channel 83.

Broussard is also an active philanthropist who serves as Founder and President of the K.I.N.G. Movement, a national Christian men’s organization.

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 Chris talked about:

• The fine line between confidence & entitlement, and the Chris Broussard Rule
• How to get a job in the big leagues of sports reporting
• Why it’s so important to focus on academics … even when you don’t have a career objective
• On not selling dreams, starting from the beginning, and the legend of Stuart Scott
• Why you need to be true to yourself and keep it real in broadcasting
• How data analytics has changed pro sports forever
• And his mission through the K.I.N.G Movement to empower men through Christianity

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

Resources:

• Chris Broussard on Fox Sports
• The Odd Couple with Chris Broussard & Rob Parker - Apple Podcasts
• www.ChrisBroussardSpeaks.com
• KingMovement.com
• Chris Broussard on Instagram
• Chris Broussard on Twitter
• Michael Redd on Instagram

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 Pursuit – a modern suit store with an old-fashioned customer service model – in an entrepreneurship class for an MBA program at the Ohio State University’s Fisher College of Business back in 2011. He’s been fitting cufflinks ever since as a pillar of the business community in the Short North district of Columbus, Ohio.

He is also an Entrepreneurship Lecturer for Ohio State University’s Fisher College of Business where he works with the next generation of Buckeye entrepreneurs.

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 Nate talked about:

• How Nate came to entrepreneurship in the second chapter of his career
• Why playing a smaller role at a Fortune 500 company helped prepare him to launch his own business
• On hard right turns, blessings in disguise, and the importance of family
• How he found himself in fashion and retail after studying commercial real estate
• The reason ignorance is bliss when you’re starting out in a new sector
• Why it’s not worth doing if you’re not passionate about it
• And how customer service makes all the difference

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

Resources:

• Pursuit: Suiting the Next Generation
• Nate DeMars on LinkedIn
• Nate DeMars on Twitter
• Michael Redd on Instagram

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:

• Erica Williams Simon’s Homepage
• Erica Williams Simon on Twitter
• Erica Williams Simon on Instagram
• Michael Redd on Instagram

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 streetwear community – and was working out of a bedroom in Columbus, OH.

By May of 2010, Thrillist had acquired JackThreads.com, the startup Jason helped build to $100m in annual revenues and over two million members (he departed in 2014).

JackThreads was listed as one of Ad Age’s America's Hottest Brands, Inc's Fashion Startups to Watch, Entrepreneur's Top Retail Sites and as the fastest-growing men's e-commerce company on Internet Retailer's 500 List.

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 Jason talked about:

• The mindset needed to be successful in the face of adversity
• How Jason rolled up his sleeves right out of college and bet on himself
• Why entrepreneurship is so iterative and success is not a straight line
• The genesis of Jason’s bootstrapped, $100m idea (and why he sold it)
• On the marriage of passion and high-growth opportunities
• Why you need to surround yourself with the right (and smartest) people
• And much more!

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

Resources:

• Jason Ross on LinkedIn
• 30 UNDER 30 2016: Jason Ross, Founder of JackThreads – Inc.
• JackThreads.com
• Jason Ross on Twitter
• Michael Redd on Instagram

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 opportunity that lies ahead.” – Mike Conley Jr.

The fourth overall pick in the 2007 NBA draft is a three-time NBA Sportsmanship Award-winner and was the franchise leader in multiple categories during his 12 seasons with the Grizzlies.

Mike Conley Jr is considered one of the best point guards in the NBA, and is certainly one of its toughest competitors. He was the highest-paid player in the NBA at one point and is also an impassioned philanthropist.

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 Mike talked about:

• How Mike's family Olympic legacy imprinted a model for success
• Why losing is sometimes the best teacher
• Mike's daily regimen for keeping his competitive edge
• Great advice on balancing family and career
• On fearlessness and rising above high-pressure moments to win
• And much more!

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

Resources:

• Mike Conley Jr.
• Jazz guard Mike Conley Jr. wins NBA HORSE Challenge
• MichaelRedd.com
• Michael Redd on Instagram

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 the Naismith Memorial Basketball Hall of Fame in September 2018 and is also an accomplished actor, author, entrepreneur, and influencer.

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!

*Note: Ray Allen recorded this podcast outside, so there might be some background noise.

In this episode Michael and Ray talked about:

• Lessons Ray learned early on about the secrets to long-term success
• Why you need to show up every day, every moment to be a champion
• On finding good influences, choosing happiness, and betting on yourself
• Why you'll never be as great as you think you are ... without humility and hard work
• How adversity is the key to change and growth
• And life after basketball

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

Resources:

• Ray Allen |  Naismith Memorial Basketball Hall of Fame
• MichaelRedd.com
• Michael Redd on Instagram