Listen and subscribe to Financial Freestyle on Apple Podcasts, Spotify, or wherever you find your favorite podcasts.

In this episode of Financial Freestyle, host Ross Mack sits down with Olajuwon Ajanaku and Earl Cooper, the founders of Eastside Golf, to discuss their journey from professional golfers to fashion moguls. Olajuwon and Earl discuss their early connections to golf, meeting at Morehouse College, and how identifying a lack of representation in golf apparel set them on a path to success. Tune in to learn more about their unique brand and their push to make the game of golf accessible to all.

Financial Freestyle with Ross Mac on Yahoo Finance is dedicated to promoting economic prosperity for all. Through expert insights, practical advice, and inspiring success stories, we empower you to build and grow wealth. Join us on this transformative journey toward financial freedom and inclusive economic growth.

This post was written by Dennis Golin.

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Listen and subscribe to Financial Freestyle on Apple Podcasts, Spotify, or wherever you find your favorite podcasts.

In this episode of Financial Freestyle, host Ross Mack sits down with Ashley Fox, CEO of Empify, to discuss her journey from Wall Street analyst to fintech entrepreneur. Ashley shares how her company is revolutionizing financial education by providing wealth-building tools for everyday people, including school and prison programs. Tune in for an inspiring conversation on financial empowerment and making wealth education accessible to all.

Financial Freestyle with Ross Mac on Yahoo Finance is dedicated to promoting economic prosperity for all. Through expert insights, practical advice, and inspiring success stories, we empower you to build and grow wealth. Join us on this transformative journey toward financial freedom and inclusive economic growth.

This post was written by Austin Rivera.

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Listen and subscribe to Financial Freestyle on Apple Podcasts, Spotify, or wherever you find your favorite podcasts.

Investor and educator Ian Dunlap joins Financial Freestyle with Ross Mac to share the key strategies that separate successful investors from those who miss out. From avoiding risky financial traps to picking the right stocks, this episode is packed with insights to help you build lasting wealth.

Financial Freestyle with Ross Mac on Yahoo Finance is dedicated to promoting economic prosperity for all. Through expert insights, practical advice, and inspiring success stories, we empower you to build and grow wealth. Join us on this transformative journey toward financial freedom and inclusive economic growth.

This post was written by Austin Rivera.

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In this episode of Financial Freestyle with Ross Mac, entrepreneur and personal finance creator Austin Hankwitz shares his journey from finance professional to social media success, breaking down how he built multiple income streams and helps others grow their wealth. From smart investing strategies to leveraging AI for side hustles, Austin drops invaluable insights on achieving financial freedom and making money work for you.

Thoughts? Questions? Fan mail? Email us at [email protected]

"Financial Freestyle with Ross Mac" on Yahoo Finance was created by John Tejada, and this episode was produced by Austin Rivera.

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In this episode of Financial Freestyle, host Ross Mac sits down with Hugh Tamassia, co-founder of Alix, to discuss the massive $84 trillion wealth transfer expected through 2045 and how AI is revolutionizing estate settlements.

Hugh shares how Alix is helping families navigate the complex and time-consuming process of managing a loved one’s assets after they pass away—handling everything from bank accounts and subscriptions to real estate and taxes. He also dives into his journey as a tech entrepreneur, lessons learned from working at major financial institutions like JP Morgan and Acorns, and why keeping a human touch in AI-driven services is essential.

Whether you’re an investor, entrepreneur, or simply planning for the future, this conversation is packed with insights on financial literacy, innovation, and the future of estate management. Tune in now!  

Thoughts? Questions? Fan mail? Email us at [email protected]

"Financial Freestyle with Ross Mac" on Yahoo Finance was created by John Tejada, and this episode was produced by Austin Rivera.

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Whether you sit in a pro or anti-AI camp, it's hard to criticize the approach that this nonprofit is taking with the technology. On this week's episode of Financial Freestyle, host Ross Mac spoke with Chicago Scholars CEO Jeff Beckham, whose organization focuses on using AI as a tool to transform career coaching for kids, making it more interactive and engaging.

Chicago Scholars' AI platform offers personalized career guidance, helping students understand their strengths and goals. "We work to coach young people through the process of picking that career," Beckham says. "We do a lot of personal development, soft and hard skill development in platform; using videos and using gaming so that students are making better decisions on the front end so that they stay in their jobs longer, and that they're more qualified when they walk into the companies they're working for." By making career coaching feel more like an interactive experience, AI is helping students feel more confident in their choices and better prepared for the workforce.

While AI can enhance the process, Beckham emphasized that it’s not meant to replace the real work. “One of the things our AI won’t do is that in the resume builder, a student can upload the resume, they can build it in-platform, they can ask for advice, but it will not write it for them,” he makes clear. Chicago Scholars trained their own LLM to uniquely leverage AI as a tool, ensuring that students use AI responsibly.

Beyond AI’s impact on education, Mac and Beckham also discussed the financial struggles nonprofits face. With rising costs and shifting donor priorities, traditional funding models are becoming harder to sustain. To adapt, Chicago Scholars has introduced new revenue-generating strategies, such as charging companies for access to its talent pipeline. “I've figured out how to fund the organization hopefully in perpetuity,” Beckham said, emphasizing that for nonprofits to survive, they must innovate—not just in how they serve their communities, but in how they sustain their missions.

Thoughts? Questions? Fan mail? Email us at [email protected]

"Financial Freestyle with Ross Mac" on Yahoo Finance was created by John Tejada, and this episode was produced by Rachael Lewis-Krisky.

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Esports is no longer just a pastime for gaming enthusiasts — it become a legitimate path to growth and success, offering kids a sense of purpose, camaraderie, and even career opportunities that many might never have had access to before. In this week’s episode of Financial Freestyle, host Ross Mac speaks with PlayVS CEO Jon Chapman, also the former Co-Founder and President of EVERFI, to explore the growing impact of esports on today’s youth.

Chapman shares how PlayVS is transforming school sports by making esports an officially sanctioned activity, allowing kids to compete for state championships and earn varsity letters in titles like League of Legends, Rocket League, and Madden in 27 states.

He adds that esports is the first experience with extracurricular activities for many students, providing them with a sense of belonging and a purpose. "These are all exciting opportunities where kids who were on an eSports team, they're earning a varsity letter, winning a state championship, hoisting the same trophy as a traditional sport like football or basketball," Chapman says.

Esports is more than just a game. It teaches "the same lessons you get in traditional sports. You think about things like teamwork, communication, resilience, perseverance, goal setting, being able to shift strategy in the middle of a competition," Chapman explains — skills that help students excel both in school and in their future careers.

On the business side, Chapman shares his vision of how PlayVS is working to expand revenue opportunities within the esports ecosystem, from streaming and NIL (Name, Image, and Likeness) deals to inspiring kids to pursue careers in STEM. Esports, Chapman argues, is not only a gateway to gaming careers but also a stepping stone to technical and lucrative fields many young gamers may have never considered.

Thoughts? Questions? Fan mail? Email us at [email protected]

"Financial Freestyle with Ross Mac" on Yahoo Finance was created by John Tejada, and this episode was produced by Rachael Lewis-Krisky.

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Buying a home is one of the most significant decisions in a person's life. It's usually the largest purchase you'll make and involves a long-term commitment, so it's important to get it right.

Vishal Garg, founder and CEO of Better.com, joins this week's episode of Financial Freestyle with Ross Mac to discuss how his company is streamlining the mortgage process and what buyers should consider when purchasing a home.

Like many entrepreneurial ventures, Better.com started with a personal pain point. "I started Better.com because I went through the mortgage process with my wife... we were successful finance professionals, and we were like, 'This is so complicated,' like, 'How do I get pre-approved?'" recalls Garg.

A decade later, Garg is leading his mortgage company with backing from some of the world's largest investors, including Goldman Sachs and Kleiner Perkins.

Financial Freestyle with Ross Mac" on Yahoo Finance strives for economic prosperity for all. Through expert insights, actionable advice, and inspiring success stories, we empower you to build and accelerate wealth. Join us on a transformative journey towards financial freedom and inclusive economic growth.

Thoughts? Questions? Fan mail? Email us at [email protected]

"Financial Freestyle with Ross Mac" on Yahoo Finance was created and produced by John Tejada.

Learn more about your ad choices. Visit megaphone.fm/adchoices

Everyone encounters debt at some point. It’s important to deal with it as soon as possible, or it can balloon into an unmanageable problem.

John and David Auten-Schneider, hosts of Yahoo Finance’s Living Not So Fabulously, know this problem all too well. They join this week’s episode of Financial Freestyle with Ross Mac to share their experience with debit, the psychological side of why we spend, and what they did to dig themselves out of debt once and for all.

"Financial Freestyle with Ross Mac" on Yahoo Finance strives for economic prosperity for all. Through expert insights, actionable advice, and inspiring success stories, we empower you to build and accelerate wealth. Join us on a transformative journey towards financial freedom and inclusive economic growth.

Thoughts? Questions? Fan mail? Email us at [email protected]

"Financial Freestyle with Ross Mac" on Yahoo Finance was created and produced by John Tejada.

Learn more about your ad choices. Visit megaphone.fm/adchoices

The assist is one of the most underrated statistics in basketball, yet it’s essential for scoring buckets.

Former second-round NBA Draft pick Evan Turner understands this well and plans to apply his playmaking skills to the business world.

Turner, an NBA veteran who spent a decade in the league, joins Financial Freestyle with Ross Mac this week to discuss how he's translating his on-court experience into business success.

"Financial Freestyle with Ross Mac" on Yahoo Finance strives for economic prosperity for all. Through expert insights, actionable advice, and inspiring success stories, we empower you to build and accelerate wealth. Join us on a transformative journey towards financial freedom and inclusive economic growth.

Thoughts? Questions? Fan mail? Email us at [email protected].

"Financial Freestyle with Ross Mac" on Yahoo Finance was created and produced by John Tejada.

Learn more about your ad choices. Visit megaphone.fm/adchoices