Five Hardest Questions Podcast with Dr. Greg Ellison II

Fivehardestquestionspodcast
  • 5.0 (6)
  • Self-Improvement
  • Updated Daily

A podcast about the five hardest questions we all have to answer at some point in life.

Episodes

  1. Jun 5

    Succession Feat. Gregory C. Ellison III | Episode 006 | Five Hardest Questions Podcast

    Welcome to the newest episode of Five Hardest Questions, where bold conversations meet fearless truth. This episode G2 meets G3 on camera for a spirited conversation on purpose, parenthood, legacy and passion. Dr. Greg sits down to interview his son, Gregory Ellison III, and these hard questions were like no other. Throughout the conversation you can feel Dr. Greg grappling with the growth and respect his son exudes while also reconciling that he's no longer the little boy asking him to stay home from work trips. An amazing journey, take it wish us.🔔 Subscribe for more episodes of Five Hardest Questions across audio, video, and social platforms.💬 Share your thoughts in the comments. #FiveHardestQuestions #TayariJones #Kinfolk #PodcastPremiere #BlackVoices #Storytelling #Culture #Community

  2. May 27

    The Cost Of Freedom feat. René August | Episode 005 | Five Hardest Questions Podcast

    Welcome to the newest episode of Five Hardest Questions, where bold conversations meet fearless truth. In this week’s episode, Dr. Greg Ellison II and Okorie “OkCello” Johnson sit down with Rev. René August — South African anti-apartheid freedom fighter, pastor, global peacebuilder, and protégé of Archbishop Desmond Tutu. A lifelong advocate for justice, reconciliation, and moral courage, Rev. August brings a wisdom forged through resistance, faith, sacrifice, and the ongoing pursuit of human dignity. Born and raised in South Africa during apartheid, Rev. August dedicated her life to confronting systems of oppression while helping communities imagine healing beyond violence. Her journey from activist to spiritual leader reflects a deep commitment to truth-telling, compassion, and collective liberation. Through her work alongside Archbishop Tutu and global movements for justice, she has become a powerful voice on forgiveness, accountability, and the responsibility of memory. Through five probing questions, this conversation explores: 
• What it means to fight for freedom without losing your humanity 
• The spiritual cost of oppression and resistance 
• Forgiveness as both burden and liberation 
• The relationship between faith, justice, and moral imagination 
• How generations carry both trauma and hope This is more than an interview. It is a meditation on courage, healing, and the unfinished work of freedom. 🔔 Subscribe for more episodes of Five Hardest Questions across audio, video, and social platforms. 💬 Share your thoughts in the comments. What does “kinfolk” mean to you? #FiveHardestQuestions #TayariJones #Kinfolk #PodcastPremiere #BlackVoices #Storytelling #Culture #Community

  3. May 14

    The Unusual Season | Episode 004 | Five Hardest Questions Podcast

    Welcome to the newest episode of Five Hardest Questions, where bold conversations meet fearless truth. In Episode 4, Dr, Greg gives you the insight into an unusual season in his life. And how that can apply to your own personal season, This episode is sponsored by the AJ Terrell Foundation. 🔔 Subscribe for more episodes of Five Hardest Questions across audio, video, and social platforms. 💬 Share your thoughts in the comments. What does “kinfolk” mean to you? #FiveHardestQuestions #TayariJones #Kinfolk #PodcastPremiere #BlackVoices #Storytelling #Culture #Community

  4. May 6

    Uncle Tony feat Tony Alonso | Episode 003 | Five Hardest Questions

    Welcome to the newest episode of Five Hardest Questions, where bold conversations meet fearless truth. In Episode 3, “Uncle Tony”, Dr. Greg Ellison II and Okorie "Okcello" Johnson sit down with Grammy-nominated pianist, composer, and creative visionary Tony Alonso, who Greg affectionately calls his "Uncle Tony. Tony Alonso's work blends musical excellence with emotional storytelling. Known for his dynamic performances and genre-crossing artistry, Alonso has built a reputation for creating music that moves audiences beyond entertainment and into reflection. His journey through music, faith, culture, and creativity has positioned him as a respected voice both on and off the stage. With a career rooted in discipline, innovation, and authenticity, Tony continues to inspire through every note he plays. 🔔 Subscribe for more episodes of Five Hardest Questions across audio, video, and social platforms. 💬 Share your thoughts in the comments. What does “kinfolk” mean to you? #FiveHardestQuestions #TayariJones #Kinfolk #PodcastPremiere #BlackVoices #Storytelling #Culture #Community

  5. Apr 29

    Titan featuring Dr. Milton Jones Jr. | Episode 002 | Five Hardest Questions

    Welcome to the second episode of Five Hardest Questions, where bold conversations meet fearless truth. In Episode 2, titled “Titan”, host Dr. Greg Ellison II sits down with titan of the banking industry, Dr. Milton Jones Jr. Dr. Milton H. Jones Jr. is a distinguished business leader, philanthropist, and nationally respected advocate for mentorship and economic empowerment. He currently serves as Chairman of the Board for the 100 Black Men of America, one of the nation’s largest volunteer-led organizations dedicated to developing young people and strengthening communities through mentorship, education, and leadership. With a career spanning more than three decades, Dr. Jones held senior executive roles at Bank of America, where he led major operational and regional initiatives across the country. His leadership in the corporate world has been matched by his deep commitment to service, including past roles as Chairman of the United Negro College Fund and the Atlanta Business League. The unique relationship of Mr. Jones and Greg's father, Greg Ellison Sr., provides a beautiful backdrop for questions that revolve around business and personal beliefs. 🔔 Subscribe for more episodes of Five Hardest Questions across audio, video, and social platforms. 💬 Share your thoughts in the comments. What does “kinfolk” mean to you? #FiveHardestQuestions #TayariJones #Kinfolk #PodcastPremiere #BlackVoices #Storytelling #Culture #Community

  6. Apr 22

    Kinfolk feat. Tayari Jones | Episode 001 | Five Hardest Questions Podcast

    Welcome to the debut episode of Five Hardest Questions, where bold conversations meet fearless truth. In Episode 1, titled “Kinfolk,” host Dr. Greg Ellison II sits down with acclaimed author Tayari Jones, recently named one of TIME 100’s most influential people in the world. Together, they explore the layered meaning of “kinfolk,” not simply as family, but as identity, responsibility, community, and legacy. Through five probing questions, this conversation moves beyond surface-level dialogue into spaces where truth, vulnerability, and cultural insight meet. Expect a powerful exchange on: • The weight and wonder of belonging • Storytelling as both mirror and bridge • Navigating success while staying rooted • The tension between public recognition and private truth • What it really means to carry your people with you This is more than an interview. It is an invitation to reflect on who we are, where we come from, and who we are becoming. 🔔 Subscribe for more episodes of Five Hardest Questions across audio, video, and social platforms. 💬 Share your thoughts in the comments. What does “kinfolk” mean to you? #FiveHardestQuestions #TayariJones #Kinfolk #PodcastPremiere #BlackVoices #Storytelling #Culture #Community

    Kinfolk feat. Tayari Jones | Episode 001 | Five Hardest Questions Podcast
  • 6 Episodes

Ratings & Reviews

5
out of 5
6 Ratings

About

A podcast about the five hardest questions we all have to answer at some point in life.

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