Aspire with Emma Grede — Detailed Summary

Episode: What Growing Up in Chaos Actually Teaches You

Guest: Rich Kleiman
Host: Emma Grede
Release Date: March 17, 2026
Podcast: Aspire with Emma Grede (Audacy)

Main Theme

This episode explores how trauma and chaos in childhood can shape, empower, and even become superpowers in adulthood, particularly in business and leadership. Emma Grede interviews longtime friend and industry leader Rich Kleiman, tracing his journey from a volatile upbringing through a winding entrepreneurial path to his success as Kevin Durant’s business partner and the founder of Boardroom.

Key Discussion Points & Insights

1. Rich’s Background and Path to Success

• Introduction & Current Work ([03:41–05:13])

  • Rich is founder of Boardroom, a media company at the intersection of sports, music, tech, and culture, and co-founder of 35 Ventures, the family office/holdco for himself and Kevin Durant.
  • Manages all business, philanthropic, and investment arms for Durant, plus acts as his agent.

• Early Hustle & Link Between Passions ([05:31–07:18])

  • Childhood fascination with multiple cultures: hip hop, basketball, New York nightlife. Always wanted to be in influential rooms.
  • Launched his first “business” at 7, showing an early drive for entrepreneurship and connection.

• First Professional Breaks ([07:38–09:32])

  • Early break came with help from Mark Ronson. Emma reflects on Rich’s generosity and continual support in those years.

2. Growing Up in Chaos: Family & Formative Years

• Family Dynamics ([09:57–12:18])

  • Upper West Side NYC, middle-class upbringing, private school but emotionally unstable home.
  • Describes home as “volatile” — constant fighting, mother was erratic, sometimes vicious.
  • After parents’ divorce, mother spiraled into addiction, neglect; Rich lacked adult guidance or supervision.

• Coping Strategies ([12:18–14:40])

  • Existed in two lives: chaos at home, social and outgoing persona outside.
  • Academic achievement not prioritized; hustled and socialized as survival mechanisms.

Quote:
"My ability still to this day to navigate through chaos...my heart doesn’t skip a beat. My brain doesn’t start spinning from chaos anymore. If anything, I know I’m the right person to navigate through chaos...And there’s a level of empathy that I live with still to this day that allows me to manage situations."
— Rich [14:40]

3. From Chaos to Superpower: Empathy & Leadership

• Emma’s Reflection ([16:01–17:19])

  • Emma reframes trauma as a source of superpowers—hyper-awareness, deep empathy, calm under pressure.

• “Doing the Work” & Growing Up Fast ([17:19–18:18])

  • Rich shares about “doing the work” after leaving home—party lifestyle in college, hustle as a campus bookie.

4. College Hustle & First Anxiety Battle

• Life as a College Bookie ([18:18–24:38])

  • Became a bookie in Boston—first real business, learned P&L, profiling people, managing risk/collections.
  • Amassed $275,000 before being kicked out for lack of academic engagement.

• Anxiety & Mental Health ([19:51–23:17])

  • Struggled with severe anxiety attacks—rare at the time, especially for men to discuss.
  • Learned to seek and accept help, talk openly about struggles.

Quote:
"If I hid that, I was gonna die honestly, straight up…if I keep this to me, it’s not gonna get from me. So I just kept it 100 with everybody around me, with a smile…I talked about it, I laughed about it with everybody."
— Rich [20:44]

5. Navigating Through Life with Hustle & Connections

• Transition to Music & Media ([24:38–32:51])

  • After a failed college stint and wandering, got offered to help launch a hip hop website in 1999 (precursor in concept to Boardroom).
  • Early lessons: creating community, brand building, networking with future stars and industry leaders.
  • Landed first real media production gig through being in the right rooms, leveraging network.

• Fearlessness Born from Chaos ([30:28–31:14])

  • Lack of parental guidance and constant “real” fears as a child made business risks seem comparatively minor.

Quote:
"No blueprint, no game plan, no rule book, no guardrails…For me, I was just like, this is fun. Like, straight up, this is fun."
— Rich [30:33]

6. Relationship Building as Currency

• Proximity & Diverse Networks ([32:51–34:15])

  • Values being able to navigate a diversity of circles, connect genuinely, never relying on “the pitch,” but on trust and contribution.
  • Proximity to power leveraged respectfully, with an eye toward bigger goals.

• Validation and Insecurity ([34:15–37:41])

  • Acknowledges ongoing insecurities from lack of validation in early life. Outward perception didn’t always match internal struggle.
  • Constantly measured personal achievement against personal potential, not public praise.

7. Mother’s Legacy & Closure

• Complex Relationship & End of Life ([37:42–41:48])
  • Mother never recovered; supported her financially but had to cut off close contact for family’s wellbeing.
  • Found closure only after her death, by being able to talk to her unopposed for the first time.

Quote:
"I said to her, 'I know somewhere deep down inside, you did your best, and, like, you didn’t want this, and I do know you loved me…This is the first time she’s ever not interrupted me when I was talking.'"
— Rich [39:07]

• Impact on Own Parenting ([41:57–45:44])
  • Pledges unconditional love/support to his own daughters; talks openly and provides security he never had.
  • Actively works to avoid repeating cycles of trauma.

Emma’s Reflection:
"You eclipse the curse…what you’ve done…not just becoming successful, but having this incredibly successful family when you had absolutely no basis…that’s the most successful thing that could possibly happen."
— Emma [44:38]

8. Climbing in the Industry: Roc Nation, Entrepreneurship, and Growth

• Roc Nation Experience ([50:05–53:51])

  • Gained structure, validation, and business skills; acknowledges he was emotional and less professionally equipped at the time.
  • Chaos from family life bled into work, but was motivated by the desire for regard and lasting impact.

• Choosing Growth Over Comfort ([55:53–58:35])

  • Observed that some peers were “unicorns” (Zuckerberg, Jay Z), but for most, improvement is about deliberate skill-building and self-awareness.
  • Prioritizes telling himself the truth about where he is and wants to go.

9. Breaking Through: Sports Management & Partnership with Kevin Durant

• Pivot to Sports & Meeting Durant ([59:50–63:08])
  • Transitioned to sports, found “his world” when managing athletes, notably Kevin Durant.
  • Partnership with Durant based on mutual trust and unconventional thinking; didn’t follow traditional agent path.

Quote:
"He [Kevin Durant] let go of other agents…They may have said, yeah, I understand why you’re hanging with you, he’s a lovely man…can’t be your guy. He didn’t care. From day one. And because of that, I always feel responsible for him in every way, shape, or form. He gave me this wind at my sails that I don’t think I had ever had."
— Rich [63:39]

10. Business Philosophy: Simplicity and Adaptation

• Advice for Entrepreneurs ([66:10–67:03])

  • Advocates simplifying everything down to fundamentals; once the core is solid, you can experiment.
  • Stresses the importance of building trust and “getting reps” in partnerships.

• Business Learnings from Tech Investing ([67:46–69:16])

  • Early investments in Silicon Valley provided invaluable education and connections.
  • Believes hands-on experience and learning from founders were like “his college.”

11. Leadership & Organizational Culture

• Evolution as a Leader ([75:19–76:50])
  • Kindness and respect for employees’ whole lives are non-negotiable.
  • Learned to make harder, sometimes unpopular decisions as part of scaling a business.

Quote:
_"You have empathy. That comes from experience…When your whole career is built on being liked…to be able to make really harsh, cold decisions…was a little bit of a challenge for me."
— Rich [76:53]

• Gender Differences at Work ([78:28–79:50])
  • Observes women generally work harder than men, but move up more slowly—a reflection, he says, of societal structure.

12. Money Mindset and Legacy

• Relationship to Money ([80:06–82:12])

  • Childhood conflict and anxiety around money made him strive for financial security and value his work.
  • Embraces advice to “charge double”: knowing your worth brings more opportunities.

• Most Expensive Lesson ([83:44–84:19])

  • Losing everything he’d earned as a bookie/gambler, realizing the importance of valuing earnings and managing wisely.

• On Risk ([84:27–84:46])

  • Early years marked by risk-taking and confidence that “I’ll figure it out next week” if things didn’t work out.

13. Legacy, Growth, and Ultimate Aspirations

• Still Proving Himself ([85:02–86:20])

  • Feels immense pride in climbing out of a “broken” situation but continues to strive for more—for himself and his family.

• Evolving as a Person ([86:20–87:22])

  • Seeks continual self-improvement, not just in business, but as a parent, partner, leader, and individual.

• Goals for the Future ([88:01–90:00])

  • For 35V (Durant’s vehicle): Building lasting opportunity and generational wealth for Durant and his legacy.
  • For Boardroom: Create a media institution comparable to Vogue or Forbes—an enduring, recognizable brand at the intersection of sport, culture, and tech.

Quote:
"I want something that lasts...And maybe I’m naive…but that’s what motivates me."
— Rich [89:39]

Notable Quotes & Memorable Moments (Selected with Timestamps)

• “I was just like, this is fun. Like, straight up, this is fun.” — Rich ([30:57])
• “My heart doesn’t ever race…my brain doesn’t start spinning from chaos anymore…I'm the right person to navigate through chaos…” — Rich ([14:40])
• "You can either transform [trauma], create an entirely different legacy...or it stays with you and it destroys you." — Emma ([44:38])
• “He gave me this wind at my sails that I don’t think I had ever had.” — Rich, about Kevin Durant ([63:49])
• “As long as I don’t have to ever stress money and my family doesn’t...I’ll be happy.” — Rich ([81:08])
• "Patience." — Rich (underrated business skill) ([90:16])
• “Right now, I really want to figure out how to be best friends with my daughters...” — Rich ([92:05])

Important Segment Timestamps

• [04:27] — Rich’s current position; Boardroom and 35 Ventures explained
• [09:57] — Rich’s early family chaos: parental conflict, mother’s addiction
• [14:40] — Impact of childhood trauma on adult resilience and empathy
• [18:17] — Becoming a bookie in Boston: hustle and lessons in business
• [20:22] — First breakthrough anxiety attack; openness with mental health
• [24:38] — The transition from college dropout to music business entry
• [32:51] — Observing mentors, building currency in networks
• [37:42] — Relationship (and closure) with mother’s decline and passing
• [41:58] — Becoming the parent he wished he had; breaking the cycle
• [50:05] — Building career in music: Roc Nation and professional growth
• [63:08] — The unique partnership with Kevin Durant and approach to business
• [66:10] — Rich’s advice: Simplifying problems as a leadership tactic
• [75:19] — Leadership philosophy: kindness, respect, overcoming people-pleasing
• [78:28] — Observations on working women vs men in business
• [80:06] — Money in childhood versus adult relationship to earning
• [90:16] — Rapid fire: "Patience" as most underrated business skill
• [92:05] — Most current aspiration: keeping close with his daughters

Takeaways for Listeners

• Transforming Trauma: Chaotic, traumatic childhoods can breed resilience, adaptability, and empathy—superpowers in business if processed appropriately.
• Networking with Purpose: Building real, diverse connections (not just “networking” for gain) is an invaluable asset.
• Leadership is Kindness Plus Courage: Effective leaders merge empathy with the courage to make difficult, sometimes unpopular decisions.
• Self-Worth and Value: Know your worth and don’t be afraid to claim it; surround yourself with people who challenge you to do so.
• Run Your Race: Life isn’t a competition. Determine your own timeline, define your own version of success, and focus on personal growth.
• Legacy Matters: Building something that outlasts you—be it a family culture or a business—is a core motivator for true entrepreneurs.

Further Listening/Reading

• Books Mentioned: The War of Art ([90:50])
• Key Business Mantras: Simplicity, continuous evolution, empathy-driven leadership

Summary Tone

Both Emma and Rich are candid, introspective, and occasionally humorous. The conversation is emotional, raw at times, with mutual generosity of spirit and an emphasis on real-world, hard-earned advice. The episode is a testament to resilience, the complexity of personal growth, and the power of relationships—at home and in business.