Leading with Curiosity. A Podcast for Modern Leaders. podcast

Ep. 67: The Stand-Up CEO: What Comedy Teaches You About Leadership | Greg Hold

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What happens when a Wall Street CEO steps onto a stand-up comedy stage?


In this episode of Leading with Curiosity, host Nate Leslie sits down with Greg Hold, Founder and CEO of Hold Brothers Capital, to explore the surprising connection between business leadership and stand-up comedy.


With more than three decades in the finance industry and years of experience performing comedy, Greg shares how humor, confidence, persistence, and communication have shaped his professional and personal life. He reveals how the courageous art of comedy has sharpened his professional edge and emphasizes the strategic role of humor in the business world.


From managing a global business to refining jokes on stage, Greg explains why great leaders need to hire well, delegate effectively, embrace challenges, and focus on doing fewer things exceptionally well.


In this conversation, you'll discover:

• How stand-up comedy can improve confidence and communication

• What business leaders can learn from reading a room

• Why humor in the workplace requires care and judgment ("Every joke has a victim")

• How Greg develops and refines his comedy material

• Why hiring authentically and delegating are essential to business growth

• How to stay resilient and believe in yourself through difficult business cycles


Whether you're an entrepreneur, executive, business owner, or aspiring comedian, this conversation offers a powerful reminder to believe fiercely in your own vision and to embrace perseverance.


📌 CHAPTERS:

00:00 The Intersection of Comedy and Business

01:13 Greg Hold: 30-Year Finance CEO & Comedian

04:18 The Joke Writing Process vs. Business Strategy

07:43 Should You Be Funny at Work? (The Risks of Office Comedy)

11:41 The Secret to Building a Global Team: Hire Slowly

14:38 Navigating Business Crises and Surviving the Lows

18:40 Evolution vs. Stubbornness in Entrepreneurship

21:09 Connect with Greg Hold


🔗 CONNECT WITH GREG HOLD:

• Business: http://hold.com

• Comedy YouTube: https://www.youtube.com/@StandUpCEO

• Upcoming Shows: https://www.gregoryhold.com/calendar-comedy


📩 CONNECT WITH NATE LESLIE:

• Website: https://nateleslie.ca

• Business Contact: [email protected]


🎙️ ABOUT LEADING WITH CURIOSITY

Command and control leadership is dead. Nate Leslie interviews leaders, entrepreneurs, and executive coaches who challenge old paradigms and explore new approaches to leadership.


💬 JOIN THE CONVERSATION

How has a passion outside of work helped you become better at what you do? Share your thoughts in the comments!


#Leadership #Entrepreneurship #StandUpComedy #BusinessLeadership #LeadingWithCuriosity #GregHold #CEOAdvice

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