John Azar fled Syria at 16 in the middle of a civil war, arrived in Charlotte, North Carolina not speaking a word of English, and eventually built his way to an MBA in finance and a career in commercial real estate. Then came 2008. His first company collapsed with no clients, no money, and a brand new baby at home.

He rebuilt, more than once. Along the way, his own therapist gave him a label he still carries: toxic optimist. He believes, almost unshakably, in people's capacity to change, and he's had to learn what that belief costs him when the other person never actually does the work.

On this episode of FINE is a 4-Letter Word, John talks with Lori Saitz about what failure actually means once you separate the event from the emotion attached to it, why he believes mastery requires periods of genuine imbalance, and what he tells business leaders facing circumstances completely outside their control.

What You'll Take Away

• Why believing in people's inherent goodness can work against you, according to what John's own therapist told him
• Why failure is whatever you decide it is, and why the event itself is different from the emotion you attach to it
• What John did in 2008 with no clients, no money, and a newborn at home, and what it teaches about controlling only what's actually yours to control
• Why sometimes the answer isn't what to add to your life, but what to stop doing
• Why mastery requires periods of genuine imbalance, and why that imbalance has to come in sustainable chunks rather than forever

Guest Bio

John Azar is a public speaker, coach, and founder. He speaks and coaches about entrepreneurship, resilience, and the myth surrounding balance and failure. He founded Peak15 Capital, a private equity firm specializing in commercial real estate, with talks drawing on two decades of deal-making, including work on a cumulative portfolio worth over $2 billion nationwide. Prior leadership roles at MACC Venture Partners and Boston Venture Partners, which he co-founded, round out his operating background, and he is also co-founder of Forja, an institutional-grade education and coaching ecosystem for commercial real estate investing and capital markets. He is a graduate of UNC Charlotte and Boston University's Questrom School of Business.

Chapters & Key Timestamps

01:25 The values he was raised with, and growing up the youngest of five in Syria

02:52 Growing up “raised by the wild,” and a childhood shaped by civil war

04:09 Immigrating to Charlotte, North Carolina at 16 with no English

05:32 The people who became his avatars: his father, brother, mother, and sisters

08:46 The term his therapist gave him: “toxic optimist”

10:53 Why failure is whatever you decide it is

14:14 His failed marriage, and what he's learned about facing himself

18:09 Building and closing multiple companies, including through the 2008 crisis

20:49 What to say to leaders facing circumstances completely outside their control

23:15 Commission and omission: sometimes the answer is what to stop doing

24:34 The daily practices that keep him grounded

25:00 Embracing imbalance as a requirement for mastery

31:04 The free diver metaphor: why imbalance has to come in chunks, not forever

32:27 The song that gets him going, and its unlikely origin

33:20 Where to find John: his coaching site and Peak 15 Capital

Resources Mentioned

• Company: Peak15 Capital — private equity firm specializing in commercial real estate
• Company: Forja — institutional-grade education and coaching ecosystem for CRE investing and capital markets, co-founded by John
• TV Show: Ballers (HBO) — the source of John's energy song
• Song: Right Above It by Lil Wayne and Drake — open.spotify.com/track/1kMuU3TNQvHbqvXCWBodmP

Connect With John Azar

Company: Peak15 Capital

Company: Forja

Website: johnazar.com

Website: peak15cap.com

LinkedIn: linkedin.com/in/jalalazar

Instagram: @jjazar

Email: azar@peak15cap.com

Continue With Lori

Website: zenrabbit.com

LinkedIn: https://www.linkedin.com/in/lorisaitz/

Email: Lori@ZenRabbit.com

Invitation From Lori

This episode is sponsored by Zen Rabbit. Trust is the foundation of all great workplaces, and in today's hybrid, fast-moving work culture, it's built through consistent, clear, human communication.

Quarterly town halls, Slack messages, or team-building events are rarely enough to create the connection employees need. That's why forward-thinking companies are hiring Lori to create internal and private podcasts that bring leaders and employees together through authentic stories and real conversations.

Think of it as the old-school company newsletter reinvented for the modern workplace.

If your company wants to strengthen communication, connection, community, and culture, connect with Lori at Lori@ZenRabbit.com or on LinkedIn: https://www.linkedin.com/in/lorisaitz/

Related Conversation

Episode 240: Amanda Van Der Heiden — on “win or learn,” her own reframe of failure that closely parallels John's view that failure is whatever you decide it is.

About FINE is a 4-Letter Word

FINE is a 4-Letter Word is the show for leaders who are tired of pretending everything is fine. We explore what it takes to lead with empathy, vulnerability, gratitude, and courage, especially during the seasons when life and leadership feel anything but fine. Listen for honest conversations about how human connection influences innovation, retention, leadership, and real impact. New episodes every week.

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