What matters after decades of building, losing, and rebuilding?

In this episode of KP Unpacked, KP Reddy turns 55, and Nick uses the milestone for a lightning round conversation exploring career highs, crushing losses, and the philosophy that's shaped three decades of entrepreneurship. From living in a truck eating 19-cent tuna to running a VC fund, KP reflects on the moments that actually stuck and why they weren't the trophy wins.

The conversation moves between tactical and existential. KP explains how Claude Cowork is now his nurse practitioner (drafting insurance appeals, scheduling appointments, analyzing x-rays), why he runs four Mac Studios doing different jobs while he unpacks office furniture, and why the future of CRM is taking people to lunch instead of data entry. But the deeper thread is about identity: why his worst fear (going back to zero) doesn't actually scare him, why his family has more confidence in him than he has in himself, and why the 2008 financial crisis validated the self-doubt that still drives him today.

Key topics covered:

• Why KP spent his 55th birthday at the DMV after his assistant cleared his calendar without asking
• How Claude became his healthcare coordinator and delivered better emotional support than his mom
• The blank slate moment after his first exit paying off the house and feeling peace, not accomplishment
• Living in a truck with sleeves of tuna and stolen mayo packets and why going back doesn't scare him
• The 2008 crisis, personal guarantees, and why losing everything validated his lack of confidence
• Why "celebrating small wins" is for people not building unicorns assume wins, magnify losses
• Vibe working: running four Mac Studios with Claude Cowork while doing manual labor he actually wants to do
• Why relationship-driven CRM beats software: take engineers to lunch after RFP meetings, not Salesforce data entry
• The manager vs. maker schedule and why KP operates at sprint speed with no please-and-thank-yous
• Morning meditation as leadership: visualizing every founder and team member's context before the workday
• Why one founder said "I can feel when you're praying for me" and what that reveals about leading mission-driven teams
• The 10-year goal isn't three private jets, it's building community where all LPs are former founders who exited and came back

If you're navigating what success looks like after the wins, trying to lead without micromanaging while operating at full speed, or wondering whether your worst-case scenario is actually that bad, this episode will reframe how you think about ambition, fear, and what matters most.

Listen now.

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