The Digible Dudes 217: EP218: The Hardest Part of Being a Founder (No One Talks About This!)

March 6, 2025
Digible Dudes Podcast

In this episode of the Digible Dudes podcast, co-founders David Staley and Reid Wicoff dive deep into the unspoken challenges every founder faces-from identity struggles and burnout to the difficult transition of stepping away from the business you built.

David shares his personal journey of leaving the day-to-day operations at Digible, the emotional toll of redefining purpose, and how his search for meaning led him to take on extreme adventures, including climbing Aconcagua and Ojos del Salado.

Key Discussion Points:

The Founder’s Dilemma: Why stepping away from your business is harder than it seems.
Burnout, Identity & Purpose: The mental and emotional challenges of leadership.
The Tony Robbins Approach: How coaching helped redefine priorities and balance.
Lessons from ‘Die With Zero’: How shifting focus from wealth accumulation to experiences changed everything.
From Hustle to Adventure: Why David is saying YES to extreme challenges—and what it’s teaching him about life.

Join David and Reid as they unpack the raw realities of entrepreneurship, self-discovery, and what it truly means to build a life beyond work. If you’ve ever felt burned out, lost, or unsure of your next move, this episode is for you.

Digible:⁠ https://digible.com/

Fiona: ⁠⁠⁠https://www.myfiona.com/

Leave a Spotify Review: ⁠⁠⁠https://spoti.fi/3LfoEdU⁠⁠⁠

Leave an Apple Review: ⁠⁠⁠https://apple.co/3AA2zRj⁠⁠

(00:00) The Struggles Every Founder Faces

(04:31) The Harvard Study: Only 20% of People Find Purpose

(07:02) How ‘Die With Zero’ Changed Our Perspective on Life

(10:07) The Founder’s Dilemma: Work vs. Life Balance

(12:43) Leaving the Business: The Emotional Toll of Letting Go

(16:09) Pushing Limits – Climbing Aconcagua & Ojos del Salado

(20:05) How Adventure Became My New Way of Life

(22:56) Can Purpose Be Selfish? The Truth About Fulfillment