Enthusiastic Life | with Brendan Walsh

Ep 38 — Josh Gershonowicz: What Happens After You Sell Your Company?

• Brendan Walsh

Share episode

Use Left/Right to seek, Home/End to jump to start or end. Hold shift to jump forward or backward.

0:00 | 34:38

In Episode 38, Brendan sits down with Josh Gershonowicz, founder, entrepreneur, and advertising executive, for a candid conversation about life, business, and what comes after success.

Josh shares his journey building a company in the advertising industry, growing it over time, and ultimately making the decision to sell. But what makes this conversation especially compelling is what comes next — the often unspoken reality of what life feels like the day after a major exit.

They dive into the emotional and mental side of transitioning out of something you’ve built, the identity shift that comes with it, and how success doesn’t always feel the way you expect it to.

Beyond business, the conversation explores family, personal growth, and Josh’s connection to Detroit — including his work and vision for the Milwaukee Junction neighborhood, as well as his new venture, Shortlist.

This episode is about ambition, identity, and navigating what comes after you reach a major milestone.

In this episode, we cover:

  •  Josh’s journey as a founder in the advertising industry 
  •  What it takes to grow and sell a business 
  •  What the day after selling a company actually feels like 
  •  The mental and emotional impact of an exit 
  •  Identity shifts after success 
  •  Family, life, and personal priorities 
  •  His connection to Detroit and the Milwaukee Junction neighborhood 
  •  His new venture, Shortlist 

🔗 Learn more about Shortlist:

🌐 https://getshortlist.co/

🎙 The Enthusiastic Life Podcast

Hosted by Brendan Walsh
Produced by Ryan Dewan, Wave Media

📲 Instagram → https://www.instagram.com/enthusiasticlifepod
📲 Facebook → https://www.facebook.com/enthusiasticlifepod

🎧 Available on Spotify, Apple Podcasts, YouTube & all major platforms