Offsite

About Offsite

The Offsite Podcast is a candid, behind-the-scenes catch-up with host Jordan Gal and the friends, founders, and thinkers he admires. Each episode kicks off with real talk about work—what’s hard, what’s going well, and what’s unfolding in the moment. But just as important is what’s going on outside the lines of work: personal growth, ambition, envy, burnout, and the chaos of building while being human. With a rotating cast of co-hosts, the show is as much about chemistry as it is about insight. This is a podcast about making sense of the mess and meaning of modern work and life, without taking ourselves too seriously. Honest updates, sharp takes, and the occasional therapy session, all recorded with a mic, a laugh, and a glass of something nearby. Brought to you by Rosie, the AI-powered phone answering service for small businesses.

Publisher

Jordan Gal

Category

business · leisure · news

Language

en

Explicit

No

First episode

25 Jun 2025

Latest episode

8 Jan 2026

Latest episodes

10 of 16 episodes have a transcript.

1. 

   8 Jan 2026TRANSCRIPT

   Ep 16: Bootstrapped Web Update

   Host Jordan Gal interviews Brian Casel of Builder Methods about scaling bootstrapped businesses by diversifying growth strategies and leveraging content effectively.

2. 

   19 Nov 2025TRANSCRIPT

   Ep 15 - Strategy Session

   Host Jordan Gal interviews Ruben Gamez, founder of SignWell, about SaaS pricing strategies, the friction paradox, and navigating market disruptions.

3. 

   12 Nov 2025TRANSCRIPT

   Ep 14 - Culture Shock

   Host Jordan Gal interviews Jon Ewalt, founder of Roaster Tools, about building a business aligned with personal values and navigating mid-life entrepreneurship.

4. 

   5 Nov 2025TRANSCRIPT

   Ep 13 - Set the Mood

   Host Jordan Gal interviews Craig Hewitt and Chris Gimmer about selling business outcomes over AI solutions and the future of AI and robotics.

5. 

   29 Oct 2025TRANSCRIPT

   Envy Fuel

   Host Jordan Gal interviews software engineer and entrepreneur Christian Genco about how sharing vulnerability, like being fired, creates unexpected business opportunities and protects engineering focus.

6. 

   22 Oct 2025TRANSCRIPT

   Two Different Approaches

   Host Jordan Gal interviews Jesse Hanley, founder of Bento, exploring their contrasting entrepreneurial journeys and strategies for building successful businesses.

7. 

   24 Sept 2025TRANSCRIPT

   Our Cake and Eat It Too

   Host Jordan Gal interviews CEO Henry Poydar about navigating entrepreneurial transitions and the pursuit of family flexibility.

8. 

   18 Sept 2025TRANSCRIPT

   Get Some Sleep

   Host Jordan Gal interviews entrepreneur Christian Genco about optimizing personal performance and leveraging AI for business success, including Genco's breakthrough with sleep onset insomnia.

9. 

   10 Sept 2025TRANSCRIPT

   Good Stress

   Host Jordan Gal interviews Craig Hewitt, founder of Castos, about navigating entrepreneurial stress and competition through AI-driven distribution strategies and his "100 Days of AI" experiment.

10. 

    27 Aug 2025TRANSCRIPT

    Bootstrapped Web Update

    Jordan Gal interviews Brian Casel about scaling SaaS businesses, navigating advertising pitfalls, and embracing a creator-first approach with AI.

11. 

    6 Aug 2025

    "Drop In" Jesse Schoberg of Drop-In Blog

    Host Jordan Gal interviews entrepreneur Jesse Schoberg about transitioning from a bootstrap mentality to enterprise sales and overcoming growth plateaus.

12. 

    23 Jul 2025

    From 200 Employees to Questioning Your Purpose - The Post-Exit Reality

    Host Jordan Gal interviews Assaf Gal, who recently sold his 200-employee fitness franchise empire, about the emotional post-exit reality and the search for new purpose.

13. 

    16 Jul 2025

    The American Wolf

    Host Jordan Gal interviews entrepreneur Christian Genco about the internal conflict founders face between ambition and contentment, offering insights into entrepreneurial psychology and decision-making.

14. 

    9 Jul 2025

    Nothing Works

    Host Jordan Gal interviews Christopher Gimmer and Craig Hewitt about the ineffectiveness of traditional SEO and content marketing, and they explore AI's role in customer acquisition and lead generation.

15. 

    2 Jul 2025

    Talk Story with Henry Poydar - AI and Authentic Leadership

    Serial entrepreneur Henry Poydar discusses with host Jordan Gal the crucial role of authentic storytelling for entrepreneurs, especially when scaling their message across personal, investor, and sales narratives in this interview.

16. 

    25 Jun 2025

    Zero Percent Concerned

    Host Jordan Gal interviews Rob Walling and Aaron Francis, who share insights on balancing authenticity with effective marketing and navigating the psychological challenges of entrepreneurship.

Inside a recent episode

Ep 16: Bootstrapped Web Update

Published 8 Jan 2026 · Transcript excerpt

[…] You're not a entrepreneur. You are a professional builder. So one flavor of the demand is adaptation. So I've been hand coding my whole career. I'm a full stack developer or I'm a back end developer or I'm a front end person. And I've always done it by hand. But now that we have cloud code and now that these things are actually getting really good, I need to not only, it's simple enough to just learn how the tools work. You can figure out pretty easily like how to use cloud code. What I think most developers are need is like, yeah, but how is this changing our workflow? How are we thinking differently about our process? […]

Who has been a guest on Offsite

Names identified in recent episode analyses. Showing up to five guests.

• Brian Casel
• Ruben Gamez
• Jon Ewalt
• Craig Hewitt
• Chris Gimmer

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

YouTube views

13,193

Score snapshot 15 Sept 2025

Podcast Authority Score: 47 / 100

A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.

Quality

66

Social presence

0

YouTube

72

Engagement

0

Contact Offsite

Guest appearances

Books guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.

Questions about Offsite