Offsite
Offsite
Podcast Description
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.
Podcast Insights
Content Themes
The podcast delves into themes like entrepreneurship, mental health, personal development, and the intricacies of startup culture. Episodes feature discussions on various topics such as balancing authenticity with marketing in 2025 and the human aspects of storytelling in business, providing listeners with relatable insights and actionable advice.
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.
What if charging upfront actually converts better than free trials for your product?
Jordan Gal sits down with Ruben Gamez, founder of SignWell and creator of BidSketch, for a tactical deep dive into SaaS fundamentals. Ruben built two successful products despite never finishing high school—a testament to execution over credentials. Should you charge upfront or offer free trials? The duo dissects data from both their companies, revealing counterintuitive truths about friction and conversion. “Everything that added friction… resulted in just more conversions later,” Ruben explains about BidSketch, while SignWell required the opposite approach. They explore the grinding reality of competing in crowded markets, Google’s AI disruption of SEO traffic, and Ruben’s current transition from operator to owner at his 15-person company. Real strategies, zero fluff. How do you make pricing decisions from confidence instead of fear?
In This Episode:
(00:00) Catching Up with Ruben Gamez
(02:34) Homeschooling in Portland: Academic Excellence vs Public School
(08:56) From BidSketch to SignWell: The Accidental Pivot
(12:22) Ignoring Advice: Why Ruben Built SignWell Anyway
(19:46) Google’s AI Disruption: The Future of SEO Traffic
(26:35) The Friction Paradox: When More Steps Increase Conversions
(30:47) Free Trials vs Freemium: What Actually Works
(43:11) Making Business Decisions from Confidence Not Fear
(46:58) Transitioning from CEO to Owner at SignWell
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About the Show
Jordan Gal, founder and CEO of Rosie AI, hosts the Offsite Podcast where he teams up with rotating entrepreneur friends to explore what’s happening in their work and beyond. After successfully building and selling CartHook, Jordan now leads a VC-backed company while sharing candid insights about the realities of startup life. The show combines real-time business updates with deeper conversations about founder psychology, growth strategies, and the personal side of entrepreneurship that rarely gets discussed publicly.
Resources:
Twitter/X: https://x.com/earthlingworks
SignWell: https://signwell.com
BidSketch: https://bidsketch.com
Rosie AI: https://heyrosie.com/
Disclaimer
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