What price are entrepreneurs willing to pay for presence?

Jordan Gal, founder and host of Offsite, reconnects with Henry Poydar, CEO of Steady, to discuss the personal and professional transitions of being an empty nester entrepreneur. Henry, who recently dropped off his twin boys at college, reflects on the emotional journey while pivoting Steady from a per-user pricing model to team-based pricing for their AI copilot for teamwork. "You get 18 summers with your kids, and then it's over," Henry shares about the transition. The conversation explores how both founders chose entrepreneurship precisely for family flexibility, with Jordan questioning whether true work-life balance exists or if it's about accepting trade-offs.

In This Episode:

(00:00) Empty Nester Entrepreneur Reality

(05:53) The Entrepreneurial Path to Family Balance

(08:25) Trading Career Greatness for Presence

(12:05) Rosie's Seven-Day Trial Strategy Shift

(18:36) The Psychology of Phone Coverage

(25:21) Steady's Team-Based Pricing Revolution

(33:04) Building Customer Advisory Relationships

(42:59) Pilots vs Trials in Enterprise Sales

(54:02) SimpliSafe Marketing Masterclass

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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:
Henry Poydar Twitter: https://x.com/henrypoydar
Steady AI: https://steady.app
Tiny Seed accelerator: https://tinyseed.com
MicroConf conference: https://microconf.com
Jordan Gal: https://www.linkedin.com/in/jordangal/
Rosie AI: https://heyrosie.com/

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