Our Cake and Eat It Too

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

• Share with someone who would benefit, like and subscribe to hear all of our future episodes!

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/

Chapters

• (00:00:00) - Off-Site Podcast: When You Should Have Started a Business
• (00:00:45) - Steve Jobs on Working in the Summer
• (00:01:33) - On The Drop Off of Kids
• (00:04:25) - Coming soon: The Balance Between Work and Family
• (00:08:31) - How We're Redoing Our Minutes Onboarding
• (00:13:46) - The Secret to Good Trials
• (00:15:29) - The Value of Out-Of-Office Training
• (00:18:44) - How to Start a Business With a Baby
• (00:20:39) - Management Persona 6: Stories for Collaboration
• (00:25:22) - Reasons We're Optimizing Pricing
• (00:31:31) - What Is the Leverage of Your Business?
• (00:35:27) - Are You Still Using Agents in Your Sales?
• (00:37:32) - The Percentage of AI Pilots Are Failing
• (00:39:17) - What is an AI Agent?
• (00:40:46) - Pilots: The Need to Connect With Your Team
• (00:44:40) - Initiating AI in the Workforce
• (00:47:45) - Reaching Out to Your Customers
• (00:52:28) - How to Build a Million-Revenue Startup with a Marketing Plan
• (00:57:05) - Separation of Marketing and Integrations