Our Cake and Eat It Too

Sep 24, 2025

Henry Poydar, CEO of Steady and builder of an AI copilot for teamwork, shares insights on personal and professional transitions as an empty nester after dropping off his twins at college. He discusses the emotional journey of entrepreneurship and how it offers family flexibility. Henry dives into business strategies, advocating for team-based pricing over per-user models, and the importance of customer feedback in shaping products. He also shares innovative trial strategies to improve user engagement and highlights challenges in scaling AI tools for teamwork.

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ANECDOTE

Empty-Nester Moment

Henry Poydar cried when dropping his twin boys at college and called it a privilege.
He reflected that you get 18 summers with your kids and then that chapter ends.

INSIGHT

Entrepreneurship Bought Presence

Both guests chose entrepreneurship to create optionality and presence for family life.
That path still requires intense work but lets founders attend more family moments than many corporate roles.

INSIGHT

Balance Is A Trade-Off

Jordan admits career greatness and family presence are a trade-off, not a perfect 'cake and eat it too' scenario.
He now accepts giving up some career upside in exchange for family time.

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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/