Marriage, Money, and Managing the Startup Rollercoaster | Jordan Gal (Dad of 3, Rosie)

Author: Adam Fishman
Published: Thu 22 May 2025
Episode Link: https://share.transistor.fm/s/16507912

Jordan Gal is the CEO of Rosie, an AI answering service for small businesses. He’s also a five-time founder, husband, and dad to three daughters.

Born in Israel and raised in an immigrant entrepreneur household, Jordan shares how that upbringing shapes his parenting and how he and his wife work to combine their very different childhood experiences.

We discussed:

Talking to kids about money: How Jordan brings business lessons into everyday moments without oversharing or creating pressure.
Being family first in a startup world: Why Jordan sees business as a tool to support his real priorities.
Nudging kids toward ownership: The subtle ways he introduces the value of equity, risk, and autonomy.
Managing stress without passing it on: How Jordan handles emotional spillover and what he shares with his kids.
Modeling healthy conflict in marriage: Why he believes transparency and disagreement are both part of partnership.
Challenging assumptions through travel: How 18 months of nomadic living reshaped what his family needed and what they didn’t.

Where to find Jordan Gal

LinkedIn: https://www.linkedin.com/in/jordangal
X: https://x.com/jordangal
Rosie: https://heyrosie.com/

Where to find Adam Fishman

FishmanAF Newsletter: www.FishmanAFNewsletter.com
LinkedIn: https://www.linkedin.com/in/adamjfishman/
Instagram: https://www.instagram.com/startupdadpod/

In this episode, we cover:
(00:00) Introducing Jordan Gal
(01:59) Growing up in an immigrant entrepreneur household
(04:13) Leaving investment banking for freedom and risk
(05:54) Blending two very different parenting styles
(08:33) What being “extremely family first” really looks like
(11:49) Living nomadically with a toddler and a pack and play
(17:37) Why Jordan’s family left Portland for the Chicago suburbs
(23:14) Talking to kids about money in everyday situations
(28:05) Gently guiding kids toward entrepreneurship
(30:08) Managing startup stress without bringing it home
(36:47) Being honest with your partner about startup risk and tradeoffs
(48:01) Lightning round: minivans, Bee Movie, and doing the worm

Show references:
For sponsorship inquiries email: [email protected].
For Startup Dad Merch: www.startupdadshop.com

Links for Jordan Gal

Rosie: https://heyrosie.com

Aaron’s LI: https://www.linkedin.com/in/aarondfrancis/

Aaron Francis’ Episode: https://www.youtube.com/watch?v=SntR9LmO4oU

Dorit Lemel: https://en.wikipedia.org/wiki/Dorit_Kemsley

University of Michigan: https://umich.edu/

Harvard Business School:https://online.hbs.edu/

Kibbutz:https://www.britannica.com/topic/kibbutz

David Foster Wallace, This is Water: https://www.youtube.com/watch?v=DCbGM4mqEVw

Pack N Play: https://www.gracobaby.com/shop/home-and-gear/pack-n-play-playards

Marine Layer: https://www.marinelayer.com/