Marriage, Money, and Managing the Startup Rollercoaster | Jordan Gal (Dad of 3, Rosie)
This week on Startup Dad, we’re joined by Jordan Gal, CEO of Rosie and father of three daughters. Jordan shares how he’s working to build a healthier relationship with money, for himself and his kids.
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🎧 Listen now: Apple | Spotify | Youtube | Website 🎧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.
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Where to find Jordan Gal
LinkedIn: https://www.linkedin.com/in/jordangal
Rosie: https://heyrosie.com/
Where to find Adam Fishman
FishmanAF Newsletter: www.FishmanAFNewsletter.com
Instagram: https://www.instagram.com/startupdadpod/
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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:
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