Think a “portfolio career” makes family life chaotic? Ben argues the opposite.
In this special episode of Supra Insider, Ben shares a more personal side of his journey in a conversation originally recorded on the Startup Dad podcast with Adam Fishman.
From raising his daughter Gaia (with help from George, the family’s golden retriever) to navigating solo parenting in New York without nearby family, Ben opens up about the joys and challenges of fatherhood. He reflects on why a portfolio career actually feels more stable than a full-time job, how intentional routines have transformed his days, and the lessons learned from mistakes, community, and the chaos of parenting.
If you’re a parent balancing an ambitious career, curious about the realities of raising kids in a big city, or simply want to hear a more personal side of Ben outside of product leadership, this episode offers candid stories, practical takeaways, and a heartfelt look at family life.
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In this episode, we covered the following topics:
(01:47) George the golden retriever, Gaia’s favorite playmate, and the early days of parenting
(05:01) “Children will destroy your life and replace it with a better one” — reframing priorities
(08:30) How routines and compressed workdays reshape productivity as a parent
(09:53) Building a portfolio career with multiple income streams and why it feels more stable than full-time work
(22:25) Counterintuitive lessons from solo parenting and weekday vs. weekend dynamics
(29:22) Surprising joys of fatherhood and the sense of belonging it brings
(34:46) How structure and routines can be liberating rather than limiting
(45:43) Dad groups, community, and why parenting overlaps with relationship growth
(46:15) Technology, screens, and how the family navigates exposure for Gaia
(51:16) Lightning round: indispensable products, funniest bribes, chaotic mornings, and signature dad superpowers
And more!
Links:
Startup Dad Episode with Ben:
Startup Dad Podcast: https://www.startupdadpod.com/
Adam Fishman: https://www.linkedin.com/in/adamjfishman/
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