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Startup DadAdam Fishman (author of a top business newsletter on Substack with 11K subscribers) interviews executives, entrepreneurs, and company leaders in technology companies who are also fathers. Author: Adam Fishman
Adam Fishman (author of a top business newsletter on Substack with 11K subscribers) interviews executives, entrepreneurs, and company leaders in technology companies who are also fathers. They discuss the tough aspects of work, parenting, family, the mistakes made and lessons learned along the way. All episodes at www.startupdadpod.com. Language: en Genres: Kids & Family, Parenting, Technology Contact email: Get it Feed URL: Get it iTunes ID: Get it |
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Family First Is Harder Than It Sounds | Jesse Rendall (Dad of 5, Sweater Ventures)
Thursday, 26 March, 2026
Jesse Randall is the founder and CEO of Sweater, a company making venture investing accessible to anyone with a smartphone. He is also a husband and father of five kids, ranging from 7 to 17 years old. In this conversation, Jesse shares how he thinks about balancing ambition, marriage, and fatherhood without losing sight of what matters most. He talks about moving his family to Puerto Rico, why putting career above everything else can leave you miserable, and why dads need to be strong, caring, and fully engaged at home.Jesse also opens up about his parenting philosophy, including why he believes fathers should be authoritative first and friends second, how he and his wife use a no hint dropping rule to communicate better, and why both parents need something outside of work and family that is just for them. We also get into one of the most fascinating parts of the conversation, how Jesse is using AI to rethink his kids’ education and teach them how to think critically in a world where information is everywhere. We discussed: Moving a family to Puerto Rico: How Jesse approached a major family transition and helped his kids adapt to a completely new environment.The cost of putting career first: Why Jesse believes chasing professional success at the expense of family can leave you deeply unfulfilled.What strong fatherhood really looks like: Why dads need to be caring, present, emotionally grounded, and willing to lead at home.Better communication in marriage: The “no hint dropping” rule Jesse and his wife use to avoid passive-aggressive communication and say what they actually mean.Why parents need a third pillar: Jesse shares why both partners need something outside of work and family that helps them stay grounded and fulfilled.Rethinking education with AI: How Jesse is using AI to redesign his kids’ learning and teach them to think critically in a world full of instant information.Where to find Jesse RandallLinkedIn: https://www.linkedin.com/in/sweaterceo/ Sweater: https://www.sweaterventures.com/ Where to find Adam FishmanFishmanAF Newsletter: www.FishmanAFNewsletter.com LinkedIn: https://www.linkedin.com/in/adamjfishman/ Instagram: https://www.instagram.com/startupdadpod/ X: https://x.com/fishmanafIn this episode, we cover:(00:00) Welcoming Jesse Randall, founder and CEO of Sweater!(01:39) Why Jesse moved his family to Puerto Rico(03:09) Helping five kids adjust to a massive family move(05:16) Why putting career first can leave you miserable(09:41) The family and faith values that shaped Jesse(13:53) Preparing kids for a world changed by AI(16:31) What it means to be a strong and present dad(24:21) Why every parent needs something outside work and family(28:32) Endurance sports, headspace, and staying grounded(32:17) Why dads should be authoritative first and friends second(35:43) The “No hint-dropping” rule that changed their marriage(39:54) Why clear communication matters with kids too(43:29) How Jesse is rethinking education with AI(53:30) The biggest surprise after 17 years of fatherhood(57:46) Lightning round: Parenting philosophy, family rhythms, and what matters mostResources From This Episode:Sweater Ventures: https://www.sweaterventures.com/ Ball Floater (Toy): https://a.co/d/04uaYZ3C The Emperor's New Groove: https://www.imdb.com/title/tt0120917/ Dumb and Dumber: https://www.imdb.com/title/tt0109686/ Ford Expedition: https://www.ford.com/suvs/expedition/ —Support Startup DadFor sponsorship inquiries, email: podcast@fishmana.com.For Startup Dad Merch: www.startupdadshop.com
