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Startup Dad

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.

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  • 23 episodes
  • weekly
  • Avg 1 hr 3 min
  • English

Episodes 23

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  • April 2 · 48 min

    New Dads: Stop Fighting The Change | Rex Gelb (Dad of 1, Summit Chase)

    Rex Gelb is the Founder/CEO of Summit Chase, a paid media agency serving B2B, SaaS, and professional services companies. Before starting Summit Chase, Rex spent more than 11 years at HubSpot, where he became the company’s Head of Paid Media. He’s also a husband and dad to a daughter who recently turned one. In this episode, Rex shares what it was like for both him and his wife to quit their jobs within 24 hours of each other right after parental leave, why that leap made sense for their family, and how becoming a dad has changed the way he thinks about ambition, hard work, and presence. We discussed: Leaving stable jobs right after parental leave: How Rex and his wife both quit their jobs within 24 hours of each other and why that felt like the right move for their family. The sooner you give up, the better: Why Rex believes fatherhood gets easier when you stop clinging to your old life and allow yourself to evolve into a new season. Fighting the “should gremlins”: How Rex thinks about the pressure to show up perfectly at work, at home, and for himself, and why letting go of impossible standards matters. Household systems that reduce friction: The shared notes, walking one-on-ones, and email threads Rex and his wife use to stay aligned and keep family life running smoothly. Using AI as a parenting tool: How Rex and his wife use monthly “leap alerts” with Gemini to stay on top of milestones, safety considerations, and what’s coming next for their daughter. Never deprive them of a struggle: Why Rex is already thinking about how to let his daughter work through challenges on her own so he can build confidence instead of accidentally undermining it. Where to find Rex Gelb LinkedIn: https://www.linkedin.com/in/rex-gelb-43445b1b/ Summit Chase: https://www.summitchase.co/ Where to find Adam Fishman FishmanAF Newsletter: www.FishmanAFNewsletter.com LinkedIn: https://www.linkedin.com/in/adamjfishman/ Instagram: https://www.instagram.com/startupdadpod/ X: https://x.com/fishmanaf In this episode, we cover: (00:00) Welcome Rex Gelb, Founder/CEO of Summit Chase (07:54) Why this was the right time to start a company (08:45) The sooner you give up, the better (11:05) Fighting the should gremlins (14:13) Work, family, and the balance trap (17:14) The newborn phase is not what you think (19:34) The “No 2AM Fight” rule (22:18) You do not need to master every phase (24:37) The household systems that keep things moving (27:43) Monthly leap alerts and using AI as a parent (30:31) Time hacks for dads building startups (35:43) Never deprive your kid of a struggle (39:37) Using AI for baby health questions (41:34) Raising a kid in the age of AI (43:23) Lightning round: Parenting philosophy, family rhythms, and raising an AI native kid Resources From This Episode: Summit Chase: https://www.summitchase.co/ Huckleberry (App): https://huckleberrycare.com/ Baby Shusher (App): https://babyshusher.com/pages/baby-shusher-app The Incredibles (Film): https://www.imdb.com/title/tt0317705/ The Sandlot (Film): https://www.imdb.com/title/tt0108037/ — Support Startup Dad For sponsorship inquiries, email: podcast@fishmana.com. For Startup Dad Merch: www.startupdadshop.com

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  • March 26 · 1 hr 2 min

    Family First Is Harder Than It Sounds | Jesse Randall (Dad of 5, Sweater Ventures)

    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 Randall LinkedIn: https://www.linkedin.com/in/sweaterceo/ Sweater: https://www.sweaterventures.com/ Where to find Adam Fishman FishmanAF Newsletter: www.FishmanAFNewsletter.com LinkedIn: https://www.linkedin.com/in/adamjfishman/ Instagram: https://www.instagram.com/startupdadpod/ X: https://x.com/fishmanaf In 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 most Resources 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 Dad For sponsorship inquiries, email: podcast@fishmana.com. For Startup Dad Merch: www.startupdadshop.com

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  • March 19 · 1 hr 9 min

    Parenting Through Projectile Vomit | Mike Rome (Dad of 3, moonwater)

    Mike Rome is the founder of moonwater, a performance marketing studio that helps startups grow, and a longtime operator in growth stage tech where he previously served as a CMO and growth leader. Before starting his own firm, he spent a decade inside venture-backed companies building teams and learning the craft of marketing. Mike and his wife Kate are parents of three boys and built their life around entrepreneurship, resilience, and perspective after navigating their son’s heart condition while launching his company. We discussed: Starting a company later in life: Why Mike believes the advice to launch startups young is a myth, and how having kids can sharpen focus and urgency. The myth of founder flexibility: Why running your own business doesn’t automatically mean more family time and the intentional tradeoffs required to design it. An accidental path to entrepreneurship: How quitting a new job after six weeks pushed Mike to start advising, which unexpectedly became his company. Building a company through crisis: What it was like launching a business while navigating his son’s rare heart condition and repeated hospital stays. The parenting power law: Applying startup frameworks like ICE and power laws to focus on the parenting moments that matter most. Presence over proximity: The mistake Mike made early as a founder-dad: confusing simply being around with actually being present. Where to find Mike Rome LinkedIn: https://www.linkedin.com/in/mike-rome/ Moonwater website: https://moonwater.co/ Where to find Adam Fishman FishmanAF Newsletter: www.FishmanAFNewsletter.com LinkedIn: https://www.linkedin.com/in/adamjfishman/ Instagram: https://www.instagram.com/startupdadpod/ X: https://x.com/fishmanaf In this episode, we cover: (00:00) Welcome Mike Rome! (02:35) The myth of starting startups young: why kids can sharpen focus (10:19) Starting a business with a family: turning an experiment into a company (15:08) Burning the boats: why real commitment matters when going solo (17:15) Gavin’s heart condition: navigating a family health crisis while building a company (23:19) When life hits hard: perspective, expectations, and resilience (39:39) The fishing realization: discovering the difference of shared time and shared interests (40:09) Bring kids into your passions: why parents should lead some adventures (40:54) Ignore the highlight reel: the danger of social media comparisons (42:57) Redefining success: gratitude, ambition, and moving goalposts (45:15) Presence over proximity: why simply being around isn’t enough (47:14) The dinner disaster: a dad weekend story that didn’t go as planned (52:59) The messy years: why chaos with young kids is something you’ll eventually miss (54:11) The Letter to Nirvana: a lesson on craft, conviction, and authenticity (59:40) Lightning round: dad hacks, dishwasher debates, and minivan takes Resources From This Episode: Steve Albini’s Letter to Nirvana: https://faroutmagazine.co.uk/steve-albini-letter-to-nirvana/ Impact, Confidence, Effort (ICE) Framework: https://www.productplan.com/glossary/ice-scoring-model/ Reforge (Growth Programs Mentioned in Discussion): https://www.reforge.com/ Feherty (Clothing Store): https://fahertybrand.com/ The Sandlot (Film): https://www.imdb.com/title/tt0108037/ The Goonies (Film): https://www.imdb.com/title/tt0089218/ Luca (Film): https://www.imdb.com/title/tt12801262/ Home Alone (Film): https://www.imdb.com/title/tt0099785/ iPad: https://www.apple.com/ipad/ Kia Telluride (SUV): https://www.kia.com/us/en/telluride — Support Startup Dad For sponsorship inquiries, email: podcast@fishmana.com. For Startup Dad Merch: www.startupdadshop.com

    • Transcript
Showing 21–23 of 23 episodes