Startup Dad

Sam Yagan, founder of OKCupid, former Match Group CEO, investor, and dad of three. He talks about raising kind, grounded kids amid wealth and ambition. He covers family systems like weekly meetings and annual reviews. He explains introducing philanthropy early, managing startup-era trade-offs, and shaping a home that draws kids and friends together.

A new dad shares why he and his partner quit stable jobs right after parental leave and how that leap reshaped their priorities. They discuss letting go of old identities, fighting perfection pressure, and practical household systems that reduce friction. They also talk about using AI for monthly milestone alerts, email threads for big family decisions, and intentionally letting kids face small struggles to build resilience.

Jesse Randall, founder and CEO of Sweater and father of five, shares candid takes on balancing ambition, marriage, and parenthood. He recounts moving his family to Puerto Rico, why prioritizing career can cost joy, and how fathers should lead with care. He explains a no-hint-dropping rule for better marriage communication and how he uses AI to reinvent his kids’ education and teach critical thinking.

Mike Rome, founder of moonwater and father of three, blends startup grit with parenting reality. He talks about launching a company later in life, designing real schedule flexibility, and building through his son’s heart crisis. He shares using startup frameworks for parenting, choosing presence over proximity, and the chaotic comedy of parenting moments like a projectile-vomit dinner.

Chris Winther, a former financial planner who became the primary caregiver for their three kids, and Amy Winther, Head of Product Design at Square and author of Motherboard. They recount a one-hour childcare pivot that flipped roles. They discuss shared finances and power, navigating being the lone dad in parent spaces, school and doctor defaults, and their yearly family planning system.

Jacob Bank, founder and CEO of Relay.app and former Google product leader, is a dad of three who built his company around flexibility and trust. He explains why small, async teams can be better for parents. He shares his three-part decision framework for leaving big tech, how he turns chores into bonding time, and a parenting trick called "Imagine if I Did That."

Amit Shah is the COO of Virta Health, a company on a mission to reverse Type 2 diabetes, and a dad to two young children. As a high-level executive and father, Amit has navigated the challenge of balancing his demanding career with raising a family. In this conversation, he shares his approach to intentional parenting, the value of shared family principles, and how he prioritizes both work and home life in his fast-paced world. We discussed:The power of partnership: How Amit and his wife, Bijal, support each other in their careers while raising two young kids.Balancing career and family: The conscious decisions Amit and Bijal made to ensure their careers and family life could thrive together, despite the challenges.Shared values in parenting: Amit’s approach to instilling values like kindness, curiosity, and persistence in his children and how he aligns with his wife on these principles.Parenting through trade-offs: The sacrifices Amit has made to maintain work-life alignment, including how they manage time, travel, and childcare logistics.Raising resilient kids: Amit’s thoughts on teaching his kids resilience through boundaries and handling disappointment.The importance of structure: How Amit uses his love for operations and structure to maintain balance and ensure his family’s needs are met.Where to find Amit ShahLinkedIn: https://www.linkedin.com/in/amitrshah1/ Where to find Adam FishmanFishmanAF Newsletter: www.FishmanAFNewsletter.com LinkedIn: https://www.linkedin.com/in/adamjfishman/ Instagram: https://www.instagram.com/startupdadpod/ In this episode, we cover:(00:00) Welcome Amit Shah, COO at Virta Health(03:49) The decision to start a family: career executives navigating parenthood(06:11) Shared values and partnership: aligning family and career priorities(07:59) Logistics and support systems: the power of the one calendar rule(29:35) Advice for career-focused executives considering parenthood(32:46) Facing the inevitable trade-offs: making parenting and career work together(33:16) Aligning family and career priorities: finding balance in a busy life(34:07) Parallels between work and family: applying business skills to parenting(34:49) Supportive work environment: the impact of a family-friendly workplace(36:01) Favorite books to read to kids: Amit’s go-to parenting reads(45:00) Balancing nutrition and health for kids: Amit’s approach to healthy eating(49:34) Negotiating parenting styles: challenges and compromises in raising kids(50:46) Fun and challenges of parenting: Amit’s personal parenting philosophy(54:49) Lightning round: the diaper genie, minivans, and other parenting hacksResources From This Episode:Virta Health: https://www.virtahealth.com/Diaper Genie: https://www.diapergenie.com/Minivans (Toyota Sienna): https://www.toyota.com/sienna/Giraffes Can’t Dance (Book): https://www.amazon.com/Giraffes-Cant-Dance-Giles-Andreae/dp/0545392551 Wonderbly (Personalized Books): https://www.wonderbly.com/Cat & Jack (Target Clothing Brand): https://www.target.com/b/cat-jack/-/N-qqqgm Khan Academy Kids (App): https://learn.khanacademy.org/khan-academy-kids/—Support Startup DadFor sponsorship inquiries, email: podcast@fishmana.com.For Startup Dad Merch: www.startupdadshop.com

Lee Robinson, VP of Developer Education at Cursor and former Vercel lead, is a husband and dad juggling hypergrowth AI startups and family life. He talks about how fatherhood reshaped his priorities and empathy. He discusses navigating startup pace while parenting, coping with pregnancy loss and anxiety, setting boundaries, sharing household responsibilities, and raising kids alongside rapidly advancing AI.

Pranav Piyush is the co-founder and CEO of Paramark, a marketing analytics company, and a dad to two young children. On his entrepreneurial journey, Pranav has faced health challenges, raised kids without a local support network, and balanced family life with the demands of running a startup. In this conversation, he shared his parenting philosophy alongside his founder wisdom. We discussed:The hero at home: How Pranav’s wife, Charu, has played a key role in supporting his entrepreneurial journey and balancing family life.Startup struggles and family life: The challenges Pranav faced starting a company with two young kids and without a local support system.The balance of 9-9-6: Pranav’s personal take on balancing work and parenting by dedicating quality time to his kids, especially on weekends.Parenting through health challenges: How a major health scare for one of his daughters shaped his perspective on family and resilience.Challenging kids to think: Pranav’s approach to fostering curiosity and critical thinking in his children, including using trivia and custom GPT tools.Building responsibility and agency: Why Pranav believes it’s crucial to instill a sense of personal accountability and how he applies this in his parenting.Where to find Pranav PiyushLinkedIn: https://www.linkedin.com/in/pranavp/ X: https://x.com/pranavpiyushWhere to find Adam FishmanFishmanAF Newsletter: www.FishmanAFNewsletter.com LinkedIn: https://www.linkedin.com/in/adamjfishman/ Instagram: https://www.instagram.com/startupdadpod/ In this episode, we cover:(00:00) Welcome Pranav Piyush, Co-Founder and CEO at Paramark(02:10) The hero at home: how Pranav’s wife supports his entrepreneurial dreams(06:02) Raising a family as immigrants: the challenges and rewards(22:03) Parenting principles: joining your kids in fun activities and creating memories(25:38) Challenging your kids: encouraging curiosity and critical thinking(30:24) Enjoying the small moments: family time, digital detox, and connecting(32:52) Education: why pranav believes it’s broken and needs change(33:20) Boredom in school: how it reflects a systematic issue(34:52) Solutions beyond school: the search for engaging education(35:49) The role of AI in education: will technology revolutionize learning?(36:30) Why college still matters: the importance of traditional education(41:25) Teaching personal accountability: how pranav instills responsibility in his kids(45:11) Technology and kids: setting boundaries and encouraging real-world experiences(47:16) Exciting family plans: what’s next for Pranav and his kids(49:57) Lightning round: the SNOO, unlimited iPad time, and other parenting hacksResources From This Episode:Paramark: https://paramark.com/ SNOO (and other Happiestbaby products): https://www.happiestbaby.com/ Zootopia 2 (Film): https://www.imdb.com/title/tt5042066/ Back to the Future (Film): https://www.imdb.com/title/tt0088763/Taylor Swift (Artist/Music): https://www.taylorswift.com/The Warriors (Basketball Team): https://www.nba.com/warriors/CocoMelon (TV Show): https://www.cocomelon.com/Toyota Sienna (Car Model): https://www.toyota.com/sienna/ Honda Odyssey (Car Model): https://www.honda.com/odyssey GTMN (Podcast): https://podcasts.apple.com/us/podcast/gtmn/id1845001203  Brandformance (Podcast): https://podcasts.apple.com/us/podcast/brandformance/id1746064786  —Support Startup DadFor sponsorship inquiries, email: podcast@fishmana.com.For Startup Dad Merch: www.startupdadshop.com

Jason Smith is the Co-Founder and CEO of Klue, an AI-powered competitive intelligence platform. He’s a five-time startup founder, Ernst & Young Entrepreneur of the Year, and a father of two daughters. But his most transformative experience wasn’t raising capital or scaling companies. It was stepping away from it all to travel the world with his wife and kids.When his daughters were just 8 and 9, Jason and his wife quit their jobs, pulled the kids out of school, and spent a full year traveling across 11 countries. We discussed:Leaving work to reconnect: What prompted Jason to walk away from startup life and plan a year-long trip around the world with his wife and two daughters.When things go wrong: Why Jason believes travel disasters make the best family memories and how they used setbacks to teach adaptability and problem-solving.Building deep connections off-grid: How spending 24/7 together changed their family dynamic, from independent dinners to hard conversations.Teaching self-reliance through discomfort: Jason shares his philosophy on preparing kids for the real world and why he sees challenge as essential, not optional.From startup grind to dad mode: The binary approach Jason takes to work and parenting, and why he believes being all-in matters more than balance.How his daughters see him now: Why watching their dad work hard, and then totally disconnect, influenced how his kids think about careers, failure, and ambition.Where to find Jason SmithLinkedIn: https://www.linkedin.com/in/onemoresmith/  Where to find Adam FishmanFishmanAF Newsletter: www.FishmanAFNewsletter.com LinkedIn: https://www.linkedin.com/in/adamjfishman/ Instagram: https://www.instagram.com/startupdadpod/ In this episode, we cover:(00:00) Welcoming Jason Smith, Co-Founder and CEO at Klue(01:09) What sparked a year-long trip around the world(02:21) How planning the journey went from 6 weeks to 12 months(05:08) The wild story of renting their house before quitting their jobs(06:33) Early travel struggles and breakthrough moments(09:54) Teaching kids on the road and bringing learning to life(12:48) Volunteering in Peru and breaking the privilege bubble(17:03) Favorite travel memories and embracing the unexpected(24:51) Why real connection takes getting off the grid(36:17) How his daughters see startups and business now(39:35) Navigating AI and the new rules of work(41:15) Building resilience by leaning into hard things(46:27) United front parenting and avoiding the ‘ask mom, ask dad’ trap(48:26) How the parent-child relationship evolves over 20 years(51:44) Teaching work ethic and financial independence(01:00:49) Lightning round: parenting quirks, movie picks, and minivan takesResources From This Episode:Klue: https://klue.com/ Jason’s Travel Video: https://www.youtube.com/watch?v=O1vMnTDHe6c One More Smith (Jason’s Blog): https://onemoresmith.com/ Jolly Jumper: https://jollyjumper.com/ The Matrix (Film): https://www.imdb.com/title/tt0133093/ Frozen (Film): https://www.imdb.com/title/tt2294629/ Support Startup DadFor sponsorship inquiries, email: podcast@fishmana.com.For Startup Dad Merch: www.startupdadshop.com