Startup Dad

Caleb Avery is the Founder and CEO of Tilled . He started his first company at 19 and has spent the last seven years building Tilled while raising three kids with his wife, Kelsey. In this episode, Caleb shares what it really looks like to build a startup and a family at the same time. We talk about the trade-offs founders need to be honest about, his regrets around paternity leave with his first...

Sam Yagan is the founder of OKCupid and former CEO of Match Group . He’s also an investor, board member, married to a CEO, and a dad of three kids ages 12 to 18. In this episode, Sam shares how he and his wife think about raising kind, grounded kids while navigating success, wealth, and ambition. We talk about family values, philanthropy, work-life integration, the pressure kids can feel from high...

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...

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...

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 a...

Amy Winther is the Head of Product Design for Core Products at Square and the writer behind Motherboard, a Substack sharing honest stories about senior women in big tech. Chris Winther is a former financial planner turned stay-at-home dad and the primary parent for their three kids. They’ve built a family setup that flips the traditional script. Amy’s the full-time working parent and Chris runs th...

Jacob Bank is the Founder and CEO of Relay.app , a profitable, fast-growing startup that helps teams build AI agents to automate their work. Previously, Jacob founded Timeful, which was acquired by Google, where he spent six years before leaving to start Relay when his first daughter was just six months old. He and his wife Sonia, a pediatrician at UCSF, now have three young kids and have intentio...

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 ho...

Lee Robinson is the VP of Developer Education at Cursor , one of the fastest-growing AI developer tools in the world. Before Cursor, he spent five years at Vercel helping define how modern developers learn and build on the web. He’s also a husband and a dad to a young daughter, with a second daughter on the way. When I first invited Lee on the show, he had a five-month-old baby and felt like he wa...

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...

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 an...

Dr. Emilio Galán is a former medical student, entrepreneur, and now a full-time stay-at-home dad. He took a drastic turn in his career, moving from building a successful AI-driven company to focusing on family life after stepping away from the startup world. Dr. Galán shares how he navigated autoimmune health challenges, the difficult decision to leave his medical career behind, and the challenges...

Michael Goodbody is the former Global Head of Marketing & Communications at Robinhood , CMO at Dave, and VP Marketing  at Credit Karma. A year ago, he resigned from his executive job at Robinhood to homeschool his children while traveling to 21 countries in just nine months. Michael, a British expat married to a German partner, shares what it was like stepping away from a demanding executive c...

Andrew Song is the co-founder of Make Sunsets , a climate startup working to slow global warming by deploying reflective aerosols in the stratosphere. A longtime startup operator, Andrew has spent his career taking contrarian paths, from early work in AI to now building one of the most debated climate interventions in the world. At Make Sunsets, he focuses on translating complex science into pract...

This special episode looks back at the most powerful moments from Startup Dad in 2025. Host Adam Fishman reflects on a year of raw, honest conversations with 46 founders, operators, and leaders who are also Dads (and sometimes, Moms) navigating the chaos of startup life while raising families. From redefining balance and sharing mental load to leading through crises and building parenting systems...

Daniel Borok is a Managing Partner at nvp capital , an early-stage venture firm investing in founders building the next generation of vertical AI companies. With a focus on B2B applications, Dan spends his days meeting visionary entrepreneurs, making high-conviction bets at the pre-seed and seed stages, and helping early teams build durable companies. Before nvp, he held operating and investing ro...

Oji Udezue is an AI Product Expert at ProductMind , and a veteran product leader with more than 25 years of experience across Typeform, Twitter, Calendly, Atlassian, Bridgewater, and Microsoft. He’s known for his deep thinking on product craft, leadership, and the future of work. He’s also the co-author (with his wife, Ezinne Udezue )  of Building Rocket Ships , a guide for builders and operators...

Allison Daminger is an Assistant Professor of Sociology at the University of Wisconsin-Madison , where she specializes in gender, family dynamics, and social inequality. She’s also the author of What’s on Her Mind: The Mental Workload of Family Life , which explores the often invisible cognitive labor that drives the daily operations of households. In this episode, we talk about the concept of cog...

Jamie Nacht is the co-founder and CEO of Havium , a company he built from the ground up with his wife and co-founder, Cristin. Together, they’re raising two young kids while juggling the nonstop realities of startup life, marriage, and modern parenting, all as a fully integrated team. In this episode, Jamie shares his honest and often hilarious take on building a company with your spouse, creating...

Dave Simnick is the founder and CEO of Soapbox , a company with a mission to provide personal care products while donating soap to those in need. He's also a husband and the father of a one-year-old son, Noah. Listen to the whole episode for an amazing discount code at Soapbox!  In this episode, Dave shares insights about the changes he faced when becoming a parent and how he’s adjusted his role a...

In this episode of Startup Dad, Adam Fishman sits down with Chet Kittleson , serial founder and co-founder of Tin Can , an analog phone for kids that helps families stay connected without screens. He’s also a dad of three, building a hardware company from his kitchen table while raising a young family in Seattle. Chet opens up about the inspiration behind Tin Can, how his childhood landline shaped...

In this episode of Startup Dad, Adam Fishman sits down with Colin Anawaty , technologist and founder of Flying A Capital . He’s also a single dad of two boys, navigating the challenges of fatherhood and entrepreneurship after divorce. Colin opens up about how his kids have become his greatest teachers, why he believes accountability and independence should start young, and how joining a men’s grou...

Chad Pytel is the founder and CEO of thoughtbot , a product development consultancy, and co-founder of 12 Sided Studios , a gaming and production company. He’s also the longtime host of the Giant Robots Smashing Into Other Giant Robots podcast, a husband, and the father of two teenagers. In this episode, Chad and I talk about raising kids while running companies, blending family life with creative...

Jonathan Jamil , founder and CEO of Springboard , shares his story of growing up in a two-bedroom apartment with six family members, building a business powered by stay-at-home moms, and raising two daughters while redefining what success means. In this episode, Jonathan opens up about his entrepreneurial journey, the lessons he has carried from his upbringing, and the realities of being a dad and...

In this episode of Startup Dad, I sit  down with Adam Lieb , the founder and CEO of Gamesight , a marketing technology company that helps video game studios connect with players and launch their biggest titles. Adam started his first gaming business at just 11 years old and has spent his entire career building in the industry ever since. As a dad of 11-year-old twins and husband to Camille, a lawy...