Startup Dad

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-achieving parents, and why Sam believes “normal” is overrated.

We also get into the systems that shape their household, from weekly family meetings and value shout-outs to annual family reviews and intentionally making their home the place where all the kids want to hang out. We discussed: 
Raising grounded kids in a high-achievement household: How Sam and his wife work to keep their kids kind, self-aware, and unentitled despite growing up around success and wealth.
Building family values into everyday life: How Sam’s family uses weekly meetings, value shout-outs, and annual reviews to make generosity, kindness, and self-awareness part of daily life.
Introducing philanthropy before personal wealth: Why Sam wants his kids’ first understanding of money to center on giving, impact, and responsibility.
Choosing the right partner for the long game: Why Sam believes ambitious founders need a spouse who shares their values and vision for family life.
Creating a home that pulls people in: How Sam and his wife built a family environment where kids and friends naturally gather, creating more connection and shared memories.
Bringing a founder mindset into parenting: Why Sam believes decisiveness, experimentation, flexibility, and comfort with failure matter at home too.

Where to find Sam Yagan
LinkedIn: https://www.linkedin.com/in/samyagan/
X: https://x.com/samyagan

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 Sam Yagan, Former Founder/CEO of OKCupid & Match Group
(02:44) Raising kind kids in a world of privilege
(04:59) Family values meetings that actually work
(06:23) When your kids start asking about net worth
(12:10) Why philanthropy comes before wealth
(14:57) Work-life integration during the startup years
(18:29) The tradeoffs that come with constant travel
(20:59) The pressure kids feel from successful parents
(22:27) Teaching a “fail forward” mindset at home
(26:58) Why normal is boring
(29:24) Why choosing the right partner matters
(32:53) Putting your family values on the wall
(36:27) The annual family review
(38:47) Making your home the hangout house
(48:01) Lightning round: Parenting products, dishwasher rules, and Sam’s hard no on minivans

Resources From This Episode:
OKCupid: https://www.okcupid.com/ 
Match Group: https://mtch.com/ 
Playing cards: https://a.co/d/05A9UUbF
Basketball: https://a.co/d/0erx9ow0 
Harry Potter and the Sorcerer's Stone (Film): https://www.imdb.com/title/tt0241527/ 
A Few Good Men (Film): https://www.imdb.com/title/tt0104257/ 
Toyota Highlander (Car): https://www.toyota.com/highlander/ 
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For Startup Dad Merch: www.startupdadshop.com

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/ 

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Support Startup Dad
For sponsorship inquiries, email: [email protected].
For Startup Dad Merch: www.startupdadshop.com

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/ 

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Support Startup Dad

For sponsorship inquiries, email: [email protected].
For Startup Dad Merch: www.startupdadshop.com

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

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Support Startup Dad

For sponsorship inquiries, email: [email protected].
For Startup Dad Merch: www.startupdadshop.com

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 the home. And what’s wild is how fast it came together. One brutal childcare moment, their third nanny situation falling apart, and they made the call in basically an hour. We discussed:
Childcare chaos that forced a fast decision: The nanny and scheduling breaking point that made them change their whole setup in basically an hour.
Flipping the traditional script: Why Amy stayed in her career and Chris became the primary parent, and what surprised them about how it felt in real life.
Money, power, and partnership: How “what’s mine is yours” removed tension early, and how they split ownership across work and home without resentment.
Being the only dad in kid spaces: The awkwardness at playgrounds and playdates, the “creepy guy” fear, and how Chris found his footing and community.
Schools and doctors calling mom first: The practical playbook for getting institutions to recognize the primary parent, even when defaults are outdated.
Their annual family meeting system: The repeatable way they plan goals, calendars, health, and money so life doesn’t just “happen” to them.

Where to find Amy Winther
LinkedIn: https://www.linkedin.com/in/amywinther/
IG: https://www.instagram.com/winnie_gram/

Where to find Chris Winther
https://www.instagram.com/cdubbonline/

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 Amy Winther, Head of Product Design at Square, and Chris Winther, Stay-At-Home Dad
(03:21) The childcare breaking point that flipped their roles
(08:49) Why Amy thought she’d be the one to stay home
(12:00) Chris on the identity shift from career to primary parent
(13:29) Money and power dynamics and why shared finances matter
(16:38) Stay-at-home dad social life and finding your people
(21:06) The assumptions, the mental load, and the stuff no one says out loud
(27:22) Rewiring the default mom call at schools and doctors
(29:26) Time is the real budget and how they protect it
(32:58) The annual family planning meeting that keeps them aligned
(38:43) Working backwards from the life they actually want
(40:08) Renovation bootcamp year while raising kids
(43:38) You and me versus the baby mindset
(45:13) Advice for couples considering a role swap
(55:09) Lightning round: SlumberPod wins, dishwasher rules, and the minivan debate

Resources From This Episode:

Square: http://squareup.com/   
Mother Board: https://amywinther.substack.com/p/welcome-to-mother-board
v0.app: https://v0.app/   
SlumberPod: https://www.slumberpod.com/  
Cocomelon (TV Show): https://www.imdb.com/title/tt12427840/ 
Paw Patrol (TV Show): https://www.imdb.com/title/tt3121722/ 
Paddington (Film): https://www.imdb.com/title/tt1109624/ 
Jurassic Park (Film): https://www.imdb.com/title/tt0107290/ 
Toy Story (Film): https://www.imdb.com/title/tt0107290/ 
VW ID. Buzz (Minivan): https://www.vw.com/en/models/id-buzz.html 
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Support Startup Dad

For sponsorship inquiries, email: [email protected].
For Startup Dad Merch: www.startupdadshop.com