Daycare vs nanny: why the third tipped it

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 intentionally designed both their company and their family life around flexibility, autonomy, and depth over scale. We discussed:

• Leaving Google with a baby at home: The three-part framework Jacob used to decide when it was financially and professionally the right time to start again.
• Why startups can be better for parents: How small, async teams with high trust can offer more flexibility than big companies.
• Double-dipping as a dad: Turning errands, chores, and workouts into bonding moments with his kids.
• “Imagine if I Did That”: The parenting framework Jacob uses to teach emotional regulation and responsibility.
• Patience through repetition: How each additional child made him calmer, more flexible, and less reactive.
• Raising AI native kids: Helping children develop intuition and depth while still embracing powerful new tools.

Where to find Jacob Bank

• LinkedIn: https://www.linkedin.com/in/jacobbank/ 
• X: https://x.com/jebank
  
  

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 Jacob Bank!

(02:30) Parenting with a pediatrician spouse: the blessing and the anxiety tax

(04:45) The 3-part decision framework: bills, growth, and daily fit

(08:32) Big company vs startup “risk”: what’s actually safe in a modern career

(11:13) Founder paternity leave: the phased approach that made it workable

(15:22) Why small teams can be best for parents: async culture, no meetings, high trust

(20:40) Logistics and support systems: daycare, nanny, family, and parent carpools

(27:33) Daycare vs nanny: why kid three changed everything

(32:12) Double dipping: turning chores and errands into quality time

(36:19) Kids and work talk: bringing them into problems and building curiosity

(41:19) How three kids changes you: patience, flexibility, and letting go of control

(46:58) “Imagine if I Did That”: Jacob’s tantrum and behavior framework

(49:56) Redefining founder success: staying small, profitable, and intentional

(54:11) Negotiating parenting styles: physical risk and the playground debate

(55:27) AI at home: curiosity threads, voice mode, and raising AI-native kids

(59:44) Lightning round: CocoMelon trauma, minivans, and dad grocery store dominance

Resources From This Episode:

Relay.app: https://www.relay.app/ 

Rider Safe Travel Vest: https://ridesafertravelvest.com/

Little House on the Prairie (Audiobook): https://www.audible.com/pd/Little-House-on-the-Prairie-Audiobook/B01N12SFSC

Leo (Film): https://www.imdb.com/title/tt5755238/ 

Bluey (TV Show): https://www.imdb.com/title/tt7678620/ 

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