Managing Four Kids' Schedules and Activities

Jonathan Stull is the President and COO of Handshake, the career platform connecting students and recent grads with employers that recently made a massive pivot into scaling an AI product. He’s spent the last decade helping build the company from a seed stage startup working out of a house in Palo Alto into a massive platform serving millions of students, universities, and employers.

He’s also a husband to Emmy-winning journalist Emily Chang and a dad of four kids, ages 13, 11, 9, and 6. At home, he’s juggling the beautiful chaos of school drop-offs, carpools, Little League, robotics, math enrichment, ski trips, and four very different schedules. In our conversation, we talked about how Jonathan and Emily rely on their nanny, grandparents, neighbors, and community to make it all work, the challenge of being present when work is still running in the background, why kids need agency and resilience more than ever, and how becoming a dad has made him a more direct and caring leader. We discussed:

• Building a life with four kids: How Jonathan and his wife manage the beautiful chaos of school, sports, activities, and constant logistics.
• Relying on your village: Why their nanny, grandparents, carpools, neighbors, and community are essential to making family life work.
• Staying present when startup life is intense: The challenge of being physically at a kid’s game while mentally pulled into Slack, AI agents, and company decisions.
• Raising kids with agency in the AI era: Why Jonathan believes resilience, adaptability, self-starting, and passion matter more than ever.
• Parenting through direct feedback: How being a dad helped Jonathan become a clearer, more direct, and more caring leader at work.
• Embracing adventure before the years disappear: Why Jonathan tries to say yes to family trips, backyard games, and small moments of connection.

Where to find Jonathan Stull

• LinkedIn: https://www.linkedin.com/in/jonstull/ 

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 Jonathan Stull, President and COO of Handshake (and baseball coach)
(02:14) Why Jonathan and Emily decided to have four kids
(03:53) Managing the beautiful chaos of four schedules
(05:51) Building the village that keeps family life moving
(09:46) The first moment fatherhood really hit
(10:42) Growing Handshake while learning to stay present at home
(16:25) Why parents should not wait for the perfect time
(19:36) What kids teach you about resilience
(22:11) Showing up, saying yes, and protecting family time
(24:35) How parenting made Jonathan a more direct leader
(27:09) Navigating enrichment, ambition, and different parenting instincts
(30:00) Raising kids to be ready for an AI shaped future
(31:20) Why agency matters more than following a playbook
(34:10) Using AI to plan trips, pranks, and Little League schedules
(39:12) Lightning round: white noise, limericks, dad pranks, and minivans

Resources From This Episode:

Handshake: https://joinhandshake.com/ 

SNOO Smart Sleeper Bassinet: https://www.happiestbaby.com/products/snoo-smart-bassinet 

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

The Lion King (Film): https://www.imdb.com/title/tt0110357/
Billy Madison (Film): https://www.imdb.com/title/tt0112508/ 

Braveheart (Film): https://www.imdb.com/title/tt0112573/ 

Glory (Film): https://www.imdb.com/title/tt0097441/ 

Anchorman: The Legend of Ron Burgundy (Film): https://www.imdb.com/title/tt0357413/ 

Old School (Film): https://www.imdb.com/title/tt0302886/

Wedding Crashers (Film): https://www.imdb.com/title/tt0396269/ 

Chevrolet Suburban (Car): https://www.chevrolet.com/suvs/suburban 

Chrysler Pacifica (Car): https://www.chrysler.com/pacifica.html 

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