Ami Kozak is well known today as a comedian, impressionist, podcaster and increasingly serious public voice. But before TikTok, viral impressions and public debates, Ami spent years building a creative career through music, advertising, commercial jingles and his band, Distant Cousins.

I’ve known Ami since we were teenagers, and we traced that entire journey- from Battle of the Bands and pursuing music, to becoming known not only for his humor, but also for his thoughtful engagement with serious issues.

Ami and I also discuss the realities of building a career online: consistently producing content, resisting audience capture, balancing comedy with conviction and staying present with your family when your livelihood lives on your phone.Show Notes* September 27 performance in Monsey - Tickets* October 1 performance at The Cheese Store - Tickets* “Happiness Is Calling” - San Diego commercialBe sure to check out Ami's podcast, Ami’s House!

For more than 20 years, Hillel Fuld built an extraordinary career in Israeli tech by doing something remarkably simple: helping people. Hillel made introductions, advised startups, built relationships, and became one of the most connected people in the Israeli tech world.

Then October 7 happened- and almost overnight, everything he had spent decades building took on a new purpose.

Hillel and I discuss what happened next: why he shut down his consulting business to advocate for Israel full-time, how he put decades of relationships to work for Israel, whether advocacy can actually change minds, and the personal cost of speaking up.

Hillel and I also talk about his warning for American Jewry, why he believes Aliyah is becoming increasingly urgent, and his conviction that everything he built before October 7 was preparing him for what came next.

Sara Mauskopf never thought of herself as an entrepreneur. Then she had her first child and realized the company she wanted to work for- and the childcare solution she needed- didn’t exist.

Ten years later, Sara is the co-founder and CEO of Winnie, one of the largest childcare marketplaces in the country. Sara and I discuss why she wishes Winnie hadn’t raised so much money so early on, how Winnie stumbled into its business model, the moments she thought the company might not survive, building a company while raising three kids, and what a decade spent thinking about childcare has taught her about work, parenting, and the choices families make.

Links:
Winnie: winnie.com
Sara Mauskopf: X | LinkedIn