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

I turned 40 this summer and wanted to leave my kinderlach a snapshot of their Abba at this age as they're still little.

I talk about becoming a Abba, regrets in my life that disappeared and the one that didn't: my desire to know more Torah.

Mostly, this episode is a time capsule for Raina, Yehuda, Baila, IH#4 etc.

tl;dr - A photograph preserves what your children looked like. I want this episode to preserve the perspective of the 40-year-old Abba who was watching them.

There’s an entire category of valuable real estate hiding in plain sight: empty parking lots, unused acreage, industrial yards, and other land that most of us barely notice.

Rafi Katz, founder and CEO of Yardflow, saw an opportunity to connect property owners sitting on underused land with companies looking for places to park fleets, store equipment, stage construction materials, and support projects ranging from telecom infrastructure to data centers.

In this episode of "Depends on the Context," Rafi and I discuss how he stumbled into this market and why finding outdoor storage has historically been so difficult. We get into how Yardflow grew to thousands of yards nationwide, the unexpected impact of the data-center boom, and what Rafi has learned building a marketplace for a surprisingly large but largely invisible corner of the real estate world.

Learn more about Yardflow: https://getyardflow.com

My uncle Ari was killed in the World Trade Center on September 11, 2001. Today is his yahrzeit, and with the 25th anniversary of 9/11 approaching, I wanted to share a conversation I recorded last year with my brother Elie.

Elie and I talk about the uncle we knew, what we remember from 9/11 and its aftermath, how losing him changed our family-particularly our father and grandmother- and the questions we wish we could ask him today. This isn’t a polished biography: just two brothers sharing memories of our beloved uncle.

New York Times obituary (archived on Legacy.com): “The Favorite Uncle”

Note: This conversation was originally recorded in 2025 for An Excuse to Talk to My Brother.

I was at the park on Shabbos, pushing my 8 month old daughter on the swings, when Ms. Rachel put her daughter on the swing next to mine. So I said something.

What followed was a conversation about Israel, Gaza, Zionism, the genocide accusation, antisemitism, and the consequences of having an enormous platform. She pushed back. I pushed back. She said some things that genuinely surprised me, she got a little emotional and walked away — and I subsequently finished the conversation with her husband.

(sorry about the edit overlay at 6:29 where I clarify that she said she’s NOT an anti-Zionist... I’m still learning how to edit!)

Natan Wise is the co-founder and CEO of Conduit Health, a healthcare startup making it easier for patients to access medical equipment and supplies through insurance.

Natan and I talk about how Conduit got started, the pivot that changed the business, why healthcare is so difficult to navigate, how AI is transforming its operations- and the parts AI still can't solve.

We also get into what it's like to build a company with a close friend, stacking wins, and Natan's advice for founders entering industries they don't fully understand.

Chapters:
(00:00) From Thrasio to medical equipment

(12:46) Tearing up the marketplace model

(15:20) One wheelchair, start to finish

(21:00) Where AI helps, and where it doesn't

(28:03) What surprised him about being CEO

(37:07) Five years out

Links

Conduit: https://www.conduithealth.com/
Careers: https://www.conduithealth.com/careers
Natan: https://www.linkedin.com/in/natan-wise/

My good buddy Cantor and I are both avid Phish fans and have been playing a game for over 20 years: one of us recreates a Phish song using only our voice, and the other has to guess it. No instruments or lyrics allowed - just our mouths "playing" the riffs and bass lines.

This episode is either:

a) incredibly entertaining
b) something you'll switch off within 2 minutes

... with absolutely no in between.

Blake Johnson taught himself to code before ChatGPT, went on to teach at Flatiron School, and today is an engineer at Clay.

In this episode, we talk about Blake's journey from teaching himself to code to teaching others, how AI has completely changed the way he builds software, and what his work at Clay looks like today- where he's using AI to rethink how software gets built.