Davidi Jonas went from being a high school rebbe and shul rabbi with no college degree to running Straight Path Communications, a company that sold to Verizon for $3.1 billion.

In this episode of Depends on the Context, Davidi and I explore his unlikely journey into telecommunications, the emergence of 5G, navigating the FCC, and the extraordinary bidding war between AT&T and Verizon- including what happened over Shabbos.

Along the way, we discuss opportunity, family connections, hard work, and Hashgacha Pratis- and how much of our success is really in our hands.

Today marks the first yahrzeit of my grandmother, Suri Lichtschein z"l, aka Babi Yaya.

In this special episode, my brother Elie and I look back on Babi's extraordinary 99 years of life — from surviving Auschwitz and rebuilding her life after the Holocaust to becoming the beloved matriarch of our family.

We share childhood memories, funny stories, and reflections on her remarkable sense of humor, unwavering emunah, and the legacy she left behind.

Originally recorded last year for our podcast An Excuse to Talk to My Brother, I'm republishing this conversation here on Depends on the Context in honor of her first yahrzeit.

May her neshamah have an aliyah.

My kids never asked me to buy them 340+ Peppa Pig toys.

I did it anyway.

It started with two Afikoman presents. Six months later, I had made 201 separate purchases and spent $1,377.90 on Peppa Pig.

Along the way, Peppa became part of bath time, Shabbos, learning Navi- and somehow I ended up drawing faces on actual potatoes from the bodega.

This is the story of how something genuinely good got completely out of hand and what my kids understood about it before I did.

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