In this special episode of Depends on the Context, I sit down with one of my oldest friends, Noah Falkenstein, to remember his beloved mother, Paula Falkenstein z״l.

Paula passed away from cancer in 1998 when Noah was just 12 years old. Nearly three decades later, Noah reflects on the woman who shaped his life, what he remembers from her illness, the day she died, the people who carried him through unimaginable loss, and the values his mother instilled in him that he now hopes to pass on to his own children

Topics discussed:

• Growing up in Riverdale and Noah's earliest memories of Paula
• Paula's warmth, love, and devotion to her family
• Her breast cancer diagnosis and the family's experience
• Losing a parent at twelve years old
• Friends, community, and healing after tragedy
• Becoming a parent without your own mother there
• The values Paula left behind
• What Noah hopes his children will remember about his mother

Why is healthcare so expensive, and can AI actually help fix it?

In this episode, I sit down with Chris Look, a founding engineer and healthtech builder who has worked across Amazon, Blueberry Pediatrics, Fortuna Health, and his own startup. We explore why incentives, more than technology, often determine healthcare outcomes, where AI can meaningfully improve care, and what the healthcare system could look like over the next decade.

• We discuss:
  • Why Chris has spent his career in healthcare
  • The incentive problems driving rising healthcare costs
  • Where AI can create real value—and where it can't
  • Prior authorization, value-based care, and administrative burden
  • What the future of healthcare might look like

Phish just wrapped up its "Phish in Five" run at Madison Square Garden with one of the most memorable shows in recent memory.

I'm joined by my good buddy phish29, to break down what made Night 5 truly special. From the rarity-filled first set and Harpua narration filled with historical callbacks, to the epic YEM and Crosseyed jams, we discuss why this show was more than just another great Phish concert.

Most ecommerce brands know what their customers buy- but very few know who their customers actually are.

That gap may become one of the biggest competitive advantages in ecommerce over the next decade.

In this episode, I chat with Dov Quint, VP of Customer Experience at OuterSignal, about why customer identity is becoming one of ecommerce's biggest competitive advantages, how AI is changing the way brands understand their customers, and what the future of ecommerce could look like.

Dov and I discuss:

• Why most ecommerce brands don't actually know their customers
• Why traditional customer personas often miss the mark
• How AI is making individualized customer understanding possible
• The surprising stories hidden inside customer data
• What convinced Dov to join OuterSignal as employee #2

Learn more about OuterSignal: https://www.outersignal.com/

What happens when AI hits an industry built on expertise, hierarchy, and billable hours?

In this episode, Avi Lichtschein sits down with Andrew Keller, Senior Counsel at Covenant and former attorney at Kirkland & Ellis, CVC, and BlackRock, to discuss how AI is changing the economics of legal services.

Avi and Andrew explore AI-native law firms, the future of the billable hour, where human judgment still matters, and how technology shifts where value lives inside organizations.

Guest: Andrew Keller

Links: Covenant: ⁠https://www.covenant.co⁠ Andrew Keller: ⁠https://www.linkedin.com/in/andrew-j-keller-17226b5a/⁠

The Siz joins Avi for their annual NBA Draft conversation- now in its 22nd year. To mark the occasion, they take a look back at the past 22 NBA Drafts since the tradition began, and revisit: the biggest stars, surprise picks, busts, and what-if stories along the way.

They also catch up on family, life updates, the Knicks' incredible championship run, and Avi's future move to Israel before making their predictions for the 2026 NBA Draft.

Here's to the next 22 years!

Recorded less than 48 hours after the Knicks won the 2026 NBA Championship, Avi welcomes his first-ever podcast guest, longtime friend and diehard Knicks fan Daniel Shabtai, to process what just happened.

Together they revisit two decades of Knicks fandom, from the Marbury years and draft lottery heartbreak to Linsanity, Melo, and finally Jalen Brunson leading New York to a title.

Part Knicks history, part friendship story, and part therapy session, this conversation captures what the championship meant to one fan and in many ways, an entire generation of Knicks fans who waited decades for this moment.

Every AI startup is suddenly hiring forward deployed engineers - and almost nobody agrees on what the role actually is.

So here’s an FDE 101: what the job is, why it’s exploding in the AI era, and a Star Wars framework for understanding five archetypes you’ll meet in the wild- plus three paths to the dark side that can quietly harm FDE organizations.

Every week, I use ChatGPT to help bring Parsha to life for my kids.

By turning weekly Parsha summaries into custom visual scenes — by placing my own children directly into the Parshat HaShavua — AI has become a meaningful parenting and chinuch tool in our home.

This episode is about Torah, fatherhood, technology, and why I want my children’s earliest memories of AI to be rooted in ways that make the Torah feel even more alive.

A quick story about the time I (kind of) jammed with Mike Gordon, plus a few other Mike-related moments I randomly remembered.