Vol. II — No. 27
Friday, July 3, 2026
Est. MMXXV
TL;DL
Too Long, Didn't Listen
A Weekly Ledger of Long-Form Audio
339 Episodes in the Archive

Podcast — Lenny's Podcast: Product | Career | Growth

38 Entries
№ 01
Lenny's Podcast: Product | Career | Growth · Lenny Rachitsky
Building the most AI-pilled engineering team in the world | Fiona Fung (Manager of the Claude Code and Cowork Teams)
Anthropic engineering leader Fiona Fung describes a software world where code is abundant, initiative matters more than syntax, and managers rely on AI to track quality, feedback, and the work itself. The conversation traces how engineering, product management, and team culture are being remade by agents, even as loneliness, fear, and accountability become harder problems to solve.
Jun 21 · 1h 38m · ai, product, technology
Jun 21
1h 38m
ai, product, technology
№ 02
Lenny's Podcast: Product | Career | Growth · Lenny Rachitsky
Father of the iPod and iPhone on building taste, judgment, and creativity in the AI era | Tony Fadell
Tony Fadell argues that breakthrough products come from identifying real pain, pairing it with newly viable technology, and shaping the entire customer journey, from interface to marketing story. He warns that AI can accelerate prototyping but cannot replace human judgment, taste, and responsibility without leaving builders with brittle products and long-term debt.
Jun 7 · 1h 35m · product, ai, technology
Jun 7
1h 35m
product, ai, technology
№ 03
Lenny's Podcast: Product | Career | Growth · Lenny Rachitsky
A rational conversation on where AI is actually going | Benedict Evans
Benedict Evans argues that AI is a platform shift on the scale of the internet or mobile: transformative, messy, and still too early for anyone to know where the real value or disruption will settle. He pushes back on jobpocalypse panic, sketching a slower, more uneven reshaping of work in which adoption, distribution, and new kinds of services matter more than apocalyptic forecasts.
May 31 · 1h 19m · ai, technology, business
May 31
1h 19m
ai, technology, business
№ 04
Lenny's Podcast: Product | Career | Growth · Lenny Rachitsky
The AI paradox: More automation, more humans, more work | Dan Shipper
Dan Shipper argues that AI is remaking work less by replacing people than by changing the interfaces around them: companywide agents in Slack, desktop copilots that become the operating system for knowledge work, and SaaS products rebuilt for humans and machines to collaborate together. He is strikingly bullish on the survival of SaaS, the rise of forward-deployed AI operators, and the prospects for product managers and full-stack designers who learn to ride the models.
May 24 · 1h 34m · ai, product, technology
May 24
1h 34m
ai, product, technology
№ 05
Lenny's Podcast: Product | Career | Growth · Lenny Rachitsky
Why we’re at the beginning of the AI hardware boom | Caitlin Kalinowski (ex–OpenAI, Meta, Apple)
Hardware veteran Caitlin Kalinowski argues that AI’s next great expansion will happen not on screens but in factories, robots and supply chains, where safety, manufacturing know-how and geopolitical risk matter as much as software. Drawing on stints at Apple, Meta and OpenAI, she sketches a future shaped by AR, drones and reindustrialization, while warning that war may change faster than consumer tech.
May 17 · 1h 39m · ai, technology, politics
May 17
1h 39m
ai, technology, politics
№ 06
Lenny's Podcast: Product | Career | Growth · Lenny Rachitsky
How to build a company that withstands any era | Eric Ries, Lean Startup author
Eric Ries argues that good companies rarely collapse because of competition; they are more often hollowed out by governance, incentives and financial pressure that turn success into a liability. Drawing on examples from Anthropic, Novo Nordisk, Cloudflare and Philip Morris’s disastrous purchase of Vectura, he makes the case that founders must build mission protection into both culture and corporate structure before it is too late.
May 10 · 1h 39m · startup, business, ai
May 10
1h 39m
startup, business, ai
№ 07
Lenny's Podcast: Product | Career | Growth · Lenny Rachitsky
Why cultivating agency matters more than cultivating skills in the AI era | Max Schoening (Head of Product, Notion)
Max Schoening, Notion’s head of product, argues that AI is making the first draft of software nearly free while shifting the real differentiator to agency, taste and the discipline to make something obviously good. The conversation ranges from designers coding in terminals to the persistence of SaaS, all under a larger claim that the people who thrive will be the ones who act as if the world is changeable.
May 3 · 1h 27m · ai, product, technology
May 3
1h 27m
ai, product, technology
№ 08
Lenny's Podcast: Product | Career | Growth · Lenny Rachitsky
Snapchat CEO: Why distribution has become the most important moat | Evan Spiegel
Evan Spiegel argues that durable consumer apps are won as much by distribution as by product-market fit, and that Snap’s survival has depended on building ecosystems and hardware that are harder to copy than software features. He describes a design culture built on relentless output, close contact with users, and a belief that AI’s future will be shaped less by technical possibility than by human acceptance.
Apr 26 · 1h 10m · technology, product, business
Apr 26
1h 10m
technology, product, business
№ 09
Lenny's Podcast: Product | Career | Growth · Lenny Rachitsky
How Anthropic’s product team moves faster than anyone else | Cat Wu (Head of Product, Claude Code)
Apr 23 · 1h 25m · ai, product, technology
Apr 23
1h 25m
ai, product, technology
№ 10
Lenny's Podcast: Product | Career | Growth · Lenny Rachitsky
Why half of product managers are in trouble | Nikhyl Singhal (Meta, Google)
Apr 19 · 1h 35m · ai, product, technology
Apr 19
1h 35m
ai, product, technology
№ 11
Lenny's Podcast: Product | Career | Growth · Lenny Rachitsky
Hard truths about building in the AI era | Keith Rabois (Khosla Ventures)
Apr 12 · 1h 22m · startup, ai, business
Apr 12
1h 22m
startup, ai, business
№ 12
Lenny's Podcast: Product | Career | Growth · Lenny Rachitsky
Anthropic’s $1B to $19B growth run: how Claude became the fastest-growing AI product in history | Amol Avasare
Apr 5 · 1h 52m · ai, business, product
Apr 5
1h 52m
ai, business, product
№ 13
Lenny's Podcast: Product | Career | Growth · Lenny Rachitsky
An AI state of the union: We’ve passed the inflection point, dark factories are coming, and automation timelines | Simon Willison
Apr 2 · 1h 39m · ai, technology, product
Apr 2
1h 39m
ai, technology, product
№ 14
Lenny's Podcast: Product | Career | Growth · Lenny Rachitsky
From skeptic to true believer: How OpenClaw changed my life | Claire Vo
Mar 29 · 1h 46m · ai, product, technology
Mar 29
1h 46m
ai, product, technology
№ 15
Lenny's Podcast: Product | Career | Growth · Lenny Rachitsky
The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack)
Mar 22 · 1h 33m · product, business, ai
Mar 22
1h 33m
product, business, ai
№ 16
Lenny's Podcast: Product | Career | Growth · Lenny Rachitsky
The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator)
Mar 15 · 1h 54m · business, psychology, technology
Mar 15
1h 54m
business, psychology, technology
№ 17
Lenny's Podcast: Product | Career | Growth · Lenny Rachitsky
How I built a 1M+ subscriber newsletter and top 10 tech podcast | Lenny Rachitsky
Mar 12 · 1h 06m · business, creativity, psychology
Mar 12
1h 06m
business, creativity, psychology
№ 18
Lenny's Podcast: Product | Career | Growth · Lenny Rachitsky
The most successful AI company you’ve never heard of | Qasar Younis
Mar 8 · 1h 24m · ai, business, technology
Mar 8
1h 24m
ai, business, technology
№ 19
Lenny's Podcast: Product | Career | Growth · Lenny Rachitsky
The design process is dead. Here’s what’s replacing it. | Jenny Wen (head of design at Claude)
Mar 1 · 1h 17m · ai, product
Mar 1
1h 17m
ai, product
№ 20
Lenny's Podcast: Product | Career | Growth · Lenny Rachitsky
AI is critical for humanity’s survival: Cisco president on the AI revolution | Jeetu Patel
Feb 26 · 1h 27m · ai, business
Feb 26
1h 27m
ai, business
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