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Best podcasts · Updated October 2026

The 15 best podcasts like Lenny's Podcast, ranked

Finished Lenny's back catalog, or want the same depth from different voices? These shows bring the same kind of operators and the same specific, how-it-actually-worked conversations about product, growth, AI and careers. Ranked for how close they come.

We did not rank these from memory. TL;WL has transcribed 978 episodes of 7 of these shows to build its research library, so we know what each one actually covers.

Have a burning business question no single episode answers?Ask TL;WL. It searches what the guests of these 15 shows and hundreds more founders and operators actually said, and makes you one episode on your question.
1

How I AI

Claire Vo (founder of ChatPRD; has been chief product officer at LaunchDarkly, Color and Optimizely)

screen-share interviews and solo tool reviews · 25-45 min · about twice a week · since 2025

Why it is #1: Each episode ends with something you can try the same day, and the guests show the actual workflow instead of describing it.

What it is like: A guest shares their screen and walks through one AI workflow step by step, or Claire tests new tools herself. It is closer to a live tutorial than a talk show. Part of the Lenny's Podcast network.

4.8
Apple Podcasts rating (US) from 255 ratings
Apple Podcasts show page, 2026-10-31

Bring it questions like

  • How can I use Claude Code or Cursor to prototype as a PM without being an engineer?
  • What does a real AI workflow for writing PRDs look like?
  • How did other companies roll out AI coding tools across their teams?
  • Which new AI model or agent is worth switching to this month?

Start with

  • No Figma. No Jira. No docs. How Gusto built a new product line with Claude Code | Eddie Kim (CTO). A concrete case of a team building a product without the usual PM artifacts.
  • Why Reddit built its own AI prototyping tool | Blair Metcalf. Shows how a large product org changed the way it prototypes.

Newsletter: Lenny's Newsletter, 1,200,000+ subscribers (lennysnewsletter.com ("Over 1,200,000 subscribers"))

Best for: PMs who want to use AI tools hands-on in their own work

Skip it if: You want strategy and leadership topics; this show is about tools and workflows. Note the host also runs ChatPRD, an AI tool for PMs.

2

The Skip Podcast

Nikhyl Singhal (founder of Skip, a career coaching service for product people; former CPO at Credit Karma and product executive at Meta and Google)

career-focused conversations and panels · 55-65 min · every two weeks · since 2023

Why it is #2: Career advice for PMs is usually generic; this show gives specific frameworks for job moves, promotions and negotiation from someone who has hired and coached hundreds of product leaders.

What it is like: Nikhyl talks through career decisions with product leaders and recruiters, drawn from real coaching conversations. Calm, structured, and focused on what to do next in your career.

5.0
Apple Podcasts rating (US) from 74 ratings
Apple Podcasts show page, 2026-10-31
5.54K
YouTube subscribers
The Skip YouTube channel, 2026-10-31
53
episodes in the TL;WL library
median 52 min, 18 new in the last year

Bring it questions like

  • Should I stay at my company or leave for a better role?
  • What does it take to get hired as a PM at an AI lab like Anthropic?
  • Why did I get passed over for promotion to group PM?
  • How is the PM job market changing, and what should I do about it?

Start with

  • The PM career framework for AI. Lays out how PM career paths are splitting as AI changes the role; the start of a three-part series.
  • Should you Stay or Go? A 5-factor framework for career-defining decisions. A reusable checklist for the most common career question PMs face.

Newsletter: The Skip, 27,000+ subscribers (The Skip Substack homepage ("Over 27,000 subscribers"))

Best for: Senior PMs and product leaders planning their next career move

Skip it if: You want craft topics like discovery or roadmapping; this is almost entirely about careers.

3

Supra Insider

Marc Baselga (co-founder of Insider Loops, a PM interview and career coaching company). Ben Erez (co-founder of Insider Loops)

two co-hosts plus a guest · 60-80 min · weekly · since 2024

Why it is #3: It covers the parts of a PM career that other shows skip: interview loops, take-homes, offers and negotiation, with current detail from people who hire.

What it is like: Two hosts talk through hiring, interviewing and careers for product people, often with a recruiter or hiring manager as guest. Conversational and specific about how hiring actually works.

5.0
Apple Podcasts rating (US) from 10 ratings
Apple Podcasts show page, 2026-10-31
127
episodes in the TL;WL library
median 66 min, 47 new in the last year

Bring it questions like

  • How do I approach a PM take-home assignment?
  • How do I negotiate comp for a PM role at OpenAI or Anthropic?
  • What are behavioral interviews at AI labs looking for now?
  • Should I join an early-stage startup as the first PM?

Start with

  • #131: Inside comp negotiation for PM roles at top companies like OpenAI and Anthropic | Colin Lernell (Co-founder @ Valued). Concrete negotiation advice for top-paying PM roles.
  • #57: What product leaders get wrong about strategy | Melissa Perri (board member, author of Escaping The Build Trap). One of the show's strongest craft episodes, with a well-known guest.

Newsletter: Supra Insider, 3,000+ subscribers (Supra Insider Substack homepage ("Over 3,000 subscribers"))

Best for: PMs who are job hunting or preparing for interviews

Skip it if: You are happy in your role and want craft or strategy content.

4

In Depth

Brett Berson (partner at First Round Capital)

long-form interviews · 60-70 min · every few weeks · since 2020

Why it is #4: The interviews go further into the reasoning behind decisions than most, and the product leader episodes are some of the best available.

What it is like: Brett interviews founders, CPOs and other executives and keeps pulling for the tactical detail behind their decisions. Many product leaders from companies like Figma, Linear, Stripe and Xero.

4.8
Apple Podcasts rating (US) from 60 ratings
Apple Podcasts show page (US store), 2026-10-31
30.7K
YouTube subscribers (First Round Capital channel)
First Round Capital YouTube channel, 2026-10-31

Bring it questions like

  • Should I stop obsessing over the roadmap, and what should I focus on instead?
  • How did Linear keep its focus on craft as it grew?
  • What makes or breaks an executive hire?
  • How did a company find product-market fit after a pivot?

Start with

  • Why great product leaders should stop obsessing over the roadmap | Diya Jolly (CPO & CTO of Xero). A CPO's case for what matters more than the roadmap.
  • Inside Linear: Why craft and focus still win in product building | Karri Saarinen (Co-founder and CEO). A detailed look at how one of the most admired product teams works.

Newsletter: The First Round Review, 200K+ subscribers (First Round Review site ("Why 200K+ readers subscribe to The Review"))

Best for: Senior product leaders and founders

Skip it if: You are early in your PM career; many episodes are about running a company.

5

The Growth Podcast

Aakash Gupta (writes the Product Growth newsletter; former VP of Product at Apollo.io)

long-form interviews and masterclasses · 60-75 min · about weekly · since 2024

Why it is #5: The masterclass episodes are among the most detailed free walkthroughs of pricing, growth loops and AI product work.

What it is like: Mix of guest interviews and long how-to sessions on pricing, growth and AI product work. Detailed and fast, aimed at PMs who want to level up.

4.6
Apple Podcasts rating (US) from 36 ratings
Apple Podcasts show page, 2026-10-31

Bring it questions like

  • How should I price a SaaS product?
  • How do I set up evals for an AI feature?
  • How do I become a product builder who ships prototypes with AI?
  • How do I think about product strategy now that AI changes the cost of building?

Start with

  • Pricing Masterclass: Everything you need to know about SaaS Pricing. The first episode and a complete primer on SaaS pricing.
  • Evals are the new PRD. Here is the playbook with the CEO of the leader in the space (Ankur Goyal, Founder and CEO, Braintrust). A practical guide to evals, now a core skill for AI PMs.

Newsletter: Product Growth, 500K+ subscribers (the show's own description in its podcast feed ("Join 500K+"))

Best for: PMs focused on growth, pricing and AI products

Skip it if: You prefer slower, reflective conversations; episodes are dense and frequently tool-focused.

Have a burning business question no single episode answers?Ask TL;WL. It searches what the guests of these 15 shows and hundreds more founders and operators actually said, and makes you one episode on your question.
6

Behind the Craft

Peter Yang (writes the Behind the Craft newsletter; has led product teams at Roblox, Reddit, Twitch and Meta)

interviews and live tutorials · 35-50 min · weekly · since 2024

Why it is #6: It regularly gets builders from AI companies such as Anthropic and Cursor to show their workflows step by step.

What it is like: Peter interviews people building with AI, often with a live demo of how they work. Recent episodes range from AI agents and coding workflows to personal finance and parenting uses of AI.

4.6
Apple Podcasts rating (US) from 11 ratings
Apple Podcasts show page, 2026-10-31
114K
YouTube subscribers (Peter Yang's channel, where the show is published)
YouTube channel @PeterYangYT, 2026-10-31

Bring it questions like

  • How do I vibe code an app that can become a real product?
  • How does Anthropic actually build Claude?
  • What is a good agentic engineering workflow for shipping apps?
  • How do I go from design to code with Cursor?

Start with

  • Inside Anthropic: How Claude Actually Gets Built | Alex Albert. An inside look at how an AI lab builds and ships its product.
  • Full Tutorial: Design to Code in 45 Min with Cursor's Head of Design | Ryo Lu. A complete walkthrough you can follow along with.

Newsletter: Behind the Craft, 140K+ subscribers (creatoreconomy.so/about ("helps 140K+ tech professionals"))

Best for: PMs who want to build things themselves with AI tools

Skip it if: You want classic PM topics like roadmaps, discovery or stakeholder management.

7

The Product Experience

Lily Smith (product consultant and long-time host for Mind the Product). Randy Silver (product leader and trainer, co-host for Mind the Product)

interviews · 35-50 min · weekly · since 2018

Why it is #7: Eight years of weekly episodes on core PM practice, with many guests who work on normal-sized teams rather than only famous companies.

What it is like: Two hosts interview one product person per episode, often speakers from Mind the Product and ProductTank events. Practical, friendly, and a manageable length.

4.7
Apple Podcasts rating (US) from 35 ratings
Apple Podcasts show page, 2026-10-31
181
episodes in the TL;WL library
median 38 min, 47 new in the last year

Bring it questions like

  • How do I fix a roadmap that has turned into a feature list?
  • What is AI product management, and how is it different from regular PM work?
  • How do I escape the feature factory?
  • What do companies get wrong about product discovery?

Start with

  • Vision and strategy - Marty Cagan on The Product Experience - Part 1. A clear explanation of product vision and strategy from the author of Inspired.
  • What companies get wrong about product discovery - Frances Ibe (SVP of Product, Tide). Popular enough that the show re-ran it in 2025.

Newsletter: Mind the Product newsletter, 170k+ subscribers (Mind the Product newsletter page title ("Product Management Newsletter (170k+ Subscribers)"))

Best for: Working PMs who want steady, practical craft advice

Skip it if: You want long, deep-dive interviews with well-known founders.

8

Just Now Possible

Teresa Torres (author of Continuous Discovery Habits; runs Product Talk)

case-study interviews with AI product teams · 60-75 min · every two weeks, with gaps · since 2025

Why it is #8: Each episode is a full case study of a shipped AI feature, which is hard to find anywhere else.

What it is like: Teresa interviews the team behind one AI product and goes through how they found the problem, prototyped, built evals and shipped. Technical in places.

5
Apple Podcasts rating (US) from 5 ratings
Apple Podcasts show page, 2026-10-31

Bring it questions like

  • How do teams design evals for an AI feature?
  • When should I use agents, RAG or a simple prompt?
  • How did other teams go from AI prototype to shipped feature?
  • How do I build trust and safety into an AI product?

Start with

  • Building Lorikeet: How AI Humility and a Dual-Agent Architecture Are Redefining Customer Support. A clear example of an AI product designed around knowing its limits.
  • Creating Aha! Builder: Concept to Code, No Engineers Required. How an established product company built an AI app builder.

Newsletter: Product Talk

Best for: PMs building AI features

Skip it if: You do not work on AI products; the episodes assume interest in architecture and evals.

9

The Exit Five Podcast

Dave Gerhardt (founder of Exit Five, the B2B marketing community; former CMO at Drift). Dan Murphy and Exit Five team (dan Murphy is CEO of Exit Five and appears on company episodes; other episodes are hosted by the Exit Five team and guest marketers)

interviews with B2B marketers, plus solo 'Dave Unfiltered' episodes, live session recordings and 'Best of B2B' replays · 35-55 min · several episodes a week · since 2021

Why it is #9: Every episode is about the job of a B2B marketer: programs, team structure, budgets and career moves. Guests are practitioners from companies like Snowflake rather than celebrity speakers.

What it is like: Working B2B marketers explain how they ran a specific program, such as ABM, webinars or content, in plain talk. The tone is casual and practical.

4.6
Apple Podcasts rating (US) from 50 ratings
Apple Podcasts, 2026-10-31
7,000+
Community members B2B marketers
Exit Five homepage, 2026-10-31
250
episodes in the TL;WL library
median 48 min, 98 new in the last year

Bring it questions like

  • How do I run B2B webinars that actually produce pipeline?
  • What should an ABM program look like now that buying groups are bigger?
  • How do I build a content strategy my CEO will back?
  • How do I market with a small team and not chase every channel?

Start with

  • Why You Should Slow Down and Market Intentionally to Make an Impact (with Ann Handley). Ann Handley on doing fewer, better marketing programs, a useful counterweight to volume-driven content plans.
  • Top 5 B2B Webinar Mistakes (and How to Fix Them) with Logan Lyles, DemandShift. A concrete checklist episode you can apply to your next webinar.

Newsletter: Exit Five newsletter, 40,000+ subscribers (Exit Five website)

Best for: B2B and SaaS marketers from first hire to CMO

Skip it if: You work in B2C or ecommerce and want consumer growth tactics.

10

A Product Market Fit Show

Pablo Srugo

long-form interviews with founders about their 0 to 1 stage · 45-60 min · weekly · since 2022

Why it is #10: It sticks to one subject, the path to product-market fit, and gets founders of companies like Reddit, Gusto, Glean and Huntress to give specifics about their earliest stage.

What it is like: Each founder explains the period before and around product-market fit: early customers, failed versions, pivots and the first sales. The host keeps pulling the story back to what changed and why.

5.0
Apple Podcasts rating (US) from 86 ratings
Apple Podcasts US show page, 2026-10-31
302
episodes in the TL;WL library
median 43 min, 69 new in the last year

Bring it questions like

  • How do I tell if I actually have product-market fit?
  • How did other founders get their first enterprise customers?
  • Should I charge from day one or give the product away to get traction?
  • What do founders do when a free product spreads but nobody uses it?

Start with

  • WebSummit Panel w/ Founders of Glean ($5B) and Huntress ($2B): What it takes to hit $100M ARR. Two founders compare how they went from early fit to scale.

Best for: Pre-seed to Series A founders still searching for fit

Skip it if: You already have strong fit and want scaling, hiring or exit advice.

11

Acquired

Ben Gilbert (co-founder and co-host of Acquired, former software engineer and venture capitalist). David Rosenthal (co-founder and co-host of Acquired, former venture capitalist)

two co-hosts telling the full history of one company · 3-4.5 hours · about once a month (Apple lists it as biweekly) · since 2015

Why it is #11: It explains business models, pricing and competitive advantage through real company histories, which helps you reason about your own company's position.

What it is like: Two hosts walk through one company from founding to today, then break down why it won. Episodes are long and heavily researched.

over 1 million
listeners per episode
Acquired about page (self-reported), 2026-10-31
4.7
Apple Podcasts rating from 5,483 ratings
Apple Podcasts show page, 2026-10-31
62
episodes in the TL;WL library
median 91 min, 11 new in the last year

Bring it questions like

  • Why does Costco's membership model let it run on such thin margins?
  • How did Home Depot build its advantage over other hardware retailers?
  • What decisions turned a small company into the market leader?
  • How do great companies treat their suppliers?

Start with

  • Costco. Explains membership economics, low SKU count and supplier relationships in detail.
  • The Home Depot. A recent episode on how a retailer built and kept an operational advantage.

Best for: Founders and senior operators who think about strategy and competition

Skip it if: You want quick tactics; episodes run three to four hours and come out roughly monthly.

12

Unsolicited Feedback

Brian Balfour (founder of Reforge; former VP of Growth at HubSpot). Fareed Mosavat (formerly at Reforge and Slack)

No new episodes lately, archive still worth it

two co-hosts talking, sometimes with a guest · 40-50 min · stopped; last episode 14 October 2025 · since 2023

Why it is #12: The analysis of growth loops and distribution is still some of the sharpest available, but treat it as an archive: the show has not published in over a year.

What it is like: Two growth experts break down recent product launches and strategy moves at companies like OpenAI, LinkedIn and Google. No new episodes since October 2025.

4.7
Apple Podcasts rating (US) from 44 ratings
Apple Podcasts show page, 2026-10-31

Bring it questions like

  • Are moats dead now that AI makes products easy to copy?
  • How do AI companies use growth loops?
  • How is distribution changing because of AI?
  • What can I learn from LinkedIn's gamification?

Start with

  • OpenAI’s Land Grab: Are Moats Dead? How Startups Can Still Differentiate - Unsolicited Feedback S3E7. A clear framework for thinking about differentiation in AI.
  • Adam Nash Explores the Art of Process-Strategy Fit at eBay and LinkedIn, with a Side of Diet Coke and Legos. A useful idea on matching process to strategy, from a former LinkedIn and eBay product leader.

Best for: Growth PMs and product strategists

Skip it if: You want current news; the most recent episode is from October 2025.

13

Product Talk

Products That Count (A nonprofit for product managers; each episode has a product leader interviewing another product leader)

interviews · 30-40 min · about twice a week · since 2015

Why it is #13: It covers industries most PM shows ignore, such as health, hardware and enterprise software, with new episodes twice a week.

What it is like: Short interviews with CPOs and product leads from companies such as Carta, IBM, WHOOP and DoorDash, including a CPO Rising series. Not the same as Teresa Torres's Product Talk.

5.0
Apple Podcasts rating (US) from 45 ratings
Apple Podcasts show page, 2026-10-31

Bring it questions like

  • What makes a PM stand out as AI handles more of the work?
  • How does a CPO build the case for a bet no customer asked for?
  • How do product leaders think like business operators?
  • How do PMs at hardware or health companies work differently?

Start with

  • CPO Rising Series: Carta CPO on Why Knowing What to Build Matters More Than Ever. A clear take on how deciding what to build matters more as building gets cheaper.
  • The Conviction Bet No Customer Asked For and How Asana's CPO Builds the Case for One. Practical advice on getting support for a product bet.

Best for: PMs who want a wide range of industries and company types

Skip it if: You want a consistent host voice or very deep episodes.

14

One Knight in Product

Jason Knight (product consultant who runs One Knight Consulting)

long-form interviews · 50-70 min · every two to three weeks · since 2020

Why it is #14: It has interviewed most of the major PM authors, including Marty Cagan, Teresa Torres, April Dunford and John Cutler, and Jason challenges them instead of just agreeing.

What it is like: Jason asks hard but fair questions, with dry British humour, and mixes well-known authors with working practitioners. Less hype than most PM shows.

4.7
Apple Podcasts rating (US) from 14 ratings
Apple Podcasts show page, 2026-10-31
3
episodes in the TL;WL library
median 39 min, 15 new in the last year

Bring it questions like

  • Does AI actually change product management fundamentals?
  • How do I move my company to the product operating model?
  • Why do PMs need to understand the company's financials?
  • How do I fix positioning for a B2B product?

Start with

  • Jeff Patton: AI Doesn't Change Product Management Fundamentals. A grounded counterpoint to the AI hype, from the author of User Story Mapping.
  • Transforming your Organisation to the Product Operating Model (with Marty Cagan, Author "Inspired", "Empowered" and "Transformed"). Cagan explains the product operating model and Jason presses him on how it works in practice.

Newsletter: One Knight in Product

Best for: Experienced PMs who want critical discussion of popular PM ideas

Skip it if: You want quick tactical tips on a weekly schedule.

15

Y Combinator Startup Podcast

YC partners (Garry Tan, Harj Taggar, Diana Hu, Jared Friedman and others)

mix: partner discussions (Lightcone), founder talks and interviews, how-to episodes · 15-60 min · about weekly, often several episodes a week · since 2017

Why it is #15: YC partners see more early-stage companies than almost anyone, and the how-to episodes turn that into specific advice. The Lightcone episodes give a regular read on where early-stage startups are heading.

What it is like: A mix of YC partners discussing what they see across hundreds of startups, short how-to episodes (sales, ideas, launch videos), and interviews with well-known founders. Strong AI focus in 2026.

4.5
Apple Podcasts rating (US) from 220 ratings
Apple Podcasts US show page, 2026-10-31
2.43M
YouTube subscribers
YouTube channel page, 2026-10-31

Bring it questions like

  • How do I pick a startup idea?
  • How do I improve my outbound sales as an early founder?
  • What should a launch video for my startup look like?
  • What is changing for startups now that anyone can build software with AI?

Start with

  • How To Pick A Startup Idea. YC's standard advice on choosing what to work on.
  • 8 Ways To Improve Your Outbound Sales. Short and directly usable for founders doing their own sales.

Best for: Venture-track founders, especially technical founders building with AI

Skip it if: You are building a small bootstrapped business and want profit-first advice.

How we ranked them

Practical depth first: does an episode leave you with something you can use at work on Monday? Then the quality of the hosts and guests, whether the show is still publishing, and how consistent it is. Fame counts for little. Listener numbers are shown only when the show or a credible source has published them, with a link to where; we never estimate them. Facts were checked in October 2026.

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