Best Greg Isenberg Podcasts (2025)

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7 Brutal Questions for a $20B Founder 44:12

Play Pause

21m ago44:12

44:12

Get Sam's AI Executive Coach Playbook - his exact system for everything from revenue optimization to life decisions: https://clickhubspot.com/dhn Episode 778: Sam Parr ( ⁠https://x.com/theSamParr⁠ ) talks to Brian Halligan ( https://x.com/bhalligan ) about the highs and lows of building HubSpot. — Show Notes: (0:00) Are you happy? (2:57) Does it ev…

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Set Up Claude Skills in 21 Mins (for Non-Technical People)

14h ago

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In this episode, I walk through a beginner-friendly, step-by-step way to set up Claude Skills so you can get more consistent, higher-value output over time. I show where to enable Skills (it’s not on by default), how to create a new skill using Claude’s “create a skill together” flow, and why Skills are different from Projects for ongoing, reusable…

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Episode 232 - Co-Host Christmas 31:52

22h ago31:52

31:52

A short podcast this week with just the hosts talking about the contests and their favorite cartoons from the current week's issue of the New Yorker. Our scheduled guest, Shannon Wheeler had something come up at the last minute and had to drop out. We hope to have him on again sometime early in 2026. We discuss the winning entry for Contest #969 (E…

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The OpenAI Launch Nobody's Talking About (ChatGPT Skills)

3d ago

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Today I break down a big news item I think is flying under the radar: OpenAI quietly launched Skills for Codex, and I explain what that means (and how it differs from sub-agents and MCPs). I then share a fast-moving trend I’m watching and why it’s a strong wedge for a simple app. After that, I recommend the to-do app I’ve used for 14 years and give…

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How to get rich with stocks (without math, charts or models) 1:21:04

4d ago1:21:04

1:21:04

*Get Shaan's 4 money rules that took him from broke to $25M by 30:* https://clickhubspot.com/wrg Episode 777: Shaan Puri ( ⁠https://x.com/ShaanVP⁠ ) talks to Chris Camillo ( https://x.com/ChrisCamillo ) about how he turned $20K into $60M using social arbitrage investing. — Show Notes: (0:00) Intro (1:00) Turning $20K to $60M (5:30) Garage sale arbi…

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The 2025 Milly Awards! 1:41:50

7d ago1:41:50

1:41:50

Get Steph's free Digits Database with 100+ generation-defining stats: https://clickhubspot.com/stm Episode 776: Sam Parr ( ⁠https://x.com/theSamParr⁠ ) and Shaan Puri ( ⁠https://x.com/ShaanVP⁠ ) are joined by Steph Smith ( https://x.com/stephsmithio ) in this year’s LIVE Milly Awards. — Show Notes: (0:00) Welcome to the 2025 Milly Awards (1:21) Bes…

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Claude's Agent Mode was LEAKED (First Look)

8d ago

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In this episode, I go over one AI news item I can’t stop thinking about, one trend you can build a business around, two tools I’m using, one startup idea you should steal, and one framework to end on. I start with a leak suggesting Anthropic is productizing “agent mode” for Claude with structured task buckets and a progress/context UI. Then I use H…

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Episode 231 - Lawrence Wood 53:00

9d ago53:00

53:00

Larry Wood joins us on the podcast this week to talk about the recent CartoonStock contest. There was some controversy with the cartoon in this contest with a happy family gathered together in their living room, with each of the family members holding a gun (including the cat, dog and potted plant). We discuss the use of humor to help make sense of…

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Make 2026 the Best Year (Answer These 7 Questions)

11d ago

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I’m joined by Sahil Bloom for a throwback episode where he walks me through his “personal annual review,” a 7-question framework to reflect on 2025 and set yourself up to crush 2026. We talk about why reflection beats raw experience, how to use your calendar to surface what you’ve actually changed your mind on, and how to identify what creates vs. …

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25 Years of Business Advice in 27 Minutes 28:38

15d ago28:38

28:38

Steal Ryan's entire operating system: https://clickhubspot.com/gmb Episode 775: Sam Parr ( ⁠https://x.com/theSamParr⁠ ) and Shaan Puri ( ⁠https://x.com/ShaanVP⁠ ) talk to Ryan Deiss ( https://x.com/ryandeiss ) about how to create systems that run your business without you. — Show Notes: (0:00) “The More Valuable You Are, the Less Valuable the Compa…

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Episode 230 - Kate Isenberg 1:42:41

15d ago1:42:41

1:42:41

Kate Isenberg Joins us on the podcast this week. Kate is a New Yorker cartoonist, illustrator, animator and musician, but mostly she is a story teller. Along with the New Yorker, Kate's cartoons have appeared in The New Republic, Alta Journal, Air Mail, and Narrative. We talk with Kate about her background and journey to becoming a New Yorker carto…

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Prompt Claude better than 99% of people

16d ago

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In this solo episode, I walk through 10 concrete rules to get way more out of Claude Code and Claude Opus 4.5, based directly on tips Anthropic has shared in their docs and blog posts. I show how to move from vague prompts to architected briefs that use tone, constraints, structure, and power phrases to avoid “AI slop.” I demo examples across writi…

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Billionaire Lawyer spills his $250M side hustles (pick one) 1:17:00

15d ago1:17:00

1:17:00

Get the side hustle ideas database: https://clickhubspot.com/trm Episode 774: Sam Parr ( ⁠https://x.com/theSamParr⁠ ) and Shaan Puri ( ⁠https://x.com/ShaanVP⁠ ) talk to America’s richest lawyer John Morgan ( https://x.com/JohnMorganESQ ) about his fly-wheel side hustles. — Show Notes: (0:00) Intro (2:08) Wonderworks (7:00) Alcatraz East ($5M/yr) (1…

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10 Unknown SaaS Making $50K+ MRR (Copy Them)

18d ago

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On this episode I sit down with Rob Hoffman, who runs a portfolio of profitable SaaS businesses (Contact, Mentions, Kleo). Rob breaks down six proven customer acquisition playbooks using real examples doing between ~$20K and $300K MRR. The episode walks through concrete strategies like waitlist launches, trend-jacking, language arbitrage, AI search…

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if you didn't make progress in 2025, listen to the first 10 minutes 1:15:44

17d ago1:15:44

1:15:44

Get Sam's guide to turn ChatGPT into your life coach: https://clickhubspot.com/hdp Episode 773: Sam Parr ( ⁠https://x.com/theSamParr⁠ ) and Shaan Puri ( ⁠https://x.com/ShaanVP⁠ ) talk about the systems you need to hit your goals, Shaan’s new unpaid side hustle, and how to be a better communicator. — Show Notes: (0:00) 5-year journaling (2:09) The p…

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The (Improbable) Story of Savannah Bananas' Rise to a $1B Empire 1:10:52

20d ago1:10:52

1:10:52

Get the free Side Hustle Ideas Database 👉 https://clickhubspot.com/nsv Episode 772: Sam Parr ( ⁠https://x.com/theSamParr⁠ ) and Shaan Puri ( ⁠https://x.com/ShaanVP⁠ ) talk to Jesse Cole ( https://x.com/YellowTuxJesse ) the owner of Savannah Bananas and creator of Banana Ball. — Show Notes: (0:00) 200 fans, $260 in the bank (3:00) The team no one ev…

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Episode 229 - Kyle Bravo Returns 1:21:10

23d ago1:21:10

1:21:10

Kyle Bravo returns to the podcast to talk about what he's been up to since we last talked with him. He's had a couple more cartoons in the New Yorker and a number of cartoons in the Daily. He's also had cartoons in the Wall St Journal, Sat Eve Post, Antigravity, Air Mail, Alta, Private Eye, The Oldie, Woman's World, Weekly Humorist and other public…

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$50K/month Mobile App Ideas So Good You’ll Quit Your Job

23d ago

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On this episode, I breakdown eight little-known mobile apps that each generate around $50,000+ per month and explain why they work. I walk through specific examples—from AI video generators and Bible note-takers to vinyl pricing tools and AI English tutors—then explain the common patterns behind their success. The second half of the episode is devo…

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3 Simple Businesses That Make Millions 47:21

22d ago47:21

47:21

Want to start a $1M side hustle? Get 100+ ideas here: https://clickhubspot.com/gbh Episode 771: Sam Parr ( ⁠https://x.com/theSamParr⁠ ) and Shaan Puri ( ⁠https://x.com/ShaanVP⁠ ) talk about simple business ideas that are making millions. — Show Notes: (0:00) suckmyguttersclean (4:51) Hill BIlly of the Week (9:50) The MrBeast of roofing (16:02) Shaa…

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How I Use Claude Code & Cursor (Ship 10X Faster)

25d ago

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On this episode I sit down with indie app builder and designer Chris ****Raroque to walk through his real AI coding workflow. Chris explains how he ships a portfolio of productivity apps doing thousands in MRR by pairing Claude Code and Cursor instead of picking just one tool. He live-demos “vibe coding” an iOS animation, then compares how Claude C…

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Weird ways Ben Horowitz makes Founders more confident 1:12:32

24d ago1:12:32

1:12:32

Steal Sam's playbook to turn ChatGPT into your Executive Coach: https://clickhubspot.com/ohv Episode 770: Sam Parr ( ⁠https://x.com/theSamParr⁠ ) and Shaan Puri ( ⁠https://x.com/ShaanVP⁠ ) talk to Ben Horowitz ( https://x.com/bhorowitz ) about the Tupac murder, how to be a great leader, and the best opportunities for young people. — Show Notes: (0:…

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Best Products of 2025 (Apps, Video Games, AI)

1M ago

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Join me as I sit down with Jonathan Courtney to host the second annual “Sippy Awards,” the most prestigious award show in tech for the products, games, and tools that shaped 2025. We crown our most-hyped products for 2026, favorite games of the year, best productivity tools, and best products under $100. We also dive into analog tools like Traveler…

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Episode 228 - Scott Green 1:30:35

1M ago1:30:35

1:30:35

Scott Green joins us on the podcast this week. Scott was the winner of contest #962 (Octopus Pilot) and heard us on the podcast talking about it. He contacted us to see if we’d have him on to discuss the caption and his unique way of coming up with captions (it was his first time entering the contest, so his method seems to work!) Scott is also an …

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$10M Business ideas w/ The Most Interesting Guy In Tech 1:02:05

29d ago1:02:05

1:02:05

Want to start a $1M side hustle? Get 100+ ideas here: https://clickhubspot.com/gtb Episode 769: Sam Parr ( ⁠https://x.com/theSamParr⁠ ) and Shaan Puri ( ⁠https://x.com/ShaanVP⁠ ) talk to Sheel Mohnot ( https://x.com/pitdesi ) about $10M business ideas you could be early on. — Show Notes: (0:00) Intro (3:42) 50-year mortgage (11:22) #1 - AI Yard Vis…

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Reviewing Claude Opus 4.5

1M ago

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I sat down with James, the Boring Marketer, to stress-test Claude 4.5 Opus against Gemini 3 Pro for real-world coding and design work. Together we live-build and compare landing pages and clickable prototypes for an “EstateClear” probate-family dashboard, then zoom out into conversion copywriting frameworks, “elevated direct response” brand voice, …

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Build Mobile Apps that Stand Out (Here's the Playbook)

1M ago

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On this episode I sit down with indie app builder and designer Chris Raroque to break down how solo developers can make apps that truly stand out in a world of “vibe-coded” clones. Chris walks through concrete examples from his own products, Ellie (planning), Luna (budgeting), and Amy (calorie tracking), showing how small details in animations, int…

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How a $200 Doorbell Became a $4B Business 1:13:32

1M ago1:13:32

1:13:32

Get the cheat sheet: Jamie's 5 steps to build a $1B product from a $200 idea: https://clickhubspot.com/ajn Episode 768: Sam Parr ( ⁠https://x.com/theSamParr⁠ ) and Shaan Puri ( ⁠https://x.com/ShaanVP⁠ ) talk to Ring founder Jamie Siminoff ( https://x.com/JamieSiminoff ) about the wild story of building and selling Ring–plus business ideas he thinks…

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Is Gemini 3 a 10x designer? I Wanted Proof.

1M ago

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On today’s episode I stress-test Gemini 3.0 in Google AI Studio to see how good it really is as a designer, not just a code generator. Across the episode, I ask Gemini to redesign my personal website in a Windows XP–inspired style, build a restaurant analytics SaaS dashboard, and create a workout mobile app inspired by the “Brain Rot” app. Along th…

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We react to Bill Ackman's advice to young men 55:20

1M ago55:20

55:20

Get the free guide on 5 Ways to Start a Business with Less Than $1k: https://clickhubspot.com/icv Episode 767: Sam Parr ( ⁠https://x.com/theSamParr⁠ ) and Shaan Puri ( ⁠https://x.com/ShaanVP⁠ ) react to Bill Ackman’s dating advice for young men. Plus, the 20-something kid who’s making $300K/month doing man-on-the-street interviews. — Show Notes: (0…

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Episode 227 - Lawrence Wood 59:50

1M ago59:50

59:50

Larry Wood, the all time New Yorker cartoon caption contest winner, author and CartoonStock caption contest judge, joins us again to talk about the current New Yorker contests, our favorite cartoons from this week’s issue of the New Yorker and the latest CartoonStock contest. A great discussion of the contests this week. Our thoughts on the caption…

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How fortnite made me a millionaire 1:00:45

1M ago1:00:45

1:00:45

Get the Side Hustle Ideas Database [free]: https://clickhubspot.com/ckf Episode 765: Sam Parr ( ⁠https://x.com/theSamParr⁠ ) and Shaan Puri ( ⁠https://x.com/ShaanVP⁠ ) talk about every business Shaan tried before he made his first million. — Show Notes: (0:00) #1 Chipotle of Sushi (5:00) #2 Selling Wristbands Online (9:34) #3 Biotech with a billion…

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I got a private lesson on Google's NEW Gemini 3.0 AI Model

1M ago

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Get a private, on-screen walkthrough of Google’s new Gemini 3.0 with Logan Kilpatrick. We vibe-code full apps, games, and product UIs in real time. You’ll see how to go from raw idea to working product in a single prompt, then iterate visually with design, features, and AI workflows. They turn an IdeaBrowser concept into a live talent-matching plat…

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Screensharing $90M of Startup Finance Lessons in 32 Minutes

1M ago

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Master Your Cashflow (Templates Included): https://startup-ideas-pod.link/money-map On this episode, I share my simple financial operating system that helps me run my business. I share actual workflows that have saved one of my portfolio company from an 11-week runway crisis (when they thought they had 8 months), and the templates behind his 13-wee…

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Every Business I Tried Before Making My First Million 40:50

1M ago40:50

40:50

Want the Side Hustle Ideas Database? Get it here: https://clickhubspot.com/jnd Episode 765: Sam Parr ( ⁠https://x.com/theSamParr⁠ ) and Shaan Puri ( ⁠https://x.com/ShaanVP⁠ ) talk about every business Sam tried before he made his first million. — Show Notes: (0:00) #1 - Flipping Sports Equipment (2:05) #2 - Hot Dog Stand (5:42) #3 - Online Liquor S…

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How Alex Hormozi Gets Other People To Build His $100M+ Empire 1:15:55

1M ago1:15:55

1:15:55

Get Sam & Shaan's guide to build a Million Dollar Business (+team): https://clickhubspot.com/hde Episode 764: Sam Parr ( ⁠https://x.com/theSamParr⁠ ) talks to Alex Hormozi ( https://x.com/AlexHormozi ) about how to hire A+ talent, how to think in frameworks, and how to write for maximum persuasion. — Show Notes: (0:00) Hiring for general intelligen…

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One Startup Idea, One Trend, One News Debate and One Framework

2M ago

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New format, same value. I cover one startup idea, one trend, one news debate, one growth framework, one AI tool, and one product recommendation. Timestamps 00:00 – Intro 00:53 – Startup Idea 05:55 – Trend 08:17 – News Item 12:05 – Product Framework 15:31 – AI Tool 17:00 – Product Recommendation Startup Idea Solo Female Travel Safety Platform The pr…

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Episode 226 - Ed Himelblau Returns Again 55:18

2M ago55:18

55:18

This week on the podcast, we welcome back Ed Himelblau. Ed fills us in on what he's been up to since we last had him on. Turns out he moved from California to Wisconsin. The high point of the move was driving cross country in a Prius with two cats (everyone survived!) He also joins us as we discuss New Yorker Caption Contest winners for his cartoon…

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I Did Nothing For 2 Weeks. It Made Me Better At Everything. 1:06:58

1M ago1:06:58

1:06:58

Get the behind-the-scenes on Shaan’s book project - https://onehourbooks.co Get Sam's top 7 books for entrepreneurs (+ his reading strategy): https://clickhubspot.com/rkf Episode 763: Sam Parr ( ⁠https://x.com/theSamParr⁠ ) and Shaan Puri ( ⁠https://x.com/ShaanVP⁠ ) talk about the benefits of doing nothing, Shaan’s secret book project, and the $100…

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Meet the AI Agent Turning Simple Prompts into Viral Content

2M ago

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On this episode we dive deep into Glif. This beginner tutorial shows how AI agents on Glif automatically optimize prompts and workflows to create scroll-stopping content. We demo four agents live: Mr. Beast-style thumbnails, miniature documentaries, AI influencer videos, and automated Reddit story content. Total cost: $2. Timestamps: 00:00 – Intro …

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I Ranked the Best & WORST Businesses to Start Before 2026 | Andrew Wilkinson 1:20:11

2M ago1:20:11

1:20:11

Which business model should you start? Get Andrew's cheat sheet with his full ranking and real profit margins here: https://clickhubspot.com/dge Episode 762: What’s the best business to start in 2026? Agencies, SaaS, Restaurants, Real Estate, Marketplaces. Angel Investing; Andrew Wilkinson has played every game. He built 38 companies, lost $10 mill…

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Episode 225 - Anjali Chandrashekar 1:25:18

2M ago1:25:18

1:25:18

Artist, illustrator and cartoonist, Anjali Chandrashekar joins us on the second half of the podcast this week. Anjali had her first New Yorker cartoon published in the June 20, 2022 issue. She is also an accomplished artist and would love to have one of her illustrations on the cover of the New Yorker. We talk with her about being creative and her …

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The High School Dropout Who Made $2B & Bought an NBA Team 49:17

2M ago49:17

49:17

Get the guide to build your own unicorn billion dollar biz: https://clickhubspot.com/fgk Episode 761: Shaan Puri ( ⁠https://x.com/ShaanVP⁠ ) sits down with Ryan Smith ( https://x.com/ryanqualtrics ) – the high school dropout who built an $8B company and bought an NBA team. — Show Notes: (0:00) 1.9 GPA to $2B (9:47) Starting Qualtrics (14:02) Focus …

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I Ranked Every Vibe Coding App (Cursor vs Claude Code vs Lovable)

2M ago

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Micky and I rank the top vibe coding apps in 2025, from Cursor and Claude Code to Lovable, V0, Bolt, Windsurf, and emerging mobile-focused platforms. They break down which tools work best for technical developers versus non-technical builders, discuss the trust and ecosystem factors that matter when choosing a platform, and share hard-won lessons a…

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I asked Cathie Wood the question no one else will 42:33

2M ago42:33

42:33

Get the free investing playbook to invest like Warren Buffet: https://clickhubspot.com/rme Episode 760: Shaan Puri ( ⁠https://x.com/ShaanVP⁠ ) talks to Cathie Wood ( https://x.com/CathieDWood ) about her fund’s performance, her biggest bets on AI, and the most misunderstood stock on earth. — Show Notes: (0:00) McDonald’s to Managing Billions (8:54)…

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Episode 224 - Greg Nussbaum 1:30:08

2M ago1:30:08

1:30:08

Cartoonist and comedian, Greg Nussbaum joins us on the second half of the podcast this week. Greg is a fairly new cartoonist, his first cartoon in the New Yorker was in the Dec. 2, 2024 issue. Since then, he has had one other cartoon and a Daily published. Greg is also a standup comedian. You can see him performing around Brooklyn and Manhattan. We…

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Vercel CEO Shows His v0 Workflow to Build 10X Faster (& 5 $1M+ AI Startup Ideas)

2M ago

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Guillermo Rauch, CEO of Vercel and creator of Next.js, reveals exactly how he uses V0 to build products, pitch ideas, and ship features at startup speed. In this episode, he opens his personal V0 workflow, walks through the creation of his viral AI camera app (built in one afternoon), and shares a vault of free startup ideas you can build today, in…

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Masterclass: How to go from founder to CEO (without imploding) 58:29

2M ago58:29

58:29

Get Shaan's CEO Masterclass Guide: https://clickhubspot.com/esd Episode 759: Sam Parr ( ⁠https://x.com/theSamParr⁠ ) and Shaan Puri ( ⁠https://x.com/ShaanVP⁠ ) talk about the things they wish they knew when they were first-time CEOs. — Show Notes: (0:00) CEO Masterclass (38:06) Abusing Your Edge — Check Out Shaan's Stuff: • Shaan's weekly email - h…

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Claude Skills: The NEW Way to Build AI Agents (Live Tutorial)

2M ago

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In this episode, Amir takes us through how to use Claude Skills to build digital employees. We cover practical demos including an A/B testing idea agent, marketing insight analyzer, and a live build of a tweet-to-newsletter converter. You'll learn what Claude Skills actually are, why they represent the biggest leap since sub-agents, and how to buil…

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I Documented How a Viral Video Gets Made in 45 Minutes

2M ago

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Get the Blueprint to create scroll-stopping videos impossibly fast and Roberto's Core Stack: https://startup-ideas-pod.link/video-protocol Timestamps: 00:00 - Intro 03:21 - Roberto’s Recording Setup 05:00 - Script Writing Process 09:55 - Live Recording Video 13:00 - File organization system 16:12 - Editing Workflow 20:37 - Optimizing 23:17 - Incorp…

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Episode 223 - Lawrence Wood 1:07:58

2M ago1:07:58

1:07:58

Larry Wood, the all time New Yorker cartoon caption contest winner, author and CartoonStock caption contest judge, joins us again to talk about the current New Yorker contests, our favorite cartoons from this week’s issue of the New Yorker and the latest CartoonStock contest. A lively discussion of the contests this week! Humor is definitely subjec…