--- schema: 1 type: video title: How Gumroad's CEO uses ChatGPT - Ep. 1 with Sahil Lavingia description: >- I believe that ChatGPT is the most important creative tool of the decade. I think it can help us write better, create art, efficiently ship products, build great businesses, make smart decisions, and even learn something about ourselves,. But it’s still so early. Most of us don’t even really know how to use ChatGPT. We have a feeling that it’s powerful, interesting, and important—but we haven’t figured out how to incorporate it into our lives. There are a few people, though, who are living in the future. They have the time and curiosity to use ChatGPT in their everyday lives, taking the opportunity to make the technology work for them. In this way, they light the way for everyone else. That’s what this interview series, How I Use ChatGPT, is all about. We go in-depth with the most interesting people in the world to learn concrete ways they are already using ChatGPT. It won’t be theoretical—or limited to audio: we’ll screen-share and see their actual prompts and responses, so you can see how ChatGPT helps them perform better at work and improve their lives—one conversation at a time. About this episode: My first guest is Sahil Lavingia https://twitter.com/shl the co-founder and CEO of Gumroad https://gumroad.com one of the largest platforms for creators to sell their work online. He shared how he uses ChatGPT for: Buying a building. He wants to buy a New York City hangout for Gumroad employees and customers, so he asked ChatGPT to research the history of real estate in NYC, suggest which neighborhoods might be best to target, generate questions for brokers, and even detail what the design of a particular property might look like. Writing tweets. Sahil is a prolific Twitter/X user. He often uses ChatGPT to help him flesh out an idea. He says, “I [start] with a tweet, which is like a thesis, and then I just say, ‘Add three to four paragraphs to make the point compelling—also suggest more examples.’” We explore his precise process for using ChatGPT to help him brainstorm short tweets and longer essays in this episode. Pressure-testing ideas. For Sahil, ChatGPT is like upgrading his peripheral vision. It lets him see around the corners, ask better questions of himself and other people, and avoid poor decisions. He told me, “I think a lot of people sort of delude themselves into thinking they have [good ideas]… I think that one of the most useful things about [ChatGPT] is it focuses your research on what actually matters.” For Sahil, it’s the ultimate tool to help him think better. Also in this episode: how ChatGPT could have helped Sahil save $70 million, how he thinks it will improve the most-talented creatives, and why he thinks—in the age of AI—people have no excuse for not knowing the answer to something anymore. Want even more? Sign up for Dan’s newsletter Every to unlock our ultimate guide to prompting ChatGPT. It’s usually only for paying subscribers, but you can get it here for free: https://every.ck.page/ultimate-guide-to-prompting-chatgpt To hear more from Dan Shipper: Subscribe to Every: https://every.to/subscribe Follow him on X: https://twitter.com/danshipper Register for his course, Maximize Your Mind With ChatGPT: https://www.maxyourmind.xyz/ Timestamps: 00:00:00 - Teaser 00:00:33 - Intro 00:02:00 - There’s no more excuse for not knowing anymore 00:02:50 - He doesn’t spend as much time on bad ideas 00:06:15 - How ChatGPT will make the top 1% of creative output better 00:08:20 - How it turbocharges research 00:11:00 - How he’s using ChatGPT to buy a building 00:17:43 - How he uses ChatGPT to pressure-test ideas 00:20:50 - How he uses DALL-E to help with interior design 00:26:00 - How ChatGPT could have saved him $70 million 00:29:50 - How he uses ChatGPT in his decision-making 00:38:00 - How he uses ChatGPT for writing canonical: >- https://liquidgold.cc/channel/everyinc/explore/video/how-gumroad-s-ceo-uses-chatgpt-ep-1-with-sahil-lavi-d8ba7f04567e markdown: >- https://liquidgold.cc/channel/everyinc/video/how-gumroad-s-ceo-uses-chatgpt-ep-1-with-sahil-lavi-d8ba7f04567e.md llms: null parent: 'https://liquidgold.cc/channel/everyinc.md' channel: everyinc updated: '2026-10-24T01:41:55.273Z' language: null children: [] videoId: SOxYgUIVq6g durationSeconds: 2822 publishedAt: '2023-11-15T15:43:10.000Z' searchChunks: - ordinal: 0 text: null startSeconds: 34 endSeconds: 45 watch: 'https://liquidgold.cc/watch/SOxYgUIVq6g?t=34' heldReason: rights - ordinal: 1 text: null startSeconds: 133 endSeconds: 174 watch: 'https://liquidgold.cc/watch/SOxYgUIVq6g?t=133' heldReason: rights - ordinal: 2 text: null startSeconds: 184 endSeconds: 385 watch: 'https://liquidgold.cc/watch/SOxYgUIVq6g?t=184' heldReason: rights - ordinal: 3 text: null startSeconds: 184 endSeconds: 385 watch: 'https://liquidgold.cc/watch/SOxYgUIVq6g?t=184' heldReason: rights - ordinal: 4 text: null startSeconds: 184 endSeconds: 385 watch: 'https://liquidgold.cc/watch/SOxYgUIVq6g?t=184' heldReason: rights - ordinal: 5 text: null startSeconds: 385 endSeconds: 395 watch: 'https://liquidgold.cc/watch/SOxYgUIVq6g?t=385' heldReason: rights - ordinal: 6 text: null startSeconds: 395 endSeconds: 509 watch: 'https://liquidgold.cc/watch/SOxYgUIVq6g?t=395' heldReason: rights - ordinal: 7 text: null startSeconds: 519 endSeconds: 660 watch: 'https://liquidgold.cc/watch/SOxYgUIVq6g?t=519' heldReason: rights - ordinal: 8 text: null startSeconds: 660 endSeconds: 671 watch: 'https://liquidgold.cc/watch/SOxYgUIVq6g?t=660' heldReason: rights - ordinal: 9 text: null startSeconds: 671 endSeconds: 759 watch: 'https://liquidgold.cc/watch/SOxYgUIVq6g?t=671' heldReason: rights - ordinal: 10 text: null startSeconds: 769 endSeconds: 856 watch: 'https://liquidgold.cc/watch/SOxYgUIVq6g?t=769' heldReason: rights - ordinal: 11 text: null startSeconds: 856 endSeconds: 867 watch: 'https://liquidgold.cc/watch/SOxYgUIVq6g?t=856' heldReason: rights - ordinal: 12 text: null startSeconds: 1066 endSeconds: 1076 watch: 'https://liquidgold.cc/watch/SOxYgUIVq6g?t=1066' heldReason: rights - ordinal: 13 text: null startSeconds: 1076 endSeconds: 1257 watch: 'https://liquidgold.cc/watch/SOxYgUIVq6g?t=1076' heldReason: rights - ordinal: 14 text: null startSeconds: 1076 endSeconds: 1257 watch: 'https://liquidgold.cc/watch/SOxYgUIVq6g?t=1076' heldReason: rights - ordinal: 15 text: null startSeconds: 1076 endSeconds: 1257 watch: 'https://liquidgold.cc/watch/SOxYgUIVq6g?t=1076' heldReason: rights - ordinal: 16 text: null startSeconds: 1267 endSeconds: 1369 watch: 'https://liquidgold.cc/watch/SOxYgUIVq6g?t=1267' heldReason: rights - ordinal: 17 text: null startSeconds: 1381 endSeconds: 1479 watch: 'https://liquidgold.cc/watch/SOxYgUIVq6g?t=1381' heldReason: rights - ordinal: 18 text: null startSeconds: 1490 endSeconds: 1570 watch: 'https://liquidgold.cc/watch/SOxYgUIVq6g?t=1490' heldReason: rights - ordinal: 19 text: null startSeconds: 1581 endSeconds: 1793 watch: 'https://liquidgold.cc/watch/SOxYgUIVq6g?t=1581' heldReason: rights - ordinal: 20 text: null startSeconds: 1805 endSeconds: 1895 watch: 'https://liquidgold.cc/watch/SOxYgUIVq6g?t=1805' heldReason: rights - ordinal: 21 text: null startSeconds: 1906 endSeconds: 2006 watch: 'https://liquidgold.cc/watch/SOxYgUIVq6g?t=1906' heldReason: rights - ordinal: 22 text: null startSeconds: 2017 endSeconds: 2147 watch: 'https://liquidgold.cc/watch/SOxYgUIVq6g?t=2017' heldReason: rights - ordinal: 23 text: null startSeconds: 2017 endSeconds: 2147 watch: 'https://liquidgold.cc/watch/SOxYgUIVq6g?t=2017' heldReason: rights - ordinal: 24 text: null startSeconds: 2159 endSeconds: 2283 watch: 'https://liquidgold.cc/watch/SOxYgUIVq6g?t=2159' heldReason: rights - ordinal: 25 text: null startSeconds: 2159 endSeconds: 2283 watch: 'https://liquidgold.cc/watch/SOxYgUIVq6g?t=2159' heldReason: rights - ordinal: 26 text: null startSeconds: 2385 endSeconds: 2513 watch: 'https://liquidgold.cc/watch/SOxYgUIVq6g?t=2385' heldReason: rights - ordinal: 27 text: null startSeconds: 2523 endSeconds: 2617 watch: 'https://liquidgold.cc/watch/SOxYgUIVq6g?t=2523' heldReason: rights - ordinal: 28 text: null startSeconds: 2628 endSeconds: 2715 watch: 'https://liquidgold.cc/watch/SOxYgUIVq6g?t=2628' heldReason: rights --- # How Gumroad's CEO uses ChatGPT - Ep. 1 with Sahil Lavingia I believe that ChatGPT is the most important creative tool of the decade. I think it can help us write better, create art, efficiently ship products, build great businesses, make smart decisions, and even learn something about ourselves,. But it’s still so early. Most of us don’t even really know how to use ChatGPT. We have a feeling that it’s powerful, interesting, and important—but we haven’t figured out how to incorporate it into our lives. There are a few people, though, who are living in the future. They have the time and curiosity to use ChatGPT in their everyday lives, taking the opportunity to make the technology work for them. In this way, they light the way for everyone else. That’s what this interview series, How I Use ChatGPT, is all about. We go in-depth with the most interesting people in the world to learn concrete ways they are already using ChatGPT. It won’t be theoretical—or limited to audio: we’ll screen-share and see their actual prompts and responses, so you can see how ChatGPT helps them perform better at work and improve their lives—one conversation at a time. About this episode: My first guest is Sahil Lavingia https://twitter.com/shl the co-founder and CEO of Gumroad https://gumroad.com one of the largest platforms for creators to sell their work online. He shared how he uses ChatGPT for: Buying a building. He wants to buy a New York City hangout for Gumroad employees and customers, so he asked ChatGPT to research the history of real estate in NYC, suggest which neighborhoods might be best to target, generate questions for brokers, and even detail what the design of a particular property might look like. Writing tweets. Sahil is a prolific Twitter/X user. He often uses ChatGPT to help him flesh out an idea. He says, “I \[start] with a tweet, which is like a thesis, and then I just say, ‘Add three to four paragraphs to make the point compelling—also suggest more examples.’” We explore his precise process for using ChatGPT to help him brainstorm short tweets and longer essays in this episode. Pressure-testing ideas. For Sahil, ChatGPT is like upgrading his peripheral vision. It lets him see around the corners, ask better questions of himself and other people, and avoid poor decisions. He told me, “I think a lot of people sort of delude themselves into thinking they have \[good ideas]… I think that one of the most useful things about \[ChatGPT] is it focuses your research on what actually matters.” For Sahil, it’s the ultimate tool to help him think better. Also in this episode: how ChatGPT could have helped Sahil save $70 million, how he thinks it will improve the most-talented creatives, and why he thinks—in the age of AI—people have no excuse for not knowing the answer to something anymore. Want even more? Sign up for Dan’s newsletter Every to unlock our ultimate guide to prompting ChatGPT. It’s usually only for paying subscribers, but you can get it here for free: https://every.ck.page/ultimate-guide-to-prompting-chatgpt To hear more from Dan Shipper: Subscribe to Every: https://every.to/subscribe Follow him on X: https://twitter.com/danshipper Register for his course, Maximize Your Mind With ChatGPT: https://www.maxyourmind.xyz/ Timestamps: 00:00:00 - Teaser 00:00:33 - Intro 00:02:00 - There’s no more excuse for not knowing anymore 00:02:50 - He doesn’t spend as much time on bad ideas 00:06:15 - How ChatGPT will make the top 1% of creative output better 00:08:20 - How it turbocharges research 00:11:00 - How he’s using ChatGPT to buy a building 00:17:43 - How he uses ChatGPT to pressure-test ideas 00:20:50 - How he uses DALL-E to help with interior design 00:26:00 - How ChatGPT could have saved him $70 million 00:29:50 - How he uses ChatGPT in his decision-making 00:38:00 - How he uses ChatGPT for writing Canonical: https://liquidgold.cc/channel/everyinc/explore/video/how-gumroad-s-ceo-uses-chatgpt-ep-1-with-sahil-lavi-d8ba7f04567e · Channel: [Every](https://liquidgold.cc/channel/everyinc.md) > Search chunk text is held until public-source provenance is verified. ## Document chunks > Missing: no stored document chunks are available.