531,000 people read Lenny Rachitsky’s newsletter every week. He started in 2019 with zero writing experience, so what’s his secret? I asked him about writing well, growing a newsletter, and building an ultra-profitable business around creative work. 10 key takeaways: 1. What do people ask you about that you don't have a great answer to? Viral essays are hiding inside this question. If people keep asking you the same question and nobody's written the answer, take on the challenge yourself. 2. Don’t let the size of the internet stun you into inaction. Most of the content out there sucks. Lenny: “If you could just do something better than what's out there, you can rise above the noise.” 3. Lenny’s mantra: “Service instead of self-gain.” Great things happen when you just try to be consistently helpful. No growth hack beats providing real value to people. 4. The world suffers from a scarcity of well-formulated questions from inquisitive people. Lenny has worked in tech for over a decade, and he’s still surprised by how open people are to answering questions and revealing “trade secrets.” 5. Long introductions are a rookie mistake. Save your readers time and jump right into the answer. 6. How to edit: While editing other people (and himself), Lenny asks: “What is interesting to me? Where do I get lost?” Notice where your attention spikes and sags. Your own brain is a great proxy for what people will find interesting (and where they’ll doze off.) 7. You should know what you don’t want to do as clearly as what you want to do. Lenny: “I'm actively not trying to build an empire. I'm actively trying not to build a media company.” 8. Lenny’s first essay went bonkers-viral, partially because of the brilliant headline: “What Seven Years at Airbnb Taught Me About Building a Business.” Let's break it down. “Seven years” gives him credibility, “Airbnb” piques interest, and “about building a business” tells people they can expect actionable takeaways. 9. If you want to have an existential breakdown, try to make each sentence an aesthetic masterpiece. Ditch the poetry and focus on clarity instead. Lenny: “Every time I think about how to write beautifully, I just get stuck, and it just slows everything down.” 10. When in doubt, make it useful: If you want to be widely read, try to solve people’s problems. The peskier the problem, and the more useful your solution, the further your writing will spread.
Hi, David - I'm Helen. Wanted to say thank you! I've been listening to your How I Write series - it's been so beneficial for my personal writing practice. Started a newsletter 3 weeks ago - and this talk with Lenny is helping me restructure my Substack!
This was such a great listen! I totally loved the honest answers and of course the beautiful practical authentic questions asked to the guest . Great job guys ✅👏💟
Success you get from creating value for others is just a by-product, a happy coincidence :) Lenny's podcast (and other content) is definitely one of top 5 things that have helped me in my learning!
I have been loving this series. David, you ask evocative questions. Your guests always have something that makes me think more deeply and purposely about my own writing and processes. Thanks for a great episode.
TLDR: Delivering high-quality, valuable content, prioritizing storytelling, and setting boundaries are crucial for success in writing and content creation, particularly in growing a successful newsletter. 00:00 📈 Lenny Rachitsky grew his Substack newsletter to 531,000 subscribers by focusing on delivering high-quality content, interviewing industry experts, and staying humble. 13:05 📈 Lenny Rachitsky emphasizes the importance of storytelling, high-quality content, and setting small goals to achieve success in writing and content creation. 25:36 📈 Lenny Rachitsky discusses the challenges and fulfillment of writing a newsletter, including the pressure to consistently produce content and the rewarding feedback from readers, as well as his process for creating and editing posts, the importance of concise introductions, and gaining a large following through Medium and guest posts. 35:32 📝 Lenny Rachitsky prioritizes writing and creative time by setting boundaries, saying no to meetings, and learning from mistakes in content creation. 44:48 📈 Focus on delivering high signal to noise ratio content, prioritize useful answers over poetic writing, promote on LinkedIn for more attention, and research by interviewing and identifying patterns. 54:39 📝 Lenny Rachitsky uses Koda for tracking, Google Docs for guest posts, and Substack for publishing, emphasizing the importance of a copy editor and writing about personal expertise to build a strong subscriber base. 01:11:00 📈 Focusing on niche markets and providing valuable insights are key to building a successful newsletter, with systematic planning and avoiding distractions being crucial for quality content. 01:22:25 💌 Expertise and passion are key to success on Substack and the internet.
The reality is, most people following Lenny are also part of the Marty Cagan clans - none of those people have launched/contributed significantly towards the development/lauch/maturation of successful products.
TLDR: Delivering high-quality, valuable content, prioritizing storytelling, and setting boundaries are crucial for success in writing and content creation, particularly in growing a successful newsletter. 00:00 📈 Lenny Rachitsky grew his Substack newsletter to 531,000 subscribers by focusing on delivering high-quality content, interviewing industry experts, and staying humble. 13:05 📈 Lenny Rachitsky emphasizes the importance of storytelling, high-quality content, and setting small goals to achieve success in writing and content creation. 25:36 📈 Lenny Rachitsky discusses the challenges and fulfillment of writing a newsletter, including the pressure to consistently produce content and the rewarding feedback from readers, as well as his process for creating and editing posts, the importance of concise introductions, and gaining a large following through Medium and guest posts. 35:32 📝 Lenny Rachitsky prioritizes writing and creative time by setting boundaries, saying no to meetings, and learning from mistakes in content creation. 44:48 📈 Focus on delivering high signal to noise ratio content, prioritize useful answers over poetic writing, promote on LinkedIn for more attention, and research by interviewing and identifying patterns. 54:39 📝 Lenny Rachitsky uses Koda for tracking, Google Docs for guest posts, and Substack for publishing, emphasizing the importance of a copy editor and writing about personal expertise to build a strong subscriber base. 01:11:00 📈 Focusing on niche markets and providing valuable insights are key to building a successful newsletter, with systematic planning and avoiding distractions being crucial for quality content. 01:22:25 💌 Expertise and passion are key to success on Substack and the internet.
David, thanks for this incredible interview. Being one of Lenny's 500,000+ subscribers, I deeply respect his work on newsletter and podcast. It's so enjoyable to know the story behind
I just started Substack, I'm excited to start creating content that hopefully people will see and will add value to them. I'm doing honest no BS reviews so people can make better purchase decisions and I'm also helping people startup their businesses from scratch the most streamlined way..
531,000 people read Lenny Rachitsky’s newsletter every week.
He started in 2019 with zero writing experience, so what’s his secret?
I asked him about writing well, growing a newsletter, and building an ultra-profitable business around creative work.
10 key takeaways:
1. What do people ask you about that you don't have a great answer to? Viral essays are hiding inside this question. If people keep asking you the same question and nobody's written the answer, take on the challenge yourself.
2. Don’t let the size of the internet stun you into inaction. Most of the content out there sucks. Lenny: “If you could just do something better than what's out there, you can rise above the noise.”
3. Lenny’s mantra: “Service instead of self-gain.” Great things happen when you just try to be consistently helpful. No growth hack beats providing real value to people.
4. The world suffers from a scarcity of well-formulated questions from inquisitive people. Lenny has worked in tech for over a decade, and he’s still surprised by how open people are to answering questions and revealing “trade secrets.”
5. Long introductions are a rookie mistake. Save your readers time and jump right into the answer.
6. How to edit: While editing other people (and himself), Lenny asks: “What is interesting to me? Where do I get lost?” Notice where your attention spikes and sags. Your own brain is a great proxy for what people will find interesting (and where they’ll doze off.)
7. You should know what you don’t want to do as clearly as what you want to do. Lenny: “I'm actively not trying to build an empire. I'm actively trying not to build a media company.”
8. Lenny’s first essay went bonkers-viral, partially because of the brilliant headline: “What Seven Years at Airbnb Taught Me About Building a Business.” Let's break it down. “Seven years” gives him credibility, “Airbnb” piques interest, and “about building a business” tells people they can expect actionable takeaways.
9. If you want to have an existential breakdown, try to make each sentence an aesthetic masterpiece. Ditch the poetry and focus on clarity instead. Lenny: “Every time I think about how to write beautifully, I just get stuck, and it just slows everything down.”
10. When in doubt, make it useful: If you want to be widely read, try to solve people’s problems. The peskier the problem, and the more useful your solution, the further your writing will spread.
Um, you left out his copy editor. That's a link I'd love!
Followed Lenny. Thanks!
I never thought of treating my writing like a product to manage.
But today I have become a product manager!
Hi, David - I'm Helen. Wanted to say thank you! I've been listening to your How I Write series - it's been so beneficial for my personal writing practice. Started a newsletter 3 weeks ago - and this talk with Lenny is helping me restructure my Substack!
This was such a great listen! I totally loved the honest answers and of course the beautiful practical authentic questions asked to the guest . Great job guys ✅👏💟
my 4th time watching/listening to this one. So good. Nice work guys.
Just joined Substack, interesting times ahead!
Very inspiring, thank you Lenny and David.
That template for your library for posts you are writing was helpful.
Success you get from creating value for others is just a by-product, a happy coincidence :) Lenny's podcast (and other content) is definitely one of top 5 things that have helped me in my learning!
I have been loving this series. David, you ask evocative questions. Your guests always have something that makes me think more deeply and purposely about my own writing and processes. Thanks for a great episode.
Thank you!
Incredible interview David and Lenny! Really authentic!
Such a nice guy
I love this ❤
TLDR: Delivering high-quality, valuable content, prioritizing storytelling, and setting boundaries are crucial for success in writing and content creation, particularly in growing a successful newsletter.
00:00 📈 Lenny Rachitsky grew his Substack newsletter to 531,000 subscribers by focusing on delivering high-quality content, interviewing industry experts, and staying humble.
13:05 📈 Lenny Rachitsky emphasizes the importance of storytelling, high-quality content, and setting small goals to achieve success in writing and content creation.
25:36 📈 Lenny Rachitsky discusses the challenges and fulfillment of writing a newsletter, including the pressure to consistently produce content and the rewarding feedback from readers, as well as his process for creating and editing posts, the importance of concise introductions, and gaining a large following through Medium and guest posts.
35:32 📝 Lenny Rachitsky prioritizes writing and creative time by setting boundaries, saying no to meetings, and learning from mistakes in content creation.
44:48 📈 Focus on delivering high signal to noise ratio content, prioritize useful answers over poetic writing, promote on LinkedIn for more attention, and research by interviewing and identifying patterns.
54:39 📝 Lenny Rachitsky uses Koda for tracking, Google Docs for guest posts, and Substack for publishing, emphasizing the importance of a copy editor and writing about personal expertise to build a strong subscriber base.
01:11:00 📈 Focusing on niche markets and providing valuable insights are key to building a successful newsletter, with systematic planning and avoiding distractions being crucial for quality content.
01:22:25 💌 Expertise and passion are key to success on Substack and the internet.
Great freaking convo David! Slowly becoming my NEXT favorite option to My First Million.❤️💪🏽💪🏽
This series is awesome!
Great content! Both super heroes- how many points of interest do u add in each newsletter?
Does anyone know which author David mentions that has an article that mentions why he doesn't have personal meetings? I'm interested to know🙏🏽
Got you
www.onstartups.com/tabid/3339/bid/60758/Dear-Friend-Sorry-My-heart-says-yes-but-my-schedule-says-no.aspx
13:47
Lenny has George Lucas vibes.
Are we worried about AI and its trajectory to dominate the internet by 90% by 2025? Including algorithms. Or does a newsletter by pass this?
I think the more AI content that hits the internet the more valuable good writers/authentic content are going to become
The reality is, most people following Lenny are also part of the Marty Cagan clans - none of those people have launched/contributed significantly towards the development/lauch/maturation of successful products.
What's wrong with that? Wouldn't that be their motivation to follow him in the first place?
Bitter Bob?
This conversation is making me think a podcast with Dan Koe would be an awesome conversation!
Great interview. There's a lot of audio hiccups when Lenny's talking though... are you using some AI audio editor by chance?
TLDR: Delivering high-quality, valuable content, prioritizing storytelling, and setting boundaries are crucial for success in writing and content creation, particularly in growing a successful newsletter.
00:00 📈 Lenny Rachitsky grew his Substack newsletter to 531,000 subscribers by focusing on delivering high-quality content, interviewing industry experts, and staying humble.
13:05 📈 Lenny Rachitsky emphasizes the importance of storytelling, high-quality content, and setting small goals to achieve success in writing and content creation.
25:36 📈 Lenny Rachitsky discusses the challenges and fulfillment of writing a newsletter, including the pressure to consistently produce content and the rewarding feedback from readers, as well as his process for creating and editing posts, the importance of concise introductions, and gaining a large following through Medium and guest posts.
35:32 📝 Lenny Rachitsky prioritizes writing and creative time by setting boundaries, saying no to meetings, and learning from mistakes in content creation.
44:48 📈 Focus on delivering high signal to noise ratio content, prioritize useful answers over poetic writing, promote on LinkedIn for more attention, and research by interviewing and identifying patterns.
54:39 📝 Lenny Rachitsky uses Koda for tracking, Google Docs for guest posts, and Substack for publishing, emphasizing the importance of a copy editor and writing about personal expertise to build a strong subscriber base.
01:11:00 📈 Focusing on niche markets and providing valuable insights are key to building a successful newsletter, with systematic planning and avoiding distractions being crucial for quality content.
01:22:25 💌 Expertise and passion are key to success on Substack and the internet.
David, thanks for this incredible interview. Being one of Lenny's 500,000+ subscribers, I deeply respect his work on newsletter and podcast. It's so enjoyable to know the story behind
I just started Substack, I'm excited to start creating content that hopefully people will see and will add value to them. I'm doing honest no BS reviews so people can make better purchase decisions and I'm also helping people startup their businesses from scratch the most streamlined way..
Great conversation guys!