EP 39 | How Lenny Rachitsky became one of Substack's top writers with 350,000+ subscribers

Listen now on:



“There’s a lot of opportunity just to do primary research on behalf of people and they’ll pay for that.”

On this week’s episode of The Aarthi and Sriram Show, we interviewed Lenny Rachitsky.

Lenny needs no introduction here – Lenny’s newsletter with 350,000+ subscribers and his leading Lenny’s podcast is listened to by a large section of Silicon Valley. Lenny is also an active investor, previous product lead at Airbnb and founded Localmind (acquired by Airbnb). And he’s a dear friend.

In this episode, we cover: his journey from Airbnb to Lenny’s newsletter, dealing with imposter syndrome / fear of getting started, how to build an audience, platform-specific growth hacks, content monetization, content creation / podcasting 101, and more!

In this episode, we cover:

  • Airbnb to Lenny’s newsletter

  • The endless validation treadmill of being a creator

  • Dealing with imposter syndrome

  • How to be a creator 101

  • How to win over the fear of getting started

  • Lenny’s target audience

  • Building Lenny’s podcast

  • Building a podcast: what works and doesn’t work

  • What makes a good and bad show guest?

  • Podcast prep 101

  • Platform-specific growth hacks

  • How to monetize your content 

  • What’s Lenny’s exit plan?

  • Lenny’s favorite creators

  • What’s your legacy?

Notable Quotes: 

“I don’t know how I get off this treadmill. I have a subscription newsletter where people are buying an annual plan every day. I have to keep writing at least for another year. Then to stop it, I’d have to give it all up.”

“I find that there’s a strong correlation between the time I put into something and how well it does.”

“You don’t need to basically be the smartest person if you just have a lot of time.”

“A lot of people have great stuff and they write once a year. A lot of people have okay stuff they write constantly, but it gets better. It all comes down to consistency and quality.”

“Don’t overthink how much people will remember. They’re just going to immediately forget you did anything.”

“ If you’re trying to figure out what to write about, what I’d start is what just wants to get out of your head that you don’t want to forget. Pay attention to that and then pay attention to what people often ask you for advice about and just write it. Write it in a place and then you could send people that thing.”

“There’s a lot of opportunity just to do primary research on behalf of people and they’ll pay for that.”

“The act of aggregating intelligence and knowledge is super useful and I think it’s a great way to get over imposter syndrome.” – Sriram Krishnan

“I was doing Harry Steppings.  At the end of it, we start recording and he’s like, “Well, you should be doing a podcast, idiot. Why aren’t you doing a podcast?” That basically got me over the hump of like, “All right. If he thinks I need to do a podcast, and this conversation went well, all right, I’m going to try it.” It’s that actual conversation that led to that.”

“Your stuff’s never going to reach your audience unless you go into the medium that they’re excited about.”


Lenny Rachitsky, Substack

Substack’s cross promotion recommendation feature

The Twenty Minute VC (20VC), Harry Stebbings

John Stewart, host of The Daily Show 

Howard Stern, Howard Stern Show

Larry King, The Larry King Show

Noah Smith, Noahpinion

Tyler Cowen, conversations with Tyler 

Emily Oster, American economist and author (data-driven parenting advice)

Where to find Us:

• Aarthi and Sriram’s Good Time Show: Youtube, Substack, Twitter

• Aarthi Ramamurthy: Twitter, Instagram

• Sriram Krishnan: Twitter, Instagram, Blog