You might know him from his extremely successful newsletter, where he dishes out product management advice to 600,000+ subscribers. Or you might be an avid listener of his show, where he interviews world-class product leaders and growth experts. Whatever the case, Lenny Rachitsky has become a household name in the world of startups and product growth.
But how did Lenny transition from the written word, blessing inboxes all around the world, to the dynamic conversations of his show? And what can creators learn from his journey to enhance their own show and optimize their growth journey?
We sat down with him to find out. Keep reading to get Lenny’s unique perspective as a creator who has mastered the art of engaging audiences across different media.
Lenny Rachitsky's journey into becoming a creatorintriguing. Already a celebrated figure for his highly acclaimed "Lenny's Newsletter," he carved out a niche that allowed him to find success in his post-tech-job life. “The last thing I wanted was more work," Lenny admits, reflecting on his initial reluctance to take on another project.
However, the idea of starting a show was a persistent whisper that grew louder over time. "It eventually became too hard to resist. Many people much prefer listening to a podcast over reading a long newsletter," Lenny explains. “Also, I felt that I could get more knowledge into the world by interviewing diverse experts, vs. me sharing just my advice.”
His decision was sealed when, after recording an episode for “The Twenty Minute VC (20VC)”, host Harry Stebbings remarked, "Lenny, why don't you have your own podcast?" The unexpected feedback pushed Lenny over the edge, and so, in late 2022, “Lenny’s Podcast” was born.
Lenny’s podcasting philosophy boils down to a simple principle: quality. He’s a product expert through and through, and his approach to creating and growing his show reflects his years of experience in the field.
"Something I've learned over the course of my career is the power of quality, and of keeping a high bar," he states, emphasizing the importance of excellence in a landscape brimming with podcasts. Lenny acknowledges this abundance, but points out a critical gap: "There are a lot of podcasts in the world, but not that many great podcasts. There’s always room for something better. And if you make something great, people will share it, and that's how these things truly grow."
For Lenny, quality hinges on three factors:
Click here for our top advice on writing winning episode descriptions and check out our best tips on creating captivating cover art.
We can’t talk about Lenny and his show without addressing the impact of his newsletter on the latter. Lenny himself acknowledges he had “a huge, unfair advantage,” as the newsletter audience was already established, engaged, and receptive to his content.
But even if you don’t have a channel with hundreds of thousands of followers, there’s something to be learned here—the symbiotic relationship between newsletters and shows. You might not have a ton of loyal subscribers to begin with, but that foundation can serve as fertile ground for podcast growth.
"A big learning of mine is that it's a lot easier to grow a newsletter or email list than it is a podcast," Lenny reveals. It’s easy to see why:
However, Lenny also cautions against waiting too long to start a show in the pursuit of building a newsletter audience. "I don't think it makes sense to spend years first building a newsletter before launching a podcast," he states. "But, I would definitely invest in building an email list regardless, because it's possibly the most powerful owned channel out there."
Ready to start your own podcast newsletter? We have a step-by-step guide to help you hit the ground running.
Lenny’s newsletter wasn’t the only lever he pulled to grow his show. He flexed his long-honed skills to test different strategies and find out what really works.
Lenny is notorious for interviewing very knowledgeable people on his show. Just like launching a product with high-demand features, having podcast guests “who people are eager to hear from” attracts audiences by offering exclusive insights from industry leaders.
We can’t all have big names on speed dial, but that doesn’t mean you have to give up on the idea altogether. A good guest is someone who will add value to your show by bringing unique insights, engaging stories, or expert knowledge that resonates with your audience—regardless of their fame:
Find out more about how to land coveted podcast guests from the hosts of “Leave Looking Up”.
Beyond guest selection, Lenny emphasizes the power of social media in amplifying podcast content and keeping the conversation going across several channels.
Lenny finds that distributing the most compelling parts of an episode across Twitter, LinkedIn, Instagram, and TikTok helps creators capture the attention of potential fans. "Instead of teasing gold, just give all the gold away. Once people see the gold you have, they'll go seek you out. Do this with fun clips, key quotes, or simply writing out the most interesting or surprising takeaway from the episode.”
He often shares short (less than a minute long), snappy, and engaging clips from his guests on LinkedIn and exciting episode trailers on Twitter. This is the type of content that immediately grabs scrollers’ attention, provides value, and gets them clicking toward the full episode.
Check out our channel-specific tips to squeeze the most value from every social media platform and grow your show.
Lenny's approach to launching his podcast was nothing short of a product launch event. "I launched in a big way, pre-announcing my first 20 fancy guests, and making it clear this was going to be a thing," he recalls. Lenny’s strategy not only piqued interest but also set expectations for the quality and caliber of the content, encouraging early listener investment.
This approach doesn’t have to be limited to new shows. You can just as easily make a big deal out of your upcoming seasons or episodes:
Reflecting on his podcasting journey, Lenny acknowledges the pivotal role of video content in expanding his podcast's reach. "I've learned that some people want to read, some people want to listen, and some people really want to watch. The sooner you can get to all three types of media, the better,” he says.
And he’s right—video podcasts give your show a whole new dimension. Audiences can be privy to every facial expression and be fully immersed in the experience, so they feel even closer and more connected to you and your show. Plus, given how visually driven social media is, a video podcast significantly enhances your ability to engage with audiences across platforms.
It’s okay to take it easy and start small, though. “Don't let this overwhelm you,” says Lenny. “You can add these types of media later. I added video about 6 months in.”
Get started with video podcasts on Spotify. Our platform allows users to seamlessly switch between foreground and background watching/listening, so you can please every type of podcast consumer.
It’s easy to get lost in the maze of strategies when attempting to grow your show. But if there’s one thing creators shouldn’t lose sight of, it’s authenticity. "I started off imitating some other podcast hosts that I respected, and it took me a few episodes to realize that I needed to be myself. And that made everything better," Lenny reflects.
It’s your unique voice and perspective that truly set your show apart. Authenticity is at the heart of connection, and in the end, it's the relationships you build with your listeners that will sustain and grow your show. So, take a cue from Lenny's playbook: be inspired by others, but always, always be yourself.
photo credit for images of Lenny Rachitsky: James Widegren
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