On Thursday, I had the honor of speaking at The Lenny and Friends Summit in San Francisco, where some of the best and most important people in product, AI, and tech assembled to listen and learn.
About 1,000 people attended the conference, but many more wanted to attend.
It was a big deal.
The “Lenny” of Lenny and Friends is Lenny Rachitsky.
Lenny was a software engineer and startup founder who spent seven years working at Airbnb, eventually leading product work involving supply growth, conversion, trip quality, and community.
After leaving Airbnb in 2019, he began writing about what he’d learned. That evolved into Lenny’s Newsletter, one of the most prominent product and business newsletters on the planet, followed by Lenny’s Podcast, where he interviews leading founders, executives, product leaders, and thinkers.
It was that newsletter, and later that podcast, that had made him known throughout the world as one of tech’s most important and influential voices.
The Lenny and Friends Summit grew out of his writing and his podcast.
Back in 2021, I appeared on Lenny’s podcast. At the time, I had no idea who Lenny was. I thought that some random guy named Lenny had oddly named his podcast after himself and had emailed to invite me on his show.
I said yes, and the result was a conversation that I enjoyed quite a bit but didn’t think would go very far.
A couple of weeks later, when the podcast was published, half a dozen of my clients called or emailed me, all within an hour of each other, essentially saying:
“Oh, my God! You’re on the Lenny Podcast! Why didn’t you tell me?”
My response:
“Who’s Lenny? What podcast?”
I’m a very dumb man.
That single episode has brought in more business for me than I ever could’ve imagined.
I followed up the episode by guest-writing one of Lenny’s newsletters and, on Thursday, speaking at his summit.
Next month, I’ll be appearing on his podcast for a second time.
I feel blessed to be a tiny part of his impressive world.
What I love about Lenny and what he has built is this:
Lenny has built himself a small empire, populated by devoted fans, skilled professionals working for him, and some of the best minds in tech. He’s a force of nature in the tech world, and his words carry real meaning.
But it all began with writing.
He simply started writing about what he knew, in a way that was insightful, engaging, impactful, and best of all, in his voice.
His podcast followed a couple of years later, but that, too, amounted to him sharing his insight with the world through the people whose work he thought was worthy of elevating.
Through it all, Lenny has remained a deeply humble, almost unassuming man who is relentlessly focused on one core mission:
Share good ideas in his area of expertise with the world, and find others who can do the same.
Lenny did not think, back in 2019, that he would be hosting a summit that gathered people from all over the world to listen to world-class speakers (and me) talk about tech, product, AI, and more. He could’ve never envisioned the caliber of companies that partner with him for his summit as sponsors, vendors, and designers. He never could’ve imagined the scores of brilliant people wrapping around the block, waiting to register, collect their badges, and begin the fun.
He started out doing something he loved, without any intention of someday becoming a voice that reaches over one million people every week.
I love this.
When people ask me for my secret sauce because they want to follow in my footsteps, either as a storyteller, keynote speaker, consultant, or executive coach, I always say:
“Start by leaving your full-time job around 4:00 in the afternoon and driving about three hours, often alone, to New York City, with the hopes of maybe telling a five-minute story in a bookstore or bar for free before heading back home. Crash into your bed sometime around 1:00 AM, and then rise again around 6:00 AM for another workday.
Do this three or four times per month for about four years, with the singular goal of becoming the best storyteller possible. Have no goal of turning storytelling into a career. Simply seek excellence. Try to be the best. Fight like hell to find ways to improve.
No plan for profit. No visible path to a career. Simply do something well for the sake of doing it well.
Then, maybe if you’re lucky, someone might come along and say, “Hey, you tell a great story. Maybe you could help me tell mine.”
The one client eventually became Google, Amazon, Microsoft, Johnson & Johnson, Pfizer, and the FBI. It became Yale, MIT, Harvard, and Princeton. It’s become the Gates Foundation and the World Bank.
Did I expect any of this to happen to me?
Like Lenny, no. Of course not.
I thought I’d always be an elementary school teacher who writes novels and tells stories on stages in New York, Boston, and later in the Hartford area when Elysha and I launched our own show.
I didn’t begin telling stories to change my career and my life. Like Lenny, I started telling stories because I loved telling stories and wanted to become great at it.
Remarkably, people began to recognize my excellence and offered to pay me for it.
There are no shortcuts to excellence. You need to put in the time, the sacrifice, and the effort. If you’re not great at what you do, it’s unlikely that anyone will be interested in what you have to offer.
Lenny offered outstanding insight and wisdom. He made his thoughts and ideas invaluable to the tech industry. He used his voice through a newsletter and then a podcast to build a following that eventually became his career.
But it starts with the desire to do something well. Better than most. Perhaps the best in the world.
If you’re willing to do that, making all the sacrifices required along the way, you have a chance.
