Why Hosting Lenny’s Meetups is the Best Decision I Ever Made
The Real Value of Connection: My Experience Hosting Lenny's Meetups
For the past year, I've been hosting Lenny's Newsletter meetups in Singapore every 1-2 months. Lenny's Newsletter is a weekly advice column about building product, driving growth, and accelerating your product management career. A paid subscription to the newsletter gives you access to a private Slack community, which I found super useful.
The why
My main motivation for hosting the meetups was to recreate the sense of community I had when I was working in Toronto. Back then, I was part of this incubator called OneEleven, where there were always these lunch & learns, talks, and meetups happening for all of us from member companies.
I loved how it felt—connecting with people from different startups, sharing stories—learning from each other's successes and challenges. That feeling of being part of a thriving, learning community—that's what I wanted to recreate with these meetups in Singapore.
It's an interesting experience hosting these meetups in Singapore. Our meetups started with 15-20 people and have grown to around 30-40 attendees. It's never dull when we gather over food and drinks and dive into all things product.
The diversity of our attendees is what makes these meetups truly special—we have locals, expats, people from nimble startups, and veterans from mature companies. Everyone brings their unique insights to the table, adding a richness to our discussions that I've come to really cherish.
My takeaways
An impactful moment for me was learning that I'm not alone in my product journey. We all come from diverse backgrounds and have different responsibilities, yet we face the same challenges. Whether it's dealing with demanding stakeholders, wearing multiple hats, or the constant need for effective communication, we're all in the same boat.
These shared experiences have provided comfort and fostered a strong sense of camaraderie among us. It's truly heartening to see familiar faces return, as these strengthen the bonds within the community. As we move forward, my hope is that these connections continue to grow, adding depth and richness to our discussions and shared experiences.
Hosting these meetups has led me to reflect on the type of product work I wanted to do. I've noticed that many companies here see product management differently than in places like Silicon Valley. Product managers here seem to be more like project managers—keeping things moving instead of shaping the product's direction.
I prefer to have a say in the Why and the How, instead of only executing the How. This realisation has guided me to be more deliberate about my career choices, prompting me to seek roles that offer a greater influence over the product's trajectory, rather than just maintaining the status quo.
On top of that, I found myself drawn to the idea of getting hands-on with the consumer side of things. Being a platform PM in the past was great, but the problems started feeling a bit repetitive after a while.
What’s next?
As I've navigated through this journey, I've been open to feedback and suggestions to improve our meetups. Some folks have proposed more structured meetups featuring talks and sharing. While I appreciate the value such structure could bring, I am also conscious of the logistical challenges, like finding a larger venue, arranging for AV equipment, and finding speakers willing to share their experiences.
That said, one suggestion that caught my interest is a virtual meetup with product managers from another country. The prospect of understanding how product management operates across diverse cultures is certainly an appealing one. I'm already considering the feasibility of such an event, stay tuned!
To anyone from the Lenny's Newsletter community who's considering hosting your own meetup—take the leap. It's simpler than you might think. All you need is a time and place.
The rest—the lively discussions, the shared laughs, the connections—will naturally fall into place. There's a unique kind of warmth and collective understanding that emerges from these meetups, truly a feeling unlike any other.
Do you still organize meetups?