It is incredibly rare to have your startup become a verb. Google and Uber immediately come to mind. But what about when a group of strangers or friends with shared interests decide they want to get together? They, Meetup.

Scott Heifferman didn’t set out with becoming a verb in mind but he certainly started Meetup with the intent of building something big and impactful. And on those dimensions he delivered in spades. Along the way he sold 30% of his company for $1M to Tim Draper’s DFJ (funny story around the 36 min mark), raised from other great investors (Brad Burnham from USV makes a cameo in the video), met face to face with Mark Zuckerberg who also decided that getting groups of people to meetup would be important for Facebook too, going so far as to run their very first Super Bowl ad promoting their meetup competitor product. There are so many great stories and anecdotes in this one.

In our effort to mine Web 2.0 ideas and playbooks for applicable lessons for this current wave to startups, this conversation delivers in spades. A few take aways:

— The Origins of Meetup and Community Building: Heiferman reflects on how 9/11 and experiences like Burning Man inspired Meetup’s mission to foster real-world connections. He emphasized the importance of creating tools that empower people to form communities and build belonging offline, using the internet as a catalyst.

— Early NYC Tech Scene vs. Silicon Valley: Heiferman shares stories of the scrappy, experimental nature of the 1990s NYC tech ecosystem, contrasting it with Silicon Valley’s more established infrastructure. He recalls starting iTraffic with maxed-out credit cards and seeing startups like Razorfish and DoubleClick shape the local scene.

— Facebook’s Competitive Threat: Heiferman recounts how Facebook’s groups feature directly competed with Meetup, even running Super Bowl ads mimicking its concept. This competition influenced his decision to sell Meetup to WeWork, as Facebook’s scale and resources were hard to match.

— Critique of Modern Marketplaces: Heiferman critiques platforms like Uber and DoorDash for extracting excessive margins from workers and businesses. He advocates for a fairer market economy where technology empowers individuals rather than exploiting them.

— Future Vision and Lessons Learned: Looking ahead, Heiferman expresses interest in building impactful projects outside traditional VC structures. He emphasizes the need to focus on creating products that energize people, deliver value, and prioritize meaningful societal impact over maximizing profits.

One thing that especially stood out to me in this conversation was a reminder of how “people” were so core to Web 2.0 ideals. Whether it was getting people to connect online or off, fostering real and personal connection was such an important driver for innovation at that time. When today’s headlines are so filled with stories that seem to pit people against algorithms, Scott’s sentiment is a refreshing reminder that technology at it’s best is a tool for enhancing our lives, not eradicating them.

On that theme, a comment Scott made has been rattling in my head ever since. At around the 40 min mark he says something along the lines of “AB testing is the price you pay for not having a pulse on people”. In this conversation he talk a lot about energy, following the energy of individuals and his own energy and interests. He seems energized to build again and we talk a bit about what’s next for him and how his time working in an Amazon warehouse informed his thinking around what problems he wants to tackle. We can’t wait to see where he goes with all that energy.

This was a ton of fun to connect with Scott and Brad to revisit the Meetup story. We hope you enjoy listening as much as we enjoyed recording it.

Macrocast: Norm-Busting