⚡️Sense and serendipity.
How idle founder chitchat can be one of the most reliable forms of insight and breakthrough.
Early start-up breakthroughs are the product of more randomness and serendipity than most would expect.
Moments that feel like the results of luck more than deliberate planning. There are many founders who will talk about turning points in their trajectory owning to a chance conversation or a lucky run-in. Little breakthroughs that happened because of “right place, right time” or a “lucky break”.
Well, I’m a believer of a unique brand of lucky - start-up serendipity. The kind that unstuck founders and change outcomes. It’s a kind that has plenty of chance involved, but it’s also a function of playing the probabilities. Of putting yourself firmly in the path of high probability outcomes.
🤓 Don’t stare.
So much of building is staring straight on at the problem that you need moments of idle productivity. Those pockets of time when you’re still noodling the problem at hand, but in a background way.
It’s a cousin of rest (which is important for other reasons and can lead to breakthroughs of its own), but idle productivity happens in moments when you’re not trying so hard. Like a ball of knotted up twine that you need to first loosen by feel, while focusing on something else entirely.
👯♀️ Find a founder friend or two. Or two hundred.
It usually doesn’t happen with the people on your team because then you get sucked into the details and before you know it, you’re staring straight on at the problem again.
Instead, I’ve seen these moments best happen at social gatherings of other founders. When you’re chitchatting about the current thing you’re working on or sharing a particularly hairy challenge.
The magical thing about fellow founders is that they’re usually 1. eager to want to think about someone else’s problems for a change, 2. intellectually curious enough to be able to quickly understand what you’re building and 3. able to ask the hard or candid questions that can lead to both insight and detailed discussions.
And because this other founder likely doesn’t have exact domain experience, they’ll offer up insights by analogy. Suggestions of things to think about or things they’ve seen or done. Maybe they have a friend that they can connect you to. Perhaps they throw something out there and you pick that idea thread up and build on it. Now, a social conversation, that feels like a break, is actually enabling you to push your thinking further.
This, is the magic of serendipity in the world of startups. It’s less pure luck and more high probability fortuity. Putting yourself in the path of insight and inspiration.
The thing is: it’s still random and you cannot bank on it.
But, it’s why Tuesday night dinners during the 12 weeks of YC batches were so important. Most people fixate on the (almost assuredly amazing) speaker of the evening but in this room there are on average ~200 of some of the smartest, most driven founders in the world. Just catching up over the hour or two of dinner meant I was certain to go home with at least a couple gems to work through the next day (btw, I don’t mean the fancy networking events put on by VCs or panels and conferences - they can suffice but usually also mean more wasted time is involved as well. There was nothing fancy about dinners at YC. It just so happened to be the weekly ritual of gathering and rest).
🖥 Video killed the idle chatter.
This is also one of the reasons I’ve personally found the past 2 years so hard to be an early stage founder. Many of us found ways to at least keep some semblance of in-person building with our teams.
But social events with fellow founders were certainly not happening. Even YC has gone virtual over the past 3-4 batches.
It took sitting back down at 335 Pioneer, in view of the famous orange walls, doing my first in-person office hours in 2+ years with pg to realize what our start-ups have been missing out on all these months.
As we chatted idly about the conversations those orange walls have borne witness to over the past 15 years, pg mused whether it was possible via zoom. I shook my head emphatically no.
Zoom is for matters of agenda and pointed conversion. Idle chitchat even at the beginning feels forced and painful. Even my founder groups done over zoom have a “my turn, now your turn” quality to it.
It’s not all bad.
But it’s not great for this idle, social, serendipitous magic.
And sometimes you have to lose something to understand exactly why and how you valued it.
It took losing this over the past couple years to make me want to make sure I don’t go without it for so long ever again.
Knowing I won’t have those 12 weeks of YC again and weekly groups of 200 founders to just bump into, I now think about curating it more selectively. A standing monthly happy hour, a dinner with founders while I’m travelling. Consistent office hours in person when and how I can.
Whatever it is, I believe deeply in the magic and power of start-up serendipity. It’s just as strategic and important to me as a weekly sprint plan.
Sound like hyperbole? Not at all.
If start-ups are about insight arbitrage, then you’re only as good as your insights. Being pushed by your peers to see things differently or through a new lens is as good a way as I know to keep your insights sharp while still keeping heads down and building.
So plan for your lucky breakthroughs. Set yourself in the path of serendipity.
Let lightning strike.