Five Lessons from “Brunches with Strangers”

One of the biggest aspects I lost when I graduated from college was the social life. All my social interactions these days range from driving distance to the need to cross the Pacific or Atlantic, compared to a simpler time when my friends were within walking distance. So, earlier this year, I started a little passion project: Brunch with Strangers (BWS).

BWS began as an effort for me to:

• Help overcome my deep fear of public speaking;
• Have an excuse to bring fascinating souls to the same table;
• And, help make the San Francisco Bay Area feel just a little smaller and just a little more human.

It’s a Saturday brunch I hold every fortnight between six to eight thrill-seekers, hustlers, crafts(wo)men, entrepreneurs, engineers, and curiously-curious individuals. They are working on interesting projects, have captivating stories, and/or possess an infectious drive for their passion. The key element is that I have to be reasonably confident that they don’t know more than one other person who will be at BWS before the meal, which is, admittedly, harder than I initially thought for folks in the Bay Area. After 20 brunches, with a little over 100 guests and circling back in with 90% of them in the post-mortem, here are the five main takeaways from these enthralling conversations, ordered from the most to least intuitive for me:

1. Structured conversations work better than unstructured conversations.
2. Cap it.
3. The culinary experience doesn’t matter.
4. Embrace “awkward” silences.
5. Don’t introduce the guests before the day of the brunch.

Structured conversations work better than unstructured conversations.

But what does “better” mean? I measure “better” by the guests’ answer, a month after the brunch, to the question:

Were you able to catch up with another BWS guest (whom you did not know beforehand) in person?

In the context of startups, that question is how I measure my product-market fit, which I share more context to in a separate post. Guests of a structured BWS are 30% more likely to catch up in person within a month of the brunch than guests who join me in an unstructured BWS. Between structured and unstructured brunches, a structured brunch is when I have at least one activity or topic planned for during the brunch, whereas unstructured brunch, my “control variable”, happens when the guests get to decide how and where the conversation goes, and discussion is more free-flowing.

Over the score of brunches I’ve hosted, the two most well-received activities were 1) a game I call Hidden Questions, and 2) where each guest brings two asks.

Hidden Questions, inspired by Jimmy Fallon’s Pour It Out, is a game where each person has to answer truthfully two to three questions, written by the previous group of people who played the game, but is not required to reveal what the question is. The deck of questions the previous group writes, which even I’m not privy to look through, can cover any topic and ask any range of questions – from favorite books to deepest fears to NSFW ones. Some of my personal favorite are “When was the last time you uncontrollably cried?” and “When was the last time you said ‘I love you’?”. If the person answering the question does not reveal the question itself, he/she has to eat a Beanboozled bean or take a spoonful of one of the spicier hot sauces found on the show Hot Ones. The catch is before the person answering the question decides to reveal question or not, the other guests can ask clarifying questions and bet additional beans or spoonfuls of hot sauce for the person to eat if he/she doesn’t reveal. So, if he/she does, then the other guests eat what they bet. It’s a fascinating game that creates a safe space where people have the excuse to be vulnerable, as well as revealing each person’s level of risk aversion.

On the flip side, to help guests mentally prepare and pick the dilemma of the highest priority, I ask guests at least 48 hours, up to a week, in advance to bring two asks to the brunch:

1. One that they’d feel comfortable sharing with most of their friends;
2. And, one that’s either deeply troubling them and require them to be vulnerable, or one that shows a very different side of them that most people they know might not recognize.

The asks themselves are structured by answering two questions: ‘What are you currently working on?’ and ‘What do you need help with?’, which can range from work to personal life to new projects and hobbies to relationships. When the time comes to share the guests’ asks, usually about 20 minutes in, I ask them to share the one they’re more comfortable in sharing. Based on what they share, I can gauge how comfortable they are with the other guests, as well as indicate how well I’m doing my job.

The asks also incentivize mentorship from folks who have had wildly different experiences in different industries at different ages. For example, an autonomous driving product manager provided advice on building systems to streamline communication to a remote workforce to a newly-minted landlord and property manager by predicting actions and that may need to be taken by the landlord’s employees and working to preempt them. In another brunch, an indie film producer taught us all how to hustle, be scrappy, and run effective crowdfunding campaigns by going back to the roots of meeting people face-to-face rather than over the Interwebs. And more recently, a digital nomad shared his $0.02 on how to build a network and community in a new geography and culture from scratch by being willing to do manual labor and noticing when people needed help, to build trust.

Cap it.

One of the best conversationalists I know, Bobby, once told me:

“A great conversation is like flirting with a girl you really like.”

Share enough to make him/her interested, but close the conversation sooner than you’d like to suggest a sense of scarcity, as well as a reason to go on a second date. If you reveal everything too soon, your audience will most likely lose interest as soon as they have no more questions, like how many of my friends have spoiled the whole plot of Game of Thrones (and now it’s The Mandalorian) before I even began Episode 1 of Season 1.

The same seems to be true for the BWS conversations. I found a moderately strong negative correlation between the length of the meal and the number of in-person catch-ups within a month of the meal, after the first one-and-a-half hours (and a moderately weak negative correlation of meal length and number of in-person catch-ups, if the meal length lasted between an hour and an hour and a half).

Both to be respectful to others’ schedules and to motivate them to catch up after, I cap the brunches to 1.5 hours. To be fair, I am still testing out the optimal length of time, since I don’t have a big enough sample size to decide from.

The culinary experience doesn’t matter.

I initially thought that more interesting meals and/or great eats, which at times, fell on the more expensive side at two to three dollar signs, would give folks, in the worst possible scenario, the culinary experience to talk about when they have no other topic or background of each other. It turns out the culinary experience doesn’t have a strong correlation to the reduction of the number of awkward silences, which I assumed would serve as a leading indicator for how likely guests were to catch up in-person after.

In fact, even when guests had the disposable income to afford the meal, when a meal is expected to exceed $50 per person, it is more likely that the culinary experience detracts from how vulnerable a person can be.

The culinary experience will always come second to the guests and the conversation they bring.

Embrace “awkward” silences.

Speaking of awkward silences, my initial goal was to reduce the number of “awkward” silences in a conversation. Maybe it was my anxiety speaking, but I realized two things:

• What’s awkward to me may not be awkward to another;
• And, silences are diamonds yet to form (under pressure).

Some people need time to digest everything they have heard up to that point in the conversation. Some people need a break to eat the food they ordered. Some people need time to formulate the next question they want to ask. But for me, silence offers an opportunity to allow guests to dig deeper.

In relation to silence, fours years ago, one of my dearest mentor figures, Robin, shared two rather insightful tips with me:

1. “Listening is the most important of conversation, and silence, too is one of the sounds a conversation emits.”
2. “People like to talk about themselves. Give them the opportunity to.”

Silence is that opportunity for people to share more about their life stories. And with the right prompt, it can become a safe space for them to be more vulnerable. And there are two ways I help them continue, with the addendum that I, myself, am vulnerable with them first, earlier in the brunch:

1. Lean in. Ideally, with an open inquisitive look. I don’t have to say anything, but it will eventually prompt them to continue. It might feel a bit awkward at first.
2. Ask them to rewind to a point they brought up that I find fascinating, curious, or needs more explanation.

Late night talk show hosts, like Conan O’Brien and Stephen Colbert, and podcast hosts, like Tim Ferriss and Cal Fussman, are really acute at catching these moments and serve as great case studies.

Don’t introduce the guests before the day of the brunch.

At first glance, this seems a bit counter-intuitive. Of course, I want the guests of each BWS to be excited for people who are going to be present at the brunch. I would absolutely love to show off the wicked roster of brilliant individuals each time. What ended up happening is when I did initially release the guest list, many guests did some diligence of the other attendees, and a few came to the brunch with predisposed assumptions of who the others were.

Though most tend to be relatively accurate assumptions, the brunch lost its air of mystery and curiosity which affected the guests in two noticeable ways.

1. The guests who did their research were less curious on what they thought they knew about another guest and rarely ended up discovering the thought and emotional complexity behind social media posts, titles, and press releases.
2. Over half of the guests who had been researched felt they couldn’t be as vulnerable as they would have liked, in efforts to “live up” to the expectations of the guests who did their research.

So, going against the grain, I decided, after the first five brunches, to no longer release the guest list prior to the meal.

In closing

With many more to follow, the lessons learned now is only the tip of the iceberg, as I continue my adventure learning from the craziest, the most curious, the most creative, and the most inspiring people out there.

À l’année prochaine!