SaaStr Annual, A New Baby, And What To Do At a Conference When You’re Alone

My wife and I were expecting our third baby at the end of January 2017. On our second daughter’s birthday,  actually. Turns out, the largest SaaS conference in the country—SaaStr Annual—was happening just a few days after the baby’s due date

“Book it,” my wife urged. “I’ll be fine. The baby will be 10 days old by then and my mom will be here.” Our other two kids came early, so we figured this one would too. Ten days was our best guess. So, I bought the ticket, booked the flights, and found a hotel nearby.

A week before the due date, my wife had a checkup. No signs of labor.

Three days out, nothing.

The day before, still nothing.

“WTF?” we wondered aloud to each other.

“I’ll just cancel,” I told her. I can’t miss the birth of our baby for some conference.” (Though, it did cross my mind the baby probably wouldn’t notice).

So, a few days later, there we were, at the 40 week checkup, flights and hotel still booked for San Francisco, and no signs of labor. “Not even close,” the doctor told us.

My wife and I looked at each other. I looked at the doctor, saying, “I’m leaving for three days on Tuesday morning (this was Friday). Can’t we induce or something?” *Note: my wife told me to change this line because it sounds like we had the baby so I could go to SaaStr. We agreed to disagree on this point.

“Let me call over and see if they have any room. They’re usually booked by now,” the doctor told us. She picked up the phone and called labor and delivery.

Long story short, we filled the last spot at the hospital, they induced my wife at midnight, and we had a gorgeous baby girl by 5:30am on Saturday. Three days later, I boarded the plane, leaving my wife with two kids and a newborn, and headed to my first SaaStr Annual.

Sleep deprived, anxious, overwhelmed, and alone, I found myself leaning against a wall most of the time, sending text messages to my wife to see if she and the baby were okay. I interacted with strangers, wandered around a bit, and attended the sessions, but honestly, my heart wasn’t in the whole thing.

However, all was not lost. I managed to make some good connections, learn a lot, and have some fun at the after parties.

This year—in just a few weeks, actually—I’ll be in San Francisco for my second go ‘round at SaaStr Annual. This time, though, I’m focused, I’m excited, and most of all, I’m ready to see how much swag I can come home with (kidding, of course. How many software t-shirts can one guy own?)

Part of that plan involves having as many conversations with the right people as possible. And if, like me, you’re uncomfortable walking up to total strangers to strike up a conversation out of thin air—hopefully, without seeming awkward or weird—I’ve come up with a few tricks to make things a little easier.  

1. The Empty Table Technique

We’ve all done it: you grab a beer, pull out your phones to act like you’re doing something really important, and secretly scan the room for someone else to latch on to. And, oh boy, once you make eye contact, it’s all over.

Don’t get me wrong, it takes a lot of guts to walk up to someone and assume they’ll talk to you. But you don’t have to do that. Not in that way, anyway.  

Instead, grab your snack or drink and find an empty table. The tall, pub-style ones work best. Then, just cooly stand there and let people come to you. Don’t pull out your phone. Don’t look around desperately. Just stand there and eat. Or drink. Or spend some time with your thoughts. But, whatever you do, do it confidently. With an air of aloofness. Because standing against a wall makes you look like a weirdo (take it from a seasoned wall stander). An open table, though, is inviting.

Others will join you eventually. They need somewhere to put their food and drinks too. And as long as you’re not staring at your phone, you’ll find conversations happen much more naturally this way. No aggressive awkwardness needed.

2. The Offer They Can’t Refuse Technique

I stumbled onto this technique by accident. See, I chew a lot of gum, which means I always have a pack with me. It felt rude to constantly pull out a new stick without offering one to the people next to me, so I started offering. And, boom! A new subtle icebreaker was born.

It goes something like this: walk into the room a few minutes before the presentation starts, choose a seat somewhere in the middle (yes, you’ll need to squeeze past some people), and sit. Maybe you say a casual ‘hi,’ maybe you don’t.

Then, just before the speaker begins, reach into your bag for a notepad, to put your phone away, or anything else that looks like you’re preparing to be really engaged in 4th growth hack session of the day. While you’re getting things situation, happen to remember you have gum. Pull it out, look at the person next to you, and ask, “Gum?”

Whether they take it or not isn’t really the point, because now you’re talking. And if they do? Well, you’ve just pulled a classic psychological move called “reciprocity.” It’s a proven fact people are more likely to give you something when they’ve been given something first. Which means, they’re more likely to talk with you. Or exchange business cards. Or high-five. Whatever you’re after, is my point.

3. The Off-Peak Coffee Table Technique

Nobody wants to be the person nodding off during the post-lunch presentation. So, instead of embarrassing yourself with the head-nod wakeup, skip the post-lunch presentation all together.

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Inevitably, there are others skipping sessions too. And they’re probably drinking coffee. That’s the thing about 10,000 people at a conference: someone is always drinking coffee.

Use this fact to your advantage. Again, don’t just walk up to a stranger and try to talk. Strike up a conversation while you’re pouring a cup of joe. Or while you’re stirring in the sugar (better yet, ask them to pass the sugar).

Striking up a conversation over coffee is great because the stakes are low, there are fewer people around, and you immediately have something to talk about (i.e. “Can you believe how hot it is in those rooms!?”). Plus, you’ll be able to actually hear each other and there’s no rush to get to the next thing. Everyone else is already there while the two of you are out here. Having a pleasant conversation.

Look, here’s the deal: going to a conference by yourself is tough, even for the most outgoing of us.

But it doesn’t have to be. Put one of these strategies to good use and things will feel better. And because everyone feels better, the results will be better. But make sure your intentions are pure. These types of things are about connecting, not closing. If your only goal is to get a business card or make a deal, the best tips in the world won’t help you. Because, whether you like it or not, you’ll always be the awkward one.

Oh, and my baby? She’s almost one now. Pretty sure she’s as pumped as I am this year...

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