This past week, I took my first trip down to Austin for SXSW Interactive. I learned a lot of lessons while at the conference. After all, you can’t help but soak in a lot of learning when you’re with 30,000 of the leaders and peers in your industry.

I initially thought my SXSW event recap would be a first-timer’s guide to conquering SXSW. But, honestly, what I discovered is that it’s not about the panels or parties or celebrities or startups at all. It’s about human relationships—how people engage with one another, and why people do what they do. SXSW is basically one giant semi-professional, semi-revert-back-to-college-behavior social experiment.

My goal was to create an incredibly useful event recap for people. After meeting well over a hundred total strangers and several tech “celebrities” this past week, I realized the most useful thing I could write about is what I learned after 96 hours’ worth of careful observation about how people interact with one another. So, here they are—the eight lessons I learned about building relationships in the startup and tech community at SXSW:

1.) It takes quality time to really get to know someone

I learned this week that I don’t really love big events with tens of thousands of people. At all. The whole thing feels super overwhelming and the opposite of productive. SXSW is like spring break for nerds, and that’s about the extent of it. You might be able to create a totally useful experience where you soak up amazing learning, close business deals, and connect with incredible people over long meetings. But it would be pretty damn hard. That’s like finding a golden ticket in a sea of 30,000+ people. It could happen, but so can winning the lottery.

Almost everyone I talked to said the same thing: “It’s all about the parties.” But, you know what happens when you think it’s just about the parties? You get, on average, about 5-15 minutes at a loud event to get to know someone new. Sure, every now and again, you’ll get into an unforgettable conversation that lasts for hours. But, from what I observed, that kind of experience is the exception and not the norm during SXSW.

The problem is, you don’t really get to know much about a person in 5-15 minutes. Here’s the general order of conversation: (1) Exchange pleasantries about how crazy and exhausting SXSW is; (2) Ask where person you’re talking to lives; (3) Try to find something interesting and/or funny to say about the place that person lives and compare it to wherever you live; (4) Play the “what do you do?” game; (5) Size them up to see if a person is successful and/or could be a potentially valuable contact for you. If you deem the person important and/or really interesting, you give him or her a business card. If not, you politely exit the conversation as quickly as possible so you can find someone who is.

This is the worst way ever to develop authentic relationships.

I myself made the mistake of asking the “What do you do?” question too quickly in the conversation. Because that’s what’s expected. That’s what you’re supposed to ask. Looking back, I really wish I had asked a better question, like, “What makes you come alive?,” or, “If you could create any company other than the one you already started or work at, what would it be?” It’s a lot more random, but hell—it’s a much better way to get to know people more deeply if you’ve only got 5-15 minutes. And I’m willing to bet you’ll stumble into great conversations that last much longer than 5-15 minutes if you ask questions like these instead.

It takes more than 5-15 minutes to really get to know someone. There are far more interesting, incredible layers to who people are than where they live, what they do, and how many followers they have on Twitter. If you don’t have a lot more time than 5-15 minutes, don’t assume you know much about who someone is—unless, of course, they very blatantly shower you with rudeness, or arrogance, or total disinterest. If they do any of the above, it’s safe to say you can learn a lot about them in 5-15 minutes.

2.) You should bother making plans. 

The other thing people said over and over again was, “Don’t bother making any plans.” I think that’s just about the worst advice ever. What I think people really mean when they say that is, “leave room for serendipity.” But, I don’t think those two pieces of advice are synonymous. You can have some semblance of a plan and still have hundreds of opportunities for serendipity. In fact, I’d argue that if you go in with at least a rough plan, you’ll increase your opportunities for serendipity. Think about it: are you more likely to meet an incredible new contact at some random party you get swept up in with a random crowd of people? Or, at a small meetup with people who have very similar interests? Are you more likely to connect with someone at a loud rager at 3am? Or at an intimate lunch gathering curated by one of your acquaintances? Exactly.

I went in without a plan because that’s what people told me to do. Halfway through the trip, I realized that was not going to work for me. So, I sat down for an hour, wrote a daily list of some of the events, panels, and meet-ups I found most interesting, and I let that loose schedule be my guide. Of course, I wasn’t rigid about it. If I got caught up in a great conversation at one event, I didn’t rush off to the next party. If I found a place I really liked, I group texted a bunch of my friends to come join me instead of me going to chase after them in a dozen different locations. But, in the process of figuring out what I wanted to learn, who I wanted to meet, and the things I wanted to do, I was able to win back some control in the chaos that is SXSW. And create more opportunities for serendipity in the process. Almost every interesting person I met, I met during the second half of my trip.

3.) …But don’t bother with people who don’t ask you questions

Unless you’re a journalist and you’re interviewing someone, be weary of people who don’t ask you any questions. I had a few incredibly awkward conversations at SXSW that were heavily one-sided. I’d ask people questions to get to know them better, they’d respond with answers—usually brief ones, and that was about as far as the conversation ever went.

Of course, sometimes, it might just take a person a while to warm up to you and get in the groove of the conversation. Maybe he or she is shy, distracted, just woke up from a nap, whatever. Be kind and open. Give people a chance to warm up to you. Tell them about yourself first. If, after more than five minutes, they still aren’t budging, it might just be a lost cause with a random stranger at a big event. That’s okay. Politely dismiss yourself from the interaction, and move on to the next conversation.

The people I’m really referring to, though, are the ones who talk your ear off for 15+ minutes about themselves, like they’re trying to pitch you on themselves or their company, without making any real effort to get to know you. Every good relationship is reciprocal—even your newest ones. Don’t try to force conversation with people who only seem interested in running you over with their own agendas and aren’t really there to foster a connection or cultivate a great, two-way conversation. It’s not worth your time.

And if you’re reading this and you’re that person…don’t be that person. It’s super lame.

4.) “Successful person” does not equal “awesome person”

After listening to a ton of my friends and watching my Twitter feed for a while, I began to notice a common theme at SXSW: everyone wants to connect with super successful people. You know, the authors who write bestselling books, the startup founders who are now running multi-million-dollar companies, the c-suite executives at large corporations. Everyone chases after them. I’m really not sure why. What’s the value in that for most people? Maybe you’ll get a few minutes to pitch your idea or try to build a connection, but the chances of it being worth the time and effort are slim.

Just because someone is highly successful doesn’t mean he or she is an awesome person. We’re stuck in our thinking that these are the figures we should look up to and aspire to be like. If you, like the overwhelming majority of SXSW goers, aren’t part of the tech elite, it’s easy to catch the envy bug. The thing is, I’m really not convinced those are the people we should all be envious of. A level of respect for them? Absolutely. But, I observed and listened to stories about disappointing run-ins with tech celebrities who were rude, thoughtless, and even blatantly offensive. That kind of behavior is not cool—no matter how famous or accomplished you are.

Every now and again, you find a very successful person who goes out of his or her way to make a difference with others. Gary Vaynerchuk, for instance, held a 5-hour Q&A session to give random attendees personal, one-on-one advice. Ramit Sethi hosted a meetup for about 50-100 of his blog readers; I watched him make his way around the room and do the best he could to connect with as many of those people as possible. Super successful people like these guys are the ones worth looking up to. Maybe you don’t like how opinionated they are or how they sell whatever it is they sell, but you can’t say they don’t care about connecting and making a difference with people who likely don’t have a ton to offer them in return.

People who give a crap are amazing. Seek those super successful folks out.

5.) Dress in a way that accurately represents who you are

Look, the reality is, at a place like SXSW, you only have so much time to make a first impression. This is true pretty much always, but it’s especially true at an enormous conference. So, maximize the time you’ve got, and wear your personality on your sleeve.

Wear a hat with a bit of charm. Put on a pair of yellow jeans if you’ve got a really optimistic, happy personality. Throw on your favorite pieces of jewelry. Wear comfortable shoes that still express who you are; exchange plain sandals for neon sneakers if you’re loud and proud. Throw on a shirt with a funny expression, like this:


And still, dress appropriately. SXSW might feel like spring break for adults, but it’s still at least partially work-related for most. The last thing you want to do is run into a client, old boss, or potential investor while running around in short shorts or a t-shirt with a funny-but-offensive slogan on it. Want to look relaxed, but still professional? Throw a blazer over your t-shirt. Or a leather jacket over a button down shirt. Or a pair of heels with your jeans.

If you want people to spot you in a crowd and learn something about you before you even say “hello,” use what you wear as an opportunity to make a statement. Dress like the person you are. Dress like the person you want to be.

6.) Don’t get caught in the VIP trap

No matter where you go, you’re probably going to wait in a line at some point during the week at SXSW. When you see a handful of people walk straight up and into a door at a party, it’s hard not to feel some twinge of jealousy and/or unworthiness. The minute that feeling starts to come on, talk some common sense into yourself. For some parties, I wasn’t on a list and had to wait in a line. For others, I was on a VVIP list (yup, apparently those exist), and I still had to wait in a line.

Make the best use of your time. Get to know the people around you if you’re waiting. Bring a bunch of friends along with you. Skip the parties with the hour-long lines and go on an adventure for another great spot instead. Plan dinners with a bunch of friends you haven’t caught up with in a while; tell them to bring a guest or two. Make use of those lazy afternoon hours, and meet interesting people for coffee or ice cream.

Whatever you do, don’t waste too much time vying for a VIP spot at a party. If you can connect your way into a place, fantastic. But, if you don’t get in or don’t want to wait in line, don’t fret—there are 29,000 people who aren’t going to that party, either. Personally, I’d take an intimate dinner over a really loud, crowded party any day of the week.

While everyone else is busy trying to be a “very important person,” just be one. Understand that pretty much everyone deserves to be considered a VIP—everyone matters. Most of the people at SXSW are doing something pretty cool, and anyone who doesn’t agree is probably not that much fun to hang out with, anyway. Be the person who curates a group of amazing people to have a fun brunch or night out on 6th street, instead.

Don’t worry so much about being considered a “VIP.”  Be the person who makes other people feel like VIPs, instead.

7.) You’ll connect with the most unexpected people, in the most unexpected ways

However you’re imaging the experience you think you’ll have, it will almost certainly not go down that way. If you’re an artist, you might meet your future front-end developer for that new art project you’re working on at a random web dev party you walked into—all because you were promised free beer and tacos. If you’re sitting in a lounge catching up on emails, you might just sit next to a fascinating blogger and get into a two-hour conversation. If you get stranded in the middle of downtown Austin at 4:30 am because there are no cabs in sight, you might meet a future really close friend while waiting on an enormous taxi line.

The point is, you can’t predict what you’ll get into. You can’t predict who you’ll meet or how much you’ll impact one another down the road. You can’t predict which acquaintances you’ll become closer to.

All you can really do is view every moment–every opportunity—as a chance to connect with someone as authentically as you possibly can. If you stick with only a group of people you know, you won’t leave much room for meeting new people. If you’re busy staring at your smart phone on a line, you won’t appear that welcoming to the people standing around you.

Don’t try to predict how you’re SXSW experience will go. But if you do expect anything, expect to foster some of your best connections with the most unexpected people, in the most unexpected ways. Life usually surprises us like that.

8.) It’s not your job to make people like you

When you’re part of a sea of almost 30,000 people, it’s easy to get lost in the shuffle of things. It’s also really easy to lose yourself in the midst of all the parties, panels, and people.


Stick to your guns. Do whatever excites you. If you don’t like a party, leave. If you don’t want to drink, don’t succumb to the weird pressure to drink just to fit in. If you want to go to bed before midnight, go to bed before midnight. If you want to go to a panel instead of a party, do it. If you find yourself in a group of people you’re not having fun with, remove yourself and find a group that suits you better. If people aren’t giving you the time of day, go find ones who genuinely care. If someone tells a joke that you don’t think is funny, don’t feel like you need to laugh.

Don’t lose yourself in the chaos of the event. Remain grounded. Remain exactly who you are, and proudly share who you are with others. Because, as with any other scenario in life, it’s not your job to act however you think you need to act to get people to like you. It’s your job to be unabashedly and respectfully yourself. 

And the people who love the person they meet when you’re just being you? Those are the people you should like.

SXSW can be an overwhelming experience. But remember, at the end of the day, it’s not about the amount of stuff you do, the panels you attend, or the parties you get into. It’s about the people you meet in the process of doing all of that. If this past week taught me anything, it’s that what matters most is maintaining your ability to be totally yourself, and asking the right questions to get to know other people for who they really are, too.

Finally, know that mastering SXSW is ultimately all about knowing how to do this one very simple thing with the awesome people you meet: