Since graduation, whenever I hang out with friends, our conversations eventually turn to: “how do you meet new people?” When I ask someone how they are doing, their answer is invariably “good, but I miss having my friends around.”

Making friends is hard. In college, you can befriend someone just for the sake of being friends. After college, relationships suddenly become transactional. You need a reason to meet someone. They, in turn, constantly evaluate what you can bring to the table. I’ve had so many disheartening experiences when I meet someone, they ask what I do, and as soon as I give an answer that’s irrelevant to their businesses, their eyes glaze over.

When a conversation is not transactional, it’s often mistaken for a romantic attempt. When a guy I barely know asks to meet, I sometimes wonder if it’s a date. This mentality also makes me afraid to reach out to guys because I’m afraid they’ll think I’m hitting on them.

The list below is drawn upon many conversations I’ve had. If you have other tips, I’d love to hear them.

1. Do cool things

When I asked a Thiel Fellow how she knows so many interesting people, she shrugged: “I do cool things.” Chris Lengerich, who just finished his six months being an entrepreneur in residence at Khosla to start his own company, told me the same thing. “Don’t try to make connections for the sake of making connections. They’re superficial. Do cool things and people will be attracted to you.” If you aren’t doing anything interesting, what are you going to talk to the person you just met about?

Most of the relationships I’ve built outside schools are from doing things that I care about: through teaching the TensorFlow course, through writing, through traveling, and through doing AI research.

Debnil Sur, my friend at Interstellar, asked: “How do you know that what you’re doing is cool?” I find that almost anytime I try to do something because I think other people think it’s cool, I fail. Whereas if I do something that I truly care about, my enthusiasm attracts people. There are many things I didn’t think were cool until I met someone who was passionate about it.

2. Provide values

Jerry Lu, a Wharton MBA candidate and associate at Lux Capital, told me that his strategy for building meaningful relationships is to provide values: “When I meet someone new, I try to figure out what I can do for that person.” It isn’t rocket science that we’re more inclined to add someone to our lives if that person can add positive net values. Yet, I’m guilty of reaching out to people who can do something for me while I should be asking myself what I can do for that person.

To be able to provide values to other people, we first need to have some values to provide. For Jerry, he organizes events to connect like-minded people. When he comes across something he knows I’m interested in, he sends it my way.

The personal strategy to provide values of the Thiel Fellow Noor Siddiqui is roping her friends in while crossing off items on her own bucket list: “If i’m really excited about climbing a mountain, or putting up street art, will bring along a friend or two that might enjoy it as well.”

It’s not easy to put other people’s needs ahead of my own. I have to constantly remind myself: do someone a favor before asking that person for a favor. I also started copying my friend Lucio Dery to end my messages with “Please let me know if there’s anything I can help you with”, and make a point of seeing it through if someone takes up the offer.

3. Use social media

I know there’s this zen thing going on that encourages people to get off social media. Occasionally, I also feel the need to disconnect from online channels to focus on myself. But overall, social media has given me much more than what it has taken away.

Social media is a tool: whether it’s good or bad depends on how we use it. For me, it’s a way to spread my ideas, explain my work, and above all, sell myself. There exist people who are so good that the world seeks them out regardless. But I’m not one of those geniuses. Most people aren’t. If I don’t get on social media, I’ll just become invisible.

One channel that I highly recommend is Twitter. I’ve met many interesting people who’ve become my friends (shout out to David Dao, Miles Brundage, Joshua Browder). When I share my work on Twitter and it gets retweeted, it almost feels like cheating – I know people who are doing much better work but don’t get recognition.

Thoughtful blog posts are also a great way to showcase your critical thinking and reach more audience. I enjoy any post that shows that the author has thought deeply on the topic and can give me a new perspective or teach me something new. I especially love technical blog posts that turn difficult technical concepts into popular science – these posts show that the author not only understands the concept but also has great communication skills.

Newsletters are making a comeback. John Luttig, an associate at Founders Fund, recently started a weekly newsletter to share one thing he’s learned and one question he’s thinking about. “When people hear from you every week, you’re top of mind and they loop you in on things more often. People are sending me more deals and asking me to hang out,” he told me.

One problem with social media is that it takes time to build the audience. The hardest part is to grow from 0 to the first 1000 followers. Luckily, there are plenty of articles online on how to grow your audience.

4. Don’t try to impress people superficially

One mistake I made initially (and still occasionally) is that I try way too hard to befriend people I look up to. That has never turned out well.

This sounds shitty to write out loud and I know some would be quick to blame it on my insecurity, but I’ve learned to be realistic about who I should try to befriend. I’m not saying that all successful people are snobs, it’s just that I haven’t done enough to interest them.

Omar Rizwan, another Thiel Fellow, summed it up well over our brunch: “I prefer becoming friends with peers, people who are at the same stage in life as me and are working towards the same thing. It’s hard to be friends with people way ahead of me because I have nothing to offer.”

My rule of thumb when meeting someone new: if I feel the need to impress them, I should say goodbye and walk away.

5. Have a strategy for each meeting

My roommate Rex thought it was strange for me to reach out to strangers: “I wouldn’t know what to talk to them about.” It was strange for me to hear that too: “Why would I want to meet someone if I don’t know what to talk to that person about?”

I only reach out to people when there are things I want to discuss. It could be about their current work, something they did, or some specific insights. If we click and become friends, that’s great. If we don’t, I learn something new and I hope they get something out of it too.

Devon Zuegel, who’s currently hosting a show on crypto for a16z, put it beautifully in a tweet:

What are your strategies for having great conversations? A few of mine:

  • Collect good questions and keep a written list
  • Allow for almost-awkwardly long silences; other person will fill them with something interesting
  • Listen for words/models they keep using that are atypical

6. List of questions to get to know someone

Getting to know someone is as much a science as an art. This topic has been heavily studied and you can find zillion of lists of questions that claim to help you get to know someone.

I love Noor’s blog post How to Get to Know Someone. To quote Noor:

I’ve found that good conversations start from questions that get your (future) friend to:

  • recall an emotionally charged memory (positive or negative)
  • recall a rarely accessed memory (nostalgia)
  • generate a novel response (think about something they hadn’t thought about before).

Bad conversations occur when the person you’re talking to is:

  • providing canned responses to questions, having a conversation with you that they have had with someone else a moment ago
  • not learning anything about themselves
  • not feeling understood by you

Her has a list of questions that go from easy (What thing did you buy for under $50 that brought you the most joy/convenience/utility?) to hard (What is the most significant thing you’ve changed your mind on in the last year?) to challenging (What is your most radical belief?).

In that spirit, I’ve also made a list of questions I use when I’ve run out of organic things to talk about. These questions depend a lot on the circumstance we meet. I rarely have to use them, as I’ve found that listening and mirroring the other person is much more effective.

  1. What has made you really happy in the last month?
  2. What are you reading?
  3. What’s something that you’ve learned recently that surprises you?
  4. What’s your story? [Everyone has a story yet in my experience, almost everyone being asked this question for the first time is slightly taken aback. However, if you show that you genuinely care, they might tell you a story that they haven’t told many people before.]
  5. Would your [10 18 20 ..] year-old self be surprised about where/who you are today?
  6. What’s the best career decision you’ve ever made? What’s the worst?
  7. How would you describe your friend circles?
  8. What quality do you value the most in a friend?
  9. What’s the first impression that people often have of you which isn’t true?
  10. What do you think of the stereotype of [the career they are in]? For this question, they might ask back: what’s the stereotype? You can avoid answering this question with: “You should know this better than I do!”
  11. What’s the riskiest thing that you’ve done?
  12. What is the most valuable skill that got you where you are today? [mildly complementary]
  13. Your parents must be proud of you!
  14. What’s the biggest problem you’re facing?
  15. What would you want to change about your life right now? [A lighter version: what would you want to spend more/less time on?]
  16. Is there anything I can help you with?

Closing thoughts

Just as you can’t hack dating, you can’t hack meaningful relationships. No matter how many tips you use, it eventually boils down to whether you’re comfortable in each other’s company. Are you adding values to each other’s life? Are you creating an environment for other people to be themselves? Are you living an exciting life which other people would want to be part of?

I’m nowhere close to being an expert on the topic. I can be painfully awkward at times, which leads to cringe-worthy social interactions, which reinforces the self-inflicted belief that I should stay within my protective shell. But there are two things that keep me going, and I hope that they’ll help you too: 1) other people are just as afraid of getting hurt as we are. 2) every friend that we have now was once a stranger. So open up and put yourself out there. It’ll all be worth it in the end. [Or not.]

Acknowledgement: I would like to thank Edward Lu, Raymond Nie, John Luttig, Noor Siddiqui, Jerry Lu, Chris Lengerich for reading the draft and providing super helpful feedback.