Today’s guest used to suffer from crippling shyness that left him unable to have even basic conversations with strangers.

Today, he’s an expert in social theory and the author of Superhuman Social Skills, a practical guide for anyone looking to increase their social circle and get comfortable socializing in any context — whether with friends, business partners, or complete strangers.

This episode isn’t just for those who suffer from social anxiety; it’s for anyone who wants to get more out of life by establishing deeper connections with the people around them.

Listen in as Tynan teaches us:

  • How anyone can overcome crippling social anxiety
  • A simple method for winning over new friends and becoming a social superstar
  • How to tell better stories

How did you get superhuman social skills?

I was very shy and had social anxiety all the way from my early childhood to college. If one of my friends brought over one of their friends who I didn’t know, that would be a pretty uncomfortable situation for me, especially if that friend happened to be a woman, and especially if she was single.

I just had nothing to say, so that was very difficult for me.

As you can imagine, my dating life sort of followed suit which eventually led me to get involved in Pickup because I realized that if I didn’t fix my social skills, particularly around dating, my life wasn’t going to end up where I wanted it to be.

So, when I was first exposed to this whole Pickup thing, it was the first time I realized that social skills were a learnable skill.

Before that, I thought you were born with whatever social skills you had and that was that.

But I went really deep into Pickup (which you can read about in the book The Game) and it totally transformed my dating life but it also transformed my relationships with my friends, with my family members, and especially with new people.

My fear of talking to strangers was gone.

It’s funny because I now meet people and they find it hard to believe I was ever shy, but it’s true! I really started off pretty bad.

Can you give us an example of how your lack of social skills affected your life early on?

I have tons of those moments. That was my entire high school experience basically.

One that really stands out was the tipping point for me actually, and the reason that I eventually got into Pickup.

There was this girl the summer after my last year in high school, and for whatever reason we started hanging out. Almost every day that summer she would come pick me up in her car and we would drive around and basically just do nothing. I had a massive crush on this girl, but I had no idea what to do about it.

It wasn’t even that I was thinking about what to do. I knew that I had no idea what to do, so why even think about it?

Finally, the end of the summer is approaching and we’re at this party with all her friends, so I’m feeling very awkward. I’m not talking to anybody. But then this girl takes me into this hallway and she says, “You know Tynan, I have something to confess to you.”

I thought, “Oh my god, what could this be.”

She says, “Well, I have a huge crush on you” and I said, “Wow, that’s great, I have a huge crush on you, this is amazing” and we kissed.

A couple stands affectionately together.

Wow, what a high point for me and I remember thinking, “This is great, this is my new girlfriend, I have this great girlfriend now, we’re going to date, and it’s going to be just like the summer.”

The next day she went off to school in Chicago while I lived in Austin.

I thought “Well, okay, that’s a problem, but it’s not insurmountable obviously, we’re going to end up together eventually.” But we didn’t really talk. We’d email once in a while. She got another boyfriend and I thought, “Well, you know, it’s natural, she’s at college, of course she’s going to have a boyfriend. She’ll break up with him and then we’ll start dating.”

In my mind it was like this: “Hey, this girl likes me, I like this girl, this doesn’t happen, this is such a rare event, it obviously means something.” I genuinely thought we were going to be together in the end, no matter what.

I didn’t have that much awareness of how the world worked or what was actually going on. I think it was easy for me to blind myself to reality, and it became increasingly difficult for me as time when on. I found out she moved in with this guy, which is obviously a warning sign, but it wasn’t until she was engaged to this guy that I finally thought, “Wait a minute, this isn’t going to happen is it?”

It all just kind of clicked at once and I thought, “Man, this whole thing lasted three years. If my life continues on like this, it’s really going to be bad.”

The interesting thing about Pickup is you get into it and you try to get all your friends to do it and nobody does it because it’s hard to do unless you really hit that low point where you can admit, “Hey, this thing that’s very core to my identity is a real weakness for me and I’ve got to get better at it.” I hit that low point because of this girl.

What was it like when you first got into the Pickup scene?

I would read all this Pickup stuff online. I was so naïve back then. It really didn’t occur to me that people were exaggerating and lying. People wrote stories like “Hey, I’m this nerd, I like computers, I met this model and now she’s my girlfriend.” And I believed it.

So I knew I wanted to try this Pickup stuff myself, but I was way too shy, too nervous, to actually talk to girls myself.

Eventually, I found a local group of guys in Austin who would go out regularly to practice talking to girls.

Since I knew that there was no way I was going to face my fears alone, I signed up for this group even though I was actually terrified to just meet these other guys. I remember I almost didn’t go. But I forced myself despite my fear.

I remember walking into an apartment and there are eight guys sitting around telling their own version of the story I just told you.

When it came time to tell my story about why I was there, my face became so red that I couldn’t even look anyone in the eye. I was just so nervous talking to these strangers, and we hadn’t even gone out to talk to girls yet.

So we finish going through everyone’s story and there’s a knock at the door. Somebody comes in late and it turns out to be my best friend. We stare at each other like, “What are you doing here?” It turns out that he had gotten into Pickup before I had, but we were both much too embarrassed to talk to each other about it.

But I think having him there really helped. I was glad he was there because I could say, “This is somebody I know, who I trust, who I relate to and maybe this will be something of a shared journey.”

So finally we get to this club, Spill in Austin, and I’m terrified. I’ve never been to a club or even a bar before. I’ve never even talked to a girl I didn’t know before. I mean, my heart rate is at 200 bpm.

I literally thought I was going to pass out.

Then my friend who’s actually been talking to girls for a month or so previously says, “All right, let’s talk to some girls.” and that’s when the panic really set in.

My brain was trying to come up with any excuse to not do it.

So my friend goes first, which is a great relief to me, and talks to these four girls at a high-top table. I’d never seen him talk to a girl before. He and I became friends because we were first in line for Star Wars together, it blew my mind. But I was happy because I was off the hook until three minutes later, he says, “Actually, my friend Tynan is here too, come over here, Tynan.”

It was terrifying, but I had no choice, so I go over I talk to these girls. I immediately forget everything I’ve read online and learnt about Pickup. I think I did everything wrong. But after a while the guy who was hosting the meeting comes up and whispers in a very loud voice, “Hey dude, she’s into you, ask for her number.”

She hears this, my face is bright red but I go for it, “Hey, do you want to give me your number? Maybe we could hang out sometime” and she did.

And in that moment, I thought, “Oh my god, this really works, this could work for me.”

I was actually talking to that friend a couple of nights ago and I told him if it wasn’t for that moment, I don’t think I would have ever gotten it. I would still be that shy, embarrassed nerd that I was in high school.

How did you build on your early social success?

I don’t drink, I hate bars and clubs, it’s not an environment I enjoy, so I’d go to Whole Foods and I’d go to malls and just talk to people. At the end of the day when you’re practicing social skills, you just need to talk to a lot of people.

I guess I learned the skills early on in bars and clubs but it was immediately obvious that it was a universal skill. People often think of Pickup as, “What’s the line?” and all these deceptive tactics.

But Pickup is really about being proud of yourself as an individual, and if you’re not proud of yourself for legitimate reasons, it’s about becoming someone you can be proud of.

Once you’re proud of yourself and you’re happy with who you are, the next step is being able to express that to people in a positive way.

How can you tell stories that explain who you are in a way that is entertaining to the other person at the same time?

How can you focus on the positives and reveal the weaknesses but not dwell in them in a way that makes you seem insecure?

Then there’s the whole other half of learning about the other person. You have to ask yourself, “What do they want out of this conversation, what do they want out of this relationship, and how do I get them that?”

Those skills are obviously very valuable in dating, but they’re also totally universal. I do the exact same thing with my friends, my family, people I’m doing business with, everybody.

How can we become proud of ourselves?

There are two sides to that question.

One is asking yourself, “Am I living my life by my standards? Am I happy with what I’m doing with my life? Do I spend time in a way that I’m proud of? Am I learning the things I want to learn? Do I treat people the way that I would like people to be treated and I want to be known for treating people?”

It’s a big topic and it’s something that takes people years and years to change. A lot of people are proud of most of these things but then they say, “You know, I’ve got these bad habits, I cut people off, I have a bad temper.” Whatever it may be, you almost always have something you can work on.

The other half of becoming proud of yourself is understanding that what people really want is to know who you are as an individual.

Part of the reason I was so shy when I was younger is because I grew up watching movies and TV shows where girls always went for the guys who drove pickup trucks, go to bars, party, and watch sports. Well I didn’t do any of these things, so I wasn’t really proud of who I was, or at least I didn’t think I had anything to share with girls.

Subconsciously I thought, “Well these are the things girls are in to, I don’t have any of them, I guess I better just stay quiet.”

I mean, I was conscious of the fact that movies and TV are totally fake, but subconsciously maybe I wasn’t?

So it’s a two-step process of:

1) making your life a life that you’re proud of, and

2) giving yourself credit for what you’ve got.

I’ve always been a nerd, and maybe before I would try to hide that but now I’m proud of it, I think it’s really cool.

What was the transition from shy nerd to social butterfly like?

Well, it certainly wasn’t an overnight thing where you tell a story, someone responds positively and you say, “Hey, I’m cured, I’m just going to talk about myself all the time now.”

Growing up I wasn’t the most positive person in the world.

I wasn’t super negative but somewhere in the middle, and I think that held me back. So I started doing this exercise with myself where I would always try to see the positive side of everything for one month. Just for practice.

After the first month I thought, “Hey, I think this is kind of helping,” So I did it for another month, and another, until it was almost second nature. After that it was automatic.

What I’ve found with my coaching clients is that everybody has a natural set point along this continuum of negativity to positivity. And a slight shift to one side or the other side makes a world of difference. So, if you can go from slightly negative to slightly positive, that’s huge.

Here’s something anyone can do right now to start shifting their set point from the negative side to positive.

At the end of each day, write down every time that people around you appreciate you for who you are. It doesn’t even matter that you’re writing it down, you can never look at it again. The point of it is that if you know that you have to write that at the end of the day, it’s training your brain to think of those times throughout the day and to be looking out for them.

Because it’s not that people don’t get positive feedback throughout the day, it’s that they don’t see the feedback.

I know people want quick fixes but if you can do this for a month or two, you’ll be fixed for life. I can’t remember the last time I had a negative thought because I do this practice every day and this one thing had a huge impact on my transformation from being too shy or embarrassed to talk about myself to being comfortable putting myself out there.

What’s the biggest takeaway from your book, Superhuman Social Skills?

The most important piece of advice in my book is that you have to be proactive in your social life.

Your social life is so important, it has such a big bearing on everything you do. Even if you are super successful financially, you are not going to fully enjoy that unless you have friends and families to share that success with. It’s such a crucial part and yet a lot of people aren’t proactive about it.

So in general, be proactive, take responsibility for your social life. One simple way to do this is to have a weekly event that you host and invite all of your friends to. It doesn’t have to be fancy or involve a lot of effort.

When I lived in in Austin and Sopranos was on TV, I’d cook Italian food and I’d invite all my friends over to watch Sopranos. It was like this big weekly thing. More recently when I lived in San Francisco, we just went out for burgers every Sunday at the same place. It really doesn’t have to be a big deal.

“It seems like everybody wants to be invited to stuff, yet nobody wants to be the one to put themselves on the line to host even simple events.”

But here’s the thing, there’s no way you can lose by inviting all of your friends to do one weekly thing. And what’s more, you now have this anchor in your life that you can use when you meet someone new.

It’s no longer, “Oh God, how do I invite this guy I just met out to do something, I don’t want him to think that I am asking him on a date.”

It’s now, “Hey my friends and I have burgers every Sunday why don’t you come along this week?”

So easy.

So just be proactive and be willing to be the one who does the work.

How can I start telling better stories today?

The basic structure of a story starts with the setting of the story. This should be as short as humanly possible.

For example: “I was with my friend and my uncle at a lake.”


I don’t need to know what your uncle’s hobbies are, what his job is, or how long you’ve known your friend for. All irrelevant. I just need to know the basics of how we arrived at the beginning of the story.

Too many people flood their stories with details that we just don’t need to know. They don’t add anything to the story, and most of the time they detract from the core message.

Then the next phase is the lead-up. This is the part where you get to the point of why you’re telling the story.

So, for example: “There I was, I’m standing in this restaurant and all the way across the room I see this guy that I knew from high school.” Note that I’m building suspense here by leaving out irrelevant details.

But this part of the story should also be the longest part. As long as you have the listener’s attention, you want to build attention and leave them wondering. It’s like when you watch a movie and you think the main character is about to get killed but you still have to watch moment-by-moment because you don’t exactly know when or how it’s going to happen.

Even if the person already knows the end of the story, you can really draw this part out to make it emotionally interesting. A story is not about facts, it’s about an emotional experience. So this is the part where every single thing you say should make the listener more emotionally invested in the story.

Then you get to the point of the story, the drop, the hook, or whatever you want to call it. The key here is to give your listener the hook and then stop.

A lot of people screw this up by rambling at the end after the listener already knows the point of the story.

It’s much better to keep the beginning short, the tension long, and end right after the hook. You don’t have to explain every detail because you can let people ask you about details they want to know more about.

You can give people opportunities to direct the conversation by leaving out details rather than you monopolizing it.

How can someone be vulnerable in conversation without appearing weak?

Two people in conversation.

The difficulty in being vulnerable is that it’s about sharing something that’s unique to you. So it’s going to be different for every person, but I think a fairly common area you can start with is your family.

You have such an emotional connection to your family, so if you talk about a family struggle or even a relationship that you have with like a younger person that you mentor in your family, that can go along way to establishing a deeper connection with your listener without making you appear weak.

There’s a big difference between, “Hey we are trying to impress each other by telling grand stories” and, “I am telling you something real about my life, about people who are close to me.” I think most people can probably find something in that second realm to share.

What advice would Tynan give to aspiring authors?

I think everybody has a different writing style, but I prefer to write more practical books and to get them writing-quality wise up to about 90%. People really like my books because they are super practical and actionable: “Do this, do that, here’s how things actually work” and they get results.

One piece of advice I would give other aspiring authors is to give yourself a deadline. Write every single day until that deadline is done and then spend a short time editing before putting your book out.

My more recent books are good because I’ve written some books that weren’t quite as good as those books, and those books were okay because I wrote some pretty bad books at first. Don’t worry about being perfect, just get your work out there on Amazon or wherever.

What’s your next book going to be about?

The first book I wrote was called Make Her Chase You. It was about Pickup and I wrote it more to make money than anything else, but since then I don’t really care so much about money. Obviously, I like money and making money, but it’s not my number one priority.

What I really want to do is to write books about stuff that I am in to and excited about that will help people. That’s my motivation.

It’s funny because I go really deep into a certain topic because that’s my personality, so every time I write a book I think, “Well I guess that’s it. I probably have nothing else to write about,” and then I get super into something else.

For the past while I’ve been super interested in social skills, but to answer your question, I don’t know. I’ll just write about what I’m excited about.