In September, Julian and I hosted our confidence retreat in Madrid, Spain with Kristina coaching alongside us.
Madrid has everything you’d expect about Spain. Warm weather, even warmer people, and legendary food. Even the non-Spanish cuisine was epic. We visited a Japanese restaurant that we all agreed was one of the top meals of our lives.
And yes, it’s true that just about everyone, man or woman, is ridiculously stylish and good-looking.
But for me, all that is not what makes Madrid special. It’s the fact that Madrid has one foot in the past and one foot reaching out into endless new futures.
When you’re in the main shopping areas, you see the most opulent architecture all around you.
I’m talking about fortresses the size of city blocks, intricate molding over every facade, and enormous statues looming over you. I can’t even imagine what some of these buildings would cost in today’s dollars. I mean, who has a seven-story Zara with marble staircases?!?
But then you walk five to ten minutes in any direction and you’re transported to another world. Every neighborhood is completely different from one another. The cuisine, culture, and demographics change from one street to the next.
You can go from business to bohemian, punk to hipster, down-home to luxury in no time.
All this means is that Madrid is a city where you can discover yourself and find your tribe. And for us that provided the perfect backdrop for men stepping into their own brand of confidence.
Maybe you need to stop trying so hard
Towards the end of the retreat, we took turns sharing our most significant realizations from the experience. One of the attendees said something that really stood out.
He looked at us and said, “Coming here I thought I had to try more. Now I realize I have to try less.”
It sounds simple enough, but it’s a powerful lesson that we try to teach men. Let me explain…
He said that when he signed up for the event, he thought he needed to become a “cooler” guy. He thought he’d have to learn to be super witty or know how to always say the most interesting things.
This need to impress people caused him a lot of anxiety. He got stuck in his head about having to respond with a funny quip or a perfectly-worded question.
So during the retreat, we told him to do the opposite.
We told him to slow down and take the time to respond honestly, even if it wasn’t necessarily witty. If he didn’t have anything to contribute to group conversation, we reminded him to relax and just wait until he genuinely had something to say. We instructed him to ask questions HE was curious about, even if he thought they weren’t that special.
What happened? We gave him permission NOT to perform and lifted a huge weight off of his shoulders.
Without all the pressure, he was able to be present with people and connect on a personal level. He was more in touch with his emotions. He could get fired up when he wasn’t stressing about micromanaging his every word.
Almost immediately, his conversations for the rest of the retreat transformed. Without even trying, he was speaking with passion. He got loose and joked around. And whenever he jumped into a group conversation, he made compelling observations that grabbed everyone’s attention.
Without exaggeration, EVERY woman he talked to after that ended up spending hours with him. They didn’t want to leave such a fun time with a guy authentically showing up.
The point is this: we all have a unique personality. That’s interesting enough in itself.
When you overthink things and try to read minds, you end up cutting away all the awesome things that make you…YOU.
There is no one category of attractive person. But confidently expressing who you are will always be sexy and will captivate the right audience.
Sometimes, you need to try less.
If you’re worried about bothering someone, check-in with them
Many men are terrified of walking up to a random woman or group of women to start a conversation. They don’t want to impose or bother them.
At first glance, their fears have some validity.
It’s rare to see random people chatting nowadays. So when guys do try to introduce themselves, some women are surprised at the unexpected hello. It doesn’t mean they’re completely against it, it’s just not an everyday occurrence for them.
In response to this, you may try to gauge whether or not you should go talk to a specific woman beforehand.
You try to guess: What’s her body language saying? Is she making eye contact? What kind of expression does she have? How many friends is she with? Does she look busy? Does she look friendly?
This guessing game almost never works. All it does is give you more anxiety and convince you to give up before you’ve even started.
So lately, I’ve been experimenting with an awesome way to solve this problem. I’ve devised a way to know whether or not a woman wants to talk to you while also giving her an easy out if she doesn’t. I call it…
“Lead, then check-in.”
Basically, walk over and tell the person what you want to say. Then right after, check-in to see if they want to continue the conversation or if it’s okay to join their group.
I’ll give you a few real examples from the retreat:
- At the market, we saw two girls standing with their mother. A couple clients wanted to talk to them but were worried their mother might take offense. When we first said hello, the group was a bit standoffish. I immediately followed up with, “We just wanted to meet some new people. But if you’re doing a family vacation thing, no problem.” They immediately relaxed, initiated more conversation, and we happily talked for 20 minutes.
- We saw two girls sitting, eating in the park. We walked over and one of the guys said, “Hey, we don’t mean to interrupt your snacking session. But we were wondering if we could join you for a couple minutes.” We hung out for a while and traded contact info to meet up later.
- Julian and I were with a couple of guys talking about relationships. We saw five girls sitting together on the grass near us. We walked over and said, “We were just talking about relationships. But we’re a bunch of guys, and we’re wondering if we if we could get a better perspective from you.” They warmly welcomed us, enjoyed a 30-minute conversation about romance, and kept talking even when their three other friends arrived, too.
In general, a few honest check-ins are all you need. Such as…
- “Would it be cool if I joined you for a quick coffee?”
- “Is it okay if I sit with you for a moment?”
- “Can we hang out and talk with you for a few?”
This is not a weak move. You are showing courage for doing something that most men don’t. But then, you’re acknowledging that you know this is unexpected for her and want to see if she’s in the mood to talk.
This signals to women you are both self-aware (which shows you’re conscious of social norms) and respectful (which shows you will not cross their boundaries if they’re uninterested).
This builds trust and makes people feel more comfortable with you. I’ve also found that this check-in disarms people’s defenses and makes them much more likely to engage in conversation.
Real talks with strangers make you happy and attractive
Six months before the retreat, I took a vacation to Madrid to scope out the city and see if it would be a good fit.
I ended up at a tiny hole-in-the-wall coffee shop. The espresso was heavenly. I was genuinely excited to learn about the owner and his craft, so we got to talking for a few minutes.
I found out he was originally from Barcelona and missed the more laid back attitude there. I shared how I loved their wild architecture and endless creativity.
I learned that his name was actually German from his grandfather. I listened to him talk about how he searched for the best hot chocolate and now sources it from Australia.
Then months later, a couple days before the retreat, I returned there with the team. I told them about how good his drinks were. But I did not expect what happened next…
The moment I walked in, he lit up and exclaimed, “Nick!” I was floored that he recognized me.
He must have had thousands of people in his store since we’d met. Yet he somehow remembered who I was from a five-minute conversation.
I’m sure I’m not the most interested person he’s ever met and I don’t have a memorable face tattoo. All I did was show a stranger that I gave a shit about who he was. I moved past the normal small talk routine and got the slightest bit personal and real.
That’s often all it takes to stand out in a stranger’s mind.
So many guys I talk to only worry about meeting women. They rarely see the value in becoming more social with everyone. Yet the men I know who are seen as the most charismatic do just that.
Those men become well-liked and known in different local spots. They have the attention of working people. They get free drinks. The workers introduce them to other people. And they look like a baller to other people and women around them without even trying.
This is the essence of “social proof”. When people see that you are liked by others, they are infinitely more likely to see you in that same light and give you a chance.
I have two examples of this:
- One of the retreat attendees frequents a local cafe near his home. He knows the owner well. One day, he was sitting next to a local celebrity who also happens to be a gorgeous woman. The owner and a worker walked up to him, comped him some food, and exchanged jokes and conversation. The beautiful woman nearby started paying attention. Our client looked over and made a simple comment about how the avocado toast is to die for. Because he was already approved as a great guy by the staff, she responded with enthusiasm and chatted him up. They ended up enjoying breakfast together.
- A recent client started going to spin class. He was the only guy out of about 30 people. He started talking to the instructors as a newbie and asked them questions about how they got into it and what he should be focusing on. Because he was interested in their passion, the instructors started talking to him after class over the next two weeks. The other women in the class took notice and started talking to him, too. Without even trying, he now gets surrounded by women. He told me that multiple women have openly shown interest in him and are making plans to get together.
Take a couple minutes out of your day to talk to strangers. You never know where it will lead to. At the very least, it’ll put a smile on both of your faces.
Stop racing to the finish line and enjoy the ride
One attendee pulled me aside towards the end of the retreat. He’s a brilliant guy who tends to be very logical in his thinking. Because of that, he’s accomplished a tremendous amount in his career.
In life, he’s always set goals and then figured out structured frameworks and specific steps to achieve them.
He came to the retreat thinking of self-confidence and human connection in the same way.
He set a concrete goal for himself: in three months, he would have all of this figured out. By then, he’d know how to be perfectly confident in every situation. He’d know exactly what to say to women. He’d know how to flirt seamlessly and be smooth all the time.
But through our work together before and during the retreat, he saw that this area of life doesn’t work like that. Despite great advice and implementation, the results were not always consistent. Sometimes he’d feel more nervous. Sometimes people didn’t click with him. The same flirting formula didn’t apply to every woman.
He hated this process. He just wanted to rush through it and get to the finish line. So what we taught him was this:
Humans and their relationships are all about emotions. We are all different. We all have unique personalities. We are influenced by our environments.
Even though you can adopt a healthy mindset and learn the practical skills for confidence, there is no one-size-fits-all approach to human connection.
Instead, you need to grow over time through experience. You need to talk to lots of different people to develop your emotional intelligence. You need to explore what it means to express your true self by sometimes getting it wrong and sometimes getting it right.
For our client, this lack of a clear-cut end goal was totally demoralizing. But during our time together, he was able to let go of his frustration and embrace the journey ahead. He realized that our personal growth and ability to connect with each other is a lifelong process.
And once he accepted this, he started to measure his success on whether or not he was improving day-to-day and week-to-week. That mindset shift finally made him love just being in the moment with new people.
Now, every day brings something new for him to look forward to. Every day that he puts himself out there is a WIN.
You won’t overcome your fear of meeting people if you’re not honest with yourself
We talk a lot about the importance of being honest with people. But sometimes, you really need to be honest with yourself.
When we try to help men connect with new women, they often have a lot of excuses. And we know that’s natural when they’re trying to avoid something they’re afraid of.
Early in the retreat, there were times when guys were nervous and tried to tell us they didn’t want to talk to certain women.
While at a bar, two guys were sitting away from the crowd talking to each other. We asked them if they were going to come mingle with us, and one guy replied, “We’re not avoiding anyone, we just want to chill out right now.”
I get that wanted some bonding time, but they had plenty of opportunities outside of this two-hour window to do so. They had been chatting during meals and in between sessions. So I challenged them and said,
“Listen — you did not fly hundreds of miles and spend thousands of dollars to come here and sit around talking to only each other. It’s okay if this is overwhelming right now. We’ll just take our time and ease into things.”
I got them to both admit they were in their head and felt nervous.
Another two clients kept letting opportunities to talk to beautiful women pass them by. They told me those women weren’t attractive to them. So I challenged them and asked…
“If those women walked over and wanted to talk to you, would you respond to them?” They said yes. “If they asked for your number, would you give it to them?” They said yes. “If they invited you home tonight, would you take them up on their offer?” They said yes, with a sigh.
One guy replied, “Agh, well when you put it like that…I guess it’s just so hard to get up and do it.”
I told them, “It’s okay to feel uncomfortable or afraid. That’s why we’re here: to slowly challenge ourselves and expand our comfort zone.”
In both of these instances, the men were able to break out of their mental rut and start taking action. They really heard me when I called them out on their excuses.
You need to accept when you’re not being honest with yourself. You need to call yourself out on the lies that you think are protecting you.
Let go of your pride and your ego. Realize that your internal monologue of endless excuses and justifications is preventing you from moving forward in your personal development.
Come to terms with feeling afraid. There is absolutely no need to be fearless, you just need to find small ways to take courageous action despite those fears.
Only when you accept your weakness can you find your strength.
Everything’s better when you’re with great people
Just like in personal development, we always try to improve each retreat. We want to stay humble and keep increasing the value we can deliver.
This time around, we added a fashion expert, Alexandra Vail, to the experience.
She showed the guys how style can be a tool to communicate their personalities. She taught them about fit, color theory, and what worked for their body type. Then they shopped for incredible outfits which made them feel great for going out (and also look super sharp in their photos!)
While many of the guys already had good style, learning from an expert takes things to the next level.
And that’s the reason these guys are seeing more success than ever — because of the amazing team involved.
Julian, our co-founder, continues to build our vision for making the world a better place, one honest connection at a time. His message of developing a fulfilling lifestyle is profoundly shifting the way men think about interacting with women.
Kristina is the best damn coach at getting men to understand women on a deeper level. I’m always amazed at how she pinpoints what a guy needs to improve and immediately practices those skills with him. In record time, she teaches men how to apply their knowledge with the women they meet.
Our photographer Sarah Katharina magically makes everyone look like models in their photos. Clients instantly find success in online dating with her profile pictures. In addition to her impeccable eye, her secret sauce is how she makes us all loosen up and get goofy.
And Will Gay, our videographer for this event, understands his craft on a level I’ve never seen before. He has boundless technical knowledge – watching him shift lenses, adjust settings, and get the perfect shot every time is a spectacle in itself.