How to meet 50 Interesting People

How to meet 50 Interesting People

How to meet 50 Interesting People

We’re doing a deep dive into a strategy I used to meet 50 interesting people in a year.  It came at a REALLY important time. I had just moved to a new area. I was trying to launch my business but I didn’t know anyone and no one knew me!  I HATED (and still do) typical “networking” style meetings, so I needed to find a different way.

I uncovered a strategy along with 5 specific questions that made all the difference.  It helped me to connect with some incredible people and grow some rich relationships. Plus, this “people-meeting” strategy was sustainable for me… even though I’m a PROUD introvert!

In this episode, I will walk you through the story, the strategy, and the questions that I still use every week!  We all know that if we want to make an impact in the world… we can’t do it alone. This strategy will help you to build your tribe, make some new friends, and have a positive impact on the world in the process!



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“Tell me something I should know about you.” 

“What’s something you’re working on right now?

“What’s something you’re excited about?”

“Who are you needing to meet?”

“Who else should I meet?”




All right. I’m excited about this. It’s been a while since we’ve done a deep dive where it’s just you and me talking, so I’m excited about this. 

I’ll tell you what, the topic for this particular episode came from one of my coaching clients. He’s a newer entrepreneur doing some really cool stuff, really trying to grow his business in different ways. He’s got something that he’s growing that I believe is going to be global, but he is new to his area, really kind of trying to establish himself.

He’s trying to establish his brand. He came to me, and one of the things we were talking about was how do you do that? How do you grow your network? How do you grow your connections? It really led to an interesting conversation and a memory, maybe an insight, that I’ve realized is at the core of my business, but sometimes don’t you need to just have conversations that help to draw out some of that stuff out?

It’s like those core beliefs that are always around you. You’re living by them, but maybe you don’t always recognize that, right, until you have a conversation or somebody asks you a question.

Well, that was definitely the case, and one of the things we started to dig into is this strategy that has really been foundational for me as an entrepreneur, but it’s also been really important over the last almost two decades, it’s crazy to think about, for growing my business, but also more so, maybe more so, growing rich relationships in my life.

Because I believe it’s important to have a good, solid network. It’s good to know people. It’s good to be connected, all of those things. If you’re just doing that for networking’s sake, that’s pretty gross. Do you know what I mean? 

I’m an introvert, so there’s going to be a lot of biases that I share with you that might just totally be biased towards the introvert, but I can tell you, it’s one of those having a bunch of relationships where I kind of know one or a few things about a lot of people, but not have any rich relationships.

It doesn’t sound all that satisfying to me. Plus, I look back on how my business got started and kind of where it is now, and I’ve realized, one of the ways that I’ve grown what I’m wildly blessed to say is a business that I love is really trying to provide value.

Meeting people, connecting with people, and providing value where I thought maybe my skill set, the things that I do, could really help somebody out.

When I look back, and also when I look back on my own business, but also on all of the businesses and people that I’ve been able to work with and coach and all of those things, I’ve just realized that rich relationships are at the core of so many people’s success, success in their work, in their careers, but also in their life.

As I was talking to this newer entrepreneur and we were talking about building a global brand, I said one of the most important things, one of the best ways to build a global brand is to not forget about local.


“One of the best ways to build a global brand is to make sure that you have a local foundation.” 


We’re going to talk about a strategy that you can utilize, whether you’re trying to grow a global brand or a business, or you’re just trying to have an amazing career, trying to live more of the life you were put on the planet to live. 

That’s part of our goal is to get people to dream bigger, think better, and do more of what they were put on the planet to do.

If that’s entrepreneurial for you, awesome. If that’s within an organization, a corporation, a nonprofit, fantastic. I just want you to do whatever it is that you’re called to do and do more of it.

One of the best ways to do that and one of the best ways to have a rich and fulfilling and successful career, no matter whether it’s your own business or whether it’s an organization that you work for, is to have deep, rich relationships, to have an incredible connection, an incredible network of people who know you and who you know.

I started to think back on that and that realization and I realized I used one key strategy at the beginning of my business, and it was kind of out of necessity, kind of out of need, almost out of fear.

I realized it was so powerful, it was so helpful, and it’s something that I do in different ways today. I wanted to share that strategy with you because I believe that it can help you to really grow that network of real rich connections.

Again, whether you’re trying to build something globally or just locally, I think it’s always good to start and to have a local foundation, no matter what you’re trying to do, no matter where you’re at in the world.

Here’s what, I’m going to walk you through this strategy, and it’s a series of one-on-one meetings. I’ll give you a little backstory on it first, why I needed it, why I started doing it, and more specifically how I did it, and in some ways how I do it still today.

Basically, the story is that when I was first starting my business as a coach and a speaker, creating online content, all of those things, before those things even existed, I had this idea of creating that.

I wasn’t even sure what it would be, but I had this idea of creating that. I had to build it on the side. We’ve talked about this before. I was working in the pharmaceutical industry, which had been a great fit when I started and slowly had become a very bad fit.

I was in a good job, but it was a really bad fit for me, and every day I went to that job, it was kind of killing my soul. I would have loved to just quit and followed my dreams, but we were living that sitcom life, the single income, two children, oppressive mortgage life, and so I couldn’t do that.

I needed to build this business on the side. Now, one of the challenges that I was up against as well was that I had kind of a limited amount of time to work on my business, this side project, this side hustle.

It was also one of the other challenges that were kind of stacked against me was that as we were launching this, we had actually made a move. My wife and I met in college.

How are you doing? The University of Northern Iowa, right? Then we went and after we graduated, we went and lived in Montana for a number of years. Then we went and I got promoted, and we worked in Chicago, lived in Chicago for a while, and then decided to move back to Iowa, partly to get closer to family part, partly to get ready to launch my business and all those things.

As we did, I switched companies, and we moved back to a part of Iowa, even though I had grown up in Iowa, we moved back to the state, but we moved to a city that I’d never lived in, an area where I’d never lived. I was working for a new company, and I was living in a new area that I’d never lived in before. I felt like I knew no one.

That’s really challenging at any time in your life, But especially as I had eyes on building a business and kind of in some ways also be seen in a new way.

Here I was. I had been a pharmaceutical rep, I had been in pharmaceutical training, corporate training, all those things. Now is back out in the field again. There were people in Iowa that knew of me.

That was my home state, but I was now living 60 miles from where I grew up. No one knew me in that area, all those things. I really had a challenge, and I could have looked at it and I did kind of look at it as an opportunity as well because starting with a clean slate, which was great.

That can kind of also feel like you’re kind of against the eight balls as far as or behind, right like I felt behind, and I hadn’t even started. That’s a brutal feeling. I started to think, “You know what, I need to start to grow my network.

I need to start to grow some relationships in this area.” What I needed to do was I needed a strategy for doing that because I had the challenge of a new job, a new town. No one knew me.

I also had a really kind of erratic schedule. I was a sales rep in the pharmaceutical industry, so it was selling drugs legally in the drunk of my car or the trunk of my car, so a bad joke.

It’s true. I was all over the state of Iowa as well, so my schedule was kind of all over the place. What I needed to do was, first in this strategy was one, I needed to acknowledge that I wanted and needed some new relationships, a new network to grow my connections.

That was the first step is to acknowledge it. The second step was to start to figure out a system. The first step in that system for me was to figure out when could I, how could I consistently start to meet with people?

Because I was traveling all the time, it was really difficult to have kind of a normal schedule to do some of the normal “networking” type activities that a lot of people suggested. Go to networking meetings, go to meetups, all those kinds of things.

My schedule was so crazy that it really didn’t allow for that. Plus, I am an introvert as we’ve talked about on many episodes. The whole thought of just running around in different types of events where I didn’t know a whole room of people was just not all that appealing.

It was like, you know what, maybe someday and maybe that could be part of my system in the future, but for right now, I’ve got to figure out a way to make this sustainable.

One of the things I figured out was for the most part, on most weeks, I was home on Fridays, even though I was traveling a lot for my job, I was home on Fridays.

I realized you know what, I could probably meet with someone at seven o’clock on Friday mornings on a pretty consistent basis, and so that was my window. I started to realize I was going to be able to hit that window consistently, most consistently.

That was my next step was to kind of figure out that window where I could start to use this strategy on a consistent basis. I figured out I needed the strategy, figured out a window of time that it would work for me on a relatively consistent basis.

The next thing I thought of, the next thing I did was to figure out just five people, five people, not a hundred. Now some of you might already know a bunch of people or a hundred people might come to mind, and that’s great.

For me, I really didn’t know that many people. I decided on five people, and my goal was to just start to meet interesting people. Now obviously, I was a business person, I was a coach, a speaker, all those kinds of things.

I did want to sell and promote my services, but I realized this networking, this connecting wasn’t necessarily the first goal of this was not to sell anyone. Now, if selling came as a result of it, fruit on the backend of it, that’s great.

I was not going in with that intention or being my primary goal. My primary goal was to truly connect with interesting people, to learn from interesting people, to help interesting people.

Because I started to think, “If I get to know a number of interesting people and can serve them in some way or capacity, then there’s a very good chance that I’ll learn a lot, grow a great network, and who knows, maybe help to eventually really promote my business and what I’m doing, but at the very least to get to know a bunch of people and maybe even be seen as a value and an interesting person to them.”

I started with five. I didn’t have a list of a hundred, didn’t have a list of 20. You might. I would suggest though, putting together a list of people. If you want to pursue something like this, put a list of people together. 

I know for me, it was the goal of just saying, 


“Who are five interesting people I’d like to get to know better?”

That was my list.

I put five together, and then I sent out an email. 

I said, “Hey, here’s what I’m doing. I am relatively new to the area, and I want to grow my relationships. I want to grow, and I want to get to know some interesting people. You’re on my radar as an interesting person, and I would love to meet with you on a Friday morning at seven o’clock. I’m going to try to do this. It’s my window to meet interesting people.”

I let them know the specific place that I wanted to try to meet at. It was seven o’clock on Friday mornings. I even expressed my goal, and my goal was to just meet interesting people to learn from them and to help in any way possible. 

I was clear, “If you want to talk about what I do, that’s great, but that is not my goal with this. My goal is just to get to know some interesting people and see if I can help in some way.”

In full disclosure, I sent five of those emails out. 

Two people.  That’s right… TWO of the five got back to me.  Those aren’t the best results. I was hoping for five out of five, but initially, only two of the five responded. 

That was a start.

They were like, “Sure, that sounds interesting.” 

One of the people I knew, and one of the people I didn’t.  

Both were intrigued, I think, especially because they knew I wasn’t just trying to sell them on something and so they bit, and so we set it up. 

Seven o’clock Friday morning, I picked a Panera. I picked a Panera close to my house. I don’t know if you have Panera where you live. Panera’s all over the United States now. For me, it was Panera because it was close to my house, and it was also close to the first doctor’s office that I needed to go to on most Fridays.

That really allowed me to still do a good job, be a good pharmaceutical representative, salesperson, all those kinds of things that I was trying to do, and trying to honor my position. I could be at that by 8:15. 


I even told them about that in the email.


 “Listen I’ll need to leave by eight o’clock so I’m really just looking for an hour, 

but I just have this goal of meeting interesting people, 

and if I can help you out, I will.”


I can remember the first meeting. 

Maybe you can identify with me here. I had set this goal of meeting interesting people, and I hadn’t really thought about it a whole lot, but I remember being on the verge of meeting that first person. 

All of a sudden I kind of got hit with fear because I had this realization or this little voice in my head saying, “Who do you think you are? You’re wanting to meet interesting people but you’re not interesting.”




Maybe you’ve had that. If you want to call it imposter syndrome, we can call it imposter syndrome. 

We’ve talked a little bit about impostor syndrome on Dream Think Do in the past,.  That voice that says, “Who are you to do this? Who do you think you are to do this?” 

Maybe you don’t deal with this. Maybe you’re healthier than I am, but I’ve had those voices. 

I can tell you I got nailed by those voices going into this first meeting or getting ready for this first meeting.  It’s like, “Oh gosh, here I’ve called this meeting. I’ve invited this person because I thought they were an interesting person.” It’s like, “Wait, am I an interesting person?” 




Then some of the most important words of advice that I’ve ever received, I’m going to share them with you. I’ve shared them with you or share these with you on other Dream think Do episodes, but seriously, these ring true for me. I probably call on these words about every day.

Here I was wrestling with am I an interesting person, and these words of advice from one of my true mentors growing up, Marty Doane, the owner of the bike shop that I worked at from 13 on, all through my teens, all through high school into college. 

Marty Doane once told me, 


“Don’t worry about being interesting, focus on being interested.” 

How about that? 

“Don’t worry about being interesting, focus on being interested.”

Then of course, after a pregnant pause, he followed up with, 


“If you are truly interested, you will be the most interesting person in the room.” 

I needed that. I shifted my focus.  I was no longer going to try to be interesting. I wasn’t going to try to be charismatic. I’m just going to be genuinely interested. I’m going to ask some questions and really take notes. I’m going to be intrigued. I’m going to be curious.

That was my mantra as I went into that first meeting and all of those Friday morning meetings following was don’t focus on being interesting, focus on being interested. As I did… it was absolutely amazing. 

Here’s the thing, as I started to ask similar questions each time.  I want to share some of these questions with you because if you want a strategy like this, I’d love for you to take these questions and make them your own.

I did a little setup. I would say, “Hey, you know what I’m really trying to do.”  I’d even call myself out saying, “Hey, it might sound weird, but I’m relatively new to this area, and I really do want to meet interesting people.

I want to learn from interesting people.  I’m going to try to learn from people from different backgrounds, different industries, all of that. I want to learn from you. I want to learn from you.” 

One of the first things I would ask them is, “Tell me something I should know about you.” 

I would even sometimes even put a little spin on it saying, “Hey, if it’s something everybody knows, great, but if it’s something you want to share that nobody knows, I’m open to that too.” Like, “What should I know about you?”

It’s funny.  Almost every time people would look at me and pause.  They’d really wait to see. They would actually look and say, “Wait, are you just asking or are you really interested?” 

I would just wait. I’d let the silence work.  Sometimes a smile would start to emerge, and then they’d share something and then maybe share something else. It was really fascinating. 

Then I’d say, “What’s something that you’re working on? What’s something you’re excited about?” 

I wouldn’t necessarily put a caveat to it.

I wouldn’t specify whether I was talking about work or outside work.   Sometimes they’d gravitate towards a big work project, something they’re focusing on with their career or their business. Other people would start to tell me about a hobby, maybe something new that they’re started on. 

Sometimes I’d even put a twist on it saying, “What’s something you’re working on, or what’s something you’d love to work on?”

Oh man, that’s when we start to kind of get into some of their dreams and goals, and sometimes I’d hear about a business they wanted to start or a nonprofit they’d like to launch, or a hobby, a dance class, an art class, cooking class, whatever it is. 

It’s funny because people would almost look around sometimes when I’d ask that like, “Okay, yeah, all right, I’ll share it with you.” 

It was fascinating.

Then another question I’d love to ask is, “Who do you need to meet?” 

It’s funny because especially initially, especially in my first few Friday morning meetings, here I was asking them who they need to meet, and really the only value that I could even potentially offer was encouragement, maybe just even getting them to verbalize it. That was valuable.

At the time, I certainly didn’t have connections to offer. 

I might have a book to suggest if they’re working on trying to learn something, that kind of thing. I might have a resource to point to, but I certainly didn’t have people. I didn’t have contacts.  

BUT… once I was about 10 weeks into this thing, all of a sudden it was amazing how often I’d be like, “Oh my gosh, you’re working on that. I just met with somebody that’s working on something similar, or they’re needing somebody like you. Let me check with them and see if it’d be okay if I introduce you because I think it could be a really good connection.”

NOTE: We should probably do a separate Dream Think Do episode just about how I introduce people, how I suggest introducing people. If you’d be interested in that, leave a comment. I’ll do that, walk you through exactly how I introduce people. 

Initially, I certainly wasn’t a connector, but within about eight to 10 of these meetings, I could not, not be a connector because it was incredible.

I was bouncing around, meeting different people in different industries. 

One week, I literally would meet a plumber with a really interesting story and then an entrepreneur and then a teacher and then someone from a local nonprofit. 

I met all sorts of different kinds of people. It was fascinating. Again, my purpose was to just truly meet a group of interesting people and to grow my network and fill it with interesting people and see where I could help out.

With these meetings, my goal was not to sell them on coaching or have me come in and do training as a speaker or those kinds of things. BUT although that wasn’t my intent… when I look back… some of my favorite clients came out of these meetings.  Not because I was trying to sell anyone… but because I was legitimately trying to help them.

I knew that couldn’t be the goal because if that was the goal for me, people would smell it. 

Also, if that had been my main intent, I wouldn’t be able to sustain it. I knew I wouldn’t be able to sustain it if this was just a big setup for a sales pitch. If I was truly providing value and they truly had a need, oftentimes it was amazing.

We would wind up connecting, or what happened more often than not was they would hear more about my coaching and they would actually introduce me to people who needed me as a coach, and it became really powerful. 

I would say that that was some great fruit that came from it.  But the richest fruit was the rich relationships that came from it. 

I can say that some of those people that I met in that first year of Friday morning meetings… many turned into great friendships.  People I look to for advice, wisdom, and encouragement.

Also, there are people that I look to in many ways that actually, I’ve been able to work with and collaborate with. It’s absolutely been incredible. 

Now, I want to come back to this because I want to give you one last question that made all the difference because like I said when I first started this, I just had those five names and only two yeses. 

I had to do it differently if I was going to ever move past these first two meetings, and one of the things started to produce amazing results.  It was a simple question.

It was: 

“Who else should I be meeting with?” 


I would always say, “Birds of a feather flock together. You’re amazing. I love your story. I love what you’re doing. I love your heart. I love your perspective. Who else should I meet with?”


Nine times out of 10, people would be like, “Oh my gosh, you’ve got to meet _________. You’ve got to meet my friend. You got to meet my brother. You got to meet my business partner. You got to meet____________.” 

What’s interesting is those first two yeses turned into a year of Friday morning meetings.

Friday morning meetings that changed my world. 

I’m wildly blessed to say it’s a global business now.  In fact, this morning I worked with one of my coaching clients and she lives in Hong Kong.  I’ve got coaching clients all over the world and all over the United States. I’m wildly blessed to say that. 

If that’s something you want to do too, that is fantastic. 

I totally encourage you to do that. 


“As you do go global… don’t forget to also think local.”


It’s so important to have those deep, real relationships, right where you are.  To actually share a coffee or a beer with somebody over a table. To be in the same room.  To be in the same space as them. 

Sure, you can still do some of these strategies virtually. You can use Zoom, you can use all sorts of different conferencing and those kinds of things. I encourage you to do that.

That’s how I work with my coaching clients, over the phone, over Zoom, for example.

But I still encourage you to do a strategy like this.  Be intentional about reaching out, getting to know some interesting people, not necessarily with the goal of selling someone on your services or getting a job with a company they work for.

That might be the fruit of that, those meetings eventually… but start with the goal of building some rich deep relationships, providing value, and making the world a better place.

Think about this, whether you do it once a month or once a week, if you started right now, 12 months from now… you would have 12  to 50 rich experiences. 

I’ll be the first one to say that not all of them will turn into fast friends and lifetime relationships, but you’ll have incredible conversations, and maybe you’ll even be able to help a few. 

Maybe you’ll be able to connect a few.

Maybe they’ll be able to help you as well. 

Give it a try. See what you think.  Experiment with it.  

I want to hear from YOU!  Let me know how it goes.  

What questions do you like to ask?

What time of day do you try to meet?

Do you prefer to meet over coffee… tea… beer… or something else?

Comment below and let me know.


Quick Episode Summary:

  • 0.02 What to expect today
  • 3:37 The importance of rich relationships
  • 6:18 When Mitch worked a job he hated
  • 10:55 Pressuring interesting people
  • 16:30 Becoming interested
  • 19:43 Who do you need to meet?
  • 24:48 Don’t forget about local relationships


Listen to Mitch Mattews Top Podcast here

1 Comment
  • Cardiff Hall
    Posted at 20:40h, 09 February Reply

    Fantastic Episode Mitch! I love this idea and will be implementing as I recently moved to a new city. Who doesn’t want to be included as 50 Most interesting people when you reach out!

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