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23 min

“Everyone Thinks I’m An Extrovert!”

4 min read
 | Jan 12, 2018
  1. Home
  2. Introvert
  3. “Everyone Thinks I’m An Extrovert!”

Can the shiest, quietest introvert really learn to fool them all?


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Jaime Masters is the host of Eventual Millionaire, listed by INC as a Top-3 podcast for business owners. She’s also an incredible public speaker, a master networker, a flawless interviewer and moderator – and an introvert.

We’d been good friends for over a year when we decided to attend a networking event together. I could see as soon as we got there that Jaime knew everyone, and we split up to each do our own thing. I didn’t know anyone, but I followed my usual networking tactics and ended up chatting with some of the most important people in the room, including Ryan Deiss, the founder and CEO of Digital Marketer, who mentioned that he was an introvert.

Later, when Jaime and I got in the car to go home, I told her how surprised I was to keep meeting these incredibly successful people, who seemed so comfortable and natural in any setting, and learn that they were introverts like me.

That’s when she said it: “Matt, you know I’m an introvert too, right?”

This blew my mind. If you’ve heard Jaime present, moderate, or interview, or had the good fortune to see her networking skills in action, you’ll know why I was so surprised. She seems more extroverted than most of the true extroverts I know! The skills and strategies she has mastered over the years make it easy for her to beat extroverts at their own game, and in fact, put her in a league of her own.

It takes a lot of work to seem like an extrovert

Let’s get one thing straight: introversion is something to be embraced, not overcome. You already have every talent and ability you need in order to come across as confident and outgoing. You just need to learn the systems and strategies to hone your inherent skills and translate them to business success.

It wasn’t always so easy for Jaime to walk into a room and command it, to interview millionaires without skipping a beat, to speak and moderate panels with finesse and charm. In the beginning, there were tears, anxieties, failures, and questions of self-worth. But with a strong mentor, the right tools, and goals that she was determined to achieve, Jaime made it happen.

And you can too.

Some Questions I Ask:

  • Can you tell us a little bit about your journey, and how you got where you are today? (1:32)
  • Was there ever a time you completely bombed out while trying to build your business? (4:08)
  • What are some of the strategies you learned in order to not only be comfortable with networking, but to actually enjoy it? (8:37)
  • How did you land your first millionaire interview? (11:43)
  • What are some of the strategies you use in being such an effective and natural public speaker? (15:26)
  • Do you still hate public speaking today? (18:04)

In This Episode, You’ll Learn:

  • How Jaime went from a shy, artistic, self-professed computer geek to the host of a Top-3 podcast for entrepreneurs (1:38)
  • Why the concept of sales as “selling yourself” was especially hard for her (2:43)
  • How having an amazing mentor helped Jaime push herself (4:16)
  • How Jaime overcame and learned from her first, awful networking event – and how she feels about networking today (5:30)
  • How Jaime built her network from knowing no one in the middle-of-nowhere Maine to a roster of millionaires and influencers (8:57)
  • What “connection threads” are, and how they grow your network (9:35)
  • How being determined and resourceful can make or break your dream (11:57)
  • The major barrier Jamie faced in public speaking, and how she overcame it (16:05)
  • Why Jaime, an introvert, loves public speaking (18:14)

Resources Mentioned in the Show:

Thanks for taking the time to listen!


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Matt: Hello everyone and welcome back to The Introvert’s Edge. I’m ecstatic to introduce a really good friend of mine, Jaime Masters, who is the host of The Eventual Millionaire where she actually interviewed over 400 millionaires. I don’t know how she got access to 400 millionaires – maybe she’ll tell us – and yes she actually is an introvert and she’s actually managed to translate all the strategies she’s learned off a lot of these millionaires, a lot of them introverted millionaires. And translated that into what she does now, which is her business coaching. So Jaime thank you so much for coming on the show.

Jaime: Thanks so much for having me, I appreciate it.

Matt: I’m really excited about sharing your story because I had no clue. We’ve been friends for a long time and I had no clue. Maybe that’s why we get along so well, I had no clue that you were an introvert. We were having a conversation about some of these other unusual introverts that I’ve got on the show and you’re like, “Matt, you know I’m an introvert, right?” And I just had no idea and I think that you’ve got so many great strategies for how you get perceived as this outgoing person, I’m really looking forward to delving into that. But first I’d love to start by just hearing a little bit about your journey and how you got to be where you are today.

Jaime: So to go back though, I personally thought I would be an artist. So growing up I was voted “most artistic” and I was literally in the corner reading books. So when I started out on my own and starting my own business I didn’t realize how much you had to interact with other people, because I was a computer geek after that. So when I actually stepped into the world I had no idea what I was getting into.

So my story goes, I paid off $70,000 in debt and started my own business when my son was born, and that was really tough. I don’t want to go back too far because we don’t have a lot of time, but I had a 6-figure job at 22, 24 and hated it. That’s why I ended up paying off all the debt and trying to get my own thing. I didn’t realize how hard it was starting your own business because of this.

So being this girl, reading books by myself in the corner and realizing the only way you make money in business is you have to sell something, which means you have to talk to people, was really difficult for me just because I wasn’t very good at it. I mean people liked me, but it wasn’t natural. Does that make sense?

Matt: Yeah, definitely. The first time you actually had to sell you.

Jaime: Yes, that was the biggest problem, right? Because it wasn’t, “I have this nice produse, you should buy it, that’s awesome”, and we’re directing the attention over here. It’s like, “I’m a business coach”. I had a mentor – thank goodness – that made me cold call and do all the crappy stuff that I wouldn’t have done on my own without him for sure. But it was so uncomfortable. See, I turn bright red also, so whenever I’d speak to anyone I’d literally look like I had hives coming out my face. Because you know, that’s normal. And getting over that – I mean, I can’t get rid of it – so getting over the feeling of as it’s coming up. You heard me stutter a little bit before. It’s like, “Ok, we’re getting into it, it’s fine.” But I’ve just done it for so long and learned – like we were talking about before – the hard way to get past this. I’ve thankfully come a long way. And you thought I was an extrovert so apparently it’s working.

Matt: I think what’s really interesting with you though is you didn’t naturally have that ability, you didn’t know that it was a learnable skill, you just kept slogging at it. I mean I know that you came back from debt and you had 2 kids and a lot of introverts, when your back is against the wall, you try to find solutions. But you could have quite easily gone, “I can’t do this.” And I think a lot of introverts kind of avoid that. But I’m looking at you now and as I said, the whole time I’ve known you I thought you were extroverted. So I want to be able to believe you a little bit so why don’t you tell me, tell me a story, did you ever go out and just bomb out when you first started?

Jaime: Yeah, good, I love these stories too. Bringing up the mad past, awesome. So if I didn’t have my mentor, so I tried it on my own but I would avoid it. So especially when you’re getting into coaching – I wasn’t a business coach at the beginning – I was a coach and I thought coaches were stupid also. So head junk goes around. I wanted to help people, but not believing in myself anyway, made it ridiculously hard to even talk about it.

At the beginning – this is why I’d just work on my website and not go talk to anyone – I didn’t make any sales, who knew. My mentor, when I actually had him, he pushed me to do it no matter what anyway, because I really wanted to do a good job. That’s pretty much the only reason why I didn’t go back to a corporate job, to tell you the truth, I swear. He made me cold call and I had hates sales beforehand. I tried being a Kirby vacuum cleaner salesperson when I was broke and I thought sales was horrible. I would never be one of those people ever. And he tried to show me a better way of doing it.   

I didn’t realize it was literally like banging your head against the wall the whole time. So cold calling, people would hang up on me. I would literally almost cry. Because I wanted everyone to like me also, and that was one of those things where I’m like, “No, I’m really a good person”. But my worst one was my first networking event and there was like 400 people and I’m in the middle of nowhere in Maine – so there’s not a lot of networking events – and I think the Governor was at this one so it was really big and I had just gotten my business cards.  

Matt: So a real business now.

Jaime: That’s what they do, you’re supposed to have business cards. I don’t have any now. But that was one of those things where I get there and I see a sea of people and they all knew each other and I literally knew no one and I’m shaking and turning bright red.

So I sit down because I didn’t know what else to do with myself. Someone sits next to me and I did not stop talking to them because I knew that if they leave I still look awkward by myself sitting there. I literally followed him around. I was supposed to, my mentor gave me all these things, go talk to 10 people, get some sales calls. It felt so awkward and horrible. I remember going back in my car and being like, I never want to do that again. I got visibly anxious anytime I thought about going back to a networking event, which is crazy because people don’t see how far I’ve come.

You thought I was an extrovert, but I rock networking events. I know I can talk to the people that are introverts that are on their phone and doing this same thing and they’re like, “Yay, somebody is talking to me.” And you can actually make connections and I’ve used a bunch of this stuff that’s in my book that we agree on x10, even though we had to learn the hard way, of tactics that make it so much easier. So that way you don’t feel like an idiot even when you’re bright red and crazy. So if I can do it, you can do it too.  

Matt: That’s an amazing transition for you. I mean, a lot of people think these things just aren’t possible for introverts. I’ve seen you in your element doing it and I thought it was a natural ability. And we talk about it all the time, the stigma that introverts have where we see anyone else that’s successful and go, “That person would have to be an extrovert”, because they’re natural at it. And I projected that on you and it’s what we do, and it’s what we have to stop doing.

But I’ve seen you go out and network and we actually went to a networking event recently together and we both kind of had a dialog about our strategies because you have a very significant strategy and I have a very structured strategy and we both went off and just ran our programs pretty much. And you actually commented afterwards you were like, “Matt, usually when I go to a networking event with people”, let’s be honest, you now pretty much know everybody, every time I have a conversation with you you’re like “This person and this person and this person”, and I’m like overwhelmed by the number of names of these people that you know. But you weren’t always that way and these strategies got you there.

So you ran the program and I did and you and I walked in together and then we both separated and we both worked the room. You sort of explained to me afterwards that most people now, because you are Jaime Masters, is that people kind of just hang to you and won’t leave you alone. So I’d love for you to share some of the strategies that you used and what you’ve implemented to go from where you were to where you are now.

Jaime: Definitely, especially the whole billionaire thing. Everyone is how the heck did you. I grew up in the middle of nowhere in Maine, I literally had no millionaire anybody anywhere even close to me. So building a network of that, number one, and being able to have, I mean my network is insane. And my goal at the beginning, and I think introverts in general are good at deep friendships. So I’d be funny and joking with my friends and then I’d go out in the real world and be awkward and crazy, and I tried to learn how to pull some of those pieces and let my personality show through a little bit more and hopefully not care what the consequences, some people look at you a little crazy.

But some of the tactics that I’ve learned is just trying to make them feel comfortable, like we were talking about before. I touch people, it’s easier for a female to than it is for a dude. I hug people. It’s one of those things where you can start making them feel more connected. I call them ‘connection threads’, so the more connection threads I can get when we talk to somebody at the beginning, you can build a rope. If you have a whole bunch of threads you can have an actual relationship. So when I go to events I’ll bring clients of mine and I’ll do all the introductions and I will try and make them feel as comfortable, I will bring connection threads for them to help facilitate. It’s really tough for most people, but at the beginning it was me going, “I just want to be your friend”, literally.

The millionaires I talked to I just kept trying to find those connection points that made a big difference so I felt like we could actually become more than just “networking” strategic partners. I literally just had no friends in the middle of nowhere in Maine and therefore needed to make friends. And this is how I had to do it.

Matt: So you were just willing to do the hard yards and put in the effort. It sounds like you learned through the school of hard knocks and just learned the process. But you didn’t say, “It’s not possible for me to do it.” It’s how do I find the strategy, what works for me.

You and I have talked about the differences in our strategy so for me I will touch people on the shoulder, guys on the shoulder. I don’t do it to women for obvious reasons, but we have different strategies. I tend to find one person and go to an effort of giving them value so that I attract a lot of people to me. You look for introverts in the room and you go to them and you make them feel like they’re part of the party.

So we all have these different little elements of what we provide. I’m really interested though, the millionaires that you reached out to, so it’s really hard to reach out to a millionaire. At least that’s what a lot of people think. While I’ve had a lot of really good friends like yourself on this show, some of the people I’ve never met before I just reached out to them because I knew they were an introvert and I wanted to. I had Chris who is recording this session say, “How did you get him? You said on the show that you never met him before. How did you get him on the show?” And my response was, “I asked.” And that’s the thing, for introverts we’re, “I can’t reach out to that person because if I do they’re just going to say ‘no’ to me, why would they say ‘yes’?”

Well a lot of millionaires said ‘yes’ to you so I’d love for you to just talk through how you started and when it started getting easier.

Jaime: That’s a great question. So that mentor that I had beforehand, I asked him, because he sold a million dollar business and I thought oh maybe he…oh nevermind, half of that was taxes. So I asked him if he knew anyone and he said, “Not anyone that’s going to come on your show and say it.” And I’m like, “Oh, awesome, thanks.” Great, where the heck am I going to find – again – in the middle of nowhere Maine. I literally went on iTunes and looked for somebody else, I just looked up the word “millionaire” and tried to see if I could find anyone else that said that they were a millionaire and were willing to go on a podcast. I asked, I emailed him and I did not know him at all, his name was Frank McKinney, the worst interview in the world. He came back on my show so many times after, thank goodness, but I like, it was the worst ever.

But he had said ‘yes’ and I was like, “He said yes!” It was an email. It’s so funny how it shouldn’t be that big of a deal, who cares if they open it, who cares if not, but it’s such a thing. I remember when I first sent it I was like “send” like that and made myself do it. That was the very very first one, and I got a couple more that way a little bit easier.

But as it started going I ended up using “Help a Reporter Out”, have you ever heard of that?

Matt: I have, yeah.

Jaime: So Peter Shankman who started it way back when, it was so easy, there were millionaires coming to me for that. Now as soon as I got past that – because I literally did not think I was going to get any – so I started doing one a month at the beginning because I was like well if I can find twelve I can do this for a year, and we’ll see how well this goes.

But what’s crazy is because they’re so well networked once I started actually making friends with some of them they were like, “Oh, I know somebody”. We only get referrals. Literally – my assistant is over there – she knows we’re back to back til December right now, six months in advance. Almost a year schedule all rearing and ready to go. How amazing. I’m not the “millionaire girl” and everyone is like, “I know a millionaire, I should introduce you.” Best networking tactic in the world.

But if I stopped after the first 12 to 20, I don’t think it would have gone nearly as far as it is now. Now I’m used to it, I don’t suck so bad at interviews. The first 20 or 30 sucked really bad, I’m surprised anyone listened to it. But after 400 it’s gotten way better. But the network has grown insanely just form that.

Matt: Well I see millionaires almost fall over themselves to be on your show. Now you have a waiting list, you’re like, “Well it’s not just that you’re a millionaire, you kind of have to be entertaining and have something to say.”  

Jaime: I do. I’m like the luckiest person ever.

Matt: I think that came from you being very strategic about saying here is what I want, now I’m going to go and get it. It’s like book endorsements. When The Introvert’s Edge came out that was like I’m going to go out and get endorsements for the book. Everyone starts thinking about the network of people that they know. And in my mind I was like, well those people like me anyway, while I’m going to get some of those it makes more sense to get endorsements from people I don’t know because no one is going to endorse a book without at least reading part of it.

So I then started reaching out to people that I have never met and say, “Hey I’ve got a book”, and everyone was like, “You’re never going to be able to get people to endorse your book that way.” Seriously I sent a LinkedIn connection request saying, “I’m a big fan”, that was all it said, and they would then accept my connection.  That was it. Then I would respond and they’d say, “Thanks very much”, or some people didn’t even respond they just accepted. And I would then send them, “Hey, sorry to reach out to you on the blue, I’ve got this new book being published, is this still your correct email address?” You can get that off LinkedIn.

Jaime: That is brilliant. That is brilliant.

Matt: But then I just got all these ridiculous level endorsements from people who I now have a relationship with because I asked. And I think that’s what introverts don’t do, we don’t ask.

So I think we covered the networking element. What are some of the other barriers that you kind of faced when you were going into it? Because you now speak on stages and you’re so natural. We just had you speak at Small Business Festival, the conference that I run, and you ran this panel and I remember watching it while I was running between mad dashes between dealing with things and thinking, “God, one day I want to be that natural when I’m just leading a conversation.” How do you do that?

Jaime: So at the beginning I actually did Toastmasters. Because I would turn so red and then I would get really flustered and I would get stuck in my head and I wouldn’t be able to get past it. And so I joined Toastmasters and one of the first things they did for one of my first speeches is – this is sad also, it’s bringing up such horrible memories.

Matt: I did warn you about this show, right?

Jaime: So because I turn red and I wore a tanktop so you could see it goes all the way down my arms and they go in the comments, “You should wear a turtleneck and long sleeves next time, it was very distracting.” I really thought about never speaking again on stage because that’s a huge barrier that I can’t. It’s not like I keep learning and just getting better and knowing what to say or practicing a speech over and over again. I literally look like I’m coming down with hives and people get distracted because of that, and getting over that piece at Toastmasters I just kept going and going and going.

At the beginning they told me the tactic of just tell people about it. So at the beginning I said, “Hey I turn bright red, just so everybody knows.”  And the more I do it it still happens, it still happens on my show and stuff like that and now it’s just a natural thing that who the heck cares, the fact that I got through it and past it, I can use it as a story of how horrible it was at the beginning and if I can do this than you can, too.

Matt: Well people don’t want to get a coach that’s perfect to coach them.

Jaime: I’m close to perfect.

Matt: Well maybe now you are but when you were learning they want to know that you had imperfection, because if you don’t how could you possibly teach them. My speech coach taught me to acknowledge the obvious. Because for me anytime something would happen I would freak out about it and all of a sudden I’d become tongue tied and I had no idea what to say and that was the end of the speech. I would take a few minutes to recover and then I would be able to come back. And he said just acknowledge it likes it’s there, acknowledge it and everybody will have a laugh, and you move on. Like I do with the photo in my speech, I’ve got a photo of me with acne I put it up and I’m like, “I’m going to click that off now because I don’t want that up there during my presentation”, and everybody laughs and we can all move on.

I’ve seen you speak and you’re just so natural and so comfortable. Are you glad that you now get to speak and share that value with the world, or do you still freak out every time that you go up and hate it?

Jaime: No, I love it. I love it, love it, love it. And I’ve learned tactics and techniques that made it a little bit better. The energy that I get – and I used to say this all the time – like, “You guys are actually listening to me,I have small children and they don’t listen. I just like the attention please.” But what you can do as far as impact goes is insane, you can really connect with people, you can really change people’s lives. So the fact that I got over it, thank goodness.

There were so many not good speeches. I started really really small, thank goodness, in Maine with 12 people. But I’ve learned tactics even when I did mess up, I would be like, “Well that was really awkward, wasn’t it?” I’d try and do these little pithy things so that way it wouldn’t feel so, you know when you’re in a room and there’s awkward tension and then it starts going a little bit more and a little bit more, and then you’re like, “Crap!” You have to ease that because if you don’t the audience now doesn’t trust you anymore and they’re like, “Ok, she’s crazy.”

So I learn these little things so that every time it did happen – because it happened quite often because I don’t memorize my speeches very well either – I have little things I’ll do to go on little tangents to make it feel more natural. And then I’ll actually mess up again and then I’d have to use these little tactics again. So it’s literally just tons of repetition of getting up there over and over and over again.

This is what I tell my clients a lot too, imagine if you went ahead and planned on doing a speech every single day for 6 months, you’d be fine. Even at the very beginning there’s still a lot of people that get scared because you never know. But if you know the energy and you just have fun with that energy on the stage, no matter what people are going to take what they think they’re going to take. And sometimes you’re going to have a crappy time and that’s ok too, because even if you affected one of those people you did a great job. And that’s what I started focusing on after the fact, not that I was going to trip walking up to the stage. Because when you think about that right before you do it you’re way more likely to do it, from experience.

Matt: I think that makes a big difference. We had Ryan Deiss on the show as well and he was talking about the exact same thing about he just focuses on he stopped making it about him and he focused on making an impact on people, and as soon as he had that mindset flip everything changed.

There’s a couple of things I want to pick your brain on in regards to this and we’re running out of time for this segment. So we might pick it up afterwards because I’ve seen you moderate panels as well and I actually modeled the way I moderate panels off seeing you do it going, “Crap, the way I do it wasn’t as good as her. I’m going to learn that.” Because as introverts we have to have strategies and we can’t assume we know things and we can’t assume that things are unapproachable. We just have to model someone that does it well and we have to model introverts that do it well. So once I knew you were an introvert I said, “Cool, I can model that person.”

But let’s pick that up in the next session. But thank you very much for joining us today and I really do appreciate you sharing so much of that intimate, awkward story from the past.

Jaime: Great. Thank you so much for bringing it back up again. No, I appreciate it a lot.

Matt: Well it was great to have you and thank you everyone for joining us again today and I look forward to seeing you in the next episode. If you haven’t yet, please make sure that you subscribe, post a review, to make sure that more and more introverts get the opportunity to see this content and start having the opportunity to improve both their business and their life. And if you’re looking for the second episode make sure you go the I look forward to seeing you in the next one, thanks again. Cheers.


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