You’re One Connection Away From Changing Your Life with Scott MacGregor

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0:32Don't wait for a problem to remind you you're uncovered. Policies start as low as$29 a month. Get protected in minutes at nextinsurance.com. That's N-E-X-T insurance.com. People play checkers and they don't play chess. They take one move. They're very transactional. It's like, am I going to win the game? And if it's yes, they're going to do it. If it's no, they won't do it. And relationships are like that. We could have probably never predicted all the things that we would do together and collaborate on. You can't predict that stuff. You're literally one person away and really one conversation away from changing your entire life.

1:20Come on this journey with me. Each week when you join me, we are going to chase down our goals, overcome adversity, and set you up for a better tomorrow. I'm ready for my close-up. Did you know I recently celebrated having created 450 episodes of this podcast? And we are still going strong. Thank you for listening. That is a lot of topics and amazing guests. So I thought I would put together a few of my listener favorites for the month of September as bonuses on Thursdays to help you catch up on what you may have missed. So you can keep growing your confidence with these confidence classics. Let me know what you think.

2:00Meet a different guest each week. Wait a minute to change. Confidence queen. Hi, and welcome back. I'm so excited for you to be back here with us this week. Okay, it's so rare that I have someone on multiple times in the show, but today you are going to be with one of my dearest and best friends, Scott McGregor, who is also an incredible guest. And we are going to get into some major hacks that are going to grow your business for Q4 in 2026. So Scott, thank you so much for being here. Heather, you know, it is an absolute honor. I waited forever to get on the podcast and it was so awesome to be on.

2:40The first time, so to be on twice, like this is epic. Okay, so let me give a little background on Scott because Scott has achieved so much and I just want to dial a little bit of it up for you. So he's founder of the Outlier Project, which if you've never checked it out before, I'm a part of the Outlier Project. It's incredible. It's the best business group that's out there. You've got to check it out. Founder of Outlier Magazine, which is so cool. I love that you've branched out from community to media outlets. It's amazing. Founder and CEO of Something New, four times author of the Standing O series, which is all for charity.

3:17And that just speaks volumes about Scott right there. He's the eight consecutive American Business Awards winner for innovation. That's insane. Best of staffing winner, net promoter score of 94.4%. The staffing industry average is 28%. Oh, my gosh. Winner of sales executive of the year, American Business Awards. Founder magazine, 100 top founders to follow. Contributor to Forbes magazine. It goes on and on and on. There's so many more. Advisory Council, Harvard Business Review. you? I mean, Scott, what haven't you done at this point? Those are all the things that no one will actually care about.

3:55I think the only thing people care about is impact. Like you and I, our friendship, like you've had a major impact on my life. And hopefully I've been able to do the same for you. Like that's what really matters. All the awards, the books, the like, No one cares about the house I live in or the car I drive. People care about the impact I make. So that to me, it doesn't read well, I guess, in a bio, but that's really the thing that people care about. Let me ask you an interesting question that just came to mind that I think could help some of the listeners. Do you think having those accolades is necessary first in order to have impact or to make impact?

4:40Not necessarily, but I think it definitely helps. You know, you can have an impact, maybe not at the scale that you could when you have some additional credibility. But we all can have impact. You know, we all can touch people's lives every single day. I'm very intentional about building relationships with people that have high influence and high access because I know that makes my impact exponential. Like at the end of the day, my ability to do great things in the world is somewhat predicated by the people that I know that I'm friends with. And when those people have a lot of access and influence, the bottom line is your ability to do amazing stuff is very, very different.

5:35All right. Well, let's run it back a little bit and let's talk about how you and I met initially. And I want to share this with everybody because we have a number of real stories I want to share today. They're like pull the curtain back kind of moments so that you're going to get a glimpse into what really goes down behind the scenes. So first of all, I remember I was looking for a way to help get somebody's child into college at NYU. And I just went to LinkedIn. Like everybody should always be going to LinkedIn. I went to LinkedIn and I typed in NYU. And for some reason, you were an adjunct professor or you were supporting the school somehow.

6:10Your profile popped up. And there was something about your profile and your content that I thought, I'm reaching out to this guy and I sent you a DM. have. It wasn't my picture. It was my profile picture. But the irony is this. You responded, right? Here I am a random person that you've never met before. I'm reaching out asking you for help. And you immediately responded and immediately offered to get on a phone call with me to help me out. Why would you do that for someone you don't even know? It goes back to impact. It's like if you can help somebody, if you have the ability to help somebody, you do it.

6:50I've just worked really hard my whole life for a lot of things, for security for my family and for just self-esteem and things like that. But a lot of the reasons why I've done a lot of the things that I do today, the magazine and the community are two good examples. Those are platforms that allow me to do things for other people. And I love, I love doing that. So when you reached out, it was a no brainer to reach back out to you. And then, you know, I just, I remember that initial conversation and it's like, okay, now go down the rabbit hole, like who's Heather Monahan. And although that was before your first book, before your podcast, and I don't know how many followers you had, but you didn't have the hundreds of thousands that you have today.

7:45And I just, but I just remember that conversation. I was like, you were so different. You were somebody that it was like so easy to bet on. And why wouldn't you want to help somebody like that and become friends with somebody like that? So it was, that was an easy, easy decision. I just want to make sure everybody realizes though, So Scott had, I don't even know if I had been fired yet. Maybe I had just been fired. Like there was, I had probably 3 ,000 followers on social media. There was no big brand presence or big win that Heather Monaghan's reaching out to. Can't wait. I'll get on her show or maybe she'll mention me in her book or, you know, there was none of that.

8:24So you showed up and supported somebody who you didn't necessarily have any idea that you would ever gain anything from. And that's really the core, I feel like, of who you are. So, all right. So that happens. cut to no I was fired because I was working on my book now I remember and cut to we start talking about you were working on your first book ironically or to me I believe this is like divine intervention and we were both working on book launches at the same exact time and you ended up inviting me to New York to be a part of your book launch which is really when we became friends in real life and became team us.

9:02But that was, I mean, again, I didn't know what to expect out of anybody. Here you are a person that just supported and helped me that didn't know me. And I wanted to be able to get the chance to support and help you. However, the irony is I go to your event, you have so many celebrities there, you have so many people supporting you there. And it became clear real quick that you were the right person to know you were the connector that would put people together. And, and it was so apparent walking into your event that night, it was like something I'd never seen before. Well, thank you for that.

9:35I mean, I love, I love connecting the dots. Like I think connecting good people with good people and helping people to achieve the things that are important to them is so much fun. So when you do it right, it's great. Like when you make introductions that are disproportionate, like they're beneficial to one person, but not to another, those are things I try very hard to never, ever do. So hopefully, whether it's in those rooms or probably what got people in that room that night was just a whole lot of trying to help people get connected with people that could help them achieve whatever their hope or dream was.

10:23Well, one of the ways I like to share how your gift, your connection ability, your talent that you really refined and put into a framework that works for you constantly, but truly is based in helping others is I remember one day after we had been friends for a few years, I said to you, Hey, I launched the podcast and I said, Hey, I'd really like to get Jesse Itzler on the show. I know that I've seen him in your circle. And you said, Heather, he's going to be really tough to get to. However, I think I could introduce you to his business partner and maybe that connection could take you somewhere.

10:57And that's exactly what you immediately did. And to, you know, back to your framework of the power of connection and how to really take care of people and champion people and work together. Mark and I started speaking that turned into a friendship. Jesse was not available at the time. I'll never forget. I I was out in LA. I was due. I don't remember what I was doing. My podcast was based in LA back then in 2019. And I remember he told me, no, he said he's not going to be able to do it. He's so overcommitted. He just launched this new 2029 thing. He's like, Heather, he just can't. I'm saying no to everything right now for him.

11:34But in the future, if that changes, you know, let's talk. Until then, let's talk about what we're doing. You know, maybe we could get you involved somehow. So he and I kept talking about different events that they had. you know, when I might be in Atlanta, that they had things going on in Atlanta. So we stayed in touch and kept in communication. And then wouldn't you know, one random day he said to me, hey, he's just said that he wants to get on a couple of podcasts because he wants to promote some new initiative that he had. Why don't we make your podcast one of them? It was so good. So, so good.

12:07You know, it's like one thing leads to another and it's everything is connected. And that, you know, turned into the incredible interview you did in Boston with Sarah and Jesse. And that was fun to kind of play a little bit of a role in helping to make that happen. Great. No, pause because you're like glazing over something that cannot be glazed over. Meet a different guest each week. Play it on the team. Confidence creator. If your anxiety, depression, or ADHD are more than a rough patch, you don't need just another meditation app. Talkiatry makes it easy to see a psychiatrist online using your insurance in days.

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15:54During the interview, his internet went out. Do you remember this? Yes, billionaires sometimes lose their internet too. Ironic. And so all of a sudden my phone starts ringing. I pick up and it's Jesse Itzler. And he says, my assistant gave me her number. I'm really embarrassed to say, power went out. What can we do, Heather? I said, I can jump on a plane and come to Atlanta and come to wherever you are and interview you. So he had me to their home, which was so generous of him. I went to their house, interviewed him with this great interview. I left. Everything went well. I sent him a thank you.

16:25He said he liked my microphone. So I sent him the exact same one so he could have one for his house and followed back up with you. Was so grateful. Cut to one day you're speaking to someone in Boston that was having an event in Boston and they're talking about they wanted somebody to interview Sarah and Jesse live on stage. And you said, how about Heather Monaghan? She already knows Jesse. And you took that initiative on my behalf for me. Yeah, so it was hyper growth. So a friend of mine, David Cancel, is the CEO of a company called Drift, which is now a unicorn billion dollar company. And now I think he's the chairman of the board.

17:07But he was putting on hyper growth. and I was like, oh man, I knew Jesse was speaking there. And so I don't know if I told you beforehand or I told you after, but I called David, I call him DC and I go, DC, man, you have to have Heather. And so I told him a little bit about you and then the rest, as they say, is history. But for everyone listening right now, this is what I want you to know. This is the power of getting to that one person, right? Had I never met Scott, I would have never gotten to Jesse Itzler. I'd never gotten to Jesse Itzler. I was never going to end up interviewing Sarah Blakely live on stage in front of thousands of people.

17:48Those moments are business changing, career changing, brand changing, life changing moments for me, 100%. But it all started with that one person of impact, which is you at the center of all of this. And I think too often, people don't think about that. They think about stepping back where they want to go and, you know, this is what they want to achieve. Instead of thinking, what one connection am I possibly away from unlocking these opportunities and a plethora of others that I could not even fathom, which is exactly what's happened as a result of our friendship. How often have you seen things like that in your own life?

18:26I think people play checkers and they don't play chess. What I mean by that is they take one move. They're very transactional. It's like, how is this move going to, am I going to win the game? And if it's yes, they're going to do it. If it's no, they won't do it. And I like to think I'm always playing chess. I'm thinking multiple moves ahead. And, you know, relationships are like that. Like our relationship, we could have probably never predicted all the things that we would do together and collaborate on. You can't predict that stuff. But if you are like-hearted and you're with really good, interesting, smart people, lean into those relationships, build those friendships, because those are the friendships that are going to spawn other friendships.

19:28And you have no idea. I think most of the people that I meet, if I figure out that they're interesting, that they're smart, I'm going to pour into them. I don't try to figure out where it's going to go. I think trying to project that is a waste of time. I just know that I've always wound up in these spots. It's either a conversation or I'm in a room or something's happened for me. And I'm like, how the hell did I get here? And when I reverse engineer it, it's not a straight line. It's a crazy circuitous path that took me there, that there would be no way to predict that going forward. But in retrospect, you're like, my God, I'm so glad that I formed this friendship with you know, whoever, because all these things, this crazy chain of events that happens in our lives all the time would have never happened if it weren't for, you know, that really key relationship.

20:37And you never know who that's going to be or when it's going to happen. But, you know, So that's the magic is you're one person away. I always think from changing your life forever. And I'm not being dramatic. I mean, I think you're literally one person away and really one conversation away from changing your entire life. Play chess when everyone else is playing checkers. It's so well said. And it was so funny. and this is totally behind the scenes and has not materialized yet, but I'm gonna share it because I think it's important for everybody to understand the power of connection and the power of friendships and true relationships.

21:22I had a very good friend, yet again, another friend, another male friend of mine that I've met through LinkedIn, through business in the past decade, who's just been a supporter of mine, another great human, reaches out to me and sends me this note and says, Heather, look at this promo. Patrick, David is running right now. he's looking for a female host. This is you. And so he sends me this promo, which I would have never seen otherwise. So again, someone looking out for me, you know, with not wanting anything in return, I look at the promo and I'm, Oh my gosh, this is me. So I submit myself. I talked to a few people.

21:57They're like, we're going on, we're submitting you and crickets, nothing. And so I'm thinking, this is weird. So I, he follows me on Instagram. So I DM him on Instagram, crickets, nothing. So I'm thinking in the back of my mind for a week, how do I get to him? I need to get to. So I inevitably call you and say, I don't know what to do. I need to get to this guy and he is tough to get to. I'm really struggling to figure it out. And of course you would have a solution for me, Scott, yet you're the one that can see things that I don't even see. Well, that's the fun part. It's like, if you really care about people and obviously I care about you and I care about our friendship, it's fun.

22:36It's like a game. It's like, oh my God, this is important to my friend, Heather, like, how can we solve this problem? And that gets my brain going and it's fun. So, you know, that was me last night, like going down all these different rabbit holes and then trying to figure out like, what could we do? And then stumbled upon some stuff that I'm like, oh, wait a second, there's some connective tissue here that this could potentially lead to the answer. Will it? I have no idea. But it's fun trying to figure that stuff out. And I guess, you know, you need new friends if you don't get lit up by that stuff.

23:22If it feels like a homework assignment, as opposed to like, no, I want to do this. Like I shared with you earlier, there's been portions of the day today where I'm like going down all these little rabbit holes trying to figure out how to make this happen. And, you know, some of them turn into, I can figure out already that they they're going to turn into nothing. And then there's a few that I'm like, okay, nope, this could turn into something. So it's just, uh, it's fun. If you don't want to help your friends out, you need, you need a different friend group. it's so you need you need to start getting into the right circles that are out there and so true so one of the things that Scott found for me which was so helpful was he reached back out and he said you know that Patrick Bet David was on School of Hard Knocks with your friend James Heather and once you said that I said okay you you nailed it I know that I can reach out to James and ask for a favor how do I know that because I did the interview with James and then James came to me and said, well, you do me a favor and come in and teach one of the classes for my community.

24:32It would mean the world to me. Can you do it at eight o 'clock at night on like a Thursday night? You know, it was a pain. And I'm like, of course, I'm happy to support you. So when you lean in the same way Scott leaned into helping me when this young guy raised his hand and said, hey, can you help me? Yeah, of course I will. Then you suddenly have a friendship that is mutually beneficial. you don't ever worry about anything. I had just sent James a speaking engagement the week before from an agent that came to me wanting me to speak about something. I ended up connecting James. I said, this is better fit for James.

25:07And when I found out James was going to be in Saudi Arabia, and I was going to be in Saudi Arabia, I told him to come to my event so I could introduce him to the event promoter so that he could get booked for the event the following year. And I did that. Right. So it's like always to your point, thinking about how else could I better connect support or help this person? Or is there someone else in my network that would benefit from being connected to these people? And then there could be some mutual wins. And when you start living like that, and like you said, putting those pieces together and playing chess instead of checkers, it's no big deal to send someone a text and say, Hey, I'd love to get ahold of Patrick, but David, I know that you've had him on the show.

25:44Do you know a way to connect me to him or anyone on his team? Here's what's going on. And I never look back and I'll never feel bad. We don't know what the outcome is yet. Of course, I have a feeling it's all going to go well and all work out in the end, but we'll see. We'll see how it plays out. But it just might open another door to another friendship, to another opportunity that we have no idea even exists yet. You know, I think part of it, too, is don't be lazy. You know, it's easy to just say, no, you know, I could have responded and we all can respond, you know, in this way and just say, hey, I don't know him.

26:20And, you know, and and then like I'm off the hook and all that. But that's just lazy. Like there were there's six degrees of separation all over the place. So there's, you know, probably a hundred different avenues to get that one thing done. And there's always, you know, multiple solutions to any problem. It's just a matter of whether you're going to put some of your brain power into it, or you're just going to hit the easy button and say, you know, no, sorry, I can't help you. It's so true. Like put the extra effort in, just show up and try a little bit and lean in with an open heart and good attitude.

27:02And you never know what can happen. And that doesn't mean, you know, so often, I'm sure you get this people sending DM, Hey, can I meet this person? Hey, can I meet this person that, you know, Hey, can I get on the, you know, can I be featured in your next book? What's the difference in your opinion from someone who's being strategic and asking for different things versus someone who's truly coming into your life that you're saying, you know what, this is someone I'm going to embrace and start a friendship and a relationship with. I had a different thought. I'll answer that question in a second.

27:34I think to our point before, people sometimes are too focused on outcomes and they forget that effort means something. So you and I have talked, I don't know, for a long time. We haven't talked about it recently, but we've talked about Lewis Howes. And we're not super close, but he knows me. I know him and, you know, I have pinged him consistently over the years on your behalf. And I think you've appreciated the effort. It hasn't turned into the outcome, but I'm not that worried about the outcome. I think people, I appreciate the effort. Like you've done so many amazing things for me. I appreciate the effort.