Intentional Relationship Building: Scott MacGregor on Why Human Connection Beats Everything | Ep 50

What if the most powerful business strategy has nothing to do with strategy at all?

In this episode, Aimee Rickabus talks with Scott MacGregor — founder of The Outlier Project, publisher of Outlier Magazine, and 4x author — about why intentional relationship building is the one skill AI will never replace.

Scott shares:
- His "extra inch" philosophy that turns 5 seconds of effort into massive impact
- Why he ditched networking for friendship building (and what changed)
- How he uses his phone contacts as a personal CRM to remember what matters
- The Warren Buffett approach to relationships: slow, steady, outsized returns
- Why he's capping his community at 1,100 members — "scale can steal the soul"

Whether you're an entrepreneur feeling stuck in transactional relationships or a leader wanting to build deeper connections, this conversation will shift how you think about success, trust, and what people actually remember about you.

🔗 CONNECT WITH SCOTT MACGREGOR:
LinkedIn: https://www.linkedin.com/in/macgregorscott/
Instagram: @scottmacgregor_official
Outlier Magazine: https://www.outliermagazine.co
YouTube: @theoutlierproject

🔗 CONNECT WITH THE MANAGE HER:
Website: https://www.themanageher.com
Instagram: @themanageher
Full show notes: https://www.themanageher.com

Transcript

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🎶 Music Outro 🎶 Welcome back to The Manage Her Podcast, the show where we explore the unseen skills that actually build power, leadership, and lasting impact. Today's conversation is something I believe will become the most valuable currency of the future, intentional relationships. As technology accelerates, AI, automation, systems doing more and more of what humans used to do, there is one thing it still can't replace, genuine human connection. My guest today is someone who embodies this better than anyone I know, Scott MacGregor, founder of The Outlier Project. Scott and I were introduced by my friend, Lindsay Dowd, and just over a few months ago, I've witnessed something remarkable. The way Scott builds relationships, not fast and transactional, but slow, steady, and deeply intentional. On my birthday, Scott was the first person to reach out, not with the text, but with a personal video message. It was thoughtful, aligned, and exactly what I needed that day, and it left me wondering, how can someone who's only known me for a few months be so attuned? Today, we're digging into that, the soft skills, the systems behind care, the art of connection, because Scott isn't just a founder, he's a connector, a people whisperer, and a living example of what leadership looks like in a relationship-driven future. Hi, Scott. I'm so glad to have you on the show. That was the coolest introduction. I've had a lot of introductions. That might be my all-time favorite, the people whisperer. I love it. You really are. I've never met anybody who can understand someone as quickly as you can. You're very intuitive, and it is a very special gift to share with the world at this time. Thank you. Thank you. Yeah, absolutely. So, Scott, you've built your work and your life around people. As technology takes over so many functions, why do you believe relationships will become the most valuable currency moving forward? You know, I think it's always been the most valuable currency. So I don't think it will become the most valuable currency. I think it's always been like that. As AI and all kinds of things take over, people are craving a human connection. And I think when you think about it, If you're really looking for true support, if you're looking for trust, if you're looking for collaboration, if you're looking for customized, bespoke learning and development opportunities, you really can't get that outside of human connection. So, you know, I think there's nothing beats it. It always will be championed. Yeah, I know for me in business, if I look back at my success, it always comes down to relationships. Everybody thinks it's the thing that you do, but it's actually the thing that you're being, the human being that you're being that will actually get you to your success. It's no one thing that you do. It's the actual, you know, being fully embodied in yourself and meeting other people and meeting them where they're at is actually what will lead to your success. At least that's been my case for sure. So let's go the power of going the extra inch. You are the king of this. You consistently do something small but powerful. Personal voice notes, videos, thoughtful follow-ups. Why do you believe going the extra inch matters so much? And how has that shaped the depth of your relationships? That's a great question. You know, I think we live in a world where people are mostly trying to figure out how do I do the least in order to get a result, right? instead of having the mindset of what's the most that I can do. So I think that mindset can be really, really powerful. I think details matter tremendously. The devil's in the details. The details matter. I always think of like, there's so many little examples you could give, but I see this every day. And I saw this literally just before we hopped on this podcast. I had sent a message to somebody, And they replied to me and didn't write, they didn't even write the word thanks. They wrote just initials. So here's my thought process. I appreciate that. Like, I appreciate somebody thanking me. But whether you write, you know, THX or you write thanks, what if I wrote, thanks so much, Amy. I really appreciate you. I lost count on my fingers, but that's like maybe like seven more words. The return on investment, the impact that that has is like times a hundred. So that might take me another five seconds instead of just saying, thanks. Thanks, Amy. So much. I really appreciate it. You know, something like that. It's so simple. So those little details matter immensely. tremendously. And I think just going that extra mile makes people feel like you really care. Yeah. Couldn't agree more. I know I had never really been into the whole audio message world until I met you and Lindsay and you guys are like so good at the audio messages, which is like a voice recording. It's kind of like sound like a text, but I just, it's so much more personal. It's just it really it's it's so nice because we rarely hear each other's voices anymore because we rarely speak on the phone any longer, you know. So it's nice to get that personal touch of hearing someone's voice. But the video message you sent on my birthday. Oh, my gosh. I was like better than my mother, better than my father, better than my brother. And I'm thinking to myself, what? Like, how did he you just met me a few months ago? So how do you listen to people so well that you can show up that way? Like, especially when you've only known them a short time. I mean, I think it's simple. I care. I think if you care, if you really care, I know this sounds super basic, but I think like a lot of life is very basic. I truly genuinely care. I give a, you know what? And so because of that, I really am tuned in because I care. And I think people leave clues all over the place. Like, especially now with social media, people are, they're littering clues everywhere. And if you care, it's very easy to pick up on those clues and be like, you know what? December 3rd, that's Amy's birthday. I'm going to send her a message. And I'm going to wish her a happy birthday. It's easy. And I think, you know, don't go for polished. I probably left you that message at 5 a.m. on my treadmill. You're on your treadmill. You're walking. I love that because there's no such thing as the perfect moment. If you get caught up in perfection, you just won't do it. Right. So if you're like, I'm just going to do this because I care and I'm doing it out of a place of love. And the perfection doesn't matter. And I need to in me and myself, I have to work on that because I work. I mean, I definitely battle my inner perfectionist and it holds me back from from communicating what I really care about people. And that's that's something I personally need to work on. And I'm learning from you how to do this. But do you is there some sort of technology you're using to help track this or how are you keeping yourself so organized? Again, it's a simple solution. So I, you know, I think you can use certainly a CRM. You can use Salesforce or you can use something like that. Honestly, I think this is, should be your CRM. So I put everything in my phone. The reason why I do that is if I'm somewhere and I see somebody, you know, what am I going to, I'm not going to whip out my laptop and like, you know, look up, you know, your name in Salesforce and all this information, I can very, I always have my phone on me. I can quickly check and I can see kind of all the things that I think are important. And the things that are important is like, you know, your birthday and your significant others and your kids and all those things, your pets and all the things that people hold near and dear. I put all of that stuff in my phone. I also do a lot of stuff up front. So before I even meet somebody, I had about seven or eight meetings today with new people that I'd never spoken to before. And this is not to throw anybody under the bus, but all seven or eight of these people, I knew way more about them than they knew about me because I spent a little bit of time looking into those key things that are important to them. And it just makes such a huge difference. It's not that hard. I think you just have to get in the habit of doing these things. It has to just become routine. So for me, it doesn't seem daunting because it's very routine. And the system that I use is just loading everything in my phone so that I can very quickly look up information. So all in your contacts, where the notes are, you just put notes on the people. That is great. Brilliant, Scott. It's a simple solution to something that, why didn't I think of that? That's awesome. My husband has been doing this for years in his CRM for sales. He's an amazing sales guy and he knows his customers' favorite teams and their dogs' names and their kids' names and their kids' teams' names and all of the things. And he's so good at it. And you do it, I'm super impressed how well you do this. It's really impressive. So everybody, we have this myth of I don't have time. You know, so many leaders are like, I don't have time to do that with everybody. But how do you respond to that? And how do you personally manage them without it becoming transactional or overwhelming for you? Yeah, another great question. I mean, for me, I've always I've been in a leadership role since probably my mid 20s. And I've always realized that my success or failure was going to be predicated on my relationships with other people. And certainly the people that reported to me. So I don't think you can't, I don't know how to, I'm going to say this wrong. You can't not have time to not have time. Like you have to have time. It's the most important thing you could possibly do is be an effective communicator and let people feel seen and heard. You can't possibly not have time for that. I mean, I'm a big believer in communication. the concept of people over everything. You know, if you want business success, if you want successful relationships, if you want good things to happen, you have to invest the time in order to get those results. So to me, that's what it's all about. I love it. And so how, but how are you keeping it from being transactional? Like you really are amazing at making it just sincere. You're so sincere. You know, it goes back to with, you know, I don't really want to repeat myself, but I'm going to, I think, unfortunately, it just, it goes back to caring. Like if you truly care, you won't be transactional. People will understand that this is genuine. It's just kind of who you are. It starts with that mindset of truly, truly caring. And I guess, you know, some people, they don't care and they just want, And it doesn't mean you're not going to have any success, but I think you have to be okay with what I would call like a drive-by relationship. It's not going to be anything other than transactional. But to me, that never really feels great. Like I want to build friendships with people. I don't want things to be transactional. I love it. It's such a beautiful mindset shift for the future that we're moving into with all of this new technology, being able to do so many things for us, you know, but the trans, it will be able to do transactional. I do think that AI will handle transactional relationships, but it's not going to be able to handle the caring part of it. I agree. Yeah. Yeah. So this is, this is our, this is our work. If we're going to be successful in the future, this is where humanity needs to put a little more emphasis and a lot more time and a You know, it's your attention, it's your time and your present moment. What are you going to do with it? These are the real, this is the real currency. It's not money. It's your time, it's your attention, it's your present moment that you're in. So it's about leveraging those things. And in my work, I talk a lot about invisible labor, relationship buildings often unseen, unmeasured and undervalued. How do you think this invisible work creates disproportionate long-term rewards or returns? Your ROI. I have always, I've wound up in these great spots and I always, I'm like, how did I get into this room? How am I in this conversation? How am I in this relationship? Like, how did all this happen? When I sit in those spots and kind of think about how did this happen? I reverse engineer things. And when I reverse engineer it, it's never a straight line. It's not like, oh, I met Lindsay and then Lindsay introduced me to Amy. It's a crazy circuitous path that put me in that good spot that I would have never been able to predict up front. And I think a mistake that a lot of people make is when they meet somebody, they're trying to figure out what the end result is going to be. And they're trying to predict the future. And I just choose to kind of live into the answers. I choose to say, is this an interesting person? Is this a person that I want to build a friendship with? And if the answer is yes, then I'm going to pour into that person, not really knowing where it's going to take me, but knowing that historically I've wound up in these good spots that I wouldn't have been able to predict because they are this crazy circuitous path that brings you there. you know, I don't think you can predict these things. You just have to pour into people and know that good things are going to happen. I love it, Scott. You do that. You definitely do. You're amazing. So I have to ask, how do you keep all this organized? The people, the details, the timing without losing your authenticity, without the heart behind it. Cause you're running a community too. You've got a community. The outlier project is what, like 800 people now. Yeah. Yep. Yeah. You know, again, I use my phone as like my CRM. So I've always got that stuff. I do care. And when I care about something, this is the interesting part of caring. When you care, you remember stuff. When you don't care, you forget. So, I mean, this happens to me all the time. There are moments where I truly don't care about something and I very quickly forget these things. But when I do care, It sticks with me. It sticks in my brain. So part of it is just like we all have this supercomputer between our ears and leveraging that is easy when you truly do care. I try very, very hard never to be transactional. I want everything to feel authentic and real and true to who I am. And I think hopefully that comes across well. in my communication and the relationships that are built because of it. Oh, I would say it does for sure, Scott. It's actually super impressive to see how you do these things. So being a people whisperer, I just think you are a total people whisperer. If someone listening wants to become a better connector, not louder, not more performative, but more attuned, what's the first shift they need to make? Great question. It's mindset. So I think a lot of people focus on the tactical, practical things that they could do. Like, what can I do to build a relationship? But if you don't have your mindset right, if you don't understand why am I doing this? So I am very much against the word networking. Like, I don't like networking. Networking to me, just it screams transactional. And so I'm not trying to build my network. I am trying to build friendships. And I think just when you think about that from a mindset standpoint, like I'm not trying to build a network to get to a business objective. I'm trying to build a friendship that will enrich my life and how that will manifest itself. I have no idea and I don't really care. I just know good things are going to happen. So I, it always starts with kind of that mindset that you have. So I would say ditch the network and focus on just building true friendship. So we all know how to build a friendship, but somehow we got into a business context and we became these like business card swapping network machines. And it just really doesn't produce great results. Oh, I couldn't agree with you more, especially in the women's in business world, the networking. There's so many networking events. There are so many organizations and it is very transactional and it's very nice when you meet people that actually just want to be your friend. So nice to meet the actual friends. I have one friend who texts me every Monday and actually she texts me every Sunday and it's always, you know, wishing me a really nice week ahead. And it's just such a nice little thoughtful touch. thing that she does every week. And it's those little things. It's those little things that just make you feel seen. It makes you feel remembered. And it's, it's the, it's the slow and steady and it's the longterm. And you're so good at this. You take a very long view approach to relationships in a world that's obsessed with speed and scale. And right now it's a, Oh my gosh, how many followers do I have on social media and all this stuff? But why does slow and steady still win the race? You know, I'm not a genius, but look at what Warren Buffett does on the investment side. Like, you know, he's not looking for short-term gains. When you look at successful organizations, even if they are beholden to wall street or VC backed, you know, they are really making long-term bets. You know, you see that in world-class athletes, you know, what they're investing time after time, like the consistency over time to get a result down the road. Like we all know that that's how things work uh it's the same thing with relationships. It takes time uh and effort. But when you put that time and effort in to relationships, you get those Buffett results. Like you get that massive return on investment. In order to build real relationships, you have to build trust. Sometimes you can build trust very quickly because if you're just a very, like you're a very genuine, authentic, I remember the first time we met, we instantly had trust because I just knew right away, you are an open book. Like you are who you are. And that builds trust very, very quickly. With other people, they're not quite like that. And it takes longer to build that trust and build those relationships. But it's always worth going slow to build that because the ROI is so enormous. So don't listen to me. Listen to Warren Buffett and people that are a lot smarter that understand that In order to get outsized returns, you've got to be willing to kind of pound the rock for a long, long time. And that works in investments. It works in athletics. It works in relationships. It's amazing. Well, I was reaching out to Jen Drummond to have her on the show. And she is training again. Speaking of that slow and steady, she is training again to break another record. Guinness book of world record. And so she's going to be on my show in October because she is currently, she has seven children now. I know. Crazy. She's got you beat. She's got me beat. Yeah. And so, yeah. So she's, it's just a really good example that athletic, you know, I think we all watch athletes do the slow and steady approach. There's no quick way to become an athlete, a professional athlete. You know, it's, it's about pacing yourself slow and steady, you know, every day you have to show up, you've got to do the practice. You might, you know, it's every, it's being present in the practice every single day for years and years and years. And it's the same, you're right. If we show up with the same mindset, I might not be perfect at this. I might need to continue to learn how to do this, but I'm going to show up. I'm going to come, come with a mindset of caring and I'm going to, and I'm going to give it my, the old heave ho and see what I can do and see, you know, if I keep showing up for these people in their life if I can build trust and get into some sort of reciprocal relationship where now they trust you and you can trust them and now we have this lovely thing called a relationship. There's nothing better. To me, relationships are everything. So every day I go into the day excited about building relationships new friendships. You can't have too many. And you're always going to have your core people who are like, you know, your confidants. But you can have a legion of people that are your mutual fans of each other and supporters. And I'm certainly that for you. Everything you've done in your business with Tomahawk, what you've done with your books and the podcast is just, it's so inspiring. I absolutely love it. Oh, thanks, Scott. I feel the same way about you. And you've got the community growing. You've got the magazine going. How many issues are we on now with the magazine for Outlier? We're eight issues in. We have 100,000 subscribers. So the magazine's doing really well and the community continues to grow. So, yeah, having fun. It's just it's next level. It's so fun to watch other people do big, cool things, legacy things. Things that are beyond, because at some point in your life, you get beyond the making money part of your life. And you're like, now how am I going to give back? How am I going to contribute to society in a positive way? I have the time now. I have the wisdom now. And I feel like you really jumped into it with this project that you're in now. Tell me about this project. Yeah, it's all about impact. At the end of the day, are people going to care about the companies that I built? Probably not. Are they going to care about books I wrote? Probably not. Awards? No. House I live in? Car I drive? All those things that people typically note you for, like no one at the end of the day is going to care about that. The impact that I make, people are going to care about that. They won't care about it forever, but they will care about it. And so that's what I think about. It's all about impact over income. Income, there's nothing wrong with making money. And I want to make you know, a whole bunch of money. I've always been motivated to be successful monetarily because it does allow you to do things that, that you can't do otherwise, but you know, impact in people's lives is what makes me jump out of bed every day. Yeah. I love it. I know for me, I've, I hit 45 and I went, wow, I'm going to get old and I'm going to die. What am I going to leave behind for my kids and my grandkids? What kind of impact am I going to have on the world? What am I going to do with the rest of my time here? And then it really became clear to me that this was what I really needed to do. I needed to use my voice and my stories and my wisdom and the personality that God gave me and just go for it and put it out there so that other people can, you know, learn and hopefully give them some hope. that anything is possible for them too, that they, you know, all you have to do is believe in yourself and that, you know, it's possible, but you only first, you got to believe in you, you know, you're the, you're the first one you got to first, you got to have a dream. You got to imagine a future for yourself and believe that you're worth it. And then, you know, life will follow you. We will follow you. It will follow your mind. You know, the things will materialize and manifest for you if you can do that for yourself, but you've done such a good job with that. What's, What's next for you? What's next in this project? I'm not looking to grow the biggest community out there. As a matter of fact, we'll probably stop taking new members at, you know, I don't know exactly what the number will be, probably like maybe 1,100, 1,200 members. We're at about 750, 800 right now. The reason for that is I have a little bit of a paranoia. I have a paranoia because I've seen this play a million times in my life where really good things... grow because they're good. I mean, it makes perfect sense and they continue to grow and then they kind of hit a plateau. They very rarely fall off a cliff, but what I've seen is that very slowly they become a watered down version of what made them great. And when you're in this trajectory, you're consciously trading impact for income. You're saying, I care more about the income than I care about the impact. To me, a watered down version of of the outlier project or anything else that i'm passionate about isn't worth it. And I think it's always sad when you see these things that at one point were great and then they just pushed for too much revenue or too much scale and they kind of, they're not really what they used to be. Like when i walk into a starbucks now, I don't get the same feeling that i got 15 years ago. It's different. It's true. And there's so many other examples. So I'm not. Scale can steal the soul a little bit. I love that. Yeah. Yeah. That's a good one. I'm going to steal that. Yeah. So I'm just excited about bringing amazing people. Into the outlier project, giving people amazing experiences. We've got some huge announcements coming up. That I'm really, really excited about some new stuff for our members. And we've got some amazing people coming up to people that you'll love. Gabby Reese and Laird Hamilton are coming up. No way. Fantastic. I love chatting up with them. And they're also going to be featured on the cover of our summer issue. So I love Laird. I met him in Kauai last summer. Last time I was there. Yeah. And he's freaking awesome. He's amazing. You talk about a power couple. They're amazing. They're just next level. They're so cool. They're perfect for the outlier project. They are truly outliers. They are. And in fact, I mentioned my conversation that I had with Laird in my new book. Oh, really? I really do. Yeah. We got into fear, facing your fears. And, you know, he's the guy. Like for me, it's been facing your fears like, oh, publishing this book or whatever. doing a podcast or whatever. And for him, it's like getting down this gigantic wave, towing into a 50 yeah yeah holding your breath for more than eight minutes, you know, and he really faces these physical fears that are so amazing. Then it all, everything he said, everything seems impossible until it's possible. Yeah. Yeah. it's wild. Yeah. He's fabulous. But tell me about Nicaragua too. We leave next week for Nicaragua. This is our third humanity expedition in Nicaragua. So a buddy of mine that I played high school football with, Peter Shaler, has lived in Nicaragua for about 25 years, and he started a nonprofit called Rayo de Sol. And every year we go and support him. We fly into Managua, and then we take a three-hour bus ride to Matagalpa. And we rebuild schools on the mountain in Matagalpa. It's the best work imaginable. It's my favorite thing that we do every year. Nicaragua is the second most impoverished nation in the Western Hemisphere, behind Haiti. So it's poverty to a degree that I almost can't comprehend. Yet the people there are... the happiest, most giving, wonderful people. And it just, it puts everything into perspective and it's a ton of fun. So I'm really, really excited. We're bringing a big group this year and I can't wait to get there. Oh my gosh. Scott, you and the Outlier Project, you guys, it's just an amazing group of people. I'm so proud to be a part of this group of amazing people. This conversation reinforces something that I believe deeply, that the future doesn't belong to the fastest or the loudest or the most automated. It belongs to the most connected. So thank you for not just what you're building, Scott, but how you're building it. You're a reminder that relationships aren't a side effect of success. They're the foundation of it. Thank you for modeling what intentional relationship building looks like. and for reminding us that care is not a weakness and that presence, real presence, is a leadership skill. If this conversation resonated and you want to learn more about Scott's work or stay connected, you can explore the Outlier Project and its community through its online platforms. Read and subscribe to Outlier Magazine for deeper thought leadership and long-form conversations. and connect with Scott directly on social media, where he regularly shares insights on leadership relationships and intentional living. We'll link everything in the show notes so you can find him easily. Scott, do you want to throw out and out there, but where you got a social, social media, the best place to find me is LinkedIn by far. Um, I'm still a, an Instagram idiot. I have not cracked the code on Instagram at all. Um, so definitely find me on LinkedIn. Um, And I love to connect and build relationships. Just tell me when you do connect with me, just say what you're hoping for and why we're connecting. And I'm looking forward to getting to know people. Amazing. To everyone listening, the message here is simple but powerful. The extra inch matters. The voice note matters. The video message matters. Because in a world where so much is automated, being human will be the advantage. Until next time, I'm Amy Rickibus, and this is The Manager Podcast.