Creating Confidence with Heather Monahan
#514 Why the Best Networkers Don’t “Network” (And What They Do Instead) with Scott MacGregor, Founder of the Outlier Project
Tue, 22 Apr 2025
Want to build a network that actually changes your business and life? In this episode, I sit down with my longtime friend and community builder, Scott MacGregor, to talk about how the best connections aren’t transactional. He shares how he keeps track of 750+ relationships across 35 countries. He also shares the tools and mindset to build a global network rooted in generosity and trust. Get ready to grow your business, expand your circle, or become the kind of person others remember. In This Episode You Will Learn Why TRANSACTIONAL networking kills long-term connections. A new definition of FRIENDSHIP that will expand your community. How to be ONE OF ONE in your network. Daily habits to BUILD better relationships in work and life. ONE way to ask for help without ruining a relationship. Resources + Links Learn more about the Outlier Project HERE! Sign up for a one-dollar-per-month trial period at shopify.com/monahan Download the CFO’s Guide to AI and Machine Learning at NetSuite.com/MONAHAN. Want to do more and spend less like Uber, 8x8, and Databricks Mosaic? Take a free test drive of OCI at oracle.com/MONAHAN. Get 10% off your first Mitopure order at timeline.com/CONFIDENCE. Get 15% off your first order when you use code CONFIDENCE15 at checkout at jennikayne.com. Call my digital clone at 201-897-2553! Visit heathermonahan.com Sign up for my mailing list: heathermonahan.com/mailing-list/ Overcome Your Villains is Available NOW! Order here: https://overcomeyourvillains.com If you haven't yet, get my first book Confidence Creator Follow Heather on Instagram & LinkedIn Scott on Instagram & LinkedIn
Chapter 1: Who is Scott MacGregor and what is his background?
Heather, I could not be more excited for this. I've been looking forward to it all day. You know, I absolutely love you to pieces and I hold you in the absolute highest regard. You are one of the best podcasters on the planet.
Oh my gosh, thank you so much. That means so much knowing the network of podcasters that you have that you're close to. That means a lot coming from you. All right, so let's go backwards first before we move forward. Let's tell them a little bit about your backstory and your come up.
Yeah, you know, I grew up relatively poor in an affluent town. So I stuck out like a sore thumb because economically, you know, we were very, very different from everybody else. So, you know, as a kid, I was just trying to figure out the world and the world when you're a kid is the town you live in. Like, it really doesn't extend much beyond that.
And and I was just trying to figure out why were my experiences so different from my peers? and so that spur i think really spawned kind of a lifelong curiosity so i thought it was because of my circumstances but i'm 57 now and i will tell you i'm as curious at 57 as i was when i was seven So part of my journey has just been that trying to satiate that curiosity.
And I recognized early on in life that I was an outlier. I didn't call it that, but I knew very early on as a kid, I knew I thought differently about things than my peers. But when you're a kid and you think differently about stuff, Heather, you just think you're weird. Like, I wasn't celebrating it.
I'm like, there's something wrong with me because I do not think the way that everyone else thinks. And then later on in life, especially when I got into business, I was hitting levels of success that my peers were not. And I really stepped back and I'm like, why is this happening for me? I wasn't more connected. I didn't have more money. I wasn't better looking.
I didn't have anything that I saw as a distinct advantage, but I pretty quickly realized that That by being a contrarian, by always, when everyone was going left, I just intuitively wanted to go right. And by taking that path less traveled, that's where the pot of gold is in life. So I have leaned into that heavily, always in my career, but even more so now as an entrepreneur.
Well, can you give us some examples of some of the businesses that you've created and how you found success going the opposite way versus the general population?
Yeah. So the first business I started, I was a chief revenue officer. Sound familiar? Like somebody I know. And, you know, we had had massive success. We grew a company from about five people to nearly 300 and had double digit growth every single year for 17 straight years.
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Chapter 2: How did Scott build his successful businesses by going against the norm?
All right, so let's run it back to the beginning of the Standing O series, because I feel like the Standing O series kind of cracked open the door to the community and what you're doing now. So can you tell everybody a little bit about how Standing O came to be and what that book series is all about?
So when I started my company, Something New, 10 years ago, giving back to me was super important. But I had a huge problem. And the huge problem was I'm a total control freak. So I did not want to take any VC money because I didn't want anybody to tell me what to do.
So I'm like, how am I going to give back when I'm literally bootstrapping this business and I'm pouring every penny that I'm making back into the business? So I sat back and I'm like, well, what are my assets? And my assets were not a gigantic bank account that I could write checks to these organizations that I cared about.
And I realized very quickly that my assets were all these unbelievable friends that I had. So I thought, okay. What if I asked my friends to write a chapter of gratitude for a life lesson learned? I'll put it in a book and I'll give 100% of the proceeds to charity. So the first book that I wrote was called Standing O. And Dick Vermeule, who's in the Football Hall of Fame, wrote the forward.
And Tiki Barber, who's an all-time great from the New York Giants, wrote the cover quote. And then... Friends of mine from Jesse Itzler to Heather Monahan wrote chapters of gratitude, beautiful chapters of gratitude. And it worked. We sold a bunch of books. We raised a bunch of money for a couple of nonprofits that I was really passionate about. And we gave them a lot of exposure.
And so I thought, okay, this formula works. So I did it again with a book called Standing O Encore. And Another friend of mine stepped up, Heather Monaghan. I don't know if you know her, but she wrote the forward to standing encore. Jesse Itzler wrote the cover quote. And so we've done that four times. Fifth book will come out this year.
So I think it was a cool way to give people exposure to some of these unique friends that I have and hear their stories of gratitude for a life lesson learned. So maybe it was a little bit.
of a peek into their life that they normally wouldn't get the thing that it didn't satisfy was it's not it wasn't interactive and that's really what pushed it into the community where in the community people now get to ask the heathers and the dick for meals and the jesse's questions and that's a different experience so yeah the standing o series has been
Just a really fun way to give back in kind of a unique aspect. So I've loved it.
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Chapter 3: What inspired Scott to start the Outlier Project and Outlier Magazine?
I have always lived into the answers. You know, you talk about messy action a lot, and I believe in that so much. And, you know, I call it living into the answers. I think too many people, they have to figure out what the end of the game looks like in every step along the way. And that's not really how it works, especially as an entrepreneur.
Like, there are so many things that are going to come at you from left field. You have to be prepared to kind of go into uncharted waters and live into the answers. I mean, you have to have some idea of where you're going, but you don't have to have it all mapped out. So I'm very, very comfortable figuring it out as I go.
I've never heard live into the answers. Explain that a little bit better for us.
Live into the answers just means you don't have to have the answer right now. You live into that answer. So as you progress through, whether it's a business or whatever it is that you're trying to build or a relationship, You're just living into the answers. So as you're accumulating more data, you're making the adjustments and you're bobbing and weaving and making new decisions.
It's just inconceivable to me that you're going to know all that stuff up front. So you really have to live into the answers all the time. But most people get stuck because it's scary to do that.
know what's funny though i'm thinking about this when i'm listening to you talk i was thinking about the juxtapose of corporate america versus entrepreneurial which when you talk about living into the answers entrepreneurial is totally that however i was just thinking and i know this is not true this is a lie corporate america is not that here's what i notice now and i'm interested as you've had experience in both if you feel the same way you think it as an employee in corporate america
Everything is known. Everything is clear. We know you're told what to do and you're not living into the answer. However, that's actually when most companies really start to decline, whether they know it yet or not, when they just put things on rinse and repeat, especially with the employees living that way, you're taking a turn the wrong direction versus saying,
Living into the answers, you're always trying to reinvent. You're always trying to fail forward. You're always trying to find that next path. And that's how you ultimately succeed. Do you see it that way now that you're out?
I totally do. You know, it's the reason why I left. I worked at a Fortune 500 company and I had a ton of success. I was the youngest national account manager in the history of the company. And the company at that time was... I don't know, 80, 90 years old, but I left because I would have an idea. I was young. I was in my twenties and I'd have these ideas. I'd be so enthusiastic.
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Chapter 4: What is the Standing O book series and how does it connect to the community?
Do not stay on the Titanic if you're on it. For me, I remember thinking like, this is all I know. What if this is all I'm good at? Oh my gosh, yet again, that is such a lie. It's all about fear. Choose to see fear as a green light that means go and go faster.
Meet a different guest.
We'll see you next time.
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Chapter 5: What does 'living into the answers' mean and how does it apply to entrepreneurship?
So as soon as you put somebody in your mind, they're your friend, you start to treat things differently and things are no longer transactional and things are more about them than they are about you. So I think just refining your definition of what a friend is. I mean, I felt like you and I were friends very early on, like first conversation. I knew you. You knew me. I like you. You liked me.
And then, you know, so we went from probably. A situation where if somebody said, do you know Heather? I would say, yeah, I know Heather. To now, if somebody says, do you know Heather? I'm like, do I know Heather? I freaking love Heather Monahan. So it changes. There's a continuum of friendships. But I think having the mindset of viewing people as your friend changes the way you approach people.
I love that. I've never heard that before. Okay. I want to tell a story how we met because I think this is important for people to understand too, because I believe this is one of the reasons why you have such a massive network or so many friends. At the time I was engaged and my then fiance had a daughter who was getting ready to go to college and she wanted, I think it was NYU. Was it Scott?
Was it NYU?
It was NYU. She was interested in NYU. We didn't know anybody affiliated, but we wanted to get some intel on the school and see if it would be a good fit for her. So I said, let me go to LinkedIn where I have a presence and see who I know. You know, this is where I think LinkedIn is incredible. That network's amazing. So I just typed in NYU.
Somehow you and I were connected and you were an adjunct professor for NYU. And I just sent you a DM and I said, hey, Scott, Heather Monaghan, listen, I don't know how involved you are with NYU, but my fiance's daughter is really interested. And I wondered if I could jump on a call with you for just a couple of minutes and ask you some questions. Immediately, you were like, absolutely.
You got on a call with me. I talked to you about her. You're like, I'm happy to connect her with students. I'm happy to get on a call with her myself. You just offered, offered, offered. And then we kept talking, right? The conversation obviously didn't stop there. And that's really where our friendship stemmed from was, I was in need of help.
I raised my hand and said, hey, I don't know if there's any way you can help. And you were like, hey, done. Let's talk about how I can help. Let's talk about how I can help you solve this problem, which you did. And that really just shot our friendship off on a fast track. Don't you agree?
A hundred percent. And then you showed up for me consistently. You know, when I talk about friendship with people, I always use you as an example because you are somebody who shows up at the most inopportune times. And whether it's right before a TED Talk to come to New York for a book launch party or whatever the case may be.
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Chapter 6: How does Scott define networking differently and why does he focus on friendships?
And Gayle King's ability back then to do things was nothing in comparison to what her ability to do things is now as Oprah's best friend. So access gives you opportunity. And when you have a list of those people and you look at it every day, you can think, what can I do to pour into these people so that I can further this relationship. So I'm very intentional about building those relationships.
Well, I guess I am doing a lot, but it's organized and it's structured. There's actually a process to doing it.
Give us some examples of some of the things that you do. I mean, I'm very familiar with it, but for everyone listening who has no idea what you mean by this, in addition to you're going to be sending text messages, you're going to send video messages. What are some of the other things that you do for that list?
Yeah, I mean, it goes on and on. Planned random texts are one of my favorite things to do. So, for instance, like, I'm going to wish you a happy birthday on August 14th every single year, but I would rather send you a message September 14th because you're probably not going to get anywhere near the volume. So... planning those things out is something I do. Or I believe in being in the moment.
When I see something good, when I see something that I want to celebrate, I don't wait because I'm going to forget. I do it immediately. So that's why you've been the recipient, unfortunately, of some of this. You get the me at 5 a.m. on my treadmill. I've got bedhead. I got bags under my eyes. Thank God. I'm sure I'm not smelling great. That's not an issue.
But if I'm thinking about somebody in those moments because I'm maybe seeing something that they accomplished on social media, I'm going to send a message. I don't care what I look like. And those things are really appreciated. And then... You know, I love to gift things. I'm a big gift giver.
And I think sometimes people get paralyzed about gifts because they think you have to spend a lot of money. And in some cases, you should. Like, if you're going to do something, make it best of class. But it could be something that's just thoughtful. So, for instance... Brandi Chastain is a good friend of mine. So Brandi is a two-time World Cup champ, two-time Olympic gold medalist.
She's in the soccer hall of fame. And you can't get anyone who's more into soccer. So I was in the post office one day and I saw these U.S. National Women's Soccer stamps. So I bought a bunch of stamps and I bought stationery and I sent it to Brandi. So
You know, the stamps and the stationery didn't cost me very much money, but the thoughtfulness behind it and now her ability every time she sends a friend a note using that stationery and using those stamps, she's probably going to think, oh, you know, my friend Scott sent this to me. So my good friend, the late John Rulon, who is devastating that he passed away.
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Chapter 7: What are Scott’s practical tips for building genuine relationships on platforms like LinkedIn?
You don't have enough chits on your side of the scale to ask. So I only ask for things when I think the scale is in proportionally balanced in my favor. And at that point, I will ask for something like, Heather, will you write the foreword to my book? If it's not, I'm never going to do it.
But most of the time, I don't even have to ask because people will come to me and say, you know, what can I do to help you out? Because, you know, I've done things for them.
Well, a lot of the times when you ask for something, it's something that benefits me personally anyways. So for example, writing a forward and a book, that's a big deal. That's an honor in my opinion, right? So that's not a heavy ask. You ask me and you always ask ahead of time, hey, do you mind if I connect you with this person? They want to be a guest on your show or whatever it may be.
You're always sending me incredible people that of course I would love to have them be together. So I guess my point is, it's not like you're asking me to clean out your garage on a Saturday and Sunday, you know, with a pickup truck. Like these are things that actually benefit my life. And that's just, you know, too often people are like, oh, I'm afraid to ask my friend for this.
But if you're asking for something that actually could benefit them too, you might be surprised at how excited they're going to be by it. I know that that's how I typically feel. Whenever you ask me to do anything, I'm excited.
That's so true. I will say there are times when you have to shoot your shot and you just have to go for it, but I think you have to be cognizant of the fact that that is going to be probably a transactional relationship. And it's going to be just a drive-by friendship.
But if you have something, you want somebody desperately to be on your podcast or something like that, then there are times when you're just going to shoot your shot. But I view building true relationships as having no timeline. So I think the other important thing is never keep score. So do not keep score, meaning I did this, I did this, I did this, I didn't get anything back.
Number one, it will drive you nuts. And number two, you'll lose sight of the fact that you're actually playing a game that has no scoreboard and it has no clock. So that's the way I view relationships. There's no timeline. I don't care if it takes six days, six weeks, or six years to build that friendship. And sometimes that friendship is just a friendly friendship.
And other times it is a friendship like you and I have, which is a ride or die, like Heather needs me to bury a body while we're in the shovel.
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Chapter 8: How did Heather and Scott’s friendship begin and what does it teach about networking?
So whether it's you or Leila Ali or Rudy Ruediger or Jesse Itzler or whoever, those are kind of cool experiences. So we're trying to really create something that accomplishes two things. Number one is help people develop really unique relationships with a very eclectic group of people and help people to have learning and development opportunities in an extremely unique way.
And I think we've accomplished both of those things. And that probably is attributed to all the growth that we've had.
One of the things that I like about the Outlier Project is what you're saying, that you get access to all of these leaders, all of these personalities live in real time. You get the community, but you also do in-person events. And I have so enjoyed your in-person events. Can you tell us a little bit about some of the Outlier Project in-person events that you do?
Yeah, so I think people crave in real life. People, you know, they want to be together. Like this Sunday, I'll be in Atlanta for an event for Culture City with Dominique Wilkins and a bunch of other outliers. I think that's a really important component. We try to do things that are really fun, whether that's skating in Rockefeller Center or, you
In a few weeks, we'll be in San Jose, California to go to a soccer game with Brandi Chastain. She owns a pro women's soccer team called Bay FC, so we'll tailgate with her before the game, which is going to be a cool experience for people that have maybe only seen her on TV in the past. We do humanity expeditions.
So we go to Nicaragua every year and we help rebuild schools on a mountain in a town called Matagalpa. We just do a lot of really cool, unique things. And that's been a big, big component of the Outlier Project. It doesn't have to be a soccer game, though, with Brandi Chastain. It could be, you know, we were just in Charlotte. We played mini golf in Charlotte. And, you know, we had a blast.
We went bowling. in atlanta on not that long ago and and just had a fantastic time just being together so in real life stuff is another big component of the experience that we want people to have for anyone listening that is interested in becoming a part of your community where do they go and how do they become part of outlier project Yeah, it's very simple.
They go to the outlierproject.live and joining. There is no application. If you want to join, you literally just join. It takes about 20 seconds, and it's as simple as that. Fortunately, I think because of the people we have in the community, we really have had no issues with... with that. And I've had two people that I've had to ask to leave in the two and a half years that we've been running it.
So pretty good track record. So there's no need for an application. So people want to join. If people resonate with being an outlier, wanting to show up differently, wanting to take the path less traveled, knowing that that's easier when you're surrounded by 750 people who think that way, it's a really fun experience.
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