Scott MacGregor: Founder & CEO of The Outlier Project

Episode 598

On this episode of The Kara Goldin Show, I’m joined by Scott MacGregor, the Founder and CEO of SomethingNew and the visionary behind The Outlier Project. Scott shares how he's redefining talent acquisition and creating environments where people can thrive. We dive into The Outlier Project, exploring how this unique community is helping leaders and entrepreneurs stand out by fostering a culture of excellence, giving back, and pushing boundaries.
Scott also shares some wild stories from The Outlier Project, his take on gratitude in leadership, and how to shift mindsets to become true outliers in your field. Tune in to hear Scott’s game-changing insights on building a community of top-tier talent and learning from the best. Now on The Kara Goldin Show!

Resources from
this episode:

Transcript

Kara Goldin 0:00
I am unwilling to give up that I will start over from scratch as many times as it takes to get where I want to be. I want to be you. Just want to make sure you will get knocked down. But just make sure you don’t get knocked out, knocked out. So your only choice should be go focus on what you can control. Control. Hi everyone, and welcome to the Kara Goldin show. Join me each week for inspiring conversations with some of the world’s greatest leaders. We’ll talk with founders, entrepreneurs, CEOs and really, some of the most interesting people of our time. Can’t wait to get started. Let’s go. Let’s go. Hi everyone, and welcome back to the Kara Goldin show. I’m super, super excited for our next guest. Scott MacGregor is the founder and CEO of the outlier project. You may know him. He’s been around for a while. He was also the founder and CEO of something new and that is still alive and growing and and amazing. We’ll get him to talk a little bit more about that, but The Outlier Project is really something special, and I think Scott has done an incredible job of really bringing people together, community of leaders, entrepreneurs and change makers, to learn, grow and ultimately give back in ways that truly move the needle. So his dedication to excellence and passion for making a difference is definitely a standout, and plus, he’s just a super good guy. So, I mean, you gotta, you gotta, just like, love that part. So, so, so, giving. So, really, really excited to have Scott here with us here today to talk a lot more about everything he’s up to, but in particular the outlier project, I really want to let everybody in on what you’re doing over there. So welcome, Scott, thank

Scott MacGregor 2:02
you. This is an absolute honor to be with you. You know, I have just the absolute utmost respect for you, so I appreciate the opportunity

Kara Goldin 2:15
so so nice. Well, you and I met, I guess, when I was launching my book, and you gave it a platform to I met with your group and advised it over the years too. But before we get into that like, what sparked the idea for the outlier project? How did you think about this, and how did you know that it was going to make the kind of waves that it has. Yeah,

Scott MacGregor 2:43
I’ve always wanted to live a life of impact. It’s been very important to me for a number of reasons, that I can get into some of the specifics of why, but I always thought of myself as an outlier. You know, I grew up pretty poor, but I grew up poor in an affluent town, so I stuck out Carol like a sore thumb. You know, there was no place to hide. It was very obvious that economically, we were very different from everybody else in the town I grew up in. Luckily, sports level the playing field for me and, you know, so I had a good friend group, and I wasn’t bullied, and I was, you know, very lucky in that regard, but I always knew I thought a little bit differently. And, you know, when you’re a kid and you think differently, you think I’m a little weird, like I don’t think the way that everyone else thinks. And it was interesting, because later on in my professional life, that contrarian nature, that outlier ish, desire to not go with the thundering herd, but to kind of carve my own path, was leading to consistent success, and I realized the benefits of being an outlier, the benefits of taking that path less traveled. And I knew that there were more people like that than just me, and I knew that a community was something that was very scalable and that I could have a tremendous impact. And I had grown a company before from five people to 300 and I really didn’t have a desire to grow another company to 300 employees, to be honest. So I decided to take the path of building a community. And today, we have 750 members in 35 countries. We just added a member in Romania yesterday, so that’s our 35th country, and it’s been growing like crazy, and it’s just been exciting to see the impact that we’ve been able to make to help people you know, embrace being an outlier, to celebrate people that are courageous. Are not afraid to call her outside the lines and take that path less travel, because that’s where success lies. Definitely.

Kara Goldin 5:08
So people join your group. 750 plus people are have joined from all over the world. Where are most of their heads at this point, when they, when they come in, are they trying to scale a business? Are they trying to figure out what to do next? A little bit of all of the above. I mean, tell, tell us more about it’s

Scott MacGregor 5:35
a great question, you know. Cara, when I started the outlier project, you know, people would say, what’s your avatar like? Who are you? Who’s going to become a member? Because our ethos is, anyone can be ordinary, but we all have the power to choose to be extraordinary. So we’re trying to help people chase their version of an extraordinary life. And when you think about that, that could be anybody on earth. And while we have members from Google and meta and Nike and Apple etc, about 80 to 85% of our members are entrepreneurs. And so we analyzed it a ways back, and we said, Boy, we are, you know, predominantly an organization that seems to be attractive to entrepreneurs. I think it’s, you know, when you’re an entrepreneur, especially if you’re a solopreneur, it can be a very lonely existence. So being surrounded by 750 people and not 750 people that are all in one industry, like sherms a great community, but it’s all HR people. The Outlier Project is people with backgrounds in finance and it and sales and marketing and you name it. So the amount of support that they are able to garner through their fellow members and through the people that we bring in, you know, for the learning and development opportunities really makes, I think, entrepreneurs, the people that seem to gravitate towards, you know, becoming members.

Kara Goldin 7:20
So you’ve built The Outlier Project on the foundation of learning and and giving back. Not just you’re not just talking at people, but there’s an expectation that goes on in the group too in terms of giving back. So what’s one standout story from the community that truly exemplifies these values. You

Scott MacGregor 7:42
know, giving back is incredibly important to us. So we have an arm of The Outlier Project called Top cares. And one of the things that we did for the first time last year, that I’m very excited to continue, is we decided to do a humanity expedition to Nicaragua, and so a bunch of us went to Nicaragua and helped to refurbish an abandoned school at the top of a mountain in a town called matagalpa. And it was through a member, Peter Shaler, who runs this organization called Rio de sol. But you know, we we walked away from that experience so inspired to really double down on what we can do collectively as a community to make the world a better place and to give back and and we’ll do that certainly through more humanity expeditions around the world, but also through just supporting other nonprofits that you know might be a little bit under the radar. I always think that, you know, people don’t give money, they don’t donate to organizations they don’t know about. So I think you know, recognition and exposure is such an important component. And because now we have a large platform, and also through outlier magazine, we have another platform to really help people with awareness for some of these organizations that are just doing great things in the world.

Kara Goldin 9:16
Yeah, definitely. Well, I love that The Outlier Project is really you’re supporting people who are just trying to be better on many fronts, and maybe many of those people never even thought about going to Nicaragua to do this right. And Yet, You’re bringing like minded people together to work on pretty big initiatives, and I bet it changes them right when they come back, and how they think about things, and maybe how that affects their their thought process for their business too.

Scott MacGregor 9:50
You know, it’s interesting that you said like minded, because I have a different take on that. I I think because we’re The Outlier Project we do, we have a lot of people. With a lot of different opinions on a lot of different subjects. So I think of us as like hearted more than like minded, so lots of divergent thoughts within the outlier project, but a heart for being very accepting and learning from other people. And I think that’s been one of the most beautiful things about building this community is when you bring together people that don’t all think the same, but have the same heart, the things you can accomplish are unbelievable. How

Kara Goldin 10:35
has The Outlier Project really expanded? I mean, you talked about the number of members, but how has it expanded from the beginning when you were first starting in terms of the thought process? Because it is evolving. Every business evolves, right? But also there’s such a key, I hate to use this word, but problem that exists out there. You talked about loneliness, but the digital and remote generation right now, there are, you know, Amazon just announced that everybody has to go back five days a week. We’ll see what happens. So that, like, there’s, there’s this world out there right now where people are trying to figure it out, and at the end of the day, you’ve got people who are also starting businesses, or entrepreneurs, they’re trying to manage people. It’s lonely, all of these things. But what are you seeing with the outlier project, and how that’s really evolving over time?

Scott MacGregor 11:32
It’s grown really through word of mouth, which has been great. You know when, when I started, it was interesting. I was going to have an application process, and I was really kind of concerned about the concept of one bad apple can spoil the bunch. And I have a good friend, David cancel, who is now the chairman of drift. It’s a billion dollar unicorn company. And you know, one of the things that he always talks about is take the friction out of your business. And I realized that an application process was going to be friction, so I thought, let me live into the answer. Let me see what happens when we open up membership and anybody can join. And I think because we had so many amazing people join in the beginning, and they became so evangelical about what we were doing that they would tell their friends who were like hearted. And we wound up just growing exponentially that way. One of the things that has also really evolved in the couple years that we’ve been running. The Outlier Project is people’s desire for face to face. So we do almost 200 live, interactive virtual events a year, which is a you know, insane amount of of events. And while I love those and I love the power to bring people together in that forum, there’s nothing like we do 14 in person events all around the country, everything from we just went to the US Open. We went to the Kentucky Derby. We have a big retreat in Rhode Island coming up. So we do a lot of really cool, fun stuff all over the country, and there’s just nothing like that. There’s nothing like the opportunity to see somebody face to face and give them a hug and and spend time with them in that type of an environment. So we’re going to continue to do that. And one of the cool things is that I’m at all of those 14 scheduled meetups, but our community has now taken the initiative to schedule their own meetups that you know, I can’t be everywhere every time. So we’re now doing tons and tons of meetups all over the country and really all over the world, initiated by our members. And I think it’s just such a powerful way to get together and, you know, help each other accomplish the things that we want to accomplish. Everybody wants to live an extraordinary life. Everybody wants to make that dash between the dates meaningful. We don’t want to sleep walk through life, and in order to do that, we need community and we need other people to lift us up, because not every day is a day where you feel like a million bucks, and that’s when you know you need to place those calls to your friends like Kara Goldin, and you need to say, hey, I need a helping hand today. And those friends are are priceless.

Kara Goldin 14:59
So grab. Attitude plays such a big role in your leadership approach, and how do you weave that into the outlier project? And, I mean, do you ever have people coming in who are not grateful, or who that you have to kind of wake them up in some way to get them focused on this. I mean, what do you see like? How do you teach that? I guess is the question. I think

Scott MacGregor 15:28
you lead by example. And I think when you do have people that maybe have more of a victim mindset, when they’re all of a sudden surrounded by people that understand that adversity is a gift, and they see things in a very different way, it slowly rubs off on those people. You know, if it’s one or two people, it doesn’t quite have that effect. But when you’re talking about 700 and something people that really view the world through a lens of gratitude, uh, it rubs off on nearly everybody, and they slowly become, you know, have less of a victim mindset and more gratitude. So, you know, it’s, it’s certainly, we bring a lot of people on that have unbelievable stories of resiliency and have overcome so many things in their life that it’s very hard to say, you know, it’s very hard to have a woe is me attitude when you’re constantly surrounded by people that have just overcome unbelievable odds to craft and create a an extraordinary life for themselves and their family and their friends. Oh, I

Kara Goldin 16:52
love that. So you invite leaders in to speak to the group often, but obviously you have leaders who are joining you for the as part of The Outlier Project too. Is there one lesson that you’ve that’s kind of completely shifted your perspective, that you’ve learned from somebody along the way, that really has kind of changed you personally, but also made you a better leader and somebody that you can teach that to other people too. I

Scott MacGregor 17:27
learned something from every single person we have on honestly, every person that we bring in, I learn something new, and sometimes it’s just perspective and mindset, and other times it’s more of a tactical business decision. I actually think I might have met this gentleman through you. Yuri Levine, so Yuri is absolutely amazing. Sold two companies for a billion dollars, one to Google, one to Intel. And you know, he was talking to our group, but he was talking about, you know, if you have a subscription business, which our community is essentially a subscription business, not software, but it’s a subscription business. He said, You really, you don’t want people to pay annually. You want people to pay monthly. And we were all kind of like, really, because you would think that you want the cash flow and you want that annual, you know, membership. And he said, No. And we asked, you know, why do you say that? And he said, feedback. Said, when you have people on a monthly subscription and they can cancel and they need to make a decision whether to renew or not every single month, your feedback loop gets really short, and you know whether you’re delivering value to them, and your ability to course correct when you’re not is so much greater versus if your annual you may not know for a year that you’re not providing the value. So it’s, you know, sometimes it’s those tactical business decisions that you learn from somebody like a Yuri Levine, and you go, man, I never really thought of it that way. So the fun part, for me, selfishly, and I’m sure for all of our members, is that there is always so much to learn. We’re all lifelong learners, and in some cases we’re in graduate school, and in other cases we’re in elementary school. It depends on the subject. And that’s the fun part. Is we get to learn every day from different people.

Kara Goldin 19:46
Yeah, definitely. Yuri is amazing. And to your point, so many people think like, oh, annual subscription cash flow, you know, but it’s also it’s cheaper to do it by by the month, and so it’s less likely. Quickly that you’re going to actually get people canceling too, but it’s that’s, that’s such a great insight. So he’s so smart. I mean, it’s everything that he’s so so smart and really enjoyable too. So and has helped me get from location one to location, or a to b or whatever. So through through ways. Yuri is the founder of ways. So, so if you could change one mindset that you think really holds people back, maybe you’ve seen this in your group from the new entries. I feel like even if we change, we sometimes we step back right and and we need to get a reset. And that’s another reason why The Outlier Project is so great. But what is that one, one mindset that you see in people that really, you need to shake them up and get them to to to change?

Scott MacGregor 20:59
It’s such a great question, I would say a victim mentality. And here’s the reason why I say it, I think a lot of people have a victim mentality, because being a victim is actually a real, really seductive thing. And the reason why I say that is, if you’re a victim, you don’t have to take responsibility, because you could say, Well, hey, it’s not me, it’s my boss, it’s my company, it’s the family I grew up in. It’s, you know, there, there’s all these excuses where you don’t have to take accountability. And I think your ability to live an extraordinary life, your ability to live a life of impact, is all around reframing the adversity in your life, to understand that adversity truly is a gift, and that in your worst moments, no matter what You’re going through, if you looked behind you at the line of people that would take your place at that moment, the line would be so long you’d never be able to see the end. So, you know, I would say, trying to get people to not be a victim and to take personal responsibility for their life, that the place you’re in right now has much more to do with the decisions and choices that you make than anything else. And you know, it’s why that that mantra that we have is so important. So you know, anyone can be ordinary, but we all have the power to choose to be extraordinary. The key word there is choose. So you get to choose to have an extraordinary life. And I think so many people think I need to be born with Michael Jordan’s DNA, or I had to be born a Kennedy or I had to be born with Steve Jobs brain to live an extraordinary life. And what I recognized by surrounding myself with extraordinary people that have written bestsellers, that have been Navy SEALs, that have run billion dollar companies, that have won Olympic gold medals, is they were. They’ll be the first people to tell you they weren’t the most athletically gifted. They probably weren’t the smartest person in the room, but the choices that they made and the people that they surrounded themselves with, led to them accomplishing extraordinary things and then living that fulfilled life, which is really what we all want.

Kara Goldin 23:52
Yeah, that’s so true. And I think you really nailed it in that last couple of sentences too. Is the the decision to to show up, but also to build the community that you aspire to be, right? I think that that’s an important piece of it that we want to you don’t always want to be, you know the highlight in the room, right? You want to be in a group where you’re going to be learning from people, where you’re going to be able to level up even that much more so, and that’s really what I see with the outlier project. So you mentioned books and authors. You have your standing O book series that is so terrific. So everybody should definitely check those out. Can you give people a little bit of a glimpse into those?

Scott MacGregor 24:40
Yeah, so I this is kind of an interesting story. So 10 years ago, I started a company called something new, and I was very, very passionate about giving back, but I will admit I am a absolute control freak, and I did not want to take any VC money, so I was going to bootstrap. The business. And so when you make the decision to bootstrap the business, you’re putting every penny that you make back into the business to keep it, you know, thriving. So I thought, oh, boy, what am I going to do? How am I going to give back to these organizations that I’m so passionate about? Because I’m investing all the money back into the business. And I thought, what are my assets? And my assets weren’t a giant bank account. My assets were the amazing people that I’ve developed beautiful relationships with over the years. So I thought, How do I leverage that asset? And so I asked 52 of my friends if they would write chapters of gratitude for a life lesson learned, and then I’d put them in a book, and I would give 100% of the proceeds to charity. So the first book was standing O and Dick Vermeil, who’s in the football hall of fame and coach the Rams to a Super Bowl, wrote the forward, and Tiki Barber, who’s a all time great running back from the New York Giants, wrote the cover quote. And then so I’ve written four of those books. I’ve been absolutely blessed that you’ve written a chapter in the standing O Series, and it’s just been a great way to highlight really great organizations that are doing great things, but also to be able to give them a check, because 100% of the proceeds for all the books go to charity, and Book number five will come out this year.

Kara Goldin 26:34
That’s awesome. Well, they’re so terrific. You can’t see them up there, but I have up on my shelf back here. So really great. But Scott MacGregor, thank you so much for coming on and sharing a lot more. We’ll have all the info in the show notes for the outlier project, for those who might be interested in learning a little bit more and joining but really appreciate everything that you’re doing. You were just a, you know, a shining, a North Star, I think, for so many people. So you’re not just a shining star, you’re a North Star. So really, really awesome

Scott MacGregor 27:11
you are. You’re a very, very special person. And I take so much inspiration from you and the career you’ve lived in. You are a true outlier. I mean, what you’ve done from, you know, going from Time magazine to CNN to AOL to oh, wait, you know, there’s a problem. I don’t want to drink sugary soda and juices. Let me do something that was really revolutionary. And starting hint, I mean, you’re such an inspiration to me, because you are a true outlier. So you know, thank you for giving me a platform to talk about something I’m pretty passionate about.

Kara Goldin 27:51
Thank you so much, and thank you everyone for listening. Goodbye for now, thanks again for listening to the Kara Goldin show. If you would please give us a review and feel free to share this podcast with others who would benefit. And of course, feel free to subscribe so you don’t miss a single episode of our podcast. Just a reminder that I can be found on all platforms. At Kara Goldin, I would love to hear from you too. So feel free to DM me, and if you want to hear more about my journey? I hope you will have a listen or pick up a copy of my Wall Street Journal, best selling book, undaunted, where I share more about my journey, including founding and building. Hint, we are here every Monday, Wednesday and Friday. Thanks for listening, and goodbye for now. Bye.

Click to subscribe:

Listen on Apple Podcasts
Listen OnApple Podcasts
Listen on Spotify
Listen OnSpotify
Listen on Overcast
Listen OnOvercast
Listen on PlayerFM
Listen OnPlayerFM

People Also Liked

617

David Bean: Founder & CEO of NIRA

616

Brianda Gonzalez : Founder & CEO of The New Bar

Mike Dunlop: Author of The Art of the Turnaround

614

Katie Lefkowitz: Founder & CEO of Harken Sweets

613

Erica Bethe Levin: Founder & CEO of Globowl