Friends with Benefits

Reinventing Yourself Through Every Season of Life with Jeff Gangemi

• Sam and Jason Yarborough • Season 3 • Episode 7

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There’s a certain clarity that comes from looking back and realizing every winding path was preparing you for who you are now. 

This week, we sit down with our friend Jeff Gangemi, someone we met by chance at B2BMX and somehow ended up adventuring through Montana, swapping stories in the woods, and weaving into our inner circle. Jeff’s lived a lot of lives: religion major, nonprofit guy, journalist, marketer, consultant, coach, dad, husband, traveler. His story is proof that reinvention isn’t always glamorous. Sometimes it’s messy and risky and full of unknowns, but still the thing you’re supposed to do.

We get into Jeff’s journey of curiosity-driven career pivots, his move from Vermont to Los Angeles with two small kids, the reinventions that paid off, and the one time he didn’t follow the itch and what that’s teaching him now. We also explore how he discovered men’s coaching, how breathwork reshaped the way he shows up in the world, and what it takes to grow with someone for 23 years without losing yourself along the way. If you’ve been feeling the pull toward “what’s next,” this conversation is exactly the kind of honest, grounded encouragement you need.


What you’ll learn:

  • Why curiosity is one of the most powerful career and life tools you can build
  • What real reinvention looks like, both the freedom and the discomfort of it
  • How coaching can shift the way you lead, relate, and step into the person you want to become


Jump into the conversation:

(00:00) Introduction

(01:13) The winding path that shaped Jeff’s story

(04:50) How curiosity became a compass

(08:45) When change shows up and asks for more

(13:28) The messy middle of reinvention

(21:32) How coaching shifted the way Jeff shows up

(28:51) Therapy, coaching, and knowing what you need

(30:10) Seeing potential in yourself and others

(35:13) Finding the people who help you grow

(40:37) Trying to build a life that actually works

(48:14) Raising kids, taking risks, and staying steady

(50:16) The books and ideas that keep us growing


Connect with Jeff Gangemi: https://www.linkedin.com/in/jeffreygangemi  

Check out Toptal: https://www.toptal.com/ 

Check out The 15 Commitments of Conscious Leadership: https://amzn.to/4oAUuSU 


Check out Arcadia: https://www.BeArcadia.com  

Connect with Sam Yarborough: https://www.linkedin.com/in/sam-yarborough/ 

Connect with Jason Yarborough: https://www.linkedin.com/in/yarby/ 


Produced in partnership with Share Your Genius

https://www.shareyourgenius.com 

[00:00:00] Jeff Gangemi: I’ve been driven by curiosity, you might say novelty seeking in some instances, variety seeking. There’s a light side and a shadow side to that. Even in places and times where it made sense to stick around and to build roots or allow roots to grow, you might say I was driven to continue to go pursue the next thing.

[00:00:34] Jason Yarborough: Welcome to the Friends With Benefits podcast, an Arcadia production. This is the show all about how to grow in business, lead with purpose, and live with intention. We are your co-hosting couple. I’m Jason.

[00:00:46] Sam Yarborough: And I’m Sam. Welcome to the show Friends. Today’s guest

[00:00:51] Jason Yarborough: Is great.

[00:00:52] Sam Yarborough: Is so great. I loved this conversation. You actually met him first at B2B MX.

[00:00:57] Jason Yarborough: Yeah. He was kind of one of those guys that you meet and you just instantly connect with somebody you instantly want to be friends with and figure out a way to get him involved in everything that you’re doing.

[00:01:06] Sam Yarborough: And he also came to the Arcadia leadership experience this year, which is where I got to get to know him a little bit better. We’re talking about Mr. Jeff Gangemi,

[00:01:15] Jason Yarborough: Jeff the great one Gangemi.

[00:01:18] Sam Yarborough: He currently is at Toptal.

[00:01:20] Jason Yarborough: Yeah, practice director. So he is doing some big stuff. He’s got a great podcast there as well.

[00:01:24] Sam Yarborough: He sure does. This conversation, we talk a lot about a myriad of things. You take a little bit of a winding trail. He’s also a coach, he’s a dad, he’s a devout husband. He’s traveled the world many times with his family and taken some leaps that didn’t necessarily feel safe but necessary.

[00:01:42] Jason Yarborough: Again, one of those guys you just instantly want to connect with and get to know.

[00:01:46] Sam Yarborough: Yep. So I hope you enjoy today’s conversation and we’ll see you next time Friends.

[00:01:52] Jason Yarborough: See you out there. Howdy. What’s happening? Good to see everyone.

[00:01:56] Sam Yarborough: Hi everybody.

[00:01:56] Jason Yarborough: It’s always fun when we get a podcast and we actually have a friend that’s joining us. Sometimes we get people that we’re just meeting because of the podcast or some people we’ve crossed paths with. But this week we’ve got Jeff Gangemi, who is actually a friend, right? He’s got some really great benefits we’re going to talk about today. But Jeff, welcome to our podcast studio room.

[00:02:19] Jeff Gangemi: I’m so pleased to be here. Thanks for having me. I want to be a friend. I am a friend to both of you, to Arcadia, to your vibes, etcetera.

[00:02:28] Jason Yarborough: Yeah, you fit the mold perfectly and it’s been a fun arc. Jeff and I just happened to meet each other at B2B MX last year, February, and then got to hanging out with Michael Ingram and Kate Delia, who is also some friends and all three of you guys were all at Arcadia this summer. So we’ve gone from just kind of casually meeting at a conference to hanging out in Montana together and now being a part of a community together and all the things.

[00:02:52] Sam Yarborough: That’s the dream.

[00:02:54] Jeff Gangemi: Yep. It changed my trajectory honestly, when I met you and the crew that met at B2B marketing exchange. I didn’t realize there could be an alignment of personal and professional in the ways that have happened since and I’m just really grateful for it. So thanks for being who you are and having me.

[00:03:13] Sam Yarborough: Will you say more about that, Jeff? I’m just so curious about how that has happened for you.

[00:03:19] Jeff Gangemi: Why now and why? How did I not know that this in this way was possible? It was every time I looked to my right at that conference, Michael Ingram was sitting there. Little did I know that he had scoped me out and done the background research on who I was and he wanted to talk to someone. We had very similar models of our business. His In-Tandem business does for RevOps what Toptal and my job does for marketing, it’s kind of like a freelance talent marketplace. Anyway, it wasn’t just that though. Even if he had done the recon and understood who I was and that there was potentially some synergy and partnership possibility there, great. But it was also a blast to hang out with him and he was really free with introducing me to people like Aaron Leader and Urb. And when I heard you start talking about ALX and the way your interests were in leadership, outdoors, partnerships, men’s work, growth on a personal and professional level, greatness, however you define that. Under Arcadia, I was thinking, is there any chance I’m going to get to Montana this summer for work? And I was like, hell, the chances seem so slim. And the fact that it lined up feels just like a—

[00:04:38] Jason Yarborough: It was meant to be. I remember meeting and having similar conversations around your coaching and what you were doing and things we’re going to talk about here and just a natural alignment. So we’re grateful to have you here.

[00:04:47] Sam Yarborough: Well, let’s dive in because for those of you that don’t know Jeff, he’s had many lives in his career. There’s a story behind each, but just to catch people up, we’ve had a religion major, you’ve worked in nonprofit, you’ve done journalism, you’ve done marketing, you’ve done agency stuff, you’ve done a lot. So as you kind of take a step back and look through all of those, is there a through line you can see now through your career that maybe wasn’t obvious in the moment?

[00:05:23] Jeff Gangemi: That’s such a good question. I gravitating toward aliveness and what feels interesting and putting different pieces together. I gravitated towards studying religion because I was interested in culture, I was interested in history, I was interested in spirituality, I was interested in politics, and it was one of the only studies I knew that brought all those things together. Economics, fill in the blank, just movement of humans, anthropology, people around the world. What’s the driver of human behavior? So I guess in a big way, it’s putting those earnest levels of interest and curiosity really about humans and the ways humans grow and develop and behave. And then, yeah, so same with nonprofit work, same with journalism, same with asking questions, trying to understand people. For me, when I got into journalism, I had an internship and a job at National Geographic Adventure, which was magical at the time.

[00:06:29] Jeff Gangemi: It was adventure travel sounds like the coolest thing in the world. It was less interesting to me than the work I ended up getting at Business Week magazine where I got to speak with entrepreneurs about what they were most passionate about. And then I saw business was another way of another intersection of a lot of those elements that I talked about with religion, strangely enough, economics, the way it impacts human behavior, movement of peoples and politics, etcetera, etcetera. And so for me it’s following that kind of curiosity into these kind of intersecting areas of human development and behavior, I guess.

[00:07:14] Jason Yarborough: I love this because I feel like we are more of the same person than I even realized. I put a post at about this on LinkedIn not too long ago, but I feel like we followed the same journey. Most people dunno this, but my degree is in theology. I’ve had a whole career in sales, a whole career in marketing, a whole career now in tech partnerships. Were you also a motivational speaker? Did I read in that same post? I was, yeah, that’s—

[00:07:40] Sam Yarborough: And a high school mascot. Let’s just throw that one in here.

[00:07:43] Jeff Gangemi: My Shannon was her, my high school mascot. My wife Shannon, who she was her high school mascot. See, there’s a lot of overlaps here.

[00:07:51] Jason Yarborough: And I was just looking for a book—Range. I’m not sure if you’ve read that book or not, David Epstein maybe. But it makes a case around people that are specialists and one specific thing. Those boring people who’ve only had one job in their entire career—

[00:08:05] Sam Yarborough: They’re not boring. Okay—

[00:08:07] Jason Yarborough: I’m just kidding. Just kidding. Frank, if you’ve had one job, dad, it’s cool. Versus those people that are generalists who have done many facets of things and lived many lives. We have. I don’t know about you and I’d love to hear your take on this, but especially in the work that I do in the partnership world, and Sam, you as well. I feel like that gives me kind of an edge in the work that I do and the many different types of conversations and departments and teams I’ve got to work with. How does that generalist background tend to work out for you as far as an edge goes or maybe not an edge?

[00:08:44] Jeff Gangemi: I think that’s a really good question. I’m interested in that. And for me, I really think about it as kind of that curiosity piece in the world of marketing, honestly. Can you really talk to people and connect with people and start to understand their underlying motivations and behavior? That’s the thing, that’s a general, that’s a skill that literally applies all day every day. And for me, the journalistic set of skills is a really important one that I didn’t know. I was developing actually during college when I was studying abroad and in Northern India and Tibet and Nepal, and sitting with people from different cultures, from a curious perspective and being able to pull that together into some kind of a meaningful product or a synopsis or a synthesis of what I was gathering. To me, that’s what my generalist orientation enables. And then I really formed that consciously and more specifically as a journalist. So that question asking again, the real curiosity, the probing into what other people’s interests are. This right now talking about myself is something I have done a lot less of. I’m often the one asking questions. I even host the Toptal Executive Guidance podcast where I work now. But that set of skills for me has been formative and I really think overall is the bedrock of, I guess what would you call it, an advantage or a leg up or a—

[00:10:21] Jason Yarborough: Yeah, an edge advantage.

[00:10:23] Jason Yarborough: And I do want to maybe take a second to drill into that word curiosity you mentioned there, and I think the edge there is the curiosity, and we’ve kind of been chasing this rabbit that feels like uncatchable to me, but I’d love to hear your take on is like do you believe that you can teach curiosity? And if you believe that, how can we teach? Or what I’m trying to figure out is how do we coach the curiosity, especially people that are kind of younger in their careers trying to figure this out and may not know what they can do or those are even established in their career. But I feel like curiosity is an edge that a lot of folks just don’t lead from.

[00:11:01] Jeff Gangemi: Curiosity. So I’d make two points on that. I think the first one is there’s a tuning in process that’s hard to do probably in the modern world and probably for young people in general that kind of allowing themselves to be guided into what is pulling them or drawing them and their different levels of their interest, I guess. And so tapping into that and getting into the flow of what that feels like is something that that’s what I appreciated about liberal arts. I didn’t have to take all these prerequisite courses. I just literally could take what I wanted in college, for instance, and then that’s kind of a muscle that got built, and so I was more easily maybe able to follow that. And then the other thing in journalism and why I felt so lucky to have that experience was I got to ask, and that’s what we all talk.

[00:11:53] Jeff Gangemi: We are entrepreneurs to some extent, or we talked with a lot of entrepreneurs or people that are really passionate entrepreneurs. When you get to interview them as a writer and they know they’re going to be published for something that’s going to help promote their business, that’s one thing. But you’re literally talking to them about the single thing that they are most passionate about in the world and how can you not be curious about that when someone is demonstrating that level of passion. So that’s I think one is that tuning in process that is a muscle that you can develop. And then the other is talk to people about what they’re most passionate about and you cannot help but come alive and be inspired and become more curious about how to get more of that for yourself.

[00:12:33] Sam Yarborough: I think you’re spot on there. Generally people like to talk about themselves and what they’re excited about. So I think that becoming good at asking questions and that starts with being a good listener is huge in that curiosity realm. Going back to, I’m not going to phrase this the same exact way that you did, but tuning in, the process of tuning in. So in your process of reinventing yourself many times throughout your career, how did you know it was time to move on to the next thing? Was that intentional? Were you following curiosity? What did that process look like for maybe somebody who’s listening that’s like, man, I’m in a moment of reinvention. Am I doing this right? How did that feel for you?

[00:13:21] Jeff Gangemi: It’s funny that you use the term process with somebody like me who is not the most process oriented because it hasn’t been driven by curiosity, you might say novelty seeking in some instances, variety seeking, and there’s a certain amount of that that there’s a light side and a shadow side to that Sam, where we’ve moved a lot. I’ve been even in places and times where it made sense to stick around and to build roots or allow roots to grow, you might say. I was driven to continue to go pursue the next thing. For instance, we were in Vermont for seven years. That’s where we had our babies and quite well connected, had a good place to live, and it was just about to be the time where the girls, my two girls were about to go into school and we would no doubt have created an even deeper community. And part of it was being in, working from home underground with not a lot of light and needing that. But I basically uprooted our family and made us move to Los Angeles from Vermont. People were looking at us like we’re crazy. That not a process, Jason, Sam, that comes from somewhere else that’s not coming.

[00:14:42] Jason Yarborough: That’s following that curiosity, man. For me, it’s like I describe it as I get this itch or this feeling, or you can almost describe it as a calling, that there’s a change coming, that something needs to happen. And it’s very funny, you mentioned seven years. I feel like for me that happens in seven year increments. If I look back at my career and how it’s changed, it’s like every seven years is when you start to feel that change.

[00:15:07] Sam Yarborough: I also like this story because every time I’ve had a quote itch or something like that, it’s so inconvenient.

[00:15:14] Jeff Gangemi: I can’t imagine something more inconvenient than needing to move from with literally a five-year-old and a two-year-old in a comfortable house. I mean, we were in Vermont, we packed them up in a minivan, took 10 days and drove across the country, stopped at Carlsbad Caverns, stopped in Zion National Park where we discovered there was lice. There were lice in the car. So the picking up and the moving on. And then we had to live in a place in the middle of LA, which we’d never spent more than a week or so in a rental that didn’t have washing machine and dryer with trying to—it’s not always a pretty reinvention. It’s painful. It’s a challenge. It’s an adventure and adventure. It does not imply only excitement. It implies risk and pain as well as excitement.

[00:16:08] Sam Yarborough: It’s not always fun and glorious,

[00:16:10] Jeff Gangemi: Not always fun and glorious. Yeah, no great advice there for people considering the career move. I don’t know if that’s what you’re looking for, but yeah.

[00:16:19] Sam Yarborough: No, I do love that because I think the honesty around that is really important. We can look at the high arc of somebody’s life and be like, wow, they’ve reinvented themselves a million times. That sounds lovely. And in hindsight it probably is, but in those moments it’s not sometimes a logical decision or a step A to B process and you don’t know what’s on the other side of that, but there’s something inside of you that you can’t ignore. And I think that that’s a conversation that doesn’t happen often.

[00:16:53] Jeff Gangemi: That’s why I’m so proud of what you’re going through, by the way, about Sam. I know Sam’s in that moment of formation of what’s next. Maybe a glamping company, maybe a CEO role of—who knows what’s next. But CEO of Arcadia, I mean for me happening, that’s incredibly meaningful in itself.

[00:17:14] Jason Yarborough: And I think for all that you’ve really got to be okay with risk and being able to step out and take that risk. But the beautiful thing about that and what I’ve experienced is that I think the more you follow those urges or callings and you take a risk and you step out and you make it work, you get proof that you can do this. And what happens, what follows proof is confidence. You get confidence on yourself, your ability and what you can go do and figure out. And you begin to build this life and this career that you’ve kind of followed just based off curiosity. But over time you build this life of confidence and ability to go do whatever the hell you want to go do.

[00:17:54] Jeff Gangemi: Resilience too. Resilience for oneself and also for kids, for those kids to have to figure out how to adapt from being outside and twenty-degree weather and very nature-based experience in Vermont at the school to wait a minute, you can’t have bare feet there. Literally, we’re living in Hollywood. We moved to the heart of Hollywood. And the resilience of needing to understand and adapt to new deeply, deeply new and different circumstances is something that builds what you’re talking about, Jason, I think a hundred percent.

[00:18:34] Jason Yarborough: And it’s something that kids these days definitely need.

[00:18:37] Sam Yarborough: Yes. I would be remiss not to ask this question, but two things. One, I feel like I just saw somebody post about this fear—FOSO is what they’re calling it, fear of starting over, which I think is a very interesting concept. And as adults, as we move, as we progress in our life, our risk tolerance becomes a lot less. So I think this story is really helpful for people because you can start over. B, you will survive the other side of it. And I think we tell ourselves these stories of comfort: I can’t, this, that and the other thing. And those are all just stories we tell ourselves. In truth. Jeff, has there ever been a time in your life where you had an itch and you didn’t follow it?

[00:19:30] Jeff Gangemi: Just now, just in the last few months actually. So it’s funny because we ended up—pandemic hit when we were in Los Angeles and we decided we needed to come back east, spend a few months in Costa Rica and had a cool experience on the way back. But deep family roots, especially for my wife Shannon here. She’s twenty-some cousins and aunts and uncles, and we’re living where I’ve come for over twenty years to visit. And then we’ve moved here and it seemed like the assimilation or the integration into a place like this would be smooth and simple, especially compared to somewhere like Los Angeles, where for me that was—I was alive. Every experience was new. You could go to the desert on the weekend and go surfing at a beautiful surf break. You could do so many different things culturally. And it was endless. Here, it was subtlety, nuance, who are we going to connect with? How is this going to work out? And I found myself after three or four years thinking, I’m out. I’m ready. I believe I’ve given this the chance that I’d always considered or thought I would need to give it and I was ready to be out. And I feel like that was a bit of the shadow of that seeking that I’ve had previously. And it was okay and good and part of my journey to do that a bunch of times like we have done. But this time, once I made that decision just a couple months ago, literally not to pursue that next thing, even though we’re doing a thing in Spain for a few months as you know, which should be really cool and scratch that itch in a way where, okay, we’ll be back in three months. Here we are, we’re still going to commit to this place. It’s harder for me to not do that. So this is the growth for me now, which is staying put instead of doing another reinvention, if that makes sense.

[00:21:28] Jason Yarborough: Is that time of not wanting to do this, not wanting to be here, is that kind of what led you to coaching? And I know we’ve talked a lot about this in our conversations and in Arcadia, and you mentioned you kind of got to that point where you said, okay, I need help. And was that part of what led you to coaching or is it more than that?

[00:21:51] Jeff Gangemi: The coaching thing, it’s a funny story because it wasn’t as conscious. Again, I wish I could say—

[00:21:58] Sam Yarborough: Nothing ever is. It just looks like it. In hindsight for some—

[00:22:00] Jeff Gangemi: For some people I think it may be a little bit more, or at least I assume it is anyway. Maybe it’s not. But for me it was actually in LA and we were getting ready to leave and there was something that felt—I have some degree of anxiety as a lot of people do, even if I don’t present in that way. And that has presented in kind of grumpiness and moodiness and agitation and just I think partially that need to continue to reinvent and move. I’d written an article for my business school alumni magazine about podcasting and different podcasts. I was listening to this podcast of a guy that I’d interviewed and it autoplayed from him interviewing Matthew McConaughey into this coach that I hadn’t really thought about coaching and I heard this voice. I think there were wildfires outside, so we were kind of locked down inside. There wasn’t much to do. Maybe it was even over the Christmas break that year and we weren’t coming back east. Anyway, I heard somebody speak to me in a way that I hadn’t understood. It felt like a serendipity or a deeper calling. And that was the coach that I ended up working with for about two years.

[00:23:16] Sam Yarborough: The one you heard on the podcast?

[00:23:18] Jeff Gangemi: Yeah, the one I heard on the podcast. I just reached out and I said, there’s something here I’m interested. I ended up interviewing a couple of coaches. I couldn’t just go with the first guy I heard, of course. I didn’t put out an RFP or anything, but I needed to make sure I was not insane.

[00:23:36] Jason Yarborough: Finding the right one.

[00:23:38] Jeff Gangemi: But he asked for more money than I ever thought I would be paying for this work. And it was the most powerful work moment to moment.

[00:23:49] Jason Yarborough: I like the way you phrase it and then how you said it completely changed how you show up in life. Can you tell us a little bit more about that for folks that may not know about coaching or kind of are like, yeah, coaching’s cool, everybody’s a coach these days, whatever. But for you, how did it actually change the way you show up in life?

[00:24:09] Jeff Gangemi: This was a very particular type of coaching and he’s a men’s coach. It was very oriented toward men and men’s development. Coaching can be across the spectrum and it can be so many different things to so many different people. So that’s the qualifier. This particular experience for me was addressing fears, moment to moment fears really. It started with a lot of breath type work and we didn’t do breath work as in the kind of breath work that my wife now does, which is a thirty to forty-five minute, very active, intense, almost psychedelic experience. This was breath holds we started with. He was sitting with me, pushing me to continue coming back to myself in the midst of a fear. It is a truly human animal fear. When you run out of breath, your body is saying—

[00:25:04] Sam Yarborough: You’re going to die.

[00:25:05] Jeff Gangemi: It’s a physical reaction, right? You’re going to die if you don’t breathe. So developing a higher level of comfort in those periods of discomfort starting physically and then moving into emotional spheres and relationship, that’s what it’s all about. Because these different ups and downs and emotional states and all sorts of different states are going to come your way and how are you able to stay calm in that circumstance? And even he taught me how to sit in the way I’m sitting now, which is—I had not been a client facing person at work. I was in internal marketing teams for fifteen years or so, ended up getting a job as a consultant with Accenture as a strategist. So basically running all the calls with these big clients. And the way he helped me learn to sit in this particular posture, which is with more open chest—it was incredible to see the way people changed in the reactions that I would receive from people in my ability to command, not in a military command and control kind of way, but in a kind of confident, assertive, present sort of way. It was really powerful. So yeah, it changed a lot of the ways I show up and those are kind of just the beginning around this coaching journey. And then I ended up obviously doing a training over about a year and a half to become a certified integral coach myself. And that was more recently.

[00:26:31] Jason Yarborough: That’s awesome. And you’re doing men’s coaching now, correct?

[00:26:36] Jeff Gangemi: That’s right. On the side, just a couple of clients on the side. Obviously I have this day job and some responsibilities here and there.

[00:26:45] Jason Yarborough: What’s the thing people think coaching is versus what it actually is?

[00:26:49] Jeff Gangemi: I think it’s very common to assume that there’s going to be demonstrable, sustained progress—can you see my air quotes?—that you’re not going to take steps back, that you’re not going to pursue this kind of spiraling, revisiting of a lot of the same issues over and over a span of time. A coach can say, hey, we’re going to work together for six months. Every other week we’re going to meet. A coach has to sell to some extent to get the person in the door and really believing in their capacity for change or transformation. But I think what it often really is and what enables a lot of that transformation aside from some of that really powerful intense practices—which I think there’s lots of different kinds of coaching. For me that is critical to do kind of breath oriented work, because it can be such an enabler of state change and nervous system regulation. To me that’s really important. But I think often what coaching is and what enables change is just having somebody provide another set of eyes to identify new opportunities and new potential shifts that you can make in your course and in your path and just be there side by side with you.

[00:28:05] Jason Yarborough: For me, I reach out to a coach—that’s always in high school, college—and I had a running coach. I understand what a coach is there to do and help you see, all right, here’s the mechanics you’re not getting right, here’s what you’re not doing. So when I found my coach, I was like, hey, I need a coach who can help me identify my blind spots. I know I’m trying to get to a different level than where I’m at now. I’m having a hard time getting there and I know there’s some things that I’m not thinking through, some blind spots. And then there’s some things with myself I need to kind of walk through and talk through. So helping somebody basically clear the path for me and show me the—quote, there’s my air quotes—mechanics of how to improve in this life.

[00:28:46] Sam Yarborough: To go even further, I think people are like, okay, we’ve heard of coaching. The question between what’s the difference between a coach and a therapist? So let’s start there and then I have a follow up question.

[00:28:57] Jeff Gangemi: Oh yeah, there’s a lot. Much ink has been spilled on this question. I think a shorthand—one fundamental difference is therapy often focuses on unpacking the past and often traumatic experiences or developmental experiences. In the past, coaching tends to be more of a present and future oriented practice. So where are you now? What are the options available to you here and now? What are the behaviors available to you now and what are the possibilities associated with that? So to me it’s empowering. I think there’s a place for both. I did therapy, not so much recently, but definitely at various points for periods of time, Freudian and otherwise, with a great person in New York back in the day. But that’s a big difference for me. And there’s many ways to look at it, but that’s a shorthand that I’ve often found useful.

[00:29:55] Jason Yarborough: That’s a good way to look at it.

[00:29:57] Sam Yarborough: And this is going to be different for everybody. I completely understand that. But you joked about not sending out an RFP for a coach. I actually think we should start a business for that. You should—

[00:30:08] Jeff Gangemi: You’d be—yeah. I want you to do everything. You guys are so good together for one. And Sam, your executive level function is just like way up there. That’s why I think we were laughing about this glamping business. You could do it. We were talking yesterday in the cohort discussion too. You could definitely do so many different things. I’m so excited for you to find the thing that lights you up in the way—

[00:30:34] Jason Yarborough: We talk about a lot of things.

[00:30:36] Jeff Gangemi: I’m sure you do. There’s so much possibility when you have someone who’s so multi-talented, who has this applicable set of skills and empowering others in pursuit of these kinds of goals as you have. It’s pretty cool.

[00:30:51] Sam Yarborough: Well, that’s the end of the podcast, ladies—

[00:30:54] Jeff Gangemi: Thanks for listening and Sam’s great and yeah, you guys are great.

[00:30:58] Sam Yarborough: Well thank you for that. I’m curious, in your opinion, are there characteristics that are a must for a coach? If somebody’s pursuing this and sending out an RFP for coaches, what do they need to look for in this individual?

[00:31:15] Jeff Gangemi: To find a coach for themselves? Oh, I understand. Okay. Wow, that’s a really hard question. I think—I just walked you through my experience, which is full intuition and totally—the guy, he showed up. He just happened to appear in this podcast after Matthew McConaughey. Like what? This is not a high—

[00:31:37] Sam Yarborough: Say less.

[00:31:38] Jeff Gangemi: Right? There is this intuitive type of connection that you have with somebody that I think there’s a balance that occurs where there’s a sense of—I don’t want to say comfort, but understanding. Or that there’s this connection there that’s a little bit deeper potentially than just a regular connection, but also that you have this sense that it’s not just comfort, that there is something about this person that is willing to hold you to a higher standard than you would be able to—what Jason said before, identifying the blind spots and not just calling them out, but identifying how to more consistently bring them into the light and achieve something new by using those in skillful ways. So another shorthand way is someone that’s going to call you out and call you up to a higher level that feels challenging in some way.

[00:32:34] Jason Yarborough: And someone who can help navigate that journey to that place as well.

[00:32:38] Sam Yarborough: And to your point, Jeff, yeah, I mean that looks different for every person. The way that I’m called to a higher place is different than Jason, but I think having that intuition around that is a good callout.

[00:32:51] Jeff Gangemi: And one thing I do want to talk about around coaching is really interesting because for me—or something I’ve encountered a lot—which is in sports for instance, Jason, if you’re having a football coach or a running coach or someone, you’re assuming that’s someone who’s been down that path before and has an intimate understanding of methodology or technique or something like that. Particularly we’re talking physical. In the coaching space, if you are struggling in relationship for instance, or if you’re struggling in career or professional development, I think there’s a benefit to having someone that has been there that you can look up to and has a demonstrated track record of succeeding on some level of what is meaningful to you. I think there’s value in that. At the same time, no one can be amazing at everything and no one can have had all the experiences. No one is a guru. I mean you can be a guru kind of, but it’s not that person is going to eventually come down from that pedestal. So I think being honest with yourself about which areas of their life are most important for you to really aspire to and which you’re okay with having them just have a presence and a coaching ability generally, as opposed to that specific set of knowledge, if that makes sense.

[00:34:10] Jason Yarborough: Yep, a hundred percent. I actually found my coach—I reached out to get this guy’s boss on our podcast and we had a couple of conversations and we started talking. I was training for a big race here in Bozeman and he was coming out for a big race in Big Sky not long after. And we started talking about performance and running. He mentioned he was doing some coaching and I was like, this is wild. I know I was trying to get your boss on our podcast, but do you have any slots available for coaching? I was like, I really want to work with you.

[00:34:43] Jeff Gangemi: And are you working with him?

[00:34:45] Jason Yarborough: Yeah, that’s the guy I’m working with now.

[00:34:47] Jeff Gangemi: That’s the guy you’re working with. There you go.

[00:34:49] Jason Yarborough: I like him. He’s been a great coach. So yeah, go get a coach if you’re listening. Couldn’t recommend it enough.

[00:34:55] Jeff Gangemi: Or chat with some people. I think that’s the thing that people often worry about: am I going to get roped in? I don’t think it’s like that. I think there’s a process you can really openly go through and just feel people out. And there’s value in that too because you get some different perspectives.

[00:35:14] Jason Yarborough: Let’s jump into talking about some communities. You and I are both a part of a few together. You’ve joined some really intentional communities, like the men’s group you mentioned earlier, some professional groups. I know you’re a part of ours and growth communities. So for you, what’s been the driving factor in first seeking these communities and groups out and secondly joining them?

[00:35:33] Jeff Gangemi: The epidemic of loneliness, people feeling separate. I’ve worked from home now for fifteen years or more—like a ridiculous amount of time. I was kind of on the early side. Tim Ferriss came out with The Four-Hour Workweek and he was preaching this thing. I didn’t even know about him and I was in Argentina in early 2007, working remotely as a journalist, halftime using a Vonage voiceover IP, really shoddy, very terrible internet connection, but getting it done and making it happen. I’ve been working remotely for a very, very long time. So the desire for deeper connection and community has been consistent over the years, and I’ve gotten it in different ways. Went to business school, lived in different places. But the more intentional communities recently—the first one was this men’s group that came as an offshoot of that coaching relationship. The coach I had formed a men’s group, which was really meaningful and useful and a really strong continuation of the work we were doing together. Doing it in community with other men facing some of the same challenges was really powerful and useful. There was a retreat in the mountains in Colorado that was part of that too, which was a vital, really, really powerful part of that experience. And then more recently, Arcadia for me. The experience of the self-selection of the people who are willing to be outside and camp and have every session of a conference be under a tent or physically outside is such a perfect blend. It’s—

[00:37:10] Sam Yarborough: It’s an equalizer.

[00:37:11] Jeff Gangemi: It’s an equalizer. And I’ve just wanted that for so long—that why does everything have to be so compartmentalized? So a community that truly embraces it, it was equally possible to stumble into a conversation, have people talking about something deeply personal or partnership, go-to-market stuff. And I thought that was really amazing. And then Pavilion was part of those connections we made at B2B Market Exchange, which feels so long ago because that’s been so useful and meaningful and really just fun to build this network of people through that community too.

[00:37:49] Jason Yarborough: As someone who intentionally seeks out community, how do you personally get a lot out of the communities? I talk to a lot of people that join communities, whether it’s Pavilion, any of the others out there, ours, or whatever. It’s like, how do you personally get the most out of these communities that you intentionally join?

[00:38:07] Jeff Gangemi: I think it’s been just out of need, honestly. In the same way that I found my first coach out of a need, there was just something that wasn’t right or there was a need for some other type of experience for me. I joined Pavilion not to just be in a Slack group. It was, I’m going to go to some dinners in New York City. I’m going to go to their events and show up and feel uncomfortable and get exhausted from meeting a thousand new people, but have that understanding—and again, it feels like need for me a lot of times—to make a few really close connections out of that. So I think it’s an understanding that you’re going to meet 50, 60 people at an Arcadia leadership experience, but probably come away with six or eight or ten or twelve really meaningful interactions that can impact your life as you go. And that has happened. And so maybe, yeah, I guess I hadn’t thought about it that way, but maybe that’s—

[00:39:07] Sam Yarborough: Jeff, would you consider yourself an introvert or an extrovert or both?

[00:39:11] Jeff Gangemi: I’m right in the middle.

[00:39:12] Sam Yarborough: Okay. Okay.

[00:39:14] Jeff Gangemi: I’m definitely energized by people, which is the definition of an extrovert, but also there’s a limit. And I like to go to bed early and I’m not the guy staying up late and feeling energized to the extent of long nights.

[00:39:28] Sam Yarborough: You just described me to a T.

[00:39:31] Jeff Gangemi: T. The long nights or the go to sleep early?

[00:39:33] Sam Yarborough: No, no. 9:00 PM is my dream world.

[00:39:38] Jeff Gangemi: Me too. Me too.

[00:39:41] Sam Yarborough: Yeah.

[00:39:41] Jeff Gangemi: So would you consider yourself in that middle zone too then?

[00:39:44] Sam Yarborough: I would. Yeah. I need people. I thrive off of those interactions. I know it’s really important, but I also need time to just be by myself.

[00:39:56] Jason Yarborough: Just throw me in a room full of people and just leave me there for all opportunity—

[00:40:00] Sam Yarborough: Lock the door. He never has to—extrovert. Is that true?

[00:40:04] Jeff Gangemi: That’s great. That’s amazing. You say that’s true?

[00:40:06] Sam Yarborough: I think that’s pretty true. Yeah. You don’t really ever recharge.

[00:40:13] Jeff Gangemi: Wow.

[00:40:13] Sam Yarborough: Yeah.

[00:40:14] Jeff Gangemi: 5:00 AM pickleball, all that, right? That’s your style.

[00:40:18] Sam Yarborough: You’re spot on, Jeff. He would go from 5:00 AM to 12:00 PM if the opportunity was there. I’ve actually left him at parties and been like, you can get an Uber home. I’m leaving.

[00:40:30] Jason Yarborough: This is true. And at conferences.

[00:40:32] Sam Yarborough: And at conferences. Yeah. Okay. I want to touch on this. I think you’ve walked us through high level because we’ve only been talking for forty minutes or so, but you’ve been through a lot of transitions in your life. You have kids, you’ve moved a ton. There’s been career changes, but through that you have been with the same person for twenty-three years, which is rare. It’s amazing. Congratulations. Shannon’s phenomenal. So you—

[00:41:05] Jeff Gangemi: I don’t know if she’d feel congratulations are in order for her, but depends on the day, depends on the week, depends on the year.

[00:41:15] Sam Yarborough: So talk about that. What have you learned about growing with somebody? Because Jason and I were literally having this conversation this morning. We have some friends who appear to be growing apart rather than together. What have you learned about this and how do you grow with somebody?

[00:41:32] Jeff Gangemi: It reminds me of something we talked about earlier in this conversation. That’s the unexpected piece, which is painfully—growth and development, transformation and change come with challenge and pain. And I hate to lead with that. That makes it feel like it’s all challenge and pain. It’s not. It’s amazing. I mean, I am just completely fortunate. But we met very early, right after college—twenty-two. We got together right around twenty-three. And so that’s a lot of change. That’s a lot of growing up to do together. And a lot of—if you are committed to continuing to grow, you can’t be perfectly parallel together the whole time. It just doesn’t really work that way. But often we tried to be committed on that level.

[00:42:21] Jason Yarborough: I mean, it’s almost like a muscle, right? It’s like there’s a lot of—when you’re working out, there’s a lot of stress and rest that equals that growth. Any sort of performance model has stress plus rest equals growth. And I think in any relationship at all, there’s these stressful times, but how do you take the stressful times and come back to each other to recover, recharge, grow, figure things out? Stress could be anything. It doesn’t have to be a major life-altering, stressful event. It could just be minor stress here and there—growing the business, having kids, raising a family. But how do you manage that stress together, come back together, recover, recharge, and continue going? You continue to grow the more that you come back to and from that stress.

[00:43:10] Jeff Gangemi: I think that what you described is common almost to pretty much every relationship. But then there’s the long term—who are you? Is there a reinvention? There’s saying that you’re—everyone gets married three times. Sometimes it’s with the same person or whatever, or you married three different people. There’s something like that. Yeah. So what you described is real. It’s true. It’s hard to sit through that and work that muscle, but it’s totally worth it. I mean, it’s just worth it on every single level. So I started with the—it’s pain. It’s just pain and misery. But it’s like everything challenging, it’s growth and magnificence and the best moments and the best experience and everything. I want my life to be.

[00:43:57] Jason Yarborough: Completely. I think most people probably get it wrong and they sit in that pain, they sit in that stress and they don’t come together, own it. They try to deal with it individually or they just don’t talk about it or they just kind of stay in that particular zone and don’t try to move around it or bring someone into it with them—with their partner or relationship or whatever. And it just begins to take over their life.

[00:44:20] Jeff Gangemi: And there’s an expectation that maybe it should be easier or it should be—if it’s so hard, is it worth it? And I think it depends on the relationship.

[00:44:28] Sam Yarborough: Do you have any—I’m curious about this because I mean, there’s so much to talk through here. The reinvention—

[00:44:35] Jeff Gangemi: This could be many hours of conversation.

[00:44:37] Sam Yarborough: Yeah. I mean, just from this conversation alone, it’s very clear that you are somebody who prioritizes and seeks out personal growth. I would assume the same of Shannon and—

[00:44:50] Jeff Gangemi: Oh yeah. Oh boy. Yeah.

[00:44:53] Sam Yarborough: As you’re talking through this, you just showed your hands of like—that’s impossible to move in parallel over twenty-three years—

[00:45:03] Jeff Gangemi: At all times. I was—

[00:45:04] Sam Yarborough: At all times. Yeah. I mean there’s going to be times when you are doing something and she’s not and vice versa. And do you have any, or have you created any rituals to meet in the middle and kind of bring each other along on that journey?

[00:45:18] Jeff Gangemi: One ritual is an annual trip to the woods. We go to Maine in the summers. There’s a cabin that my great grandfather built in the woods in Maine on the lake. And that feels like a coming together where there’s a lot of slow walks. It’s an extremely slow pace and it’s essentially a vacation in the woods. Really deep—

[00:45:37] Sam Yarborough: In the woods. Is this just you? The kids are not involved?

[00:45:39] Jeff Gangemi: There’s kids. There’s kids.

[00:45:40] Sam Yarborough: Okay. The kids come—

[00:45:40] Jeff Gangemi: They’re there, but there’s room for them to be around but not in our space. And there’s a little—it’s on the end of a dirt road and there’s a loop that goes around. My grandma would call it the loop. She was German—the loop. And it’s about a—

[00:45:56] Sam Yarborough: So that has stuck.

[00:45:58] Jeff Gangemi: And we can just walk around that loop without worrying. It’s twelve or fifteen minutes. You could check back in on the kids. Are they still good? If they yelled, we could still hear them around the loop. So we would have—even when they were, I mean we didn’t leave them until a couple of years ago for more than a little while—but to still be able to get that reconnection time and it’s sort of what’s this year been and what’s this year going to be? It’s not as formal as some of those—

[00:46:24] Sam Yarborough: Sit down and have your spreadsheet.

[00:46:26] Jeff Gangemi: Yeah, there’s no spreadsheets. Shannon’s not much of a spreadsheet person and I’m not really either. But I think that’s a big one for sure. And that feels lucky that we have that opportunity. It just happened as opposed to being conscious again. But I think if there’s a through line here, there’s an intuition and a drive toward these things. Sometimes it’s not conscious, but then getting a shorter and shorter amount of time to recognize that there’s a pattern and something really beautiful here that we can then bring into the conscious space and make a ritual and make it into something that we can really grow from is a nice thing I’m taking from this conversation that I’ve maybe done here and there in the course of the last few years.

[00:47:14] Sam Yarborough: And the recommitting of that to each other, I think hugely important.

[00:47:18] Jeff Gangemi: Yeah, no doubt about that.

[00:47:20] Sam Yarborough: You sent over some topics to talk about, and I slacked this back to you like, I want to talk to you for four hours. There’s no way we’re going to be able to go through all of this. So I do feel like we’re getting cliff notes here, but hopefully this is just an excuse for people to reach out and get to know you. So you have two kids, two girls, as we’ve talked about. There’s been a lot of transition in your life and their life. But you’ve built this family that the culture around it is really curious and adventurous, and you’ve done so while dealing with anxiety, which I feel like a lot of people would say are not typically said in the same sentence. How have you dealt with that? Was that an intention? Was this a challenge? We’ve kind of talked about this already, but how has this changed the trajectory for your kids and what has that journey looked like?

[00:48:11] Jeff Gangemi: We love adventure. Despite the anxiety, for as strong as the anxiety is, that desire and that love of adventure as a family culture has been stronger. And so because of the intimacy that created between our two girls, and I think the pandemic maybe had something to do with it too. It just brought—everyone was so close as we all experienced traumatically, but also really connected. I mean for most of us. I don’t think some people were like, I can’t wait to get as far away from you as possible. But a lot of us had the opposite experience where it brought us a little bit closer together. And then—so we were very lucky to have that Costa Rica experience on the way back from California to the east coast where it was super locked down-y in a lot of places. But we were out in nature together and making the best of that situation. And they kick and scream. They kick and scream a lot when we try to get them to go on longer hikes in Maine, for instance.

[00:49:14] Sam Yarborough: That makes me feel better.

[00:49:17] Jeff Gangemi: But the feeling toward the end when, in spite of themselves, they feel super connected and a little bit tired—like the starch is out of them—and they’re in that space of connection with the family that came from that willingness to adventure, is really awesome.

[00:49:37] Jason Yarborough: Going back to our initial conversation, do you feel like getting them into these adventures is teaching them curiosity?

[00:49:44] Jeff Gangemi: No doubt. No doubt.

[00:49:46] Sam Yarborough: And resilience.

[00:49:46] Jeff Gangemi: And resilience. Boom. Yep, we just said it. That’s it. Curiosity about other different cultures and resilience to be able to figure out how to interact and be in all these circumstances that can feel unworkable and even scary and just foreign, but they’ve figured it out and they know they will figure it out.

[00:50:07] Jason Yarborough: Absolutely. Alright, let’s bring this home with a couple of hot questions for you.

[00:50:11] Jeff Gangemi: Oh boy.

[00:50:11] Jason Yarborough: Oh boy. Let’s do it. Jeff Gangemi, what are you reading right now?

[00:50:15] Jeff Gangemi: Oh my God, that’s so funny. I didn’t expect that one. I’m reading Nirvana: Come As You Are, the story of Nirvana.

[00:50:22] Jason Yarborough: Oh wow.

[00:50:23] Jeff Gangemi: The band. Yeah.

[00:50:24] Jason Yarborough: Good read?

[00:50:26] Jeff Gangemi: It’s a pretty good—it’s made me want to listen to the music more and watch “Where Did You Sleep Last Night,” the song that they do on Nirvana Unplugged—the last song on Nirvana Unplugged. MTV Unplugged. Do you remember that? Watch the video of that and watch Kurt Cobain’s other-worldliness. It’s mind blowing. It’s crazy.

[00:50:49] Sam Yarborough: Okay, I have homework.

[00:50:51] Jason Yarborough: I was a big fan back in the day. One of my favorite songs is still “Something in the Way.” Good Nirvana song. What’s a book recommendation from you—we’ll go with personal development.

[00:51:01] Sam Yarborough: He goes to his bookshelf, ladies and gentlemen.

[00:51:04] Jeff Gangemi: I’m just looking.

[00:51:05] Sam Yarborough: I’ll give you one that you just recommended to me that I just finished.

[00:51:09] Jeff Gangemi: 15 Commitments of Conscious Leadership. That is an amazing one. Yeah, I don’t even need to hesitate on this one. 15 Commitments of Conscious Leadership.

[00:51:18] Jason Yarborough: There we go. There we go. We got it.

[00:51:19] Jeff Gangemi: It’s a great book. Beautiful. That’s actually a dynamite book because it is digestible, but it’s got heuristics and super easy to reference rules and behaviors. Are you above the line or below the line? You’ll always know that. You’ll always be able to reference that. Really, really useful book and it’s awesome for coaching too. Yeah, I would highly recommend that one.

[00:51:39] Sam Yarborough: Yeah, I’ll link it in the show notes for everybody. But Jeff, this has been so refreshing and as it always is chatting with you, so thank you so much for joining us today.

[00:51:50] Jeff Gangemi: This has been a pleasure and an honor. I really appreciate it, guys. Thank you.

[00:51:54] Sam Yarborough: If people want to find you—LinkedIn, is that the best place? How do we get—

[00:51:58] Jeff Gangemi: Yeah, that’s the way. That’s the way. Yeah. If you find me on LinkedIn, I’ll be happy to connect.

[00:52:04] Sam Yarborough: Alright, well Friends, I hope you enjoyed today. Push yourself, go be curious. Go find some resilience in yourself. Fear of starting over. You can do it.

[00:52:15] Jason Yarborough: Chase it all down. Be great. We’ll see you all.

[00:52:19] Sam Yarborough: Bye everybody.