Chris Winfield, a friend and fellow New York City dad, shares his journey from a driven, successful entrepreneur to a recovering addict who rebuilt his life with intention. Growing up in Tuxedo, New York, near the wealthy gated community of Tuxedo Park, Chris internalized a belief that money equals happiness, feeling shame about his family’s relative lack of wealth from a young age. His upbringing was marked by constant activity and responsibility, with parents who emphasized exercise and work, leaving him with a lingering guilt about rest and stillness. After college, he stumbled into the dot-com era, joining a web development company with unstable partners, where he excelled at cold calling but grew disillusioned with the industry’s empty promises. The 9/11 attacks were a pivotal moment, prompting him to start his own business focused on real marketing and driving traffic. Despite his success, he struggled with addiction, which eventually caused his business and life to implode. In recovery, he embarked on a journey of self-discovery, learning to value connection as his greatest strength. This led to launching Unfair Advantage Live, publicity events for entrepreneurs, and Super Connector Media, a venture dedicated to helping people share their unique gifts. Chris’s story highlights the dangers of equating wealth with happiness, the importance of intentional living, and the power of service and connection in rebuilding a meaningful life.
(upbeat music) - So my guest today, Chris Winfield, is actually a good friend of mine. We have been part of a group of New York City dads who've been meeting on a regular basis for years now, just to kind of support each other. And I'm really excited to be able to dive into his story with him. So in the late, or in sort of the mid to late 2000s, Chris was really riding high. Living fast, a co-founder of one of the hottest creative agencies in tech, pretty much had the world at his feet, but secretly, he was dying inside. He was addicted and at what seemed like the height of his success, Chris's business and his life pretty much completely imploded. He realized there just had to be a different way. And starting in recovery, he set off on this journey of rediscovery, deeply personal seeking to figure out who he was, what really mattered to him from the inside out and how he wanted to serve. And years later, coming from a way more intentional and healthy place, he's completely rebuilt his life. He's clean and sober, leading by giving, and found a way to tap what he learned was actually one of his greatest and most valued strengths, which was his ability to connect with people. That eventually fueled the launch of a series of publicity events for entrepreneurs at X-Bart, he called Unfair Advantage Live. Along with a new venture called Super Connector Media, which is really fun and cool, because he's on a, kind of a mission to help people share their unique genius with the world. Really excited to share Chris, his story, his rediscovery and reclamation and devotion to service in today's conversation. I'm Jonathan Fields, and this is Good Life Project. (upbeat music) - Backmarket is the best place to get the tech you need for back to school, for less, like professionally refurbished smartphones to take those first day picks. - Mom, your fingers blocking the camera. - Or so they can ask you to buy a poster board for the science fair tomorrow. No matter what you needed for, the premium refurbished tech on Backmarket is guaranteed by the Backmarket Promise, professionally refurbished with a one-year warranty and free 30-day returns. Save now at Backmarket.com. I was never really allowed to be still growing up. Never, like that was not something. I was, you wouldn't walk into our house growing up and see anyone just like laying on the caroture, meditator, anything like that. Like it was always your head to be in movement and I still have that where I'm like, oh well, I'll feel guilty. Like if I just, I'm my own boss, you know, for a long time. And if I decide to like stop in the middle of day and watch like an episode of Billions, I'll have guilt around that or like, let's say Jen comes home and like I'll jump up and like pretend I'm doing something because I'm like, oh, I don't want to hurt it think that I'm not doing anything. So there's like a certain amount of almost shame associated with just kind of chilling. 100%. That's so interesting. Oh, 100%. And you can tag that back to when you were a kid. Oh, yeah, without a doubt. It was, you know, there's a lot of reasons for that but it wasn't something. Our house was not just a place where you just did nothing. Yeah, which actually kind of like, I mean, like I like I've met your parents. And actually, I met your dad the first time when he was like in the city because he was helping out at the New York City Marathon. So I'm guessing that was part of the whole like philosophy and ethos of movement. Exercise with essential still is for them. So his father died from heart disease when he was about like nine. And I think that there was this whole idea like that he didn't want that to be him. So exercise being healthy became just paramount, you know, above everything else. I don't know if above everything else, but it's still that way. So it's like, there are still, they'll come over. I love my parents. They'll come over though. And it like to see me and, you know, they always have to have a plan. You always have to know what we're doing, what we're doing, what we're doing. And that was like my life for for so long. And I think I can still go back to that really, really easy. Yeah, were you an athlete as a kid though? Not anything good. I didn't, I had this story that I wasn't. It's really interesting, you know, the stories that we tell ourselves or just, I had this idea that I wasn't a good athlete. And, you know, now, as an adult, like people are like, oh, you're great athlete. And I'm like, no, that was not, that was not me. I mean, I did sports because we had to always be doing something. We had to do, you know, a sport or have a job, you know, all these different things. So I did the stuff, but I did it so half-assed and just not, not into it at all. Yeah, well, also, I mean, when you're a kid and that's sort of like mandated from the top down, it's not the thing you want to be doing. Exactly. You had part of the growing up thing was yet to have a job also. Job, yeah, sport, job, all everything. So it wasn't just about movement, it was about, it sounds like responsibility. Everything. Yes. I mean, it was like, all right, and that's the crazy thing was, I was constantly getting in trouble. I was not like a good, no, I mean, I was a good student just because I was able to, even if I half-assed it, I was able to do well, you know, just get by on, you know, brains or whatever. I never studied and you always got in trouble. That was like my M.O. For what? Talking, everything, like I literally, and my poor mother, so my mother was a school psychologist, but both my parents were at the school that you went to? My high school. Poor. And when I say, like I got in trouble every day, that's not like an exaggeration. And that poor woman, you know, she had teachers or friends that would just stop talking to her forever, all this, it was awful. I feel really bad. Every time I bring that up, I'm like, I get to call my mom after this. Make a man. So when you finally graduate high school, she's like really happy, but, you know, like for multiple reasons forever. But then my brother was right two years behind me. And in different ways, he was just as much trouble, if not more. So right in the family, some rebellion. You go up in Tuxedo, right? Tuxedo, New York, and then further up state. Right. Which for those who are hanging out in New York City right now in Tuxedo is like an hour and a half or so north of New York. Exactly. And for those who have never heard of it before, it had-- so the only way that I know Tuxedo is that as a kid, I went there for-- it's kind of become legendary for the Renaissance fair. So like every year you go out there, and they're like, it's taken over by people running around and tights and eating with their hands. Yep, exactly. That's sterling for us, which is right past Tuxedo. It's all kind of considered the same. Because they're so small. Tuxedo has Tuxedo Park, which is like the only gated town in-- like the only gated public town or something in America, I believe. That could be wrong. But-- And then like actual gated? There's an actual gate to get in. So there's Tuxedo Park, and then there's Tuxedo. And Tuxedo Park is one of the richest communities in-- I don't know-- in America, there's like so many celebrities that live there, a lot of hedge fun guys. And there's an actual gate that you have to go in. And then I lived in Tuxedo. So I literally lived on the other side of the tracks. When people say that, I was literally on that other side. And that growing up, that shaped me so much. Because I grew up so close to extreme wealth. But I did not-- that was not my story. And I remember having so much shame around not having money. And we would go in-- like when you go to the gate to go into Tuxedo Park, you have to actually-- if you don't live there, you have to say, we're here to see blah, blah, blah. And I can remember at like six years old having shame around that. Because if I was going with like a friend or somebody who lived there, they just opened the gate automatically. So I guess here in New York City, my building has dormant. So it's the same thing for your building. You have to announce yourself. If you live there, you just walk right in. And it didn't bother anyone else in my family. It always bothered me, extremely. And I just thought that everyone in the park was happy because they had so much money. So I literally made that connection. All right, these people are all happy. I'm not. I don't have money. These people have money. They're all happy. So it's-- and it drove me for so long. Yeah, so like it's six years old, you literally have this thing in your mind that says, happiness is money. Completely. So directly. That's kind of fascinating. And I believe-- and I knew the crazy thing was, this is what's so weird about how powerful stories like that can become. I knew people that lived in there. A lot of my friends and their parents were miserable people. And there were some happy, nice ones. But most were not. But I didn't even think of that. I didn't equate that. I just had this overarching belief. Everyone in here has money. They're all happy. Yeah. It's the stories that we want to tell ourselves. It's funny because I grew up in the town where it was East Aged from the Great Gatsby in Port Washington. And the town was overall, actually, and you're like fairly well to do. But there was Port Washington. And then there was Sand's Point, which was the tip of it, where there was some pretty astonishing wealth. And I saw a lot of the same things. And I remember having similar struggles, not so early. But I remember in high school. and reflecting back on that.
it's funny because you look at like, well, the haves and the have-nots, we didn't, we weren't really the have-nots, you know, but when it, but we're, I mean, we live such lives of comparison that when you look at just astonishing wealth, it makes somebody who's actually like the family's fine and everyone's good and we're like, everything's great. It's like, there's something that happens to that tour of brains where it just kind of flips into this mode of like, wow, oh, what was me? Exactly. Yeah, and I had this story that I had like, no money growing up because that's how we kind of lived, but that's not really the case when, you know, and compare myself to somebody who truly is, you know, like, destitute, but comparatively, I had how I thought because we had, you know, we couldn't just go out to dinner, we had, you know, things like that, but I just, I believe that and I chased that for so long and I still, you know, I can still revert back into that. Yeah, well, I mean, we're living in New York City, so it is, all you have to do is look up and you see it around us on every corner. Exactly. So when you went off, when you went to college, you went to Albany, right? Yeah. So when you went to Albany, in the back of your mind, was this sort of like the first step towards that big master goal? No, I went, I had no plan. I had no, there was nothing like, I wound up going to Albany because it was convenient. Yeah. My father said, we'll pay for a state school. I didn't want to do anything more. I just went there because I think that was like the first place that I went to on the college tour, like, and I went to also Buffalo and it was snowing the entire time. I was like, all right, let's go here to Albany, which Albany just is a weird thing. Is it upstate in New York that the actual campus was designed for Arizona to create wind? So you hear on campus, it's like 15 degrees colder. It's miserable. And I hated it. I hated, I just because I was so unhappy as a person, you know, I struggled with, I didn't even realize it was struggling, but with addiction and drinking, you know, and all these, I didn't realize at that time, I just thought that's what everyone did, and the people I was around were like that. And I had no plan. You know, some people say, like, oh, I knew exactly what I was going to and, you know, become an entrepreneur and all this. And that was not my, that was not my story. What'd you end up at your study? Political science. I used to want to be a lawyer. Oh, I just, I just, you were a lawyer. Which is funny because I studied political science too. And the only reason was because my senior, I could not figure out like what I should do to graduate. So finally, I'm just like, I have enough courses in this. Yeah. I had no intention of being a lawyer at that point either, even though I ended up going down that path. So you come out of there and this, this was then the late 90s early 2000s. Yeah. Right. The early 2000s. Yeah. So this is a really interesting time like in the economy and the dot com world too. Yeah. And I was looking for a job. So again, I'm been an entrepreneur for almost all of my life, but it was not what I didn't think that that was possible for me. So what were you doing as an entrepreneur when you were younger? No, no, nothing. Meaning like in my adult life, I've been an entrepreneur. But I, so I'm, so here's an interesting thing. And my immediate family, not only was I the first person becoming an entrepreneur or, you know, I was the first person that worked in a school system. Oh, no kidding. So my parents were both school psychologists. Then my brother became a school psychologist. My sister worked in a school. So I was like the first one to just not do that. So I, I was looking, you know, trying to get different jobs or whatever. My sister introduced me to this guy who was a family friend of like her husband's family. And he used to be like a huge farm executive. And she's like such a good guy, you know, family man, all that. So he was starting a web development company with three other guys. This was around the time that like a company called Razerfish was trading at like $200. Right. It's like $1 billion, you know, multi-billion dollar company. Everyone's just making up the weirdest name you can for like, whenever the company is. Exactly. And people are just throwing money. So these guys, so started this company, web development company. Now the farm executive, six months in wound up being in rehab. He had a terrible coke problem. He had left his family, all these different things. And he was like the most stable of the four partners. So another guy was a like the number four guy at Stratt Oakmont, which is like boiler room wolf a wall street and something based on. So which I didn't know any of this stuff at the time. And then another guy wasn't allowed to trade securities in like New York and Connecticut and you know blah blah blah. And it just keeps going on. And my job was making phone calls, like making calls, like basically cold calling people to get up to get appointments set up where you know, to see to demo like our web development stuff. And I was really good at it. Like I would call like 300 people a day at New York. So it was like the most miserable thing. And then I led the telemark, you know, all this stuff. And I worked really hard and I was just expecting like, all right, this is it. So like that six-year-old kid, all right, you're finally going, this is like your ticket to happiness. You're finally, because everyone was becoming, you know, multi million and billionaires from the calm days. And this was it. I had an office like overlooking Statue of Liberty down on like water street and all this. And it did not work, obviously, as you can probably tell from the foundation of those four guys. But it just like I wound up leaving there and I was like, I never want to, I never want to make a cold call again in my life or do like people would spend so much money on, you know, on these websites that would do nothing. So I kind of decided, all right, I'm going to do the opposite. But it was it's just amazing like how I really thought like that was the key. That was going to be it. And it was so far away from being it. Yeah, I mean, at the same time though, it's like to to be in that environment, especially straight out of school on the one hand, you know, there's a lot of stuff that you see that you realize is all smoking mirrors. But on the other hand, there's a lot of stuff that you see that's all smoking mirrors. It's like you kind of like the illusion or you're like the, you know, the fiction that you were telling yourself from the time that you were sick, you start to like realize pretty quickly that there's something that's like not quite right about this. And I think a lot of us don't wake up to that until or at least start to see hints of the fact that that might not be real until way later in life. Yeah. And I didn't, it still didn't completely know. I mean, all I knew was what I didn't want. Right. Which was what these guys are doing. But I still, I wanted like the, I still wanted the money. I still had I wanted all that like that still was the driver for me. Right. So money still the driver at that point, you're just like not this way. Exactly. So what do you go from there? Started my own business for it and who's completely as a result of just seeing what didn't work. And then figuring, all right, here's how we can make it work. So these guys were like doing building websites that weren't doing people things for people. So I'm like, I just started learning about marketing and you know, how to actually drive traffic and stuff like that. But this was also around the time where everything crashed. Exactly. I mean, because I remember at 9/11, so I was living in Brooklyn. And because that's really like when things started to really, that's like for me, like was such like a turning point. And I remember, our office at that point was like in like flat iron area. So for people who don't live in New York, like 20s or sometimes I don't. I was living in Brooklyn and Brooklyn had a the W train goes above ground. You're like going over a bridge. And I remember stopping in the middle of the bridge, the train stopping, the guy, the conductor started like talking as if it was, as if it was like Disneyland. And he was like, if you look to the right, you'll see that the twin towers are on fire. It was like really that like not realizing what was going on or anything like that. But the reason I'm telling this story is like this was such a turning point for me. I wound up like getting to our office and watching one of the towers. I was always used to have a view of that. But that next day, after getting, you know, through all that and the next day, like not even having enough money to go to like to dinner or anything. And calling our boss and be like, Hey, do you want us to come into work? Like that's how I was still that like driven. And you know, and him being like, Oh, no, go out to it. He hasn't been paying us all this stuff. And you know, that being like the huge turning point for me. And then that, you know, that I think the whole world kind of changed at that time. Yeah, it was just it was, I don't know why I'd like been on my mind recently around that whole time. And then that's like right after is like when we wound up leaving and then starting my own company. Yeah. I mean, I think that was a catalyst for so many people to just make some really abrupt changes. And like us both having been in the city.
Yeah, at the time it was it's funny. I sometimes wonder You know, it was it it was it was such a traumatic Window and experience for everybody for like the entire country But for those who were in New York and who are were New Yorkers That day It was different You know, there was something that is just indescribably visceral. Yeah, that changed almost you pretty much everyone I know who was here that day. Yeah, especially just all the different there's like lots of different reminders for me So for example, I lost a lot of people and I remember one of my friends this girl who Then I'd seen her like two days before and bumped into her at the gym and she was I think she was with her mom And I remember I was drinking Fiji water and she's like, oh, that's my favorite water So anytime that I pick up a bottle of Fiji and like I always remembered that and You know, and it wasn't like I wasn't super close to or anything like that, but it's just like that That interesting like different little things like there was there was a kind of a massive wall in New York where people just started Taking tiles little ceramic tiles with people's names or just remembrances and Put posting them on offense and became this massive sort of, you know like back, you know just Crowdsourced memorial from thousands of people and you would go there and it was just it was complete silence there You know as you just walked and looked and My wife and I just literally walked by that spot, you know years and years and years later and there are still It's still there. Yeah, there aren't nearly as many tiles many many have gone away over the years But there are still many up there and I was amazed how in a moment It's like just seeing this like you're back there. It takes you right back. Yeah. It's crazy. It's like it's just beneath the surface. Yeah Backmarket is the best place to get the tech you need for back to school for less Like professionally refurbished smartphones to take those first day picks Mom your fingers blocking the camera or so they can ask you to buy a poster board for the science fair tomorrow No matter what you needed for the premium refurbished tech on backmarket is guaranteed by the backmarket promise Professionally refurbished with a one-year warranty and free 30-day returns save now at backmarket.com So this happens and at the same time everything's falling apart in the company right and this becomes a catalyst for you to say okay Things need to change but you also you didn't decide to go somewhere else here like let me I want to define my own thing But it's my power yeah, and I just started learning and That was like that's how I've learned everything like just online trying myself like no I didn't have a mentor. I didn't have any training or anything I just started like reading and learning and just trying things it always sounds so much better in Looking back like it wound up being great, but I mean as hell, you know I think that that's like an important thing to remember like I was broke as a joke for a long time You know really long time and but then I would again like I was still tracing like I'll be happy This has been a big theme for me is like I'll be happy when all right when I get to this when I don't have to worry about this or And I just remember like never like it never works, you know it works for like 30 minutes like whatever those goals are I remember like the first time I got like a nice car I'm driving in home from New Jersey and for some reason put in New Jersey and And like feel I felt great for like 30 minutes like driving and like you know smelling the new leather all that and BMW and I don't just win them way like I didn't even make a fact in New York City and it was gone. I was like oh man It's so sad. You're like I need to get your drive this back and get the bigger shot Yeah, exactly and then that would go you know that would last 31 minutes maybe yeah, but still you're in it So it's like even though you're feeling do you actually here's my curiosity When you look back can you remember like that was what happened or do you do we call actually feeling that in the moment Why you're literally like you're driving it in by the time you hit New York City or like okay, so That was nice, but what's next? Yeah, I This is an interesting it's such an interesting question because I Sometimes wonder about my own memory like I think I have I think we all have this ability So like you can change what your actual memory is so I don't know if I Felt that right, you know how deeply like I in my mind I can see it and I can feel it exactly as it happened I wonder if that's exactly the way like if I had that realization Be as perspective is so unbelievably powerful and Perspective can you know, I can see it so clearly now. I'm wondering at that time in like you know 2004 or whatever How how deeply I felt that yeah, because I mean so you start a firm. This was a 2020. Yeah Because the office was on 10 East 21st Street and then at that time Numbers came up before like directories were so important like Yahoo was like a directory and Like that was so important so numbers came up before letters So I'd always be at the top of any list or anything like that I think an SEO I was big SEO guy and that was also so that was an apartment in New York City where Back then it was considered there was like a small slice of Manhattan that was considered Silicon Valley I don't know like we were we were chasing Silicon Valley and so that address For non-New Yorkers would have been in the heart. Yeah, like right in the world Everything was happening in the tech world in New York City and all the explosive growth and everything Yep, is your intention at that point to just build a giant? My intention when I started was Just get money coming in Meaning like instead of getting a job like it was really that simple like again like I did not have that mentality yet of Really wanting to be an entrepreneur or you know do something remarkable or anything like that I Was not at that level in my life where that really that really matter I mean, I was very still very self-consumed so I was like all right well build it help people doing this Doing it better than we had been doing it and you know Make enough to live on. Yeah, so do you start this alone or with other people? My wife that well we weren't married but my ex-wife right yeah, so you're dating at the time. Yeah exactly So which it adds a whole another element to this? Why make it why make it easy? So you're so that firm though. I mean looking back you know that when we know the history of that firm And actually it grows to become This sort of like rock star in that world. Yeah, and well, so that wound up becoming really It did great. Um, I started speaking. I started focusing on publicity to differentiate myself started being the Person the company that people would want to hire to do you know something cool is like the Was like the really um like I just kind of like the rock star status of it and Then it got to a point where I was gonna then sell it because I got really focused on all right I want to just build this to sell it and I Got to a point where I had the offer in my hand and it was a good offer But there was a two-year earn out and meaning I would have had to work for the acquiring company for at least two years and blah blah blah And at the last minute I was like nope, I can't do it and I think immediately I put down the the paper Pick the phone called a bunch of different people bunch of like competitor/friends that did similar things and we formed something Bigger and again now here it was where I was like all right now. I want to build the biggest best agency in the world Yeah, so this was like okay, so now we're gonna turn this into like my razorfish exactly Yeah, um, so you partner up with a bunch of other people who had been doing their own thing to create this sort of like bigger agency That what year are we talking about that point? That was 2008 or nine 2009 I think right um and you're on your way and you're in your mind 2009 maybe two thousand time actually two thousand time. Yeah. Yeah. Yeah. Completely. Are you happy at that time? Oh, it's miserable so I I was not so now I'm such a person focused on personal growth spirit None of that stuff. I was focused on me and I was focused on ego I was focused on how I came off to people what people thought about me. I mean completely so also I'm attracting people like me and Yeah, it was just I was miserable. Absolutely miserable now if you looked at my life on the outside You'd probably think it was great, you know, I'm constantly being talked about like a great pup all this stuff and I was absolutely miserable now I didn't
really know how miserable I was. And also, I mean, I had, you know, I was struggling with addiction, like again, not even realizing it, but no, it's like now, obviously looking back at you and talk about that. But so I didn't know, I didn't know how miserable I was. The way I was described is like I was comfortable being uncomfortable. And there's different levels of that. There's like a good uncomfortable where you're pushing yourself out of your comfort zone, literally. And I think that's like a really powerful and comfortable. But there's also like an uncomfortability where you're just like stagnant. And you're just kind of miserable. But you don't know it. And you don't want to change anything because there's like safety in your misery. That's what it was for me. Yeah. And I mean, not only safety in your misery, but there's also if you're surrounding yourself with people with the same value set and who are all equally miserable, there's like camaraderie in it. There's a sense of like your sense of identity and belonging is built around us all feeling this way. Exactly. Yeah. And when you have a lot of power in choosing who's going to enter the realm, it's like you just keep adding more people in the with that same lens. Exactly. Yeah. So, so at that point, you're also struggling with addiction. What how did that show up? It showed up by just being a complete ego maniac. It showed up by, you know, I mean, literally just being oh, I had a, by the time I got sober, so I got sober on January 3rd, 2011. So there was like a nine month period from starting this company to that. So this is the new company. Yeah. And I was just never, I was never the best way to describe is I was never present. So even if I was, I had a new daughter who, you know, now, like it blows my mind to hear this, but I was not a part of her life. You know, I walked out of her life at one point. And, you know, I was just, I was not, I was not a person. I don't know. It's the best way for me to describe it. I was just, I was just there. I was taking action, but not in any way that was doing anything. I'm so disconnected from just from not only other people, but from myself. Yeah. Completely disconnected. So what happens on January 3rd, 2011 to make that change? So it was more like December 28th of 2010 is I had this moment. I had moved to Florida. So when I talk about like, I literally walked out of my daughter's life. And I was married at the time. I walked out on her and moved to Florida because, you know, that day were the problem. Or, you know, not my daughter, but, you know, whatever it was. And I'd missed a bunch of flights back from Las Vegas. We had just acquired a company and, you know, is out there speaking. It was like a mess. And I come back and I move, I move to Florida. We have an office down there. So I'm going to move to do that because there's something in that the in like the recovery where they call it is a geographic. So you know, I've changed where I live. I'm going to change myself. So you can do a geographic with so many different things. A job, a girlfriend, blah, blah, whatever it is. I move down there and it's a mess. And the whole time, which is a blur and I come back up for Christmas. And I am, you know, with my family and, you know, not staying at my own house or anything. And my daughter's first, first real Christmas. And where I remember being at my, at my sister's house and I've also three nieces. They come running in Christmas morning, like six o'clock, you know, to, you know, to go up in presents and I have to go and like take drinks and, you know, in the bathroom just to be present enough to watch kids open presents. So that's kind of just to give you like an insight into like where I was at that point. And I then, you know, go on like that for a few days. I was supposed to go back to Florida. And I knew like in my mind, it was like I hadn't been going through with like these three thoughts for a long time. Like, you know, continue living the way that I was living. And I'd always thought I'd be dead by 40, you know, from being a little kid even before. I don't know why, but that was always kind of the, the idea. It was really it's crazy for me to say that now. And, you know, number two, the second thought was, like, just, you know, ending at Kilmuth, you know, like, just don't want to live this way. I didn't really want to do that. But I was so miserable. And number three was like getting clean. Now I didn't know anything about sobriety or anything. It was just getting clean. They all seem like equally good. Now again, at this point, like, if you look at my life, like, it looks good. I'm, you know, all this stuff. But like, this is why social media and all these things can be so dangerous because like, you don't know. And I wound up just, I wound up going back to my house. And I had this whole argument with my daughter's mother and, you know, wound up like she was like, I just can't have you in our life. And I wound up going into my kitchen and I'm in the kitchen. And at my island, and I just had this thought. And the thought was, I can't do this anymore. That was it. I'm too tired. And I was like, she came back down to stairs and she'd be, she'd went up to put my daughter down for a nap. And I said, listen, I want to get clean, you know, I don't want to drink anymore. And she said, all right, I'll help you. And I'd wanted to go to this, like, 10-day treatment center. It was the first thing that came up in Google. And it was an inversion therapy place. I didn't know anything about. So basically, if you go there, then they, like, he drank or something. And then they, they give you like true serum. And then it's just this awful thing. And so I'd said, I want to go this because I was just like, I'll get it done in 10 days. I didn't know anything about recovery. I didn't know it's like a, you know, lifelong thing. And we had been seeing over the summer, this guy, this counselor, and she called him and this guy never would take a dollar from me because he's like, I can't help you. You're not ready. And that was like, it drove me crazy at the time. And so she called him and she said, Chris is ready to get clean. He wants to go to this place. And the guy was like, well, Chris is done making decisions. Here's where he's going to go. He's going to go to Karen Foundation in Pennsylvania. And that's where I wound up going. And the reason is December 28th and January 3rd is they couldn't take me until then. They couldn't take me. And I was fine with that. You know, so this is an important thing. He's like, even though I was ready, I still needed all that time. You know, and it wasn't like I had some quarreys like, you know, New Year's Eve party or anything. It was like mostly just being like passed out or whatever. But when I went there, I just listened, you know, even though I didn't want to, I was ready. And I think that's an important thing with change is that it's not like I wanted it, but I didn't want it 100%. Like I think there's this belief. And I know for myself, like I can get this belief, like I got to want it 110% or, you know, and especially now, there's like all this like with hustle and you have the hustle, you know, 1000% and blah, blah, blah. And like for me, the thing that I started thinking about back then was I just have to want it a little bit more than I don't. So I always look at like 51% of me. Like that's it. Like so somebody would come in and be talking. I'm like, oh my God, I hate this person so much, but they're so stupid. But I wouldn't get up and leave. And I would listen. And, you know, that and that's been like how I've changed everything from there. It's like 51% means 51% gets me those days when I can have 90% or 65%. So. Yeah. So when you come out of that, how do you step back into your life again? And what? Slowly. And I mean, what, so you've got, because you're still in this company, right? You're now different completely. The entire, like everything that you've built and the culture that you've built and the assumptions about how you be in that culture is different now in the context of like your personal relationships. That's probably a good thing, right? Because the expectations are like, okay, so now we've got something to work with your back. But in the context of this like your own company that you've built where the culture is like, no, no, that's not how we operate. Yeah, it was, it was a challenge right from the beginning. So they're biggest a big part of how I grew my agencies and built so many of my relationships revolved around drinking, revolved around going and speaking at conferences and then going out at night with people. And so I had had, you know, I'm struggling with this whole idea of like, how can I have a successful business and not drink? Like that was such an integral part of it, which now kind of blows my mind eight plus years later and realize like it's almost crazy to me. But that was such a big part. And then, you know, that's also how all my, you know, relationships had formed. And that's what they were around. So yeah, that they're,
right from the beginning, it started to cause like there was such a disconnect. Yeah. And it sounds like at the same time also, the new entity was having some issues. Yeah. I mean, from kind of from the beginning, and it just, but then we just kept growing it, growing it. And you know, it just kind of hummed along and looked great on the outside and was complete mess on the inside. And it was like a perfect example. I always say for like me, you know, like it was an analogy, because I was still, even though I was so, we're doing all this stuff, like I still had this huge tug in me, like I would go into my own office and feel miserable. And you know, realizing, like, what am I doing? Like, how am I really giving back or contributing? And, and then I was very outside of recovery. I was very disconnected. You know, I, because there was this whole thing like about connecting with people and it was so, in business, it was so related to drinking and it was so related to partying and all that. And I just, I couldn't do that anymore. I was, you know, that was just not who I was. So that, that, that, that just kept going on. And then the company like, spectacularly imploded, you know, I guess about two years after that. And it was like all the, there's like the saying is, I got, can we'll do for you what you can't do for yourself? I probably, I don't know, I didn't have the strength to just leave, because that was my identity. That was like so much of who I was was tied up in that company. I think the same can happen for people in like a relationship or, you know, whatever it is. And you just again, like you stay stuck. And it's comfortable, it was comfortable being uncomfortable. And then that just like all kind of imploded. And, you know, it was like all the worst possible things that I could imagine. Like, all kind of happened. And it was very public and just like gross. And it was like looking back. Like that was one of the best things that ever happened. I mean, my life, but it fell horrible. Like I've read, you know, Facebook memories, I got one from like six years ago. And saturday and I showed it to Jen and was like about like, you know, taking the high road. And, you know, based on just at that time, it was just so like, you know, painful and going on. And I, that's also where everything started to change for me. Like that was like part two in terms of so getting sober, which felt like the worst day of my life ever waking up in rehab. Like literally, I wrote down on a piece of paper, this is the worst day of my life. I wanted to be a, that's the day I look at every single day as the best day of my life. It didn't feel like that. Now, when all this stuff happened, this was like act two for me. This was the beginning. And, you know, there, it just, it still amazes me how we have to not, we don't have to. But for me, I've had to go through a lot of pain to get that growth. And, you know, that's, so this is like where then, you know, the whole next part happened where my, oh my god, I'm so unbelievably disconnected from people. Yeah. Because now you don't have this whole structure to distract you from whatever level of suffering you're in. At least you go to work and you can be distracted like 24/7 when this massive thing implodes. And then it's you. And not only do you have the, like the struggle of figuring out, okay, so, you know, like at that point, like, like, you're married, your father, you're living in New York City, high standard of living, really big public enclosure. I was living in Florida at that time. Right. In a gated community down in Florida. So I hadn't even made it back here yet. Right. And this is being in public also. So there's like a big public reputational thing. Yeah. And you're clean. So you don't have a community that's really clean and sort of like looking at the same way as you outside of the people like recovery, recovery. Where do you go when you're brought to your knees at that moment? I mean, what's the next move? Like, how do you look up and then say, okay, so how am I going to be okay? Yep. I, to the big thing I started to get, I started to get healthy, really healthy as a person. I remember one of the books that changed everything for me. And so we already lived a block away from us is I found James Althacher now who's now a friend, but which is so weird because at the time, I read a tech crunch article that he had wrote like 101 something. And I was like, oh, I love how this guy writes. I went, bought his book, choose yourself, start reading that. He has the whole thing about like daily, I think you call the daily practice, you know, just doing these different things. And I was like, all right, this really makes sense. I started doing my own, you know, I call it daily routine. And you know, really focused around getting, getting healthy like mind body soul. And so I start that. And then I realized I'm still like kind of disconnected. So I start to reach out to people and set up meetings. And at first it was in Florida. And I start meeting with no matter what one person day. So when I say meeting, sometimes that was phone calls. But a lot of the times it was just, it was just going and sitting down with somebody. Now it's so strange, but I was so nervous to do that. I do it all the time now, but I was so unbelievably uncomfortable. Like what was behind that? I think I was great being able, I was great being able to be up talking into a crowd or whatever. But then when it was just one on one, no alcohol, no nothing, just getting into like vulnerable stuff. And I never would have talked like this, like talked about all my flaws or failures or anything like that. Never would be because I wanted you to think that I was perfect. Because I was so uncomfortable on my own skin that I needed you to believe that. So I started doing that. But then I started just like opening up because I had so much pain that I didn't know anything else. So as a result of that, just being open and like vulnerable with people, people start telling me stuff that, you know, I don't think they ever told anyone in their lives before. They still have, like I'll start talking to somebody and like a star like I know wind up telling me something. And I think it's like that. So I'd learned a lot of just being able to be open in recovery and talking about stuff. And so I started doing that with quote unquote normal people and it was just absolutely amazing. So then I was like, all right, let me also instead of like being that person that was looking for something for myself always out of anything. Let me flip that around and figure out what I can do to help people because I didn't need to like I didn't have anything. Like I didn't know what I wanted to do next. I didn't know how is it ever going to make another dollar in my life. Like forget a million five minute anything. I was like, I don't know. Is that was so like scarred from this? And and I started doing that. And you know, I've done that now. I don't even know how long it's been, you know, I guess that was April of 2013 and just doing that. And you know, then doing it in, you know, having dinners and you know, asking people, you've been to many of my dinners and it's just it's absolutely amazing because again, getting back to what I mentioned before, like I realized how much with disconnect there was between what I saw from people on social media or what I saw from people. Like I started meeting when I moved back to New York, I started meeting like celebrities that grew up like worshipping and then talking to them and being like, wow, they have this they're more fucked up than me. Like, you know, like it's it's so it was fascinating to me. So I wanted like I realized how much pain that had caused me. I'm like, how do I like, you know, start to change that for people? You know, because I think that there's such a there's such a belief now we see like all the highlight reals and we see like somebody's perfect life. And I know so many of those people that have the perfect life. And I know, you know, they're pain, you know, I know what the real issues are. Yeah, I think social media really screws with us. And on the one, it's like it gives and it takes, you know, it gives flat ends of the world that lets us meet and befriend and be in service of and and like all these different people who we never would have been able to actually build relationships with before. And at the same time, like you were saying so much of what goes on with it these days is like, here's my shiny happy utterly fake life. And then if you were the kid who had the comparison thing at Tuxedo Park when you were six, which were all that on some level, you know, and then instead of just seeing the gated community, you know, like in your town, you know, you see effectively what is the shiny happy gated community lives of millions of people. And you're making assumptions about how it's so much better than yours. And then knowing also that so much of his just smoking mirrors. Yeah. It's it's it's fascinating to see what it's doing to us. I mean, it's also I mean, you look at the levels of anxiety and depression out there now. Not just in adults, but also in kids who are native to this. It's really scary. The linear relationship. Yeah. It there's a loneliness epidemic. So we're more connected than ever, but we're more disconnected because it's not a true connection. So a chair quick story with you. So I was we do these different dinners like bringing together influencers or that's funny saying influencers when we're talking about all these issues. But media and all kinds of different people we were doing one in L.I.
And at that dinner, there was maybe 25 people. And most had like let's say a hundred to a million followers and seven or eight figure businesses. And many of that people leading absolutely perfect lives. And I always start out and the of our dinner, it's people have like we pay for everything and they just have to answer one question. You know, the question is, what do you need help with right now? And I've found that by getting people to answer and putting themselves in a vulnerable position, it's really amazing because other people help them in all this. At that dinner though, like 60% of those people in that room, the thing that they wanted help with was finding actual friends, like actual connection. And you know, it just again, these are like the people with like that perfect life, but still not feeling, you know, really truly connected. And that's like a, that's like a basic human need. And so that's why I believe in it so much. Because I know for me, that's what changed everything. Connecting, being open, honest, and vulnerable, figure out what I can do to help somebody, a change of mind, higher life, everything. - Backmarket is the best place to get the tech you need for back to school, for less, like professionally refurbished smartphones to take those first day picks. No matter what you needed for, the premium refurbished tech on backmarket is guaranteed by the backmarket promise, professionally refurbished with a one year warranty and free 30 day returns. So when you start to lean into that and do that on a daily basis, changes you, I mean, also on the one hand, I think it changed you because you reconnect with people who maybe see the world similarly to you. You're more vulnerable. So you realize we're all struggling through this in the same way. So the comparisons are like the way you compare changes to. Then you're, I mean, I'm curious also how, you're going through all of this, you're tight with your family. They're watching from the outside looking and what's happening with that dynamic. - So with my family, in what way? - Like your, so like your mom, your dad, your siblings, on the one hand with them, and then also you trying to reintegrate into the life of your kid and then your wife. - Yep, yeah, it was all, so when my family, I mean, a lot of my family time was around, it's interesting like how alcohol, like it can lead to so much, or like it's crazy to me now because, you know, it doesn't play a role in my life at all, even though I'm around it so much. But what I find is that I had to like just re, redo all of my relationships. So that meant completely eliminating a lot of people from my life. And you know, the one, like I literally changed my phone number at one point. And I remember I went to the store and like the Verizon store and Kate, the guy, I was like, I want a new phone number. And he's like, "Oh, you want me to move over "all your contacts?" I was like, "No." And he's like, "Really? "I've never seen that before." But I just wanted to start completely fresh. And you know, and I think that's like such a, that's such a powerful thing. Now that didn't mean like just getting rid of everything in my life, but you know, family and things like that. But it did mean getting, you know, cutting relationships with a lot of people. And some in my family, not my media family, but you know, and I think that's okay. It's unbelievable how many people I've gone through in terms of like the more, this is something people always talk to me about. They struggle with and like, you know, but I found that you have to let go. You have to let go of people. But with my daughter, you know, she was like the big catalyst for, she's the one who helped me realize that I was really disconnected. I got to realize I was disconnected from her. That's what literally led me to start getting more connected to other people. So I'm like, all right, this is the most important person in my life. And she doesn't even feel connected to me. I got to change that. So with her, it's been this whole thing of just, it's amazing. Because now I have the closest relationship with her and she is unbelievably confident in who she is. So she's, you know, she's 10. There's a lot of kids and she lives in, you shouldn't, you know, I'm gonna be 10. But she lives here in New York City in the Upper Oside and extremely privileged life and, you know, around. And, you know, a lot of kids start getting their phones at like seven and, you know, she doesn't care. She's on the monophone. She told me that she called me yesterday. I was in this meditation thing getting ready to start and she's like, can I tell you something? You know, some kids at school had started a group chat and she could care less. Like, and I love that. Like, I love that that she doesn't feel pulled to that. Like, that makes me really, really happy. That's a great reminder for me too, because I probably checked my phone way more than, you know. But yeah, it's, I think a big part of it was just like, either having, I had to kind of learn, relearn how to live or learn how to live. I don't know if I really knew. - Yeah. When you start exploring all that also, I mean, you also have to rebuild your career, literally from the ground up. You know, at Grinney, it starts from you having all the different conversations, but it's also you asking the question, what's next? Like, did you have any idea where did it, so like right now, as we said here in Speak, you run this company and you're all over the media, which is interesting. And very often when, you know, people see you on TV, it's under the moniker, the super connector. - Yeah. - Yeah. You run a company called Not Fair Advantage, where you bring a lot of people together. You essentially, I mean, it feels like to me, and I'm curious from the inside, looking out, whether, it feels like from me over the last, you know, chunk of years now, you've taken those once a day conversations where like the soul intention becomes to be of service too, and just continue to build upon them to figure out how to essentially be the person who understands how to create a snout-ishing relationships that benefit, other people and teach others how to do something similar, and somehow figure it out a way to turn that into (laughs) into a career of living a company, and all these different things. - So my favorite quote of all time is, you can't connect the dots looking forward, you can only connect them looking backwards. Steve Jobs, 2009, Stanford, Commencement Speech. Now, I'm not even a big Steve Jobs fan, but when I heard that, I was like, oh my god, that's it, because I did not know. So we just, like, the Europe podcast, such a great example of this. Like, you hear of somebody's story, and it's all these disconnected things that all somehow wind up connecting. So I had to go through all of those different experiences to get here, and it's, I didn't know. Like, I never would have thought this, and this is a big thing of what I teach people now, is like, connecting with people wound up becoming something that came easy to me. And looking back over my childhood and things, like I always had lots of different friends, and always very close relationship and things like that, but like, would never have thought that I could make money from that, or build a business, or be fulfilled from that in any way. And, you know, for seven months, I had no idea what I was gonna do. No idea. Move back to New York, was down to nothing. We said, "Loss so much money in this business," and had no idea how I was gonna make another dollar. And I don't see that in an exaggerated way. And, you know, then one day, from starting doing all these different things, like becoming much healthier, talking to people, doing all this, like the daily work, it just came to me, and not this, not the business that I do now, but just how I could start making money again, because I didn't want to do anything around marketing, or anything else. I was like, so turned off, and then I started helping somebody, and then I started helping another person with like their business. And as soon as I said, "Hey, wanna hire me to do some stuff?" Like, they were like, "Yes, boom." And then, you know, another person. And then I really was in, like I had to start learning how to actually work. So I got really into productivity. You're laughing, there's a reason, Jonathan plays a key part in this, but I got really into productivity. And then I built a business around that, and I started writing in all these major magazines, things around productivity, and I had this business around that. And I liked it. I didn't love it. I liked it, and started speaking, doing all these different things. And then I, you know, then through, I started doing dinners with my friend, Selena Sue, and I, we started doing these dinners, and then we started doing, we did like a mastermind around like, you know, publicity, because that's how I'd always built everything, was using publicity and all these relationships. And then, here's the reason Jonathan's laughing, is that we're in this small mastermind together. We call it the dad mastermind.
And Matt's reminds like a fancy word for basically four guys that all have kids that are really committed to them, but also run businesses. And we get together about every 45 days and just give each other a feedback. And on top of that, where it's one of the closest, closest group of people that have ever been part of anything that anyone in there needs, I will do. And you know, I feel like vice versa. In February of 2017, you guys looked at me and I use the plural. If everyone takes credit for it, obviously it worked out. They don't take credit for all that. Stop. Say, you guys looked at me and you're like, listen, anytime that we describe you to somebody, we describe you as our unfair advantage. It's like, what do you mean by that? I said, well, if we want to get media, if we want to find like a launch partner, a vendor, like you're able to just like kind of text somebody and all of a sudden it's there. And so I thought about it more and more and, you know, we explored it and I'm very good with people that I trust at taking advice and implementing. That's one thing that I can say about myself and, you know, I took that really to heart. And then I'd helped our friend who's also in it, Todd Herman, I'd helped him a lot that year with 90 to his big event. And he's like, you got to do this. You got to like put your stuff together and do an event around how to build these win-win relationships, how to connect entrepreneurs to the media and all that. So I wound up doing that as an event and it was amazing. It was like a one day thing was, I did not, wasn't expecting a business around it. One day thing teach people how to do the stuff that I do, bring in people from the media, help them make connections and not around pitching themselves but around creating a relationship. So again, going back to what I had been doing for a song, it was not about like going in and pitching myself to people. It was like, all right, figure out what I can do to help them. And then as a result, they wanted to help me. And, you know, there's a law of reciprocity. Like if you do something good for somebody, it has to come back to you. It doesn't have to come back to you from that person. It's got to come back to you. And then there was no business around it. And I just did that in the middle of like Todd's like three day, two day thing and he had an extra day. And so we did that together and I did another one. And now it's turned into a three day event, you know, that we do. And it's just this amazing thing built an absolutely beautiful company. And when I say beautiful, come in, I don't mean that in a bragging way, but like of people that I love working with, my colleagues are absolutely amazing and clients that I'm just like we help people that don't really aren't. They're really good at what they do, but they're not good at telling people about that. And my belief is that those are the people that need the world needs. And they're just amazing, amazing people. And I love like I feel so unbelievably grateful because I know what the alternative is like. And I say this every Friday, we do a weekly wins call with my company. And I say it every Friday, I'm like, it's I'm so unbelievably grateful to get to work with you people. Doesn't mean anything's ever perfect or anything like that. But I know, you know, when I was able to really, I think consciously create that too. Yeah, I mean, it's interesting because it's sort of like you. The thing that got you out of a really dark place, then woke you up to the power of just being with other people who see the world like you. And then turned into this thing, which now becomes your living in your form of service. And I think it's really fascinating to me to see how like knowing you, you know, like pretty well for a number of years now to see how your devotion to doing the work every day on yourself. profoundly informed. I think it's so important for me to see also. And because I'm constantly struggling with this is to know that, you know, like when you have the opportunity to create something and form a team and build a culture. That it's always just a reflection of your own inner life. Yeah. And your own inner work. It's been interesting for me to see how like knowing your history, you were you created and were part of an organization where a lot of things were toxic. Yeah. You know, that melted down. Yeah. You melted down along with it. And when you when you've had the chance to to birth something new, it's almost like it's like a, you know, it's like the the George Costanza thing. It's like the opposite thing. It's like you look back at like all the choices that you made like everything that you did, like back then, it's like, what is the opposite of that? And that's what I want to create now. What's interesting to me is that both as somebody, you know, like a friend, but also an entrepreneur and somebody's worked a lot on entrepreneurs is a lot of people think that. But when it comes to executing and building, there are a lot of market tensions that that try and pull you away from it. Yeah. Conflict. So staying to that core of values and beliefs and practices is really hard. So it's interesting to sort of see you navigate that. Yeah. And it's something that we keep getting better and better with. So we have like different rule. This was something it just came up recently where it's like, don't settle. So what I mean by that is that we had a couple of different opportunities. We're constantly hiring people and where I was like, Oh, this person is really good. Except it's not like 100%. Like, yeah. And we're like, you know what? Don't like any time that I've had that, it's never really worked out. So like just like, it's like that whole thing of trying to get over like the short term, like relief of from pain or whatever the pain is to, you know, for the shortcut. And you know, same thing with clients. Like we have something I learned this from my friend David Nagle is like, if somebody on the team, like let's say there's some client that one person's unsure of a potential client. Somebody can just pull a red card and no questions asked. We can't take that on. Now as somebody who like loves sales and loves like, that's hard. But it works. It like, if he gets you just keep getting closer and closer, there's a lot of people out there. You know, there's a lot like if you come from the abundant mindset, which is not my default, you know, that's had to become like an after work at it. Just like you said, because I start over every day and fear and, you know, all these different things. And but if you come from that, it just, it's unbelievable. What winds up happening? Yeah. And it is a practice that's not my natural default. I know people were that's kind of their default and like, man, I wish I could wake up in the morning and just see the world that way automatically. And I'm like, but I don't, but I do in general, like through making it. A practice. So it feels like a good time for us to also start to come full circle. So hanging out here in the context of this container called good life project. If I open the phrase to live a good life, what comes up? The first thing that came up was to be of service. Now again, that's not my default. If you would, so it kind of makes me laugh to say that because that's not what I thought. Like I, I didn't think that was the case. But when I realize when I'm at my happiest is when I'm not thinking about myself. Thank you. Thank you so much for listening. And thanks also to our fantastic sponsors who help make this show possible. You can check them out in the links we have included in today's show notes. And while you're at it, if you've ever asked yourself what should I do with my life, we have created a really cool online assessment that will help you discover the source code for the work that you're here to do. You can find it at sparkotype.com. That's S-P-A-R-K-E-T-Y-P-E.com or just click the link in the show notes. And of course, if you haven't already done so, be sure to click on the subscribe button in your listening app so you never miss an episode and then share, share the love. And if there's something that you've heard in this episode that you would love to turn into a conversation, share it with people and have that conversation. Because when ideas become conversations that lead to action, that's when real change takes hold. See you next time.
Podcast Summary
Key Points:
Chris Winfield grew up in Tuxedo, New York, near extreme wealth, and developed a belief that money equals happiness, driving his ambitions.
His upbringing emphasized constant activity and responsibility, leading to guilt and shame around rest, a pattern he still struggles with.
After college, he entered the dot-com era, working for a troubled web development company, which exposed him to dysfunction and disillusionment.
The 9/11 attacks served as a turning point, prompting him to leave and start his own business focused on marketing and driving traffic, not just building websites.
His later recovery from addiction led to a journey of rediscovery, rebuilding his life intentionally and launching ventures like Unfair Advantage Live and Super Connector Media.
Summary:
Chris Winfield, a friend and fellow New York City dad, shares his journey from a driven, successful entrepreneur to a recovering addict who rebuilt his life with intention. Growing up in Tuxedo, New York, near the wealthy gated community of Tuxedo Park, Chris internalized a belief that money equals happiness, feeling shame about his family’s relative lack of wealth from a young age. His upbringing was marked by constant activity and responsibility, with parents who emphasized exercise and work, leaving him with a lingering guilt about rest and stillness.
After college, he stumbled into the dot-com era, joining a web development company with unstable partners, where he excelled at cold calling but grew disillusioned with the industry’s empty promises. The 9/11 attacks were a pivotal moment, prompting him to start his own business focused on real marketing and driving traffic. Despite his success, he struggled with addiction, which eventually caused his business and life to implode.
In recovery, he embarked on a journey of self-discovery, learning to value connection as his greatest strength. This led to launching Unfair Advantage Live, publicity events for entrepreneurs, and Super Connector Media, a venture dedicated to helping people share their unique gifts. Chris’s story highlights the dangers of equating wealth with happiness, the importance of intentional living, and the power of service and connection in rebuilding a meaningful life.
FAQs
Chris Winfield is an entrepreneur and friend of the host who co-founded a creative agency in tech, faced addiction and business collapse, then rebuilt his life through recovery, leading to ventures like Unfair Advantage Live and Super Connector Media.
Chris grew up near the wealthy community of Tuxedo Park and believed that people with money were happy, which drove him to chase wealth for years, despite knowing some wealthy people were miserable.
Chris was raised with a constant need for movement and responsibility, rarely allowed to be still, which led to guilt and shame around relaxing even as an adult.
Chris's sister introduced him to a family friend starting a web development company, where he made cold calls to set appointments, a job he hated but excelled at, leading him to later avoid cold calling forever.
After 9/11, Chris's employer stopped paying staff, prompting him to leave and start his own business, using lessons from his failed experiences to focus on marketing and driving traffic.
Chris launched Unfair Advantage Live, a series of publicity events for entrepreneurs, and Super Connector Media, a venture focused on helping people share their unique genius with the world.
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