The Outworker
The relationship with oneself is the most important to develop, but the easiest to neglect. These conversations will hopefully allow you to develop that relationship.
The Outworker
#028 - Chip Skowron - Insider Trading On Wall Street To Inner Healing In Prison
From Wall Street to prison walls, Chip Skowron's life took a dramatic turn when insider trading brought his hedge fund career crashing down. Chip reveals the actions that led to his crimes and the harsh reality of facing the consequences. He shares how prison became an unexpected crucible for transformation, forcing him to confront his past and forge a new identity. Now dedicated to prison reentry, Chip offers a raw, honest look at redemption, second chances, and the challenging journey of rebuilding life after losing your sense of self.
Timestamps:
00:00 From Wall Street to Prison: A Life Transformed
00:41 Feeling Different As a Kid
02:53 Dealing With Addiction
06:19 The Impact of Loss and Expectations
12:41 Medicine to Finance and Identity Shifts
22:01 Insider Trading Incident
34:30 Lessons from Prison: Education Beyond the Classroom
42:27 Reintegration: Challenges of Returning Home
48:30 Embracing Vulnerability: The Strength in Being a Mess
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What’s up Outworkers. From Wall Street to prison walls, Chip Skowron's life took a dramatic turn when insider trading brought his hedge fund career crashing down. Chip reveals the actions that led to his crimes and the harsh reality of facing the consequences. He shares how prison became an unexpected crucible for transformation, forcing him to confront his past and forge a new identity. Now dedicated to prison reentry, Chip offers a raw, honest look at redemption, second chances, and the challenging journey of rebuilding life after losing your sense of self.
Tim (00:02.191)
Chip, welcome to the show.
Chip Skowron (00:03.8)
Hey, thanks for having me. It's good to be here with you.
Tim (00:07.471)
You use drugs as a kid, not just a way to fit in, but because you felt different and you wanted something that would counteract those feelings. And you've said, I knew from a very young age that my brain didn't work like a lot of other people's brains. And I recognize that I felt like I wasn't fitting, fitting in. What did it feel like having that high level of self -awareness as a young kid?
Chip Skowron (00:36.065)
Well, it didn't feel like self -awareness. It just felt like isolation and loneliness. I think it's an interesting question. Self -awareness, I think, can come with a lot of flavors, I suppose. And for me, at that young age, physically being
smaller than a lot of the kids that I was in school with, feeling like I was somewhat distant from them relationally, it was hard. It was really hard. I think for most of the significant growth periods of my life, self -awareness came with heart.
You know, including and arguably most importantly around the situation that led me to prison. You know, I was coasting along, arguably very numb to the patterns of behavior that I had become very comfortable with that were very destructive. And self -awareness actually brought me to Christ. It brought me to faith.
Tim (02:01.881)
Yeah, I think the thing with self -awareness just at a young age, especially is that it can be a double -edged sword where you do have that awareness of how you're feeling, but that can lead to feelings of pain and discomfort and those feelings of being different. At what point did your drug use turn from, this is something I'm doing just to try to fit into
Okay, now this is something that I'm addicted to and abusing.
Chip Skowron (02:36.03)
That's a good question. My medical training has a list of criteria that are required in order for you to be deemed addicted. think just qualitatively in my case, not long after I started
experimenting with marijuana and using alcohol regularly, I would say it became a very significant problem for me because I was depending on it. I was looking for it as a pleasure. It became actually a very significant priority. I used to order my days around it.
Yeah, I mean, looking back on it super dark time and yet a lot of people who were very close to me, including my parents, really unaware of how
how broken their son was.
Tim (03:49.829)
When you went to Vanderbilt for your undergrad degree, what was it like being in that new environment, especially being on a college campus where alcohol and drugs could be obviously more readily apparent and more easily to be surrounded by it?
Chip Skowron (04:07.9)
Yeah, I mean, to a certain extent, I had been immunized from some of the really significant temptation on campus, but I was really interested in the fraternity scene. Again, so wanting to fit in, wanting to be accepted, and found a group of guys there that were also
extremely bright, had very unique giftings, each one, and really an amazing group of people. And, you know, found myself really looking to, let's say, succeed relationally, to be popular, to be celebrated in that area, and made a decision to try to do that.
ultimately became the Rush chairman, know, Eric Stratton, Rush chairman. Yeah, I'm glad to meet you. I that was, I wanted to be that guy. And,
Yeah, so many pitfalls, so many places, so many times where it could have gone much, much worse for me. Had I not had this very distant goal of becoming a physician and knowing how challenging and competitive that journey was, I don't think I would have made it through college. I really don't.
Tim (05:46.715)
diving deeper into that and something that your mom would always tell you to those that much is given much more is expected. How did you become or how did that become deeply ingrained in your makeup as a person, especially after she tragically died in a car crash at 52?
Chip Skowron (06:10.669)
It's interesting, Tim, you know, I'm really, I want to celebrate the fact that you've done so much of your homework here. I mean, it's, it makes this a much more meaningful conversation. You know, the words of scripture, when they've been spoken to me, have always found a seat in my soul. It's just a matter of circumstance that allows those words to suddenly become
really, really present. And I guess for a very long time in my life, those words, which basically created a significant burden, right? I knew I was given much. People had told me I'd been given a lot, but also I knew intuitively in my own awareness that I'd been given a lot. So I need to thrive. I need to perform. I need to measure up.
And measuring up was going to be something that in combination with the way my dad was brought up and the things that he had poured into me, measuring up meant I was going to perform. There were very hard measures and expectations put on me with regard to GPA and performance on a soccer field or whatever I was engaged in. I was expected to do it.
100 % excellently. And it wasn't until much, much later that I began to realize how those words had been interpreted by my own mind in a way that was not the way that those words were intended.
Tim (08:00.879)
Do you think you were more driven by fear than by success?
Chip Skowron (08:07.497)
There's no question that after my mom died, I was very, fearful of my own thoughts and emotions. They often overwhelmed me and it became something that I actually tried to run from. I think that as a young man, I don't feel like I was fearful. My sense was not that I was a fearful young man, timid in any way, but
But there was a desire to perform, for sure. There was a desire to win my father's approval and to be adored. I mean, I certainly wanted those things. Fear came later.
Tim (08:53.391)
getting into that theme of metaphorically running away. You said this set me on a trajectory of running because I couldn't stop. If I stopped running, I would have to face those sorrows and the sadness. And you've kind of already alluded to this already of having that distant goal and that mission of becoming a physician kept you on that path. How did work become almost a coping mechanism for you?
Chip Skowron (09:21.323)
Well, mean, yeah, you stay busy. You don't have the silence where your mind can wander and you have to be present with your own thoughts. You know, especially I had never experienced the kind of sadness that my mother's death brought. It was overwhelming. It would be like a wave crashing over my entire mind and would sometimes
leave me relatively paralyzed for even more than a day. And I found that if I could stay busy, that the likelihood of that happening was diminished. And you know, I mean, there's nothing unique about my sorrow. mean, I've had lots of conversations with people who are dealing with all kinds of sorrows in their lives. And they all kind of describe more or less similar experiences. I think my coping mechanism
of focusing on work became a place where, yes, I could stay busy, but I also achieved. And so I was also satisfying some of those other desires. And look, if I had not had a dream of being a doctor, of being that kind of a person in my society, I mean, I could have easily gone down the road of becoming a drug addict and, you
There's no limit to how low I could have sunk. And so, you know, I mean, there but for the grace of God go I, you know, so I have, in a very real way, I've tasted the kind of sadness that can lead you down a very, very dark path. And I would be there were it not for these other situations and circumstances in my life.
Tim (11:18.523)
diving deeper into that. So in September of 1990, during your senior year at Vanderbilt, Dean Leon Rosenberg from Yale Med School calls you on the same day your mom dies and offers you a position in Yale's medical science training program. And then obviously you're dealing with a lot of emotions with your mom dying or I guess a better way of saying that is
maybe not dealing with those emotions as much, kind of running away from those emotions. And then after Yale, you went to Harvard for a five year residency program in orthopedic surgery. I know you didn't finish the program. You stopped after three years, but how early into the program did you start having your doubts about it?
Chip Skowron (11:59.928)
Okay.
Thank
Chip Skowron (12:12.061)
I had no doubts initially. I was exactly where I was supposed to be. This was the culmination of my life work. It wasn't until our first child was born and my position as a resident really was put into the context of now I'm also a father.
And from all of my life up until that point, I was largely living for myself. And now I had this other life in addition to my wife, who I was falling very deeply in love with. And it changed. It changed the way I thought about a lot of things, not just my career. And I was still running from the fallout from the...
the sadness and what I perceived was an abandonment by God around my mother's death, but this sweetness, this sweet, precious life that had been given to my wife and me, I really wanted to do right by it, by her. And that was a huge factor in leading me to make the decision to find something else to do other than
pursue and finish the residency.
Tim (13:44.345)
there any other fields besides finance that you were looking to get into?
Chip Skowron (13:49.679)
Yeah, I looked at consulting, so sent applications to Bain and McKinsey, and I looked at going into industry. So there were lots of orthopedic companies that I entertained going to, like Zimmer and Biomed. And it was a relationship that introduced me to this idea of going into finance. It was not my own idea. And then that is what ultimately brought me to New York and an interview at SAC Capital.
Tim (14:19.643)
So what did that transition look like for you?
Chip Skowron (14:22.828)
Very abrupt. Almost what it felt like was I left the operating room on Friday and I sat down at a training desk on Monday morning. That's what it felt like. And felt super inadequate and ill -prepared. And like I was desperately trying to keep my head above water and...
reading and processing and digesting as much information as I could and talking to as many people as would answer my questions. It was hard.
Tim (15:00.837)
how long into getting into that space did you start to feel like, all right, I'm starting to figure this out a little now. You know, I know what I'm doing here.
Chip Skowron (15:14.649)
I don't know that I ever felt like that. You're always paying tuition to the street. I think I got the sense that what I could do was able to position something in the marketplace that would have value, that would resonate with investors. And I think it was about a year and a half, a year and a half into it. It was a really rough year and half though.
but I also importantly had become much more aware of the skill sets that were required in order to actually execute on that type of a plan. And I knew and had gotten to know people who were able to, you know, compliment what I was bringing to the table in a way that would allow us to be, I mean, I thought we would be successful.
Tim (16:13.797)
How do you think your identity shifted from being in the medical space to, right, now I'm a hedge fund guy working on Wall Street?
Chip Skowron (16:24.663)
So it's subtle, know, as a surgeon, what makes you great most of the time in orthopedics is your prowess in the operating room. If you're great with patients, that's okay. But what the community celebrates is, you know, you can do a third revision of a hip in 45 minutes and you...
you don't have complications. It's quite more technical. In finance, well, there's the obvious, very direct and clear measure of performance, which is your returns. So there really isn't any ambiguity there. The direction that we had gone, there was another very important quantitative measure.
of how good you are, which was your assets under management. okay, so your performance is not top -decile, but if you're managing three, four, five billion dollars, you're still, you know, like that. And so, my ability to perform shifted from, okay, I'm gonna be the man in the operating room.
I need to have these external objective, you know measures of my success of our success demonstrate that we're really good and and then of course my position in our group as a portfolio management more as a face of our organization I needed to know what I was talking about
and I needed to do a really good job of convincing other people that I knew what I was talking about. And medicine had really prepared me for that. If there's anything that they, I don't know if there's anything, if there's one thing they teach you in medicine is that you should portray the idea that you are seldom wrong, but never in doubt. And that's really something that I brought to the table as a portfolio manager.
Tim (18:44.505)
Yeah, obviously your professional identity changes from that standpoint of what success looks like on a personal standpoint, understanding yourself as a person, just sort of deep down. you feel like there was any identity shift there?
Chip Skowron (19:01.62)
Well, you know, at the time when I decided to be a doctor, when I decided when I wanted to be a doctor, this is going back to when I was 10 or 11 years old, being a doctor was the most noble thing that you could do in the community. That was really the person who had respect and dignity and people looked up to them.
By the time I was working as a resident, that had largely changed. And at that time, certainly one of the new types of career that people thought of as being kind of the best of the best was being a portfolio manager, being a fund manager, especially at a hedge fund. These were the, you know...
the masters of the universe, as Tom Wolfe would say. And so, in a sense, my focus had shifted to still trying to be the most well -respected, best version of what our society honors. And again, completely ignorant of
ideas like purpose and calling and who was I created to be. Just not even, those aren't even on the table as questions that I was asking myself.
Tim (20:41.189)
Can you provide a brief summary of what exactly transpired with the insider trading just to set the table?
Chip Skowron (20:49.125)
I mean, simply put, I was very focused on new and emerging therapies. One of those areas was hepatitis C. I had developed a network around the world that was involved in the development of these new therapies. I received a phone call from a doctor in Europe who had just found out that three patients had died in a particular clinical trial.
And that particular trial was being conducted by a company that we had a comparatively very small position in, but it was a small company. So we began to sell that stock as a result of that information. We sold for probably three weeks or four weeks. But at the end of that selling period, there was a
there were some catastrophic market events that were happening in the world. And so we just decided to punt that remaining position and the people who bought it happened, just happened to buy it on the day before the news came out that we had found out about weeks before. And they were upset and called the SEC. And that's what led to my pleading guilty for conspiracy, what was conspiracy to commit.
securities fraud, which is the statute that people call insider trading.
Tim (22:21.563)
So in an ideal scenario, you get that phone call from that doctor with that insider information. What is it that you're supposed to do to stay within the confines of the law?
Chip Skowron (22:33.369)
Well, I mean, by today's the definition of insider trading has changed. It's all based on statute. So by today's standard, that would probably not be considered insider trading. But at the time, if you wanted to, let's say you were a super strict regulation observing guy,
You would have called not your trader, you would have called your legal counsel and said, look, I just became aware of material nonpublic information for this company. I'm unclear of the source. We need to restrict our firm from trading in that stock until we can get this restriction lifted.
Tim (23:23.119)
I was certainly intoxicated by the world I was living in and to a certain extent I was aware of it, but I definitely was not going to be able to save myself from it. There was no way I was going to rescue myself. Obviously a much different scenario after the insider trading takes place. But before that transpired, why don't you think you were able to save yourself?
Chip Skowron (23:47.114)
Well, mean, the money was good. My reputation was exactly what I dreamed and hoped it would be. The position I had in my community and the position that I had even in my own life with regard to my wife and my children and, you know, all the bells and whistles, all the accoutrements of life, you know, I...
those things, notwithstanding the fact that I was deeply unsatisfied with my life, there was no way I was just going to walk away from that without a reason to.
Tim (24:34.811)
So in September.
Chip Skowron (24:34.953)
I just didn't have that in me.
Tim (24:38.105)
Yeah, it's almost like the bandaid had to be ripped off by somebody else.
Chip Skowron (24:43.293)
Exactly. And that's exactly why, Tim, you know, when I look back at my events, the events that transpired and what happened, I see a grace from God in my life. Had he not intervened, had he not ripped the bandaid off, I mean, things were not going in a good direction.
Tim (25:09.103)
Yeah, I mean, I've experienced it in my life as well in a much different setting, but I think a lot of people experience this where you have to be put through stuff unwillingly or against your will for you to find gifts or be put on a path in life where you see this higher purpose that you wouldn't have necessarily even gotten on that path because you wouldn't willingly be putting yourself in those difficult situations.
In September of 2009, that's when you become aware that you were being investigated. What did that investigation look like? And then what did the legal process look like?
Chip Skowron (25:49.169)
September 2009. so initially it was a civil investigation and the civil investigation was, know, our lawyers told us related to this trade and there was an investigation that looked at all of our text messaging, all of our emails, all of those things.
And as the lawyers, know, very, very, very well paid lawyers went through all of those things, they became convinced that there was no smoking gun. There was no nothing in all of that, that actually would have been a meaningful admission. And so in the conversations that we were having around the investigation, you know, we were encouraged like any defense counsel would encourage you to basically say, listen,
unless you have very, very specific memory of these events that happened years ago, you need to say, don't remember. so, look, I was a I was a pretty arrogant guy at that point in my life. And so, you know, I felt like we were gonna be well protected. I did not have any idea, none of us did.
that this was going to go down the path of something criminal. And so it really was something that just kind of became very, very compartmentalized. was not some other people were handling it. We didn't have to get involved. And, you know, in November of 2010 on November 4th, I believe that was the day that suddenly all that changed. And
That was very dramatic.
Tim (27:42.445)
And what happened on that day?
Chip Skowron (27:44.625)
Well, that's when the doctor who made the phone call to me was arrested at the airport getting ready to fly back to France.
Tim (27:53.861)
Gotcha. What do you think that arrogance stemmed stem from for you?
Chip Skowron (28:01.223)
you know, for years I'd been told you're the man. you know, certainly arrogance, and, and, you know, all the things that are related to that narcissism and, know, I began to believe my own BS and, you know,
Yeah, I think there were a lot of people that, maybe even most people, just didn't even, wouldn't want to be around me. I was pretty toxic.
Tim (28:35.258)
I find your what you say to the judge incredibly fascinating. Your honor, I was not aware of the changes that were happening in me that blurred the line between right and wrong. They came slowly over several years. I allowed myself to slip into the world of relativism where the ends justified the means. Quite frankly, it's very hard to imagine how I became that kind of person. What are your thoughts now reflecting back on that and hearing that?
Chip Skowron (29:06.275)
I mean, I think that insight that I had then, I think that was the direct result again of the grace. And I see how important it is in my life today to not allow myself to drift in that direction. I was writing about temptation today. Temptation and are different things. No one gets
out of life without being tempted. All of us are going to be tempted. you know, whether we give in a little or a little more, you know, the thing about it becomes the more you allow that sin into your life, the more numb you get to it. And, you know, I can see how if I tell a lie today,
I don't know how long, but ultimately the end result of that is there isn't any deplorable act I'm not capable of.
So, and by the way, I'm not arguing in favor of legalism and morality. I'm just speaking in terms of the temptation to take a shortcut to get to this thing that I desire, whatever that thing is. And, you know, we talked about having, I had this goal, this desire to be a physician, and it carried me through, and through circumstances and through addictions that would have destroyed me.
You know, what's carrying, what is carrying me through today? What are my eyes fixed on today that will allow me to stay on that path? Knowing that in my flesh I'm gonna weave and deviate off of it. But what am I fixing my eyes on? And if it's something worldly, it's not the highest. Right? There are things that are beyond this world, eternal things.
Chip Skowron (31:12.397)
that if I fix my mind on those things, then the impact on how I behave today becomes radically transformed. I start to look at people differently. I look at my circumstances differently. And I can overcome in ways that I wouldn't be able to otherwise.
Tim (31:29.221)
That's really well said. What was your sentencing like when you got convicted?
Chip Skowron (31:37.049)
well, have you ever stood before a judge?
Tim (31:41.679)
Thankfully I have not and I don't plan on doing anytime soon, soon or hopefully never in my life.
Chip Skowron (31:48.285)
Everyone will stand before a judge.
And I had the opportunity to stand before a judge in this life. I hope, Tim, you never have to stand before a judge in this life, but if you do, and you know that that judge is a man and doesn't know everything about you. It caused me to think about my life in ways that were really profound. Ultimately,
I am going to stand before a judge who knows everything about me. Every Google search term, every thought, every action done in secret, he knows everything. And that's quite a different standard than standing before a judge who's entertained the idea of sentencing me for insider trading. So I did not get sentenced for everything that I've done. That judge doesn't even know.
everything that I've done. If I were sentenced for everything I've done, I'd still be in prison or worse. yeah, standing before a judge is a very sobering place to be. I know hundreds, if not thousands of people who have stood before judges, and I love talking with other people about that moment. It was profound. It was hard.
Tim (33:22.555)
So you went to prison January 2012 and you said it was the best education of your life. Why was that? Why was that the case?
Chip Skowron (33:33.898)
Well, most of my other education was really centered on, I mean, not all of it, but a lot of it was centered on basically pouring facts into my brain, especially medicine, right? mean, medicine is largely about learning a whole new vocabulary and a whole bunch of definitions of those words, but there's other parts of it too. But this was an education that had much more to do with relational dynamics, with power.
with
what it means to be human, what it means to be a man, purpose, calling, gifts, how to grow and develop my gifts. Those are the things that really position me as a man to become what I was.
created to be. All of the education that preceded that was about a vocation largely.
Tim (34:45.839)
Yeah, what I find most interesting about that is, well, the first thing is that you've said that that first night in prison was the first peaceful night's sleep that you had in years. I find that very fascinating. And like you had said, you had always been in very high performing, high caliber environments, whether it was with medicine or in finance. What was it like now being in an environment where
You weren't necessarily trying to excel or play that professional game, but it was more so just about existing and being.
Chip Skowron (35:25.723)
Well, it's interesting you say that because, you know, probably it took me probably eight months or a year before I really got into prison. So mentally, you know, you're still kind of straddling the fence. You're trying to still, you know, wrestle with circumstances on the outside.
But after about a year, I settled into being in prison. And it allowed me to really begin to absorb the richness of what that environment had for me.
It's not that I wasn't trying to excel. was still trying. I was, still very determined to do anything that I'm doing excellently. And I'm not saying I was trying to be the best prisoner I could be, but I was really trying to utilize that place and that time maximally for how it would benefit me. There emerged probably not surprisingly, a very deep desire.
to not have this disaster be wasted.
And so I wanted it, I still want it to be redeemed. A lot of people got hurt. A lot of people got hurt.
Tim (37:03.515)
I like how you say that though, a disaster not wasted.
Tim (37:09.467)
How important were the other prisoners that you were in prison with for excelling and making sure that you were doing that internal examination work and making sure that this disaster didn't go wasted?
Chip Skowron (37:23.364)
Vital. They were vital. You know, on one extreme, you might imagine if I'd been put in solitary confinement for the whole time, would I have benefited? I mean, I probably would be insane. And we know that actually probably happens many, times. So for me, the relationships that were put into my life
along the journey inside prison were vital to what I got out of it. From the first person I met, whose name was also Chip, is also Chip. He's still a very dear friend. from that person, including the corrections officers and the administration and the other prisoners and
you know, all the circumstances that we experience together and the challenges that we face together and the challenges that we created for one another and the...
how we stood by each other or didn't stand by each other. All of those things were all used for the good.
Tim (38:44.877)
Restoration is relationship. What does that mean?
Chip Skowron (38:50.828)
Well, so what I mean when I say restoration is relationship is that it's really through relationships that I find my...
my healing, my growth, my purpose, know, my creator.
built me uniquely for accomplishing the things that he has for me to accomplish. And at the end of it, it is not that the work was done. It's the relationships that were part of that whole journey are the, they are the wealth of the life lived. And ultimately being, you know, back with God,
at the end of it is all that matters. So I guess whether it's with my brothers or sisters, certainly my wife, my children, my parents, like all of those relational contexts all have really profound meaning for me. I'll tell you, know, in my journey in prison ministry,
There's no other conversation that you can have with a group of men in prison that will bring up stronger emotion than a conversation about fathers. If you bring that conversation up, you need to be ready for all kinds of fireworks. And if you think about
Chip Skowron (40:46.098)
our lives, you know, and the importance of a father in our lives, right? That, I mean, might not be that surprising, but then when God presents Himself as a father, right? You can understand the importance of that. so, yeah, that's, are the thing that I really work hard every morning at focusing on so that my day is oriented that way.
as opposed to lists of things that I need to do.
Tim (41:19.483)
So you build those strong relationships and that strong network in prison, and then you get released in 2015. You have to leave that environment and you have to leave that network. What was it like being a new man and evolved man, but then going back to an old environment?
Chip Skowron (41:40.128)
Good question. That is largely the struggle of my journey that has made the seat that I'm in now at the Prison Entrepreneurship Program so meaningful to me. Because coming home in a very unanticipated way was the hardest part of the whole process. Certainly coming home to children
two of which don't even remember their dad before he went to prison, but also my wife and the damage that I had caused in my marriage that needed still a lot of work and needed to be healed. Coming back to the community where people had lost their jobs and it was a very, very public embarrassment.
Those were all challenging. what you're talking about, so I left a community that was so...
vital to my soul food. I was being nourished in a way in prison that when I came home, I have struggled for almost 10 years now to get that kind of soul nourishment again. And I think here at the Prison Entrepreneurship Program, I found
a group of people who are deeply committed to creating that kind of community on the outside so that when our brothers come home, they actually find that community here too.
Tim (43:35.461)
Do you ever reframe it in a way where you try to see it as, God gave me this journey and this battle because he knew I could be a person to fight this fight.
Chip Skowron (43:50.095)
I don't know that I'm fighting the fight. I I hope I'm doing well by him. But I believe that there's an entire generation of leaders that are either in prison or have come home that are largely disenfranchised. They are, you know,
certainly not afforded the same kinds of opportunities that I would like to see them afforded. And there are leaders and people there that are going to be powerful instruments of healing for our community and our society that so desperately needs to be healed. They're gonna play a vital role in that. And I am interested in opening the door, if I can be a conduit for
them to be able to participate in that dimension of the healing of our community and our society, that's what I'm focused on doing. To the extent that I can be used in that way, great, but I really see the opportunity in pouring into that.
Tim (45:06.861)
One thing that I've noticed is that when I was researching you and when I was looking at images of you and seeing the difference between where you were when you were working in finance to where you were now, and you've spoken about this earlier, how, you know, when you were in finance, you had gotten to a point where you were toxic. You were arrogant.
And I would, when I see images of you from back then to now, one, it almost looks like you look like Gordon Gekko to a certain extent back then. But you just obviously have this much different physical appearance, but you can almost sense and you can feel a different energy by just the way that you look and the way that you smile.
Chip Skowron (45:38.722)
Yeah.
Tim (45:55.749)
Do you feel a difference in energy? And if you do, what does that difference feel like?
Chip Skowron (46:01.367)
Well, don't, I mean, so you're referring to my hairline being a lot higher now? I think I've learned to laugh a little bit more freely. I think that there were a lot of wounds in my soul that needed to be healed that I was carrying around with me.
I don't have the same kinds. Let me say it this way. I had a lot of secrets back then, secrets that I needed to keep secret, that if people knew the truth about who I was, I knew that they wouldn't want anything to do with me. I don't have those secrets today. And so there's a freedom.
that comes from not being bound in that way anymore. And I think that's probably a big part of it.
Tim (47:09.849)
Yeah, I think that's a great way of saying it. And like I said, when I would see the two images of you from back then to compare to comparing it to you now, you do look like a much more healed and free version of yourself. What I love most about your story that I've heard you speak about is how and also just with stories in general, it's easy to think or see these massive transformations.
Chip Skowron (47:24.993)
Thank you.
Tim (47:39.643)
and have this understanding of, look what I've gone through. And now I'm this perfect image. I'm this perfect man. But you still deal with a lot of challenges and struggles and you actually emphasize the exact opposite. And you've said, I'm a mess. And I've heard you speak about it before, where you're in front of a large group, just allowing people to have that freedom and that acceptance to
tell the people around them like, hey, I'm a mess. And having that type of vulnerability is a true strength. How do you think your understanding of yourself as a mess has evolved over the course of your life?
Chip Skowron (48:24.371)
Well, I guess I mean I thought in the early days that I was a mess and I was responsible and you know I'm a mess and that's embarrassing. I don't want you to see my mess But now I have a different identity, right? It's I'm I'm actually God's mess and he is deeply interested in me regardless of my mess he wants
to love me and be close to me and he's not surprised, he's not disappointed. then, you know, seeing more fully my own mess allows me to love people who are also in the midst of their messiness and to not feel compelled to kind of pull them out of it as much as to go be with them in the midst of it.
and to be present to them. So I don't have the same biases and prejudices. And quite frankly, I am well aware that I might be blind to biases and prejudices, but I can tell you this, I'm determined to get those things, to the extent that I become aware of them, out of my life. So I don't want to have any limitations.
in terms of how God might use me to love someone. I think about Jesus going into the cemetery where the demoniac was chained up, and people are like, why in the world would that rabbi go there? That's kind of where he calls us to go, to go into the deep, dark places and find great value there in people.
Tim (50:22.573)
If you had to go back when it came to the insider trading, would you change that or would you keep it how things transpired?
Chip Skowron (50:31.206)
I mean, look, I look back at my life and a very wise man once told me that eventually I will look back and have the greatest regret for the moments that I didn't love someone when I had the chance to. And I can tell you that's been a very, very profound insight for me.
When I think about the things that I've done either out of selfishness or fear like this insider trading, the idea that I would change something that would prevent those things from being burned out of my life is utterly ridiculous to me. Now, understanding that a lot of people got hurt and there was a
there was a price to pay. And it wasn't only born by me, right? My wife and children and many other people lost their jobs and a lot of damage was done.
But for me, to be able to see how far the Lord has brought me from that guy to today, no, I wouldn't change a thing.
Tim (51:57.157)
ship, can people go to support you and your work?
Chip Skowron (52:00.953)
Well, mean, gosh, the New Canaan Society was a huge part of my journey. The New Canaan Society is a collection, a movement of men across the country. And newcanaansociety .org is an amazing place for men who are going through it to find a community of people who are just gonna love in the midst of all of that. And then,
You know, look, if people, my expectation is, as we have a further awakening of the church in our nation, there's gonna arise a desire to go be with the people on the margins of our society. And in my case, I'm just drawn to the prisons. I love being there, it's my safe place. so, pep .org, prison entrepreneurship.
program .org is one of those extraordinary stories. It's a 20 -year story of a community being built around human flourishing, and especially the flourishing of people who are coming out of prison and executive volunteers who are loving them. So it's a really fun place to be. And I would love, Tim, to take you to prison with me,
And you're just not going to be able to spend the night. That's the only problem.
Tim (53:31.749)
think I'd be fine with that, but yeah, that'd be great.
Chip Skowron (53:34.244)
We'd love to have you.
Tim (53:36.069)
Chip, I appreciate you for coming on the show.
Chip Skowron (53:38.455)
Thank you for having me. It's been a real pleasure and great job. Really loved the opportunity to get deeper into some of these subjects. Thank you very much.
