#004: The Enneagram – Psychologist Drew Newkirk

Thursday April 08, 2021

The characteristics that set high-performers apart fascinate Drew Newkirk, a New York City psychotherapist who uses the Enneagram Theory of personality assessment to help people unlock the secret to achieving their goals. Drew focuses on elite performers’ ability to remain proactive and out front. Rather than being on the defense,  he coaches on strategies to push forward while never letting others bring them down. 

In this episode, Drew joins host Fran Racioppi to share his transition from client to the therapist and how he helps others find joy, happiness, freedom, and fulfillment through a quest to understand life’s purpose. An avid music lover, Drew uses music as a language to connect with his clients, as well as to inspire himself and others. He shares his new docuseries called “The Songs That Saved Your Life” where he explores music as inspiration to those who find solace in specific songs. He also debuts his new YouTube channel where he blends lessons from music and literature.  


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About Drew Newkirk

TJP 4 | Joy And Purpose

Drew Newkirk is a psychologist by trade where he consults with high functioning and elite performers on the behavioral attributes needed to achieve their goals. Drew uses the Enneagram Theory of personality traits to classify behavioral patterns defining core characteristics according to one of nine types.

As an avid music lover, Drew uses music as a language to connect with his clients, as well as to inspire himself and others.

Drew has spent the last seven years developing the concept and producing a docuseries in partnership with recording artist Run-DMC called “Songs That Saved My Life.” The series explores music as inspiration to those who have suffered from depression and suicidal thoughts finding a solace in specific songs.

In this episode Psychotherapist Drew Newkirk dissected the Enneagram Theory of Personality Assessments and how leaders can apply this to their teams. Drew explained the importance of self-awareness in our relationships with others and how the enneagram helps him deal with his envy of Hugh Jackman. We discussed this docuseries, Songs That Saved Your Life. The importance of music, our mental, physical and emotional well-being, and how despite early support from even the largest record labels, he still pushes every day to launch the show. We also lamented on these pre-COVID investments in the restaurant industry after an ill-timed rebalance out of tech stocks but drew says the loss was worth every penny because of his love for hosting.

Drew Newkirk is a Psychotherapist in the West Village in New York City where he consults with high functioning elite performers. He uses the Enneagram Theory to classify behavioral patterns according to one of nine types. He uses music to connect with his clients as well as to inspire himself and others. He spent the last few years developing the concept and producing a docuseries in partnership with recording artist Darryl McDaniels. Songs That Saved Your Life explores music as an inspiration to those who have found solace in specific songs. Drew is also an avid restaurateur, investing in New York City bars and restaurants where he explores the inner workings of the food beverage and hospitality industries.

Drew, welcome to the show. Before we start, I need to let all of our readers know what’s going on. For you, we have this guy who’s about 6’4”, 6’5” maybe 220. You have sleeve tattoos, shaved head on the sides, long hair on the top and a beard. There’s me, clean-shaven, short hair and glasses. When I think about this conversation, you have a Green Beret talking to a psychotherapist but when you look at us, it should be reversed.

I like how you describe me. One, I’m not 6’4”. I’m pushing 6’1”. I’m devastatingly handsome. You did not mention that, which really upsets me, which should be the most intimidating part for you. I’m about 190 because I’ve gone with sleek lately more than buff. I’m older. I don’t need to improve my brute strength or masculinity. It’s about having abs that you can see. It’s the most important thing. Being able to run possibly a six-minute mile when I need to.

You don’t balance the bench press bar off your chest anymore?

It’s all machines man. I do not go near free weights. My joints don’t work the same way.

It hurts now when you do that. I’ve got to say, we first met a couple of years ago in one of your bars down in the Lower East Side of Manhattan.

In which you interpreted me as a 6’4” then?


I must have had so much of an impact that you made me taller and bigger and again, you should have made me more handsome.

I was intimidated, for sure but I was fascinated by your story because when we spoke and you reiterated it when we connected again. You described yourself as a jack of all trades but master of none. That resonated with me because I think about all these things that you’re involved in. You’re a psychotherapist to influential people in Manhattan, a restaurateur, an entrepreneur, a film producer trying to launch this startup docuseries. Music is one of your passions that is ingrained in everything that you do. As I think about this show, I think about the Jedburghs who were recruited across all of the military for a specific set of character traits and skills, but the totality of what they brought to the organization was what made them successful in anything that they did. I really think about you and I’m like, “This is a modern-day Jedburgh, right here.”

I’ll take that.

That’s the offset of getting about 30 pounds above where you are. I got to build you back up. I brought you down a little knot to build you back up. I’m thinking about trying to tell your story. I know that in journalism, they tell you, “We got to put the bottom-line upfront.” In storytelling, they say, “Tease the bottom line out throughout the whole thing save the best part for the end.” There are many places where we can begin this conversation and start talking about you and the things you’re involved in. I feel like if it’s at all possible, we’re going to end up trying to do both of these. We’re going to put the bottom line upfront and we’re going to talk about all these things at different times.

When I start these shows, I do it with a discussion about what my guest has achieved. With you, I want to go deep right off the start. I want to talk about you because you describe yourself as a fighter but you were someone who didn’t have an easy time growing up as a kid in high school into your twenties. It took you a long time to figure out yourself, figure out who you were, what you wanted to be. This fighter spirit consumed you at a young age but it also sets the foundation for all the things that you’ve been involved in. As you’ve described it to me, it taught you that winning was the only thing you wanted to do no matter the challenge. If you would define this fighter spirit inside you, where did it come from? What does it mean to you? How do you use this every day in everything you set out to do?

It’s funny you use that word. It’s probably because I’ve used that word. Maybe it’s an unconscious thing that I do. If I look back even as I describe myself, whether it’s on my website as a therapist, there is that fighting communication that I’m putting out there. That idea is something I’ve moved away from. I grew up in a house in which my father told a lot of stories about his fighting days like experiences in scrapping, the street with tough kids. He got off on it. As a young man or even a boy, I think I idealized that idea.

As a man, especially as I’ve developed and understood myself better, I resist the idea that I am a scrapper because I think that was about being defensive, insecure, feeling small and weak. I tried to have power over people to compensate. Speaking of the high school experience, I was a late bloomer. When I was maybe 18 or 19, I had three pseudo-pubic hairs on my chin. I did not want to shave them off because they were a sign of masculinity. My body was hairless. I had weird nipples going on, which I learned later were nipple knots.

I never heard that.

I didn’t either until I was 32. I thought I had cancer when I was in high school because there are these lumps underneath my nipples that are pretty natural but you go through it pretty quick. It took years for them to go away for me. There was this late-blooming situation that my big mouth when I was younger then caught up with me because now, I am in high school where there’s all this competition for attention. I’m not developing like everybody else but then there were some people who were like, “He was the one with the big mouth. Let’s screw with this guy.” There was a three-year period in which bullying was significant. I would go through the back of the school every day and leave through the back because I did not want to be in a position where I would be taking advantage of, abuse or feel small. That’s what I initially went to therapy for.

I had a few moments in my early twenties and my brother Chris, as you know, is eight years older than me and was there for a lot of them. He was a mentor and he took me under his wing. We would go out with groups of friends. We’d go to New York City. If somebody was looking at me weird, whether I knew what the hell they were looking at in my head, they were sizing me up, considering me weak and vulnerable. Now, I had come into my own. I’m not totally unattractive. I do put myself out there. There is a visual that makes me a target at times. At times there was a target on my back. At times it was somebody looking past me not even looking at me and I interpret it the wrong way.

There were fights that happened that didn’t need to happen. Ultimately a few friends said, “You got to go take care of this. This isn’t healthy. You’re inflating people who you don’t even know into a position of power that they don’t deserve.” It wasn’t like I would fight friends. It’s these random people I didn’t know. Not only was it dangerous but it was the prime reason I started moving into self-discovery. I went and got a therapist. Yes, I do use that word fighting because there is that grit, there is that part of me that still has that, “I will not be taken advantage of again. I don’t want my clients to,” but it isn’t out of a place of power over but from a place of security. Can I be secure and know who I am, therefore I don’t have to overreact but can still be powerful in this world. It’s a long answer.

Let’s talk about purpose. You told me that you know and understand your purpose. Not only do you know and understand your purpose but that you have an understanding of how to represent it in your life and in the life of others. You describe that as being this chair. This chair has four legs. You need all four legs to be balanced. Can you talk about this theory of the chair and the four legs?

I see the purpose as the table, maybe the dinner table that I sit on. It is the biggest thing in the room. For me, my purpose is to help people understand things about themselves that they didn’t know they wanted to know. Why do I phrase it that way? I’ve had many moments where people walked away or years later, personally, I don’t remember meeting you.

It’s okay. A lot of people don’t remember me.

It’s not that you’re unremarkable. It might be because I’m self-involved. It was more about what I was sharing with you, not what you were sharing with me. I’ve had moments with folks like yourself where 2 or 3 years later, I bumped into them and they said, “This moment in this bar you said this and it changed my life.” I didn’t know I did it. I wasn’t trying to do it. It’s this natural flow. It’s been there since I was a kid that I could sit with people and I’d probably be bold enough to say something that could affect them.

When I was trying to understand my why, maybe if people want some guidance in this. I really started developing this when I read the book Start With Why by Simon Sinek. He did a TED Talk on Start With Why. Conceptually it was that your why is different from the how and what you do. The why is there regardless. It is the root system. If the tree does not come out of the root system, it’s not authentic. He uses Apple or Martin Luther King’s message that there is a why there. How that’s distributed, how the phone is distributed or how a great company puts out a product. If they’re doing it well, it’s based on the why first, usually out of some disruption, then the how and the what is a whole other thing.

If my why is that I help people understand things about themselves. They didn’t know they wanted to know. The what could be teaching YouTube sessions. It could be this show that I’m trying to develop. It could be therapy as a therapist. It could be on a podcast. It does not matter if the purpose is the core. The what is going to follow that purpose if you’re doing it right. The how is, “I’m self-regulatory.” You’re learning it right now. I’m talking a lot about myself. I know my story. There’s a way I communicate my story that will help you understand your story. It’s kind of opening you up if I open up first. That was always a part of me but it’s a bit of the how. It’s maybe one component of 20, 30, 40 that I utilize.

You’ve spent seven years trying to launch this docuseries. That’s a passion. The pilot is produced. I watched it when you sent it to me. It gave me goosebumps and inspired me at the same time because of the title alone, Songs That Saved My Life. It does make you stop and think for a second and say, “Maybe I never thought about it that way.” When have I been in a difficult or challenging situation and that song came on the radio on my phone and all of a sudden, my mood completely changed? I watched this pilot that you put together and literally, I was captivated. Talk to me about why you put this together? What was the spark behind it? What’s the idea here?

One day, I was sitting in my office and I got a call from somebody that was connected to Spike Channel, “We’ve got this show we want you to be a part of or at least we’re interested in you. It’s called The Tattooed Therapist.” I’m like, “That’s a bit of a better fit.” I’m sitting there going, “I don’t like reality TV. I don’t want to be a part of it but I need to go down this road.” I talked to some close people and they said, “Go tell them, you have to say yes or no.” I went along the road and it was going pretty well. They were very interested in me. They wanted the film in California, not New York. They wanted somebody with a license in California. They ended up going with a whole another crew of therapists. They were choosing between me and three. They chose three. It was painful because I had seen what could have been.

The show sucked. It was one episode, I ended up seeing the producer on the West Side Highway. I was running one morning. The production company was a New York production company. He was riding his bicycle to work. We hadn’t seen each other since the test shoot. He said, “You dodged a bullet, didn’t you?” I said, “I sure as hell did dodge a bullet.” The whole thing felt phony. Watching that one episode, it was too produced. I knew that would have never worked for me. I would have challenged the things out of them and they would have hated me. They wouldn’t have gotten what they wanted from me.

I came back. I talked to my brother, who works with your wife in the creative arts. They’re creative directors and they’re gifted at what they do. I said to my brother, “This is the time. Let’s create our own thing.” I needed his artistic genius, his ability to create words, form and concept. I told him what I was thinking. Music needs to be a part of it. I want to be the host. I want to interview celebrities. I want to get the story out of them in a way other people can’t because I’m a therapist. I have that unique angle.

Two weeks later, we went for car rides. He goes, “Listen to this song.” He sticks in a Smith song. Do you know anything about the Smiths? Morrissey has a lot of emotion. The song was called the Rubber Ring. It was about a record like the actual disc that was stuck in the corner of an apartment. It was the album that got this person, this human in the apartment through a tough time. The album was saying, “Don’t forget me now that you’re in a good place. Don’t forget the times that I helped you cry and the times I saved your life.” My brother goes, “The show will be called The Songs That Saved Your Life. The logo will be the Sex Pistols logo with the songs that saved your life in it.”

He had this image of Sigmund Freud with a Ramones t-shirt on with his cigar in his hand and a leather jacket on. I knew at that moment that I could give my life to this. For however long it will last if we get it made, I could give the next 10 to 20 years if we were ever lucky to this concept. I remember having a therapy session that day with my therapist. I remember telling him and we both were like, “This is amazing.” We pitched it to our friends and family like, “What do you think?”

Everybody had a song, a song that got them through a hard time. Everybody was like, “Go.” We started filming. We got a couple of people we knew. We filmed in restaurants, beautifully set but it’s me and them. We decided to put a two-minute sizzle reel together and do a Kickstarter to raise some money to film some more. Within ten days, Sony records found out about us. We use the Kickstarter money to get the lawyer to sign the contract. The story continues from there.

You start to build this. What are some of the challenges?

Challenges were instantly, “I’m not famous.” You even see with podcasting who are the podcasters that are killing it. It’s folks who were right on the outskirts of a huge thing. They’re connected to famous people. They have fame themselves like Marc Maron. He is a great example. He is a comedian. He knows all the comedians. He’s flirted with shows, had shows and the possibility of shows on TV and can communicate really well. Joe Rogan is similar. They already have access to talent, following and a gift for entertainment.

I’m a guy who nobody knows, who has a therapy office in New York City. I have made myself pretty obscure almost intentionally. That was the first obstacle, the second obstacle is money. Copyrighting a song is really expensive, which what Sony was going to help with. They weren’t going to give money. They were going to take care of this song rights. They wanted to find funding from outside and a platform. That’s where I think the hardship was. They believed in it completely but to get the other people on board was difficult. It was a difficult time. It was right when Trump was coming into office. Some of the sentimental stuff wasn’t as much a priority in the entertainment world, some more social activism, “Let’s fight the powers that be.” Those kinds of shows were probably going to be more prioritized.

You try to push through that by finding DMC.

We had a meeting with Sony, People Magazine and Entertainment Weekly. We were at a Time Inc. office in Battery Park. We had this meeting with the Execs there. It was basically, “Let’s meet Drew. We’ve seen the sizzle reel. Let’s meet Drew to see if this is a good fit.” That’s kind of how Sony pitched it to me before we went in, “Be yourself.” It was interesting because the woman was captivated by the show, one of the people in our sizzle reel was this guy named Norbert Leo Butz, who’s a two-time Tony Award winner for Best Actor. His song was a Bruce Springsteen song. There was a little clip in there.

At that time, I wasn’t into Bruce when I did this interview with Norbert. I didn’t know much about him. This was years ago. The woman at People Magazine loves Norbert. He was her favorite Broadway actor. There was already this connection. She wanted to talk about Norbert. Norbert is a great guy and I still appreciate him. He’s thoughtful. They wanted to be a part of it. In the meeting, they said, “Who do you want as guests?” I was reading People Magazine. There was a little profile of DMC. His name is Darryl McDaniels. He is the DMC in Run DMC. They are the godfathers of hip-hop. Everybody bows to DMC when DMC is considered by many as one of the top MCs of all time.

They run originals.

He is one of the Ogs. They changed everything. They were the first to go gold, platinum, and go multi-platinum. They were the first on MTV. Before them, there weren’t a lot of non-athletes with athletic brand connections. Run DMC, they had that song by Adidas and they built a relationship with Adidas that they still have that connection to an athletic brand. They were one of the first non-athletes to have that kind of connection to an athletic brand. The first album that my brother ever got was the first Run DMC album. I was 5, he was 14 or 13. Our parents got it for him. There was this deep connection. The whole concept of the show is about me and my brother’s relationship together with music.

My brother mentions DMC. He’s like, “He wrote this book. It’s called Ten Ways Not to Commit Suicide. In the first chapter and last chapter, he talks about the song that saved his life.” People Magazine had put out this article on it. My brother’s like, “He would be perfect. We don’t know anybody who actually has a song. We know he has a song.” They were like, “We could probably do that.” If we ended up working together. They weren’t to give Sony enough money to work with. It didn’t go anywhere. Two years later, we are about to end our relationship with Sony because it wasn’t going anywhere. We were feeling a bit tied. The contract was ending. It was no fault of theirs. It was that there were a lot of things working against Sony and us.

I went to the gym. I hadn’t been to the gym in a month because I had an injury. My gym on Seventh Avenue was closed, so I had to go to Varick right by the Holland Tunnel. I walk there from the West Village. It was a new route. I had never gone there before. I went in the afternoon, which I never did. I was going in the morning. I’m coming back. It’s a summer day. I’m sweaty. I’m done with my workout. I’m walking down Hudson Street, which I never would have walked down if my other gym was open. Who do I walk past two blocks from my apartment? The fucking DMC. He’s trying to put money into the parking meter and he can’t figure it out. I walked past him. I noticed everything. I have that visual mind. I see celebrities all the time. I’m like, “That’s so and so.”

I’m sitting there on the corner going, “I have DMC in front of me. I have friends who have given me thousands of dollars to make this show work. People who have believed in me. A family who have supported me.” Three to four years at that time of therapy, I was doing it to survive wanting to keep going with this show despite all these obstacles. I was thinking of keeping on walking because of ego. I didn’t want to have to walk up to a celebrity because in my mind, even talking to you, I am the most famous person that is a non-famous person that you’ve ever met. That’s how my mind works. You need a little bit of that ego to want to be on camera.

I sat there and I got over myself, “Are you fucking kidding me right now? You have this opportunity. Who cares what he says you have to put this into the universe even to get the door shut in your face to know that door needs to be shut and you don’t need to dream about it?” I walked over. At the time I was still with Sony. I said, “D, we are both signed with Sony. I have a show I’m working on called The Songs that Save Your Life. I would love to hear the story that I know that you have.” He’s like, “Me and so and so?” I don’t want to name who the song is. We should keep that. It’s a good payoff. If ever this show ever gets aired, it’s a good payoff. It’s like, “The story of me and so and so?” I said, “Yeah.” After a short conversation, he gives me his phone number and gives me his email address. I texted him that day and he responded.

Did it work? Is it a real phone number?

That’s what I was trying to test. Is it a real number? He wrote back and said, “It’s great to meet you.” I remember when I left him in person. I was walking away. He goes, “One second.” I turned around and he goes, “Therapy is a gangster.” He walked away. I text him and I end the text with a Therapy Is Gangster. He writes me back. I wrote to him every week for three months with no response. After that, nothing. I give up. I thought this was our time. This was the thing. God had spoken by putting him in my way. It’s the hero’s journey where supernatural aid comes to my benefit. A hero comes to my aid. We get to go on the journey together and we go to Mordor. I was broken by that. I said, “It’s not the right time.”

Six to seven months later, my brother who was working with your wife at the time was called for M&M’s or Mars, one of those companies to go to Austin for South by Southwest to run their stage, their advertising and marketing at that event. He had full access to a lot of things and to the bands. DMC was speaking down there, he’s doing a podcast. In that podcast, he’s talking about the song that saved his life and all that stuff. My brother goes up to him afterwards and says, “My brother got in touch with you nearly a year ago.” He mentioned what we were doing. He’s like, “Yes. I remember I want to do that. Here’s my information.” My brother goes, “No. Where’s your manager? We’ve already done this once and it did not work. We need to talk to your manager.” He connected to the manager, they became close and went to a couple of shows together. Chris went to some DMC events down there.

They came back and came to one of my restaurants. The four of us sat down. Me and my brother who’s the cofounder of the show or co-developer. We talked for two hours. In the end, DMC says, “This thing is going to look global. I’ll give you access to every part of my life. I want to help you make this happen.” We filmed, we left Sony and that ended. We went on our own. We filmed it ourselves. I paid for it. We started pitching it and Coronavirus happened. We were silent for nine months and now I’m pitching it again. There’s been a lot of rejection.

You talked about that rejection when we spoke. I found it intriguing because you said that although the support for this show has been challenging from the start but specifically over the last couple of months because you now have the pilot. There’s something tangible now people can watch it and get it. You haven’t quit because you said that although no one has come and said, “Here it is. Let’s go.” No one has told you to stop.

The word that keeps on coming up is obedience. There’s something deep in my core that says this is going to happen but it’s not if, it’s when. I’ve wrestled with that for years. A lot of times, it’s been if. There’ve been many great artists, great humans that have come alongside us and said, “We will help you with this. We want to do whatever we can to make it work,” that me and my brother believe in because of their resume and their character including DMC in there. His character is so on point. His drive is inspiring. A Producer/Director that we have involved now named David, who has come alongside and has worked in this world his whole life believes that this is his calling at some level. This show is part of his four legs.

We’ve had all those kinds of characters come along. Every time there was this moment in which giving up felt right, some supernatural thing happened. I had a call from a friend in Brazil once that shared a quote with me that was the quote I was thinking about that morning. He’s like, “I think something’s going to happen.” It was those moments where it’s weird. I think Carl Young would have called them serendipities. Those moments where you go, “There’s something bigger happening in the world, in the universe that I am not totally understanding but it’s telling me to keep going on this hero’s journey.” With all the challenges and temptations, there are all these revelations happening. That’s kept me from getting off course.

I was in Mexico with a ton of powerhouse leaders and all of them even were saying, “It’s going to happen. We’re going to help.” Even there, I came back with these contacts in Hollywood but still, it hasn’t landed. It’s about financing and connections. I’ll know the right people when they reveal themselves but if they don’t ever reveal themselves, something else will have to be the thing that I go towards but I can’t imagine it not being this. It feels so right.

You keep driving every day. That’s what it comes down to. You’ve got to go until somebody does stand up and says, “No it’s not going to happen. Here are the concrete reasons why it’s not going to happen,” and even at that point, you probably still go for a little while.

We’ve already gotten that for a number of people. We’re going to make sure they don’t matter in our heads at least because everybody has a fucking opinion. It’s about, “Is there enough of a team in a community that resists that voice that is saying, ‘I get why they’re saying this but no, we still believe in it,’” and there is. The numbers are growing. It’s probably that one human out there who works in this world, who has the money and the platform that says, “Let’s go.”

I feel like everybody has their moment. They have something that they can relate to. In content generation that’s what people are looking for. They’re looking for that thing that they can relate to and say, “I know when I felt like that.”

Music is universal. It is healing. We go to it before we usually go to anything else.

People always say, “What kind of music do you like?” I laugh because I think I come across as some lunatic because I’m like, “I don’t know. I like all music.” It depends on my mood. I go back and forth in these wild swings. It can be a hard rock to classical to modern electronic dance music and then it’s country. It goes from one to the other. People say, “That’s not one kind of type.” “I like it all. It all depends on how I feel right now.”

I was thinking about what’s my song and I was like, “I didn’t know where to go,” because of what I said. There are many times where it’s like, “How do I feel?” I had to think about those times in my life where it’s been at the bottom. I’ve had many of them where I’ve sat there and said, “Everything in my life is going to change.” I don’t know what’s next and that’s scary. I talk a lot about fear, the fear of the unknown. As a leader, you have to be confident that you can understand that you’re in a position right now where there’s an unknown ahead of you and not be intimidated and fearful but internalize it and say, “Because I know that there’s uncertainty ahead of me, I’m in a better position than if I sit here and become overtaken by these emotions.”

I can then generate a plan. I can think about what I need to do and I can start to prioritize things. We’ll go with the Enneagram now and that comes back to what my core is, to solve problems. I was thinking about what’s my song? I thought about where you are when you’re always in these moments where you’re thinking about your life. I always find myself in the car. When you’re in the car by yourself, you know you should catch up with people and call people on the phone but you don’t want to so you listen to music or listen to a podcast.

That’s also the point where when you’ve been there a few times, there is always this song that may come on always resonates with you. This happened to me several times. It’s this song by a guy named John Parr. It’s called Man In Motion. It’s from the movie St. Elmo’s Fire. It’s a bit older but it resonates with me so much because it’s about seizing the opportunity. Understanding that right now, things are bad. If you seize the opportunity and you see it, you will get out of it. I took a couple of notes that I wanted to share with you. I even took the timestamps. It’s like 43 seconds into this, he says, “Play the game. You know you can’t quit until it’s won. Soldier on, only you can do what must be done.”

That’s the drive and resiliency that I believe is one of my core strengths where you can’t quit. It’s telling me, “Don’t quit.” Because I was in the Special Forces, there’s this element of being a soldier. “You have to stand up, you have to figure it out and you don’t get to walk away.” Then there’s this individuality of, “No one’s going to do this for you.” You’re in this situation, you put yourself in this situation. You need to own that because nobody’s coming in here to fix it for you. It’s going to be you. That leads into this refrain of, “I can see a new horizon underneath the blazing sky. I’ll be with the eagles flying higher and higher, take me where the future is lying.”

That’s that optimism of, “If I own my past, I understand it. I don’t quit. I can look ahead. I can get it back.” It resonates that you’re flying high again. It’s like, “Now there’s all this emotion of optimism and perseverance. It’s not going to be like this forever.” At 1 minute 53 seconds, it comes to, “I can make it. I know I can. You broke the boy in me but you won’t break the man.” It goes straight back into the refrain. That is maturity. I see that as maturity in my life from when I was younger and I was like you. I wanted to fight everybody in the room. It didn’t matter who they were. If they looked at me wrong, if they bumped my shoulder, that escalated and usually commensurate with the amount of beers that I had and judge how long that fuse was.

I’m relating.

I think about the maturity that you have as a young person as you get older where you’re able to internalize things much better and much faster with much more clarity and calmness. There’s the opportunity to say, earlier in my life, I would have become overcome by what’s happening to me right now. I can now stop, understand it and chart the path forward. This is a song that I always go to when I’ve been in those situations and like you, I have been there with tears in my eyes saying, “You’re going to get through this but you’ve got to do it. You’ve got to own it.”

Do you allow yourself in those moments to feel the pain or is it really about getting out of it?

It’s about getting out of it. I’m a problem solver. I try to understand what got me here but also understand that there’s nothing you can do. I try not to dwell on that. It’s that short memory they talked about with athletes all the time. You’ve got to get up, forget about it, move on and learn from it. I try not to think about those things in a way that will become paralyzing to the next step. That doesn’t mean that there are not times where I sit there and put my head in my hands and say, “All is lost. There is no hope.” You have that but those times get shorter when you can sit there and say, “I’ve got to figure out how to get out of this.”

I’m tempted to be a therapist right now. I’m not going to do that.

Let’s talk about therapists. Let’s talk about the Enneagram, the theory behind it and this perspective that personality is by nature interconnected and multi-dimensional. This Enneagram Theory is used in mental health, team building and leadership development. It’s centered around these nine core personality types that have these wings that are bringing associated personality types to them. There are these different directions that your personality goes. You exhibit these ten different tendencies under stress and under security being two different ends of the spectrum. Safety, security, stress and the unknown.

If you would for a little bit talk about the Enneagram Theory, why did you choose it as your practice, and how you grounded it. For all the readers, there’s kind of a complex matrix around here that I think we will try to explain as best as we can. When we make the cover art, we’re going to have the Enneagram model on there.

It suggests that our desires and our defensiveness to the world are interconnected. We protect ourselves by using one of these and it is also our Achilles’ heel in a sense. Mine for example is envy. I’ll give you a quick example. If I walk out of my apartment in the West Village, I have to the left of me, the building directly next to my building is Julian Morris’ house. It is a full townhouse, maybe four floors. If I walk to the right there is Julian Schnabel’s building. He’s one of the great contemporary artists of our time. Past his place is Calvin Klein’s and Hugh Jackman’s house. Hugh’s is the one that I center on.

If I go over to the West Side Highway, go to Charles Street, I look back it is three floors, a full floor, all glass you can see in their spiral steps. There’s a Peloton up there, a track and the whole thing. My envy starts flaring. We suffer from all of our passions. All of the sins, in a sense. You can change those words or passions or sins. I struggle with fear at times, deceit, pride, anger, gluttony and lust but envy is the one that hits me the most. It is my dark passenger. I’m sitting on Charles Street Pier and the thoughts that come up are, “Why does Hugh have this?” “Screw Hugh.” “I should have that place where I could put great couches in that place and I can have great parties at that place.” “I can build community and fellowship. I could have you over. I could have some of the folks reading. I could restore the house, great bourbon and all of those things that are that envy getting in my system.”

That goes pretty quickly because I’ve worked through it but it’s still there. It’s there all throughout the day you mentioned me being 6’4”. If I walk past the guy who’s 6’4”, I instantly want to be 6’2”. I don’t want to really be 6’4”. That’s too much but I still want to be taller. If his smile is such or this lady is a nice-looking lady, there’s an instant like, “I’m better than that guy,” because my way of dealing with envy is to get competitive. This is where I will get into the subtypes. Envy also drives me. If I see all these things that are awesome out in the world that I want, I strive for them.

I’m a four, which is the individualist or the romantic. We tend to be the most emotional most prone to suicide, art, and communication that it fuels a lot of my desire to take in, to become this great original authentic self that will wow and impress. What am I charged by? Being impressed by other things and other people. I also want to impress. It’s this double-edged sword. That’s the beauty of the Enneagram. It shows you your wheats and your weeds. It suggests you can only pull out so many weeds. They’re going to keep on coming up even if you keep on pulling them out. You have to have a good ability to garden this plot. Get the weeds out as quickly as possible, even though they’re going to keep on coming up. In my case, envy is going to be with me all day but I need not hate it. Each of us has this primary one. When we throw subtypes on it, it gets even more complicated but you’re born with this.

What I think is we have a predisposition and there are three centers of intelligence. Heart, head and gut. I’m in the heart camp. Two, three and four are heart camps. If you were an eight, you’d be in the gut camp. That is how we move in the world. We make decisions from these places. I was probably born a heart person. The nature of my environment subjected me to one of those actual 2, 3 or 4. In my case, the four is about individuality, uniqueness and authenticity. We want to find our worth through you thinking that we are special. The three want to find their worth through ambition and what they do. It’s about, “Did I achieve a certain thing that you could be impressed by?” The two is bent on, “Have I cared for people well?” They’re a caregiver.

Have I helped well? If I grew up in a house in which I had a parent who is needy, perhaps an alcoholic or somebody who had physical ailments or I was born the first child not the third child, I might have gone into a caregiver mentality. If my parents were a bit more intense or demanding on grades and performance, I might have been three but I was the youngest of three. I also got a lot of attention because I was the youngest. I wasn’t young like, “I’m the third in line. I was a surprise.” I’m seven years younger than my middle brother and eight years younger than my older brother. There’s not as much competition and there was a lot of attention because I’m a baby. There’s a gap there, so the competition for them wasn’t as high. My parents had chilled out quite a bit because they had parented for a while. There wasn’t as much demand on me. That’s where I’d put it. I also think people could be on that border of the gut. I like to say gut or heart or gut and head. You could swing either way. It’s a nurture or nature thing. This is where it’s not scientific, it’s hard to figure that out.

Is any one of these better than another?


There’s no differentiation between males or females?

Maybe some of the ways that would be manifested. We live in a culture in which women are having more ability, more possibilities to be an achiever but that might have had to be repressed early on in the ‘50s or whenever back in the day. It might have been more confusing for them to get at some of that and that’s an example. There are certain cultures in which it’s not as acceptable to be a certain number.

If you run down the list of the nine and you have this circle. If you think about nine points, equal distance apart on the circumference of the circle, nine at the top going from right to left. Starting with one, you have perfectionist, helper, achiever, individualist, investigator, loyalist, enthusiast, challenger and peacemaker. How do you characterize somebody? What’s that process?

It’s three-fold. I would give them a test. This is pseudo-science. There’s a bit of mysticism in this. It’s not to me like a horoscope. For example, I read my favorite fiction book, which is East of Eden by John Steinbeck. The character descriptions and this is written probably in the ‘30s, ‘40s, maybe ‘50s before the Enneagram was developed or known as a typology. You’d see that those characters fit the numbers. Throughout time and history, people fit into these categories. They’re pretty accurate. I would be looking for, personally, in relationship with people, some of the common themes then I’d go to, “Do they tend to be gut heart or head people?” Do they get stuck in their head, their emotions, and some of their hostility? Gut people tend to be hostile. The nines don’t know it that well. Sevens don’t either. Eights are pretty comfortable with their hostility at some level.

I know exactly when I’m hostile.

I’d be looking at the subtypes. The subtypes are interesting because the subtypes have been talked about well before the Enneagram was developed. It was incorporated in. It’s sexual, social, and self-preserving. If you’re a sexual type, it doesn’t mean you like to hump and get down but you probably don’t mind that. It’s that you are intense and looking for exalted moments. You’re primarily interested in one-on-one relationships or small groups. This might be with certain authors. I like John Steinbeck. I will devour John Steinbeck. I deeply pair with him in my mind. You were talking about music. I got into all kinds of music. I’m specific. I pair with certain things because I’m a sexual type.

We are stacked, we’re all three but sexual types are more intense. They pair. If they go into a party, they’re thinking about, “Who do I want to talk to? Who’s going to be interesting to spend the night with here at this party and drown out a lot of the noise so I could get deep with them?” The self-preservers are going to go into a party worried about where the food is, what is the best room to be in and “Do I have the right resources to be here? Am I energized enough to deal with all these humans?” They’re least concerned about human interaction. They are worried about maybe Maslow’s lower needs, shelter, food, how their body is being preserved, how their mind and heart are being preserved to go and handle the world with.

The social types are going to walk into that party and think how to fit into the herd, “Who’s the most powerful here? Who’s the least powerful? Will I be accepted by the group?” You might notice when you’re talking to a social type at a party, they might be looking around quite a bit like, “What’s going on?” “Who is Jim talking to?” “Who is Suzy talking to?” “Are they having a better conversation than I am?” The sexual type they’ve chosen. They might move on because they’re bored but they’re not looking at everybody. They’ve said, “There are a couple of people here that are striking my fancy. Who is going to walk through life with the group or me?” These are all instincts we have built early on in life to protect us. In a sense, we don’t have pterodactyl chasing us anymore or T-Rexes trying to eat us.

A lot of our needs have been met but the emotional needs of, how do I stay safe with humans is a priority. If you came from an abusive childhood or a great childhood you would have developed a certain instinct to handle life. A lot of people think these were more nurture based. They’re more, “I’m presented with an environment. How do I deal with it? How do I survive this situation and feel safe and secure?” I’d be looking for those things. I know it’s a lot. I’d been looking for those things. The test will give you that. I’m going to ask them what they are gravitating towards because people spend years trying to figure it out.

For me, all I had to do was when I first heard about the Enneagram and I decided to look at it. I looked down on the paper and went, “That one is essentially the description of my notes as a client.” I take notes for every therapy session that I am a client in with my therapist. I have a book with notes from all of my therapy sessions. If I went back and looked at all of those things that I have struggled with and I continue to struggle with, they all fit into that category of the individualist. It was blatantly obvious to me and it was about learning a bit more.

That was how I felt about the challenger when I read the description of eight. That was how I felt, especially when you start adding in something.

What struck you the most?

It’s defined by self-confidence, decisive, willful, confrontational when I started adding in some of the other pieces for instance, where you talked about the centers. You define the centers as 8, 9 and 1 being gut. 2, 3, 4 being heart, 5, 6, 7 being head. You can also classify those as 8, 9 and 1 being gut but that’s your instinctive center that is manifested in anger and rage. Also, 2, 3, 4 are the heart. That’s the feeling center but it manifests in shame and 5, 6 and 7 are the head. That’s the thinking center and it’s manifested in fear. Although I experience all of these things. That’s one of the cool things about the enneagram. You exhibit all nine of these personality traits in some way. It manifests in some way of your personality at all times but your core to one.

I look at myself and say, “Of these descriptions of each one of the nine, I most identify with this level of self-confidence, decisiveness, willfulness and confrontational while at the same time, I do manifest my frustrations. I manifest things in anger and rage.” I’m not an overly technical person that looks at an engineering floor says, “I understand how all this works.” Not only have I been told but I know that at times I do not have the level of empathy that I probably should from that heart perspective periods of time where I don’t identify as well with that. As I broke that down that’s where I went towards. I went to these wings and said, “I’ll let you describe the wing theory,” but that resonated with each side of the challenger. Why don’t you talk about the wings?

The wings are whatever the two numbers are to the side of you. If you’re an eight, your wing is going to be a 7 or a 9. This means that you’re more developed towards those numbers. You lean a certain way. In my own life, I’m a 4 wing 3 but 3 is actually the next highest number I score on the test. That’s the ambitious type. I am an entrepreneurial four in a sense. I am a driven four. I lean that way. I don’t lean head. While I can get stuck in my head, I don’t perseverate too much on fear. I am not structured in that way. That’s the part of me that I have to develop like any wings of any bird. If one is operating too strongly, you’re going to go in a circle.

The idea with the Enneagram is that as you develop both sides of yourself, you realize the parts that are weak or deficient and you start trying to develop those. For me, that would look like trying to tap into that head part of myself. It’s underdeveloped. With the wings, a test would give you that read up but you have to look, be honest with yourself and go, “Which side do I lean on?” It doesn’t mean it’s your next highest number, it means that you tend to gravitate towards that as being more comfortable to be more comfortable to utilize those skillsets. Does that make sense?

It does. That’s why I think I lean more towards that head area, the seven in the enthusiast where it’s spontaneous, versatile, acquisitive, somewhat scattered or what can come across as scattered for sure when you try to get involved in a lot of different things, versus the peacemaker which is defined as receptive, reassuring, complacent and resigned. I wouldn’t necessarily classify myself there.

There are categories of numbers too. The 7s and 8s are assertive types. This is why I asked you. I said I wanted to put on my therapist hat when you were talking about your song. It was much about assertiveness. This song was beautiful, “Get your shit together. Let’s go.”

That’s coming across at times as abrasive, I’ve been told.

Not only abrasive, but it also has to have a cost. The cost is your emotions. It will be harder to relate to you emotionally if everything is about the mission. How can I be with this person? How can I talk about my emotions not get a reaction back, which is like, “Here’s what you can do about it? Let’s go. Let’s do this. These are the steps.” If you did that to a four, you could do that maybe to a sexual four, which is what I am. You will miss them because they want to be known and understood. That will actually help them be driven. If you tell them what to do in a very practical way and don’t acknowledge their emotions, you will essentially trample on them. You’ll get a less active and productive person.

This is why I love Enneagram. It’s magic in marriages because for twenty-some-odd years, these people have been trying to change each other. They didn’t realize that it isn’t changing. This is the number they are and this is the subtype they are. If the subtypes aren’t understood by this couple, they can destroy each other because they’re trying to get each other to live this the way they do best. I know with you, if I was in a car with you, we were listening to music and your tears came up, you’d probably push them away quick enough to try to push on to some focus that is in the distance, which requires you to get ready and get engaged to produce.

We immediately start talking about where we’re going and what we’re going to do.

To me, the assertive types are always going to underdo emotion. They’re going to be blinded to their opportunity. For me to know what the legs of my chair require a lot of pain, a lot of me sitting in the pain and a lot of me knows what not to do. I’m not suggesting that 3, 7 and 8, which are the assertive types aren’t passionate about what they do or aren’t purposeful about what they do, but many, when they’re not aware of their emotions are doers. Getting shit done but it isn’t as purposeful or definitive to who they are as it could be. Carl Jung would say, “Don’t compare. Don’t contrast. Everybody else’s path is a temptation to you.”

The 3, 7 and 8 can be tempted by a lot of paths because they’re moving so much that they don’t actually focus on what their true path is. That’s not an accusation. They have to find ways to slow down. A lot of times. It is meditation but even the right type of meditation can investigate their soul a bit because it’s that old adage which, most of life’s problems are because a man can’t sit in a room by himself. The 7 and 8 have a real tough time sitting in a room by themselves. That’s not that’s not productive.

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I get nothing done if I’m by myself.

Where I wanted to go with you on that song is if you were in my office, to help you balance yourself out, to help you develop the parts that are underdeveloped, especially the heart. I’m not saying you don’t care or you don’t have empathy but it’s not going to be a primary tool of yours is to stop and feel, slow down, sit and be like, “Let me just feel what I’m feeling right now.” I would have them work with you on that. The goal would be to make your production more effective in the long run. You’d be more tapped into what makes you what you should gravitate towards but you might cry also because I’ll try to get you there.

I have this self-talk about something else.

I know that was coming because I know you were an 8.

We mentioned that if you have this core personality trait. You exhibit a complementary or sometimes opposite characteristic whether you are under stress or whether you are in times of safety. Do you want to talk about that?

It’s beautiful. I’ll keep on using myself because I’m a four and I’m self-referential. We’re very subjective. If you are visualizing this in the audience, there’s a circle. There’s a triangle within the circle and there’s a hexagon within the circle. There’s the seven-part thing within the circle, a three-part triangle and then your circle. The circle is about unity, the triangle is about the Law of Three. Is hex seven?

Hex is six.

Let’s go with whatever seven is. It’s within this circle so there are seven parts hitting the circle. It’s much too complex to talk about here but your number will make a triangle. It’s not a perfect triangle. The 936 is a perfect triangle but my four gravitates towards a 1 and a 2. It makes a weird and fine triangle there. When I am under stress, I will look at a two as the version of a four. Meaning, they are the caregivers. They care about helping people and if they are not healthy, they’re going to help people who are likely not to get helped and they might spend their life on it. This is where you see an alcoholic with a caregiver. We look at them and go, “The saint in the sinner. She cares so much about him and spends her life trying to help them out. He’s so bad.”

I go, “No. They’re equally dysfunctional. This person’s finding all their worth and helping the person who can’t get help so they get to stay in a state of not progressing because they’re fearful of progressing because that would require much more of them in life.” When the four is insecure, rejected, hurting, and afraid, I’ll look like a two a little bit. I’m going to probably gravitate towards getting help or giving help to find worth. I might want to help somebody and be a caregiver or I might want to go and get nurtured. If I am feeling secure, safe, healthy, I look at one as a version of a four. Fours are subjective. Ones are the reformer. They’re perfectionists and moral. They don’t want to be corrupted. They have a lot of balance.

The four are emotional, subjective and can often be erratic with their emotions. They’re very sensitive. When we are in a good place, we’ll look a little bit more balanced, less giving a shit about what people think about us. We will give more form and order to things. Let me give you the countries. They say the four is France, for regions. We dress, we look cool, we have artistic ability, style, pompous, elitist and we think that our art is the best art. The reformer probably looks much more German. The one, “How do I get things done properly with order and efficiency? How can I be moral?”

We could look back at history and have our issues with the Germans but even there in their dark history, there was this, “This is the way it should be done. It must be pure.” It’s an extreme version, an unhealthy version of a country that’s one mentality. What essentially, you’re doing is taking this flamboyant elitist artist and going, “Let’s have some form and some order and not be so worried about what other people think.” “Cool, you might be productive, you might be a great artist that changes the world.” That is how each number has these counter numbers that they can look to go, “That’s the part of me that is underexercised, underdeveloped and I have to develop it.”

For example, I have a lot of friends who are nines, they’re seen as sloths. It’s not necessarily that they’re lazy and they’re slow. They are a bit slow but they’re slow to their passions, desires, their feelings, but they’re a peacemaker so they want to keep peace in the world. It’s a safe place to land but they often are not productive. They can’t get work done. They could be on a team and do their part. They can work for a company and they work hard, but they can’t, in their own life, put that productivity and make the achievements big or the entrepreneur that they’d love to be, maybe. They have to look to the three who are the ambitious type. It’s this natural connection and you can use that the rest of your life to go, “Am I accessing that right now?” It’s the candy coating outside of you are all chocolate but the M&M is for me. I’m chocolate but I have a coating of one when I’m in a good place and a coating of a two when I’m in a bad place.

I saw that even with mine where I know that in times of stress, I go to the five as an investigator where I need to solve the problem. In times of security, I become the helper where I’m more attuned to what other people may need and more inclined to be a resource to them versus in stress where it’s like, “I’ve got to get this done.” What’s the goal of the Enneagram? I look at it and I say, “Your personality is this combination. This equation, if you will, of the core plus the wing plus how do you feel insecurity, stress, and that becomes you.”

Here are your sins, strengths, wheat, and your weeds. They’re going to live together, get over it. Don’t think that on your deathbed, you are going to be completely well. If you know that, you can be patient with yourself and you can chip away. When these moments happen on the West Side Highway and I’m sitting on Christopher Street Pier and I’m looking at Hughes place and the dark passenger starts screaming from his apartment, I’d slow down and go, “Of course, you’re doing that.” Envy is always your passenger. Get over it. Let’s move on. Hughes was awesome. I’m sure. I hope he enjoys his place. “How about your place?” “It’s pretty awesome too. Enjoy it and move on.” Until I walk five steps and I see the guy who’s taller than me and I’m like, “I want to be another inch taller.” The envy starts again and for me and it’s cutting down on the hauntedness of that experience.

You’re on a path now to bring music into the Enneagram. What’s going on with that project? Because I saw all these sticky notes on your board in front of you. When I asked you, you’re like, “That’s my project to bring music to Enneagram.”

I’ve been working on this project for a couple of years and because I am a four, there’s no doubt that this is a huge component of it. I have kept myself hidden on the macro level from the world. I’ve not done podcasts, any teaching that has been for the masses, done any interviews, or not put myself out there. Because in my mind, I will reveal myself with this show. I will arise. You will not have known about me. Who is this person? Now he’s here. I didn’t want to do any of the things that would put myself out there until the time I thought was appropriate and it was when the show happened?

The show may never happen and I’ve got gifts to give the world. While I was in Mexico, I was around a number of people who are high performers and they were out there doing macro-level things on whatever level. None of them, in my mind, were any more powerful than me and had any stronger message than me. A lot of them had books, apps and had a thing. Even on your show, I might be one of the only people who doesn’t have this long resume of public attributes. I am now at a point where I don’t give a fuck because I know I’m going to pull people in with my personality, whether you like it or you don’t. I’d reckon with that and I had to say to myself, “It is now time to be out there.” How can I be out there in the way that I like?

I don’t want to do a podcast because I won’t be seen. Facial expressions, body movement, mannerisms, and the aesthetics of the environment are important. I care about them. What’s the lesser level than my show? It’s YouTube. I’m working on a series now only on the Enneagram four. It’s called 4×4. Four things every enneagram four needs to know given by a four. We’re doing the subtypes first. That’s social, sexual, and self-preserving. We are all three and we are stacked of importance and the one that’s least important to you. When you go into that party, you’re all three. You have a dominant and a repressed. I care least about the purge because it’s my least prioritized but even those, we have to integrate because the enneagram is about wholeness. It’s about integration.

The first three episodes are an introduction to the subtypes and each subtype. I’m using the music and the lyrics of Steven Patrick Morrissey, from The Smiths, who I think is a four. Each four of the categories is a song that represents that subtype in a different way. I will be moving on towards a five-part series. The last part is Rest and it is all about work. How do fours get the most work out of themselves? I know where this is going to go which is going to go to probably other numbers and other things that I want to do.

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I want to do an episode on Jerry Seinfeld and on my five mentors that are not by my side. My mentors in abstention are my vicarious mentorship. John Steinbeck, the writer, I’d like to diversify my group of artists. I’ve got the writer, the comedian, the poet, the psychologist, and the singer. It’s Bruce, Carl Jung, and Ray Ana Marie Rocha. Admission, I don’t like poetry. I don’t read his poetry. I like all the other stuff he wrote and Seinfeld and Steinbeck. When I do any of these YouTubes, I try not to take quotes from all over the place, “Here’s a Churchill quote and a Lincoln quote.” I’d rather be singular and centered, so I use those five, particularly throughout all of my episodes. I have not posted them yet, but ultimately, they will be posted on Drew Newkirk YouTube.

You have these investments in the restaurant industry. As I understand it, you took your more common investments in the market and stuff and you viewed those as transparent or they were invisible. You decided to take that out and put it into something that was more tangible and more visible, although quite risky. What was that thought process? What is it that intrigues you so much that you would take this risk?

Some of it was ignorance, arrogance and vanity.

That was humility.

This was years ago, where I know that my experience with New York City is much centered around restaurants and bars. When I first moved to the city, a lot of the friends that I already had were bartenders or bar owners. I learned a lot about the business by sitting there and observing. In the lower part of Manhattan, there are a few people who do what you’d call a small bar-restaurant that usually has more than five places. I know them all, for the most part, at least the ones that I respect. I’ve gotten to know them and one I’ve gotten close with over the years. His first few ventures were successful. His third venture was going to be in my neighborhood and the fourth venture was going to be a nautical-themed bar and I’m a beach guy also. He gave me the opportunity to jump in on these and they only take money from close friends and family.

I saw him as disruptive to the game when he first came out. They do cocktails, the high level, at full capacity. The bar was packed five deep and they are pumping out all fresh ingredients and they’re known for it. If you ask people in the industry about them, their team, they’d know it. I only try to only attach myself to people I have found to be disruptive in their industry and also well-respected. To me, a bar is a place that I can go to get away from communicating all day but still communicate. I could talk to the bartender and all the people who work there but they’re busy.

No one’s going to take all my time. I could jump in and out of the conversation but additionally, when I have people in town, friends, and family, I can bring them to this place and treat them well. New York’s tough. Not everybody has the apartment to do that in. I’m lucky to have a big apartment but I like the idea of going out, so this is a place I can host at. Additionally, I wanted to learn the industry more and it is a part of my business psychology that I don’t get to exercise some of that more corporate work. The more team building, the more like, “Who’s the right fit, who’s not the fit.” Basically, as a silent investor, I’ll get asked about things that are high level to say, “How’d you experience this?” I’m pretty definitive on what I experienced. Sometimes that is helpful to the team but ultimately, it’s in support of them to have what their mission is and how they visualize how to treat people when they walk in that door and how that person will feel instantly. How do you set up an environment to make a person feel a certain way?

As a therapist, it’s hugely important to me. I have clients who have picked me based on my website, visually. I said, “I knew when I walked into your office that I would feel a certain way,” and they were right. I don’t have pictures of my office on my website, at least my New York City website. I know people instantly feel safe here. I look for that instant thing. Those singular ideas where people are certain to have a vision. Adaptable but certain. They have a plan A and they’re usually not going to go to plan B because they’re going to see Plan A through even if it’s tweaked. It’s been a joy.

Coronavirus did not help. We lost one restaurant. I lost a big investment there. We also opened up a restaurant during that time. It was supposed to be the second part. We have Wild Son which is on the West Side and we were opening up Wild Son on the East Side. The cool part about it is it’s wildly successful already, even during Coronavirus. We’re not out of this pandemic yet but we had to close the other one down. It was more tourist-centered and we had an idea that this is not going to be a thing we should keep long-term. Let’s cut the losses and move on. I appreciated their wisdom in making that decision but I have to grieve the financial loss. Also, this new thing is being birthed and we’ve talked about my other financial on investments personally. I had to grieve the fact that the investments I took to invest in the restaurants have been successful since.

I do have to ask before we close out and I bring it up every time that the Jedburghs need three things to be successful in their operation in World War II. They had to be able to shoot, move and communicate. If they had to be able to communicate, if they could do those three things well, every single day, then any challenge that came their way they could conquer. What are the three things every day when you wake up, you say, “If I can do these three things well now, I will be better at the end of the day when I go to bed than I was when I woke up?”

I’m going to cheat. I’m going to steal Jed’s work. I did a little research on the Jeds. The name comes from the Scottish border people who are the Border Reivers. They sound badasses. They trained on the Scottish Highlands before they went into battle. I am a communicator. It is my life. From out of the womb, I was a communicator. It’s what I do well, so I appreciate that was part of what was their core and it is part of my core. It’s the top three. The shooting, I love the metaphor here because in many parts of my life, I was a machine gun and not a sniper. A sniper gets rid of the bullshit and the noise. They are narrow, singular, centered and they are no longer comparing and contrasting themselves to all the other folks out there that are maybe doing it better.

As I’ve grown, I’ve become more of a sniper. I know what I can shoot well, what my range is, and what are good targets. In the movement sense, that I know what to move towards and move away from. Also, that I move, not disregarding or abdicating my responsibility to my emotion but that action is important. In New Mexico, Richard Rohr, who’s a guy that I am impressed by as far as his work and he’s the one who introduced me to the Enneagram. Not personally, but in his work.

He has this center called the Center for Contemplation and Action. He says that the most important word in that phrase is and. That when contemplation and action are unified and working together, that’s when we get the best results that contemplate then plunge so the movement into what is mine to do, what is mine to shoot, that being, communication, communicating well, and communicating on those four levels. I’m bringing you in hosting, art, music, entertainment and the visual. How do you communicate aesthetically and to the heart psychologically? That’s where I want to be at.

You’re truly inspirational. I look at you and I think back to the nine soft characteristics and I say, “What are the ones that makeup, Drew?” The top one on my list is drive. There is a drive and a need for achievement. There’s this growth mindset that you exhibit. There’s a drive to be better every day, continuous self-improvement that you have for yourself and you pass on to your clients and everybody around you. I know that after this conversation with you, I’m better than I was before this and there’s this opportunity to learn as much as you can and contribute to the well-being of that community. Drew, thanks for joining me on the show. It’s truly been an amazing conversation. It’s so exciting to learn from you and I look forward to having you back on and we can keep this conversation going.

The post-show being successful, we’re going to get back together. You’re awesome. I can’t wait to see where this goes.

American Jedburghs went out to form the foundation in the United States Special Forces and the Special Activities directorate of the Central Intelligence Agency. Thanks for reading the Jedburgh podcast. We’re brought to you by the Talent War Group, an executive search firm and talent advisory. We’ll drive you to attract, retain, and develop top talent with services like leadership development, talent acquisition, and keynote speeches. We work with you and your teams to create talent solutions to business problems.

To get started, visit TalentWorkGroup.com. Join us for a new episode on Spotify, Apple Podcasts, Stitcher, and Google Podcasts, or wherever you get your podcasts. If you like what you read, give us a like and leave a review. Follow me, Fran Racioppi, and the Talent War Group on LinkedIn, Facebook, Twitter, or Instagram. Send your comments and inquiries to Info@TheTalentWar.com. As former members of Special Operations Forces, show and Talent War Group contribute a percentage of all profits to the Special Operations Warrior Foundation supporting the families of our fallen warriors. Thanks for joining us on this episode. How you prepare today determines success tomorrow.

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