100: 100 Episodes and Beyond

“Helping other people do what I did without having the painful experience that I had is what I wanted for others, to both help them understand themselves and get to the business side of things right.”

Know Pain Know Gain is at 100! 

Another milestone has been added to our journey together and this is because of your loyal support and unending encouragement. No podcast, no show, no endeavour would have any success by itself. THANK YOU VERY MUCH for tuning in weekly to Know Pain Know Gain-Entrepreneurship Made Real! 

A big THANK YOU also to Podcast Magazine for naming this podcast, “Editor’s Pick”. 

Stay tuned as we move forward together to 100 episodes and beyond.

Look forward to more great and authentic entrepreneur stories to move past all the unnecessary pain in your journey and head straight to making a career path that brings you success and satisfaction. 

Jay has been interviewing a number of business geniuses for the past 99 episodes. But who is this man behind the mic? Today, Jay sits as his own guest in his own show. Don’t miss out on this special treat!

In this episode, Lisa Cherney, Founder of the Get F*cking Real Podcast interviews our very own KPKG host, Jay Rooke. Jay and Lisa discuss: Jay’s life in various roles- as an attorney, as a chef, as an entrepreneur, and as a coach and the lessons learned in decision-making, engaging in personal development, transitioning from corporate to entrepreneurship, finding clarity when everything starts to fail, revitalizing strength despite overwhelming emotional agony, getting out of survival mode, finding a career that align with your higher self, internalizing and harmonizing every aspect of your life, and so much more… 

Episode Highlights:

  • 00:00:25 Tables Turned
  • 00:02:36 Jay Behind The Mic
  • 00:11:40 The Big Decision
  • 00:24:10 Fortunately Unfortunate and Back To Corporate
  • 00:31:49 Jay’s Personal Development Journey
  • 00:40:16 Survival Mode To Further Down The Spiral
  • 00:49:22 Grandma’s Message
  • 00:56:46 Death and Rebirth
  • 01:05:50 Internalize and Harmonize
  • 01:10:36 Entrepreneurship and Self-fulfillment 
  • 01:15:40 Go On A JayWalk


Connect with Lisa:

Inspirational Quotes:

“A lot of what keeps us stuck is the guilt for a million different reasons.”

“Survival mode is not the healthiest place to make informed decisions from.”

“For many people, closing their business is more emotionally traumatic than losing a loved one...”

“Helping other people do what I did without having the painful experience that I had is what I wanted for others, to both help them understand themselves and get to the business side of things right.”

“There’s only one way through this: This emotional pain is going to stay present until I integrate and harmonize this entire part of my world.”

“We don’t get to there without starting to teach and practice what healthy masculinity looks like.”

“Intuition is great and doing deep personal work is great. And we can also accelerate how we get there and move in and out of that a lot more effectively when we’re laughing than when we’re guarded and trying to protect ego or get the story right. And it allows us to forgive ourselves so much more quickly than traditional ways.”



Jay Rooke: Hey, what’s up? Know Pain, Know Gain listeners I’m your host, Jay Rooke here. Know Pain, Know Gain was named in Editor’s Picks by Podcast Magazine, so we wanted to say thank you to the whole team out at Podcast Magazine, and thank you to all of you, the listeners for this entire time for making this awesome thing happen. So with further to do, here we go, Episode 100.

What’s up everybody, welcome to the 100th episode of Know Pain, Know Gain: Entrepreneurship Made Real. I’m your host, Jay Rooke, thank you so much for tuning in for the last 99 episodes. We are here today with Lisa Cherney, the Queen of Clarity and host of the Get Fucking Real Podcast. Lisa, thanks for joining us today.

Lisa Cherney: I am so excited to be here.

Jay Rooke: Same here. Folks, here’s the deal, for the last 99 episodes, you have heard me ramble on and ask questions from all sorts of bright entrepreneurs and thought leaders about launching one’s own business, personal development, emotional intelligence, all that good stuff. We’re going to flip the seats here for episode 100, and I’m going to give the steering wheel over to Lisa who is going to interview me for this episode. So deep gratitude to Lisa for being here today. And thank you so much for playing in our sandbox.

Lisa Cherney: I am so happy to always help people GFR. So let’s do this thing.

Jay Rooke: And Lisa, why don’t we do this before we kick off? We’ll start the episode the way we always do, which is you telling folks where you’re dialing in from today.

Lisa Cherney: Sure. I’m in Southern California, Orange County between LA and San Diego.

Jay Rooke: Awesome. And folks, we usually don’t talk about current events, all that much in the show to try to keep things evergreen and relevant for longer periods of time. But I think given where we’re at today, it’s noteworthy. So today is April 28th, 2020, and I’m in California. So we’re on day, God knows what of the quarantine. And I’m at home with five year old boy, girl twins. So I’m gripping to my final thread of sanity. And as most of us know, especially all the entrepreneurs out there that we are in a very fluid and dynamic time, which I think will add a lot of light and reflection for today’s conversation. So with that, Lisa let’s do this.

Lisa Cherney: All right, Jay, I’m super excited about this. All right, so I don’t know if your listeners know that you were an attorney at some point, but I actually would love to hear how you even decided to go into the law, because I think that that’s going to add some color in terms of exiting the law as well.

Jay Rooke: Yeah, no, that’s a fair question. So I think it kind of aligns with a lot of your GFR work, I wasn’t particularly deliberate about my path at that point in time. I knew I had ambition, I was bright, I wanted to do something and didn’t really know where I fit in in the landscape. And so I was like, all right, well, I’m smart, and I’d like to make some money. And other people seem smart and are making good money as an Attorney, so let’s go to law school. And it was really about that deeply thought out. So the path there was to just try to get to somewhere else or that next level, but it was never like a deep calling of mine that I wanted to pursue in life.

Lisa Cherney: And that’s so interesting because your kids are young, my kid is a freshman in high school and we are just starting that college journey. And the first step when you’re a freshman they say is to do some career, career research. And so my husband was sharing with my daughter about how he chose his career, and it was basically, I want to be an engineer. Then said: “Well, chemical engineering is less crowded.” And my husband’s like: “Okay, I’ll do that.” Not much thought at all in terms of what that looks like for a career. It’s what his dad did. And of course now he’s spent 20 years unraveling that decision.

Jay Rooke: Yes, totally. What’s the round ass line and that life is something like getting dropped off in the forest and trying to find your way back home or something to that effect. And I think that’s very much true vocationally for me.

Lisa Cherney: Yes. And so when you were in school, were you kind of like, what the F am I doing here? Or you just sort of did it? You know, you didn’t really question it along the way,

Jay Rooke: Yeah, I didn’t question it too much. And I was so, myopic at that point in my understanding of the world and seeking permission as far as, Oh, where will I be allowed to play, and apply my trade, and make money and all that type of thing that I didn’t have a particularly expanded view of what was possible. So it was just like, all right, Yeah, let’s do this. And I guess this is what life looks like.

Lisa Cherney: And did you, when you look back on it now, where did that unconsciousness that you were operating in, how did that show up in your life? Was there a physical manifestation? Were you a little bit depressed and didn’t know it? Come on now, looking back, it’s like, yeah.

Jay Rooke: I’m laughing because I’ve had chronic pain for most of my adult life, and in the last, probably six months, it went away.

Lisa Cherney: Wow.

Jay Rooke: And I didn’t pay attention to it at first. And then all of a sudden, one day I was just, I was finally found some old papers in physical therapy stuff of mine. I was just like: “Oh, wait, I haven’t been in pain in a really long time. Isn’t that interesting.” So I would say, physically, it manifested through a lot of chronic pain things, definitely some depression going on, definitely like some pent up anger, rage, resentment around like I wasn’t in touch with my feelings super well at that time or body, but all the signs were there around intuitively like, Hey, I don’t like this, this isn’t right for me. I’m not enjoying this type of thing, but I wasn’t hearing the signals properly. And I also had just had a lot of the mind of a 22 year old at that time, as far as, Hey, maybe this is what adult life looks like. And maybe it just sucks for everybody because we’ve got, you know, coming from the baby boomer generation of like, Hey, that’s how life works. We’re not here to have fun or express ourselves. Just put your head down and show up to work for however many years. And that was what I was operating under.

Lisa Cherney: Maybe it just sucks for everyone. Okay, so what happened after law school?

Jay Rooke: So I started practicing law. I got this really cool opportunity to be an attorney for the city of New York. I was in their special litigation unit, which was defending the city in high exposure cases. So picture police shooting goes wrong, a city garbage truck crashes into a parade, those types of things. And it was exciting and so much as had I gone the private firm route at a big law firm or whatever it might be. It might’ve been years and years until I was allowed to do my own depositions as it were, I think I did somewhere in the lower hundreds of that. I think I had a caseload of around 75 cases. And the cool part about it was you were just given a tremendous amount of opportunity and responsibility straight out of the gate. But everything that I was experiencing in that law school time just kept bubbling up deeper and deeper and more and more. So the intensity of that, you know, late depression and frustration about not being able to plug in and get my place at the table in society as far as feeling in my own flow was getting stronger and stronger. And then it was interesting because I started, I got an introduction to a guy by name of Dr. Brian Schwartz who was working in Connecticut at the time, and started to work with him and trying to figure out, Hey, why am I so upset? And from the outside, everyone’s like, Oh, lucky you, you get to be an attorney and this is awesome. And inside I’m just like, you have no idea how much this sucks and how unhappy I am. And also the shame and embarrassment of like, wow, did I just fuck up on a pretty global stage around pursuing such a big career that I’m now completely disenchanted with. And I started to look back in time and I realized, Oh, wait a minute. When I was in law school, I was reading cookbooks more than I was reading my legal books. I had my third year of law school. I chose my classes based around what would allow me to be free at 10 in the morning so I could watch Mario Batali, his cooking show. I was having huge dinner parties during law school and those types of things. So starting to look at all those cards, it was just like, Oh, interesting. I really love this. I’d always love food. It was always a measure of comfort for me as well. It is obviously for many people, but that was a huge avenue for me. And I started to try to get brave enough to explore, Hey, could I go this route?

Lisa Cherney: So what kind of doctor was Dr. Brian Schwartz?

Jay Rooke: Psychologist. If you’re familiar with Andy Graham, he had done some work in that field, but then took that and ran with that and made his own system. I think it was called Career Success DNA or Career DNA is the company that is now running out of China.

Lisa Cherney: Okay, so you didn’t hire a therapist? You hire someone that just helped you look at your career.

Jay Rooke: Yeah, yeah, yeah. With a heavy dose of like a psychological introspection in parallel with it.

Lisa Cherney: Yeah. Very, very nice. And how long–

Jay Rooke: I knew myself as a career coach at the time, but then, you know, that woven into it.

Lisa Cherney: Which made it probably accessible to you from the context you were coming from?

Jay Rooke: Exactly.

Lisa Cherney: And how long into the city of New York job did you seek out the support?

Jay Rooke: Twoish years.

Lisa Cherney: Twoish years. Yeah, I think it’s relevant because it’s like, how long do we tolerate things before we reach for support or just even admit, my things about confessions, you know, the show is about confessions and the GFR commandments are about confessions and it’s kind of like a student of it because it’s like, now I’m realizing, Oh, sometimes it’s just in our head. We barely will confess to not being happy, but it doesn’t even stick. It barely flies by our awareness. And how long does it fly by before it slows down enough in the scrolling to just land for a minute and have us take action on it.

Jay Rooke: To that point in the two memories that I come back pretty well. I think a particular morning where I was scheduled to do something like, probably a three or four hour deposition of a 13 year old girl that claimed that she was raped in the hallway in a school. And part of the job had to go question by question all the way through and I’m just like, I hope I can get fired today before this deposition happens. And I realized, Oh, well, that’s probably not a good sign when I’m hoping someone else will take my job away from me so I don’t have to do it anymore. And then the other interesting point around here, how long will people tolerate it? I think what freaked me out was watching how many people were in their 50’s and 60’s equally hating the job, but staying in it. And the thought of becoming that person terrified me. And I think back to when I finally went in a new direction and resigned. How many attorneys came up to me and said, Hey, I’ve got a spouse, kids, mortgage, whatever. I’m so happy you did what you did for you. I wish I could have done that for myself. And that was just a very poignant moment.

Lisa Cherney: Yes, yes. It is very poignant when people around you say, I wish I could do what you’re doing. Because I think you’re going to get that reaction from this episode when it’s–

Jay Rooke: True.

Lisa Cherney: Final part of our conversation, I think you’re going to get that same reaction, I wish I could do what you’re doing. Yeah, awesome. So at some point through the support of Dr. Brian Schwartz and his work, you came to the conclusion, I need to leave law, or I want to leave law and I want you to go to culinary school?

Jay Rooke: Right.

Lisa Cherney: Is there any nuances to that decision making process that you want to share or just take it now.

Jay Rooke: I guess one thing I’ll throw out is starting to look at how synergies show up in our lives, and this will become relevant when we talk about the restaurant later as well. I took the train back from Connecticut to New York City that day. I’m so in my head, it’s off the charts this thought of like, wait a minute, am I really going to leave this job as an attorney to go to culinary school and all that type of thing? And it wasn’t like a happy revelation, it was more like hand wringing and like, Hey, am I about to make another mistake? And is this brave? Or is it stupid? And maybe it’s some combo of the two. And I decided just to look it up, and it turns out that there’s a culinary school in Manhattan, not far from me that was doing this work study program where you would work for them and learn all these things. But in exchange, you got free tuition. And I was just like, wow, that could not be more perfect. So hooked that up and made that happen. And that’s how it all started.

Lisa Cherney: So it felt like a synchronicity or a sign?

Jay Rooke: It did. Yeah.

Lisa Cherney: Awesome. Awesome. And did you have friends that had attended those parties? Those dinner parties that were like, Oh, my gosh, I totally could see you doing this.

Jay Rooke: Yes. Yeah. No, 100%. There’s this amusing aspect coming out aspect. I think when we finally shed some of the illusions we have about ourselves where we think it’s some kind of big revelatory discovery for ourselves and everyone around us is like, no, dude, we’ve been watching this for the last 10 years. This is what we expected, you know?

Lisa Cherney: Nice. And how did your parents react?

Jay Rooke: A lot of confusion, a lot of challenges. And my wife and I think we had gotten married that year as well, I want to say I was 25. And so I’m sure there was a lot of like, Oh, boy, what just happened? And I think shared anxiety, but also from a spot of like, again, going back to that baby boomer lifestyle or mentality around, wait a minute, what is this person doing? And I think it was probably seen by most externally as more of a throw away than it was like a chrysalis moment and sort of evolution than something different. By the way, Natalie’s parents ever articulated any of that more. So that was just the sense of like, all right, what’s going on here? And like, Hey, why are you doing this?

Lisa Cherney: So are you saying that they kind of minimized it? Like, he’ll go back to law kind of things. It’s just a temporary thing? Or is that what you’re saying?

Jay Rooke: I think it was probably a lot of sense of lost opportunity. I think so many people look at the career path or perhaps income potential of an attorney and wish that for themselves. And then it was like, Oh, wait, why are you throwing all of this away to work with your hands and do this type of thing when people wish they had these opportunities that you have?

Lisa Cherney: Yes. Great. Which causes guilt.

Jay Rooke: Yes.

Lisa Cherney: Yes. Which is a lot of what keeps us stuck is the guilt for filling in the blank for a million different reasons. Right? And I was funny, I’m glad your wife, because I was thinking, okay, at what point did he meet his wife? And so she married an attorney, is that what you’re saying? And then within that year is when you decided to leave law.

Jay Rooke: Yeah.

Lisa Cherney: Yeah. My husband, I married a Chemical Engineer and then he quit his chemical engineering career to become a chiropractor.

Jay Rooke: Oh, no way.

Lisa Cherney: Yes. And then went back, had his hand in chiropractic, opened up a couple of practices, loved the work but hated the insurance companies and served all the bureaucracy that came with it. And then he wound up back in engineering, but in the health industry and a company that loves that he has the doctorate of chiropractic. It’s fascinating to watch our journeys where life takes us, because when we get to the end of your story and where you are now, it’s like, this is what my GFR show is about that’s why you’re going to be on it. It all makes sense. You had to have, Oh, I went to law school just because it seemed like the right thing. And then you had to have the, I left law school, all of the things that, I was just gonna say, all the things that are going to help you support people now in this new phase that you’re moving into, it’s like these experiences are critical that you had.

Jay Rooke: 100%. And it’s also fascinating to me to look in retrospect and be like, yeah, it’s cool to spend seven years of your life. And however many tens of thousands of dollars to go this route without much checking it. But if you try to go in one try to go in a different direction, how much of the checking there is? And I think back to like, Oh, well, if I could have just done this same introspection at the start of this journey, there would have been less bumps. It probably all had to happen, otherwise I couldn’t have gotten there. But I think back if there’s an ideal way through this would be to start to tap into some of those things before.

Lisa Cherney: Yes. Yes. And of course it’s parents, we’re always looking at how we can mitigate for our kids. And then at the same point, it’s like, you know what? They’re going to have their own F journey, and they’re going to make their own mistakes and maybe they avoid a mistake one through four, but then they start with number five, it’s inevitable.

Jay Rooke: Yup.

Lisa Cherney: Okay. So you make the big decision that you’re leaving your role with the city of New York and you’re going to go into this work study program with this culinary school. Now, did you feel like I’m going to do this and then I’m just going to feel so much better almost like that Nirvana state that we are often seeking. Like, you made the change and then what happened? How was it where you’re like, this is awesome or what?

Jay Rooke: Yeah. It’s really funny because I’ve gone through so many times in my head, but your question just allowed me to see this in a new way that I’ve ever experienced, which I was still chasing nerves, or happiness, contentment, peace, whatever that might be externally for me. So there was still a lot of wounding and depression from the whole law thing and like, Oh, we know what’s going on there that I didn’t really clean up and then just dragged into a next scenario. So yeah, I was seeking that magic bullet around like, Hey, this is going to be the thing that allows me access to the happiness that I watch other people have that I haven’t been able to think my way through yet, this should solve things. So yeah, there’s definitely a lot.

Lisa Cherney: So how long was that journey of being a student in the culinary world?

Jay Rooke: I want to say in a year and a half, two year range. And I will say it was one of the happiest times of my life. It was just an awesome learning environment, stimulated in every direction, around amazing people that love what they do. It was interesting. I never felt super cool on the subway in my suit and an attache case going into law. But when I got on with my chef’s pants on, and the knife roll and those types of things, I felt like I was a superhero and that was a really cool experience.

Lisa Cherney: That’s awesome. That’s an awesome feeling. Men in uniform, they say. Yeah, that’s awesome. So when you entered the culinary world, did you know what you were going to do after? Did you like, or you hadn’t really gotten that far? You’re just like, I want to cook.

Jay Rooke: Once again, going to see another theme of Jay making big, brave leaps without thinking too much before jumping off the cliff. So my mentality at the time was I was going to open a whole food style store. And really interesting is that this past week with the pandemic and everything, I’ve been cleaning out my garage. And I came across my notes from 2004 where I was talking about opening one in Hartford before whole foods had come into town, and my vision of all of this, and I wanted a small batch. I wanted connections with the farmers. It was all going to be all about food, education, lots of prepared foods. So that was my vision. And then once I came out of the, I had done both the culinary management and the culinary arts side of it. So learning how to do the cooking but also on the business side. And I’ve realized how bad the margins were, and that it was going to take me about a million dollars in external funding to create something like this to maybe pull off a 6 to 9% margin. And so I was just like, yeah, that’s not happening.

(Commercial Break) So why don’t we do this? We’ve been running for a bit. Let’s take a quick pause and pick up the culinary story right after we hear from some of our commercial sponsors. Folks, a special thanks to our guest host today, Lisa Cherney, we’ll be right back after the break.

Jay Rooke: Hey everyone, Jay Rooke here, we are here today with Lisa Cherney. We thank you so much for being one of our sponsors. Lisa is the Queen of Clarity and host of the Get Fucking Real Podcast. As you know, here on Know Pain, Know Gain, we like to talk about all things that are real and authentic and shed some of the layers of falsity city about entrepreneurship. Lisa, tell us about your Get Fucking Real Podcast and your movement.

Lisa Cherney: The show is really about saying that struggle has a purpose when it comes to the mission driven entrepreneur. So we tell really crazy stories about people that have been through the ringer and come out the other side, really on purpose, more than ever before.

Jay Rooke: And when you talk about that purpose, one of the things that I think is interesting is that a lot of us know where we’re being inauthentic and it doesn’t feel right, but we’re struggling to just surrender and get through that other side. Do you have any type of resource that folks and start to use in addition to your podcast, to start to tap into that messaging for themselves?

Lisa Cherney: I realized that there were 12 ways that the mission driven entrepreneur that I’ve been coaching for 20 years would get in their way over and over again, Jay, where it would keep them from even using some of the investments they made and really getting out there with their mission. And those became the 12 GFR Commandments and “confession” questions. And it really is the roadmap for getting real so you can have more impact and more income in your life.

Jay Rooke: Folks, check it out, that’s the link you gotta go to. As you know, on the show, we talk about Entrepreneurship Made Real, at least as part of your gateway to get there, starting to explore yourself, learning more where you might not be fully authentic with yourself. I highly recommend checking out her podcast, following some of those conversations and downloading her resources so you can explore yourself further. Lisa, thanks so much for helping our audience today.

Lisa Cherney: Thank you.

Jay Rooke: And Lisa, one more time. Where can they go to get that download?

Lisa Cherney: Go to gfr.life/12c, 1, 2 and the letter C for commandments.

Jay Rooke: Awesome folks. Now we’re back to the show.

Hey everyone, welcome back to Know Pain, Know Gain: Entrepreneurship Made Real. I am your usual host, Jay Rooke, but I am blessed to be guest hosted today with Lisa Cherney, who is interviewing me. Lisa is from the Get Fucking Real Podcast and the Queen of Clarity. Lisa would love to continue the conversation.

Lisa Cherney: All right. So now we’re getting into it, you have this culinary education, you bag your first idea of opening a whole food type store because the margins were so bad. So now you’re like, okay, you’re sitting there with your arms outgoing, now what?

Jay Rooke: Yeah. One of the things that I’m missing the word here for, it’s cocky, or arrogant, or pretentious, isn’t exactly it, but it’s somewhere in that direction where at this point in life, I’ve still got a little bit of a chip on my shoulder around, well, I’m a freaking Attorney, God Damnit. I know I’m not going to go and cut onions for $7 an hour or whatever it was at the time. And I looked back and I wish I could have dissolved that a little bit better to give myself the permission to work somewhere for however long it needed to be, to truly find my space and not tripping on. I was so caught up in my head around that time working for a small amount of money was just an utter failure and reinforced any of that legal stuff. So I think back, and I’ve got two jobs that I regret not doing in my entire life. One of them was working at Italian pizza shop in Hartford where I was given an opportunity, but the pay wasn’t great. And I thought it was below me, like total moron. So that’s how it was kind of kickin it.

Lisa Cherney: Yes. I love that. I mean, not many people say there’s two jobs I wish I took but I didn’t take. And I would have loved to work in a pizza shop, pizza’s my favorite food. That’s awesome. I just had this intuition to ask you about what your wife is doing at this point in her career, because I feel like when we have those ego inspired decisions, the context is it’s not, yes, I’m in a freaking attorney context for sure. But I just wondered too in your relationship that there was also a factor that contributed to, I can’t just take this job at this pizza place.

Jay Rooke: Yeah. A million percent. And unfortunately and very fortunately, my wife has been nothing but the biggest cheerleader and super supportive through this whole process. And when I say “unfortunately” in quotation marks, it’s like that bomber around like, Hey, what should I do? Should I go this way or that? And she’s like, Hey, I support you in doing whatever you want to do. And I’m happy for you if you want to do this. And internally I’m like, ah, I just need someone to tell me what to do. Or somebody clipped my wings a bit here or whatever that might be. But ,no, she’s been wonderfully supportive through the whole process. And I think she has been a real loyal supporter of Jay’s happiness and whatever it takes for Jay to get there, she’s behind. And so there’s been that. But at that point in time, I’m in my mid to late 20’s as a male trying to figure out, Hey, what’s the provider thing that I’m plugging into? And am I a failure in my own masculine pursuit here, if I’m not a primary breadwinner or at least a significant one. And a lot of those marbles were certainly kicking around in my head.

Lisa Cherney: Yeah. It’s an interesting thing to unpack because, would you have had that same, I need to be a provider if you weren’t married and in a relationship at that time.

Jay Rooke: Very interesting. Yeah.

Lisa Cherney: And I think it’s easy to say, no, you wouldn’t, but I don’t know. You don’t know it’s interesting. Where does the ego get fed?

Jay Rooke: Totally, totally. Yeah. I like that.

Lisa Cherney: Okay. So you didn’t take that job. What did you do?

Jay Rooke: Opportunity fell into my lap where there was a culinary school instructor position that was available in Connecticut. And those are usually reserved for the later stages of someone’s culinary career where they’ve worked in kitchens their whole life type of thing and now they’re coming back to teach. So I had no business being there, but it fell into my lap and worked out. So here I am, as an instructor at this culinary school’s kitchen, I was one of the head chefs of the restaurant there, which was hilarious in and of itself. And that run went on for a bit. I had some fun, the school went through some corporate shifts and changed things up. And then I found myself selling wine for a little while to about half of Connecticut, small batch Italian stuff. And that was a super fun job. I very much enjoyed it, but the pay was particularly punishing at that time. And I just found myself kind of my brain just atrophied a little bit. And so decided to go back into corporate and took a job with Merck Pharmaceuticals for a while.

Lisa Cherney: Okay. And when you say back into corporate, I think you weren’t ever in corporate because I worked for T & T and all these big companies. But for you, it sounds like you see corporate as sort of like back into the suit, and like that part of yourself.

Jay Rooke: Nice distinction. Yeah, a hundred percent. And this certain like resignation around, Oh, I gotta go and put the yolk on and do this societal thing. It felt like a non passion project, for sure.

Lisa Cherney: Yes. I just have to say this is eerily familiar to my husband’s journey because before he went back into corporate, he taught at a chiropractor coach.

Jay Rooke: No way.

Lisa Cherney: I think he’s super bright and just got bored and just needs that challenge of a new thing. And so he’s a bit of a renaissance man, as I think you are as well as eclectic interests and stimulations. You’re obviously creative, right? The culinary side of you is super creative, and those juices were flowing, but you also really do appreciate the argument and the problem solving, and yes, yes. And so it was sales that you went back to incorporate, is that right?

Jay Rooke: Correct. Yup.

Lisa Cherney: Where are you parlaying your wine selling experience into that sales opportunity?

Jay Rooke: Something like that. Yeah, for sure. And I think if I were to look back at my cover letter at the time, I probably said something like, Attorneys are salesmen as well, except we just sell ideas to jurors and judges and that type of thing. And trying to parlay that, I want to loop back. Is this such a fun conversation because I’m actually learning things about myself here when you mentioned the creative part. So that’s been a lifelong challenge for me and has been being gifted creatively. And what I mean by that is, I grew up fairly working class. I have family in Western, Massachusetts. In those types of career pursuits, I think we’re viewed as much more risky, much more irresponsible let’s say. It seemed unsafe to me to ever allow those two parts to meld or to go in that direction. I think when I’m saying go back to corporate, what I’m really saying is to crush the creative. It didn’t feel that that was the spot where I was going to get to play with it.

Lisa Cherney: Ooh, that’s juicy, crushed the creative. Yeah, my husband’s creative, he had the opportunity to pursue music as a degree playing trumpet. And his parents, there was no way that that was happening. Yeah. Yeah. That’s awesome. Okay, so the suit is back on.

Jay Rooke: The suit is back on. Yeah.

Lisa Cherney: And no more looking like a rockstar in your gear from, and you’re doing pharmaceutical sales?

Jay Rooke: Yup.

Lisa Cherney: Okay. So how long until your soul was dying?

Jay Rooke: Giving the reputation of the industry that you would think it would be much worse, I would say that was one of my few times where I was vocationally happy for the most part, doing that type of work. It was a lot of great people learning a ton. It’s funny though talking about these industries that I’ve chosen because if we look at law, law is one of the most broken things out there as far as our legal system and how it actually helps or hurts things, and then we go over to healthcare. So I would visit about a hundred doctors on my route and it was just fascinating to me. You get to just learn how completely and utterly broken the healthcare system is. And in so many ways, but for me around that, I just realized that I wasn’t going to move to Pennsylvania. Let’s pretend I had an opportunity to move up in Merck or something like that. So I was kind of limited in what I could do in the field, and I just didn’t want to be knocking on doctor’s doors for a super long time. And I want to say, right around that time I was probably close to 30 and I’ve always wanted to check out California, and so made the pitch to my wife to move out to California. And then that started the next chapter.

Lisa Cherney: And what was your career vision for California?

Jay Rooke: Let’s jump again.

Lisa Cherney: That emoji somewhere in the show notes, hands up by your shoulders.

Jay Rooke: Yeah. I was committed to getting a job before we made the leap, but there wasn’t much of a vision. I guess you’re going to get it going back to this intuitive coming out. I felt like I was more aligned with a lot of the values of what I saw represented by California at that time and what some of the people were doing. And I think that was probably subconsciously for me, some vision around, if I’m going to fulfill myself, or get to play with these other sides to me, I’ve got to get out there around those people.

Lisa Cherney: Okay. So was there a particular teacher that you were connected with at the time that was out here?

Jay Rooke: No. No.

Lisa Cherney: Okay. So give us a little, let’s park the clouds and give us a glimpse into your personal development journey that was going on in parallel to this. So what were you pursuing at this time? So this is now going from pharma to California, question mark.

Jay Rooke: Yep. Yeah. So I think at this time, I still thought that all questions could be solved in my head. It was lots of like cerebral and intellectual delving, the personal development work was much more around exploring archetypes or stricter levels of psychology, lots and lots of self help books around, Hey, why am I not happy? Hey, how to find the career that you love? And those types of subject matters that would get me thinking about things, but I’ve still wasn’t connected to my heart space. I still didn’t really understand my bigger journey. I was still operating way too much inside the frame and had all of that piss and vinegar of a 30 year old male trying to make his way in the world. So I was trying to use force, and work, and can do to solve this problem.

Lisa Cherney: Okay.

Jay Rooke: Later in the years, it would soften and turn to more understanding the emotional side of things in my heart, in my own healing process, et cetera. But at that point in time, they weren’t connected.

Lisa Cherney: And it’s great to stay connected to that piss and vinegar young man, because that’s where you’re maybe meeting some people in your work in the future. It’s in that place where they’re in that space.

Jay Rooke: Yeah. I was talking to my spiritual guru guy the other day and he was talking about one of the things that I have going for me is having a foot in both of those worlds all the way through. So being able to understand both sides of the house and relate to people going through that. So yeah, that resonates.

Lisa Cherney: Yeah. Awesome. Okay, so now we’re out in California with a vague notion of what you’re going to do for a career. So how quickly did you see the real reason that the universe had moved you to California?

Jay Rooke: So this is O8, and I don’t think the real reason probably came up until a few years ago. I was still pretty operated under the radar during those years and had a, it was O8 so it was rough, everything’s collapsing. And then I got into another job in the energy sector after that. And one of the things that I was just realizing with all of my coworkers is I just felt like I was from a different planet, and I’m watching all these people put their heart and soul into this work. You know, work 50, 60 hours a week, seemingly enjoying it, or at the very least not wanting to kill themselves over it. And I just felt like, what is wrong with me? Why can’t I fit into this? Where am I off? So I think part of what took me so long to understand what that big picture was is that I was viewing it as my mistake or my error more so than it was learning. Oh, wait, no, no. I’m supposed to plug in over here, not there. I’m supposed to use these skills, not those. So that’s what was kicking around a lot for that time.

Lisa Cherney: So you’re saying that your feeling of being a personal failure or making another wrong decision, quote unquote, had you shut down in some way to really what? The work that you were supposed to be doing on yourself.

Jay Rooke: Yeah, definitely.

Lisa Cherney: The energy sector, okay. You have a very eclectic, I could just see you now, you’re going to have like 50 clients and you need to be able to say to half of them, Oh, I did that job. Oh, I did that. Okay, so what happened next?

Jay Rooke: So I want to say, I think they get laid off or resigned and I’m just like, alright, you know what? I laid that dream on hold about doing something culinary related and being my own business owner. And I was just like, screw this. I’m like this, needs to happen. And I don’t care how, and so I just committed to somehow, some way, I was going to do this–

Lisa Cherney: Do this was a restaurant?

Jay Rooke: Something entrepreneurially related in the culinary world. I didn’t exactly know what it looked like at the time. Food trucks were just starting to come on the scene, and I thought that’s what I wanted to do. Ironically, given the lending standards of the time, I couldn’t get a loan for one which worked out great in retrospect, because I would have had like a hundred thousand dollars debt, and then that whole thing and then be stuck with a truck. But anyhow, so I can’t make it happen.

Lisa Cherney: Unless, maybe it might have been successful? I don’t know.

Jay Rooke: Also true. Also true. Yeah, for sure. For sure. Well said. Yeah. So I’m there and I’m just like, ah, I really want to open my own business. I don’t have the capital to do this. And I really set an intention before I went to bed that night and I was just like, God, please show me something that just makes this happen, please. Wake up the next morning and I get this idea. I’m just like, wait a minute. What about businesses for sale on Craigslist? And I happened to hop on and check. And it turns out in the town over there’s a Marina that has a restaurant in it. The owner of the Marina wants the restaurant functional for his patrons and has traffic, and flow, and all that stuff. But doesn’t want anything to do with the day to day running of a restaurant. I, on the other hand, don’t have a Marina. Want everything to do with the day to day running of a restaurant so we can act, and pretty quickly this vision comes together that I’m going to pursue this. And I think back, I went with a buddy of mine, we checked it all out, and we’re trying to do our due diligence, and we grabbed a beer afterwards and I said: “William, what do you think men, should I do this? Or what?” And we keep kicking it back and forth. And the final line that we agreed on was how can you possibly lose money with a bar and grill on the water in California? Well, ladies and gentlemen, we found out how, trust me. So thus begins the restaurant chapter.

And why don’t we do this? Why don’t we take a quick pause and hear from our commercial sponsors. This is probably a perfect transitional spot. Folks, you’re here on the hundredth episode of Know Pain, Know Gain. Were gracious enough to be blessed to have Lisa Cherney guiding the interview today. We’ll be right back after the break.

(Commercial Break) Hey everyone, Jay Rooke here, and I’ve got something that I’m super excited to share with you guys. Here’s the deal. I typically work with clients seeking to harmonize their personal development, entrepreneurship, and spiritual growth. And I’ve just created a new experience to work with me one on one, it’s called the JayWalking Session, which is basically a creative brainstorming session designed to help you get clarity on an issue that’s holding you back right now. What’s unique about it is that I had out into nature for our call. The experience goes around 90 minutes. I record the call so that you can be more present during conversation. And for the launch period, I’m offering a money back guarantee. Jaywalking sessions are perfect for spot coaching where you’re not seeking a long term retainer, but you need some expert support to guide you through a decision, explore new perspectives, or to help you envision what you can’t see for yourself right now. Some examples that would be good topics for Jaywalking sessions are maybe you’ve got a big decision coming up, or you find yourself at a crossroads and you’re seeking an answer. Perhaps it’s time to reframe a past situation and let go of an old story so that you can own your narrative, or maybe you’re thinking about launching your first business. All Jaywalking sessions have roughly three phases. Phase one is listen and learn. We’ll spend some time getting to know each other and have a deep discussion to gain clarity on your topic. Phase two is explore and envision. Now the conversation shifts to brainstorming or what I call ideal popcorn. During this phase, we explore new possibilities and craft potential solutions that feel resonant and are preferable to your current situation. And lastly, phase three is execute and embrace. This final piece is all about laying the groundwork to help you embrace new perspectives and start taking action towards your goal. So if there was something we could wave a magic wand out right now, what would that be for you? Whatever you choose, make sure you don’t let your current circumstances dictate whether or not you grow. Allow yourself to be supported, get the expertise you deserve. Don’t go it alone this time, join me for a Jaywalk. To learn more and to book a Jaywalking session, go to jayrooke.com. And now back to the show.

Jay Rooke: Hey everyone, welcome back to Know Pain, Know Gain. In our 100th episode, we are here today with Lisa Cherney, from the Get Fucking Real Podcast. Lisa, we were just about to kick off into the launch of the restaurant. Where should we go with this?

Lisa Cherney: Well, you and your buddies said to yourselves, how can we lose with a bar and grill on the water in California? And we were able to answer that, unfortunately, within a short period of time. Tell us what happened.

Jay Rooke: Yes. So many things. Yeah, I think the noteworthy part is we opened the restaurant with $11,000 on a credit card and got to cash flow break even by month four. So there’s some massive achievement level lurking in there somewhere.

Lisa Cherney: Yeah, we call that food strapping, folks.

Jay Rooke: Totally, totally. Sharing with my wife the other night, she was saying, I don’t think you’ve still healed from the trauma of the restaurant. So the restaurant chapter was pretty life-defining for me in many ways. And despite the fact that it only lasted for a short period of time, it was probably the most intense experience with life every second of everyday that I’ve ever known. I don’t think my emotions have ever been higher than any point in time. I had an old culinary school instructor who said that working on a line in New York City, he goes: “Start trapping as fast as you possibly can. Now go a little faster. Now go just a touch faster. And now someone puts a gun to your head and says, you slow down 2%, I’m going to pull the trigger. And that’s what a 10 hour shift is like the whole way through.” That experience or that vignette rather pretty much played out as true. So what I know now in retrospect that I didn’t fully know then was, I went into survival mode pretty quickly, which anyone knows survival mode is not the healthiest place to make informed decisions from. And if there’s a tale to my culinary time, or the restaurant time, it was that I didn’t know how to think as an entrepreneur and a business person. So I had the passion down, I had the work ethic, I had pretty good vision and creative ability, but that last portion was the elusive one, which ultimately proved to be the downfall of the venture. But I knew we were working against the clock, and once you open a business with employees in any real types of bills, you just watch the cashflow. It’s like that scene in the National Lampoon’s Christmas Vacation when all the electric meters are spinning like crazy, it’s just flying out. So there was just this sense of panic everyday. And it pretty quickly turned into hundred plus hour work weeks. I lost 30 pounds in the matter of like eight weeks or so. It was just rough. There was this painful and poetic irony of, here I am, I own a restaurant, but I’m too stressed to be able to eat any of the food that are there. So my staff was awesome, they were like, Jay, you gotta eat something today. Or chef, did you eat yet? That type of thing. Yeah. Guide me, I’m not sure where I should go. I don’t want to ramble.

Lisa Cherney: No, no, it’s awesome. And you’re feeling like you’re rambling because you’re going back to the emotion of it. And that’s okay. Was that your chef role? Were you the chef?

Jay Rooke: No. It’s a couple of things that are hilarious to point out here. So yes, I started out in that role and realized I needed to get out of it as quickly as possible. Interesting data point, I was also the only person that was crazy enough to go into a restaurant venture that didn’t have a kitchen. So we had a hot plate, and like a glorified toaster oven, and the kitchen set up, and then we had grills out back, and we use walkie-talkies to get the orders back and forth and try to run things and whatnot. So realized I had to get out of that role as quickly as possible. But what then happened was that all the fear and the anxiety remained there without the physical outlet to turn it into. So now I’m making management decisions versus chopping veggies or whatever that might be. So I’m trying to run things. I’m doing maybe a decent job, but I really don’t know in retrospect, because there were so many wildcards. But I think the opening night probably sums everything up the best, which is, we’re going to open on a Friday and do a soft opening. And I’m doing like my first major food buy and I meet the distributor on Monday and he says: “Listen, we can get it to you on Friday. If you order everything from us.” I’m like: “Well, cuts at a little close. Can we do Wednesdays?” “No, we can only do Friday, but I’ll make sure you’re the first delivery.” So 10:00 AM passes by, noon passes by, making some phone calls, not getting responses, 1 passes by, it’s 2 and I think our seating was at six and I am tripping. So I get on the phone and there’s a lot of heated words said somewhere in the 3:00 o’clock hour and somewhere around 4:30, all the food shows up. So I’m just like, fuck it. I don’t know what to do here. This is an utter shit show, but the show must go on. Let’s get gone. We started to unload it. All of the fucking meat is frozen and I wish this was like a one off, but like literally, every single day something like this would happen for the remainder of the restaurant.

Lisa Cherney: It’s like every restaurant show that I’ve watched, the reality restaurant show that I’ve watched recently. My kid loves them, so I watch a ton of them. Oh, my God. That’s like five episodes, for sure.

Jay Rooke: I know. I know. Totally, this guy shows up with a pizza that night and he says: “Can I eat this?” Here I go: “Hold on a second. Let me get this straight. You want to come into my restaurant, use our flat, we’re in staff, my staff serve you, but you brought the food.” And he’s like: “Yeah.” And at that point, the night was so sideways, I was just like: “Sure. You know what? Grab a seat, buddy. Let’s see what else can go wrong in this gong show.”

Lisa Cherney: I mean, we can go on about the lessons learned and what happened. I think it’s actually worthy of a whole nother show, honestly. And even the emotional healing part would be your wife recently saying that to you, that she feels like you never really healed it. And I’ve said that to my husband too, about his chiropractic. We recently paid off that student loan. And that was part of, the money part is a big, like a tether thing. Yeah. So share whatever more you want to share about that experience. And then for sure want to get to the point where somehow you got the, you pulled the ripcord. Because it could have been so much worse, I imagine because it sounds like it was very short lived and you didn’t take out the big loan and all that, but it still feels like a fucking failure regardless. And somehow you then parlayed that into this. What we could see, now we’re in the current chapter in some way after this, right?

Jay Rooke: Absolutely. I remember I would scream my entire way to work in the morning so that I wouldn’t fall asleep behind the wheel. I had to put the car in park at stop signs and red lights because I’d fall asleep at the intersections.

Lisa Cherney: Wow.

Jay Rooke: Just waking up an abject panic every morning, and it was not sustainable. And I didn’t care, I was committed. Either me or the restaurant was going to die and it was non negotiable to walk away. Like I was committed to making this. So weeks go on, and I mean, we operated with like a thousand dollars on hand for weeks on end. And it was always just as each of these things would happen. The food delivery got missed. Hey guess what? The toilet just exploded. We’re out of cooking gas, whatever it was. Everyday, I knew that there was just one more mistake and then this whole thing was going to come down. We couldn’t sustain really much more. And so that thread bareness of just being barely able to hold on was really palpable. I had a very close friend that was a great loyal brother and arm with me during the whole process that was much more financially conversant than I was. And we sat down, we looked at the numbers and we realized, even if we increase sales by 30%, I was gonna pull like 30 grand out of this over the next year. So I’m just like, ah, this makes no sense to kill myself this hard to work for less than minimum wage, and the stress and everything else. And so I forget what happened, but I knew I wanted to make sure I paid all of my vendors and staff, and be that guy going out. I finally decided to close the restaurant, obviously super painful moments. And it’s interesting because I was having a pretty tough day the other day reading some of the news during the quarantine and reading about all these restaurant closures. And it just brought back a lot of those memories around how for many people closing their business is more emotionally traumatic than losing a loved one. And I’ve had both experiences several times and I will easily say, I will take a human death almost over the business death at times because there’s just so much in it. And so decided to do that. And there’s this odd relief when one finally decides to close their business, it’s like the shame and the hurt of closing it. And there’s this wonderful protective blanket that says, and this can’t hurt anymore. But it does, you don’t know it at the time, but it feels that way.

So I remember sitting in the parking lot on the last night there under a street lamp and just trying to figure out like, Hey, is the honorable thing to do to commit suicide here? I wasn’t suicidally minded, but I had just never been down this corner around like, okay, I’ve lost my money, I’ve lost other people’s money, 10 people are out of a job, all this stuff. And I look at my phone, I’ve got a voicemail from my grandmother and she’s like, I’ll play this. And she’s like, “Jay, this is grandma, I just want to call and let you know that I’m praying and thinking of everyone else everyday. I hope everything is going well for you. You have all our wishes and thoughts, everyday honey. We miss you, and I love you very much and Alice too. You don’t have to call me back. I know you’re busy, but I know you’re thinking of me. Alright, love you. Bye bye.” I’m just like a projectile crying in the car and just hysterically sobbing. One of the tough parts about when this article that I was reading about the business closing is that once it ends, that part of it’s done, but you still have weeks and weeks of 50 to 60 hour weeks of cleaning out all documents, the place, et cetera. So a really tough week coming out of it.

Lisa Cherney: Would you say that message from your grandmother saved your life?

Jay Rooke: No, like I said, I wasn’t seriously, by any means considering suicide at the time so much, it just everything just felt flat. And I think it was a nice reminder that I was loved and I had worth because that’s not where my mind was at the time.

Lisa Cherney: I want to point out that you did contemplate suicide. That thought that you said out loud just now is a suicidal thought. Now you didn’t plan it, it’s actually something I’m not, I wasn’t super familiar with until I started doing my show and saw how fucking prevalent and common it was for people to flirt with that idea to various extents, very, very common it is. So I’ve heard that before. And so I just want to call it out, and I think it’s worth claiming that that is where it got so dark, that that is something that you visited even just a moment, I think really, really shows the depth of where you were and I hear that the regret, and the grief, and how could I do this to other people? And wouldn’t it be better for other people if I just disappeared right now kind of thing. So I think it is worthy of, yeah.

Jay Rooke: I appreciate that spot on. And I really liked that distinction. I think I was in that mindset around like, well, Hey, I wasn’t planning it. So it wasn’t that. And I almost felt like I was taken away from people that were actually in that spot, that that makes sense?

Lisa Cherney: Yeah, you’re welcome.

Jay Rooke: So yeah, that was that. Those next six months were brutal. So we closed the restaurant, a woman who I referred to as my West Coast grandmother that I would take care of and stuff like that passed away. I want to say, the Saturday before the restaurant closed, but I didn’t allow myself to go to the funeral because I felt it was wrong showing to the rest of my team. So deeply regretting that the restaurant closes. My dog, who was my homeboy, died of cancer two weeks later. Two weeks after that, we get a knock on the door and it’s the landlord, and he says: “Hey, I’m sorry, I’m upside down in the mortgage. You guys have a few weeks, you got to find a new place to live.” And it was four weeks of just otter ass kickings. And if you saw me in the months after that, it was just a dead man walking. It was just that thousand yard stare and glaze over the eyes and kind of shuffling through life. And so take another corporate job working for NBC sports. And the sub brand that I was working for was golf now, and I’m a huge golfer, and I hadn’t golfed for a long time in life. It was like getting back into it. And once again, I had a good time and enjoyed it, but just realized I wanted no part of working in the corporate world, and just how unemployable I was, and how it just did not feel the right connection for me.

Lisa Cherney: I just have to point out how fricking nimble you are that you’re like, Oh, I got another corporate job. Because I could imagine the emotional agony that you’re in and like dusting off your resume, picking yourself back up again, being able to do this job search, and I want to acknowledge that too, because I think it’s easy to gloss over, but that is a poignant thing that you did over, and over, and over again. And through this whole story you’re able to pick yourself up, put that suit back on, dust off that resume and make some money, and take a short term. Maybe you didn’t think of it as short term at the time, but even just interviewing for things and having people really feel like you want it must’ve been a huge accomplishment.

Jay Rooke: Thank you. Yeah. And it’s funny because we’ll touch on this later as it relates to what I’m doing now, but I had this moment around like, well, Hey, why do I keep getting thrashed against the rocks in life? And like, how resilient do I have to be? And why do I keep getting put through all of these scenarios? And what I know now is it’s given me a broader ability to serve and understand, but I didn’t know it at the time. So it was particularly tough to go through.

(Commercial Break) Hey, let’s do this before we launch into the most recent chapter of where things are at, let’s take a quick commercial break and we’ll be right back. Hey, it’s voice actor, Kelly Wilson. Thanks for listening to Jay Rooke’s podcast, Know Pain, Know Gain. Hopefully you’re picking up some valuable nuggets. As I share my sleep deprived journey into voiceover full time. Now, if you’re thinking, why would I use a voice actor? Okay, fair enough. Now the obvious commercials for radio TV or the web, you know, having a consistent voice til your branding story can really help your company stand out. What about your voicemail or your phone system messages? Does it really sound like their call is important to you? Now, if you’re selling something and you have an explainer video, is a professional voice marketing those benefits of your product or service? What about your company’s orientation or e-learning videos? Are they dry and boring? Or is there a lovely pleasant voice teaching them? Are you building an app that has voices on it? How’s the audio quality? Everything your brand touches should be professional, even the audio. If you’re looking to Uplevel your production or branding game, I suggest considering a professional voice actor, and it doesn’t even have to be me. I know other voice actors. So if you’re looking for a male voice, or a Spanish voice, or whatever voice, reach out and we can go from there. Now you can hear my demos and get my contact information at KellyWilsonVO.com. If your business would like to sponsor a future episode of Know Pain, Know Gain, check out the sponsorship packages at jayrooke.com. And now, Jay, let’s do this thing.

Jay Rooke: Hey, everyone, welcome back to the 100th episode of Know Pain, Know Gain. I am lucky enough to be being interviewed by Lisa Cherney, founder of the Get Fucking Real Podcast. Lisa, take it away.

Lisa Cherney: Okay. So you dusted yourself off. You found yourself back in corporate and NBC sports doing another thing that you hadn’t enjoyed in a while. So we had the cooking, and now it’s golf. And what I love is that you took this glimmer of something that you love and you were able to make your next career move out of it. So Bravo on that. And at some point, the decision was to leave that and birth what we now know as your, is your current iteration of your career, which is as an entrepreneur.

Jay Rooke: Right on. Yeah. So the old adage around the universe just keeps showing us the same cards over and over again until we learn the lesson. And I think for me, if mine was, the universe being like, Hey, I’m not going to give you access to the happiness you deserve until you clean up the scar tissue and turn inward and start to learn these aspects both about yourself so you can heal others, but also healing yourself. And like that card would show again, and again, and again through life. And at that time, I was working with a coach who I’ve been working with for years and I was getting a ton of benefit out of it. And I’d have worked with multiple coaches and therapists who had been like, well, you’d be great at this. You should do it. And for whatever reason, it just didn’t seem like a legitimate career profession. It sounded like some Hocus Pocus, the way somebody might’ve pejorative referred to a yoga instructor 20 or 30 years ago. And so I just wouldn’t let myself go there, that’s not it. And the more I sat with the discomfort, the more I realized that’s the way it had to be. So I allowed myself to move into that space, and I was fortunate enough that one of the better coaching schools in the world is just down the road from me. I started taking coaching courses on the weekends while I was working at NBC and then spent a year or whatever, ramping up and training to launch what I’m doing now. And at the time, I didn’t fully have, again, once again, did not have any big business vision for what I wanted to do. I was just like, Ooh, I like the thought of this. So let’s do it.

Lisa Cherney: All right. And so this is what you are now calling the corporate version of your coaching business and are going to share with your audience here, probably the most authentic expression to date of where you’re going with, the way that you’re showing up in the world. So take us from the initial brand or positioning what you’re craving and honoring now.

Jay Rooke: Yeah, I appreciate that. Right away I learned that I absolutely loved the work. And then it was one of these things looking in the rear view mirror and everything became clear where I was just like, Oh, yeah, I’ve been doing this with people for years. And this is the role I’ve always naturally taken in all of my social networks and things like that. So that made a ton of sense to me. And once again, where I was kind of floundering was around the businessy side of things and then started investing a lot in myself around working with later stage entrepreneurs and starting to understand some of the nuances that I was missing. And as far as the day to day running in my own business. And then what I realized, I think at the end of last year, it was 2019, realized that I had created a business that I wasn’t in love with. One of the things that I learned along the way was I was trying to figure out, Hey, where do I work in this whole coaching space? And I realized helping other people do what I did without having the painful experience that I had is what I wanted for others to both help them understand themselves, but also to get the business side of the things right. So spend a ton of time in that world and then spend many years focusing on working with people that were leaving corporate to launch their first, whatever that might be. They’re usually bright and good at what they do, but they’ve never run the whole show before. And in parallel leading up to this, I’m starting to go jokingly, call it more off the reservation. I’m starting to do more psychic work. I’m starting to notice how intuitive I am. I’m starting to start to play with all of those types of tools and going deeper, and deeper, and down that rabbit hole, but not sharing it with others or at least not sharing it with others, public brand wise. And I realized that, ironically, here I am saying, I don’t like corporate and I’ve created a fairly anemic version of myself where I’m now kind of being corporate in my own entrepreneurial job and not weaving all this together.

Lisa Cherney: It’s so funny that we keep coming back to corporate as the anti-Jay, and the different things that you are calling corporate, right? Like, law was corporate, and then Merck was corporate, and now you have your own coaching business that feels corporate. And Jay, I think corporate is like, I’m not being my true, authentic self. I’m wearing this suit physically, and emotionally, and holding back in some way. And at the same time, I would say that these versions of corporate have evolved. And so your version of me, corporate and also a coach has nothing like Merck and nothing like when you were an attorney, yet your standards for how real I am, your craving is almost irrefutable at this point. And so it’s feeling, just feeling a lot of wildesness.

Jay Rooke: No, super well said dew point. And yeah, I guess unfortunately corporate is kind of getting the brush all comment, it’s not like anybody in corporate or any corporation ever did anything bad to me. But yeah, I guess I’ve internalized that word to mean the non expression of myself.

Lisa Cherney: And I don’t think you’re alone in that. I don’t think you’re alone. So I think it’s really relevant.

Jay Rooke: Yeah. Yeah. So, yeah. So hit the end of last year, I’ve got this business that I don’t like, and I realized, fuck, I do not want to go through another rebrand. I’ve done this so many times now, can we please just let this be.

Lisa Cherney: But you haven’t, you have not gone through a rebrand in your own business just in your life.

Jay Rooke: Totally. Yeah. Well said, well said. Yeah. What I decided at the end of last year is I’m going to kind of wind everything down to rebuild it all. It’s going to be pretty much similar, but there’s going to be nuances, and I’m gonna try to lead with this whole holistic approach. It’s Christmas Eve last year, and I’m just feeling super heavy about all of this. And it’s two in the afternoon and I have a premonition that I’m going to die that night, and it comes through clearly as can be. And it’s so irrefutable, like you said, I don’t even get scared by it. I’m just like, wow, that’s one of the cleanest hits I’ve ever gotten before. Like, okay, great. So Christmas Eve, I’m cooking dinner for the family and I’m just like, Oh, I don’t feel so good. I think I need to sit down and I start to walk over to the couch, and I realized I’m going to pass out. So to try to keep me from falling face first, I just dropped my knees, hit the ground pretty hard, and I’m shaking like crazy and come out of it. And I remember in a typical dude fashion, I’m unconscious. My hearing comes back first, and I hear my wife screaming to get the kids in the other room and saying: “I need to call an ambulance.” And I say something like: “No, no, it’s cool. It’s cool. I think I can walk.” So next thing I know, I wake up on the couch again, seated upright, and hearing comes back first once again. And I hear: “Sir, sir, are you there? You need to stay with us, sir. You need to stay with us, help on the way.” And I realized I’m talking to a 911 operator on speakerphone. And next thing I know, my wife’s not there because she’s answering the front door because now ambulances are in front of the house. And come to, and I’ve got a paramedic straddled over me, shaving my chest with a defibrillator next with me. And I’m like, fuck this. You know what? You’re touching him with this thing, and come back, and have total clarity, total peace. And it gets pretty real as far as the GFR moment when you get shuttled out onto a Santa’s magic sleigh on Christmas Eve in front of the whole neighborhood and spend Christmas in the ER. A quick update health wise, it turned out everything is fine. And I think it was just an emotional toll of the heaviness of everything going on and kind of like an ego death, if you will. And so it wasn’t like, that was like the aha moment for any of this next stuff. So much as just a culmination of a caring of a lot of burdens and griefs that weren’t mine.

Lisa Cherney: Wow. Wow. So part of you died, you’re super clear on that part. There’s something within you that dies.

Jay Rooke: That’s what I feel. Yeah.

Lisa Cherney: You say it wasn’t, you didn’t use these words to come to Jesus, but you know, it wasn’t that, and yet I imagine it was a turning point, of some sort.

Jay Rooke: So I think what it came to for me is, I love your distinction, it wasn’t like one of these, Oh, I had a heart attack and found God, and now I’m never going to do this job again, and I’m always going to do this or whatever that might be. I think that has already fallen. But what I think clicked in that night was, again, going back to the universe showing you the card over and over again was that there’s only one way through this. And so this emotional pain is going to stay present until I integrate and harmonize this entire part of my world, and stop keeping cerebral bright Jay, separate from corporate Jay, separate from vocational Jay, separate from dad, separate from healers, separate from intuitive on and on, and the need to harmonize all of those.

Lisa Cherney: I love that. They need to harmonize that. That’s beautiful. It’s even more beautiful than in immigration harmonize. And of course, it feels like it really creates a tonality that is unified in its outward expression. That is the next chapter for you.

Jay Rooke: Right. Yeah. A hundred percent, now that feels clear.

Lisa Cherney: And I just can not observe the timing of this at the end of last year. And we had met, we met in September of 2019, and I was telling somebody, I’m doing this cool thing today while I’m interviewing. And I said, we don’t not know each other. And we met at an event, and I don’t even think of any other conversation other than, Ooh, I feel you. You’re awesome. We need to do something. And that was like, it’s really, really funny. And so that was in September, this is in December, right? So now coming back around to where we are now, and there is no accident in you stepping into your full expression and navigating this current crazy time.

Jay Rooke: I know, right? You could, you script some of this stuff.

Lisa Cherney: You cannot make this shit up yet. I say, you make this stuff up, there’s just no way. All right, so in all forms that it ever will ever never resurface in your life ever again. And so give us the harmonized version.

Jay Rooke: Yeah. So I was working with a healer earlier this year, who I thought made a really insightful comment. She said: “Most people that are seeking evolution and ascension, and all of those types of things view it as rising up into higher levels.” And she said: “It’s not that it’s much more dropping away the lies and illusions of who we think we are until we can drop into our truest self.” And so what I’ve been really sitting with a lot lately, as I put the puzzle pieces back together and launch this next iteration is busy work versus being versus doing all that stuff and connecting the why’s behind each one. And so I’m trying to go through my whole world and eliminate all the non-essentials and trying to figure out where I’m most to show up, how I most like to show up and not tripping out of the gate anyhow on monetizing them. And I think what I had done historically, was like, Hey, let’s get a little bit of a seed of passion, or insight, or inspiration. And now let’s clamp this down with the legion campaign, and drip this, and what’s your blah, blah, blah. So really settling more into a natural expression of myself to your point around, Hey, everyone sees this anyways is just letting people access this part of me. So I think this has always been here, but, as I closed it off to people more so it wasn’t really available to be played with. And so starting to work into those waters. And then I think the biggest thing that’s been another huge component for me has been humor. And it’s been a big part of me my entire life through, but again, something that I kept separate from my work, it just never made sense to me. And I think you’re going to see from me a lot more of an integration of the humor into the work. And so there’s a Lakota Native American type tribal role called Heyoka, which is like a trickster and other cultures, or the Zen Monks have a version of this as well. And it’s essentially someone that acts as an amuse to playfully show you the things that you can’t see about yourself and where we’re off on our thinking and whatnot. And so, yeah, intuition is great, and doing deep personal work is great, and we can also accelerate how we get there and move in and out of that a lot more effectively when we’re laughing than when we’re guarded and trying to protect ego or get the story right. And it allows us to forgive ourselves so much more quickly than traditional ways. And so I don’t exactly have the answer for what this will look like yet, but I think you’re going to see more of what I’m working for.

Lisa Cherney: So tell us more about who you want to help going forward versus who you have been helping. I think that would be a good distinction. Or who they are, or maybe what they need versus then, versus now.

Jay Rooke: Yeah. Fair question. I was operating more on a businessy type of agenda prior, and while that’ll still remain true, I think the distinction is going to be that the folks that I most like to work with are pursuing entrepreneurship as part of their path of spiritual and personal fulfillment. It’s not like just a business job for them or another money-making opportunity like myself, excuse me, pursuing that restaurant back in the day, they need this in order to fulfill them and make that peace with themselves. So that’s the kind of arc. And then it’s usually somebody that realizes that they can’t get to where they want to be without some additional retooling or rearranging of how they operate. So how do we get that emotional intelligence, and the well-being, and that self-talk, and more of those spiritual sides of things, whatever’s one’s practices, whether it’s nomination or not just starting to learn how to use meditation? How to use breath? Work? How to pay attention to all these types of things to run their business. And for many of us, I think we’ve gone, we’re seeing this happen on so many levels in society right now, but we’ve swung so far into the sort of, I’m gonna call it more male MBA run a business like GE playbook that we’ve completely sterilized business. And so how do we reharmonize with that more feminine energy? How do we allow some of these different approaches to be as valid as business techniques, as doing a SWOT analysis, or trying to figure out whatever these metrics are that we can look at. And for most people that doesn’t feel good to them because they realize that they’re leaving some chunk of themselves on the table and operating out of inauthenticity with themselves. And so how do we start to weave all of those together to create happier people that are running healthier businesses that are more aligned with higher callings for themselves.

Lisa Cherney: Beautiful, so fricking needed. So needed.

Jay Rooke: I appreciate that. Yeah, it feels right.

Lisa Cherney: Especially from a male, I just have to say. I don’t know if you’re wanting to work with men, and I just could see such a profound contribution that you will have to men to hold that space for them.

Jay Rooke: You know, it’s interesting because, historically, my client load has been way more female than male, which makes sense to me. And now going into this period, I agree. I think we’re going to see a switch, and I appreciate the dialogue that society is currently having around toxic masculinity and rebalancing things. And yes, that all makes sense. And we don’t get there without starting to teach and practice what healthy masculinity looks like and not just assuming that that’s just a default given for how people know how to operate. And so, yeah, there’s a lot of rounds that I’d like to start to plan.

Lisa Cherney: Yes. And I can totally see just as you want to do for your clients, and help them heal along the way, and have their business be their spiritual practice. I can absolutely, from my GFR perspective, see how your healing is going to continue as you begin to be more authentic and come out even in a much bigger way, the congruency, and the self forgiveness and all these things, you’re seeing your journey as freaking perfect. It’s going to be so beautiful.

Jay Rooke: Yes. That resonates a lot and tends to your point, I think in this last year or so, I’ve started to be able to reprocess some of those memories or experiences and be like, Oh, that wasn’t meant to just crush my soul at the time or whatever it might be. That was allowing me to understand this part of humanity or to see this other person differently and then re-recognize those things in myself. As a coach, a lot of our work with clients and that is becoming work on ourselves as well.

Lisa Cherney: Yes. I’m super excited for you. Very, very excited for your new harmonized Jay.

Jay Rooke: Yeah. And the cool part is I’m starting to get a better discernment to what that energy feels like about just JB and Jay versus when I was like, maybe we call it a year or two ago, like, Hey, it’s time to like, suit up for lack of the correct term and be out there, and be this, and be more, be the next thing then it’s just not being necessary.

Lisa Cherney: Yeah. I mean, having thoughts of, I hope I will get fired, and maybe it just sucks for everybody. I mean, these were the thoughts of the younger versions of yourself and you probably can’t even imagine having those thoughts now.

Jay Rooke: Totally, right.

Lisa Cherney: Yeah, beautiful.

Jay Rooke: Thank you.

Lisa Cherney: So, Jay, I just feel like there’s going to be people that are listening that are going to be really leaning in and intrigued by this new version of your work, and that even though you don’t know exactly what it looks like, I think this will be good for you too. It was like, you don’t need to have the perfect offer, and the perfect branding and all that out there, but you’re already talking about your desire and how you want to help people. So would you be open to people reaching out to you if they like hearing what you’re saying? And they’re like, ah, I think I want to explore more with Jay.

Jay Rooke: I think it would be cool too. One of the things that I came to a big aha commitment about this year was that I am no longer going to try to go it alone all the time, which I knew was not a good way to go. But in the collaborative side of things, I’ve realized that I just want to work with people whose values I share, like yourself, the same way this whole thing clicked that I’m going to start to pay attention to those a lot more. And so I think there’s gonna be a lot of collaborative opportunities coming up, and I’ll throw out some things that I’m thinking about working on right now. And we’ll just see where it all goes. So right now, I’m about halfway through developing a personal development and well-being app that should be launched in a couple of months that I’m pretty excited about that’ll help people kinda keep on their own pace and follow their own practices to access their higher selves and be more happy and productive. Thinking about some type of a talk show type of thing, so I’ve got the podcast, but more of a fluid, almost Howard Stern style thing going on that’s much more comedy than commentary on society driven. As far as working with me one-on-one, I’ll be launching a community at some point soon. I’m not like you said, I’m not exactly sure what it looks like. Keep an eye out for that, that will likely be more of a Facebook type free one and then a more intimate mastermind community that’ll probably run for about a year, have three or four gatherings in person, monthly calls, that type of thing for the mastermind. And then on the one on one, probably the product or offering that I’m super excited about that I’m going to be launching now, I guess it’s called Jaywalking. I was chatting with a client of mine and he’s like, man, I get so much out of quick chats with you. It’s like Jaywalking where we make a shortcut and get something done. And so not only did I love the name of that, but what I realized is that my favorite thing to do is to go for a walk in nature, go for a walk through the vineyards when I’m doing my client work and a lot of my coaching calls. And so rather than keeping those two worlds separate, I’m folding the two together and going on a Jaywalk is my next offering. So it’s gonna be a 90 minute walk through nature. You can either do it with me or virtually, and we record the call and that’s meant for some of those one off issues that can get done in a session. So those would be the things for me. So jayrooke.com, J-A-Y-R-O-O-K-E.C-O-M is where folks can go. And you’ll see that there.

Lisa Cherney: That’s awesome. I’m so excited for you. It’s going to be so much fun. It’s going to be so much fun, and I think that you will no longer have that question of what’s wrong with me, that resurfaced over and over again in your story that this will feel so right and so congruent. So I’m super happy for you.

Jay Rooke: Thank you so much. I really appreciate that. Well, Lisa, on behalf of myself and all of our listeners, I want to thank you for providing this very wonderful facilitated conversation and interview. I really enjoy this. It’s always funny when you learn things about yourself on topics that have been, you know, we thought for a long, long time. So I really appreciate your insights today.

Lisa Cherney: It was my joy. It was really so fun.

Jay Rooke: Cool. Well, so folks that check out Lisa GFR Commandments. From my heart to yours, I want to say thank you very much for everyone who’s been part of the journey the whole way through, who supported me all along the way. And for those of you who have tuned in for the last hundred episodes, the inspiration for this podcast was that I realized that no one was having the real conversations about what entrepreneurship is actually like under the hood. And my goal has been to provide a platform and a forum for others to share their experiences and stories about what their entrepreneurial journeys have been like through an unfiltered eye and not always cleaned up. So I hope that that has served you along the way. I know it’s certainly served me, and that was the inspiration launch in the podcast, so I hope that’s been the case. I really look forward to the next hundred episodes and where all of this will go, and the brand continuing to evolve. And I look forward to having you in my journey throughout that process. So drop me a line, let me know how you’re doing. And I look forward to hearing from you on episode 101.

Thanks everybody, Jay Rooke’s here signing off, much love to all of you.


Leave a Comment

Scroll to Top