Cloud Nine Living with Jordan Gross 

October 1, 2019

LBL 140 | Cloud Nine Living


Many of us get so caught up in the everyday minutiae that we forget the things that matter, the things that are good, and the things that brings us the feeling of ecstasy towards cloud nine. Inspiring us to slow down and reflect on the cloud nine moments of our life is Jordan Gross, the owner of Cloud Nine Living. Jordan shares his insights from his upcoming book, The Journey to Cloud Nine, where he talks about the importance of having the sense of self-awareness and the ability to reevaluate scenarios and realize they are so much more meaningful. He also talks about making changes, being an optimist, and helping others find their cloud nine moments as well.


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Cloud Nine Living with Jordan Gross

Our guest is Jordan Gross. Jordan comes to us from New York City. He is the Owner of a company called Cloud Nine Living. We're going to get into it because for me to explain what Jordan does, we'll never do a great service. Jordan, welcome to the show and welcome to the West Coast.

How are you?

I am doing great.

It's great to be chatting finally. I know we connected a couple of times, but this is exciting to be on this show, share my story and share the Cloud Nine story. Maybe we'll even get a little bit of your story as well.

I bet you like I meet most of the people that are on my show is through LinkedIn because to me that's where the interesting people are. No offense to Facebook, no offense to Twitter, Snapchat or whatever. The business audience, the people that are the idea makers, the people that are creating the good content that are adding value and not just creating the needle but shaping it, are on LinkedIn. You and I met through a series of conversations. I went, “I've got to pick up a phone and I've got to talk to this guy.” What I want people to find out is Cloud Nine Living. The name itself brings certain ideas to the forefront. I'm going to let you tell your story because that's what this is all about. Tell me where Cloud Nine came from. What is the genesis of this movement?

Cloud Nine came from this amazing sequence of events. It was a perfect alignment of the stars in November of 2018. It was a normal football Sunday. I live in New York City. I was downtown at a buddy's apartment and we're doing typical guy stuff, yelling at the TV when our fantasy teams weren't doing well, slow-roasting a pork shoulder, talking about things that weren't so important. What made this Sunday a little bit different was that one of our acquaintances from high school had passed away. We started to bring it up toward the end of the day and our conversations went from nonsensical guy stuff to life, love, death, meaning and purpose. It was very introspective in a way that we'd never chatted before. As I'm going home that night, I'm driving in an Uber on the FDR in New York City and I see out in the East River a boat. The boat, the only thing I could see in letters on the boat was its name. The name of the boat was Cloud Nine. The Uber driver, the cashier, the waiter, the waitress, I always liked to spark conversation and get them a little bit outside of the norms of their day. I said, “What does Cloud Nine mean to you?”

His story shaped what the Cloud Nine Living movement is all about. He started to light up at the story of him having a family, him getting married, him moving to America, him making enough money to go back to his home country. He talked about a time when he was a kid that he remembers feeling on top of the world. As I'm listening to his stories, I started to think about my own. I'm thinking, “I've had these Cloud Nine moments as well. I've had these Cloud Nine experiences of uninterrupted joy.” I'm sure there are other people out there who've had them too. I started asking hundreds of people around the world from very high performers, billionaires to dancers, teachers and people in my own life, my family members, my 90-year-old grandma, “What does Cloud Nine mean to you? How are you living your version of a Cloud Nine life?”

You have the opportunity to evaluate scenarios in your life and realize that it's so much more meaningful than it is at the surface. Click To Tweet

As I hear all these stories, I started to realize that Cloud Nine, The Journey to Cloud Nine, which is the name of the book that'll be coming out, is what I'm doing. My life has been characterized by moves in which I was making a change but never went all in. I'd make a change and I wouldn't go all in. I'd always have some safety net behind me. A couple of years ago, I decided to quit my job in the corporate world. I wrote my first book and I help people for a living. That was my Cloud Nine moment. It was that one big change where I made the leap. My one word, my personal brand is being a trailblazer. I blazed a new trail for myself. That's what I do for other people is I'm trying to help them live their Cloud Nine lives by blazing this new trail on their own where they can make this one change in their lives and ultimately have the domino effect occur and everything else changes as well.

Most people don't realize when those pivotal moments happen in their lives. You realize that maybe a few years later, maybe several years later. Maybe at the end of your life you can look back, you can pivot and you can sit there and say, “That was the pivotal moment that changed my life.” When we're going through it, when we're making that messy change because normally it is a messy change, we don't realize how good things are. We don't have the appreciation of the change that’s happening in our lives.

When you're going through that change, there are a lot of things that are happening in your life. Whether it's going from being an employee to an entrepreneur, from this mindset to another mindset, people have to sit there, be able to stop, be in the moment and realize, “I'm making a conscious choice to go left instead of right.” My question is how do you get people to appreciate that? Many people are so caught up with the day-to-day minutia that goes on for most of us, myself included, that we don't step back, sit there and say, “That was a cool day.”

Let me tell you two stories. Number one is probably one of my favorite things that have ever happened to me in my life and it's because it was this chance encounter, this coincidence that occurred as I was writing The Journey to Cloud Nine. It shouldn't have happened because I never do this. I looked up the word ecstasy online because feeling like you're on Cloud Nine, it's this feeling of euphoria or this feeling of ecstasy. Once you go past all the drugs, I saw that the word ecstasy comes from the root word ecstasis. What ecstasis means is to literally take a step to the side of or to step outside of oneself. In thinking about what Cloud Nine means and how to better appreciate Cloud Nine moments, you legitimately have to be in this state of ecstasy. You need to take a step outside of yourself.

In the book, it's a fictional book so what I do is I put you in the clouds. You put yourself into the clouds and you look down at your life from this third-party perspective and you say, “That was a pretty good moment. That was a pretty good day. That's a pretty Cloud Nine life that I'm living.” I say it's one of my favorite coincidences because never in my life have I looked up the root of a word before. This one word that I looked up and I found that the root of it had this meaning, it was this crazy scenario that's like, “That's how you better appreciate your Cloud Nine moments.” It's by every single day having the sense of self-awareness to put yourself into the clouds, look down at whoever you are and say, “I had a Cloud Nine day. I could do this to have a better day. Here's what I need to have a Cloud Nine day tomorrow,” and have that sense of self-awareness.

Story number two is how I was able to understand that I can create a sense of my own epiphanies or Cloud Nine moments. It comes from listening to a ton of podcasts. I've immersed myself in this self-help and personal development world. I hear all these stories all the time about, “It was this scenario where I finally realized I had to make a change. It was this sickness where I realized I had to make a change or this accident where I realized I had to make a change.” Here I am saying, “Why would I ever wait for that?” I was listening to one of my mentors, Hal Elrod, who wrote The Miracle Morning. This guy has been through a lot. He has literally died. He has had cancer.

LBL 140 | Cloud Nine Living

The Miracle Morning: The Not-So-Obvious Secret Guaranteed to Transform Your Life (Before 8AM)

He has been fully broke. He was a troubled kid growing up. He was in detention all the time. As I'm listening to Hal’s story, a close mentor and friend of mine now, I said to myself, “Why would I ever wait for the perfect or imperfect alignment of the stars to take control of my life and start doing what I want and start appreciating what I currently have?” I always say that my a-ha moment was listening to Hal and realizing that I don't need an a-ha moment to have these a-ha moments. How back and forth and circular is that, but that's what it is. It's that in every single scenario in your life, you have the opportunity to evaluate it and realize that it's so much more meaningful than it is at the surface.

I want to unpack that a little bit. Life happens and it's going to continue to happen. There is no perfect moment for everything. There is no perfect in our world. The world is a continuum. Things are going to get better. They're going to get worse. We're going to be richer. We're going to be poorer. Our health is going to be better. Our health is going to be worse. There's no perfect time to start a business. I started Your Brand Marketing in January 2008. If there was the worst time to start a company, I can't think what it was but it's the right time in my head.

We all need to sit there and say, “If we're going to make a change, there's never going to be a perfect time to make that change.” If we want to lose weight and we want to start a new business. If we want to bring on a new employee, we just need to do it. Have a plan and stick by that plan. If that plan isn't working, evaluate why the plan isn't working, pivot and move forward. We need to sit there and have the ability to take a chance. I love that about you. We need all to make choices in our life to take chances for our own betterment.

It's about knowing yourself. It was the best time for you in your life. It's about calculating that risk. I'm a risk-seeking person. I was okay with quitting my job and not having something to do next. If you're risk-averse, make a more calculated exit from your job if that's what you're going to do. You mentioned this phrase of life is going to happen to us. You know the phrase everything happens for a reason. I don't fully believe in that. I think that everything happens and then it's up to us to assign a reason to it. This comes back to storytelling and how we assign the stories to whatever happens within our lives. That's what I believe is so important in every single scenario. It's like, “This happened. 2008 occurred. Here I am. What do I do?” I can view this now as an opportunity. This is when I'm going to start a business. That's the story that you decided to tell.

My view on life and this is a story I love to tell all the time is glasses are neither half-full nor half-empty, they're refillable. If you look at life as a refillable glass, even if you spill a little bit, even if you go back three steps, even if you go back ten steps, it doesn't define who you're going to be moving forward. We're all going to stumble. We're all going to have things in our lives that are going to reach out and give us a smack upside the back of the head. It's how we react. It's how we take the lessons learned from those events that happen in our lives and become better. Everybody has that capability.

Everybody has the capability of either saying, “I've got cancer. I'm going to crawl into a corner and I'm going to eat nachos the rest of my life and watch television.” They're going to sit there and say, “I've got cancer. What can I do? What can we do to move forward from this point? What can I do to make my life the best life that I can?” That's the difference between the optimist, the pessimist, the person that's going to succeed and the person who's going to sit there and wallow in their life. My question to you is as you were building the journey to Cloud Nine, as you were interviewing people, what were the biggest insights you were getting from people? Were there recurring themes that were coming up?

Before I get there, there’s one last thing on the optimist versus the pessimist. In my mind, even if the optimist doesn't make it through, at least that person will have done everything possible to have tried and given the best opportunity to make it through, whereas the pessimist won't even have given it a shot. That’s how I'd want it and that is that being an optimist gives you the opportunity no matter what the end result is at the end of the day. The themes that have come up have really been every single story has touched on one of these principles. It's shocking because you'd think that I would get different types of stories and I do. I get all different types of stories from people around the world. Some are the highest performers, billionaires, startup founders and bestselling authors. I talked to my mom and dad or normal people. I talk to my friends, normal people. Here are the themes.

There are seven key themes that have come up. There's an eighth theme that is bringing it all together. There's a ninth theme that allows you to start making a change in your life moving forward once you've realized that you can make Cloud Nine moments every day. At the end of the day, we have nine themes for our Cloud Nine journey. The first one is playfulness. The second one is camaraderie. The third one is love. The fourth one is responsibility. The fifth one is accomplishment. The sixth one is benevolence. The seventh is calling. Once you've had those seven themes, the other stories that I hear are that anytime this happens you have this Cloud Nine moment, there has to be the realization of the moment. That's the reflection piece. Finally, once you've had that realization of what your Cloud Nine life is supposed to look like, then it's your opportunity for resurgence. If you haven't been living your Cloud Nine life, you can redefine the way that you're going to live and then live according to it based off of everything that you've uncovered.

Everything happens; it's up to us to assign a reason to it. Click To Tweet

I look at those as key factors in leadership as well. The work that I do is all about trying to make better leaders within organizations and be able to use internal communication to engage, retain and grow employees. I look at those nine principles and I sit there and say, “This is about being human. These are all human qualities and the more we can be human both with ourselves and with the people around us, the more inspired and the more inspiring we can be.” There's a lot to be learned from that. People need to realize that the world that we live in is full of human beings. We all have goals. We all have aspirations. We all have things that we want in life. The more we can help the people around us, first of all, understand their Big Hairy Audacious Goal and help them live it, the better the world is going to be. It’s not just living your own Cloud Nine moment, it's helping others to live their moment as well. That's the world that I want to live in. That’s the world that I see as not only being inspired and living an inspired life, but helping others to feel inspired as well.

You said it best and with the whole metaphor of the book basically takes you on a plane through the clouds. You want to be somebody else's copilot. You want to copilot them throughout their journeys and you want to change the world, but you can't change the entire world all at once. If you change one person's world, you change another person's world, little by little you're changing all of these people's worlds and then ultimately the whole world changes.

It’s little pebbles in the water, they all create ripples. The more ripples we can create, the bigger the waves we can get. I can't solve the world's problems. I'm not president of the United States. I'm not head of the UN. I'm not Richard Branson or whoever. I don't have that reach and influence. What I can do is I can influence the people around me and I can help those people influence the people around them. If we can do that, we can start a wonderful chain reaction. Let's get into something I thought was interesting. You've done a TEDx Talk. Tell me about your experience. First of all, what was the TEDx Talk on? What brought you to a point, “I have to do a TEDx Talk?” What was the experience like? Where is the journey taking you?

I was able to get a TEDx Talk as somebody who was just starting up without a following, without anything except my first book that I wrote, which was called Getting Comfy: Your Morning Guide to Daily Happiness. It was a self-help book about morning routines.

How old were you when you wrote that book?

I was 22.

LBL 140 | Cloud Nine Living

Getting COMFY: Your Morning Guide to Daily Happiness

You were fairly young when you wrote a book. I didn't write a book until I was 48.

It came out when I was 23. I'll have the second book out when I'm 25. I gave the TEDx Talk when I was 24. The way that I was able to get a TEDx Talk with nothing to my name was through relationship-building. For everybody out there who's reading who thinks, “I can't give a TED Talk. I don't know anybody or I don't have a following or I don't have a platform.” It's totally possible if you have the ability to make an impact on one person and a group of people. The way that I got my talk was by reaching out to a number of TEDx organizers and hosts and by figuring out a way that I could add value to them and what they were doing. It ultimately ended up that I spoke at a middle school. It was TEDxClintonMiddleSchool. I spoke to a lovely woman named Sarah who set up the event. I basically told Sarah that middle school students are under so much pressure even at that young age.

My message was all about how to overcome that stress and anxiety right when the alarm clock goes off in the morning. With that, I was invited to give that talk. I went up to Upstate New York in Clinton, New York. It was a really cool TED event because it was an adult speaker and then middle school speaker. It was very refreshing to hear that their messages were all the same, it was the way we packed them up and delivered them were a little bit different. We learn the same things when we're ten as we do when we're 30. It's a matter of how we are going to internalize them best and utilize them in our lives that shape the way that we live. My TEDx was called Getting COMFY with the Uncomfy. It was my morning routine of how to beat that alarm clock and beat that stress and anxiety. It was also about how to get comfy in your own skin. It was also about how to then deliberately get outside of your comfort zone because that's always important for growth, and then the actual five-step acronym approach of how I feel a little bit more confident in situations where I'm outside of my comfort zone.


That's the most important thing, beyond what you spoke about, is that you found a need. They needed you. You had a message that spoke to their audience. You were able to provide them something that was valuable not only to them as organizers, but to the audience that they were trying to serve. It's enormous because too many people sit there and say, “I've got speech X. I speak a lot. I speak all over the place,” and people say, “What do you speak on?” I said, “Here are the general themes that I speak on. How can I make that speech personalized to your audience?” I have certain stories that I tell. I have certain themes that I talk about, certain ideas I talk about. If you listen to me speak ten different cities to ten different audiences, you may not recognize it as the same speech because I do everything I can to, first of all, make the audience feel that they're getting something of value to them. Also make the organizer feel they're the number one special people, that I'm making them look like heroes.

That's what you did, “How can I make these organizers of this TEDx look like heroes and add value to their audience and do that?” That's a good lesson for anybody. It's not about you, it's about the people you serve. That’s a lesson for life. That's a huge lesson and I'm sure it's a huge part of Cloud Nine Living. It's that servant lifestyle. It's not all about me. It's not, “Look at me, look how pretty I am. Look at clothes I'm wearing.” It's, “How I can make this world a better place?”

One of my favorite books is The Go-Giver, which is a short business parable about how giving is so important in business, in life and in receiving even. When you're giving, you're truly living. When you're taking, it's like you're just surviving. That’s what it's all about. It's all about how are we going to most add value to the world? I say that I try to help people with their life statements. One of mine is I add value to others without expecting anything in return even. It definitely resonates there.

You're 25 years old and you're living your Cloud Nine life. You're not even a quarter of the way through. The joke my wife told me on my 50th birthday was the fact that now I'm on the backside. I go, “I've got another 50 years to go.” My question to you is how do you keep inspired by the Cloud Nine life? How do you keep setting those goals to say, “What's next?” Where you're not always reaching for that brass ring, where you can appreciate when you actually do reach that brass ring, celebrate your accomplishment and then sit there and say, “I crossed this bridge. I climbed this mountain. I accomplished this goal. That was really cool. Let’s celebrate this. What's next?” How do you put that within yourself? How do you teach that to your clients?

When you're giving, you're truly living. When you're taking, it's like you're just surviving. Click To Tweet

I'll tell you a little story. It was probably the first time in several years that I lashed out. I impulsively yelled or cursed at somebody who was a cab driver in New York City. I’m a mild-mannered guy, even keel. I was walking across the street and I got honked. I had the walk sign, so I was clearly in the right, but the guy was honking at me and I cursed and I stood there until I couldn't stand there anymore. As he was honking at me, I walked past and I walked to the grocery store or wherever I was going. I said, “Why did I do that? What's wrong? What's going on here? Maybe he was going because he was in a rush or maybe there was an emergency.” I started feeling bad about why I had lashed out when I hadn't in such a long time.

I decided to ask one of my mentors about this. His name is Jeff Hoffman. He founded We had a conversation about being patient. For me, I'm at this stage in the game where I'm helping a lot of people and I believe in what I'm doing. I want to be this household name with Cloud Nine Living in the books that I write and the teachings that I make. I'm not there yet, but I'm on my way. I have to be patient. I said to Jeff, “How do I break the threshold from making an impact and doing some good stuff to making an impact, like being a Jeff Hoffman or something like that?”

He said to me, “Have you written down your ultimate goal?” I said, “Yeah, of course.” He said, “Have you written down what you're going to do the day before your ultimate goal?” I said, “What do you mean?” He said, “Have you written down what you're going to do the month before your ultimate goal?” I said, “What do you mean?” He said, “How about the year before? How about the year before that? How about the year and five months before that?” He's telling me this and he says, “When I set my goals and I started or I started my record label, I literally projected five, ten years into the future. I envisioned who I was going to be at that time in my life and then I worked my way backward.” Reverse-engineering your goals, but he was telling it to me in a creative way.

I started to think, “This is a great way to remain patient,” because I'm going to have so many opportunities to celebrate where I'm at along the way by setting these micro-goals moving toward the ultimate goal at the end of the day. That was a great way for me to say like, “It's all about being patient, playing the long game and having this set plan, working that plan and then seeing if maybe I don't hit that plan on a certain day, how do I change things up a little bit?” I'm working toward the plan and it's going pretty well. I can do all I can do every single day, be reflective of that day at the end of my day and ultimately try to change things around the next day so I'm doing a little bit better than I was before.

Let me ask you one last question. This is a question I ask everybody as they walk out the door. When you leave a meeting, you get off the stage or you leave somebody for whatever reason. When you get in your car and you drive away or your Uber, what's the one thing you want people to think about you when you're not in the room?

“That Jordan Gross man is a nice, authentic human being.” That's all I want in life. It's that simple. If that's what people say about me when I'm not there, then I'm okay with that.

I'd love to have that on my tombstone. That sounds like a wonderful thing to have. Jordan, thank you very much for a great talk. I loved having you on the show. Thanks for the inspiration. Thanks for being a great guest.

Thank you, Ben. This was a lot of fun. I enjoyed it. Thanks so much.


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About Jordan Gross

LBL 140 | Cloud Nine LivingJordan Gross IS a Northwestern and Kellogg School of Management graduate, a writer, a leadership coach, a speaker, and a self-proclaimed multipotentialite, having experienced positions in large banks like Merrill Lynch to small startup companies like Chowbus, focused on bringing cheaper Asian delivery food to urban populations. He is a corporate refugee turned trailblazer for positive change, optimism, and the belief that our daily actions can help us all overcome stress and anxiety.

Also a best-selling author of a book called Getting COMFY: Your Morning Guide to Daily Happiness, a TEDx Speaker, and have founded multiple companies and organizations!

In his free time you can find me listening to podcasts, at the gym, playing sports, reading Mitch Albom books, writing Mitch Albom type books, and living his own version of a Cloud Nine life!

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