The Power of Sharing Stories

One of the things we’re trying to do with the GetCoached360 podcast is to share the stories of successful people. We are hoping to reach aspiring entrepreneurs so that you may take away the valuable lessons from these stories. These are stories of how ordinary people were able to overcome hardships. With the mindset they had and the steps they took, they came out of the other end transformed and extraordinary. 

However, to be a good storyteller requires personal development. You need to be able to look past the pain and, instead, look for the wisdom in the situation and leverage it. 

We face many challenges in life. It is one thing we cannot change, but there are two ways that you can perceive it. Some people see challenges as blockages. They fail to grow and learn from them. But, for others, they view them as signals to steer them in a more positive direction and a chance to grow. 

We are hoping to share stories that make you want to do something about your current situation—actionable advice.

And so we understand the significance of compelling storytelling in helping people make the right decisions. This is why I took the time to sit down with Jordan Gross, an author, TEDx speaker, and entrepreneur. He coaches people on how to uncover their Cloud Nine life. In this episode, Jordan and I discuss the value of storytelling and how it is an excellent skill for any entrepreneur to learn.


Episode Summary

  • Courageously pursue a path that gives you a sense of purpose.
  • There are lessons in every situation. Whether you see it as positive or negative, what is essential is being able to learn from them and act on them.
  • It is in failures that you excel. You’re not meant to succeed in everything you do, but you have got to keep going.
  • Be in the present and more aware of what is happening around you. Life will often put up signs or signals in front of you to steer you in the right, more positive direction.
  • Live and learn from life so much so that people can use your experience to make the right decisions and follow a unique path that is their own.


Covered in This Episode

Early Life and Background

[03:44] Following a path dictated for me

[06:26] Desire to make an imprint in society

[08:55] Choosing a job for the wrong reasons

[12:04] Going back to starting something and watching it grow

[13:36] Path to live more of the cloud nine life


[17:35] Everything happens for a positive reason

[20:24] Awareness when things are a little bit different

[24:20] Learning is learning

4 Key Lessons from Being a Goalkeeper

[26:51] Enrich the meaning of things

[28:20] Be somebody who far surpasses expectations

[29:33] Persistence in putting your best foot forward

[34:24] Dive head first into entrepreneurial pursuits

[36:57] Allowing Autonomy Through Storytelling

[43:14] A Storyteller’s Journey

[48:27] Write for Yourself and Others/Be Your Own Superhero

[50:49] How to Contact Jordan Gross



Getting Comfy: Your Morning Guide to Daily Happiness

Journey to Cloud Nine

Start With Why

How to Win Friends and Influence People

Stories that Stick


Guest Information

Website: https://www.journeytocloudnine.com/

Instagram: https://www.instagram.com/getting_comfy/

LinkedIn: https://www.linkedin.com/in/jordan-gross-8271905b/

Medium: https://medium.com/@jordan.c.gross2016

Episode Transcript

Chris Ippolito 0:56 

Hi, Jordan. 


Jordan Gross 0:57 

Hey. What’s going on, Chris? How are you? 


Chris Ippolito 0:59 

I’m doing great. How are you? 


Jordan Gross 1:00 

Doing well, doing very well. It’s an exciting Saturday morning, April 11th, 2020, in the midst of something unprecedented. When your listeners five years in the future look back and they’re listening to this episode, we are in our homes, quarantined for, I don’t know about you, three to five weeks now at this point. 


Chris Ippolito 1:23 

Yeah, about that. 


Jordan Gross 1:24 

I’m just grateful to be chatting with you. Obviously we have the opportunity to connect and share a conversation like this. Thank you so much for allowing me the opportunity to chat and I’m just really excited to share a little bit about storytelling with your listeners, because we are in quite the story now. Maybe as we project into the future and think back to the times we’re in right now, we can tell this story of how we got through it as a family, as a friend group, as a society. I’m just excited to be here with you, man, and I appreciate you. 


Chris Ippolito 1:58 

Yeah, thank you. Welcome to the “Get Coached Podcast.” You’re right, we are definitely in interesting times. Hence, if you’re watching on YouTube, you’ll see that Jordan has got a face mask currently under his chin. But yeah, obviously this format, the podcasting format, it’s great because it hasn’t really stopped me, or us who like podcasts and do podcasts, to be able to continue doing it. Which maybe that’s going to be another catalyst to growing the podcast community, as it’s already been growing. 


But yeah, as you mention, we’re going to be eventually talking about storytelling, but I always love to start off every episode with having my guest share their story as far as where have you been, where did you start, and what’s that journey looked like to ultimately bring you to where you’re at today and what you’re doing today. 


Jordan Gross 3:01 

Absolutely. You mention the mask, and where I’ve been is New York City. For the last couple of weeks I was in my apartment for, I don’t know, two or three weeks just trying to self-quarantine as best as possible. Then now I’m at home on Long Island in New York where my family is. That’s why I have the mask, I’m still being cautious. Actually, I’m in my brother’s room right now, my dad is using my room as his office because he’s working from home. We’re just in a chaotic time, but we’re all figuring it out. But that’s the explanation of the mask and where I’ve been literally in the last couple of weeks. 


Now about my story. Like I said, growing up on Long Island, I was a kid who was just going through the motions. I was on the hamster wheel of life as somebody who was following a path that was dictated for me. What I mean by that was that when I look back and I think about my childhood, my preteen years, and my teenage years, I don’t even remember having a sense of individuality. I was an athlete, I played soccer five, six days a week. I was a goalie, I did five days of team practice, one day of goalie training. 


Chris Ippolito 4:31 

I was a keeper, too, actually. 


Jordan Gross 4:32 

Oh, yeah? 


Chris Ippolito 4:33 

Yeah. We’ll have to chat about that. 


Jordan Gross 4:35 

Yeah, that would be great. There I was, I was this goalie really trying to make it big. I was trying to mix academics with athletics to get into the best college possible, that was the path that I was supposed to go on. I did my schoolwork, I did my homework, I studied hard for my tests, I trained hard for my sports, and I was “successful.” I put that in quotes, if you’re just listening to this. Because I finished toward the top of my class academically, I was getting pretty highly recruited for soccer. The next step on this hamster wheel, ladder, or whatever you want to call it was to get into a good college, play soccer, and try to continue on this route. But when I realized that soccer wasn’t going to be a professional endeavor for me, it was, “Okay, what’s next on the hamster wheel?” 


I had teammates, my brother is a couple years older, his friends were guys who were similar to me personality-wise, I had fraternity brothers who just said, “Okay, what you do now is you study finance, economics, and business. You get internships, you get a good job, you go make a lot of money, and you have a good life.” Again, looking back, I was just following orders, I was just doing what I thought I was supposed to be doing. I was never really thinking for myself, I was never thinking about my own fulfillment, my own happiness, embracing any purpose or sense of what I wanted at all. 


I was just, again, following in the path of what other people told me to do. I was getting good internships in finance and consulting, and I started to have a little bit of a differentiation from what everyone was telling me. I knew I didn’t want to go into these things, but I still didn’t know exactly what I wanted to do. It wasn’t until I got back from studying abroad in Prague my junior year that I came back and I said, “Okay, let me really try to make an imprint on society, let me try to start something.” 


I started this Alzheimer’s awareness organization in honor of my grandfather at Northwestern where I was going to school. I loved it, I loved starting something from the ground up, I loved building something based off of relationships, I loved adding value to other people and the journeys that they were going on, I loved helping. That was an experience that I look back and I think was pretty transformative. 


But anyway, even with that experience, I was still going through the motions. I didn’t know exactly what I wanted to do, people told me, “Why don’t you get a master’s degree or continue your education? You like school, right?” I was like, “Yeah, sure, school is fine.” I went and I got a master’s degree in management studies so that I could be a better leader of this Alzheimer’s organization. 


This was the year where I was in a program academically that wasn’t super rigorous. I had a lot of free time for the first time, because in college I was a little bit of a partier, I just spent most of my time with friends doing social activities as opposed to trying to really make a mark on helping people. I decided to change gears a little bit and I spent time in the entrepreneurial community, I spent time volunteering, I spent time really trying to understand what I wanted to do while I was doing this master’s program. 


I started reading a lot, I started listening to personal development podcasts and listening to audiobooks. I kept hearing, “Follow your passion. What’s your passion? What’s that going to be?” I thought mine was in the food and restaurant industry. I know a total 180, but I was trying to create this story of here’s a kid who was following the traditional path, finance, consulting, and all this stuff, then all of a sudden goes into the restaurant world. I was going to tell this story where I would look back and say, “I started as a 22-year-old kid and there I was, by age 35 I had my own restaurants all over the world,” and I would just work my way up and be a restaurant owner. 


But what happened was I fell into this opportunity where I did this rotational leadership program with a big restaurant group. I thought that was it, I thought this was going to be what I did day in and day out. But very quickly I realized that I chose that job for the wrong reasons, for the traditional reasons. Those reasons were more aligned with finances, the prestige, the highlight of being a 23-year-old leader at this organization where some people were three times my age but I was their boss, and I thought that was cool at the time. I was told that my position was like the Goldman Sachs of the restaurant industry. Even though I wasn’t doing the banking world and actually working at Goldman Sachs, here I was on my own journey at the peak of where I could have been in this new world. I just thought that was really cool. But I learned really quickly that that wasn’t what I wanted to do. 


About four months in I just finished up a 15-hour day and I was actually in the restaurant, I was the manager for the day learning what that was all about, with client engagement, managing a team of servers, managing the chefs, and things like that. I was doing my end-of-the-day paperwork and it was like, honestly, 4:00 or 5:00 in the morning, I don’t even remember. I’m in my nice suit and tie. I just had to go into the meat freezer to do the end-of-day inventory count, it was the last thing I had to do. I had to go in there, then come back to my office and plug in the numbers on an Excel sheet, send it out to the company-wide e-mail so that everything was good to go. 


I come out of the meat closet, I’ve got my gloves on, I walk over to the office, and the door is locked. At that point it was the only place I needed to be. I tried to finagle with the door, but I don’t know how to pick a lock, I couldn’t get in. People were going to show up for their morning shifts in like an hour anyway, it’s not like I would have stayed there and done nothing. But I couldn’t get into the office. 


I just sat on the floor and I thought. I thought, “What am I doing here? What am I really trying to get out of this experience?” I thought about the value I was adding to people and I considered where I was, sitting on the floor about to plug in meat numbers into a spreadsheet, just having typed up guest complaints that their signature cocktails were rung up wrong by the server so their taste buds didn’t feel right. It was just ridiculous, things that were so ridiculous to think in that moment. 


I was in New York City on Park Avenue in a very upscale restaurant for people like who I didn’t want to be, for business people, for investment bankers, for consultants. I always say that I was feeding the rich when I think that I’m supposed to be feeding the poor, I think I’m supposed to be helping people who maybe can’t afford these types of experiences. 


That was really all I needed, I needed that door to be locked for me to say, “There’s a reason why this door is locked and it’s because I should never go back into that office, I should never type in these excuses, I should never type in this meat inventory anymore, it’s not what I’m supposed to be doing.” I quit the next day and I thought about what I enjoyed from my experience in this restaurant world, the four months in it, and what I enjoyed from all of my experiences. It always came back to really starting something and watching it grow, it came back to adding value to other people, and it came back to building relationships, communicating with people, and seeing where it takes me. 


With those three things in mind, I thought, “How do I share that message?” I wrote my first book. I self-published the first book two months later and it was about positivity, optimism, communication, happiness, and fulfillment. It was a morning routine, that was the specifics of it, but it was really how this routine helps overcome stress and anxiety. I used anecdotes, I listened to people’s stories, I told my own story, and I got immersed in this world of personal development. I started coaching, I started writing more, I started doing speaking engagements, I started going on podcasts. 


I did that for about a year until I came to this next crossroads of, “Do I double down on this concept? Do I go back and get a real job?” 


Chris Ippolito 13:33 

“Real job.” 


Jordan Gross 13:34 

Yeah, a real job. 


Chris Ippolito 13:35 

Quotation marks, right? 


Jordan Gross 13:36 

“Do I write a new book?” It came back to another story, another pivotal moment in my life that I’ll always remember. I was riding in an Uber in New York City on the FDR, right by the East River, and I saw a boat in the East River called Cloud Nine. I asked my Uber drive what “cloud nine” meant to him and he told me stories that I’ll never forget. He told me about the time that his child was born, the time that he got married, or this moment of uninterrupted playfulness when he was a kid. When I heard those stories, I said, “Okay, there must be other people who’ve had cloud nine moments, as well.” I start asking people about their cloud nine stories and how they live a cloud nine life. 


Then, after I gathered all this information, I started to realize key patterns and themes with these cloud nine types of occasions. I said, “For what I want to do in my life, do I want to just come out with another book that says, ‘Okay, here are some stories and this is what you have to do in order to live a cloud nine life,’ or can I creatively tell these stories in a more fun, more entertaining, more original, and unique way?” I chose the ladder. I chose that because I think that in the personal development world there are a couple different ways to share information. You could have this qualitative, interview style approach where you share anecdotes, you could have the science-based approach, you could have the quantitative numbers approach where you do research studies. But I think there’s a little gap for fiction, for creative storytelling, for entertainment in the personal development world. 


That’s what I decided to do, I wrote a fictional story about how you can live a cloud nine life. It’s a representation a little bit of my own story where somebody follows the traditional path, they go the normal route, and they regret a lot of the decisions the made. But what I also show in the book is the path in which you go based off of your heart, your intuition, and you live more of the cloud nine life. 


I think the key theme here in this long-winded personal story is that the moments in my life that I remember most, the Uber drive, the meat freezer, starting the Alzheimer’s awareness organization, they have the most depth, they have the most creativity to them, they have the most opportunity for me to share and dive deep into the story, the moment, whatever it was that I was doing at that time. 


That’s why I love storytelling so much. It’s such a way for me to share with others not only my own thoughts, opinions, and lessons that I want to tell, but I can do it in a way that’s not just, “Here’s what you have to do.” It’s, “Here’s what I have done, here’s what others have done,” that are really opportunities for others to reflect and implement into their own lives as opposed to just go ahead and follow advice aimlessly. 


That’s where we’re at. 


Chris Ippolito 16:57 

That’s awesome. What was the title of the first book? I don’t know if you mentioned it. 


Jordan Gross 17:00 

It’s called Getting Comfy: Your Morning Guide to Daily Happiness, and the second book is called The Journey to Cloud Nine. 


Chris Ippolito 17:06 

Nice. It’s super interesting there, there were a few parts as far as your personal journey where, whether it’s God, the universe, whatever you believe in, it’s almost like they or it was trying to nudge you along a bit of a different path. 


Jordan Gross 17:28 

Yeah, that’s right. You know what? You know the phrase, “Everything happens for a reason,” right? 


Chris Ippolito 17:33 



Jordan Gross 17:35 

I believe that, but I always like to spin things around a little bit. I believe that everything happens. Everything is going to happen. Then you get to assign the reason to it. When you’re assigning a reason, why not assign a reason that is a story which is positive, which allows for hope, which allows for faith, which allows for this ability to push forward and enjoy every part of the process? 


Like you said, there were these maybe divine intervention moments, but it’s because I assigned divine intervention to those experiences. It could have been I got locked out of the office, then I sat there and cried because I was not going to get in our numbers on time, I was going to get in trouble, then the next day I was just going to say, “You know what? I’ve got to be better.” That’s the story I could have told, that’s the meaning I could have assigned to that experience. But I decided to tell a different story. 


Chris Ippolito 18:44 

Yeah, I agree. I believe that in a lot of cases what it is is the door locking, what that situation could have been, I mean whether you believe this or not, is that you subconsciously did that to yourself so that it would prevent you. It’s almost like your subconscious was trying to give you an indication or a sign of, “Hey, you’re not really that happy here, I’m going to start throwing some obstacles in your way. Hopefully you’re going to pick up on those signals and realize that deep down inside we don’t want to be doing this.” 


It’s the same with the Uber driver. Something catches your attention and subconsciously something like that really grabbed a hold of you. Now consciously you went and asked the Uber driver, he shares a story. Same thing now. Like you could have just accepted that as, “Oh, those were great stories. I had a great drive with this Ube driver, I’m going to give him a five-star review.” Life goes on. But, again, I’m a firm believer that your subconscious is trying to make you understand things and puts these signals in front of you so that hopefully consciously you’re going to be aware of them. 


I think that’s the value behind meditation or concentrated thinking, just sitting there and thinking. You’re starting to almost bridge the gap between the subconscious and the conscious. But that’s my woo-woo belief. 


Jordan Gross 20:24 

Yeah, it’s woo-woo, it’s whatever, but for me it’s about awareness. It’s about awareness when things are a little bit different. Because I can expand on the Uber driver story. This was in November of 2018. It was a normal Sunday where I went down to the lower part of Manhattan to a buddy’s apartment. We’re doing our thing, we’re cursing at the TV because our fantasy players weren’t doing well in football, and we slow roasted a pork shoulder. We were at first just talking about real guy stuff, but then something got brought up where one of our acquaintances from high school passed away. We all started talking about it and there was this moment of silence where we were just all pretty deep in thought, we could tell we were deep in thought. 


We started talking about life, death, purpose, fulfillment, and just stuff we never talked about as a friend group because we’re more happy-go-lucky, try to make each other laugh at all times kind of guys. When we got deep, that was my subconscious saying, “Okay, something is different about today.” It’s that hyperawareness of “this is different than normal.” 


With that same theme of “this is different than normal,” I went into the Uber driver’s car and something was different than normal. I sat in the back seat and I was silent. Usually, Chris, I’m the guy who is always trying to make somebody’s day more human, especially if they’re an Uber driver who drives people around and they probably don’t have a lot of conversation, especially the cashier who just robotically goes through and never really has conversation with humans. Usually I’d be asking a million questions to the Uber driver, but I didn’t at first. I sat in the back and I wanted to continue reflecting on the conversation from the day. But when I saw that boat, again, it was this sense of hyperawareness where I just said, “Okay, now I’m supposed to go back to my normal self. I’m not supposed to sit here in silence, I’m supposed to change this person’s day, I’m supposed to think about the other person in the car as opposed to just me who wants to be quiet.” 


I saw the boat and I asked him a question, it was probably the first word I said to him other than, “Hi, how are you?” That was when I learned, yes, I should have been chatting with him, and I’m glad I did because obviously I gained so much from it. 


Chris Ippolito 23:05 

Yeah. I think those moments are special in the sense of being aware of the fact that it’s breaking you out of your normalcy and to sometimes enjoy that. Sometimes it’s going to actually be a negative experience. I like to read stoic philosophy books. 


Jordan Gross 23:36 

Yeah, I love stoicism. 


Chris Ippolito 23:39 

A lot of that teaches the fact that there’s almost lessons in everything, whether it’s positive or negative. In a lot of cases, especially the negative, have a lot of lessons to share with you. But it’s about being able to almost take a step back, observe, and ask the question of, “Why?,” or, “What am I supposed to take from this?” Yeah, I think that’s super important. I think the more common advice is to slow down and smell the roses. But yeah, that’s really cool. 


Jordan Gross 24:20 

Yeah. I love that stoicism piece and just learning. Especially with where we are right now with the coronavirus, I’ve been doing a lot of research into uncertainty. When we don’t know what’s next, when we’re in unprecedented times, what most people do is they interpret it as good or bad. But my saying, it comes from the sports world and I wish I would have thought like this as a kid, but it’s probably too hard because all you want to do is win. But now I think what I would try to demonstrate maybe when I’m a coach of my kids is, I’ve got this new saying, “If I win, I win. If I lose, I lose. But no matter what I learn, I learn.” 


It’s that last piece where no matter what happens in the situation, whether it is playing a sporting event or whether it is handling such an extreme scenario as is self-quarantining due to disease, you don’t know if you’re going to win or lose, whatever you define as winning or losing in the scenario, but you are going to learn. You’re going to learn a lot about yourself, the people around you, society. Again, when I tell stories, it’s always projecting into the future and looking back at the story that I want to tell. Projecting into the future, looking back on this occasion where we are right now, I want to say that I learned. I learned about X, Y, Z. That’s always where I’m coming from when I’m sharing these stories. 


Chris Ippolito 25:55 

Yeah, I completely agree. It’s perception. Good, bad, it’s whatever you decide it to be at the end of the day. 


I wanted to chat actually about our similar career of being goalkeepers in soccer. Because anybody who has played sports, especially team sports, where there’s a keeper of some sort, whether it’s hockey or soccer, you realize real quick it takes a different kind of person to want to be a goalkeeper, especially in soccer. What would be some of the lessons learned from that career of being a keeper that you sometimes apply to life in general, or the way it evolved you as far as being the person you are? 


Jordan Gross 26:51 

Yeah. I’ll share three key lessons here. The first one is that I love symbolism, I love really enriching the meaning of things. When you think about the word “goalkeeper” in and of itself, I didn’t realize this growing up as an actual keeper. But when I look back, when you’re a goalkeeper, you’re the person in charge of the team’s overall goal. The team’s overall goal is to win the game. You are the keeper of that goal. Because if you don’t achieve the goal, then the ball is going into the net and you’re not keeping in the way that you should. 


Especially now, I am very goal-oriented. I am still a goalkeeper, I keep these goals and I try to adhere to them as best as possible. But, like I said before, “If I win, I win. If I lose, I lose. No matter what I learn, I learn.” That’s my mentality with goalkeeping now and I wish it was when I was a goalie. Because I was pretty emotional as a kid. If I let in a goal, I remembered every single bit of that experience leading up to the goal. But now it’s like, “Okay, what can I learn from letting up this goal, or not achieving this goal, or achieving this goal?” That’s definitely lesson number one. 


Number two is about being the underdog. This ties into number three, as well. I’m 5’9″, I’m not a tall guy. 


Chris Ippolito 28:30 

You’re only 5’9″ and you were a keeper? 


Jordan Gross 28:32 

Yeah, I was a 5’9″ goalie. It was about being an underdog, being in a position where I’m not supposed to be in, then performing way surpassing anybody’s expectations through hard work and dedication to the craft. 


What I equate that to now is that here I am as a writer, speaker, and a coach. I studied business in school, I studied economics, finance, and I didn’t write an essay from my senior year of high school all the way until after my master’s program when I wrote my first book. I don’t have training in this, nobody expects any excellence of me in the world that I am. Here I am as an underdog, just like I was as a goalie, to really shine, to outperform expectations, and to be somebody who is far surpassing what anybody would expect. That’s lesson number two. 


Lesson number three has to do with penalty kicks. Penalty kicks were my favorite, favorite, favorite thing to do as a goalie. 


Chris Ippolito 29:41 

Me too. 


Jordan Gross 29:42 

Yeah. Because just like lesson number two, there’s an expectation with penalty kicks in which you’re not supposed to save the ball. They’re 10 feet away, I don’t know, 12 feet away. 


Chris Ippolito 29:58 



Jordan Gross 29:59 

Yeah. They’re 12 feet away. 


Chris Ippolito 30:00 

Yards, 12 yards. 


Jordan Gross 30:01 

12 yards away from you and you’ve got this big goal. They could put the ball anywhere. How are you supposed to react to where the ball is going? They’re supposed to make it. When you make a save, when you actually do, not your job, but you far surpass what you’re expected to do in that moment, you’re the hero. 


I think, again, the lesson for me now is, just like I’m in that penalty kick shoot-out, nobody expects anything of this new up-and-coming storyteller in the personal development world. Here I am, I’m totally new, I don’t have any credibility, so to speak, but little by little I’m making saves. They’re coming up to the penalty mark, they’re shooting, and I’m guessing right. I’m coming out with a new book, I am getting on another podcast, and nobody expects anything of me. But I’m just here continuing to perform, continuing to shine as best as possible. Those penalty kicks, I think about them all the time because it’s that moment when nobody thinks you’re going to succeed that you put your best foot forward and you make the save. 


Just to wrap up, especially where we are currently with coronavirus, it’s like nobody expects you to thrive in this time. Everybody is taking a back seat. Which is fine, by the way. With something as unprecedented as this, with so much uncertainty, you’re allowed to feel however you want to feel. But the one thing people don’t expect from others is for them to really embrace this situation and turn it into the best experience of their life. But I think for me I can do that, I can focus on my health, fitness, and do workouts within my house that make me feel better than I’ve ever felt. I can cook all my own food and feel better than I’ve ever felt. I can write thousands of words a day, then edit them the next day, and write better than I’ve ever written in the best. I can focus all my attention on my coaching clients for the hour or two hours a day that I speak to them. 


For me, it’s just like those penalty kicks, when nobody is expecting you to excel right now, but that’s exactly what I’m trying to do and I’m trying to share with other people. 


Chris Ippolito 32:46 

Yeah. I would add to that. Not only is it the expectations are against you, but, similar to what baseball players say when it comes to batting, same idea, you’re not expected to hit all the pitches. But it’s in those failures almost that you excel. It just talks more about it in general, in the broad sense. You’re not meant to succeed in everything you do, but you’ve got to keep trying, you’ve got to keep going, you’ve got to persist. Because sometimes it’s this train wreck of failures which will ultimately lead to one success, but that one success is what sets the tone for complete and holistic life success. 


But yeah, I loved shoot-outs because it was usually that one save out of all the shots that would end up being the difference between your team winning or losing. I loved the pressure of it, I loved the responsibility of that being on me as a goalkeeper. Those were a lot of the things that I enjoyed about being a goalkeeper, and/or putting my body in harm’s way to be able to do something that would help the team out. That’s the way you have to think as a keeper, it’s crazy. 


Jordan Gross 34:24 

Yeah, that’s a big one. No fear, it’s the “no fear” mindset. This is lesson number four. Just like you’re doing, we’re going on these entrepreneurial pursuits. There has to be no fear, you have to literally dive head first into every situation. You could dive at somebody’s cleat in order to have a positive result for your team, for your clients. You are the one who’s leading by example, you’re going into every situation with that opportunity to really save the day. That’s what it’s all about. 


Chris Ippolito 35:12 

Yeah, it’s a little bit of faith and confidence, as well. Tying it to entrepreneurial journeys, nobody starts their business thinking it’s going to fail. There is that in the back of your mind, like statistically that’s what happens. But an entrepreneur and most people that endeavor on business, they have that confidence and that faith. They could even lack the confidence, to be honest. But they have faith, “If I stick to this, I learn what I need to learn, and I keep doing it long enough, the results will eventually come.” Then perhaps now the confidence starts coming in once the positives start piling up. But as a keeper, you have faith in yourself and your abilities, or at least that’s the way I thought about it. It’s like, “Yeah, I believe we can win this game, I believe I can make that save, I believe that I can do that.” But you don’t know until you try it, then sometimes you don’t. But if you don’t go in with at least having the faith of it, then success is almost guaranteed not to happen. 


Jordan Gross 36:29 

Yeah, that’s right. 


Chris Ippolito 36:31 

We’ve covered a lot. The unique thing about our conversation is, though we wanted to talk about storytelling, and we will, everything we did up to this point was storytelling. Why is that such an important skill set for entrepreneurs to develop, learn, and try and get better at? Why would you say an entrepreneur should learn that skill set? 


Jordan Gross 36:57 

Yeah. There are a lot of reasons I can just share, but let me share an example, one of the oldest tricks in the book. Think about children’s books for a second, or think about how we are able to get children to behave the way that we want them to behave. Obviously every child is different, but if you tell a child, “Don’t go into the living room because your shoes are dirty and you don’t want to break anything in the living room,” they’re probably going to, first thing, go into the living room. How do we tell them not to go into the living room? We tell them that the living room floor is like lava and if you go onto the living room floor, you’re going to burn your feet because of the lava on the floor. Or we tell them that there are scary monsters in the living room and if you go into the living room, then these monsters are going to grab you and you’re never going to be able to leave. 


Think about children’s books. Think about the story of Cinderella or think about the story if Snow White. What are we trying to share? We’re trying to share how we want people to behave in the world, but we do it through stories. Because the stigma is that we don’t like directly being told what to do, I think that’s because we want to learn and figure things out on our own. When we share stories as entrepreneurs, we’re allowing our customers and our clients to figure out for themselves why they should be using our products, why they should be using our services. There’s a lot more power to that than sharing features, than sharing success. But success stories are great. 


Very specifically in the entrepreneurial world I always think about these heart-wrenching Apple, Google, or Facebook commercials. Facebook just came out with a coronavirus commercial and the person is singing, yet also telling a song, you can’t really tell if they’re singing or not. But it’s just photos of different moments from the fight against coronavirus. At the end, it could be a commercial for anything, you realize that it’s Facebook. 


They’re not saying, “We are a company that you put pictures of yourself up on, you can create events on our platform, and our new features allow you to get the news and have high-quality photos on there.” But what they’re saying is that Facebook, through these pictures and the story that they’re sharing, is that Facebook is an opportunity for communities to overcome adversity, to inspire hope. That’s the message that they’re ultimately sending along at the end of the day. What that is saying is that, as a consumer, you’re more likely to use Facebook because Facebook is sharing the story of how the work that they’re doing is affecting others as opposed to just telling you the what. They’re telling you the why as opposed to the what. 


That’s the beauty of storytelling. You’re keying in on, obviously, people’s emotions. But even more so than that, once you hit on emotions, you’re allowing people to make decisions that feel like their own. When people make decisions that feel like their own, there’s a lot more power to that because then it’s a win for them. That’s what I think is the key ingredient, it’s that you’re giving them a sense of individuality even though the stories you’re telling are not specifically about them. 


Chris Ippolito 41:01 

Yeah. I really like that explanation because what it ended up making me think of was two different books that are very valuable books for most entrepreneurs, they’ve come up quite a few times in the podcast. Start with Why by Simon Sinek. You had mentioned that key word of the reason you share a story is it’s more the focus of why you want to use this product, service, or why to do whatever the outcome is. That’s key. 


Then the other one is people want to make the decision on their own terms, like you said. A book that actually specifically says that is How to Win Friends and Influence People. There’s a specific chapter that talks about if you want to influence people, you have to make sure that they ultimately come to that decision on their own terms. 


Now all of a sudden you combine these two things and it’s storytelling that allows you to do that. I think that’s a valuable lesson. There are so many underlying principles when it comes to success in general. If you start reading enough books, you start talking to enough people, like your journey with how you came up with the book of living the cloud nine life, that’s what I’ve started noticing when I’ve been doing this podcast. You’re the 34th person I’ve interviewed. When we have these conversations, and with all the books I’ve read and all the podcasts, you start seeing these underlying themes. Why is a big one. How to Win Friends and Influence People, that’s a little bit different, but the why, that’s so, so important. 


It’s really cool that you brought that up, that really storytelling helps people identify the why. 


Jordan Gross 43:14 

Yeah. It’s cool that you noticed those two and shared those two books because those were two of the first books I read in my personal development pursuit in my own journey, those were two of the very first books. 


While we’re on this theme of books, we honestly didn’t even get into it, how I learned to tell stories, but one of the books that I read recently is called Stories that Stick by Kindra Hall. It’s a very, very good book about really succinct principles on how to tell really effective stories. Just to share, I come more from the camp of consume a lot of stories, then create your own. I’m not a very rigid structure. But if you are, if you’re somebody who likes rules and principles, then Stories that Stick is a really good resource on just specifics of good storytelling, powerful storytelling. 


Chris Ippolito 44:15 

Nice. I’ll probably have to add that to the to-read list. Do you mind sharing what was that journey for you as far as how to become a better storyteller? 


Jordan Gross 44:29 

Yeah. Honestly, it’s been a lifelong journey when I really think about it, as cliché as it sounds. I love movies, I love books now. I wasn’t always a big reader, but I love TV shows. Then more recently I love TED Talks, I love commencement speeches, and I love motivational videos. I put everything together to create my own stories. I never took a course on storytelling, like I said, I didn’t even write an essay for like five years when I wrote my first book. Kindra Hall’s book was the first thing I read that was very factual about how to actually tell a good story. 


For me, it was just my own individual process and emulating some of the most powerful stories that were touching me. What I do is I just try to think about the stories that I love the most, then put my own spin on it. I don’t think there has to be any structure that you follow, I’m not somebody to say that there are three ingredients for telling the perfect story and you have to have this, this, and this. But rather I think it’s really based off of telling a story for you. What story do you get most hooked on? What story do you attach yourself to? Then try to tell a story that is just like that. 


Because when you’re telling a story, when you’re an entrepreneur, you need to be your first client, you need to be the first listener of your story. When you’re writing a book, you need to be your first reader. You need to enjoy that. I tell stories that I want to hear. That’s really important. 


That’s been my journey. Then, yeah, I’ve got little tricks that I’ve picked up on that I can share if you’d like, but overall for me it’s about the individuality and the opportunity to entertain myself as I try to entertain others. 


Chris Ippolito 46:41 

Right. I actually really like that advice of tell stories that you want to hear, because I feel like it will resonate more with an audience because you’re excited about that story. It’s the same idea with a podcast or a YouTube channel. Create something that you want, then you can start adjusting it based on what your audience feedback is. Because obviously you ultimately want to serve your audience. But if I were to have started a podcast on, jeez, I don’t know, just some other subject that I’m like, “Oh, according to the markets, people want to hear blank,” whatever. If I wasn’t really that into it, maybe that passion would have developed or come about, but you’re more likely to stick to something if you’re already a little into it. Like you said, personal development, entrepreneurship, those are two areas that I’ve been, I hate using the word “passion,” but I’ve been passionate about that kind of stuff for a long, long, long time. 


We’ve definitely covered a lot. I know there are a few tips that you were hoping to share, but, in the interest of time, I want to wrap things up. But maybe in my next question you can answer it this way. But I always like to ask people before we wrap up, what is that one piece of advice that you would suggest the audience take action on so that they can level up in the area of storytelling? 


Jordan Gross 48:27 

Yeah. For me, storytelling, and I’ve said it a couple of times now, it comes down to crafting our life story. What’s going to be the most entertaining, adventurous, movie-like experience we can make in our own lives so that when we project years and years into the future, we’re a grandma or a grandpa, and we’re telling our grandkids stories, what’s going to captivate them? 


Whether it’s decisions that you’re making in business, in your relationships, in your personal lives, think about how you can be, I call it for myself, the superhero grandpa. “How are my grandkids going to look at me as a superhero based off of the stories that I’m telling them about my life, about my business, about whatever it is that I’m doing?” The way that I become a superhero is by making decisions that are aligned with my heart, with my gut, with my intuition. They’re decisions that I make where I will not be going down a path in which I say, “Well, what if I would have done the other thing?” No, I’m 100% clear on making the decision and I don’t regret not making the other decision. 


That’s what I want to say. It’s as simple as saying “looking back with no regrets,” but it’s as complex as saying every single moment we’re intentionally crafting the story with which we want to tell when we’re 80, 90, 100 years old. That’s what I think it’s always going to come down to for me. 


Chris Ippolito 50:20 

I really like that, that’s such a cool way to think about it, be the hero grandparent that you want to become now, looking back. I think that’s a really unique way of thinking about it. 


Yeah, that was really good advice, I really appreciate that. If people wanted to learn more about you and/or connect with you, what would be that location, what’s the best place for them to find you? 


Jordan Gross 50:49 

Yeah. The best place to learn more is journeytocloudnine.com. It’s all spelled out, journeytocloudnine.com. Then LinkedIn is where you can actually connect with me, it’s just Jordan Gross on LinkedIn, I answer every message there. 


Chris Ippolito 51:04 

Awesome. Well, it’s been an absolute pleasure, Jordan. Definitely looking forward to future conversations. Because I think, now that I’ve gotten to know you a little bit better, there’s a lot of similarities and commonalities here. 


All right, well, anything to wrap up? 


Jordan Gross 51:22 

No. I think, especially if you’re listening to this soon and you’re in the midst of coronavirus yourselves, just stay safe, stay healthy, stay happy. Understand that with uncertainty there is no correct response except the overly negative response. Just feel how you want to feel. But if you win, you win. If you lose, you lose. No matter what you learn, you learn. Just keep going through this experience with faith and hope that we’re all going to get through it. I hope when you are listening to this we are through it. 


Thanks again, Chris. Please reach out, anybody, I’m always here to chat. 


Chris Ippolito 52:08 

Awesome. Thanks, Jordan, take care. 


Jordan Gross 52:10 

Thank you.