458- Your Grass is Green Enough: Unlocking Growth and Thriving Right Where You Are 🌱🌟 TTST Interview with Jason Silver

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Jason Silver is a multi-time founder of kids and a multi-time founder of companies. He gets his biggest thrill helping modern employees and their teams unlock a better way to work—surfing is a close second. He was an early employee at Airbnb and helped build an AI company from the ground up back before AI was the cool thing to do. Today, he advises a startup portfolio valued in the billions on how to build great, lasting companies that people actually enjoy working for. He’s a sought-after public speaker, instructor, and advisor on how to transform work into one of the biggest drivers of positivity in your life. When he’s not busy helping people solve their hardest workplace challenges, Jason’s kids are busy reminding him just how much of a work in progress he still is too.

“Enjoyment is actually the fuel for success. The more you enjoy what you’re doing, the better you’ll do at it.” – Jason Silver

fERGIE’S tOP 5+ Knowledge Nuggets and Take-Aways

  1. Your Grass Can Be Greener 🌱 – Instead of running from dissatisfaction, look for ways to improve and transform your current environment. You might already have the tools to thrive right where you are.
  2. Start Something from Scratch 🚀 – Don’t shy away from building something new. The early stages of any endeavor may feel daunting but offer immense opportunities for growth.
  3. Listen Deeply 👂 – To improve your relationships and problem-solving, practice intentional listening. Understand others fully before responding or taking action.
  4. Prioritize Enjoyment 😊 – Find joy in the work you do. Enjoyment fuels success, leading to better performance and personal fulfillment.
  5. Align with Your Intentions 🎯 – Regularly check if your actions align with your deeper intentions. True success stems from staying on the path that resonates with your values.
  6. Learn by Taking Action 🏃‍♂️ – Don’t just plan; do. Hands-on experience teaches you lessons you won’t find in books or theories.

Level 🆙

Fergie

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Pick Up Jason’s Book:  Your Grass is Greener

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Music Courtesy of: fight by urmymuse (c) copyright 2018 Licensed under a Creative Commons Attribution (3.0) license. http://dig.ccmixter.org/files/urmymuse/58696 Ft: Stefan Kartenberg, Kara Square

Artwork courtesy of Dylan Allen

Speech Transcript


 

L. Scott Ferguson: [00:00:00] Time To Shine Today Podcast Varsity Squad. This is Scott Ferguson, and I had a fantastic conversation with the author of Your Grass Is Greener, Jason Silver. Fantastic coach, hands on, super curious. Super fun conversation. Also, I have a pretty sweet book giveaway if you listen towards the end For his book his book is a super Knowledgeable read actionable items to be able to get out there and take action on what he actually teaches you in the book and they’re all Solid solid knowledge nuggets.

So if you’re really kind of looking to level up feeling a rut please Listen to this or , somebody please share it with them or hit like and subscribe because my sponsors and affiliates absolutely love that So without further ado here comes my really good friend author of your grass is greener.

Jason silver. Let’s level up

 Time to shine today podcast varsity squad This is scott ferguson and I got The people that know me know me know that i’m from the midwest and from michigan I used to make a lot of trips over to where my guy here’s from jason [00:01:00] silver he’s in toronto, but he also kind of winters down, in the let’s just say the islands It’s a very nice pleasant place to be and I might even try to pop over and meet him because I do Go to that island, , at least twice a year, which we were laughing about off the mic But his name is jason silver.

He’s a multi Time founder of kids, which I think is awesome because he’s, he’s got a plethora of kids. Awesome. All boys good luck to his wife and a multi time multi time founder of companies. His, he gets his biggest thrill helping modern employees and their teams unlock a better way to work.

Surfing is a close second. He has an early employee. He was an early employee at Airbnb and helped build an AI company from the ground up back before AI was the cool thing to do. Today, he advises a startup portfolio valued in the billions on how to build great lasting companies that people actually enjoy working for.

He’s a sought after public speaker, which he does rock the stage people. So if there’s anybody out there looking to level up your audience, please, please reach out to [00:02:00] Jason. I’ll give you all the information. He’s a instructor, advisor, and how to transform work into one of the biggest drivers of positivity in your life.

When he’s not busy helping people solve their hardest problems, Workplace challenges. Jason’s kids are busy. You’re right. Reminding him just how much of a work in progress he still is. So not as the only easy, like a handsome devil, well spoken devil, but he’s a huge, he’s got humility as well, man. And this is the kind of people who like to surround her with squad.

So Jason, thank you so much for coming on. Please introduce yourself to the time to shine today. Podcast varsity squad, but first what’s your favorite color and why

Jason Silver: vivid blue pearl. It was the color of my first car.

L. Scott Ferguson: What was

Jason Silver: that car? It was an old RSX.

L. Scott Ferguson: Oh, really? Yeah. It

Jason Silver: was two. I love that thing.

L. Scott Ferguson: You wish you’d get it back. Maybe, ,

Jason Silver: I was, it was like, I thought it was the greatest thing ever. , I was able to afford it when I was younger and every car I’ve had since then has just gotten crappier and crappier and crappier because I brought kids, they mess it all up, but I just like, I remember the [00:03:00] days it was like a stick shift.

It was so fun. It was a two plus two. , now I got the like SUV that. It looks like a bomb went off inside.

L. Scott Ferguson: Yeah, those days I do remember. I, I miss them sometimes, but I’m also kind of glad I’m passing. Cause it was a lot of car detailing , money going out the door, but Jason, , thank you seriously, man.

Thank you so much for coming out. What you do for people is above reproach, man. I’m so glad we got to carve this time to come out, but I love to know the roots. Like, where did you get started? To be where you’re highly sought after coach speaker. I mean just an overall badass. So like let’s get to the roots.

Jason Silver: Yeah Thank you. I mean i’m gonna ask you to follow me around more often and introduce me when I go places. I got you in a heartbeat , it’s one of those things where You look backwards and the story seems so put together and clean and clear. And when you look back at it, it makes sense when I was going through it, I’m still going through it now.

You know, I, I dunno, you just, you kind of do the things that make sense along the way. I, I think the one thing, [00:04:00] the one thing for me that always kind of stood out or I I’ve kind of realized it, , as I’ve, Been more retrospective recently is I’ve always had this value of like looking left when everyone’s looking right when there’s the conventional thing to do I kind of naturally reject it and sometimes that’s not the right thing to do because everyone’s doing a thing because that’s the best way to do it and it’s easy and I don’t do it that way to cause me a lot of pain and other times it results in me winding up in situations that I never possibly could have imagined like Winding up talking to you because i’ve written a book You If you asked me five years ago, 10 years ago, 15 years ago, I said, I’m not a writer.

I’m not gonna write a book. Sure. It’s just one of these things that kinda, I think that value played a big role in why am I starting a company? Why am I leaving a very comfortable engineering job? , I was at Airbnb, as you mentioned for a while. Yeah. Why did I leave there? When the company was going way up into the right.

I think all along the way, that was just a value. That played a big part. Is it something that you. Want to be kind of a [00:05:00] creator of something more than kind of on board with something or where, where does that really come from? Where does that drive come from? Yeah, because I mean, you bailed on a company, which all due respect rock on.

L. Scott Ferguson: Dude, that’s awesome. It was skyrocketing. But like you kinda left something. It was kinda on the up. Right. And your peripheral must have been catching something. ’cause you sound like me. We look at things peripherally, ? Yeah. Versus straight up and down. I’m just really curious about that.

Jason Silver: I loved my time there and I didn’t leave because Oh, I don’t like this company.

I don’t like my job. , I left because I love building companies. Like that’s what I’m, I’m passionate about. And I had an opportunity to join an AI company that was barely even a company at the time that I got to join it. And, , there are certain kinds of challenges that I really like, and I’m more of a zero to one person than I am.

, once the thing exists, let’s tweak the knobs a little bit to make it more efficient and better and dah, dah, dah, dah, dah, dah, dah, dah, dah, dah. I really liked that challenge. It’s very hard. It’s very stressful, but I’ve always liked that challenge. And I think that’s, [00:06:00] that’s the thing that’s always, always.

, most interesting to me is here’s an opportunity to build a thing. There’s no roadmap for it. No one can tell you how to do it, but you got to figure out your own way. Every time you do it as different, I’ve done three startups. Now I’ve been involved in four startups now, not including the business that I, , built and run.

Now. I never think about that as a startup.

L. Scott Ferguson: You love, it seems to me like you correct me if I’m wrong, but you love to do the heavy lifting. Right. I mean, it’s like you get, ,

Jason Silver: it’s, it’s funny when, because I run in startup circles, , often startup people think about enterprise people and enterprise people think about startup people.

It’s like, well the grass is always greener on the other side of that. , it’s not to say that I think people who work in at bigger companies, they do a lot of heavy lifting too. It’s just the nature of the work they do is different. I really like the freedom, which again comes with a lot of anxiety, but I like the freedom of, well, I don’t know, , Like we’ve not done this before.

There isn’t like a manual on how to accomplish this thing. Sure. I like that kind of iterative, , it’s, it’s more ambiguous. I like that environment better. It just suits [00:07:00] my personality, I guess.

L. Scott Ferguson: No, it’s awesome. I mean, like you’re the jet fuel that gets things like. Off the ground. Like if you’d see a plane take off, it takes so much to get it up.

Then the course directions will get you somewhere. And I’d want you on my squad if I had something to launch, man. So, , thankfully, there you go, baby. So do you, do you work with people one on one or what’s, what’s kind of the, the facet of your company? Like, give us a rundown of what you got going, brother.

Jason Silver: Yeah, so, , I’ve been very fortunate to make I think almost every mistake you can make in business, I’ve seen some successes as well. I’ve just had this like breadth of experience. And I now I work with folks helping them build their companies. And I guess the conventional term would be coach.

I don’t think about it like that. , we talked about what I’m up to, I call it startup personal training reason being. It’s like a personal trainer in the gym, right? You go to a personal trainer and sometimes they’re telling you how to do the exercise because you’ve never done it before. Sure.

Other times there are, , they have their hands underneath your elbows as you’re lifting the barbell. So, , drop it on your face and kill yourself. And [00:08:00] sometimes they want to get a workout too, and they work next to you. And so what happens is I’ll work with CEOs, their leadership teams, other executives and they bring me their biggest, hardest problem, whatever’s going on right now.

And we. , bash our heads together until they leave with like a, I know what to go and do now, , I have a clear next step that I didn’t have before. And the feedback I get from folks is they really appreciate having a different perspective in the room. , I’m deep enough that I know what’s going on in their business and they don’t have to catch me up, but I’m not so deep that, , you can lose the forest for the trees so to speak.

So, yeah, I love, it’s a lot of one on one stuff. I do a lot of workshops, helping teams kind of improve the way they’re working, help them pick up pace, things like that.

L. Scott Ferguson: I’m curious then, like, okay. So I. One of the things that I still from, if you’re watching on Vimeo, YouTube, you saw me do that squad, but like, , I was like, like when I get brought in by like the CEO or a C.

Fo not cfo ceo or coo usually kind of calls me and they hear me speak or something want to call me and [00:09:00] talk to the company because they’re struggling or they , they’re just Something’s just not getting off the launch pad And it has more to do with kind of mindset than the actual work because i’m a coach.

I’m not a consultant People have forgot more about their businesses than i’ll ever know So it sounds to me like you’re a little bit more of a coach sultan because you’re getting in there and getting it done but to get back to what I was saying is When you walk into a company And you have that one person, like, what the hell, why are you bringing this dude in?

Like, how do you work with that person? And also the higher echelon to get kind of everybody to be cohesive and to make it a well running company.

Jason Silver: I mean, I don’t mean this to sound arrogant, but it hasn’t happened yet. No, it has happened. It doesn’t often happen.

L. Scott Ferguson: Okay.

Jason Silver: , oftentimes I do have different perspectives than folks.

And I think that, , there’s, we’ll have times when we butt heads on something like that. Sure. But usually it starts for me with, like, I’m a very people first person. And I wasn’t like this always. I grew up I came up as an [00:10:00] engineer, very technical thinker, like, tell me about the problem we’re trying to solve.

And people, Are one of many inputs to solving the problem. Okay, and now if you bring me a problem The first thing I think about are who are the people involved? What are they trying to accomplish? What matters to them? My man, and so if you threw me into a situation and someone was like, who’s this guy coming in here?

Like we don’t need him. I would I would want to talk to that person, , and I would want to understand What’s going on for you? Right? Like, what are you trying to accomplish? What are the reasons why you think you’re obviously feeling threatened in some way, shape or form? Like I would want to unpack that and understand why.

And then I would want to understand the rest of the team dynamic. Most likely there’s probably some kind of mismatch incentives or we’re not aligned on the job that needs to be done and the impact that I can help provide. Usually I find you kind of have a big open dialogue early. It’s a hard conversation, but you have it opened early.

It, Gives everyone a chance to, okay, let’s like, let’s work through this stuff.

L. Scott Ferguson: You pull that, rip that bandaid off, man. And actually, dude, I [00:11:00] usually become closest with that person. Like almost like not buddies or anything, but they, they, they just, sometimes they’re in a position where they don’t feel like they’re heard and you make them feel like the herd and you kind of pass things along, it works.

So I’m thank you for like attacking them out, , from the start. So then Jason, what do you feel makes a great coach?

Jason Silver: So I’ve been fortunate to have many great coaches, and I would probably, if you want me to elicit the attributes of what makes a great coach, I’d probably check, I’d probably check zero of those boxes, and that’s why what I do is, is a little bit different, but it’s not, maybe not zero, but I have, I have my way.

, I think when I think about traditional coaching and the way, the reason why I don’t really fit in that, That bucket is I think a great coach. Their job is to help you figure out what’s going on for you And and to be great at that requires you to have a you have to be a great listener , you have to help guide someone towards it What I tend to do that they coaches that in my past [00:12:00] haven’t done is i’m an operator by nature I’ve built businesses.

I’ve crashed businesses. I’ve been part of businesses that have been scaling very very quickly You I’m very opinionated. A great coach probably wants to be keeping their opinions to themselves. Sure. Right. Like Scott, I don’t think this is the right approach for you is maybe not the right thing to say, , at the outside of a conversation, when you’re a coach, a lot of times I’ll get into conversations with the CEO or whatever.

And, and, and I’ll start with, here’s an anecdote of a time I tried to do it the way that you’re describing, which is not to say that my way Is it going to work for you now? But let me tell you this story and let’s see what happens. And then a lot of times where we wind up going is someone will bring an idea and I will whip rocks at it until the idea either gets thrown in the garbage because it wasn’t right.

Or it becomes so hardened that that executive is like, yep, I’m very sure this is the thing I want to go and do. And we do it in a safe space. So I’m highly opinionated when we have conversations. And I think that’s what a lot of my clients like is, Hey, , This isn’t like, , a [00:13:00] therapist session, so to speak this, this is like, we’re, we’re going to get deep in the operations and figure out not just like, what’s the aha moment, but how do we action it?

 that’s the thing I’m always very, very focused on is like, , someone should leave a session with me feeling like they have a specific thing they can go and do, , I wrote the book, every chapter is having a very specific thing you can go and do, , there’s nothing worse than having a conversation with somebody reading their book or whatever you feel so fired up, and then you go to do a thing, you’re like, Oh, wait a second.

Like that was, that was, that was a cheerleader moment for me and I feel great and that’s awesome, but I am like, Oh man, I’m still stuck at the starting line. , I think that’s what I really try to help people with is, , advice is only helpful in so far as it’s actionable. If it’s not actionable.

, what are you, what are you gonna do with it?

L. Scott Ferguson: No, I love that. Like, I, with my clients, I’ll put them in their car, right? If I’m blessed to coach them in, , South Florida and like put them in the driver’s seat and me in the passenger seat, one, I want to see how they keep their car, if they’re neat or not, , I don’t judge it.

I just like Don’t look [00:14:00] at

Jason Silver: my car. Yes. Right.

L. Scott Ferguson: But put them in the, the, the, the driver’s seat and say, listen, man, this rear view mirror right here. It’s small for a reason, right? That’s your past. If you need help there, you got a therapist, you got to get a therapist. This windshield, big, huge, scary. Oh my gosh, where the hell are we going?

You know what I’m saying? And you look at it since 2011 ish or so, they’ve been putting this thing on the dash called the GPS, right? And again, what you had said is a great coach to help you figure out. Help you figure out what’s going on and how to get better. Like I can’t buckle the seatbelt for him, put the car in drive, start it and take off.

Right. But if something goes, the tree falls down, you got to get another round or bad traffic. You can plug different things in. And for me as a coach, as a great listener, in curiosity my superpower as it is yours is Like that’s key is let them do the freaking work man, because every challenge they have inside the the action to take is there too You just like you I can just [00:15:00] see talking to you man Yeah, leaning in listening with your neck and really helping out and I love that you admit the transparency of of Not of being opinionated because some people need that, , they just do here.

I’m

Jason Silver: not saying that my opinions are correct, , I think right I have I have my way of doing things, right? It’s not that I I come in and I had challenges early in this particular person I was doing where I would often get a lot of questions about Is this strategy right? Is this the right approach?

Is this the right goal? Is this the right thing to go and do? And I struggled with that because, , I’ve seen some companies and I’m like, this company is going to fail. And they did the exact opposite. And I’ve seen other companies where this company, , they’re going to go through the roof.

They went through the floor. And what I learned is we just can’t predict the outcomes. And so. I, I don’t answer the question of is this right or wrong? What I focus on is I really try to help people with their intentionality. Can we understand what your intent is? What are you trying to accomplish and why?

What I can help them do that often people in the business [00:16:00] can’t help them do is I can help them figure out whether they are aligned with their intent or not, right? So, hey, you told me that what would be a great example of this? Like, you told me that there’s a certain kind of team that you want to build.

Right. And here are your values. And we’re talking about hiring this person who sounds technically incredible, big brain, really great, but they’re not checking the boxes of the kind of person you want in the company. Right. I’m going to call that out to you and tell you, I’m not going to tell you whether this is right or wrong.

I’m going to tell you that this feels misaligned from the intention that we previously talked about. Now with that information, you can make whatever decision is right. , you might decide, you know what, I’m going to break the rules I set previously. I’m going to update my intention or whatever it might be.

But. That kind of like what’s your intent and how close or far are you from that path? At the end of the day, , i’ve crashed a company what I what i’ve learned to care about is Sometimes a company will fail. Sometimes a project will fail win or lose. I gotta do it my way I gotta do it in a way that i’m proud of and I I try to help people make [00:17:00] sure that You’re not going to look back and regret this you were intentional up front.

You did it on purpose You did it, the way you wanted to do it You Thing goes work out. They don’t work out. That’s kind of out of your control. What is, is the way that you behave, the way that you operate, the way that you make decisions as you’re kind of working towards whatever outcome. And there’s always another outcome.

L. Scott Ferguson: Yeah, I absolutely love that, Jay, because it’s so many people, like a lot of people will step into something, have like imposter syndrome because they’re linking their confidence to their abilities. They haven’t did it yet. So it’s there, but you’re talking about linking that confidence to the intentions.

That’s what, that’s how I was able to lean in and, , coach, , Che Harlow, three comma guy, , billionaire, that I go in and, and coach him because my intention is to make you better and take what you want and to get better at it. So once, and I’d love that you always are circling back to the intentions.

That’s, that, that to me is the epitome of a great coach, period. ’cause you’re bringing him back and holding that mirror in front of him and saying, dude. , this is what we got. So [00:18:00] with your maybe working with somebody, you’ve given your opinions, you’re kind of running back and forth. Just making sure you’re, you’re the right horse for the course, right?

For them.

Jason Silver: Is

L. Scott Ferguson: there any good question that you wish they would ask you, but never do? Why would we not work together? I love that dude. No one’s really, I’ve asked that from a few coaches. They’re like, dude, I don’t know, but not, I like that. Give me a reason why it wouldn’t work out. Right?

Jason Silver: Yeah. I tell people all the time, , I, if I’m talking to a potential new client, I will read them this.

And I’ll tell them like, here are the reasons why we, the anti sales pitch, right? If any of these things are true, I’m not the right person for you. And I will help you find somebody who’s better. And assuming that we don’t check those boxes, then there’s probably something great here. Right. I think the thing at the top of the list is we got to mesh as humans.

Right? Like just the way that I operate, like I’m not going to hold back. I don’t want them to hold back either. Right. And someone might talk to [00:19:00] me and realize like, this isn’t my type of person. , I just don’t think we’re going to have like the relationships not clicking in the right way. And that’s totally fine.

, it’s not a knock on me or them. It’s just the relationship might not click and it needs to, there has to be a lot of trust. I want it to be enjoyable as we go through it. Cause it’s definitely going to be hard. That’s kind of, , thing number one. And the only way to test that is to try, , you have to have a couple of meetings and just see like, what does that look like?

Does this feel like something I’m going to want to do over and over and over and over and over again. And then the next thing is we’ve kind of already talked about it. If you want someone who’s going to sit back and just pull opinions out of you and not have any of their own opinions, I’m definitely not the right person.

If what someone’s looking for is. Hey, I want to I want to figure out my personality traits and the personality traits of my team. And then talk about how we can like best work together. That’s not me. It’s not to say that stuff’s not great and helpful. I’m just not great at it. It’s not what I do. It’s not what I bring to the table.

So those are kind of the. The the key pieces that I like to try to walk people through and say Here are the reasons why it won’t be a fit and I think more people should [00:20:00] ask it I try to ask anybody I go to work with is like this feels right Tell me what I might be missing here, , tell me why we shouldn’t work together

L. Scott Ferguson: and Love it that you’re humble enough to say listen, it’s not working.

It might not work for us, but I have somebody Or I’m going to work to find somebody because that’s the whole premise behind time to shine today. Our credo or motto, whatever it is, we don’t want to have anyone to feel like they have no one. So no matter your situation, I’ve interviewed over, , 500 coaches, right.

And I’m able to put them with somebody that’s going to work for them because I’m not the right guy for. , probably 80 percent of the people just because of my trans, my authenticity is where I come from and I care a lot and I get a little bit, maybe aggressive, , they need somebody that’s a little bit less.

And I interviewed 20 of those kinds of people. So I love that. You’ll still put him in the right direction. So let me have some, have you seen the movie back to the future? Of course. Okay, let’s go back. I know we’ll go the first one. Let’s go back to the [00:21:00] double deuce. The 22 year old Jason. Okay, what kind of you got that glory in, went back with Marty and visit the 22 year old Jason.

What kind of knowledge nuggets might you drop on him to not change anything because you have four awesome kids, wife, all that jazz, but to maybe shorten a learning curve and maybe blast through maybe just a little bit quicker.

Jason Silver: I have two kids and sorry, two. Sorry about that. If, if I do actually have four, then then I’m gonna go back maybe.

Sorry about that. Love . Yeah. I’m gonna go back in time and change that. ’cause two is more than enough for me to hang. I don’t think I could take another two. But I, I think like, , it’s the same message that I would want to give, I try to give other people as well, and it’s not for me to tell people how to live their lives, but, , I, I, I was and still think I am a type A.

I just think the way that I. have evolved is to think about being a type A differently. And by that, I mean, like, I really genuinely love to achieve things. I’m constantly thinking about like, what’s the next thing I’m going to accomplish? And how do I get there? And I like to have something like that, [00:22:00] multiple of those things.

L. Scott Ferguson: Sure.

Jason Silver: But 22 year old me put all of the investment in how I was feeling and what I was doing and my self worth and all that kind of stuff in the accomplishment of those achievements. And now I flipped it entirely on its head. Those achievements serve a purpose in my life, but they don’t define it.

The definition for me now is about what I’m doing in the moment. How am I living my life? How am I working towards the achievement? Because the thing that I’ve learned is no matter how much I try. I don’t control the outcome. Sure. And, and I could do all of the right things in quotations. I could do all of the right things and work all of the right hours and all of the right ways and make all of the right decisions and still not accomplish the outcome, , you don’t have to go back to 22 year old me to remember the pandemic, right?

Nobody saw that coming. Right. And like businesses blew up then. And, and our lives got put on hold and went in different directions and this, that, and the other thing. That’s nothing that. I [00:23:00] caused, , it’s not a causal relationship. It just happened. Right. And what I’ve kind of learned from, , I’m a bit of a like armchair neuroscientist now.

I’m really interested in, I spent a lot of time reading about it. Like, when you focus entirely on the achievement, right, you just, you feel happier for like a blip. And then you just go back to your baseline, right? And the way i’ve learned to feel way happier exactly is just and I never knew what this meant be present like live in the moment Yeah, those sound great their platitudes, but I was always just like I don’t know what that means I’m, not a monk.

I can’t go sit on a hill and think about this , and so I I’ve really been focused on like, how do I make that more tactical, right? You want to be present you want to live in the moment how and that’s the big shift i’ve had of , I’m talking to you now in part because of this, , I wrote a book, I have to promote the book.

I don’t have to, but I choose to promote the book. There are, I don’t want to say infinitely many, but the list is very long in terms of the ways that I could choose to promote the book. I really like meeting new people. I [00:24:00] really like answering questions. I like asking questions. I like having conversations.

Of course, I’m going to choose podcasts as one of the principal ways I’m going to promote the book. I enjoy it. Right. It might result in, , a whack load of sales or no sales at all, but I’m going to enjoy the process along the way. And I think that’s, , that is really important. And I, I wish I had known that a long time ago.

L. Scott Ferguson: Right. It, it, it took me some time as well. I was so in a rush to get somewhere. Now it’s like I do the whole ris buer when he says, , life goes by fast if you don’t stop and take a look around. Right, right. I mean, it’s, I live by that now and I try to have my clients, especially my athletes, to really get in that moment and, and enjoy this journey because it does end, bro.

Well, you perform the

Jason Silver: best when you enjoy. This is the thing I didn’t understand, ? Mm-hmm . I used to think that like, enjoyment is fluff, ? Right. I’ll enjoy it. When I achieve all these things I want to achieve.

L. Scott Ferguson: Yeah, right.

Jason Silver: And what I’ve learned is actually, [00:25:00] there’s a ton of research about this too, the more you enjoy what you’re doing, the better you do at it.

It’s that simple. So enjoyment is actually the fuel. Yes. And so now I’ve started thinking about, how do I optimize, not entirely for my enjoyment, , work is hard, it’s not always fun, there’s a big difference between fun and enjoyment, we get those confused, , like, fun is always enjoyable, Enjoyment is not always fun, right?

If you’re, I’m a runner, you run at the end of a, of a long run. I am not having fun in that moment, but I enjoy the act of running overall. When I think about my career, some of the most enjoyable moments. We’re not fun. It’s like something has blown up and the team is in a room and we’re working really long hours and we’re trying to figure out what the heck’s going on with a tight deadline.

Like that was not fun in the moment. I wouldn’t have told you like, this is great. I love like sleeping and working, but looking back incredibly enjoyable, like very fulfilling moment. And so I really started to think about how do I break down enjoyment? How do I [00:26:00] think about enjoyment? Not as like. I think to do once I’ve accomplished these, but actually the thing that leads to more accomplishment and once I started optimizing for that, it kind of flipped away.

I was living entirely on my, on his head.

L. Scott Ferguson: Yeah. Yeah, I exactly. You’re like a little brother from another mother, man. Cause I’ve been through kind of. Every one of those evolutions that you’re going through with that, which leads me to like, how do you want, then your dash remembered that little line in between the incarnation date and your expiration date, your life date and death date.

Hopefully it’s way down the road, right? But how does Jason want his dash remembered?

Jason Silver: That’s a very, very big question that I’ve not spent a huge amount of time thinking about, but. I want to be like net positive for the people around me. Like I, I measure my worth now in the worth I’ve increased in others. , I [00:27:00] feel great when it’s like, if I’ve helped this person in this way, or if I’ve done this thing with the intention of helping these people in that way, I can’t help everybody, but , I would want people to remember me as.

Sure, it’d be great if like, ah, that guy was so fun or, , this, that, or the other, like that would be great. But if the things that people really remembered was this one time he did this thing for me and it had such a big impact for this reason. And this other time he did that thing. And it was so helpful for that.

Like, , the other day I got an email from someone that I had worked with a long time ago and they have this memory of a thing I did for them that for me, it didn’t even register. I’m so grateful that it did. They sent me this note and, , probably made my month to get a, to get a note like that.

So some version of that.

L. Scott Ferguson: And you also like that, those are like little teachable moments. As you kind of go through life is saying, dude, be more present. It’s like, it’s like subconsciously hitting that reticular activating system to say, dude, be more present. You’re going to notice where [00:28:00] you did this for them.

And it’s like, that’s, , that’s why I’m really big with gratitude and intentions with my clients in the morning by 9 a. m. Three things you’re grateful for in your serious intention for the day. Yeah, that’s where we’re going to build the confidence, right? We

Jason Silver: end, we end, , there’s seven and four.

We end every day with like, what are you grateful for from one thing? You got to be able to think of at least one thing.

L. Scott Ferguson: Right.

Jason Silver: Yeah. I mean, again, the research on this show is like, gratitude is like a happiness pill you can take, , you just, when, when everything’s blowing up, you take a minute and you’re like, well, what am I grateful for in this moment?

Thank you. To flip that on its, on its head a bit can have such a, such a huge impact. A

L. Scott Ferguson: hundred percent. Like if you were to get a Tesla, Right? I didn’t know what one was. You’re like, Fergie, man, you got a Tesla. Come over and take a look at it. I go over there and I see you’re like, emotionally liking it.

I’m like, wow, that’s a really cool car. How many Teslas do you think I’ll see on my ride home? Okay. That’s the same thing with gratitude, brother. You start that day, it fires up the reticular activating system and it just brings in more. Right? It’s just, there’s a [00:29:00] science behind it. Not just the secret movie.

What I’m saying? Or the book. There’s a science behind that stuff, brother. You do it and my clients see it. Even my , two comma and three comma clients are like And they do they’re like shit man. My kid’s talking to me again i’m saying or made love to my wife for the first time in three years, It’s like

Jason Silver: yeah, dude, it can have a big impact, , and I think this is why I kind of sometimes think about myself.

I mean, this is such a silly analogy But like I think about mary poppins, , like here’s the medicine, but it’s in honey , a lot of the stuff that I’m really passionate

L. Scott Ferguson: about. Oh, we forgot about that. But yeah, that’s right, dude. Yeah. ,

Jason Silver: it’s like I work with a lot of these executives and I try to do it for myself as well.

But, , we have to accomplish stuff like you have to, , you don’t have the luxury nor would you want to if you’re running a company, just go sit on a beach with your feet up. You probably would go nuts.

L. Scott Ferguson: Right.

Jason Silver: And so just telling someone to like, enjoy the moment more. You’re like, well, how do I enjoy the moment?

I got a to do list 8, 000 things long. Right. And so what I’ve been trying to do is like give medicine with the honey. It’s like, we’re still going to accomplish all the same stuff. We’re not going [00:30:00] to change the tasks you need to accomplish. We’re not going to change the job you need to get done. We’re going to change the way that you do these things.

Right. And, and the thing I’ve always been really, really focused on is like, I’m a momentum person. Right. There might be some gigantic milestone we’re trying to get to. And I want to get there, but I’m going to try as quickly as possible to show you any amount of momentum, even a small amount, even to your point.

It’s like this gratitude thing. And the test example is a great one. Like, I’m going to tell you to think of something to be grateful for at the beginning of the day. And then I just want you to pay attention to how much more you’re grateful for throughout the day, tiny, tiny, tiny bit of momentum, but it’s, it’s, it’s something, you know?

And I think for me, you talked about like the jet plane getting off the ground. Like I think about that all the time. It’s just like, how do we get. Momentum. Any amount. In a compound, right Jason? Exactly. You

L. Scott Ferguson: know?

Jason Silver: Exactly. It’s so hard to get started. That’s, that’s like the, the, the cold start problem is real.

Almost everywhere in life I’ve found is just that first step, no [00:31:00] matter how big it is, is so hard. Cause you’ve got a million reasons not to take it. It’s not going to work. This is going to fail. I don’t have time. I’m too busy. I’ve this, that, the other. It’s very easy to find reasons not to start a thing.

But once you start, , A lot more progress.

L. Scott Ferguson: Absolutely. It makes it a little bit easier. Just course corrections along the way and squad.

Time to shine today, podcast versus squad. We are back and Jason, I’m going to definitely make it a point to meet up with you live so we can enjoy a brain grenade or two, and maybe just chat a little bit and pick your brain and, and level up myself, but I’ll ask maybe some of these questions and we can talk 15, 20 minutes on them, but today you have five seconds with no explanations and they can all be answered that way.

Brother. You ready to level up? I’m frightened. Yeah, let’s go. So Jason, what’s the best leveling up advice you feel you’ve ever received?

Jason Silver: About like what we talked about is why are you doing this? Are you going to enjoy it?

L. Scott Ferguson: Share one of your personal habits that contributes to your success.

Jason Silver: [00:32:00] Hmm. I spend a lot of time thinking about intent. Meditation is very helpful for me. Awesome.

L. Scott Ferguson: So you see me kind of walking down the street or an event or something like Fergie looks like he’s in his doldrums a bit, , not your, other than your book, your grass is greener, but like another book that you might’ve like dug into that really flipped that switch to get your mind right.

Jason Silver: Ooh, tons. A big shaker for me was a courage to be disliked. I recommend that one. It’s actually good, dude. Great book. I’m reading incognito now by David Eagleman. He’s like a neuroscientist. I’ve read all of his books. I love this guy. It’s a lot about how the brain works. And I love that stuff too.

L. Scott Ferguson: Your most commonly used emoji when you text.

Jason Silver: I’m not a big emoji guy, so, but it’s probably either thumbs up or a smiley face.

L. Scott Ferguson: Awesome. Nicknames growing up.

Jason Silver: Some people sometimes called me Chevy, like Chevy Silverado, but oftentimes just like silver was the most common.

L. Scott Ferguson: Oh my God. That’s awesome. You have any [00:33:00] hidden talent or superpower that nobody knows about?

Well, until now,

Jason Silver: these are hilarious questions. I have a thing about like, if I see someone being able to do a thing and I’m interested in it, I go maniacal trying to learn it. So I got a bunch of those, like, I can like juggle, ride a unicycle. I learned how to moonwalk one time. There’s a bunch of embarrassing stuff that I’m not sure I can still do.

L. Scott Ferguson: Chest checkers and Monopoly.

Jason Silver: My oldest son loves games. He’s playing them all the time. So I do those a lot. Monopoly is happening a lot right now. I probably would

L. Scott Ferguson: Kurt perfect headline for

Jason Silver: your life.

L. Scott Ferguson: Oh my God. I have to answer this in five seconds. You got to put it on a billboard on the side of, , the, the freeway, bro. Thank you. Okay. That is pretty fricking awesome, dude. That’s beautiful. Go to ice cream flavor.

Jason Silver: There’s something in here called moose tracks.

L. Scott Ferguson: Legit bro.

Jason Silver: Yeah,

L. Scott Ferguson: absolutely.

Remember I’m from Michigan. So there’s [00:34:00] a sandwich called the Chevy Silverado. Build that sandwich for me, man. What’s on it. Oh

Jason Silver: my God. Whoa,

L. Scott Ferguson: and

Jason Silver: it can’t be like a burger.

L. Scott Ferguson: It can be whatever you want,

Jason Silver: man. Yeah, I love a good burger It would be a burger. Very cool. Probably some probably some avocado on it.

There you go onion for sure. Hell yeah

L. Scott Ferguson: Hell, yeah favorite charity and or organization like to give your time and or money to

Jason Silver: Princess Margaret Cancer Foundation is really important for me. And , we have one up here too, that helps immigrants in Canada. It’s important to our family as well.

Nice. Called the Matthew house.

L. Scott Ferguson: Nice. Thank you for doing that. Last question. We can elaborate on this one. What’s the best decade of music? 60s, 70s, 80s, or 90s.

Jason Silver: Oh, you’re opening up a can of worms right there. I see a guitar

L. Scott Ferguson: in the back, dude. Yeah,

Jason Silver: it’s like, yeah, , I have a very eclectic taste in music.

So I would probably tell you all of them. But I really, I think the seventies was such a [00:35:00] great, great time for like, , just, You’re a storyteller, man.

L. Scott Ferguson: , like what I saw a little bit on stage with you, you’re a storyteller and that’s what happened in the, I’m, I graduated 1990 from high school, right?

So the eighties was my jam, but if I’m listening or preparing for a speech or something, I always have the seventies on in the background, right? Because it’s like, there’s stories in it and there’s. So

Jason Silver: authentic too, , you can’t hide behind like autotune. There was like, , right now I’m reading, also reading Slash’s autobiography and he just talked about their first album and how it was the last album that they ever made, where It’s literally being mixed by a bunch of people who you mix it live, , The track plays you gotta mess with all the buttons and then it went digital after that And so I just think it’s not that I love music now truly if for different reasons but back then was just a bunch of people in a room, , you gotta you all play together and It’s a great musicianship.

I think [00:36:00]

L. Scott Ferguson: hbo just dropped a three part series called nothing but a good time I think I would check it out. Cause it starts back, , with the first kind of hair bands, , in the sunset strip and the troubadour and all that jazz, and it moves into like your Motley Crue, your poison and whatnot, and how they got phased out by the grunge and stuff.

But I think you’d really enjoy what Slash has to say on it. It’s really solid. Check it out. Yeah, if you haven’t

Jason Silver: read his autobiography, it’s

L. Scott Ferguson: it’s

Jason Silver: a little bit all over the place. I’ve heard. He’s

L. Scott Ferguson: like, dude, I’ve heard about that, man.

Jason Silver: I can’t believe he’s alive. It’s it’s shocking. Good for him.

L. Scott Ferguson: Insane.

Insane. And also the, the movie, The Dirt, the one about Motley Crue, that when Nikki overdoses, that dude with the hair in his face to the right of him is slash supposed to be slash. Right. But yeah. So we got to dig into your book, man. Like your grass is greener. I always have a joke. People will say, Oh, the grass is always greener, but I’m like, dude, the water bill is more expensive.

You know what I’m saying? Because like, I’ll, I’ll hear that. Like, , man, I’m going to leave this chick cause the grass is grass. I’m like, dude, then you got to date someone new. You got to pay [00:37:00] for everything over and over again. Right. , and stuff like that. So I was intrigued by this and with all full disclosure, I should have read it.

And I apologize for not, but I’m, I’m going to actually grab it tonight and read a lot of it on my flight to Denver. But tell me, like, what kind of was the the, the, the kind of the jet set start for this? What kind of, we talked about, , build that rocket ship up because you got a lot of good reviews, man.

So,

Jason Silver: yeah, I just felt like there was a part of the conversation missing, , and, and it was in kind of two ways. The first is like, , if you get a job, you love, you’ll never work a day in your life. Obviously, show me one person like that. I’ve never felt that, , I have moments like that, but work is work.

It’s work. That’s why it’s called work, right? And, and you have to work at it. You have to practice. In my opinion, a dream job is something you practice. And a lot of what I’ve been seeing is, , you look at like the great resignation, people are quitting, they’re leaving jobs. You look at the statistics on it.

80 percent of people who change jobs during the Great Resignation, millions and millions of people, 80 percent of [00:38:00] them regret the change. Okay, and so it usually feels like the easiest thing to do is change your environment, right? I’m just going to go get another job somewhere else that’s going to make it better.

That’s right. And usually it’s better for two or three months. Right. There’s a honeymoon phase, but because you don’t change the way that you’re working, all of the frustrating things that were happening tend to come back. And, , the caveat is you might be in a really, really toxic work environment.

That’s a time to make a change. But the assumption out there is it’s my boss. , it’s my work environment. It’s my job. It’s my this. It’s my that. And I’m trying to say in the nicest way I can, it might be you. You. Thank you. And if you change some of the ways that you’re working, more tactically, right?

So, work smarter, not harder, is a thing that people say all the time. I find that borderline offensive. I’m not waking up in the morning and saying, Hey. What is the dumbest way I can accomplish this stuff? I’m trying to work smart, but nobody’s really explaining. Here are some specific things you can do differently, right?

And so what I wanted to do is take the nine [00:39:00] most common challenges at work, Miscommunications are very frustrating. Decision making is really slow. Imposter syndrome makes me feel down. I’m not enjoying the work that I’m doing. The nine most common challenges and give a highly specific tactic that you can try.

So it turns into basically a manual of if you try all nine of these things and you see no improvement whatsoever. Perhaps it’s time to make a change, but it’s way easier to improve a situation that you’re already in. You can make the grass greener where you are. And I felt like that’s just missing. It’s just totally missing.

You can read a hundred books on how to find a better job, how to interview, how to like become purpose driven, dah, dah, dah, dah, dah, dah, not a lot of stuff on how do I change what I’m doing day to day so that I enjoy it more so that. , it leads to a bigger, better, whatever life, , whatever, whatever you’re looking for.

L. Scott Ferguson: I love the knowledge that You you do work. It’s needed like you meaning like if you love what you do, dude, i’ll tell you what I do Love coaching. I love this what we’re talking about rapping. I Hate the rest of the stuff, [00:40:00] right? The because as you grow a business That stuff has got to get done, , or I’ll just, , here in the state.

Jason Silver: I’d love you to give me feedback on the book. , the middle section of the book is all about how to take the stuff that you have to do, , and you can’t always delegate it, right? , this, you run a business, you have to do some of these things, right? How can you do them in a way that you’ll enjoy more?

Right. Number one, you do them better. And number two, you just enjoy it more as, as you’re working your way through. And a lot of times what I found in writing the book and researching the book and what have you is we actually. We kind of rely on best practices too much. And that’s another term that I don’t love, which is like best for whom, right?

The best way for you to do a job may not be the best way for me to do a job. And because in my experience, almost none of us factor in enjoyment. We don’t think about, I have to go from A to B. What path am I going to enjoy the most? Because it feels like fluff. The enjoyment doesn’t matter. I just have to accomplish it because we don’t think about that.

We actually don’t have like a clear roadmap of. These are the kinds of things I like to do and the [00:41:00] ways I like to work, and I can apply them to any task I need to accomplish so that I like it more and do it better, etc. And so I give people tactical exercises to like, here’s really quickly how to pull this out, and here’s really quickly how to apply it to this, whatever is on the top of your to do list for tomorrow, and you’ll see, you’re gonna like it more.

L. Scott Ferguson: Love it. And, and, I love, is there a part in there where if it, to keep it afloat? Like, , let me read it and I’ll get back to you on that. I’m just going to intonate that out because I don’t even want to go down that right now, because, and I’ll explain it to you off mic. But

Jason Silver: we can do

L. Scott Ferguson: it now.

Whatever makes it, no, no, no, we’ll do it off. Mike, let me just pull this up here. So I just want to, did I close that? Nope. Squad. I’m going to Share the screen with you real quick. If you’re watching vimeo or youtube you can find it on amazon and It’s there. It’s also directly from jason’s website as well, which is there either one Please pick it up and I am going to do [00:42:00] a two book giveaway the first person that says , just put Chevy.

I’ll know that you’ve listened, put Chevy in any, I don’t care if it’s Pinterest, Instagram, Facebook, you text it to 0, I don’t care what text it. And I will have a book mailed on time to shines dime out to your to your address and Jason, if you could. Please leave us with one last solid that we can, knowledge nugget, that we can take with us, internalize, and take action on.

Jason Silver: First, thanks for doing the book giveaway. It’s always exciting for me when someone’s going to get a book in their hands. So, , thank you. Thank you very much. And I think the, the knowledge nugget is, is like, I genuinely believe that people have more agency than they think they do. So if you’re out there and you like, you feel stuck or you’re not enjoying something, if you’re like a situation is, is, , not going the way you want it to go, I genuinely believe that, that you have more agency.

There are some [00:43:00] tactics in the book that I think could really help. Maybe one I’ll just pull out. It’s right at the end of the book, but it’s, it’s one of the most transformative questions that I’ve ever learned to ask. And I’m a big question person is you look at something that you’re thinking about, or you need to accomplish, or something that you think looks very hard, or we don’t know how we’re going to do it ask this very specific question.

What would need to be true? It seems so simple. But because most of our brains have a negativity bias, it’s really easy to see all the reasons why something isn’t going to work. And that is a very valuable exercise. Because it’s going to pull out a lot of risks. Right. Right, and we’re going to see, oh, it might not work for this reason, it might not work for that reason, it’s going to fail me because of this, that, and the other thing.

And that will help you build a plan. Love it. But you don’t want to do that in absence of what would need to be true.

L. Scott Ferguson: Sure.

Jason Silver: Right. And when you write that list and you suspend your disbelief from it, you’re like, I’ve gone through all the reasons why this is going to fail, burn, destroy my career, et cetera, et cetera, et cetera.

I’ve done that task. Do the opposite task of what would need to be true. One, two, three, it’s probably going to be a [00:44:00] shorter list. But often I find that when you intentionally take time to write down the list, you realize, well, wait a second. I actually think some of these things might be possible. Let me try and see what happens here.

So taking a little bit of time and asking, , what would need to be true? Every tactic in my book in some way, shape or form drops out of that. The fact that I have a book, , dropped out of this, what would need to be true for someone like me who, isn’t famous? , you haven’t seen my face on a billboard anywhere.

How could I write a book? , And the results have been for me on, I can’t believe the reception of the book. I’m honestly shocked by it. I love it. Yeah. You have solid

L. Scott Ferguson: reviews. Everything is, is good in squad. We just had basically a free masterclass. Sorry if I kept you a little bit longer than usual.

But we had a free masterclass here with my good friend, Jason Silver, , that, , looking back, he reminded us that stories become clear. And a little bit more clean, , but he always took those calculated risks and never made excuses. He made adjustments , he’s a zero to one [00:45:00] kind of person.

He loves to do the heavy lifting, , a great coach will help you figure out, help you, you figure out what’s going on. He listens with his neck. I can actually see him leaning in, listening and really picking up the, , ready to fire off the next question to help you get that aha moment, , like he’d mentioned.

From aha to action moments, , he under, he wants you to understand what your intent is. Are you aligned with your intent or not? , your achievements serve a purpose, but it does not define you. He reminded us, , he has an enjoyment in optimizing people’s lives. He’s doing things for the intention, not the attention, which I love that because you don’t see him on social going, look at me, look at me.

I’m Jason Silver. I have this. I have that. No, he’s why he’s giving. Of himself, , he’s out there wanting to make your life better. He’s planting trees He’s probably never going to sit in the shade of he lives a life of a net positive for the people around him , we want you to remind that you do have more agency and ask yourself when you’re at a crossroads What would need to be true or [00:46:00] what is true and that’s where the magic happens pick up his book Just, just go out, pick it up.

I’d have a two book giveaway. I’m sure that those are going to go fast, but go pick up this book and let’s give some feedback, write the reviews and let me know what you think as well. Good, bad, or indifferent. Jason, thank you so much. You level up your health. You level up your wealth. You burned your varsity squad letter here.

Time to shine today, brother. Absolutely love you guys. Thank you so much for coming on.

Jason Silver: Thanks for having me Scott. Thanks to everybody who you know, made it to the end and listened all the way through. Appreciate your time to chat soon.

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