The Company We Keep

On the final episode of Season One of THE COMPANY WE KEEP podcast, host Jason Pearl answers his most-asked question: What does it take to take a leap, break free, and live the life you want to live?

Show Notes

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Have a question or want to talk to Jason about a specific topic? Or maybe you just talk about the Bills?

Show Highlights: 
(00:00) Introduction
(02:00) Taking the Leap
(05:02) My story of entrepreneurship
(08:41) The gut feeling
(09:23) I was OK with failure
(10:43) I didn’t care what other people thought
(11:56) My story is not your story
(14:19) Recap + Preview of Season Two of The Company We Keep

Here’s a little advice: Don't regret starting a business and not working hard enough. You may regret not starting it, but if you're going to start it, you can't have regret.

Mentioned On The Episode: 
Nacre Consulting

What is The Company We Keep?

Jason Pearl is a second generation entrepreneur, bootstrapping business owner, loving husband, devoted dad, and raging Bills fan. He tosses aside the idea that you can't have it all and devotes his life to proving it wrong. Grab a cup of coffee and join Jason every Tuesday morning as he dives into topics to help everyday business owners and entrepreneurs think differently about growth and success, and how to achieve a better balance in both business and in life. He’s also shining a giant spotlight on some very smart people in his inner-circle that have helped ignite his success along the way.

All right. All right. Welcome to another episode of The Company We Keep podcast. I'm your host, Jason Pearl. Excited for you to be with me again today. What is The Company We Keep podcast? This is a podcast for everyday business owners, entrepreneurs, high-performers, and anyone who wants to think differently about growth, think differently about success, and wants to achieve better balance in both business and in life.

This is episode 12. It's going to be the final episode of the first season of The Company We Keep podcast. Super excited and proud of that. Today's topic has come out of some kind of questions and some experience that I've had an interaction that I've had with some of our listeners. And it comes down to the topic of what it takes to actually take the leap. And when I say take the leap that the feedback and the questions, the communication I've got from a lot of listeners is, has been about taking the leap of leaving the corporate job, and then going and starting your own business. Or if it's not even entrepreneurship, it's what does it mean to take the leap, to leave a company and go to a new one or something like that?

There's a lot of this swirling around right now. We live in a world where there's a ton of opportunity, whether it be in a W-2 job or a side hustle or starting your own business. But there's just a lot of people that I think are looking at breaking free from what traditional work looks like and trying to build a life that they want to live.And I think that's awesome.

So that's what we want to talk about today. But throughout this first season of the podcast, we've had a lot of conversations that kind of touch on this topic. We've discussed my core framework, Head, Heart, and House, and how that can and should play into how you make decisions. How you manage people, how you manage yourself, how you define your own success, things like that. We've had podcasts specifically on decision-making and how you have to personally define what success means to you. Not what society thinks success is and in so many other topics.


Today, as we get into it, I thought what would be helpful for all these people that have asked me these questions is maybe talking a little bit about what my personal journey has been and how I worked through this decision process to take the leap into starting Nacre Consulting and leaving the 9-5, W-2 guaranteed income job.

Obviously, everybody likes to sensationalize entrepreneurship and being a business owner and making your own rules, and making your own work schedules and things like that. And there are, don't get me wrong, there are tons of perks to it. There's also a significant amount of downfall to it as well if you're not careful. And one of those things is no guaranteed income, right? When you start your own business, you're not guaranteed anything, you have to work for it. Those are things that we're going to talk a little bit about.

But, I don't believe that it's ironic or that it’s just happenstance that every week a new person has contacted me asking a similar question like this. It happened again to me last night. Somebody very close to me sent me a text message, "Hey, do you have time to talk" or "Hey, can you talk?" And I said, of course, let's chat. Hopped on a phone call, and the very successful person I was talking to makes a significant amount of money on an annual basis working for a company. Is probably one of those people that doesn't worry about money or doesn't worry about how much money they have saved, but they're not the happiest at their job. And the person wanted just to have a conversation around what my thoughts are—decisions that I made and how I may be able to help. So the interesting thing is one of the comments made is that this person said, I just hate my job. I just hate it. I got to get out of there. It just comes down to the fact that is there really anything worth doing that you truly hate? Especially hating something that you have to do, probably five days a week? And there are some necessary evils of doing things that you may hate. For example, I have kids: changing a diaper. I don't know that I would say I hate it, but it's certainly not something that is the most exciting and enjoyable thing to do. But you know what, we've all been there. We've all been in diapers before when we were babies and, we need to get those clean. Or maybe it's filing your taxes, shout out to all of my accounting friends, and I have a lot of them. But I know a lot of people don't like worried about filing their taxes. Luckily this year, we got a little bit of an extension until May 15th, but shout out to all my accounting friends out there. Or maybe it's cleaning your house or cleaning toilets or whatever the case may be. But that being said, those are funny and silly things that we'll talk about, but they're necessary evils, right?

But when it comes to working, and it comes to having a job and being able to provide if you hate what you do, it's a tough existence. And not everybody that I've spoken to throughout the course of the last 12 weeks has said that they actually really hate their job. They have enough interest in doing something different or maybe changing the way they operate in their life. And that's where a lot of these questions came from. Ultimately, what I would say is, if you truly hate what you're doing, it's probably time to sit down and have some inner conversations and some thoughts about what can I do to maybe improve this portion of my life?


As we're talking about taking the leap: my story about entrepreneurship, as I've told you, started when I was a kid and my parents owned their businesses, and then I went into a corporate job after college when they sold their businesses. And I went into banking and worked for two major international banks for the better part of 12 years. At the end of my time in banking, I was being recruited to take over the sales and marketing function and strategy of a financial service company. But I, my father lived in Naples, Florida, still does. We were having very serious conversations about what it would look like to potentially have me actually moved down and get involved in his business or potentially buy into the business and really start to grow the property management business that he had down in Southwest Florida, which he still has today. I went down and flew down by myself and visited, and we had some very specific and serious conversations. Even though he's my father, when you're talking about the business, we had to have some serious conversations, and obviously, I had to talk to my wife, and my family about does this make sense? Should we move down to Florida? Should we take this leap? And ultimately, through conversation with myself and my wife and my father and my family, and through some prayer, it just came down to the fact that it just wasn't the right time. It wasn't the right time for me to take that type of leap.

It wasn't time for really, probably my father to have me enter into the business, and it just, ultimately, it was a great exercise to go through, but it didn't work out. And quite honestly, I was pretty upset about it. I wasn't upset at anyone. I was just upset because I felt like I was maybe missing another opportunity to live the life that I wanted to live, but it just didn't add up. The money didn't add up, the significance of the move and leaving family here in upstate New York like my mother and my sister, and then my wife's side of the family lives in upstate New York. It just didn't make sense. So we just altogether decided that didn't make sense.

But fast forward, six years later, there was another opportunity that came up. And I tell you this story for a couple of reasons. The first reason is: number one, not every opportunity is the right opportunity. So you have to work through that process. But when I fast forward, six years, I'm talking about my personal walk, it became a little different. The conversations I had about potentially moving to Florida and doing this property management stuff with my dad were one thing. But six years later, after I had spent time leading and growing and really expanding my skillset, my accolades, and results with this financial services company, something became pretty evident. Something was really stirring in my heart. I was maturing as a human being as an individual, as a professional. I was becoming more accountable to myself and my family, and my work. And I was certainly more in tune with my family and my faith. And I just knew that there was something out there more for me. This is all happening as I am still employed as a W-2 employee within this financial services company.

And then, as I explained a few episodes ago, it just so happened that my employment at this institution was ended. I was terminated, and I had some decisions to make. The interesting thing about that is within 48 hours after I became a free agent, I had a significant amount of job offers and conversations that I could have easily taken and transitioned into a new W-2 job. But as I was talking about, something was stirring inside of me. And as I work through what I wanted to do, there were three or four really specific reasons that I knew that it was time for me to take this leap. It was time for me to take the leap into entrepreneurship, into solopreneurship or business ownership, and just really do what I thought was the right next step. And those reasons, I'm going to list them out.


But first and foremost, over the course of the six years leading up to this, I was maturing, and there was definitely something stirring in my heart. I became more in tune with my family and what was important from a time perspective, what was important from a faith perspective for me in where I felt that I was being called by God to go. And I felt it. I never really felt anything like that before. And it was a different feeling, but it was a very apparent, very loud, very decisive feeling that I had, which was like, I have to do this. And that was important for me cause I'd never felt that way before. And I felt like this was, there was no other decision for me to make. So that was one of the main specific reasons that I made the leap.


Number two: which I think is really important for a lot of people that are made up like me. I became at peace with understanding that I may start this business and I may fail. And being okay with the ramifications of failure, I was okay with. And that was something that I'd never been OK with before. I had this extreme weight that, like, if I didn't try this if I didn't do this entrepreneurship path right now. I just felt in my heart that I would regret it for the rest of my life.

I felt the time was right. I had the right experience. I was at the right age. I just felt like I knew I could do it. And I was okay with failing, and the reason I was okay with failing because I believed in myself. Like I said, Hey, if I give it my all and I fail, then I'll go get another job, and I'll be 100% okay with getting another job. And I think that's a really important thing. I knew it was important for me. But I had a skillset, and I still do. If I had to, I go back and be a VP of Sales or CRO or go work for a company as a W-2 employee and lead their sales and revenue functions. I knew I had that skill set. Because I knew I had that skill set, I knew that if I tried and failed, it's not like I'd be living on the street. I'd be able to go and market myself and find a position. So that was another way that I was able to work through the decision of, is it the right time to take the leap? Because of that reason, the answer was yes.


Another really specific reason was that I actually had zero interest in caring what other people thought or said about me at this point in time. That was not something that was normal for me. I've explained, and I've been vulnerable on this podcast before, to say that I've probably had an issue or a problem worrying more than I should about what people thought of me, what people thought of my skill, and all of those things. And at this time in my life, four years ago, I was not anywhere close to caring about what anyone thought or what anyone said. So I didn't have a parachute. But I had really complete clarity that I knew that this was the right move for me. In knowing that I didn't have a parachute, and knowing that I didn't have like a whole bunch of money saved just to be like, Oh, if this fails, I'll just live on the beach for six months, and everything's going to be fine. I didn't have a parachute, but I didn't care either. I knew I could get more work if it didn't work. And I knew God was pushing me in this way. Those three or four components made me realize that this was the time was now and the time was to take the leap.

And so that's what I did to, to a lot of people's dismay, not my wife or not my family. They all believed in me and supported me and things like that. But I just knew that the time was right because of these three or four things I just laid out.


But my reasons for taking the leap are not going to be the same as yours. And that's the thing like this isn't just do everything I say, and everything's going to work for you. You understand what's going on in your Head and what's going on in your Heart, what's going on in your Household. So our circumstances are very different.

The one thing I want you to take away from this podcast is if you plan on taking the leap, you better be all in. Don't dip your foot in the pool. Jump in, do a cannonball, do a belly flop, right? And if you want to take the leap, you have to 100% do it. You have to do it with all your conviction, with all your heart, with all your efforts. Because if you try to enter into entrepreneurship or business ownership and you think that it's, Oh, this is going to be great. I'm my own boss now. So I'm going to sleep in late, and I'm going to take long lunches, and I'm never going to do what I'm supposed to do, is like you're gonna fail pretty quickly. So if you're gonna to make the leap, give it your all: believe in yourself, make sure that you've worked through your decision process and those that are part of your life that are important to you are those that you're responsible for. But if you're going to make the leap. Be all in. You owe it to yourself to be all in. Regret is something that no one likes. So don't regret starting a business and not working hard enough. You may regret not starting it, but if you're going to start it, you can't have regret.

I talked about earlier in my career, which would be about ten years ago when I made the decision not to take the leap. That was probably the right decision. I worked through that with my wife and my family, and there's nothing sexy about saying yes or sexy about saying no. You have to know what's right for you and what's right for the situation. Everyone needs to make the right decision for themselves and who they're responsible for. So you have to prioritize what's most important to you and then use that as your beacon for decision-making.

That's my story, but my story isn't your story. And if there's something I could employ you to do is go make your own story. I know I talk a lot about my personal experiences. That's part of why I'm doing this podcast because I think it's easier for people to relate to personal stories. Cause they may find some overlap or some consistencies that they're dealing with. And I love the fact that I can be that for you. And maybe that helps you a little bit. But the fact of the matter is my story is not yours. You've got your own story. You've got to go make your own. Your life's a book. You’ve got chapters left to go, so write them. Don't talk about writing them. Go write them. And if you take that attitude and you take that approach, you're going to succeed. Because when you're all in, and you know that this is something that you should be doing, go write those chapters that are left. That's what you have to do.


This is the last episode of season one of The Company We Keep podcast. Quite honestly, I'm proud of the fact that this will be episode 12. The people reaching out has been really fun. It's been awesome and super encouraging. So I'm really honored that you're listening and really appreciate everyone that's been so supportive of me throughout this process.

That being said, there will be a season two, and there will be a season two very shortly, and season two is going to be awesome. It's going to be a little different than season one. We're going to be introducing you to a lot of amazing people that I get to call friends or that are a part of my network.

We're going to be introducing you to some video, some really interesting concepts. And we have a few other tricks up our sleeves that we're really excited about. If you may be having caught all of The Company We Keep podcast episodes so far, over the course of the next few weeks, it's going to be a great time to catch up.

It's also going to be a great time to communicate with me and interact. I'm still going to be really active on socials and my website, but we're going to take a little bit of a pause as we build out season two, but there's going to be a lot of really fun stuff happening. And I can't wait to introduce you to some of the people in my network. So we aren't close to being done. We are just getting started. We just want to make a positive impact on this audience. We want to help equip you with all the things that you need to help achieve your goals but ultimately achieve growth in the areas that you deem important, and that you want, and the areas that are most important to you.

So, if you're enjoying this podcast and this content, I would love and really appreciate it if you subscribed to it. I know a lot of you have, but there are probably some of you that are listening that haven't subscribed. We'd love for you to do that.

And if you're so inclined, leave a review as well. But throughout the next few weeks, and at any time, you can find anything you need on me and on this podcast at Again, that's Jason, M as in Matthew, I'm Jason Pearl. Thanks for keeping me company today. This is The Company We Keep podcast I'm out. Peace.