June 26, 2025

How To Know When You Should Start Your Side Business

Billy tells the story of how came to know when it was the right time for him to start a side business, including all key points, markers, and insights that you can use yourself to understand how you can know when it’s time for you to start a side business of your own.
Billy Keels
CEO and Founder FGCP

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Going Long Podcast Episode 537: How To Know When You Should Start Your Side Business

 ( To see the Video Version of today’s conversation just CLICK HERE. )

In today’s solo episode of The Going Long Podcast, you’ll learn the following:

 

  • [00:17 - 00:58] Introduction to the show.
  • [00:58 - 11:00] Billy tells the story of how came to know when it was the right time for him to start a side business, including all key points, markers, and insights that you can use yourself to understand how you can know when it’s time for you to start a side business of your own.
  • [11:00 - 11:57 Billy wraps up the show.

 

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What you can expect to get out of this course:

  • Learn How to Achieve Financial Optionality
  • Gain True Control Over Your Career
  • Turn Corporate Skills into Personal Assets

With 26 years of experience in corporate sales leadership, achieved optionality through multiple income streams, Billy has helped dozens of executives build their paths to take control of their time.

This free course gives you everything you need to identify, plan, and take control of your career while building financial optionality, leveraging your skills, and start living your IDEAL day - today!

Go to: https://www.makeitoptional.com/  

To see the Video Version of today’s conversation just CLICK HERE.

 

How to leave a review for The Going Long Podcast: https://youtu.be/qfRqLVcf8UI  

 

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Episode Transcript

Billy Keels  0:00  How to know when to start your side business. Today's episode is sponsored by Billy Keels advisory services. If you want to learn more about how to make your 99 optional, just go to make it optional.com. Once again, that's makeitoptional.com. How to know when to start your side business is absolutely the episode that you are going to want to listen to. If you have ever had that doubt as to when was the right moment for you to begin your side business, especially when you are a high paid executive who is highly visible. And when I say highly visible, I mean that you feel like you have to be everywhere all the time, because if you're not, then things are not going to go according to plan. The reason I share that with you is because in this very brief episode, I'm going to share with you what happened to me and when I realized how it was the moment for me to know when I should start my side business right and very just jumping right in one of the things that constantly happened to me, because I am a classic high performer, overthinker and self proclaimed recovering perfectionist. There were moments when I was learning about and for me, the vehicle of choice to help me move beyond and have much more control was real estate. I started looking at real estate, but I never figured out early on when was the right moment for me to start the side business. Why? Because I was constantly addicted to my very high paycheck, the benefits, the nice employee, discounted stock purchase program. I had RSUs. I had a nice German car, luxury car. I had gas paid for. I had great health benefits, all of these things and every so for so long, I thought that if I did something outside of what I was doing in my nine to five, for instance, five to nine or five to 10, then it was going to negate everything that I'd been working for in my corporate life. And that simply, I can tell you now, it was just a false belief. It was something that I was telling myself. And I'm getting right to the point now, because I don't want you to continue to go through the same pain and suffering that I was going through that was pretty much self inflicted, right? Because at this point in time, I'm going to go back to when I was in my very early 40s. I've got two young kids. At this point in time. I was married, my spouse didn't work. And you know, so all of the financial responsibility of our household fell on my shoulders, right to make sure that the house was functioning financially fell on my shoulders. Actually how it was functioning on a day to day? Well, that was not my responsibility at that at that point in time. So if you are in that point, or you feel like that's your point, like I've been there, because my whole thing is, I just at that point, I felt like I needed to make more money, because the more money that I made, then that made me feel safer, like I could provide as well. So it was like a really good thing for me. But at the end of the day, what I started to realize was, yeah, you can make a lot of money, but I just, I still had to ask my boss if I could go on vacation. So I just wanted to be able to have much more control over my time. Ultimately, was what I was looking for, and I, and I felt like that, that side business that was going to give me the way to produce a predictable stream of income, have much more influence over who the clients were that I was serving, et cetera, et cetera. But there was this reality where I was in my nine to nine, because that's ended up what it was, what it ended up being working more hours. I thought the more hours that I worked, the more I can make more money, and it was going to put me in a better position to actually go for more promotions, be much more promotable. And I know I've talked about this in multiple episodes, but I was drinking the Kool Aid. I was drinking the corporate Kool Aid, so much to the point that I chose to go to a business meeting. And I say I chose, because ultimately I could have stayed home, but I think I would have not felt like I was going to be promotable, or that was going to put me at risk of being able to provide for my family. But I chose a business meeting over going to my son's third birthday party. Right? I saw my son. I saw him that that day, but the party, the culmination, the celebration, I wasn't there, and that changed something inside of me, that broke something inside of me, to make me want to do something different. And I realized at that point in time that my energy started shifting from like saying that the nine to five was everything to really, really starting to break it up and figuring out, okay, what can I actually be doing from five to nine or beyond, that's going to give me much more control, because I was very fortunate. I had a boss who who was a role model for me, who actually showed me that he was building his own retirement plan outside of corporate. And so when I had that POC, that proof of concept right in front of me, it was a game changer, absolute game changer, because I realized he was actually creating predictable streams of income, like he got very specialized, and he was doing real estate as well, and he was doing that back in Scotland. And I was like, wow, I've got to figure this out. I've got to replicate this model, because I want to do something very similar for myself, not exactly the same thing, but something very similar. I. But here's the reality, like, I had to put together my own personal plan, but I didn't want to talk to my boss about it. I didn't want to talk to my colleagues about it. I definitely didn't want to bring that stuff home, because at the time, I actually I didn't have the support that I really needed at home. My wife wasn't a big fan of me going out risking this whole, you know, great job, great benefits. And so I had to figure out, like, where do I get the support that I need that's going to help me to move beyond just consuming videos and listening to podcasts. I needed to do something else. So I figured out a very simple plan that I'm going to share with you. The plan was purchase a rental property and put enough money to the side that if I lost 100% of the money, life would still go on. I would have had an experience, and then I just go back to doing my corporate role. But the whole thing about, how do you know when to start your side business? That moment happened for me when I realized that it was possible, because I saw my boss doing it, and I realized that I didn't want to continue to have to depend 100% on my employer for my financial independence, as well as being able to control my time when that happens to you, not if, but when it happens to you, listen to yourself, and I'll tell you why, because I was torn for such a long time between my Corporate loyalty and wanting to follow up after my own dream that I over. Thought about it right? Eventually, I bought this property that that was my first kind of taste to figure out, okay, this side business I didn't even think about I thought of it as a side hustle, something I was going to do on the side. But that hustle turns into a business, because when you are like me, someone who is a high performer. You've done it in corporate. You don't just want to have quick fixes. You want to build something that's long lasting, that's sustainable. How to know when it's when you're ready to build your side business. That's the other thing when you should start it. Because I don't necessarily know if you're ever going to be ready, but you will become much more competent and and and confident as you take more action. Like I said, I was torn between my corporate loyalty, because that's what I was told I should do, you know, be completely loyal, and I had this false belief that I couldn't be loyal if I was doing something else on the side, right, but I needed to go after my own dream so that I could feel much more fulfilled. I over thought about it. It took me almost five years between 2008 and 2013 thinking about things being theoretical mastermind. But eventually I did make that purchase five years into it, right? What could I have learned in that five year period of time? How much opportunity cost did I lose? I try not to think about that too much, because what I really want to focus on, and what I what I want to share with you, and how you know when you should start the side business? Because what I realized that, yes, it took me five years to think about it, but once I started taking action, decisive action, making purchases, getting someone that was there to help me, who had been down the path that I was there before that person, he helped me to cut down in the timelines and allowed me to make more purchases sooner, and it took me four years of taking decisive action. While I was building in my day job, I was building my own dream on the side, and it allowed me to live the last four years of my corporate career in a state of optionality. And what that specifically means is, once I started my side business, that that predictable stream of additional income became multiple streams of additional income because I was building a very specific, specialized knowledge in a in an area, and I was getting more reps. And that helped me to realize that the expenses that I had for my from my life, for my family, the income that was being produced by my businesses, on the side, was paying all of those bills, which allowed me to go into my day job feeling even better, really recognizing that I could contribute to others, and I wasn't worried about what my title was. I was more thinking about how could I contribute to others, meaning my coworkers, my clients versus trying to chase a title. That's what optionality gave me. It wasn't just the money, it was the ability to be and feel free when I was in my day job and freely build and and make my side business even stronger, right? That's the whole point, becauseBilly Keels  9:18  I was controlling my time. That's what the whole optionality thing is about. It's about you feeling in control, you having the income to be able to cover the expenses, those expenses that make you continue to feel trapped, independent, 100% on your employer. I was the best. I mean, I was in the top talent program. They called it catalyst, but I was in that program while my business was covering all of my my my expenses, my living expenses, my life expenses, I was living in a state of optionality, and I it felt good ask my bosses, ask my ex coworkers like I was the happiest person. I even had my my LinkedIn moniker said Happy corporate employee because I was you. Because I enjoyed my day job, because my side business when I knew to get it started and started, and it wasn't perfect when it got started, made a lot of mistakes, but got to a point where that helped me to understand that I could be confident in what I was doing, building predictable streams of additional income, serving clients that I wanted to serve, and also being, most importantly, in control of my time. So if you're wondering how to know when to start your side business, listen to yourself. You already know. And if you feel like you need help, reach out to people that can help you, but don't, don't do like I did, and stay stuck in theory for five years, because you perform well in your corporate job, you're definitely going to perform well, not perfectly, as you begin to go from side hustle to side business, right? And you and everyone around you, the contribution that you can make to others is going to help to fulfill you. It's going to help you to leverage your skill set and helped to make others feel and achieve more than they actually even thought. So I'm going to stop there and this, if this is not you, but you know somebody who feels like, hey, look, I need to start the side business. I've been trying to, I've been overthinking it. It's time to go share this episode with them, but go from there, once you share it, get on the phone with them, talk to them about what they what you've shared, what you've learned here, and while you're doing that, you know what? I really love doing these podcasts. So I'm going to be here. I'm going to be preparing the next episode. So until then, go to make it a great day. And thank you very, very much. Today's episode is sponsored by Billy Keels advisory services. If you want to learn more about how to make your 99 optional, just go to make it optional.com. Once again, that's make it optional.com.

Billy Keels
Strategic Advisor, Entrepreneur, and Investor
Billy is on a mission to share a roadmap and opportunities with other extremely busy, high-performing professionals on how to find freedom and live the life they desire. Listen in to learn how!
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