September 1, 2026

Finding the Right Side Business Model for Your Corporate Skill Set

Are you an overachieving director, VP, or senior AE burning the candle at both ends because you’re forcing a cookie-cutter side business that doesn't fit your background? In this highly strategic solo episode, host Billy Keels breaks down why choosing the wrong side venture model leads to intense overwhelm, wasted energy, and a loss of your most critical asset—your time. Drawing from his 26-year corporate career managing $100M EMEA operations for a legacy German enterprise software titan, Billy shares how he built a side asset engine generating $212,000+ per year in additional revenue. Discover how to analyze your current resources using the high-level "invest or build" framework, calculate your exact optionality number down to the decimal place, and trade the limiting fear of failure for a powerful mindset shift: What if it actually works?
Billy Keels
CEO and Founder FGCP

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Are you an overachieving director, VP, or senior AE burning the candle at both ends because you’re forcing a cookie-cutter side business that doesn't fit your background?

 

In this highly strategic solo episode, host Billy Keels breaks down why choosing the wrong side venture model leads to intense overwhelm, wasted energy, and a loss of your most critical asset—your time. Drawing from his 26-year corporate career managing $100M EMEA operations for a legacy German enterprise software titan, Billy shares how he built a side asset engine generating $212,000+ per year in additional revenue. Discover how to analyze your current resources using the high-level "invest or build" framework, calculate your exact optionality number down to the decimal place, and trade the limiting fear of failure for a powerful mindset shift: What if it actually works?

 

🚀 Want to make your corporate role optional? Grab your FREE copy of Billy's 3-Step Process eBook here: https://www.makeitoptional.com/?utm_source=youtube&utm_medium=social&utm_campaign=p2olm

 

📌 Questions Answered in This Episode:

  • How can a senior corporate leader find the fastest side business model to generate quick wins?
  • What is the hidden relationship between your available capital, required control, and the business path you choose?
  • Why is knowing your career optionality number down to the exact decimal point critical to stopping the endless work loop?
  • How does answering the question "What if it does work?" shift an executive's transition confidence?
  • What does it feel like to spend the last 4 years of a corporate career completely independent of a company paycheck?

 

⏱️ Episode Chapters:

  • 00:00 - Creating Professional Optionality Aligned with Your Values
  • 01:10 - Reclaiming the Global Strategy: An Overview of 26 Years in Corporate
  • 02:30 - The Illusion of the President's Club and the Reality of Paycheck Dependency
  • 03:40 - Burning the Candle at Both Ends: Reaching a Year-and-a-Half Breakthrough
  • 04:55 - 5 Years Outside the Enterprise: Why the Corporate Game Stays the Same
  • 05:40 - The Strategic Fork in the Road: Evaluating the Invest vs. Build Model
  • 06:35 - Tracking Your Escape Route: Why You Need an Exact Decimal Number
  • 07:50 - Navigating Unfamiliar Spaces and Embracing the Discomfort of the Unknown
  • 08:35 - Shifting the Focus: Olivier Jadoul and asking "What If It Does Work?"
  • 09:50 - The 41 Streams of Income Engine: Managing 400+ LP Units
  • 11:00 - Walking into Boardrooms by Choice: Shifting From Theory to Skill Mastery

 

Featured/Mentioned Previous Epsiodes:

 

Episode 623:  https://www.billykeels.com/podcasts/turning-ambitions-into-real-world-actions---olivier-jadoul 

Episode 615:  https://www.billykeels.com/podcasts/the-truth-about-when-to-build-or-invest 

Episode 457: www.billykeels.com/podcasts/how-to-easily-identify-the-number-to-make-your-job-optional 

 

📘 About Billy Keels & Corporate Optionality

If you're a corporate executive who wants to make your role optional, learn how to achieve true control over your career and turn your corporate skills into personal assets.

With 26 years of experience in corporate sales leadership, Billy Keels achieved true optionality through multiple income streams. Today, he has helped dozens of executives build a predictable path to take control of their time and start living their ideal day.

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

Be sure to connect with Billy:

 

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Episode Transcript

Billy Keels  0:01  

For 3000 years, masters of the game Go believed there were only two possible plays in every situation. Then an AI model executed move 37, a play no human had ever imagined, which completely shattered 30 centuries of conventional wisdom. In this episode, I reveal how you can use a beginner's mind to find your own move 37 in your corporate career. So let's dive in and let's get you to optionality. 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 makeitoptional.com. Once again, that's make itoptional.com.

Speaker 1  0:44  

Helping you build freedom without losing your edge. This is the Going Long podcast with Billy Keels.

Billy Keels  0:57  

I love being able to share the different things that I am doing, or the things that I'm reading, or the people that I'm interacting with here on the podcast, because this is a way for you to recognize this the day-to-day things that are happening or that are being done. There's a constant reflection in the things that you are going through on a day-to-day basis, and this is absolutely no different. But this thing is like this story that I want to tell you has to do with a board game that people have been playing for 3000 years, and it also tackles one of the biggest challenges that I see as I am beginning to work with new clients, and also too when I'm having interactions with people that I meet on LinkedIn, because there's a lot of conversations that I'm having with people on on direct message, but this one specifically, this goes back to one of the one of the stories that recently, like I've been reading this book. Right, the book is the Creative Act, a way of being by Rick Rubin, and Rick Rubin is a very famous producer. And this whole thing-it also made me think of a conversation that was having with a friend of mine recently, which is we are called human beings, not human doings, for a reason. And so, this whole story about this book that I read-it really, as I mentioned, it touches on one of the things that I see very frequently. And I want to share this with you because I want it to be an unlock, so that you can recognize that limiting beliefs are lingering constantly every single day, and this book is no different because in this book, one of the chapters it goes into a specific board game. Now, this board game has been played for 3000 years, literally 3000 years. I'd never even heard of it. It's called Go, and people are you're probably going, yeah, Billy, how can you not know of Go? Well, I don't. I didn't know of Go. If you don't know it, you can look it up. It's the information is there. But very interestingly, in this specific story, he starts talking about what happens in terms of like how we limit ourselves. And so there's this board game called Go, and then there because it's been around forever, and people have mastered the games, and there's literally communities all over the place. Well, recently, not so recently, but like in the last you know couple couple decades, these communities have come up with an artificial intelligence model, and the artificial intelligence model is called AlphaGo. And why am I telling you the story? Well, because AlphaGo is constantly competing against humans and humans against the artificial intelligence. This is not a joke. This is a real thing. And so I don't know when you're listening to this or when you're watching this, but but this is real. So especially because right now there's such a heightened awareness of like it's it's human versus artificial intelligence, or artificial intelligence, human versus machine, right? This whole kind of thing. But the reality is, it's never about the human versus someone else. It's always about what is in between our ears. It is what is between your ears. It is you versus you, and it is the beliefs that are continuing to either be suppressed or limiting in terms of what you're able to achieve. And this story about Go and AlphaGo is one of the best that I've read in a really long time because there's this certain moment. Now imagine this: there's this master of the game, so a human being who's playing against AlphaGo, and they start going and keep about keep in mind that this game board has you know there's a com over 100,000 different combinations of moves that you can make. Well, at a specific moment in time, they get to move number 37, and then move number 37. It is the artificial intelligence AlphaGo. It is AlphaGo's moment to actually go, and so as you read through the story, you recognize that there's really one of two moves that people have been playing for over 3000 years. And if the AI would have taken move A, it would have shown that AI was going in a very offensive way.

Billy Keels  4:59  

If if the AI would have taken move B, it would have been a very defensive way. And so, as the moment waits and builds and builds and builds, what nobody expected, what nobody expected, not even this game master, was that AlphaGo, the artificial intelligence, selected move C. Let me repeat that again: the AlphaGo selected move C, and there's really only two moves that people have been doing for over 3000 years. When that happened, the master of the game, who is the human being, irate outside of himself, gets up from the table, walks out of the room. Nobody understands what's going on. He finally comes back into the room, completely looking dejected, recognizing that the move that the AI made that no one had anticipated, because for 3000 years everyone thought it was move A or move B. The AI had the beginner's mind. This was not like intelligence. This was a machine that had been learning, but been learning from scratch, from watching other players play, but not from human intervention, not from previous lessons, and nothing held the AI back. There were no limiting beliefs. That's the whole point. Yes, he'd been watching. Yes, or yes, the AI had been watching. Let me not say he or she, but the AI had been watching. But the AI continued to have a beginner's mind and continued to look at new ways of being able to do things. And these are the type of approaches that, when we talk about limiting beliefs, like you can literally, when you're looking at a situation, you can have the beginner's mind. I like to even tell people, like when I'm looking at something, I am looking at it. If I don't have previous knowledge, it is from an ignorant perspective, meaning lack of knowledge. It doesn't mean stupid. It means lack of knowledge, but it also it removes like the knowledge blocker, right? The artificial intelligence didn't have it. All the previous experiences from watching everybody else do what everybody else thought is the thing to do. It's like when you're thinking about the role, what people talk about nowadays is what is the next logical step. Like when you are a sales business development rep, then you move to sales development rep, and then you go from there to account executive, from account executive to senior AE, from there to manager, manager, director, because it's the next logical step for everybody else, Right, that's one path. There's also another path, which is, I'm going to continue to do this forever and ever and ever. 40 years, get to go watch, and well, maybe that's the logical step for everybody else. But how about you? You like what you're doing, you enjoy your role, and you've got this desire to do something else on the side, but your limiting belief can tell you continues to tell you. Well, you know what? You're going to lose this. You're going to lose that. And be careful this. Be careful that. I know that that happens. Ask me how I know. I lived it. I've been through it. I understand it. And it's that same limiting belief that will tell you that you are unable to continue to overperform in your corporate role and be able to successfully build a profitable business on the side, which gives you more control over your time and over your income. But take you back to move 37. Is it really just A or B, or is that your limiting belief? That's the question. Is it your limiting belief? Because the thing is, is once you get through that point of that ignorance or that innocence, that is the actual thing that is going to allow you to create new innovation so that you come up with your own move C. It means yes, you can continue to perform in your role in corporate, and I didn't say or and be able to build your business successfully on the side while overperforming. That's the whole point, because when you combine these experiences of the past with the curiosity that you have today to be able to do something different. That's what puts you in the winter seat. That's the thing that begins to squash the limiting beliefs and allows you to be better placed to live your best life tomorrow, right? And so, think about it in the same way. Is there move C?

Billy Keels  9:42  

Is it really you have to follow the path that everybody else is following? The reality is, is up to you. If you feel like you need help, well, as Deion Sanders says, and I say it every once in a while, I ain't too hard to find. Lots of ways. Check me. On LinkedIn, find out there, figure out what's going on, but more importantly, I want you to recognize that this is up to you. You can choose move C, just like AlphaGo did on move 37. And so, if that's not you, if you're not struggling with limiting beliefs today, maybe you know somebody else that's struggling with limiting beliefs. You know what? The only thing you have to do: share today's episode with them. Just click and share it. But then show them that you care. Get on the phone, talk to them. Have a go meet them. Have your favorite warm or cold beverage. Talk about these concepts. Go from theory to practice. And while you're doing that, guess where I'll be? Yep, I'll be right here preparing for the next episode. So until then, go out and make it a great day. And thank you very, very much.

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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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