As Aesop wrote, "A man is known by the company he keeps." That's a moral that still applies 2,600 years or so later, and in a similar vein, the Rule Breaker Investing podcast should be happy to be judged by its audience -- and the caliber of their questions. Motley Fool co-founder David Gardner is once again tackling those queries in a mailbag episode, and he's received some excellent ones.

In this segment, listener Nick has a big thank-you for the Fools -- his subscription fees may have taken a big bite out of his fledgling portfolio, but they've been worth it -- and a question that's as much philosophical as financial. He has a side project that could potentially deliver some success -- but it'll take a lot more of his money to bring it to the next level. Should he invest in his dream, or stick with building a strong portfolio?

To catch full episodes of all The Motley Fool's free podcasts, check out our podcast center. A full transcript follows the video.

This video was recorded on June 26, 2019.

David Gardner: Rule Breaker mailbag item No. 4. This one comes from Nick Jackson. Nick writes, "Dear David, I'm writing to you to show my appreciation and with a question. Firstly, the appreciation. Every year, I try something new. At the beginning of 2018, I decided that thing would be learning to trade stocks. Note I say trade. Like many people at the beginning of their investing campaigns, I wanted a quick buck. I'm proud to say I did fine with that. I turned $800 into $850 by the end of March, a time when the market was hiccupping." That means, in three months, he went from $800 to $850. "But it was draining to watch scanners," I don't even know what that is, "and movements closely every day. Without getting into the details, I'm glad that I found The Motley Fool. After reading several of the articles you guys put out and looking at the track record of you, David, I decided that trading was not what I thought it was, that I wanted to be invested in companies that I love, think are fun, and do splendid things.

"It was around my birthday, apparently very close to yours, near the Ides of May, that I decided to purchase subscriptions for both Rule Breakers and Stock Advisor." We see an emerging theme in this month's mailbag. A lot of talk about Stock Advisor and Rule Breakers. Well, Nick goes on. "This was a big decision, as the cost was roughly half of my invested funds at the time. But a year and some change later, it's paid for itself twice over, and I still have a year left. It was an investment I made in myself, and it paid me greatly and will continue to do so. That's a good segue into my question."

Before I read your question, Nick, I want to say back, great job! It is an interesting question and answer for a lot of us -- how much would you spend to learn investing? How much would you spend on your own financial education? On the one hand, we say things like, "Try to keep your costs of investing below 2%." That would include commissions or any other fees that you might be paying for financial professionals in your life. I think that makes good sense. But that's more steady state, once you already know how things are doing for you, how things are going to go. You already understand investing. But for a lot of us, we don't understand investing. That's a big theme of this week's podcast. How much would you pay for a tuition to learn the markets for the rest of your life? I think it's quite a lot. If you were to do the math, you'd see you should be willing to pay quite a lot. So, on the one hand, when I read that Nick spent half his money at the time to subscribe to our services, I think, "Oh, he could have invested that in stocks. Maybe that was a misallocation." But then again, I think, no, that's not true. A lot of us pay tens of thousands of dollars every year to be in higher education. We don't expect any direct return for that. We're not investing our tuition into stocks -- at least I hope we're not -- and hoping they'll go up over the course of time. So, I say good on you, Nick! It's food for thought for the rest of us. At a certain point, you don't want to be spending too much on your investing. You want to be investing as much as you can. But in order to get to that place, most of us probably need some of a jump-start, and some expenditure way below the tuition that most of us are paying, in order to learn this critical and rewarding subject.

Okay. "On the subject of investing in oneself," Nick continues, "I've started a side project of creating a video game. If this is read on the podcast, you don't have to read this shameless bit, but it's a video game called Space Y: Rogue. The website is I feel as though investing more into the game would increase the chances of it becoming at least somewhat popular, and obviously increase the quality of the finished product. However, I just can't bring myself to do it, at least not with meaningful capital. I have a safety net, but I fear my money is of better use in the stock market. Something you said several months back as advice to entrepreneurs is that the market is great, but if you have an entrepreneurial spirit, then invest in yourself. Your idea, paraphrased, has stayed in my head, but I need a little more to pull the trigger or to back off completely. I was wondering if there are any statistics comparing the market to investing in oneself, or any rules of thumb, so to speak, that is Rule Breaker-y. Yours Foolishly, Nick Jackson."

Nick, short and sweet, here's how I'm thinking about this. Ultimately, you want to do both of these things. We want to have our cake and eat it, too, as we've often talked about on Rule Breaker Investing. I definitely want you to continue your investment, not just your education anymore, but now your investment history. I want you to save money and put that into stocks, because the odds of prospering that way are really, really good if you're investing Foolishly. Don't forget, the market is the wind at your back. It tends to rise around 10% or a year. Money you put in it now, you'll be really happy 20 and 50 years from now. Do the math. It's crazy, almost, to invest in anything else if you're not sufficiently apportioning funds toward the market. Very high expected rate of return with confidence relative to most things.

On the other hand, we hear small businesses fail -- I'm going to make these numbers up -- eight out of 10 of them just fail altogether. So if you're just purely doing the math, it probably makes sense for you to put those funds toward the stock market if you are not already sufficiently invested. Sounds like you're still at the outset, so that would be my tendency.

But how do we have our cake and eat it, too? Well, the answer is, I bet, since you're creating your own game, anybody who's doing their own side project or major project, you're investing your time in that. Time, as was once said in World of Warcraft, is money, friend. I bet you're already investing a huge amount of yourself into, in this case, your video game, or any of the projects, hobbies, or professional undertakings that anybody hearing this right now is doing. The value of your time, that is the most finite and valuable thing we have on this earth, is our time, and I bet you're already putting a lot of time toward it.

Now at the end, if I've left you on the horns of a dilemma and you still don't feel like you've been nudged either way, I would say split it down the middle. Take half of the money you're planning to invest and invest it, and take the other half the money that you were thinking to invest and put it toward your project. You don't have to make that permanent. You can just do that this month. And then next month, you can say which one's feeling better to you. A lot of is going to come down to whether your side project is going to work or not. I'm not just speaking to Nick here; I'm speaking to anybody who's thinking or investing toward something that is personally gratifying and/ or commercially viable. Those things are sometimes different things.

Nick, I hope that's given you some food for thought. For anybody else, this is a very common question. Where should I put my money? Where should I put my resources? If Jeff Bezos were on the show, he talks about the regret minimization framework. We've talked about that before. But here's the thought -- when you're 80 years old, look back right now at yourself, Nick Jackson. The 80-year-old Nick Jackson looks back at the one today and says, "How did I minimize the regret that I feel at the age of 80? Did I put it toward my game? Or did I put it toward the market?" So, as a much more mature version of yourself, try to minimize the regret you're going to feel then. Maybe that'll help you make the final decision.