A couple of years ago - just as I was preparing to move from WooThemes into my next adventure - I was discussing assets, investments and wealth with someone that was already much further along in their journey.

At one stage he was telling me about how he finds and buys old, vintage Ferraris for more than a quarter million dollars a pop, before then restoring them and selling them for sometimes double the purchase price. My young, inexperienced mind saw only red flags with this and my question about how risky these kinds of purchases and projects were, represented my opinion accurately.

The individual's answer though surprised me. They said that it was possible and not necessarily risky to invest in any asset class, whether that asset is a startup you are founding, a regulated financial instrument or more exotic options like vintage Ferrari's, fine wine or art. The only requirement was that one understands that asset class intimately, because it was that intimacy that would help one navigate the good and bad opportunities.

Prior to this, the idea of intimacy isn't something that I would've related to assets, investments, wealth or any of the business ventures that I have worked on. The idea has stuck with me though, because I'm naturally drawn to deeper, more intimate connections in my personal life.

That said, I've not always been diligent in applying the idea to my own decisions and even when I have, it's also not been a guarantee of success. I've made quite a few investments post-WooThemes that have gone to zero; some of those in spaces with which I had great intimacy.

In the same breath though, just as I exited Woo, my wife and I bought our current house in a new, mostly unknown city. Today, 6 years later, this is now our intimate place and the best decision we could've made for our family.

And shortly after that move, I also made the decision to work on Conversio (which emerged from the ashes of having to painfully shut down the idea that came just after WooThemes).

When I reflect on these decisions and evaluate my investment decisions, there is a guiding hypothesis that comes to light: the better decisions tend to be those where I didn't venture too far beyond myself or our family. Whenever I stuck closer to the ideas that I had, my nature or the way I work, it seemed to pay better dividends.

Similarly, having an understanding of our family's needs and a strong relationship with my wife, helped us turn a really big decision and move into a very successful outcome. I also believe that being so settled into our home life today is what gives us the kind of foundation to make truly life-first decisions. Basically the sustainable gift that keeps on giving.

If we want, there is an intimacy that we can nurture with ourselves that likely transcends any other kind of learning that we can do. That kind of Return On Me that can only come from our intimate knowledge of our most valuable asset: ourselves, in this life, with this body, in this moment and surrounded by the people that really matter.

As much as we can study any subject extensively and do our 10 000 hours en route to mastery, it's a risky endeavour when we can't be intimate and comfortable with ourselves first.