Enterprising Investor vs Defensive Investor

I was talking to my brother this morning regarding property investment. I realised that both of us are two different types of investors. I remembered reading Benjamin Graham's "The Intelligent Investor". In it, he mentioned the two types of investors, the defensive investor and the enterprising investor.

I am an Enterprising investor while he is a Defensive investor. How did I find out?

My brother bought his current 3-bedroom with PES unit at less than $700,000 five years ago. At current market price, he can sell it for $1.2 million. There is a development, going to TOP soon near his area. A seller was asking $1.2 million for a mid-high floor 4-bedroom unit. Therefore, I suggested that he sells his current one to upgrade to the 4-bedroom unit and at the same time cash out the profit. His only reply was, "Live within your means. I would have to take up more loan if I were to buy now." He was contented with his current lifestyle. He will only start investing when he has saved enough for a second property. This is an example of a defensive investor.

What will you do if you were him? To sell and change to the 4-bedroom unit or to stay put in the current one and save enough to buy a second property?

Here's another example of a defensive investor. A ex-colleague of mine bought a new condo to move in and will be renting out her HDB flat. Her family has been staying in the HDB flat for more than 15 years. She bought the condo after she made sure that she has enough to service this current home as she has already fully paid her HDB flat.

As for me, I am an enterprising investor. I have downgraded twice, first from an EC to HDB 4 room resale flat, bought an investment condo and rented it out during the financial crisis, sold it off a year later, after the recession is over. I bought a terrace house with the intention to stay, but the profit made is too tempting to hold on to it. So this is the second time. I downgraded from a terrace to a condo. In the process, I have cashed out a handsome amount of profit and of course my outstanding loan is a few times higher than my brother's. His current outstanding loan may be at around $200,000 while mine is about $1 million.

So what kind of an investor are you? Have a word or two in the comments please.

Cheers.