DHH just recently learned that in comparison to his peers, his family was actually quite poor growing up, but thanks to his mom's efforts, he's not realized it till this day.
Now that he is able to afford to spoil his kids with abundance of things, he does not think that is actually a good idea, but not for the reasons you might think. DHH lets his kids have any toys they want, but he is also teaching them about the value of passion, as opposed to the value of a reward.
The society tends to teach kids that had work is important, even if you do not like what you work on, all in pursuit of material goods. David says that all the toys in the world are not going to make a happy kid, at least not in the long-run, but working on something that truly matters will.