The intent with this chart was obviously to show that Big Dick's company is doing well. Which is fine, but here's the thing, and I'm going to plug in some real numbers to make this explanation less abstract: say Pope's portfolio was worth $100,000 at the beginning of the first year, just to use a nice round number. That would mean that his Casablancas stock was worth $10,000 (10\% of the total value, according to the chart). Say also that the total value of his portfolio grew 50\% over that year (an astronomical rate of return for an equity portfolio even in a bull market, but he would have to do around that well at a minimum for his retirement plans to be significantly affected). So at the beginning of the next year, his portfolio would have been worth $150,000. Now, for his Casablancas stock to encompass 45\% of the total value of the portfolio, it would have to have been worth $67,500, which would mean the value of the stock increased 575\% in a single year. For a reasonably-well-established company -- as I assume Casablancas is, given Big Dick's already immense implied wealth -- that rate of growth is completely preposterous. So Pope must have taken a lot of money out of T-Bills and blue-chips and other more secure investments on the chart to buy more of the Casablancas stock, which is the exact opposite of conservative investing and not what someone close to retirement should do at all. Of course, if he's an officer of the company, he might have had some stock options that matured in that year, but regardless, he should have managed his portfolio (i.e. sold off a lot of stock) to keep a reasonable amount of diversification, which would have locked in a lot of the profit that he's going to lose due to events late in the episode. He must really not have wanted to pay some snot-nosed rich kid a cash prize.