So just how did Blaine get so rich? Here's the back story...
How Wes found out about Blaine's money
In his position as head of the Warbler council, Wes Montgomery felt that he was responsible not just for his choir when they were singing, but throughout their entire life at Dalton Academy. As a result, he would often appear unannounced at the most inconvenient moment if he felt that there was a need to check up on someone. On that evening, it was Blaine that was giving him cause for concern. Although his voice had been flawless as usual, and he had once again been making those secret smiles at the new kid, Kurt Hummel, Wes had seen something else. A preoccupation and a smidgen of guilt. As was usual, Blaine had seen Kurt off on his journey back to Lima, whilst he had made his way to the dorm room that was his home for most of the week.
When he arrived at the door Wes knocked and entered without waiting, as was his style when he had suspicions. In a couple of instances, it had resulted in him seeing things he had no desire to see. On this occasion the first thing he saw was the large pile of dollar bills on the bed. The large pile of $50 bills. Where had he got that money from, and why was he keeping it in his room? These were questions that Blaine would have to answer before Wes left the room.
His answer intrigued and appalled Wes at the same time. He knew that the boy's parents were not the best in the world, but he wasn't sure he could condone such blatant theft. Worse still, if he left the cash lying around, then someone less honest than himself might help themselves to some of it, or one of the teaching staff might find it and raise questions with the Andersons. He could only give Blaine advice, which amounted to firstly moving the cash to a bank account, and secondly, making sure he and the accountant covered their tracks very well.
It was several weeks later, just after Kurt had returned to McKinley, that Blaine came to him and asked him what he knew about investments. He had amassed a significant sum of money and he wanted to do more with it than just leave it sitting in the bank where it earned little interest in the current climate. Wes knew little about the world of stocks and shares. He did know something about investing in new technologies or ideas however. It was how his father made his money. Although it was risky, if you chose the right idea, then their was a fortune to be made. As it happened, Wes knew someone who was looking for an investor to help him develop a concept - a fellow senior at Dalton, who was a bit of a genius with mobile technology. He was starting a business making apps for smart phones, which he believed to be the future. His ideas were excellent, he just needed a cash boost to get things going.
So he had introduced Blaine to James. Left them to it after that. Had heard nothing else about it until about a week before Blaine had been due to marry Kurt, when his old friend had finally revealed the truth, desperate to share his good fortune with someone he could trust to keep quiet.
A week after Wes had set up that meeting, Blaine had given James a cheque for $5000, the full amount of cash he required to get his new firm up and running. In return, James had agreed to give half of any money he made from it back to Blaine. By his first Christmas at McKinley, Blaine had his $5000 back. A week before Kurt's graduation, he had doubled his money - at that point, James had asked for a further investment to allow him to expand the range of apps he was developing. So $5000 went back in, on the same terms as before. All through Blaine's senior year, he would receive an income from James. This time, the money came faster than ever. In December, the sum of $15000 was deposited in Blaine's account - at first he thought it was an error, but James confirmed that sales were picking up - a rush before the holidays. When the next month saw a deposit of the same size, it seemed that it was no fluke.
The amounts continued to grow, and by the time Blaine went to LA for Nationals, the sums of money were starting to seem almost obscene. If things carried on at the rate they were, then paying for college would be easy. It was just after the New Directions loss was announced that Blaine received a message from James, asking him to meet him urgently. It could only mean one thing in his opinion. The good times were over, and the income was going to dry up. Still he had had a good run, and he had a nice nest egg tucked away in the bank.
When James finished telling him what had happened over a cup of coffee, Blaine was in shock. This was beyond his wildest dreams - it was a fairy tale. His small investment had taken off in a big way. He would have enough cash behind him to give himself and Kurt the life that they deserved. He had decided not to tell him until the cash was transferred and the deal settled. By the time that happened, things had taken a turn in New York. He was getting married in weeks, and Kurt thought they were pretty broke. He was going to tell him they were the exact opposite, but he had seemed so taken with the notion of the wedding that they made together that he didn't have the heart to say there was no need. It could be his wedding present to his one true love.
The new loft, that had been a lucky chance. That he had been home, alone and found out that it was for sale. That he had seen the potential and managed to develop it right in front of Kurt's eyes without him finding out. Of course, there was a risk that Kurt might throw it all back in his face. He was willing to take it. He was pretty sure that even if he was livid, he'd forget all about it when he saw his dream kitchen. Wes was the only person he told about it, because without his first introduction, none of it could have happened….
