For some time after Jay left Rome, he was lost, unsure of his direction. Using his talents as a mercenary, he started a small business out of the warehouse Talia had gifted him, going by word of mouth. He racked up a few dozen hits in Gotham, and attracted the attention of Thomas Elliot, M.D. Tommy, or as he introduced himself to Jason, Hush, came to the warehouse, asking for a simple answer.
Is Batman’s identity really Bruce Wayne?
Of course, Jason was able to answer that with ease, and did so. He saw in Tommy the same hatred, the same pain, the same rage that Jason felt. Hush had his direction; ruin Bruce’s life.
They worked out a deal. Fifteen million, cash, for proof. 
The deal was completed within a week, and Jason shut down his warehouse killer-for-hire operation soon after. He poured the money into construction a new company, Redstone Security. It focused on building a network of ex-soldiers, analysts, scientists, and developers, all working towards advances in technology, security, and weaponry. Simply put, he created a private army for hire, contracting with the government and foreign entities. The Research and Development department focused on engineering gear for his new persona-the Red Hood. His new direction of saving Gotham, one bullet at a time, was starting. With profits from Redstone, he purchased the Complex, cementing his presence in Gotham.
He didn’t see Tommy again for many years, but that’s a story for another time.