To prognosticate the future on the Internet timescale is a risky venture even looking year to year. When one understands the fundamentals of what is changing, per rare individuals like Don Tapscott, it is possible been right on the target even over decades. In his 20th anniversary edition of The Digital Economy (McGraw-Hill, 2014), we can take a look back at the bright glimpses into what was and look forward at what could be.