Not-so-long ago, the post-playing career of a professional athlete entailed doing one of three things: becoming a coach, becoming a commentator or opening up a used car dealership.

Today's athletes want more -- a lot more -- and they aren't waiting to formulate a game plan for what comes next.

"I think one of the great transitions among athletes in the last decade is the emergence of entrepreneurship becoming a larger and more important part of the mindset of the modern day player," says Gary Vaynerchuk, co-founder of sports agency VaynerSports. "They have shifted their focus from what they can buy with this money to what they can build with this money. How can they turn each dollar into $10 and each $10 into $100."

Says Dave Meltzer, CEO of Sports 1 Marketing and host of The Playbook podcast. "These athletes are already preparing themselves for life after sports, building brands and giving back to communities and groups -- all of which are vitally important to long-term success."

Taking into account tangibles such as money earned with game-changing contracts and endorsement deals, as well as intangibles such as personal brand building, appetite for risk and, well, just the flat-out coolness of their business pursuits, we've come up with a ranked list of the 40 most entrepreneurial athletes of the year, and 30 legends who paved the way.

"Entrepreneurship is an incredibly positive progression for the sports industry and an important one to recognize," Vaynerchuk says. "As someone who has entrepreneurship and sports at the center of my life and interests, I couldn't be more proud to be a part of it."