Adult media mogul Hugh Hefner passed away yesterday at the ripe old age of 91, leaving behind a powerful marketing legacy for business owners and entrepreneurs to admire and learn from.

Hefner launched his iconic adult entertainment magazine, Playboy, in 1953, selling 50,000 copies thanks largely to a nude photo of Marilyn Monroe, which he purchased for $500, featured in the magazine's centerfold. Since then, he grew a business empire that developed into one of the top icon brands of the past six decades.

Hefner, who will be buried in a crypt next to Monroe, embodied three critical aspects necessary for branding and marketing success throughout his legendary career:

1. Distinguish your brand.

Launched during an era characterized by traditional values and sexual repression, Hefner conceptualized Playboy Magazine as a combination of literature and nude women, distinguishing the brand from both mainstream and pornography magazines of the time.

What helped to cement the Playboy brand as an intersection of sex and sophistication is the bunny logo. Rabbits are known for their mating habits, and naturally, Hefner decided to class it up with a tie. Rather than trying to blend in with other media companies, his deliberate branding decisions put Playboy in a class of its own.

2. Take risks.

Hefner's decision to feature Monroe in the first Playboy issue was the first of many big risks he took with his brand.

Those risks eventually lead to an arrest on obscenity charges in 1963 after he featured nude photos of Jayne Mansfield in the magazine, but the charges were dropped, and Hefner persevered, going on the found the Hugh M. Hefner Foundation to protect civil rights and civil liberties.

3. Know what you're fighting for.

Hefner built more than a brand; he pioneered a movement toward sexual liberty and free expression. To many, the Playboy brand symbolized a defiant rebuke of traditional values. That's what Hefner was fighting for.

For you as an entrepreneur, your branding and messaging must go beyond what you do. Your key audiences must understand why you do what you do. Customers need to connect with your brand on a deeper level to reach anything close to the marketing success and recognition Hefner earned for his brand.