Season six of Jerry Seinfeld's online series Comedians in Cars Getting Coffee revved up last night starring a 1964 Aston Martin and an equally chic Seinfeld co-star, Julia Louis-Dreyfus. With its plethora of A-list comedians and airtight production value, Seinfeld's latest project shows he can remain relevant, even with viewers who were barely talking when his first TV show premiered in 1989. 

Following Seinfeld's success, the 61-year-old comedian could easily fade into retirement. The Independent estimated in 2013 that he's earned more than $3 billion in syndication royalties since the sitcom's finale in 1998. He will also pocket a portion of the reported $130 million to $180 million Hulu recently paid for all nine seasons of the TV show.

But as actor James Spader recently told the New York Times, Seinfeld "can't resist curiosity and enthusiasm for something new." Here are four lessons for entrepreneurs thinking about a successful second act from Seinfeld's journey from an average guy in a show about nothing, to a billionaire with a show about antique cars and the biggest names in comedy.

1. Be persistent in the face of 'No.'

You would think any project stamped with the name Jerry Seinfeld would have partners and sponsors lined up around the block. Not so with Comedians in Cars. Seinfeld has said in multiple interviews that he was turned down by just about every TV network he could think of, before finally finding a home for the show on Sony's Crackle network. He also tried to land a partnership with Starbucks, but said Howard Shultz didn't see the connection.

Even if you've already proven yourself, finding the right partners for your next project can feel like starting over. It can require a lot of legwork and negotiation, especially if others don't understand your vision. But sometimes it's worth knocking on a hundred doors to find the right teammates. Seinfeld eventually landed an Acura sponsorship that allows him to have control of the advertising (even writing and directing the ads himself), as well as the freedom to feature cars from other manufacturers.

2. Embrace your passion.

After proving himself through decades of standup and nine widely successful sitcom seasons, Seinfeld had the freedom to make Comedians in Cars in his own image. His stamp is all over the show, even in the quirky Acura ads he wrote and directed--and for which he won an honorary Clio award.

The show's premise is built on things Seinfeld loves--antique cars and talking to other comedians. He ignored advice that online viewers won't watch videos longer than a few minutes, and instead created 15 to 20 minute episodes (the episode with Louis C.K. is 22 minutes). Though these could be reasons he struggled landing partners, Seinfeld stuck to his guns because he had a vision and didn't want to stop until he found colleagues that supported him.

While experience doesn't serve as a hall pass for staunch single mindedness, it does provide an entrepreneur with a platform on which to stand and declare his vision. Like Seinfeld, if you have ample experience under your belt, that'll serve you. Not only have you been through the ringer, you likely have the wherewithal to evaluate advice and determine if it will work for your purposes.

3. Don't take yourself too seriously. 

Though the comedian has a reputation for being pompous, he is still widely loved by mainstream Americans. In the years between Seinfeld and Comedians in Cars he maintained his relevance with appearances on The Tonight Show, The Late Show and Louie, where he has no problem making fun of himself.

As an experienced entrepreneur, it's important to make an effort to connect with your less-seasoned workers. Accessibility builds trust and creates a flow of ideas, so find some commonalities of everyday life with your employees. The last thing you want is to stifle creative expression by intimidating others. They'll respect and trust you more if you show them your success hasn't made you a robot.

4. Follow the data. 

Seinfeld describes himself as having an "unsentimental, mathematical, '3-D modeling' approach to looking at showbiz careers." Even though he didn't come up in a digital age, he is embracing the wonders of data, so he knows excactly who watches Comedians in Cars, and where they watch it (25-34 year olds, on viewing devices like Apple TV and Roku).

It's easy to run a business based on assumptions of how others will consume it. Whether you're following your own vision or the advice of others, it's important to follow the data to see what's happening in the real world.

Published on: Jun 4, 2015