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This Sitcom Character Would Make the Best Startup Founder

At the end of a long day, my wife and I like to plop down on the couch and unwind by watching a sitcom. There have been many revolutions in television but the 30-minute sitcom format – laugh track included – is still the best. And though part of the appeal is its brainlessness, I can never truly shut off mine. And so, as I watch and laugh, I can’t help but wonder: of all the sitcom characters who would make the best startup founder and CEO? This was the blog I was destined to write, as I’ve been doing research on this topic for 30 years.

Let me preface that a character only qualified if the show aired during my window of television watching which began in 1990 when I was seven years old and remains open until today. So if a show ended before 1990, it was disqualified. I needed to draw the line somewhere. Secondly, the character could not be an entrepreneur in the show. For example, Jay Pritchett built a successful closet empire on Modern Family, as such he was ineligible for this thought experiment.

So without further adieu, let me give my honorable mentions prior to naming the runner up and finally the champ:

Phoebe Buffay, Friends

Phoebe’s strongest quality is that she is naive. She was never told the truth about Santa Claus. To be a successful founder, you need to believe in the impossible, as more than 80% of startups fail. Additionally, Phoebe is musical (she plays the guitar), speaks multiple languages (French and Italian), and as a masseuse, she has strong hands and isn’t afraid of hard work. Like Jack Dorsey, another founder darling, Phoebe is eccentric and a bit, how you say, unorthodox- she practices New Age ideas, is a vegetarian, thinks Darwinism is “too easy”, and once had the spirit of an old woman enter her body.

Additionally, in many episodes Phoebe’s age changes and in other ones she alludes to a dark past that no one knows about, as well as connections to the criminal underworld (which could be viewed as a positive or negative, really). She already has one of the most critical factors nailed: the art of the founder myth making. Imagine her TedTalk!

Phoebe has dealt with the worst that life can throw at you – her mother committed suicide, her step-father went to prison, she was homeless, her sister used her name as an adult film star. Yet, not only does she continue to persevere, she shows a willingness to evolve. When Phoebe met Mike Hannigan she realized that she wanted to become a “soccer mom”, something nobody else would have imagined for her. That ability for re-invention is crucial for any startup.

My biggest concern with Phoebe is that she would need to find her Sheryl Sandberg – the seasoned, operating executive who could help keep the company stay on track, which would free Phoebe up to dabble with the next big thing. I worry with her lack of focus if she could ever grow a company to the size that would warrant the involvement of a Sandberg.

Will Smith, The Fresh Prince of Bel-Air

Will has many of the characteristics of a successful entrepreneur: he is charismatic and quick witted, he has a rich uncle, which could certainly help a friends and family round, he builds relationships with his staff, as he did with his butler, Geoffrey, and he has diverse life experiences having lived in both the hardened streets of West Philadelphia and the cushy confines of Bel-Air, which means he could relate to multiple audiences.

There were a few red flags, however. Will’s constant mocking and belittlement of Carlton could set the foundation for a toxic work environment. Even though the jokes are clearly in jest and the two have a brotherly bond that background might not be understood at scale and could, at the least, create a fraternity-like atmosphere or, at the worst, a hostile workplace. Also, I think Will would be ripe to be taken advantage of, which he showed himself capable of in the episode when his father returned and promised to take him on a cross-country drive in his big rig. I don’t blame Will for wanting to give his father another chance. But he blatantly ignored the advice of his trusted council, Uncle Phil, which makes me nervous that he could be blinded in the future and chase after something that would impact the company despite the protests of his executive team or board of directors.

And the runner up is…

Jerry Seinfeld, Seinfeld

Let’s spend a little time discussing some of Jerry’s traits and how I feel they’d help him successfully scale a startup.


Jerry is a standup comedian, which means he’s a natural entrepreneur who is not afraid of hustle. Also as a standup comedian trying to make it big, Jerry would most likely have had to tour at different comedy clubs across the country. This will give him some much needed perspective on America that he wouldn’t have otherwise seen as a lifelong New Yorker.


Seinfeld is one of the most commercially successful television shows of all time, grossing more than $3 billion since it went into syndication in 1995. Anyone who could create a show about nothing and make it a part of the American lexicon is a certifiable genius. The character Jerry on the show Seinfeld, along with George, came up with the idea for the show. Here is see some Henry Ford comps. He didn’t give his customers faster horses. He gave them nothing and they wanted more.


As a single person in his mid-30’s living in Manhattan, Jerry is connected. He has appeared on The Today Show (albeit with a questionably puffy shirt on… can you say trendsetter!) and The Tonight Show to name but a few. His friend, Elaine, worked for a big time publishing company, Kramer knows Bette Midler, and Jerry was friends with I’m Keith Hernandez. Feels like there’s a lot of potential funding and celebrity endorsements in that short list alone.

I should also note Jerry’s age. When the show began, Jerry (the actor, I am not sure the character) was 35-years-old. Though most VCs don’t like to fund startups led by people over 32, most successful startups are founded by someone in their early 40s.

While I’m noting things, I will also note that being located in New York City will certainly help Jerry. Silicon Alley has a strong reputation for innovation and, given the time that Seinfeld ran, Jerry could have gotten in and out of a startup before the dot com bubble broke.

Competitive, spiteful and petty

By all accounts Jerry was a successful comedian but he was very competitive against fellow comedian Kenny Bania. Yes, Jerry tried to mentor Kenny but once it actually helped improve his act, Jerry was furious. This pettiness will know doubt hurt Jerry in the long run but it is the type of swinging of sharp elbows that could help get the company off the ground.


In a similar vein, an argument could be made that Jerry is a psychopath. He once broke up with a girl because he didn’t want to give up making a voice. He sours on people quickly. He has a very close circle of friends but everyone else is essentially disposable. Unfortunately, this trait is all too common in successful startups. Don’t agree then check out this article. I feel some similarities here between Jerry and Theranos founder Elizabeth Holmes.

Strong stomach

If you don’t think Jerry has the stomach to be ruthless, remember the fact that he didn’t vomit from June 29,1980 until November 18, 1993. That’s a 13 year run, which is pretty impressive and shows he doesn’t get too sick (won’t miss work) and doesn’t get squeamish (this didn’t happen until the fifth season, which means he did a lot of rotten things to people in the first four seasons that didn’t make him puke).

Detail oriented

Who remembers the exact date of the last time they vomited? A detail oriented person… or a psychopath. Either way, my point is being made.

The biggest question mark for Jerry’s candidacy comes not from him but what your definition of a successful startup is. Based on all I’ve seen in the industry, do I think a startup founded by a person like Jerry could get funding, build a product, deliver it to the market, and create value along the way? Yes, I do.

Would I want to work there? Will the company ever make the Fortune 500? Will it build a lasting legacy? I am not sure about those things based on Jerry’s character, which knocked him down to the runner up spot.

Actually, when I first thought of this blog, I had Jerry as the winner but the more I thought about what makes a great startup founder and CEO I realized it goes beyond just bulldozing an idea to creation. Maybe I am sappy. But if I am going to invest my time in a hypothetical, nonsensical thought experiment then I want the winner to reflect the world I want not the world we’re currently in.

So, as a result, the winner is…

Leslie Knope, Parks and Recreation

Like Zappos’s Tony Hsieh, Leslie would have built a company around culture. Her strengths are obvious.


If you are a friend of Leslie Knope then you have a friend for life. Whenever anyone from her team was in trouble, Leslie was there for her. She even once stood in a Jello-wrestling pit to defend the reputation of Anne Perkins. And my how she mentored her team and helped them reach levels they never thought possible. Watch the series finale. Look at where this ragtag cast of characters from central Indiana ended up. That’s the magic of Leslie Knope.

Makes people feel special

We are living in the age of the customer. Any good subscription business knows that you can’t just win new customers. You must retain them. You need to do that through a strong customer success program and you need to make them feel special. No one makes people feel more special than Leslie. I won’t go into too much detail but the wedding gift she gives Ron is tailored made for him. It is something he will always remember. If Leslie challenged that energy toward her customers she would create an army of brand ambassadors.


She was well known for having a binder for any and all situations. The proposal she submitted on the Pawnee River clean up reached legendary status within the Department of the Interior. Heck, she even had a binder the time her and April picked up trash. She would be prepared for any investor or customer pitch as well as future board meetings.

Experienced orator

Part of the job of a CEO is standing on center stage and delivering the vision of the company or dealing with sceptical reporters or analysts. Leslie has experience holding public forums and had dealt with every type of person, snide remark, and Monday morning quarterbacking. Yet she continually finds a way to break through the noise and accomplish things.

Master of the rebrand

Startups iterate. That’s the nice way of saying they’re making it up as they go along and need to reinvent themselves. Startups are rebranding on the regular. No one is a master of the rebrand better than Leslie Knope. Need I say more then TDazzle!

Playing the long game

In the show, Leslie starts as a mid-level employee in the parks and recreation department of Pawnee, Indiana, yet has her eyes set on something higher – President of the United States. An ambitious goal that, based on flash forwards in the final season, may actually happen. She is not afraid to dream big but she’s also not afraid to eat the proverbial sh*t it takes to get it done. Her vision mixed with her tactical ability to execute is the recipe for a strong entrepreneur.

Additionally, Leslie showed that she loved and accelled at the tactical but that as she evolved in her career and her leadership grew, she was able to deligate those responsibilities to others and allowed them to flourish. This wasn’t always easy, like when Leslie tried to bring a retiring hot stew chef out of retirement. But she always learns.


At first I was going to knock Leslie for being from Pawnee, Indiana. If Entertainment 720, with strong celebrity endorsements from Roy Hibbert and Detlef Schrempf, couldn’t make it big out of Pawnee, Indiana, I felt like location was a strike against Leslie. But then I realized a few things: one Entertainment 720 was being run by two young men who thought they knew everything. That is certainly a combination that has led to more startups failing than any other. Amy Poehler, as Leslie, is 37 years old in the first season of the show, even closer to that sweet spot for successful founders and startups founded by women also generate more revenue.

So I don’t think 720 Entertainment’s failures have any bearing on another company being successful in Pawnee. With such connections to the government, Leslie could also help build a strong startup ecosystem in Pawnee, perhaps transforming it into the Boulder of the midwest.

Being an outsider forces you to think differently and not simply live in the echo chamber of Silicon Valley. But let’s also remember how connected Leslie is. She knows Joe Biden and his Royal Excellence Lord Edgar Darby Covington is the 14th Earl of Cornwall-Upon-Thames and the 29th Baron of Hertfordshire. Not to mention the aforementioned Detlef Schrempf.

Leslie is not without her flaws and I feel like her biggest one is that she doesn’t move fast enough. The show implies that she held her mid-level position for six years. That patience and perseverance are to be applauded. However, in the startup game, if you wait that long to make a move, your funding will dry up and your investors will move on.

Similarly, Leslie always puts a positive spin on failure – “people caring loudly at me” – and doesn’t listen to what others want, shaping reality into her own vision. Again, this can be a positive at times but at other times, you have to get to no quickly and move on.

All of that being said, I would invest in Leslie over any other sitcom character. She has the vision, drive, and human decency to start something truly special.

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