Chasing The Great Pumpkin: Founders and Defying Doubters

Aspiring to greatness usually serves as a tip-off to onlookers that you’re a loser, a wannabe. Which is all the more reason to aspire for greatness.

Take it from someone who has tried and failed to achieve greatness several times. A mobile phone kiosk that failed to become the next major retail giant. A legal case management system that never took off. And now I’m looking at creating a new project management tool. That plan doesn’t sound like the stuff of Alexander the Great. But it’s still greatness, and it’s almost as important for Joe Schmoes like me to propose new project management tools as it is for Elon Musk to propose colonizing Mars.

My odds of success are slim at the moment, as are Musk’s. If you’re a startup founder, you’ve had ideas that probably won’t pan out. But it’s essential that we, as a group, have these ideas. Innovation is impossible without unqualified people having fantastical ideas. Society needs people like us.

Doubters Gonna Doubt

It’s Halloween, so I’ll bust out a familiar anecdote: Linus van Pelt, Charlie Brown’s best friend, occupies a pumpkin patch every year, rather than trick-or-treating. His goal is to greet the Great Pumpkin, a mythological gourd that brings gifts to faithful children on Halloween night.

Linus is laughed at by the neighborhood children for his beliefs. Why shouldn’t he be? He’s turning down guaranteed candy for an unlikely payoff. It’s a plan as stupid as dropping out of Harvard and launching a website for friends to post what they’re doing at the moment, with no revenue plan.

Those pursuing the startup lifestyle should expect some judgement, if not laughter. Family gatherings, hanging out with buddies at the bar…someone will ask why you don’t just settle down and get a “real” job, especially if you have a business or marketing degree. “Why do you keep blowing money on these longshots?” they ask. “Do you know how much you can make with a salaried position?”

Alex Frommeyer, the founder of Beam Dental, has been there. He helped develop a toothbrush that collects data on the user’s oral hygiene, in order to generate better dental insurance prices. That sort of forward thinking didn’t impress his family.

“To this day I’m still dealing with it. The ‘so when are you going to get a real job?’” he says, winking and making a nudging motion with his arm for comical effect. His business has its own floor in a fashionable neighborhood in Columbus (and a ping-pong table). Maybe it still seems too much like a fantasy for them to take seriously.

Ideals Rise Above Disbelief

This has happened to Elon Musk. Surely, despite his past successes, someone has asked why he doesn’t focus on improving life on Earth before looking to Mars. But at least people understand the idealism behind such a lofty idea. It’s tougher to explain why the world needs another project management tool.

Linus has a great quote during It’s The Great Pumpkin Charlie Brown, which helps justify the purpose of “small fry” entrepreneurs, such as myself. When Charlie Brown accusingly asks when he’s going to stop believing in “something that isn’t true,” he responds:

When you stop believing in that fellow with a red suit and the white beard who goes ‘ho ho ho.’”

For the sake of the children watching the show, it’s a humorous aside (“That’s a ridiculous comparison…obviously Santa Claus is real and the Great Pumpkin is not”) but for the adults watching the show, it should suggest a more philosophical truth. Why is the notion of a magic, flying pumpkin ridiculous when compared to a man who flies the skies with a team of reindeer? Why should a flying car sound ridiculous when planes exist? Why shouldn’t colonies on Mars exist when the International Space Station allows life in orbit?

No One Can Follow Your Dreams But You

More importantly, the Great Pumpkin teaches the importance of black sheep to the startup world. Linus seems silly for believing in a magic pumpkin when the similar Santa Claus already exists. Similarly, many have warily asked me why I would contemplate a new project management tool when things like Basecamp, Resource Guru and Podio already exist. They exist but they don’t fill all of my needs. I feel there’s room for an improved product, an improved idea.

The listed examples are Santa Clauses. Pretty good. But I need a Great Pumpkin. A product management tool that’s so different from its predecessors that it’s not even called a “product management tool” anymore.

Those are big words and that’s what aspiring to greatness sounds like. It’s the kind of stuff that’s likely to get me laughed out of the room when I introduce the idea to people comfortable with the status quo. It’s as bold as proposing to take MySpace and then make it better, and somehow find money in it.

Wil Schroter, the founder of, knows something about the process. He’s founded a series of successful startups, and now he runs a site that specializes in helping founders. He understands the anxiety of defying convention. But now, having succeeded, he feels the opposite: the fear of not doing something different. The fear of blending in.

“At this point I’ve talked to thousands and thousands of founders, and having gone through this journey a handful of times myself, none of us knows if it’s going to work until one day it does,” he said of his first few startups. “My fears now are much different than they used to be. Right now it’s a fear of not being able to make enough impact.”

The Scariest Doubt Is Self

Here’s the bad news: Aspiring to greatness, at least in the sense of startups, rarely pans out. Less than 8 percent will make it to the three-year mark. Linus himself falls asleep in the field and is carried, shivering, to his bed. He has no candy in the morning, unless Lucy is feeling generous (which is rare). Circumstances will force the majority of those with grand ideas to quit early.

So it probably still seems pretty stupid to keep on pursuing greatness, huh?

Twice I’ve thrown out examples of dumb things someone could do, with regard to launching a social media site. These are the exact things that Mark Zuckerberg did. Now social media is the most influential form of communication on Earth, and Facebook is worth nearly $50 billion.

He could have gotten a job as a computer programmer, and he’d probably be living well today. Instead, he played it stupid and changed that world. He went from relative nobody to the guy. A wannabe to being.

That’s why founders like you and I, and Linus, keep on chasing our Great Pumpkins. People will only call you a wannabe until you actually are. If the worst occurs, it was better to be a wannabe than a could-have-been.

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