The idea of being an entrepreneur has been made to look as sexy as being a designer. Media — big and small — have given the world an outsized presence in a world built for the opposite. Quitting a job — or never starting one — to build something from scratch is glorified in ways that make the lows appear obvious, avoidable and passing while the highs are private planes and IPOs.

So when things are sexy the wave invites everyone along for the ride. The few that thrive are celebrated in larger than life ways. The ones that find a home stay are under the radar. Some turn their ‘failure’ into a promotion they would have never experienced without the education the entrepreneurial world provides.

However, there are lots of folks who stay too long. The bitterness and frustration become amplified by the supposed success of the winners. The ‘failures’ feel like failures.

Honestly, I don’t pretend to know what success looks like to anyone other than myself. But I know that the most important word in all of these conversations is monetization.

The ability to make a profit out of an idea or product or community or concept or personality is not a skill that everyone has. And not everyone with that skill uses it for good. But ‘making a dollar out of 15¢’ is the true test as to whether becoming an entrepreneur will pay off.

Over the years I’ve noticed two types of people who succeed in the wild. The Hustler and the Insider.

The Hustler

We all know the person who’s ‘always trying to sell you something’ and we roll our eyes when they enter the room. Whether he’s selling you socks and off-brand cologne at the barber shop or she’s upselling you the penthouse overlooking the park, you know they are going to get a deal done because they know they are going to get a deal done.

Sales people are one notch above lawyers in the totem pole of people you want hang around with — creatives are only notch above that — and we all know why. Watch the origin stories of Gary Vee and Christian Dawkins. Watch their families explain how they’ve been hustling all of their life. Then realize they’re even using their story to sell you on something else, while they promise you they that they are not.

Sales people can’t turn off the hustle. Lawyers debate everything (side note: pickup basketball with more than two lawyers take three times longer). Creatives judge everything — including every font used on every menu in every restaurant they’ve ever entered.

But the that ability to make money is fundamental to operating a successful business. Left unchecked and you get what amounts to the greed that amplified the inequities that get amplified by the -isms of race, sex, able, class. Yet, harnessed with healthy goals, self-awareness and a love for humanity, you get someone that will get your product into every hand that needs it.

Somebody at the barbershop needed socks that day.

That hustler mentality in an entrepreneur is where you see many of the success stories. They see monetary opportunities in every interaction they encounter. In the wild it’s their outsized passion for what they are selling that intrigues and amazes while annoys and grates. The love of their widget is intertwined with the need to sell, so you believe that they believe.

The t-shirt above was made by self-titled ‘entrepreDoer’ Brandon Edwards. He quit his job in healthcare (pre-COVID) to sell t-shirts. No sponsors. No experience. No problem. But he lives on social media and at the print shop because he believes.

In corporate sales jobs, that belief is watered down by their commision or paycheck. Are they selling you something because they truly believe or because they are simply selling you something? You’ll see this conflict if you’re in an industry long enough to watch the hustler go from company A to B to C while extolling the unbelievable benefits of each new widget along the way. The show doesn’t change even if the widget does.

But in the wild, the hustler dominates. VC’s bet on them repeatedly. Employees follow them from start-up to start-up. The media tells their stories — success, failure, success — until the clicks stop.

Monetization is in their DNA, so be careful when people expect you to fall into their footsteps. A thousand ‘No’s for one ‘Yes’ is their cup of tea.

The Insider

The less heralded entrepreneurial success has a much different path. The individual who stumbles on a process or product or personality that can be monetized because they live on the inside of a machine that hasn’t prioritized that widget, brings along a ton of knowledge related to giving that widget life. Zuckerberg was a Harvard widget. Away Travel was a Warby Parker widget.

Founders born out of other businesses have the information needed to build the next business. They can find the white space and can build teams similar to the success they just left.

How many advertising agencies were started by someone who worked at an advertising agency?

All of them (sans the agencies started by hustlers).

The intricate knowledge — pitfalls and opportunities — that insiders gain from living the business gives them the vision to see opportunities based on immediate need — George Lucas with Industrial Light and Magic — or industry neglect — Andrew Wyatt with Cala.

The insider is rarely the sexy choice. The insider typically needs a lot of faith or a goods sales ally to go sift through the ‘No’s to find the ‘Yes’. The insider is rarely there for the show. An insider is there for the widget.

Everlane founder Michael Preysman founded an apparel company after working in private equity for three years. He studied the widget of apparel but his insider widget was knowing how to raise the startup capital. He’s not sales guy. He believes in what he’s making but he’s not here to convince you.

The insider knows that there’s money around the corner because their previous industry existence showed them the map. An insider doesn’t head to the outside without a monetization strategy. What’s the point?

Make Money Money

A combination of these two worlds are often what you see in successful entrepreneurs. These two assets at full power are what you get with Jeff Bezos and Elon Musk and the children of celebrity.

The measure of success in the wild, however, shouldn’t be limited to becoming a trillionaire or launching cars into space. Those that venture into the wild may return to the relative comfort of an existing business with a host of new skills and appreciation for the possibilities they were blind to before.

The hustler and the insider won’t always find ‘success’ in the wild, but their exponential growth will become obvious to those paying attention. Being an entrepreneur is just another job that you could get fired from. You’ll just need to find another job with those new found skills.

But if you find yourself looking into the wild, be sure you have a healthy combination of hustler and insider. The perfect hustler won’t be outworked. The perfect insider knows everything and everybody. And both know where the pot of gold can be found.

Good things.