I think you can look at entrepreneur motivational in two basic ways: 

1. Paradoxical Laziness 

A lot of entrepreneurs don’t want to work that hard. Tech and “hacking” are particularly appealing to these people.

“If I can find a way to work smarter… then I can beat the people working harder.” 

If you’ve ever had these types of thoughts, then you’ve been there.

The entrepreneur motivated this way will disrupt lumbering, innovative status-quo industries. 

Digital arbitrage businesses (lead gen, affiliate stuff, crypto etc) are very seductive to entrepreneurs with this “laziness motivation”. They’ll often – paradoxically – work 16 hours a day so they can make money while the sleep. But it’s important that the actual money is made while they sleep. 

They tend to be creative, have wide lateral curiosities and interests and have difficulty sticking to things long term. The stick-to-things issue is a double-edged sword: it makes follow through tough, but the strong preference for novelty means that these entrepreneurs enjoy being on the absolute bleeding edge or tech (or whatever!). And it’s always in that Wild West where arbitrage opportunities lie.

2. Old-fashioned Industriousness

These are the entrepreneurs who’ve realized that there is no traffic on the extra mile. They’ve figured out that you can make money by doing things no one else is willing – or courageous enough – to do. 

They tend to build businesses that require brute-force elbow grease to win at. Or at least to get started. They often perfect agency/service business models where consistently overdelivering on promises guarantees success. 

Delayed gratification is something that feels good. These people are investing their time, energy and money because they aren’t afraid of hard work. They believe that opportunity lies on the other side of hustle.  

The downside of industriously motivated entrepreneurs is that they can often develop myopia or tunnel vision. Exponential opportunities are hard to spot, when you’re deeply committed to a “extra-mile” grind.

What’s important for these entrepreneurs to keep in mind is that the same personality trait – conscientiousness – that makes them such a #hustlemode hard worker… is also exactly what propels people through linear high prestige career tracks like law and medicine. All the entrepreneurs reading this will see why this isn’t necessarily a good thing.

These entrepreneurs find comfort in predictable, bounded input/output opportunities… and have to push themselves to take risks and pursue bold strategies for big growth.

The third option: Becoming an integrated entrepreneur 

The entrepreneurial superhuman puts these two kinds of entrepreneurial drive together.  They figure out the middle path, an embodiment of both industriousness AND clever shortcuts. 

You can see this played out in the now-fabled tale of AirBNB’s cofounders schlepping around San Francisco, snapping photos of apartments to manually jumpstart the site’s inventory and break out of a chicken/egg stuck-ness. 

The best business models always have something devilishly clever; a hacked arbitrage, a disruptive shortcut or a way to totally nix the competition. And the best founders do well when they find one of these much smarter ideas, and then work devilishly hard to make it happen. 

Turns out, all the old axioms are true: Work smarter, not harder. There’s no traffic on the extra mile. Product is everything. Do things no one else is willing to do. 

It all works. And it works best when you do it all. 

As an entrepreneur, the takeaway from this article should be self awareness. Get clear on how – and where – in your business you’re showing up with one and not the other kind of motivational drive. Commit to pushing yourself to balance out your drive with that middle path that encompasses both.