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.

Smart entrepreneurs spend a lot of time thinking about product market fit. Turning strangers into customers is pretty much everything, after all.

That’s why entrepreneurs put a ton of energy into crafting the marketing narratives that will persuade people to buy their thing. 

They study these arts and sciences to do so: 

  • Product Design.
  • Marketing. 
  • Sales.
  • Persuasion. 

Founders are wise to learn about—and ruminate upon—this stuff. If you want to win in business you need to be obsessed with getting these things right. 

There’s one other thing entrepreneurs need to consider though. There’s one thing missing from that list. And most entrepreneurs never think about it at all. But when they do, it revolutionizes their product’s ability to sell itself. Like magic.   

Do you ever wonder why some products seem to magnetically attract customers, fly off the shelves and generate fanatic word-of-mouth? 

And vice versa: Have you ever wondered what it is about an otherwise great product idea that just happens to weirdly not sell very well? 

When a useful, problem-solving product always needs to be aggressively pitched, never “sells itself” but instead requires aggressive tricks and hacks to convince people to buy… it’s missing this final piece of the product-market-fit equation:  

The target market’s psychological bias for action. 

Here’s how bias-for-action works: 

If you’re a scrappy founder who has an idea for a clever solution to an “itch” you’ve felt… then of course you’re going to go out and do your research. 

Before you build, you need to discover that other people share your itch. 

But merely finding others who’ve felt the itch… is not enough. 

Your target market needs to—in addition to feeling the problem—also have a strong psychological bias for taking action to solve the problem. 

That sentence might read like I’m saying the same thing two different ways. I’m not. The distinction is subtle. And it changes everything. 

Behavioral inertia is a thing. 

It’s a big thing.

Behavioral inertia basically means that—for the most part—people do what they’ve always done. 

Human beings are creatures of habit. 

We like new stuff. And we like innovation. But we are seldom powerfully motivated to do radically unusual things in our lives. Most people don’t like to try radically different solutions to their problems. 

We like the familiar. 

This is why American adults eat about 1000x more mac and cheese than they do sea urchin. And yet, most people really enjoy trying new foods. 

If you ask a person if they like to try exotic new flavors, they’ll say yes. But if you watch what they eat in any given week, it’ll almost entirely be the same old stuff. 

This is because our psychological bias for action—when it comes to trying new foods—is pretty low. 

What shall we have for dinner tonight? 

Want to try that Bhutanese place? 

… Nah, let’s just get pizza! 

Behavioral inertia basically means that even when we know we should change—or try something new—we just keep on doing what we’ve always done. Because it’s easier. 

Behavioral inertia is between you and your customer purchasing your thing. And it has to be overcome. 

It’s not enough that you’re certain that your target market has the problem. 

It’s not enough that you have a solution that works to solve it, either.  

The question that matters is:

How motivated are they to take action to solve the problem? 

If they have the itch, how driven are they to do the work of scratching?

Because scratching an itch is work. Even when you have a really cool, shiny new scratcher.  

No matter how easy your solution is, it requires your customer to overcome behavioral inertia in order to use it. 

It requires them to find it, purchase it and try it out. 

Trying anything new takes effort. It’s inconvenient. It’s often easier to procrastinate. To keep feeling the itch and not do anything about it.

I see this all the time in software startups. Well meaning product designers create elegant solutions to problems that millions of people have, but they forget about the customer’s lack of bias for action. 

I recently heard a pitch for a startup that made live relationship therapy available instantly, via an app. A classic “Uber-but-for-couples-counsellors” strategy. 

The idea is if you just made it really easy for people to hit a button and solve a problem they very clearly suffered from—in this case fighting with one’s spouse—then they’ll use it like crazy. 

Itch = scratched. Pain = resolved. 

Customers will throw money at the solution, right? And then they’ll tell all their friends. 

The problem is, most people’s psychological bias for action when they’re fighting with their significant other… is pretty low. 

And asking people to add a whole new mental “category” for spending money into their lives—that of buying one-click relationship coaching—requires the customer to overcome enormous behavioral inertia.

It’s so much easier to do nothing, just like you always have. 

This is why inventing brand new solutions to problems that have never before been solved… is actually really, really difficult. 

It’s difficult to sell, because of inertia. 

Cryotherapy is a thing. You might have heard of it. 

If you haven’t, here’s the gist: You can go blast yourself with freezing cold liquid nitrogen and it makes you feel great (afterward) and does good things for your health. 

Cryotherapy isn’t sweeping the world by storm though, because most people’s bias for action—when it comes to seeking out liquid nitrogen jet baths—is unsurprisingly low. 

Most consumers don’t have a mental allocation of their paycheck that goes to freezing themselves. 

If you’re a cryotherapy entrepreneur, you might be able to get people to try it once. But sustainable use (that drives a high customer Life Time Value) is going to be tough.


Because of the behavioral inertia where everyone’s life is totally okay if they almost never freeze themselves. 

Products that skyrocket to success do so because they appeal to people with a strong bias for action. They solve a problem where the customer is also deeply motivated to go out and spend their money. 

They’re in the market for a solution. They’re hunting. 

Car dealerships exist because it is worth it for them to exist. 

It’s worth it to be right there, right on the busiest street in town… so that when people need a car, they know exactly where to find you. 

“Early adopters” are people who have a strong bias for action that is caused by wanting to be first. They’re people who take so much pride in being at the front of the new wave of tech (or whatever) that they spend a ton of time and energy educating themselves, seeking out the latest and greatest. 

For example, they know exactly how much RAM the latest smartphone has. 

And it’s the motivation to find stuff like that out that also gives them a strong bias for action. 

Shut up and take my money 

Entrepreneurs who find themselves exasperated at potential customers who are hemming, hawing and hesitating, despite: 

  • Being perfectly in the target demographic
  • Suffering from precisely the problem the product was built to solve 
  • Being financially able to pay for the product 

… Are entrepreneurs who’ve failed to find customers with the psychological bias for action. 

If you want customers who: 

  1. Throw money at you. 
  2. Who tell all their friends. 
  3. And who happily justify your price to themselves… 

Then you need to build and design products for people who are actively hunting for solutions. 

You need to design your product for people who’ve already overcome their behavioral inertia and who are ready to try new stuff out. 

You’ll find these people at the front end of the product adoption bell curve. You’ll find them checking out your competitors. They’ll be talking online to other fanatics who are just like them. 

You see the problem with “Uber, but for coaching”?

Or “AirBNB for exotic sports cars”. 

Or for yet another productivity/to-do list/project-management app being advertised via Youtube pre-roll commercials? 

Or whatever. It doesn’t matter. 

All ideas of this kind will only appeal to a tiny segment of people who are already obsessed. 

They’re the people laying awake at night thinking to themselves “Why isn’t there a way I can borrow a rich person’s Ferrari’s when they’re not using it??!”. 

What these kinds of ideas will not do is convince the people who kinda would like to drive an exotic car… to do so. 

The activation energy is too high. 

You gotta sign up, you gotta pay money, then you gotta go drive it.

These slickly designed project management tools will never convince fundamentally disorganized people who run their lives via post-it notes… to get their shit together. 

The activation energy is enormous! 

The first thing you have to do, when you download that new productivity app is import a bunch of your data and get to work color coding your categories. 

(Unless of course, you’re smart enough to outsource your productivity planning to a pro!) 

With the sports car or the software… It’s easier to just stay home. 

Put on Netflix. 

Do what you always do, instead. 

The most important question any entrepreneur can ask themselves is: Who am I building this for? 

And, how motivated are they to go out and throw money, time and energy at solving this problem for themselves? 

If they’re doing so—if they’re already trying and it’s costing them money, time and energy—and if you have a better way… you’re going to win. They’re going to want to try your thing. 

I remember the first time I logged into Facebook. I was at an age where socializing—being “inside” the right circles—was pretty much the most important thing. I was already spending a ton of time and energy connecting. So the activation energy required to get set up on Facebook was worth it. It was so worth it that it felt like fun. 

As an entrepreneur, you never want to try to persuade people to try something totally new, that solves a problem they’ve been happily living with. Or tolerating. 

Find and build solutions for problems people are itching to lose, not just problems that merely itch. 

Get in the habit of asking yourself this one simple question:  

How strong is the target market’s psychological bias for action? 

You need to know. 

If you’re an entrepreneur, you’ve experienced that pivotal “I need some productivity hacks” moment. 

It happens in every entrepreneur career when an exciting new idea, glowing with uninformed optimism… morphs into an oh-shit-this-is-tough venture. 

In those moments, entrepreneurs double down on productivity and focus. They start making lists, tracking their time in 20 minute increments and just generally doing whatever they can to become laser focused. 

The focus and productivity business and every seasonal fad it manufactures—did someone say “bullet journals”???—is big business. Huge business. 

Every year, entrepreneurs (and civilians) spend millions on everything from productivity self help books to nootropic supplements. Software is the biggest category by far, and new slickly designed apps are constantly coming to market—all promising you’ll become a better you. 

Here’s something I believe that no one else does: 

Software alone will never make anyone more productive 

The human brain is divided.

Scientists are learning that the neocortex—the part of our brain that scientists are using when they research, and that you’re using when you try to be more productive—is really just the mind’s “wrangler”. That there are other, deeper parts to our psyche that make up who we are. 

And it turns out, our limbic system—sometimes known as our “Mammalian Brain”—has a lot to do with our motivation. 

Focus is a front-brain process. It’s something the most grown up, conscious part of you makes you do. 

The drive though… the desire to sit down and focus… that comes from this more ancient part of our brain. 

The mammalian brain cares more about human connection than anything else.  

The brain we share with our primate ancestors was built for team work. It’s dedicated to noticing—and caring about—subtle social clues. It’s deeply concerned with whether or not the other monkeys like us. 

(It evolved this way because being liked—and cooperating—with the other monkeys was a tremendous advantage that let us get lots of food and have lots of babies.) 

The mammalian brain is why software—no matter how smart the AI assistant—will never motivate you to focus 

I have strong opinions about all of this of course. I’m the founder of Commit Action, a “focus and productivity” service for entrepreneurs.

Commit Action started when I began toying with the idea of taking what I believe to be the most important part of coaching and therapy—the human connection and accountability—and splitting it out from all the other advice, strategy and tactics. I envisaged a sort of “clean” form of productivity coaching. 

We struck gold at Commit Action when we realized that what’s broken about to-do lists isn’t the to-do list… it’s that most people build them by themselves. 

Human beings outsource their sanity. 

It takes a village—or at least a single dedicated thought-partner—to organize a human mind. 

Commit Action works because instead of building your to-do list yourself each week from a place of isolation and a vacuum of accountability… you have it built by a human being whose sole job is managing your focus. 

This switches mammalian brain on. Motivation and focus flow. 

We realized the same thing that was broken about to-do lists, was also broken when it came to calendars. 

My digital calendar system works great. 

I live and die by it. It’s a digital bible of exactly where I will be and who I will be talking to. I adhere to what it dictates.100%. 

Except for appointments I make with myself. 

Because I don’t make appointments with myself. What I do is fill my calendar up with stuff where I’m accountable to other humans to show up. And I just try to fit in all my actual work between that stuff. 

Any time I make a date with just myself—to work on something exponential and game changer—it’s not an appointment. It’s just a loose intention to “get to that this week”. 

And if I put little sessions on my calendar like “Write a blog post” from 9am-10am? 

… Without the human accountability of a real meeting, I’ll blow that “appointment” off for something as low leverage as an email or Slack conversation. 

Everything changes when you add human connection to your most important appointments 

My business moves forward exponentially when I take a certain type of action. 

At Commit Action, we call it “Growth Driving Activity” or GDA. It differs from business to business, but it has the same psychological formula: GDA requires courage more than effort.   It drives exponential business growth (1+1=10). And it’s the easiest thing in the world to procrastinate. 

Executing on GDA should be a scheduled, committed appointment we make with ourselves each and every week. Even if it’s only for an hour or two. 

Adding accountability to our commitments to our self radically increases our motivation to execute. 

I’m excited to announce—today—the release of the biggest evolution in our service offering at Commit Action since the company was founded. 

Now, in addition to building out professionally clarified to-do lists for our customers… our Executive Effectiveness Aides will also create a new calendar for our customers. 

The Commit Action Calendar is designed explicitly and specifically to sit on top of a busy entrepreneurs appointment calendars. 

Future of Productivity

I personally have three calendars (for three different companies I’m involved intimately with) and a calendar I share with my wife. Every appointment in each of these is a commitment to show up somewhere (or on the phone) with another human. 

The Commit Action Calendar is the calendar for the appointments you need to make with yourself.

The calendar we’ve built represents a commitment you make to yourself to execute on your boldest plans. 

The tech we use allows this calendar to effortlessly subscribe over the top of any other digital calendar system you use. The idea is to see exactly how your appointments-to-yourself line up with—or get crowded out—by your appointments with others. 

This isn’t a replacement for your current appointment system. It’s the addition of a new, most important layer on TOP of your system… that represents a commitment to treat showing up for your own projects with the same focus and dedication you do for coffee meetings. 

Think of The Commit Action calendar as a layer in your week-to-week plans that carves out the time you’ve always meant to carve out… to work on the stuff you’ve always intended to. 

Our philosophy at Commit Action is that the future of ultra-optimized focus and productivity is human. 

Your “Appointments with yourself”are now a commitment your mammalian brain has made to yourself and your Commit Action Aide on your team.

We believe that having a dedicated team member (our Executive Effectiveness Aide) in your corner—someone whose sole job is keeping you in the zone—is a vastly superior approach to entrepreneurial productivity.

Outsourcing your focus and productivity this way taps the mammalian brain for maximum success. 

We believe that when you outsource the battle of organizing and clarifying tasks—and now, when you outsource the battle of making an hour by hour plan for the week—preserves your willpower and powerfully frees you up… to actually do the work that matters.

The Commit Action Calendar is a done-for-you solution. All you have to do is show up. Your Executive Effectiveness Aide will build it out for you—concierge style. You’ll be free to do what you always knew you were meant to do best: Execute on big vision. 

We’re really excited about this new direction and have already seen promising results. While other companies are building our AI chat bots designed to coach you on productivity, we’re more determined that ever to support the world’s top entrepreneurs with our thesis: 

That pairing dedicated productivity aides with our entrepreneur clients—and empowering them with clever tools—is the only way to transform these entrepreneurs into the highest leverage versions of themselves possible. 

Every wildly successful entrepreneur with an ounce of genuine self awareness and intelligence knows that luck is a big part of their success. 

Finding product market fit. Timing. Chance meetings that change everything. Bad decisions that ultimately led to good places… 

All these things are present in the biographies of super successful founders. They are all integral to their success. 

This isn’t to minimize entrepreneurial smarts, hustle, determination or discipline. Those things matter enormously too. There are countless books and gurus offering strategies for optimizing these. 

But what about manufacturing luck? 

Luck only appears impossible to create at the surface level. Go a little deeper and you find the simple idiomatic truth: The harder you work, the luckier you get. 

(Lady fate helps those who help themselves.)


Entrepreneurs can do even better though. Let’s go deeper: 

Luck is as much a game of endurance as it is a game of chance 

Entrepreneurs who optimize for longevity – being able to iteratively play the game of business for as long possible – increase their chances of luck finding them. 

This is why we see young people hit home runs with technology startups. Getting involved in “The Startup World” in your early twenties makes a ton of sense, so long as you can find a way to pay your (relatively few) bills while you play with your ideas. Keep at it and – chances are – you’ll eventually win in some way. 

Conversely, the people who start companies with short runways and enormous expectations driven by hard financial necessities in their lives… seldom get lucky. 

Think of the financially vulnerable forty something who’s always wanted to start their own company. The kind of person who only does so after attending a seminar teaching some scammy strategy to make millions online (or in real estate, or whatever) with “zero money down”. 

People jump into such courses – often going into debt to pay for them – needing to make five figures a month. They’ve got kids, a mortgage to pay for. They get sold on the idea that having their “back to the wall” is a good thing. It isn’t. It’s just a tool fake gurus use to sell courses to desperate people

The problem is these people don’t have the time.

When would-be entrepreneurs only have a couple of months to manufacture a win, they don’t give Lady Luck the time she needs. It doesn’t even matter if they’re hardworking and disciplined.  

Luck is notoriously late to every party. The stress of a super short cash runway doesn’t help either. You have to play the long game for her to help you out. 

There is a second way to optimize the odds of Lady Luck showing up:

Optimize for meeting people

Luck manifests most often through other human beings. It shows up in the game-changing conversation with a super qualified mentor who just feels like helping you out. Or in meeting the  person who’ll become your ideal biz partner. 

Or, just finding that would-be customer who becomes your first major fan and advocate. The person who singlehandedly jump-starts your word-of-mouth marketing. 

At my Accountability Coaching company Commit Action we talk a lot about the double-edged sword of technology: Thanks to the internet, it’s never been easier to start a business (all you need is a laptop) but working from home with just a laptop is actually not an environment that lends itself to business success. 

At CA, we mainly focus on the isolation and lack of accountability problem that prevents people operating as the highest leverage versions of themselves possible. But another side-effect of working from your home office – or even from seductively “location independent” poolside places – is that you’re unlikely to run into the people who can change everything for you. 

Getting out to events, visiting the cities that serve as hubs for your industry, taking a leadership role in connecting others… all these things serve to construct weighted dice in the craps game of early stage company building. You need to be doing them. 

I suspect that this step is the key to overcoming a lack of privilege. As a white male, I can’t say I genuinely know first hand, but it seems to me that the best way to find “unfair advantages” in business is through community/network… and if you’re a member of a minority community you should be leveraging any and all opportunities available to you. 

My personal analogue for this is when quite recently (and to my shock) I connected with several people involved in New Zealand’s government whose jobs are dedicated to “supporting kiwi entrepreneurs overseas”. 

I’d been happily going it alone for the best part of a decade. Turns out that all manner of grants, incubators, subsidies and mentorship had been available to me all along. All because I’m a card carrying member of a faux-minority called “Kiwi’s doing business overseas”. 

I’m very fortunate to have such connections, but the point is that it took me a decade of muddling away before I stumbled upon them. Because I just didn’t think to proactively seek this stuff out! Now, it’s actually too late and I’m not even qualified – I’m much too far along/experienced – for most of the juiciest opportunities. 

Don’t make the same mistake. Seek out opportunity and support.  If it’s not local government, then perhaps it family. Or friends. Or applying to an incubator. You don’t have to do this alone.

One last thing: 

Speed of execution invites luck in

The math is simple. When you sit down to play roulette, the faster you play the more chances you have. 

The metaphor is imperfect because with actual gambling, the house always wins. There’s nothing to learn from each spin of the wheel, so the next game has exactly the same odds as the last one. 

Entrepreneurship is fundamentally different though: Speedy execution is amazing because it accelerates your education. 

There are certain street-smart wisdoms that mega successful entrepreneurs talk to each other about. They’re difficult to describe to people who haven’t “been there, done that”. They can’t be easily written down, which means they cannot be learned by reading. They have to do with testing ideas, learning, pivoting, gaining true empathy for your customer and more. 

These are things about entrepreneurship you can only learn by doing. And they must be learned.

This is why perfectionism is the natural enemy of luck in business. 

Anything that slows down the process of iteration, of shipping to the market, of getting feedback from the real world… and then of integrating that learning into the next iteration… anything that retards any of these essential processes is counter-effective to getting lucky.

Executing relentlessly and quickly, seeking out and investing in relationships and simply staying in the game as long as possible are practical tactics to play the game of business with a tremendous lucky advantage. 

Uninformed Optimism is a cognitive bias that wreaks havoc in entrepreneur brains. 

It goes like this: 

The less you know about a project or business idea, the easier it is to believe it’ll be simple to make the idea succeed. 

This is particularly true for “marketing tactics”. The people selling “shortcuts” know it, too. 

The best way to make millions with a scummy info product is to be on the absolute bleeding edge. Sell a course on Facebook Messenger Bots a week after Facebook releases the feature. 

This works because early on, almost everyone is uninformed of the details of the new money-making tech. So it’s easy to convince people to optimistically invest. 

People naturally believe anything new is a huge, easy opportunity. They’re optimistic because they’re uninformed. 

Uninformed Optimism is rocket fuel for get rich quick schemes. 

(Look no further than the uniformed laypeople jumping into cryptocurrencies last year, and the snake-oil “courses” about crypto investing be sold to them.) 

Be warned though. If you do actual the entrepreneurial work of creating value in the world, your relationship to your new idea will change. 

Unformed Optimism naturally evolves into Informed Pessimism. The more you actually execute on any idea, the more you learn. You start to realize how complex (and challenging) your idea actually is.

This is why wannabe entrepreneurs endlessly flit from idea to idea. They’re intoxicated by the optimism of newness. As soon as something gets familiar, it gets tough. So, they talk themselves out of it and find something newer that – by definition – is vastly more promising than the idea at hand. 

Success happens when people push through the Informed Pessimism that develops. It’s impossible to skip, but beyond it lies Informed Optimism. 

Informed Optimism is the promised land of business success. It’s where you have both expertise and real experience. And it’s where entrepreneurs really capitalize on opportunities. 

And the biggest thing to help get you there? 

Awareness. Knowledge of these inevitable mental bias “bugs” and how they effect your mind. 

The only other thing you need is the determination to execute, in spite of the bugs in your brain. 

Outsource your battle for Focus and Productivity

Commit Action’s Executive Aide service helps business owners become the highest leverage version of themselves possible.

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