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.)

Sure. 

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.