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. 

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. 

It’s time to come clean and tell you what’s really going on.

There are two parts to this update: The “What” and the “Why”. Let’s start with Why:

I’m really fed up and frustrated.

Productivity Software is utterly broken. It doesn’t work. It doesn’t get results.

Aspiring entrepreneurs are desperate. They’re frantically searching for breakthroughs. Hunting for anything that promises to boost their personal effectiveness.

They wage constant internal battles with themselves, where one part of them has unbelievably huge expectations and ambitions for their success… while the other part just wants to surf Facebook and watch Netflix. They hype themselves up and then beat themselves up… all in the same afternoon!

Meanwhile, their actual business is the refugee caught in the psychological crossfire.  Continue reading “Why I’m quitting my business to build software “

Passion is misunderstood.

Entrepreneurs LOVE to be passionate. We don’t consider someone to be truly successful unless they’re making (a ton of) money by following their true love in life.

“Finding your passion” is practically a spiritual quest. What could be more important?

If you’re unfulfilled by your work – or disillusioned by your lack of results – you might just need to find your passion to fix all that! Or so the saying goes.

But what if the search for your passion is insidiously sabotaging your potential as an entrepreneur?

What if Passion is actually crippling your progress, making you stuck and overwhelmed?

Over the last two years, my company Commit Action has conducted over ten thousand one-on-one phone conversations with small business owners and entrepreneurs.

We’ve worked with a professor of Neuroscience at Harvard Medical School. We’ve brought in a professor of Positive Psychology from New York University.

Together, we’ve crunched the numbers of thousands of entrepreneurs to answer this simple one question:
Continue reading “Why “Finding Your Passion” is self sabotage “

Apologies for the radio silence lately – I haven’t been missing-in-action, but simply enthralled and digging in deep with the work we’re doing over at Commit Action.

Turns out, scaling a coaching service to thousands of entrepreneurs becomes statistically fascinating. If you could see some of what we’re uncovering – trends, tendencies, cognitive biases – and what it suggests about the nature of entrepreneur success, you’d be stuck in the bat cave with me too!

One of the riveting concepts to come out of this work is the idea of an unfair entrepreneurial advantage, that some people seem to effortlessly do better than others in the pursuit of business goals. And when the team and I started asking WHY, things got really interesting.  Continue reading “This computer programming principle may be the key to unlocking entrepreneurial success “

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