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Navigating the Entrepreneurial Journey: 10 Hard-Earned Lessons from Starting a New Business

Nine years ago this week I took the leap and joined a new startup as employee #001.

On paper, the move didn't make much sense. It paid less than my current role. There was zero structure in place.

The goal of taking Japanese Saké into the world’s most glamorous bars, nightclubs, and hotels was optimistic to say the least - and yet - I found the lure irresistible. Perhaps it was the charisma of the founders. Or the chance to put my university drinking days to good use. I think I was just attracted by the sheer naked ambition of the thing. 

Regardless, I'm glad that I trusted my gut. It has allowed me to exercise autonomy, mastery, and passion. All things that I cherish and make work fulfilling. In short, I've grown and developed faster than I could have ever imagined. 

I am far from being the most successful person to have written a piece like this. There is nothing that makes me uniquely qualified to comment on what it means to be entrepreneurial. 

My journey is incomplete, but for what it's worth, I have at least been in the arena, with some milestones achieved (and many scars) to show for it. Below are just 10 of the most important lessons I’ve learned whilst trying to build a brand from the ground up and becoming a co-owner along the way.

I hope that these ideas resonate with those in the trenches, and serve to inform aspiring entrepreneurs of the road that lies ahead:


#1: The energy needed to start your own business, is not the same as the energy needed to sustain iT

There's no getting away from hard work, particularly in the first few years. You have to work incredibly hard, and burn so much fuel, just to get escape velocity.

Once you’ve escaped the earth’s atmosphere, then you can seek some kind of balance (and I have), but the hours were insane for a couple of years. This is where having abnormal levels of self-belief and irrational levels of optimism will get you through. The long days and nights weren’t so bad, because deep down, the founders and I believed in the power of our idea. 

#2: The '80/20 principle' is everywhere 

It’s applications go beyond the business world, but the principle is especially powerful here. 80% of your revenues will come from 20% of your customers. 80% of your leads come from 20% of your contact list. 80% of your problems will also stem from 20% of your customers.

Be stricter with small customers who eat up a lot of your time for comparatively little in return. Some of our best and most profitable customers are also our lowest maintenance. They love the brand, they get it, and always pay on time.

One useful exercise: block out an afternoon in your calendar just to step back and analyse which 20% of your activities actually move the needle. It can be incredibly powerful.

#3: if nothing else - 3 decisions or actions a day that get you closer to goal

Every day you should be asking yourself the question: "What can I do today that will move us closer to goal?” Make those actions a priority and execute on those above all else. Often these things will be painful or scary. Do them anyway. Do this consistently for years and you will be far ahead of most people.

#4: Increase the surface area upon which luck might fall 

This superb article sums it up better than I can but loosely speaking, there are actions that you can take that increase your chances of getting ‘lucky’.

I don’t champion 18 hour days and endless hustle. I am a massive advocate for working smarter, not harder. But the fact remains that if I send out twice as many proposals, see my clients twice as often, and hang out in places where potential clients socialise, then I’m going to accelerate much faster than the competition. If you kick up that much dust, some things are bound to fall your way.

Being known as someone who is trustworthy with a reputation for integrity also helps. More serendipitous connections and introductions get made, and this is a kind of luck that’s different from sheer chance. 

#5: People buy people  

We like to think that our buying and purchasing decisions are logical and rational, but this flies in the face of what I’ve observed. We are emotional, social creatures. Technologies change. Business models change. But human nature remains a constant. As the saying goes: “People hate being sold, but everyone likes supporting their friends".

#6: Everything will take 2x as long as you think (at least)  

Unfortunately, knowing this in advance does not help. But it does make those delays slightly easier to swallow. In the case of our saké business, dealing with individual customers like bars, restaurants, and hotels can be incredibly quick. Sales cycles at the international distribution level, however, are lengthy. Negotiations can feel glacial at times.

We've succeeded in getting Four Fox Saké listed at major airports, on airlines like Cathay Pacific, and available in Las Vegas, London, Seoul, and Sydney. But the period between receiving a ‘yes’ and actually shipping product can easily approach 1 year. Beware the cash cycle.

#7: The highs and lows are violent   

When you’re part of a giant corporate or large business, you are somewhat shielded from the blows. When you ARE the business, every bit of bad news is like a dagger to the heart.

Thankfully, it also means that every tiny victory delivers a surge of validation. Over time, you learn to weather the inventory shortfalls, collapsed deals, and irate customers. You’re able to respond strategically, rather than react emotionally.

I remain a work-in-progress, but having sailed through so many storms (and survived) I’m now far calmer and less prone to panic when things inevitably go wrong.

#8: Hanlon’s Razor  

Don’t mistake for malice, that which can be more easily explained by stupidity."

Most people aren’t actually out to get you, or sent specifically to ruin your day. More often than not it’s just down to incompetence, or incomplete information, or someone rushing when they should have slowed down. I've found this philosophical razor to be a very helpful shortcut for explaining human behaviour and avoiding feelings of victimhood. 

#9: outsource where you are weak   

Know where your blind spots are so that you can double down on your strengths. For a long time (too long) I tried to do it all. Head of Sales. Events Manager. Logistics Officer. Accounting Assistant. Delivery Boy. I ran our social media accounts too. Mostly from the back of an Uber between client meetings.

Admirable hustle, but the results were amateurish looking back. We now have an amazing team in Europe who handle all of our Creative Content. We also tried to do the accounts ourselves. Big mistake. Thankfully we now employ an external accountant locally. Attempting to reconcile 3 years, whilst running everything else, was excruciating. There were several weeks in 2018 where I wanted to crawl into a bin and die.

#10: Skin in the game: You can’t make people care 

Or maybe you can make them care. It's just really really hard. But giving skin the game can help incentivise people and avoid the ‘principal/agent problem'.

Understand this - nobody will ever love your product as much as you do. That’s why ensuring 'skin in the game' is so important. Credit to the founders for giving me equity early on, and thus a vested interest in growing the pie for all concerned. Making me feel like an owner from the start was a clever move psychologically, because it increased my passion and motivation to succeed exponentially. 

*Bonus lesson - Be kind.

Don’t be a pushover (that's a different thing) but be nice on the way up. The world is a small place. Merely being known as someone who’s pleasurable to do business with will get you far.

Clients change jobs, people talk, reputations matter.

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