I’ve met a number of successful religious entrepreneurs, they always seem to have a sparkle in their eyes. I’m jealous of their belief, their conviction that they are doing God’s work and their business is all part of the plan. I imagine them during difficult times, still confident that God is listening, hovering above their advisory board, an exalted honorary chairperson or chairdeity.

I just have my cold hard cynicism and rationality. I have take all the risks without any faith and know that if I fail, then that’s on me - it is not part of God’s plan.

Can you fake it?

But there are also many entrepreneurs with a religious like belief in themselves and their business plan.

There’s this idea that you need to be a bit dumb to start a business. If you’re too smart you’ll realise how much work it is and how small the chances of success are so you probably wouldn’t start to begin with. But if you were dumb enough to try, by the time you realise how hard it is going to be, you’re already heavily invested and it’s too late to turn back.

Having faith is rational

So a bit of blind faith that you’re going to succeed is almost a necessary condition for starting a business.

In fact even if your idea is totally wrong, if you can still muster enough faith that the next idea will work, then you’re still in the game. And I think a lot of entrepreneurial success is down to staying in the game - it’s a hard slog and luck is always a factor, but if you keep rolling the dice, you increase your chances of rolling a six.

Mindset it also key, and having belief in yourself and what you are doing really helps keep you in a positive frame of mind.

So for rational, cynical entrepreneurs like me, the rational thing to do is to muster up a little faith. Like me, you might not be able to go as far as motivational roaring at yourself in the mirror in the mornings. But you can at least observe your thinking, and listen less to the rational pessimistic thoughts and more to the confident optimistic ones.

Of course, if you’re lucky enough to be able to roar at yourself in the mornings, then why not go for gold, aim for the skies and have God on your advisory board.

I’m no social scientist, so I’m not going to reference any studies, but I am familiar with the general phenomenon of expertise often being very domain specific and difficult to transfer.

Can you apply Chess strategy to business?

As I picked up chess as a regular hobby a few years ago, this an example I can comment on. Here’s an article chess.com about "How Chess Can Make You Better At Business". The headline is misleading, it should be “Some parallels between being a successful chess player and being successful in business”. The examples it uses are all of very basic and broad points like “be aware of your/your opponent’s weaknesses” and “have a plan” etc.

In the article, it includes a video of a Chess grand master pointing out a beginner’s early move setting up for a weakness later on. This makes my point and the opposite point of the headline - you need to be a master of chess to spot a weakness in chess. I’d be fairly confident that if that chess grand master started a business, he’d be a beginner again and a veteran entrepreneur would be able to quickly flag up potential weaknesses that he wouldn’t spot.

Domain skills are often like language skills

When you learn a language you build up some intuitive understanding of language, or linguistics - subject, object, verb etc. This is helpful for learning a second language, as languages tend to have a lot of overlapping concepts, so for example there’s no need to learn a new concept for “subject”.

If you’ve learnt a second language, you’ll be even better equipped for learning a third language, for example you’re used to the awkwardness sounding like an idiot again when trying to speak. However despite all this, learning a new language is still a momentous task, and the skills you’ve acquired from learning one or two languages only slightly shortens the journey to fluency.

I think this is a good metaphor for the transferability of skills across domains - some parallels between mastery within domains doesn’t mean a fast track to mastery when crossing domains.

So why is this useful to know?

I think this is a helpful insight in several ways. Firstly before you start down the road to master something you should know that it probably doesn’t have many (or any) paths leading elsewhere and you’d better be happy with where it leads. I like playing chess, but I’m under no illusion that the hours I’ve put in have much benefit other than fun.

It’s also a good way of identifying rare talent. A track record of successfully crossing domains is great endorsement. For example Netflix pivoted from DVD rentals to a gargantuan streaming service and producing their own films - that’s the kind of management investors keep an eye on.

Finally an obvious takeaway is that it’s a good idea to accrue skills that are more transferrable than others.

Are there skills that do transfer across domains well?

Here’s a few counter examples of skills which do transfer to some extent.

People skills

I think people skills a lot more transferable across cultures/societies. From my travels and observation of living in different societies, I think it’s different to languages - that fuzzy skill of dealing with people transcends the cultural/societal rules. Cultural and societal rules are significant, but they are the easier part to learn.

You can consider leadership, management, sales etc as specific examples of people skills.

Entrepreneurial skills

I know a lot of people who have started businesses, and can definitely see a pattern that some people develop, it’s almost like they can smell money. Successful entrepreneurship is a mysterious cocktail of skill, luck, persistence and a certain common-sense like quality that highly intellectual types often lack.

Programming skills

Software development is a good counter example, as programming languages have some parallels to spoken languages but it is the opposite case in programming language. The abstract concepts behind programming languages are much more of the work, and the specific syntax and conventions of each languages are a much smaller part of the work. It took me a few years to get good PHP and web development, but it would only take me a matter of weeks to convert to Python, I can’t say the same about learning Chinese after having learnt Japanese.

Learning how To learn

Finally, there’s the skill of learning, as a kind of meta-skill. Although this isn’t strictly crossing domains - since each time you learn a new skill, you are still learning, it’s very useful to get better at learning.

Related reading

As an interesting ending to tie this altogether, I recommend the boot The Art of Learning: An Inner Journey to Optimal Performance (2008) by Joshua Waitzkin.

Joshua is (or was) a chess prodigy/grand master and then went on to become a master of Taichi push hands.

Having founded an art marketplace I’m familiar with the quirks and ridicularity1 of the art world, and so I was willing to give NFTs a wide berth. On the face of it, it seems ridiculous that people are willing to bid millions of dollars for a pointers in a database (blockchain) that don’t even confer any kind of legal ownership over what they point to.

Fake Scarcity is Beautiful

However you can reduce the art world to almost the same thing. The value of any artwork is almost entirely down to what someone is willing to pay for it.

Consider a world in which art critics, gallerists, collectors and all memories of them from all time suddenly disappeared in a puff of logic, what is the value of Vincent van Gogh’s Sunflowers painting at that moment? You could perhaps argue that “oil paintings of flowers” are more likely to be popular than “oil paintings of manky buttocks”. But there’s already a lot of oil paintings of flowers and in this temporal non-art-world world any given painting, including The Sunflowers, would not be priced that much above the value of the canvas.

So if people decide there’s beauty and meaning in pointers in a database (the ETH blockchain), then I find an artistic beauty in that.

Note that I’m not saying that the all those egregiously shit NFT ape avatars you can see twitter are “art” - they are unquestionably shite. The beauty is in the fact people value the unique/scarce (that aren’t really scarce)2 pointers in the database.

Right Click on my Rights

It’s even more beautiful that many (most?) web3 peeps and owners of NFTs don’t understand the technology they are using (or for that matter copyright law3). Like some sort of metaverse Fyre Festival, people just turn their cash into tokens and pile into the party.

Centralised Decentralisation

Web3 is much more than NFTs of course. You’ll find it enthusiastically described with terms like democratisation, decentralisation of the web. There’s so much enthusiasm in fact, that people don’t mind that web3 is coming up with all kinds of cool centralised solutions. So beautiful.

Pre-idea

Web3 also brought us the term “pre-idea”. I’ll just leave this here:

It all Makes Sense Now

What a beautiful work of art it all is.

There’s no leader, no plan and nobody knows what direction it will flow in next. The whole internet has complimentary front row seats to the largest ever art performance, giant, decentralised and utterly meaningless. Sit back, relax, open a bag of pixelated popcorn and enjoy the show.

Further Reading: https://web3isgoinggreat.com/

I also realised that these regular feelings of anxiety were affecting my entrepreneurial activities - my day to day work was influenced by a desire not to feel anxiety, either by overcoming it (e.g. spending a lot of time on public speaking) or avoiding it (e.g. massive procrastination).

This is an example of what I’d call an “internal problem” - whether consciously or unconsciously, I’m trying to solve an internal feeling. I have written about anxiety before, but some other examples that might conjure up internal problems would be self esteem, being overly extroverted/introverted and being obsessive.

Entrepreneurship is choosing which problems to solve

As an entrepreneur, I’m used to solving problems. I think you could fairly accurately describe entrepreneurship as 20% ideas and 80% problem solving. And as a further refinement, I would suggest successful entrepreneurship is largely about choosing the right problems to solve (the lazy entrepreneur would certainly agree).

One key point about entrepreneurship is that there’s no boss, no-one is telling you what to do - you take all the responsibility on making the decisions. This makes it extra hard, because you have more choice - if you’re not paying attention to or ignoring what is going on “internally” you may not be making the best choices for your business.

Of course I’m not saying solving internal problems is wrong, far from it - overcoming some long term internal issue can be truly life changing and really help you with your business. But you still want to have perspective and parse apart the internal problems from the external, so you can be objective about which problems you choose to solve.

Seek Short Feedback Cycles

Successful options trading and starting a business are about taking calculated risks. In options trading the risk is stark and obvious - you have realtime profit and loss on your screen at all times - every action you take is quite obviously a risk.

With a business on the other hand, accurate profit and loss can be months behind real time. Also as you’re likely involved in many disparate activities, most of the time you probably don’t have an in-the-moment sense of risk taking from what you do on a day-to-day basis.

If you could have a real time profit indicator on your business activity/project, you’d be able to stop the ones that aren’t working and focus on the ones that are. But as the “fail fast” mantra goes, see what you can do to shorten/short circuit feedback times, or focus on things that have an inherently shorter cycle (like paying for search ads vs SEO).

Yes, some great things will have long slow feedback cycles, but you can try those later after you’ve had some success short cycles.

Know how much work you are committing to

In options trading there’s very little work to do once you’ve made your decision. If you want to buy AAPL (Apple inc), you just click a button - the work is coming to the decision. It couldn’t be more different in the world of entrepreneurship, the decision to do something usually marks the beginning of the work.

So my take-away here, is to look before you leap - be aware of how much work you may be committing to when you start something. Similar to the short feedback cycles idea, (and the lazy entrepreneur) you should be biased towards things that take much less work, that way you can get more rolls of the dice for the same effort.

Don’t make key decisions in an emotional state

Even though it’s just essentially looking at number on a screen, options trading is one of the most adrenaline fuelled activities I’ve ever tried. Seeing my account balance wildly fluctuate was an emotional ride. Quite famously many trading algorithms and professionals profit from the predictable human emotional reactions of the “retail” traders (the panic sellers, the chasers etc).

The takeaway here is to not put yourself in a position where you are making decisions in an emotional state. And thankfully this is much easier in a business than in options trading. If you recognise you’re not in a calm state, most of the time just you can simply postpone decisions, by days or even weeks if need be.

Know the difference between hope and having a plan

One fun term I learnt from the world of options trading was “smoking hopium” - this describes someone who holds on to a losing trading, watching as they lose more and more money still hoping things will turn around rather than cutting their losses and moving on.

Of course you don’t expect things to always work immediately, so you’ll generally expect to see some red before going green. But it’s crucial that you’re either good at adjusting your assumptions and changing course on new information, or you have your decisions laid out ahead of time (I’ll cut my losses at -10%).

I assumed I’d be rational and good at adjusting my strategy based on new information. But I’m only human, which means I am adept at doubling down on wrong ideas despite evidence to the contrary.

So this idea is a variation on the “don’t make key decisions in an emotional state” theme - if you already have a plan, then your decisions will already be made, no need for any hopium.

Know when to stop, know when not to trade.

Entrepreneurial success isn’t strictly correlated with time invested - it’s not “a good days pay for a good days work”. It’s even more extreme in options trading as it’s possible to make the majority of money for your year in one afternoon. As with options trading, so in entrepreneurship - the payoffs from your activity are non-linear, some things bring in orders of magnitude more than others.

One of the classic sources of failure in options trading is “over trading” - that is taking many mediocre opportunities rather than being disciplined and waiting for good opportunities. As the lazy entrepreneur will be quick to point out, sometimes is better to do nothing than do something mediocre.

Similarly, it’s important to know when to stop. I could go into more detail illustrating this with examples, however I think it’s only appropriate that I apply the lesson to this edition of Mr Kirkland’s Musings, and stop here.

The lazy entrepreneur doesn’t want to work that much, is quickly bored by busywork and is never going to suffer from burn out. Why is this desirable, contrary the common mantra of putting in 110%?

Actually there’s only three steps

Firstly, you need time and space to think beyond the immediate tasks in front of you. As an entrepreneur you are not laying bricks. Vision and imagination are a crucial part of your work and this isn’t the kind of work that purely down to the number of hours you put in, or how much you struggle.

Similarly you need space for happenstance and opportunity to do its work. This could be thinking or reading time, attending conferences; I like cliche of the “CEO on the golf course”. Make sure you’re spending some of your working day on something relaxing/fun, and especially something which has large potential upside.

Get someone else to do it

Secondly, the lazy entrepreneur would much rather have someone (or something) else do the work. A large part of growing a successful business is delegation and automation.

Even if you're a tiny or solo operation, you’ll potentially benefit from hiring outside help. A few hours of repetitive tasks can be cheaply outsourced, and it’s often smarter to hire and expert than go down the rabbit hole and do-it-yourself . Ultimately scaling up a business is largely about recruiting and leading the right team.

Automation is vital - in a basic sense, software startups/SaaS businesses are automation of some manual process(es). But equally a 21st century bricks-and-mortar business that doesn’t replace some of its repetitive tasks risks losing the edge to competitors.

Work leads to linear, lazy leads to exponential

Finally it’s a huge opportunity cost running after a mediocre idea when a good or great idea is just about to come along. By being a little lazy, you’ll struggle to succeed with a mediocre opportunity, only the really good ones will work. Once you’ve founded a few businesses you’ll see this in effect - one/some of them “just work” and grow much faster than the rest.

A mediocre idea will have linear returns, and a great idea exponential returns on the same effort - consider how that compounds over time.

A word on burnout

I’ve met many entrepreneurs who fill their day with carefully measured doses of caffeine, matcha or modafinil; minutely partitioned work calendars; body, diet and sleep hacks. This is all fine to some extent, as long as you have a healthy balance. If you don’t have that, you risk pushing things too far and burning out.

I’m speaking from experience here - I used to do it all, work hard, play hard, experiment with my exercise diet and sleep - and eventually I made myself chronically ill. It me took years to fully recover.

So in part I wrote this today because I know many of my fellow entrepreneurs are, like me boundless workaholics with a heavy bias towards activity. Tap into your inner lazy entrepreneur, it’ll help keep you from overwork, steer you towards a better outcome and save you from burning out.

Coming up next: crib notes from a decade of running remote teams; business lessons from options trading; channeling your inner business baboon…