Going All-In

I wrote a piece last week about thinking in bets. In the piece, I outlined my general strategy for starting businesses.

Tom Littler
Apr 11, 2021

I wrote a piece last week about thinking in bets. In the piece, I outlined my general strategy for starting businesses. I argued that the advice of committing absolutely every ounce of your energy to a single project was a very high-risk strategy and that you might be better off spreading your bets over multiple projects instead.

Spreading your bets is all well and good. But sometimes you need to go all in.

Sometimes you need to stop pussyfooting around. You need to shake up your non-committal self. You need to grab the balls by the horns, pull up your shirt sleeves and put your soul into something.

The times you need to go all-in are rare. In my nearly 30 years this I’ve only done it twice.

Why You Should Go All-In

“Opportunities come infrequently. When it rains gold, put out the bucket, not the thimble” — Warren Buffet.

Output can be non-linear. When you go to the supermarket and pass your groceries through the checkout counter you are experiencing linear output. The cashier can only work at a certain pace, and he certainly has no ability, in the confines of his predicament, to use his brain to create large amounts of wealth.

When Satoshi Nakamoto coded the blockchain for Bitcoin, this was probably the largest example of non-linear output in history. In just a few months (presumably) of focused coding, Satoshi created, what is now valued at 1 trillion dollars of wealth.

All potential work in life falls somewhere on this spectrum of linear to exponential returns on your input. You want to avoid the linear like the plague, and seek the non-linear doggedly.

Sometimes in life, rare opportunities present themselves. Opportunities where with a fixed amount of work, you can reap a huge reward. These are the times when you need to go all in. These are the times when you need to look out of the window, see it’s raining gold, kick your thimble into the abyss and lay down your bucket.

The problem is recognising when it’s raining gold. Let’s take a look at a few signs you can look out for, so you can take action.

Signals To Go All In

Product/Market Fit

The customers are buying the product just as fast as you can make it — or usage is growing just as fast as you can add more servers. Money from customers is piling up in your company checking account. You’re hiring sales and customer support staff as fast as you can — Marc Andreessen, on Product/Market Fit

Product market fit can be described as having the right product, for the right market, at the right time.

Don’t get too hung up on Marc Andreessen’s software-led definition above. The product could be your professional skills in the job market. It could be your YouTube channel in the lifestyle market. Anything, where there are customers and products, involves product/market fit.

Product/market fit is also a spectrum. Some products have light p/m fit, others strong. Andreesen’s definition describes strong.

Most opportunities won’t show p/m fit from the outset. There will be some initial interest, there will be loyal customers, but generally, the process of building a business will involve a lot of graft, a lot of iteration, and a lot of experimentation. This is the norm. These opportunities are not ones where you need to ‘all in’.

Sometimes though, with seemingly 0 effort, you magically stumble upon insane product/market fit. Cash flows in, customers are fanatical, growth just happens without even trying.

The world is so saturated with talent, product, and information, if you ever find yourself in this position where people are devouring what you are delivering, you probably want to go all in.

It Feels Like a Frenzy

In my experience, most businesses, and most work, feel like a grind. I don’t mean this in a negative sense. Grinds can be pleasurable. I just mean that they involve putting in work, everyday, and seeing slow, incremental progress.

This slow, incremental progress is the backbone of a lot of success. ‘Habits are the compound interest of self-improvement’ and all that shit. Sometimes though, opportunities come that don’t rely on hours of dogged work.

I’m currently all in on early-stage crypto investment, and if I had to describe one word for how this space feels — it’s frenetic. There’s this feeling in the community that we are riding at the cutting edge of innovation, on the cusp of something that’s either about to explode or go parabolic.

When you are seeing huge results, without having to put in the work that usually accompanies them, go all in.

Skill-set/Opportunity Fit

Capitalising on an opportunity in a big way comes down to chance. Bill Gates happened to have insane computing skills, just as computer hardware was taking off. Jordan Peterson stated espousing his rhetoric on personal responsibility, just as young men were starting to feel lost in the world. Jack Butcher was creating digital art for a very tech aware audience just as NFT’s started to boom.

If these individuals had the same skill-set 10 years earlier, or later, they would not have experienced anywhere near the same success.

If the stars align where your skills are exactly what the market wants right now, it’s probably prudent to strike with haste and go all in. You might think that an opportunity will come along again, but the world is changing so fast, you have no idea if your unique skills will be something that is in high demand in 2 years, let alone 10.

All in opportunities appear rarely. But hopefully, by having an insight of what to look out for, when one does come along, you can act, and act fast.

The way people tend to work most effectively, especially in knowledge work, is to sprint as hard as they can while they feel inspired to work, and then rest. They take long breaks.

It’s more like a lion hunting and less like a marathoner running. You sprint and then you rest. You reassess and then you try again. You end up building a marathon of sprints.

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Made by Tom in Webflow