Finding Product Market Fit: Lessons from the Military for Pre Seed Startups

I have pivoted three times from my original idea. That’s a lot in a short space of time but it has helped me find product market fit. Here is why I did it.

January 4th, 2017   |    By: Nic Woodhams    |    Tags: Bootstrapping, Planning, Strategy

In January 2016, after 8 years in the British Military, I left to enter our crazy world of startups. Over the past 8 months I have pivoted three times from my original idea.

That’s a lot in a short space of time but it has helped me find product market fit. I can attribute some of this speed to my military background. There is a lot of advice out there from the military to business and vice versa but here are some direct lessons I believe the military can teach the Pre Seed Startup:

The Why

No soldier is going to follow you to into combat unless he/she knows why they are doing it. When I started my first company KitShare (an Air BnB for surfboards, skis, etc) because I had no employees I hadn’t given it much thought until an investor asked me why I was doing what I was doing and I realized “to make money” isn’t a good enough reason.

Really drill into this because even if you haven’t got employees your investors and your customers need to know your ‘Why?’ I thought hard and mine was that I believe in the value to personal development that adventurous sports can give people. With that I was able to create a clear mission ‘to give everyone access to adventure sports’ this in turn caused me to pivot to a Class Pass for surfboards, skis etc called Adventure Pass.

I then went even further and pledged that a percentage of my profits would go to sponsoring disadvantaged and disabled kids on outward bound courses. You see a real, honest ‘Why?’ is much easier to get behind, it helps investors, it helps employees and it helps customers give you their confidence.

The OODA Loop

The ooda loop

In warfare one of the key tenants of any plan to defeat your enemy is getting inside their OODA loop. OODA stands for Observe, Orientate, Decide, Act. An example in combat would be 1. You observe a shot being fired. 2. You orientate to where you think it has come from. 3. You decide to fire back 4. You fire back. Now imagine that as you were Orientating another shot was fired from somewhere different — someone is going through the OODA cycle faster than you and holds the initiative.

The obvious use for this in business is with regards your competition, if you can get inside their OODA loop you will be dictating where your market is going and always be the first mover. Another way OODA can help is with your customer’s journey: 1. How are they going to observe your product. 2. How easy is it for them to orientate to your site/shop. 3. How can you make them decide to buy 4. How easy can you make the buying process. If you are in your customer’s OODA loop you are constantly satisfying them and gaining their loyalty.


Obviously the way to get ahead in the military and business is with good intelligence. On my two tours of Afghanistan I was focussed on getting HUMINT (human intelligence) from local tribesmen. This I could not have done without lots and lots of tea.

In startups you need people who want to buy your product but you need to know what they want first. This is best done over a cup of tea, beer, coffee etc. It is not just a low Cost per Click on Facebook ads. I spent two days in Geneva airport talking to people going skiing about one of my pivots (Geneva Ski Store). I spent two months in hostels around south america talking to travelers about Adventure Pass. Knowing your customer is intelligence and intelligent. Until you do, don’t invest in building or buying anything. So get out there and drink more!

War Gaming

The similarities to launching a product and launching an operation are quite stark. You need to have gathered as much intelligence as possible (talked to your customers), you need to have warned the right people (investors), you need to be have prepared the battleground (PR) & you need to have decided on what is most crucial to success (conversions, emails, posts) But one thing I have seen friends with startups fail at is ‘War Gaming’. Essentially going through as many eventualities as possible and deciding what you will do if this or that happens.

Do it with your business: imagine a scenario where you’re whole market shifts to a different demographic, are you ready to cater for it? What will you need to do differently? How much will it cost? How does that effect your ROI or your CAC? Will it be worth it?

You won’t regret doing this with your team for an afternoon, it makes you more nimble than your competitors and builds confidence in your product. You never know, just war gaming could lead you to that golden pivot.

Ink Spot

Ink Spot

Modern warfare is not of the WW2 variety where there is an enemy to your front and you’re advancing toward them. Modern warfare is ‘360 degrees’ and the prize is not taking that hill or defeating that brigade, the prize is the population. You have to win the hearts and minds of the population, they have to think you are better than the enemy. The way you do this is by proving in a small area how this is the case. You secure one village, provide them with healthcare, education, safe access to commercial centres etc. If you do it in one village well, news will spread to the next and you create an what is called an ‘inkspot’ effect.

In business Paul Graham of Y Combinator says you need to prove your idea in the narrowest vertical possible first and grow from there. I prefer the inkspot term because there are things in each village (vertical) that they all want, identifying them is key before you select where to start.



Clausewitz the Prussian general and military theorist coined the phrase Schwerpunkt. It is refers to the enemy’s centre of gravity or control. Clausewitz postulated that you can defeat any enemy with minimal casualties by not engaging the enemy head on but simply destroying their Schwerpunkt. Without that control, there is no cohesion and therefore no resistance.

In business I like to think of the Schwerpunkt as the customer who should want my product or service but when I speak to them, is fiercely resistant to it. It’s hard for founders to see issues with their product but these people see them immediately. So you need to find these people, listen to them, adapt your product to work for them and in so doing shatter any resistance to them buying it.

Also shared on Medium.

About the Author

Nic Woodhams

Aspiring minimalist, lover of people & experiences. Commander of Adventure Pass & previously of a tank.

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