Lately I've been thinking a lot about how we got where we are today, and I've come to the conclusion that starting a business is a lot like playing a game of RISK. If you've never played the game RISK before, I encourage you to find a friend and play the game. To understand the full impact of what I'm trying to convey, I'd like you to play RISK with just one other person, ideally late at night.

Position Your Army

The game starts by positioning your army on the board. You need to decide what territories to claim and continents to attack. This seems similar to how we started our business. We decided on a market to serve, products to offer and how to service our customers. While we believed we were making the right choices, we honestly didn't have a clue because back then the Internet was just in its infancy and pretty much everything was up for grabs. Things were so new that our clients never used a digital camera before and dial-up modems were the norm. Sure we interviewed dozens of retailers and wrote a business plan, but looking back, that was a fruitless exercise. Nearly all of the retailers we interviewed said they'd never have a website and didn't think e-commerce would be important to their brick and mortar store. This experience taught me a valuable lesson: sometimes people will think you're crazy, and even your potential customers may not understand or want your product or service. Ultimately, you may need to position yourself the best you can to get ready for your attack.

Roll Dice & Attack

The game of RISK is all about strategy and risk. The trick is to attack with just the right amount of men. You could attack a position with overwhelming odds to win the battle. However, if you deploy too many troops, you may find that you've weakened your flank causing others to attack you. Business is often very similar. If you spend all your time and money on developing the product, but don't devote any resources to sales and marketing, you may end up having something great that no one uses. Additionally, whatever you build or offer, there's a certain amount of risk that you simply cannot avoid. You need to roll the dice and see if you come up on top.

Retreat When Necessary

Entrepreneurs by definition are optimists who believe they can win any battle. This of course is good and bad. Good because it gives them the tenacity to keep on fighting even when there are significant odds against them, but bad because they don't often know when they've lost. Work hard to understand when you've lost so you can retreat, regroup your men, and fight another day.

Adapt & Change

Oftentimes when you lose a battle you'll adapt and change in some way. The harder thing is to make changes when you're winning. Very often businesses get set in their ways and think they don't need to make changes when they are winning. However, disruptive technologies and businesses are entering your market all the time and are hungrier than ever. Like a band of militia, they poke and prod at you until they find a weakness in your line. Once found, they attack in full force and take over the areas you once possessed. As a business owner you must not sit on your laurels, and instead, constantly challenge your team to adapt and change.

Troops Win The War

Wars are not won by individuals, they are won by the troops on the ground who share a common vision and are willing to do anything for the guy beside them. Starting a company is very similar. You need to find people and partners who are willing to sit in the foxhole with you and fight the good fight. You need to protect their flank at all costs, and in-turn, they will protect yours. Trusting and empowering the people around you will help you win many battles.
Starting a business may just be the hardest thing you may ever do in your life, and just like the game of RISK, it may take much, much longer than you expected. However, it may also be one of the most rewarding things you may ever do. Learn to take calculated risks, understand when you've lost, constantly adapt and change, and you just might find yourself winning the game.