Guerrilla Entrepreneur

I’m a solo entrepreneur (now with a small team). I write the software, do the marketing, mop the floors. I attend no meetings. I need approval from no one. The design work is done in my head or doodled on a scrap of paper and communicated to the team directly. We want to magnify the advantages of a small force on a larger more cumbersome opponent.

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If you want to make money at some point, remember this, because this is one of the reasons startups win. Big companies want to decrease the standard deviation of design outcomes because they want to avoid disasters. But when you damp oscillations, you lose the high points as well as the low. This is not a problem for big companies, because they don’t win by making great products. Big companies win by sucking less than other big companies. So if you can figure out a way to get in a design war with a company big enough that it’s software is designed by product managers, they’ll never be able to keep up with you. - Paul Graham, Hackers & Painters

Creating shared knowledge and understanding within a group is challenging. Coordinating goals and objectives that are imperfectly understood between multiple groups of people adds another layer of complexity. Groups have different priorities and resources, their members have skills and knowledge that applies to a small portion of the whole and they lack the basic vocabulary required to understand those of the other groups. Creating a shared vision and getting all the members of a diverse and complicated organization moving in the same unified direction on any given subject is a monumental undertaking. The results are often less than ideal.

If you’ve ever worked for the government or a large corporation (both for me), you know half your working life is meetings. The main way large organizations tackle the inherent communication problem is to gather people together to talk. Significant effort is expended just on the systems used to book a space and time for the people to gather and on the technology they use to talk. Volumes have been written on the inefficiency and uselessness of business meetings, but I don’t have to convince you, you’ve been in those rooms, wondering, “Do I need to be here for this?”

A small team can all sit in a room around a white board and hash things out over lunch. They lack the communication problems inherent in large diverse groups. Small teams have meetings too, but all the decision makers and doers are present.

The old adage that two heads are better than one; it works for a small group, but 10+ heads do not produce 10x results, instead they find a median approach. As Paul Graham alluded to, large organizations create systems to eliminate risk, because they can’t afford risk, there’s too much at stake. But change is risky, innovation is risky.

A small team can make a decision to make a feature change on Monday, start it on Tuesday, and have it in front of customers by the end of the week. It’s a ruthlessly efficient process for developing and testing new ideas and the speed at which they can move helps manage the risk.

Working in a small team comes with a long list of challenges, but the agility with which you can move is unparalleled. Modern technology allows an individual with a modest set of skills to design, build, and deploy a software product to a global market in a matter of days for less than $100. People inventing things in their garage have unprecedented power to create new products.

Large companies entrenched in the market you are interested in look impressive and forbidding, as inevitable as a mountain. The truth is that they have never been more vulnerable. Working a few hours on evenings and weekends you can make as much progress as an international organization with a budget. It’s counter-intuitive, but true anyway. Don’t be afraid of the big guys, keep working on that side project.

Guerrilla Strategy and Tactics

guerrilla: noun - a member of a small independent group taking part in irregular fighting, typically against larger regular forces.

Guerrillas work at the edges, avoiding direct confrontations, moving into blue oceans. What aren’t your competitors doing? Can you eliminate competition by moving in a direction that they are not? What features do they all have that are expensive to build and maintain? Can you make a leaner product that eliminates their bloat? What you don’t build is as important as what you do.

The web allows you to reach a large number of people and win support and influence. You don’t need a large audience to test ideas; find a niche. Being successful does not require a large market segment when the whole world is your market, a tiny percentage is good enough to test, a couple points and you’re making a living.

Guerrillas use captured resources in their fight, utilizing the enemies own weapons against them. Steal your competitors designs! What are they doing well? Can you adopt winning ideas, functionality, or design elements? As artists, software developers, and guitarists all know; everything you make is derivative, building on what’s been done. Don’t be shy about borrowing good ideas.

Guerrillas use the environment to their best advantage. What can you farm out to 3rd parties? We are in a unique time. You have the same access to resources as your larger adversary. Amazon Web Services, for example, gives you access to the same incredibly powerful cloud server architecture and tools that the largest companies in the world use. Take advantage of the incredible infrastructure that you can tap into.

There has never been a better time to be a maker. You have immense power to create things and get them to market. Technology and innovation have provided you with levers big enough to move the world. Goliath is plodding and slow, so grab your sling shot and go take on that monster.

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