3 ways to ease yourself into entrepreneurship

Let’s say you’ve got a day job at a company and you are not ready to quit to start your own business. For whatever of many reasons (excuses?), you’ve made the calculation that you either need the money / don’t have enough savings, haven’t found the right people to partner with, or you wouldn’t sleep well at night with all the intrinsic risks.

Yet you have an entrepreneurial streak and would like to start getting it exercised. Here are three practical ways to ease yourself into becoming a full-time entrepreneur:

1. Participate part-time in some other entrepreneur’s full time business. You’ve got a lot of skills, your day job is proof of it. You also have a stable income. Somewhere in your life is an entrepreneur who needs your skills but can’t pay you in cash. Get some equity instead, and practice whatever it is that you do for a living for him. You can share in the excitement, liberate yourself of the politics of the office for a few hours every night or weekend, and learn from the entrepreneur’s struggles and triumphs. Maybe with time you become more comfortable with the risks of starting a business, or the business you’re associated with grows and can afford your full-time services. This approach works for almost anybody, but is particularly suited to generalists such as marketing & sales, finance, legal, business development, strategy and product management.
2. Start a small-scale project that could turn into a full-fledged one later. More often than not the delta between corporate job and entrepreneurship lies within what you don’t know, not what you know. While approach #1 above is going to show you how a startup operates, somebody else is solving those problems. So if you want to learn about the things your peers do at your office, one idea is to start a small project where you can practice those things for yourself. For example: developing a mobile application for an app store, or a game, or a utility. These projects are generally small enough in scale that you can leverage your core skill and fake it enough with the other areas and offer you the perfect ‘test lab’ for your entrepreneurial ideas. This approach works best for technical people who have the core non-outsourceable skills a small project needs. Think MicroISV.
3. Start a project without economic ambitions. By far, the hardest thing to do in a new venture is to generate traction. It’s hard enough to get people to use whatever you have built, let alone get them to pay for it. A way, then, to learn entrepreneurship with ‘training wheels’ is to not even pretend to want to generate revenue. Do something good, do it for free, and see if you can generate free demand. With altruism at the center, it will be easier to attract other people to your project, either as volunteers or users. You can do good and benefit at the same time from the experience of building a team and producing something worth existing. There are many intriguing business models that have “Free” at the core. Some categories of software are especially a good fit for this, like B2B enterprise and infrastructure.

There is a fourth way: to join an employer that allows you to be entrepreneurial within the organization. The Google approach. It has many challenges, though, and in my opinion is only mostly doable with very adept corporate political navigators.

Common stumbling blocks to getting started:

• Your employment agreement doesn’t allow you to moonlight. There are two or 3 ways around this. Explain to your boss or HR person in broad terms what you’d like to do and get an exception in writing. Most forward thinking employers will. If your project has nothing to do with what your employer does, the chances are higher. You could also renegotiate your employment agreement. Need  a strong bargaining position for this. Or you can change jobs.
• Your job leaves you no time. Have a 60 hr/week job? Is the opportunity worth it? Sometimes, yes, many times, it’s an addiction. Can you get away with downshifting? What about getting a 20% pay cut and a 50% time commitment cut?
• Your life leaves you no time. You have kids, hobbies, or you love partying, or you need to take care of somebody. Some things are worth doing. Some others are just time-wasters. Strikes me how many people have a 20 hr/week part time job taking care of a TV screen.  Starting something requires re-prioritizing. It also requires having a support system: people who will make allowances for you to focus. Subject for another blog post.
• You don’t know any entrepreneur. This one’s easy to solve. Go hang out at a tech incubator, coworking space or startup / VC networking event in your town and you’ll meet tons of people. Maybe you hit it off with somebody. And you get to practice networking, which is such a necessary entrepreneurial skill.

Good luck and best wishes!