How to Be a Successful Serial Entrepreneur

There are actually a few different ways to structure a multi-business venture. You can treat each business as an individual sole-proprietorship, but running multiple businesses is risky, and you don’t want to leave your personal assets unprotected. You can turn each business into an LLC or Corporation, which will mean each business is responsible for its own debts, but that means you have to file to create, and maintain, multiple entities. I recommend that most small businesses create one umbrella LLC or Corporation, and then have it file for ‘Doing Business As’ names for each company. For example, if you run a scented candle shop and a website design company, you’d form an LLC or Corporation, and then have it file for DBAs for both businesses. That is the easiest, and quickest, way to limit your liability for multiple businesses. Keep in mind, however, that this structure can put all of the umbrella company’s assets at risk—if that candle company gets sued, the assets of the website design firm can be seized as well. Be sure to take the time to talk these problems over with a lawyer before settling on a structure.

Every city and state has different rules and regulations for businesses. If you’re looking at opening a new business in another town, make sure you check their website and see what licenses you have to apply for. Even if the new city is just the next town over, you still need to make sure your paperwork is in order. Contact city hall, or check out their website, and find out what rules businesses have to follow, and what fees you have to pay before doing business. The Small Business Administration also has a handy online tool to track down the licenses and permits you have to apply for.

I can understand the appeal of having a different office or storefront for each of your individual business locations since you can then compartmentalize your life a bit better, but in the long run it doesn’t make much sense to have scattered offices all over the place. You’ll wind up spending more time driving between them than you will in them. Instead, you should have one office that serves as your direct point of contact with all of your files, finances, stock reports, and general work kept there. This centralization will help you be much more productive, and will help you keep better track of everything.

If you’ve ever run one business, you know how difficult and time-consuming entrepreneurship can be. Now imagine multiplying that work two or three times over! Learn how to hire a team you can trust, and then hand off some of your responsibilities to those team members. There’s no reason why you need to package every order or answer every phone call. At the very least hire a secretary to help with basic office housekeeping assignments—you’ll need every free minute you can possible get.

One of the first jobs that new business owners start to neglect when work gets hectic is basic filing and bookkeeping. You tell yourself there are more important problems than balancing your books, and suddenly you’re a month behind and struggling to zero out your accounts. If you’ve decided to start multiple businesses, you need to get, and stay, organized. Your calendar should be your new best friend, and you should create and keep to a schedule. Set aside time to answer emails and update your books, and then get into a routine. The longer you stick to it, the easier running multiple businesses will become.

Starting and running one company is already a lot of time-consuming hard work, so when you’re running two or three, it’s pretty easy to feel like you’re barely keeping your head above water in trying to keep up. Remember to stay calm, protect your assets, delegate whatever work you can, and keep to a schedule. As long as you’re organized and willing to put in a few extra hours, you should be able to give each business the attention it needs to thrive.