The tools available to internet builders today make it easier than ever to take a portfolio approach to entrepreneurship.

The “side hustle” is nothing new, but the idea that you can have multiple side hustles is new. Internet businesses and automation tools make it possible and enjoyable to start and run multiple companies.

The path to 100 customers each paying you $100 every month is littered with obstacles. Reaching and surpassing this goal may require launching more than one business. Increase your odds of success by being a parallel entrepreneur.

This is not a new revelation. Investors make multiple investments per fund. They diversify across industries and stages of growth. Entrepreneurs can do that too.

There are a few high-profile examples and countless other lower-level ones. While each founder paved his own path, there are some common patterns.

A typical approach is to start a company while you’re at your day job. There are some risks but you can mitigate them by choosing a business that doesn’t compete with your employer. Never use your employer’s resources for your side business. And read the legal documents you signed when you joined the company. Legal awareness is key.

A riskier approach is to quit your job and then start businesses. It’s probably not necessary, but if you must do it, remember that it takes at least 18 months to make a livable income.

Regardless of the outcome, you’ll benefit by acquiring new skills that will transfer to your day job. You can explore a new career or make a transition to it, ultimately shutting down your venture and seeking employment at a company similar to it.

The time you put into parallel entrepreneurship will boost your confidence, improve your skills, and ultimately increase your salary, whether it’s at your current company, your next job, or by gaining some extra income on the side.

Luck is always a factor, too.

“Sometimes you can do everything wrong and still succeed,” Diane Baxter, my CFO when I sold Scripted, told me. “My first startup did over 100 acquisitions. We learned as we went. I’ve seen other companies that had great teams, great approaches, and it just took too long and the investors wore out and new money was not available.”

Some companies, despite having everything going for them, ultimately fail.

It takes a lot of time and hard work, and likely more than one company, to get lucky.