Why You Should Never Start Just One Business

There are two types of entrepreneurs: Those who start one company and those who start lots of companies.

Those who start lots of companies like to describe themselves as “serial entrepreneurs,” which may or may not be slightly fatuous. Those who start just one company may think of themselves as “business owners” once the thrill of the entrepreneurial journey has ebbed.

If you’ve started one company, you can do it again. And you probably should. One company is not enough.

I will explain why.

Starting multiple businesses guarantees that life will never be boring.

Let’s face it. Entrepreneurship is a rush. Whereas most people get into business to make a living, I find that a life worth living includes starting businesses.

After having started a few, I want to start more. Running a business is exciting in its own right, and I continue to do so on a daily basis. Starting them, however, has a set of unique challenges and thrills.

Keep starting companies and you’ll never live another boring day in your life.

Multiple businesses can provide financial security.

If excitement isn’t your thing, then maybe financial security is more palatable.

According to CrunchBase, the average successful U.S. startup raises $41 million and exits with $242 million. Notice, however, that is only successful startups. For every one successful startup, there are as many as nine unsuccessful startups. Angel.co puts the average valuation of their startup list (not all successful) at $4.3 million.

Not every startup turns out like Apple ($590 billion valuation), Facebook ($200 billion valuation), Airbnb or Uber. Those companies are the rare exceptions, not the general rule. If you want to sit on a future mountain of cash, you may have to start more than one company. 

Starting multiple businesses allows you to stay fresh.

Every time you start a new company, you learn something new.

In my entrepreneurial pursuits, I’ve launched businesses in industries that I knew nothing about going into. Learning is half the fun of doing, and keeps your mind sharp and your skills fresh.

Not starting another business is a waste of your personal experience.

One of the worst things that you can do with your experience is to let it waste away. Experience is meant to be used, shared and acted upon -- not stifled.

When you have the experience of starting a successful company (or an unsuccessful company, for that matter), you can turn around and use that experience to do it again. Or, you can use that experience to teach others how to do it.

Experience is one of the most valuable takeaways from founding a company.

Starting a business creates a valuable network that makes it easier to start another company.

Another valuable entrepreneurial asset is your personal network. When you start a company, you meet investors, advisors, other entrepreneurs, vendors, service providers and other people who help to grow a business.

These relationships are highly valuable. They enrich you personally and they allow you to create the platform upon which to build more companies.

Starting a network from scratch is tough. The game of who-do-you-know-that-I-can-meet gets old fast. Owning such a network, however, has value that goes way beyond money.

Starting more businesses gives you exponentially more influence.

Revenue isn’t the only thing that grows bigger with more businesses. Your influence grows, too.

Serial entrepreneurs don’t remain out of the limelight long. Because of their experience, they are called upon to share their experience, speak at conferences, participate in panels, provide interviews, and write blogs.

Such influence can be exhausting, but it’s also rewarding. Influence is part of your personal brand, which you can then leverage to earn even more.

The more businesses you start, the better you become.

The first time you do anything, you’re barely hanging on. The second time you do it, you get a little bit better. The third time, you’re starting to develop confidence. The fourth and fifth time, you feel like you’re getting the hang of it.

This is true for starting businesses, too. With every new business, you’re building on knowledge, brand visibility, marketing experience, and other resources, creating a business that is even better than the one before.

Why would you do it only once when you can get better with each successive attempt?

You can build every successive business faster than the one before.

Everything about building a business takes time -- funding, marketing, development, research, strategizing, etc.

These time-consuming activities become easier and quicker every time you do it. You can spend less time finding VCs, writing proposals, searching for vendors, hiring developers, developing a marketing plan or researching your target market.

Each new attempt goes quicker, meaning that you can launch a successful business in just a fraction of the time. Starting only one seems like a definite lack of strategy.

Some warnings on serial entrepreneurship.

Starting lots of businesses is every bit as exciting as I’ve indicated. That being said, you need to keep in mind that there are risks, disappointments and stressors. Let me provide a few disclaimers.

• Beware when starting any business. To be an entrepreneur is to take risk. To live life in general is to have risk. Based on my experience and disposition, I tend to think that to be an entrepreneur is to take less risk than, say, giving your life and livelihood to work for someone else’s company. Entrepreneurship has its own sets of risks.
• You don’t have to break up with your old business. When you start a business, you become deeply invested in its success and future. When you start a new company, you aren’t neglecting the old one. You can still run it, coach it, advise it and profit from it.
• Take a break between businesses. Even though starting businesses is fun, you’ll benefit more if you unplug now and then. I suggest taking a nice, long break between business ventures. You’ve earned it.

Conclusion

The more you start, the better you get. Launching a single business is only the start of a promising and successful future as a serial entrepreneur.

If you’ve started one business, good for you. Now, go and do it again.