4 Things Nobody Tells Entrepreneurs About Going From Small Business to Enterprise


When you Google terms like “how to be a business owner”, there’s no shortage of advice to be found on how to start and manage a small business.

And while this is fantastic for entrepreneurs who are just getting started as business owners, what about those who already have a successful business that’s on the verge of hitting the big times? What if you’re already making six figures as a company and now you’re on your way to hitting seven or eight?

The truth is, the transition from a thriving small business to successful enterprise can be every bit as shocking as starting a new business from scratch.

So on that note, here are 4 things that nobody tells business owners about taking their companies to the next level.

1. You’re No Longer Under the Radar

When you’re first starting out as a solopreneur or a small business owner, there’s a period where you’re able to blissfully make money while the big names in your industry tear each other apart.

Think about it.

How often do you see small mom and pop stores in the news for situations where they aren’t the victim? Exactly.

But somewhere during your growth as a company, you reach a point where suddenly the major names in the industry are watching your moves and you’re increasingly being forced to make tactical decisions based on what the competition is up to. 

The worst part about it is that all you can do is wait and be prepared. Because if you’re growing, that day is coming.

2. You Eventually Reach a Point Where You Have to Delegate More 

As a small business owner, you wear a lot of hats. You’re the de facto marketer, manager, product designer, and, depending on the industry, you may even be your own IT department. 

However, there comes a point where it just isn’t feasible to DIY your way through anymore. As a matter of fact, you may need to hire professionals in order to take your company to the next level. 

If you’re the type of entrepreneur who has traditionally been a bit of a control freak, it may be hard to let go and watch someone else manage your brainchild. But when you start reaching that enterprise level, delegating becomes a necessary skill.

3. Your Insurance Needs Change Dramatically

Every company has an origin story. Maybe in your case it wasn’t as dramatic as producing your product in your basement or spare bedroom, but when you’re running a barebones operation, you can sometimes get away with carrying lower amounts of insurance.

But as you hire more staff and sell more products or services, there comes a point where you need more than general liability or commercial insurance. Suddenly higher premiums are par for the course and policies like cybersecurity insurance or D&O insurance don’t seem so far-fetched. 

You’ve heard the expression, “An ounce of prevention is worth a pound of cure?”

Well, as your company’s liability exposure changes as a result of your growth, it might pay to revisit the insurance products and protections you have in place. 

4. You’re Going to Spend More Time Managing People

When it’s just you and a few part-timers or freelancers, it’s easy to set your own pace and dictate your own professional culture. 

But the more you grow, the more you have other people bringing unique perspectives and skills into your company. And as you start going from small business to midsize enterprise, you’re often bringing different personalities into the mix as well.

Even if in the past you could spend almost all of your work day dealing with business matters, when you grow into an enterprise you may find yourself handling personnel more than you ever thought you would before.  


The road from zero to thriving small business isn’t an easy one. In Canada, it’s estimated that thousands of small business go bankrupt every year. And that’s before we start talking about wantrepreneurs and entrepreneurial hopefuls who were never able to get their ideas off the ground.

If you’ve not only kept a small business alive but built it to the point where you’re starting to have enterprise-level concerns, you have a lot to be proud of. Along with that success, however, it’s not unusual to experience growing pains. But as long as you’re prepared and you’re able to focus on the things that matter, there’s no reason you can’t maintain that upward trajectory while achieving dizzying levels of success.