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From Solopreneur To Company: How To Scale Up Your Organization

  • Joe PawlikowskiJoe Pawlikowski

If your business isn’t growing, it’s dying. So says conventional wisdom.

But every year, thousands of entrepreneurs prove that trope false. Their businesses, although not growing, are perfectly profitable. And as long as the money keeps flowing, those entrepreneurs are content to keep doing what they’re good at.

Yet there comes a time in many solopreneur’s lives when the urge to grow calls. When you hear it, your next question is obvious.


Scaling up your organization, especially if you’re a solo entrepreneur, can be a scary proposition. But rest assured, it’s been done. Follow these proven principles, and you can discover your own path to growth.

Positioning for Growth

For a small company, growth requires fundamental change. As the head of the company, your responsibilities will change drastically.

You know those day-to-day activities you perform right now? Forget about them. Your focus has to move 100 percent to growth tasks.

What are growth tasks? There’s a good definition in Steve McClatchy’s bestseller, Decide. He identifies two categories for tasks: Prevent Pain and Gain. When you shift to growth, you’ll need to focus on Gain.

Prevent Pain tasks ward off annoyances and other consequences of failing to complete them. If you run an e-commerce store and forget to update your Google Shopping listing when changing product details, you might experience the pain of being de-listed temporarily. If you don’t change sale items back to normal price by a certain date, you’ll experience the pain of lost profits.

Gain tasks push you towards growth. Unlike Prevent Pain tasks, they have no deadline. No one will notice if you don’t do them. Developing and executing a promotional content strategy for that e-commerce store is a Gain task. You don’t have to do it, but doing it successfully will expand your store’s exposure.

“'If you're an entrepreneur seeking growth, your entire day should be filled with tasks that focus on Gain.'”

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That means off-loading routine, day-to-day tasks. They’re only going to distract you from the Gain you pursue.

Going for the Gain

If you don’t have a staff, or if your staff is already working to capacity, how can you do this? (After all, if you were ready to hire staff, you’d have done it already.)

One useful solution might surprise you. Tim Ferriss, author of the bestseller The Four-Hour Workweek, brought the idea of virtual assistants to the mainstream. But the industry has changed significantly since he published that book in 2007. You wouldn’t hire one of his assistants to handle your day-to-day tasks – and thankfully you don’t have to.

The modern trend of business-grade virtual assistants can provide the help you need while you make the transition to a position of growth. Sandra Lewis, CEO of Worldwide 101, discussed how business-grade virtual assistants can assume your day-to-day tasks (with some training, of course) while you remain focused on the big tasks.

As a result, your effort becomes even more valuable.

“'Instead of constantly preventing pain, you're pursuing gain. That's the first step on your path to company growth.'”

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Of course, in most cases virtual assistants will be a temporary solution. If your company is seriously bent on growth, eventually you’ll have to hire staff.

Finding a Hiring Balance

Wouldn’t it be nice if you could temporarily focus on growth, hire some virtual assistants to help with day-to-day work, and then go back to your solopreneur ways afterwards?

Sorry, that’s just not in the cards.

Once you achieve growth, you’ll need plenty of help handling everything that comes with a larger, more profitable company. In other words, you need to hire a staff.

The mere thought of doing so can stop a solopreneur in her tracks. But it’s a concession you’ll have to make if you’re serious about growth.

If you expand your business without hiring and training employees, you might not properly deliver to customers or clients. This means you need to hire employees before you need them at full capacity.

At the same time, if you hire before you start to grow, you’ll be bleeding money. Having employees trained and prepared is essential, but having them trained and prepared prematurely drains you of much-needed funds.

Where’s the balance between the two? The exact point will vary from business to business, but here’s some general advice:

  1. Before you start the hiring process, define all the tasks you need done. For instance, don’t say you need to hire an SEO expert. Say you need help with building links, reaching out to influencers, and ensuring on-site code is optimal. You might find that one person is best for that, or you might find that one person is best handling links and outreach, while someone else is better for handling on-site issues. Perhaps that person can handle analytics or other on-site duties as well.
  2. Avoid the temptation to hire freelancers off sites like oDesk. This applies to the virtual assistant appointments mentioned above as well. You might be able to find some cheap help on oDesk, from someone who looks A-OK. But consider the many oDesk horror stories and think again. There’s just too much at risk for your company to make cheap help worth it.
  3. For most small companies, the best way to start the hiring process is reaching out to contacts and getting referrals from trusted colleagues. Even if nothing comes of those leads, you at least started out on the right foot. If you get to interview a few of them, you’ll get a better sense of what you’re really looking for in a candidate.

No matter how you approach hiring, doing it for the first time will give you a level of stress you’ve never felt before. This is natural. You’re giving up control of something that’s incredibly important and valuable to you – something that’s almost part of your identity.

But the fact is, you can’t do this on your own forever, and that’s a good thing. Focus on the positive aspects of growth, and ceding control will become a little easier.

Forget “Hire Slow, Fire Fast”

If “grow or die” is first on the chopping block for old business tropes, “hire slow, fire fast” isn’t far behind it. Perhaps the sentiment is correct. You should take the time to find the right person, and shouldn’t waste too much time trying to turn the wrong person into the right person.

But this phrase has a few glaring issues.

  1. You’re hiring human beings. To give them a job one day and fire them two weeks later, without clear and compelling evidence that they’re just not doing the work, is irresponsible on your part.
  2. There is such a thing as hiring too slow. One trope that never gets old: don’t let perfect be the enemy of good. The “perfect” candidate does not exist, because the perfect candidate, in your mind, is you.
  3. Firing fast is often more a reflection of the person who made the hire than the employee.

Before you hire people, you need to learn how to hire. Read stories like Danny’s. Devour books about hiring. Ask colleagues who have hiring experience. You won’t truly learn until you do, but this baseline education gives you a head start and will let you avoid basic hiring mistakes, the kind that often lead to firing someone not long after hiring.

If there is one principle I can impart from my own hiring experience, it’s to trust your gut. Even if your gut isn’t always right, you can learn from what it told you and how it differed from the actual result. In other words, you can calibrate your gut over time. The corollary: always sleep on it, so you can add some distance to your gut’s initial reaction.

And one more principle: always ask for references. That should go without saying, but I’ve seen plenty of bad hires who would have never gotten the job in the first place if someone had just called their references.

Explore Mergers

No matter your industry, there are small companies just like yours. Maybe they’re direct competitors. Maybe they provide similar products or services, , but to a different group of dedicated users. In either case, these small companies represent opportunities.

“'The quickest way to stimulate growth is to merge with another company.'”

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You might not like the sound of that. Your company is your baby, your pride and joy. You hate the thought of sharing it with anyone else.

But no matter how you approach growth, you’ll have to share your company. Early start-up employees typically look for equity in the company. Even if they don’t, you’re still handing over decision-making powers to them. Mergers are just a larger step in that direction.

Mergers work on the surface because you take the people, assets, and clients and customers of two companies and combine forces. Where you previously had one employee, yourself, working on four clients, you now have a team of eight working on 20 to 30 clients.

But more importantly, the merged company benefits from all of the previous companies’ relationships. If you worked closely with a top shipper, and the new company worked closely with a top distributor, you’ll have a stronger overall entity after the merger.

One note on mergers is that, in my experience, they work best when the companies aren’t exactly in harmony. In the last one to which I was party, we had just a few people working on a handful of high profile clients, while the other company had a lot of employees working on a huge number of lower profile clients.

If you have great industry contacts and another company has great employees, you might find a fit. In general, you can look for balances of strengths and weakness among:

  • Employees
  • Clients
  • Assets, such as proprietary software
  • Industry contacts and relationships
  • Vendor relationships
  • Technology

If you find that you’re strong where similar companies are weak, or vice versa, you could explore a merger as a fast and effective growth tactic.

Know When To Apply the Brakes

Not only is “grow or die” an outdated trope, but it’s dangerous when taken literally. No company is poised for perpetual growth, not even the huge companies listed on the Dow Jones Industrial Index. Perhaps there is some outlandish expectation that they’ll always grow, but the reality is that they won’t.

More importantly, companies that try to perpetually grow will only damage themselves in the long run. Knowing when to apply the breaks is just as important as knowing when to step on the gas.

Professor Edward Hess of the University of Virginia’s Darden School of Business discusses these issues in his phenomenal course Grow to Greatness. He stresses the importance of knowing when to back off and let the company continue at its current level.

Why purposely stop growing? Plateaus give you the opportu to assess your company in a sober light. How did the growth plan work? Is your company truly in a better position now, or is it just a larger-sized mess? It’s tough to ask these questions during a growth phase.

Once you’ve assessed your company and where you currently stand, you can better plan for future growth. The lessons from the previous growth period can serve as a guide as you again press the gas pedal. Perhaps this time you won’t press it all the way to the floor, or you’ll wait until you hit certain milestones.

Will You Ready to Grow?

For small businesses, growth is rarely, if ever, on that unicorn-like, hockey-stick-shaped curve. It’s more like a set of stairs – unevenly spaced and ragged stairs at that. And that’s for the lucky ones.

Businesses that aspire to reach that next stair have to be careful. Without a solid plan rooted in focus and discipline, a new level of growth might not be attainable. Worse, the business might not be positioned to handle growth when it’s achieved.

Working deliberately towards a goal of growth, from managing hires to knowing when to apply the brakes, will make growth easier to manage for any small company.

What’s the first step you would take to growing a solo company into something bigger? Let me know – and let me know any other growth idea you’ve gotten from this post – in the comments.

5 thoughts on From Solopreneur To Company: How To Scale Up Your Organization


Love this post! My growth has definitely felt like a ragged staircase. It’s difficult learning to let go, especially having seen that doing so often results in things (and prospects or clients) falling through the cracks. I’ve done my best to make up for it when it happens and am learning how to better put in safeguards during transition periods. On the other hand, working with VAs and subcontractors has also allowed me to serve more people and to bring in the talent and experience of other professionals, and that creates a great environment for me and for my clients. My number one tip for others who are looking to expand is to find a VA who will work hourly and just dip your toe in with outsourcing the most mundane tasks. Every hour you save can be put toward a “gain” activity. And you’ll see it isn’t so scary to let go of some stuff after all.


I should say that this is a wonderful post with a lots of insights. Thanks for putting it up Joe.

I was running my company solely for the initial 2 years. But then there came a time where I just couldn’t deal with all the overwhelming tasks all by myself AND I found it to be a problem for me that I was unable to maintain the work-life balance.

It appeared that I was working ALL day and some night – I immediately realized that this is NOT what I wanted, and that I will crash land soon (both in terms of my health and family relationships) if I continue this trend.

So I decided to hire an assistant. And I was lucky to find one of my family members to join me in-house. Initially, the decision making part was a lot of stress, as you mention. I was afraid to give away certain details and responsibilities (that too to a family member – I don’t know what I’d have done if it was an outsider lol).

But now, I find myself so lucky! I have extra hands. I pay him. And I’m not bleeding money as of now. I guess I was also lucky to hire him at the right time!

So yes, pursuing growth 🙂

Joe Pawlikowski

That does sound like great timing indeed, Jane. I’m also glad to hear that hiring a family member worked out. I’ve heard too many horror stories of family businesses gone awry.

Carol Tice | Make a Living Writing

Great post. I’ve solved the VA problem by hiring from within my own membership community, and mostly hiring US-based people.

I believe you get what you pay for, and the problems are far less if you simply hire nearby. My webmaster actually lives on the same island I do. You can feel pride that you’re helping your local economy — and there is plenty of affordable help available everywhere. College students who’d love to work for you instead of McDonald’s. College students who need internships and projects. Be creative! And skip the lost-in-translation hassles.

Joe Pawlikowski

Thanks, Carol. That’s great that you can hire within your membership community. Any way you can get a VA you can trust is key.

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