3 Signs You Are Ready To Leave Solopreneurship Behind

A few months back, Dom was asked to contribute his thoughts on the 'biggest business mistake' he had made (so far :P) and the person who reached out was non other than Mike Thatcher.

You can read more about Mike below but his expertise is in helping solopreneurs expand their operations and helping them hire the right people.

Letting the founders 'break the systems' and work on what's important to growing the business.

​Anyhow, this is Mike's guest post to you guys about transitioning from a solopreneur to an entrepreneur. 

Being a solopreneur running an affiliate business means you have a lot of tasks on your mind. You run your business as if you had departments under you, but all of the work is being done by one person - you.

If your plan is to grow your affiliate business further, up your revenues and take a greater market share, the odds are not in your favor if you want to do it all by yourself.

As hard as hiring your first employee sounds, other activities such as:

  • managing your growing web site daily,
  • preparing content ideas,
  • handling writers,
  • getting those ads rolling,
  • making sure your SEO is doing well,
  • researching new products,

also, demand a big portion of your time that you can save by delegating.

So, when should you make the leap into hiring someone to help you with all the work?

When Should You Leave The Awesomeness of Flying Solo?

First, know the false signs at which you shouldn't hire.

Hiring a person is a serious commitment, so let’s first address what are the signs showing you are still not ready for it.

  • Stressful moment - It’s your busy time of the year, and one of your kids got sick just in time for it. Or you have an important date coming up that you have to prepare for. Or anything else that life can throw at you. Just because you feel overwhelmed for a week or two, doesn’t mean you should commit to an employee that you should pay for month in and month out.
  • You are not sure who you are exactly looking for - You know you have a lot of work at your hands, but not sure you know what exactly you would delegate. Also, you are not quite sure what kind of qualifications the person should have.
  • Because someone interesting came your way - You met someone who shares your interests and who you think you’d hit off when working together - but, you don’t need this person in your band at this moment. This is a recipe for disaster.

The Right Signals for Hiring

1. You need someone to tackle tasks that will bring money

Paying someone to do unproductive and non-lucrative work for you doesn’t sound right, does it? So, wait for the right moment when you have enough tasks that will truly return on your investment (in their paychecks).

Of course, your time is valuable, too, so delegating to someone whose time has a lower rate than yours does save you money.

However, if you would hire someone to just post on Facebook for you, or do any task that doesn’t directly bring money, it is maybe still time to pause on this.

2. You need a particular skillset on your team.

You shouldn’t be looking for a marketer. You need to look for a marketer with 1+ years of previous experience working on an e-commerce website and can manage a team of three writers.

Only when your vision is clear on the exact employee you are looking for, will you be able to find the matching candidate and get a return on your investment.

3. You need someone to help you with a task you are not good at.

Setting up the bases of the company is always the job of the founder, in your case - you. But, that doesn’t mean that all the hats you have to wear on the job fit you the same.

When you pinpoint the one that you are worst at, but which has a substantial effect on your business, this is the new hire you are looking for.

Contractor or Employee?

To minimize any possible damage this decision can do to your business (put your cash flow in jeopardy, for example), you can start off with a contractor or a freelancer.

Set the job posting for the same skillset you are looking for, but limit to the period you need to decide on the long term hire (for example, three months).

This way, you will also get the chance to polish on your requirements and see whether you need this skill set in the first place.

Let’s say you are planning on hiring a WordPress VA.

A proven method I discovered is:

  1. Determine the scope of tasks
  2. Define the scope of work (weekly hours)
  3. Arrange the payment rate and dynamics

You’d need this person to upload content, format it, adjust any loose ends, run it through Grammarly and copyscape, then make it SEO friendly.

Before that, the VA would negotiate with the writers about the deadline, approach, and price based on the content marketing plan.

In the end, they would fill out reports, get back to you on the stats about the piece and help you with the grunt work for acquiring backlinks.

What we got here is that you need:

  • Basic WP experience,
  • Basic to advanced SEO experience,
  • Excellent organization skills,
  • Reporting experience,
  • Data entry/scraping skills,

Now, it’s important to determine just how much of these activities take up your daily time.

Then, multiple that by a coefficient of 1.5-2 (as this person will need time to get up to speed) and there you have your weekly scope of, for example, 10-15 hours/week.

Depending on the responsibilities you will put on this person, you can set an hourly price. This is important, as you’d want to pay only based on the scope of the tasks.

Hint: Do this analysis before even publishing a job posting - it will help you diagnose just how urgently you need this position after all.

Lastly, you need to consider the payment dynamics. I suggest paying the VA biweekly.

There are two reasons for that. One is that this sort of dynamics will help you regularly keep track of your costs and control them in case it gets out of control (the VA starts logging crazy hours).

And the second is to secure yourself in case it doesn’t work out. You will have more flexibility to react sooner and terminate the contract if it is not working out.

If everything does go well and the scope of work gets bigger - it will be much less of a hassle to transfer this freelancer to your employee list.

You’ve already on-boarded the new-hire!

Now, Do You Think You Are Ready?

Yes? Way to go - good luck with your search and growth!

Keep in mind all the advice given here, and invest your time in looking for the right person.

Hire slow for best quality.

If you are still having your doubts, and need to go over the pros and cons one more time to be sure - that’s alright as well!

It is wise you don’t jump into any decisions that can end up costing you thousands of dollars and broken relationships with some amazing people.


Mike Thatcher is a Digital Ninja with a years' long experience. Digital nomad by the place of residence, he is passionate about entrepreneurship and leading small businesses and startups, especially in the online world. His best work comes to life when working what he loves most - writing.