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I started my online wine club, called Uncorked Ventures about (amazingly) 9 years ago.  Over the years, I’ve hired freelancers for any number of jobs.

Many of my experiences with freelancers have been positive.  A few of them though were frustrating because I felt like the freelancer didn’t have realistic expectations for my small business.

Likewise, I’m sure there’s plenty of freelancing that I could be more understanding about, which is largely how I found this blog in the first place.

I’d like to try and lessen the chances that some of those same frustrations occur for others because small business and freelancers should go together hand in hand.

We should be able to understand where each other is coming from and have a realistic set of expectations for each other.

To that end, here’s some tips for freelancers when working with small business.

1. Understand the Scope of Small Business

According to Quickbooks (I assume these are the folks that would know, right?) here are some relevant statistics about small business:

  • 80% of small businesses have zero employees
  • 50% of small businesses are home based
  • The average revenue of small businesses (revenue, not profit) is $44,000

I assume for many freelancers, those are rather sobering statistics.

Small businesses are often, much, much smaller than most people realize.

In fact only 1 in 11 small businesses has 6 figures in revenue in any given year. That’s something that I realized a while back, I switched shipping companies from Fedex to UPS because of pricing (namely the cost of having my packages picked up, Fedex charges per package and UPS charges a simple 1 time fee).

When I left Fedex I was told by my rep, that my business, at that point struggling to make ends meet, was her largest account. I was and continued to be shocked.  I think most freelancers would be as well.

2. Payments Have to Work for Both Sides

I recently saw an article about some suggestions for freelancers.  Part of the article suggested not only a down payment, but also a 50% payment before the work had been begun. If you’re only think of the process from a freelancer perspective, makes perfect sense right?  

Ask yourself, if you’re a small business owner would you be willing to accept those same terms?  Would you pay 50% before any work at all had been delivered? From someone that you found on a random website –   On a website that you had never done any work with before?  Doesn’t sound quite so appealing right?

I don’t know exactly how to structure payments so that they make sense for both sides.  I think it’s pretty clear that paying a significant percentage up front is awesome for freelancers, but not as interesting for a small business owner.

If you’re looking for a long term project, then setting up a series of milestones that correspond to dates of delivery and then payments makes sense.  If it’s a smaller project than someone is going to have to take on the risk.  

This becomes easier as both the freelancer and the small business owner starts to build a reputation for themselves.  But, asking for everything all at once, on either side, seems far fetched at best.

3. You Need a Website, With Pricing and Yes, With a Blog

I get it.  Not everyone likes to write.  There’s a ton of useful advice out there that says, you should never, ever share your rates publicly.  But, think about the small business owner that we talked about at the beginning.  

They’re desperate to grow their business, but they’re seriously low on time and money.  What do you think the chances are that if you have a 1 page website, without prices, that they’re going to reach out to you?

Pretty much zero.

Instead, picture a freelancer website, with full pricing transparency, samples of your work, links to independent websites with reviews and a blog showing the freelancer’s work, but also something about the freelancer him/herself.

Who do you think gets the business most of the time?  Who will the small business owner feel more comfortable with especially given that they literally are taking money out of their savings to pay your rate?

Tips for New Freelancers

4. You’ll Both Be Working From Home: Be Honest About It

If you’re a new freelancer, you’re likely to be working from home.  You’re also likely to be making some trade offs because you gave up a guaranteed salary to begin your freelancing career.  

You might have child care issues on a daily basis, or at least when the kids are sick.  There’s sometimes going to be some noise in the background.  

Pretty much all of those caveats hold true for the average small business owner as well.  That’s ok. If we’re honest about it on both sides, we should be able to have a level of care and concern for each other because we understand what the other is likely going through.

5. Communication Is Important and Can Be Difficult

One Freelancer whom didn’t work out so well for me, wanted to chat on the phone. He also had a specific time of day he was accustomed to taking these calls.  10am.  Except he was on Eastern time and I’m on Pacific….so that made for a requested 7am weekly call.  

Don’t get me wrong, I’m awake, I have young kids.  But, my mornings around that time normally involve building puzzles, heating up bagels, trying to control a tricycle being ridden around the house, packing lunches, stopping them from playing in the mud outside, figuring out what to make for lunches, etc etc.

While I would have much, much preferred email as a way to communicate, I can understand the want and need for a phone call. That being said, having a specific time schedule didn’t make the small business owner and freelancer relationship a possibility over the longer term.  

Communication is both paramount, but also difficult. Finding a way to handle it that makes it work for both sides, is essential.

I hope you’ve enjoyed some of my tips and stories.  I really do believe that small business and freelancing should be able to go hand in hand.  

It’s hard, but if we set up reasonable expectations for each other and remember that we’re in largely similar situations, things should go more smoothly.


Written By
Mark Aselstine is the owner of the Uncorked Ventures Wine Club an online business based in the San Francisco Bay Area. A father, husband and lover of all things politics, sports and entrepreneurship you’ll often find Mark on Twitter, arguing about pretty much anything other than wine.

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