Bootstrapped Founder #137: Should Freelancers Offer Free Trials?

Dear founder,

Recently, I have gotten a lot of offers from freelancers and consultants to do some work for me for free.

In an ideal world, we’d offer our services to a prospect, and they’d gladly pay for them. But the reality is quite different: many freelancers have a hard time finding clients, and some have come up with a way of making that easier.

The idea is simple: they help me out for a few days, I get to see their work, and then ask for compensation for future assistance.

Prefer listening over reading? Listen to this on my podcast. There is also a YouTube version of this article.

It’s the “7-day free trial” version for freelancers.

This approach comes with several advantages:

• the freelancer gets to build a portfolio without needing to negotiate contracts
• the freelancer forges connections with interesting people
• you can share your approach in public, attracting more prospects

However, there are several risks involved with offering to work for free:

• free work is unpaid work, even if you eventually get hired
• you’ll have to work with less than a contract-based freelancer would have access to
• most people don’t value free products or services much
• you might not get honest feedback when the client has no skin in the game

So, is it a smart move to offer temporary work for free? Let’s dive into the pros and cons.

Pro: You’re Building a Portfolio

In a world where millions of small-scale entrepreneurs offer their services, what makes you stand out the most is a portfolio that showcases your skills. Particularly when you’re starting out, having quit your day job, or trying to make headway in a new industry, this often feels like a chicken-and-egg situation: you need a portfolio to find clients. To build a portfolio, you need clients.

Doing free work short-circuits this conundrum: you just do the work without having to convince someone to pay you for it.

In the spirit of permissionless apprenticeship, you don’t even need your client to agree to anything: I’ve had people send me their excellent work in DMs —designs, text fragments, social media strategies— which later led to more long-term engagements.

And for those freelancers, just creating the work left them with something they could share with future prospects. You’re effectively building a proof of your freelancing ambition, a treasure trove of content and reusable frameworks.

Con: You’re Not Getting Paid (just yet)

Of course, doing all of this for free has the major (and very obvious) drawback of not making you any money.

In the short term, this might make sense, as you’re effectively spending your time marketing your services instead of spending money on advertisement or other marketing efforts. You pay with your time.

That’s a perfectly reasonable approach if you actually end up with several clients after doing this for a while. But the risk here is that you burn your time on a service that people enjoy for free but aren’t willing to pay for once you ask for compensation.

Remember: it’s supposed to be a free trial of a service, not a free service. You will need to convert prospects into clients eventually. One of the most important things to be adamant about is to have a highly limited timeframe for your free trial.

Depending on the kind of service and how quickly potential customers can see results, you need to set a limit that allows your prospect to evaluate your output and its impact and not work for free a day longer. “I have spent a week creating content for your social media presence. Your growth is up 50% compared to before. Here’s the contract” — this is how it should go.

I know this feels forceful, maybe even aggressive, but you’ll have to muster that courage. Otherwise, people will gladly keep taking your work for free.

Pro: You meet fascinating people

Now, the fact that it’s free and no-strings-attached makes it extremely interesting to “just try out.” And with that, you can get access to exciting people in your field.

It often takes just a few cold DMs on Twitter to get some initial interest. After all, most Twitter users get a lot of DMs in which someone asks something of them, but very few with a freebie. You’ll stand out just by not putting them in a situation where they have to say no. It’s effortless to say yes to free.

One phrase that always got me to agree to this kind of offer was this one:

“There are no strings attached. You can do with the work whatever you want. After a few days, let’s revisit if this works for you, and if not, that’s no problem.”

This is the highest-performing sales pitch you can employ.

And it will get your foot in the door with people you want to work with. All the people that chose me as their permissionless mentor still have a great relationship with me, even when I decided not to use their service. Instead, I often suggested other prospects or even introduced them to my peers, who I considered a better fit.

This is classic relationship-building. As a freelancer, you show that your clients can trust you and that trust is carried through the relationship network.

This episode is sponsored by Reel Unlimited!

Reel Unlimited makes it easy for busy founders to:

✔️ Request unlimited graphic design tasks and get matched with pro designers who deliver most of them within 24 hours.

✔️ Get high-quality design tasks done for you without worrying about hiring, payroll, and contract.

⚡️The Bootstrapped Founder fans get 25% off for 1 year using the code ARVID upon signing up at reelunlimited.com.

Con: Your “free” clients will keep you at a distance

But this kind of trust is limited.

No contract means no security for either party. That’s not as much a problem for the freelancer, who already knows that there’s a good chance this work will never be compensated. But the prospective client has a whole other risk to deal with: personal information.

Here’s my rule: I won’t hand over credentials to anyone I don’t have a legally binding contract with. It matters less if that’s written, digital, or just a handshake agreement — but if there is no trace of a promise and its scope, I won’t ever allow a freelancer into my operations. This is my source of income and wealth-building. I won’t invite a person into this without first vetting them and having them agree to my provisions.

Knowing this, you have a few options. First, you can just deal with it and make use of the information you get. If you’re helping someone build a Twitter audience, you might not be able to tweet on their behalf, but you can draft their tweets for them in a Google doc. Alternatively, you can craft a contract that spells out your work and its limitations. As your prospect will consider this a professional approach to a professional relationship, this projects confidence. It won’t be enough to say, “oh, it’ll be fine, I promise.” Trust is slowly built and quickly lost. So offer ways for that trust to grow by being preemptive about concerns and reservations.

Pro: Doing this in public attracts prospects

The more you do this, the more people will start noticing. And if you make a point of documenting your journey in public, you can create a very interesting funnel.

Many creators want to help and empower their peers. If you ask your prospect if you can talk about your trial relationship in public, what you’ll help them with and how you approach it, you’ll find that some potential clients won’t mind that — it’s a social media win-win situation.

So build your brand in public. Share your outreach strategies, your thoughts around trial length and pricing, and who you’d love to work with. Who knows; this might manifest the very relationship you seek to establish.

Con: Pricing issues can quickly confuse them

But beware: “free” is not always going to work in your favor, both in your permissionless trial work and in its public communication.

This has to do with the concept of perceived value: if you tell someone the wine they’re drinking is very expensive, it will taste better, regardless of the actual quality of the wine. The inverse is also true: when something is exceptionally cheap —or free— we consider it lower quality.

That makes working for free a risky business: not only do you not make any money, but the perception of the resulting quality might be drastically lower than what people would have thought it to be had they paid for it in the first place.

This leads to a challenging decision: when do you communicate what your service costs after the trial period is over? In my experience, I had people do great work but ask for incredibly high fees after the fact. Had I known what to expect on the compensation end, I’d have evaluated the services rendered differently.

This is a potential breaking point. Trust erosion happens quickly when assumptions turn out to be completely wrong.

Communicate your expected range of compensation early. Best before you present your work, but early enough for the price to put expectations into context. It’s critical to get this right eventually. Depending on what you offer, you might need to experiment with perfect timing.

What matters most is that your prospect always understands that your free work is a little taste, a “this is what things could be like” for a professional and well-compensated relationship later down the road.

Should you work for free?

I believe the pros slightly outweigh the cons for giving your prospects a free trial of your freelance service — with a few limitations:

• Clear pricing needs to come up front. Leaving this to the end erodes a precious connection with a potential client and can only lead to confusion.
• You have to be okay with clients that don’t convert. There is no guarantee anyone will book you, no matter how good your work is. Budgets are usually exhausted the moment people make them. You’ll need to churn through a few losses to take a win.
• If you work for free for months and don’t convert, you need to stop. Pivot to something else, or adapt your offering, but stop for a bit. At this moment, you have to talk to those who said no and find out where their expectations were disappointed.

The point of this trial approach is to market your services so you will get paid eventually. More than that, you want to do this so you’ll never have to do it again: once you have built credibility and a reputation among your initial clients, word of mouth will allow you to skip the free work and get paid right from the start.

A free trial is a trust-building exercise, whether a freelancer or a SaaS business uses it.

Use it as such. Build trust, build a portfolio, build it in public, and increase your opportunity surface.

And then, get paid.

Thank you for reading this week's edition of The Bootstrapped Founder.

If you like what I wrote about, please forward the newsletter to anyone you think would enjoy it too.

Please check out my Twitter course Find your Following. You can find my book Zero to Sold at zerotosold.com and The Embedded Entrepreneur at embeddedentrepreneur.com.

If you want to help me share my thoughts and ideas with the world, please share this episode of the newsletter on Twitter or wherever you like, or reach out on Twitter at @arvidkahl.

See you next week!

Warm Regards from Ontario,

Arvid