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How to Freelance Like a Pro with Brian Speronello

How to Freelance Like a Pro with Brian Speronello

A sustainable freelance career requires you to balance stability with growth. Think of that balance like a barbell. 

Half of your time should be spent on your retainer clients that bring you a guaranteed income. The other half should be spent on riskier projects where you charge higher initial rates or negotiate a stake in its performance. 

The steady work is how you pay the rent, but the risks are how you get to the next level. That balance doesn’t just apply to how you should divide your clients, but how you break up your time between billable and non-billable hours, and current work and future work. 

Freelance Like a Pro founder and freelance copywriter Brian Speronello has spent a decade managing that balance. In this episode, he gives us his tips and hard-won lessons.

Show Topics

  • Use a barbell strategy for your projects
  • Freelancers have to know how long things take
  • Set retainers for a maximum amount of hours
  • Ask for the last invoice month upfront
  • Exchange your time and focus for referrals
  • You need some non-billable hours

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Key Takeaways

03:34 – Use a barbell strategy for your projects

A good mix of consistent, guaranteed projects with higher-risk ones allows you to grow your income a bit while not worrying about making rent.

“I try to spend about half of my time on stable, constant retainer work, because that brings in guaranteed income every single month. And that takes away the stress of, can I pay rent? Can I afford groceries? Having that nice baseline, a considerable amount of money that allows me to live a good lifestyle, more or less on autopilot is good. But at the same time, retainers are great in the sense that it provides stability and it provides recurring income, but they provide you with a floor, but that floor can also be a ceiling because you can’t really grow. Part of the deal with the retainer is the client is booking you at that rate ongoing. So if you were to sign a retainer and then turnaround two months later saying, Hey, I’m raising my rates, that would probably turn them off a little bit. So the retainer time is my stability time. And then I use the other half of my time in my growth projects. So those are things where I would either just charge a high initial rate or maybe get some sort of stake in the upside: royalties, performance bonuses. And because I have the stability on the retainer side of the business, it allows me to go take bigger risks, throw more Hail Mary passes because if they don’t pan out, it’s not like I need that sales letter to convert and earn me a commission, or I’m not paying rent.”

11:22 – Make sure you have six months of savings

Brian freelanced as a side gig for five years before he made the leap to full-time freelancing. He had a tripod strategy for making sure he was ready to quit his day job.

“It was five years into freelancing and I actually had to what I call a tripod strategy for deciding when it was time to make that leap. The first leg of the tripod was having six months of savings in the bank. And that was savings calculated based on what I would need as a freelancer. So in the U.S. health insurance costs go way up, if I’m going to go to a coworking space, other business expenses. So before I even left, I projected and figured out what those costs would be and made sure I had six months at that runway rate in the bank. And that’s the first thing. And I know a lot of people are like, oh my, six months would take forever. But to me, that’s actually a good thing because if you’re not making enough money on the side that you can’t relatively quickly save up six months of expenses, how do you expect to pay your bills, you know what I mean? The ability to save six months of your living expenses in a relatively short time frame, shows that you’re making enough money, that it will then be sustainable for you when you leave your full-time job.” 

12:33 – Have retainer clients before you leave full-time

Beyond just having savings in the bank before you quit your full-time job, Brian also recommends having retainer clients signed and a pipeline for more.

“The other piece was having two, at least two, maybe three, more leads in my pipeline that I was confident when I left my job would have at least some decent chance of closing. And then the third was what I thought was actually the most creative thing that I did was at the NHL, we got summer Fridays. So I saved up all my vacation days and I told my boss, Hey, I don’t have any travel plans. So I’m actually just going to take off Tuesdays and Thursdays every week this summer, plus we had a half-day on Friday, so that gave me half of my week free. And then I signed a client on retainer while I was taking that time to make sure, I guess to basically test drive what it would be like working for myself for entire days at a time during that period. And I got to sign a client on retainer that I knew would likely be there when I left my job and I could make sure that that was all working for six weeks before I ran out of vacation time. So once all those things were in place, then I could leave. And I left my job with one retainer client signed in the bank already paying, other potential clients in the pipeline, and six months of expenses to fall back on.”

17:40 – Schedule everything on the calendar

Without the built-in structure of a full-time job, freelancers need to find a way to manage their time. Brian uses a calendar to schedule everything, even his meals and sleep.

“The issue I had with a to-do list is there’s no concept of how long each entry on the to-do list is going to take. Write my book and take out the garbage are both the same ‘size’ on the to-do list. But writing a book is a massively different task than taking out the garbage. So for me, being forced to not just say, Hey, I have to get this done, but how much time is this going to take? And how is that going to impact the other things that I have to do? The structure of putting it all on a calendar, at least somewhat estimating the time requirements, for me allows me to notice, Hey, I may have over-scheduled myself here because I probably need three hours for this, probably also need three hours for this. Well, that’s six hours and I only have two in this block, so I got to move something around, otherwise I’m going to get to the end of that day and be like, oh my God, there’s so many things that I didn’t finish that I needed to finish.”

20:32 – Freelancers have to know how long things take

Knowing how long tasks and projects take is the key to productivity and setting the right prices for your work.

“If you don’t know roughly how long it takes you to do certain things, if you’re not keeping at least some level of insight on your time and keeping an eye on that, to me, there’s no difference between that and a business owner who makes a physical product and doesn’t know what the cost of their goods are, because your time is your biggest cost. So if you don’t know what that cost is, how are you going to properly charge to make sure that you get the margin and the return you need for the hours you’re spending? And blocking out time in your calendar, especially if you go back to like, you block out two hours and something takes you three hours. If you go and you update that in your calendar, that can then become your sort of running record of how much time things actually took. You don’t need a time tracking device. You don’t need to use Toggle or whatever. I personally have a time tracker I really like, but you don’t need that. It can be as simple as putting things on your calendar and then just making sure the calendar reflects what you actually did and at the end of the week just going and checking.”

23:26 – Set retainers for a maximum amount of hours

Some retainer clients have very specific work they hire you for, like 3 blog posts per month. But some clients use retainers to have you on call for a variety of work. With those you have to provide an upper limit.

“We got our go-to person and we’re going to assign them whatever projects are coming up on an ongoing basis and that also ensures that there’s sort of consistency between the ad copy and the page copy and the email copy. And that if one person is overseeing all of that, then it’s okay, that can grow across the whole campaign. So the one downside or the challenge of that is then the only real constraint that you can put on the client in terms of setting expectations is based on your time. So it does become a sort of ‘time for money thing,’ which is not great, but the way I personally handle that is in my agreement, it will say the client has access to me not to exceed a certain number of hours a month, unless we agree in advance. So that means whether I worked zero hours or the full amount, I still get the full retainer rate. So it’s not to go over this amount, but there’s no minimum. So it’s not like if I don’t work this time, I don’t get paid. That last piece of ‘unless we agree in advance’ is important, because then in a separate conversation I will tell the client, this is just a guideline. If you have a big launch, if you have something going on, I will always “agree in advance” to make sure you get the deliverables and the assets you need as long as long as you’re reasonable.”

28:30 – Ask for the last month upfront

The end of the retainer is when freelancers have the least amount of leverage. That’s why Brian came up with his landlord retainer agreement.

“You need to be compensated for that final month of the retainer, which again, most agreements will have some sort of 30 day cancellation policy where the client is responsible for paying that final month. So basically I realized that, I don’t want to call them shady landlords in New York city, but just New York City landlords in general are notorious for basically asking for your firstborn child when you try to rent an apartment. A background, check, a deposit, first month’s rent, and most importantly, the idea that I took from them and why this is called the landlord retainer is they asked for the last month’s rent upfront. Because if a tenant breaks the lease and leaves, they’ve got that last month in the bank already. So it doesn’t matter that the tenant has gone. They’ve already been paid for that. And they can go find a new tenant and their cash flow is fine. So with the landlord retainer, you do the same thing at the beginning of the retainer, the client pays a deposit for the final month upfront. So that way, whenever the retainer is over, even if they go bankrupt, that last month is in your account already. And then you have all of the leverage.”

36:22 – Exchange your time and focus for referrals

Brian has found a way to keep a constant stream of business without having to spend time looking for new clients.

“What I found did work is there is something that your clients, they value it so much, they are willing to pay a lot of money for it. And that is your time and your energy and your effort and your services. So how can you give your clients more of your time and more of your services in exchange for referrals? The way I do it is I tell my clients that my goal is to spend as much time as possible serving them, serving their business. And I try to find anything that takes my time and attention away from them is something that I try to eliminate as much as possible. And that actually includes business development. Because if you think about it every hour, I spend out looking for a new client is an hour I am not spending on your projects right now. I don’t want to do that, but the problem is if I don’t bring in new business, then I don’t get clients and then I go broke and I go hungry. So clearly I need to have that. I do need to bring in new business. So that’s why, what I propose is if you will give me two referrals at the end of this project together, I will not go and spend a bunch of time and being distracted and try and chase down new business. I will focus more of my time, more of my energy, more of my effort on your project in the moment right now. I’ll get it done faster. I’ll be able to deliver a higher quality of work. And again, all I ask at the end is that you give me two referrals, so then I can keep my pipeline going.”

39:24 – You need some non-billable hours

You want to keep your non-billable hours low, but you shouldn’t eliminate them completely. There are high-value things that you need to do outside of client work.

“It’s about 20-25%. And there is a point of diminishing returns, I guess, where every hour you spend working on a client project is an hour you’re actually getting paid. But at the same time, there are things that happen outside of that billable time that allow you to be more profitable. If you do something that raises your fees or that raises your credibility. Joining a mastermind and then attending those calls, that’s time that I would charge to that non-billable bucket. But joining those mastermind calls, doing the networking stuff there has directly led me to increase my rates. So you want to be strategic. The goal is not zero non-billable time, because there are valuable things. The goal is really efficiency and making sure that if you’re not doing client work, you’re not just sort of wasting your time on low value, low return tasks. But every hour you spend away from a client is really, really high leverage, and it can turn into double or triple your rates for a new day client or something else where it justifies that trade-off of non-billable time versus client work.”

42:56 – Take advantage of masterminds

Brian joined a Copy Accelerator mastermind group that opened up new opportunities, but he had to be ready to learn from others to get all of the benefits from it.

“Investing in a mastermind that I’m surrounded by other copywriters is great, but I wouldn’t get business from that necessarily. It would only be through referrals from other people in the group. I would not have direct access to clients the way joining this mastermind, part of the calculation was not only will I improve my skills, but I will directly interact with many of my top tier clients. And I immediately doubled my rates as soon as I joined and I signed a client at those new rates within a few months. And so it almost immediately paid for itself and it continues to go up from there. And so that to me was the biggest thing. And I was hesitant. For a long time I was like, I can learn it from books. I can learn it on my own. I guess maybe it’s one of those things where when the student’s ready, the teacher will appear, but I finally got that level of humility or whatever, where I can say, Hey, I could stand to learn from somebody else. I don’t need to be doing this on my own. I can take feedback. I can say I don’t know everything. There are plenty of people with more experience. Rather than me being off on an island by myself, let me partner with them. Let me learn from them.”

Listen to more episodes of The Long Game here.

Allie Decker

Allie is co-founder and Head of Client Success at Omniscient Digital. She previously led content initiatives at HubSpot and Shopify.