AMA with expert freelancers Samantha Anderl & Andrea Wildt, creators of Harlow

Jimmy Daly
March 7, 2022

Welcome to our AMA with @Samantha Anderl and @Andrea Wildt! they're the creators of Harlow and have spent time as freelancers and marketing execs in their careers.

Harlow helps freelancers run their entire business, from proposals and contracts to task management and getting paid. Samantha and Andrea know this space really, really well so hit them with questions about growing your freelance business, finding great customers, the importance of contracts, how to manage your workload, how to get paid fast and anything else about freelance life!

Do you have a link to the list of proposal and contract templates that you offer? I'm really interested in checking out Harlow!

Andrea: We don't yet, but we hope to build out an external template library some time soon. We're just launching our beta program now and hope to be live very soon!

What customer acquisitions methods are you seeing most successful for freelancers and small agencies in the biz in this day and age?

Samantha: First, there are a ton of communities popping up to connect freelancers to gigs and vice versa - obviously, we are in one of them (a stellar one).

Secondly, build your referral network, start connecting with other freelancers - recommending them out when you have the opportunity and making intros for them, so they can do the same for you.

Third, build out your social channels - put what you're offering out into the world. Hype yourself, don’t be afraid to tell people what you do and openly say what types of clients you’re looking for.

Also, a couple of pieces of content related to finding freelance work and building your network if you're interested! How to Find Freelance Work
How to Build Your Network

As you may already know, freelancers are always looking for consistency.
So - any thoughts on that?

Can you share some more about how you partnered with freelancers at Campaign Monitor (and are you using those same tactics at Harlow)?

Samantha: I was head of Marketing at Campaign Monitor at the time and while we had a stellar in-house team, we knew the best way to grow production, quality and get additional perspective was through hiring freelance talent.

We partnered with freelancers at Campaign Monitor across the board in marketing - design, content, paid.

And yes! We've actually been building Harlow for the past year with Andrea and I as the only FTEs. We've used freelancers and agencies for dev, content, social, design, brand and more!

Also, an entire post on why we chose to build Harlow using freelancers here - Why We’re Building Harlow Using Freelancers

What is the number one piece of advice you would give to someone starting out with freelancing?

Samantha: I love this question. I always tell people to start by putting yourself out there. Reach out to your network, previous peers and colleagues, your family, your friends - whoever it is.

Tell them what you're doing and who your ideal client is. You never know who is going to have a potential client or two for you. Leaning into your network in the early stages is so important.

Andrea: I'm going to lean into this from the business side of things. I think its so important to do the upfront work to set your business up correctly. I didn't do this the first time I freelanced and deeply regretted it. What I mean is:

  • Set up an LLC & get an EIN
  • Get a separate bank account for the business
  • Find a good accountant
  • Have a consistent process for invoicing
  • Don't forget to pay your quarterly taxes

Samantha: Also, we put together a post recently with advice from 20+ experienced freelancers going over their #1 piece of advice.

I know a lot of us in this community are hybrid full-time in-house folks who freelance on the side (primarily for additional income, but the exposure to other content operations is also great). Do you have any advice for how to manage that workload, avoid burnout, and how to achieve a balance with both?

Samantha: I have actually had a myriad of side projects while working full-time jobs. At one point I ran an online clothing boutique on the side, at other points in my career I was helping friends launch their businesses and assisting them with strategy and marketing.

I'll say for me, it was helpful to block time off my calendar during the day for these projects. Just 30 min to an hr here and there so it wasn't like I was fully checking out of work for the day, but was giving myself time to focus.

And I honestly don't see anything wrong with this, as FTEs we deserve breaks during the day to focus on whatever we want to do outside of work (I truly believe the 9-5 isn't reasonable and should be a thing of the past). Whether that's taking a yoga class, or catching up on a side project - it's up to the human.

Overall, I think it's about managing your schedule in a way that works for you. It worked for me to take 30 min-1 hr breaks during my day to shift focus. Maybe it works for you to block an hr every morning prior to work to get side projects done.

But blocking that time proactively keeps you from having those late nights and feeling of dread that comes with not knowing when you're going to get things done.

Also, you have to make sure you're giving yourself time for the other things that help you combat burnout too - self care, relaxation, working out, social time - whatever it may be for you!

I would love to hear how content marketing managers in-house can get more value from their freelancers, and also how they can be better partners to their freelancers in return. I feel like the second half of the question doesn't get touched on enough.

Samantha: Also! @Jimmy Daly did an interview with us recently on hiring freelancers here.

How often would you recommend reassessing your rates? For instance I set my rates in January (I'm new to this) when might be a good time to assess if I should bump them up?

Samantha: This is super timely, we just published a blog post on this yesterday! When to Raise Your Freelance Rates

How have you seen freelancers productize their services, so they can scale their business without adding more deliverable work to their schedules?

Samantha: I am definitely seeing a larger number of freelancers packaging up courses, templates, coaching services, and more to diversify their income streams and monetize things that aren't tied directly to their time (which we all know is a finite resource).

I'm also seeing freelancers leaning on VAs, editors, designers, and more and building out their mini team to be able to offer a more robust package of services, without having to take on all of the additional work involved.

Sometimes I think this allows everyone involved to charge more for their piece of the work because you're selling more overall value to the client.

I find as a freelancer I'm normally working in the client's systems both in terms of workflow tools (e.g. one client gives me a Trello board, one gives me AirTable, etc.) and payment (e.g. some clients want to use PayPal, some do wire transfers). How are you thinking about that when you're building Harlow?

Andrea: I don't think there is an easy answer to the workflow tool issue. We struggled with that a lot when we were consulting and in order to balance everything I found I had to put everything into our workflow tool (asana at the time) in order to get a complete view of our business. For now, we've taken that approach with Harlow, but I do think integrations with standard tools to pull in your tasks from various systems into a single view would be fire.

As for payments, we are payment agnostic! Harlow will create and send invoices, but you can use whatever payment method you want.

What's your take on freelancer marketplaces like MarketerHire? i've seen them mentioned around more recently as a higher end freelancer marketplace.

Samantha: I'm a big MarketerHire fan. I think these marketplaces can be really helpful to connect companies to freelancers and freelancers to companies in a seamless way.

Especially helpful for larger companies who want to hire freelancers, but have more rigid guidelines to follow.

I think they do a lot of work to help set expectations for both the freelancers and the client up-front.

How do you 'sell in' to prospect clients the idea of value based/flat rate pricing versus hourly? I have a lot of prospects asking me my hourly rate, which I don't use anymore, and have found that most of them ghost me after that.

Andrea: For us, we found that the more we were able to package up our services and really showcase the value we were providing instead of just the tactic, the easier it was to get away from an hourly rate.

For example, instead of offering 4 blog posts a month for $X. You would offer 4 blog posts a month, which includes research, editing, revisions, SEO recommendations, etc.

All of that is what you would be doing anyway, but communicating the true effort involved and making it clear to the client that the work you are doing is so much more than just writing, helps set expectations and helps them understand the value your work is delivering.

I also think if you can give examples of how your work impacted the bottom line for other clients, that is hugely valuable.

As for the ghosting. I hate that! But also, it makes it clear that they’re probably not a good fit for you.

This is a question about outbound strategy for freelancers. What's your process for identifying the right titles (especially in larger companies) to reach out to with proposals for work?

Andrea: After about a year of freelancing we really figured out our niche and that makes this process so much easier! We were selling into B2B tech startups so we we knew we wanted heads of marketing at companies that had just raised a strong seed or series A. Once we had that, the process of identifying the actual names was pretty easy through linkedin.

As for outreach. I highly recommend engaging with these people on social prior to making a purely cold outreach. Follow them on twitter or linkedin. If they are active, comment on posts, and share their content. That small connection can go a long way.

Samantha: Building on that, here's a recent example of an outbound email I received where the person really did their research, and connected with me on social first.

What is the best way to ask for retainer work and minimums before you start working with a client? How to phrase it without sounding rude.

Samantha: First, you're running a business and offering a specific set of services that are set by you, with pricing that aligns with that.

You presenting your services should never be mistaken for rudeness :). And you shouldn't think about it that way either!

The best way to align up-front is to take some more time during the proposal phase of the project and clearly outline what you offer, how you charge, and overall how you work.

Getting this alignment up-front alleviates having to have the convo after work has already started.

AND if the services you offer and the price you are charging don't align with a particular potential client because they didn't budget for minimums or a certain retainer, it probably just isn't a good fit.

I'm curious where the name Harlow came from! Can you share?

Andrea: Freelancing can be lonely! When we thought about building the brand we really wanted it to have an empathetic and human quality to it, which is why we wanted a gender neutral name.

Additionally, we want Harlow to be more than just a software tool. We want to help freelancers connect with each other and succeed by creating useful resources, and amplifying their voices.

Samantha: This blog post gives a little more insight into how and why we created Harlow.

At what point in your freelance journey do you outsource/sub contract your work and work out pricing so that you're paying the subcontractor fairly but not ‘losing out’ either. How do you manage this communication with your client, and have you found this strategy helpful as you've scaled?

Samantha: I think the point in your freelance journey is different for everyone, but Andrea and I started subcontracting almost right away.

How we positioned it to clients:
We're a small team. Andrea and I both work on strategy and execution, and then we have a couple of other team members who you likely won't meet, but they help us get things done for you on the back-end!

Most clients didn't ask questions and just gave us the thumbs up!

And we used project-based pricing which helped us capture the cost for subcontractors while also letting us still pull the dollars out of the project that we wanted.

Subcontracting was the #1 thing that allowed Andrea and I's consulting business to scale to the level it did.

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