Judson Lester Freelancing Interview

Judson was one of the first to heed my call to answer some questions about freelancing. I am very thankful he did, I think you’ll enjoy this interview!

Judson Lester is the co-owner of Logical Reality Design, a software consultancy focusing on the web, and specifically web applications. At its peak Logical Reality Design was 10 developers, and fostered an ethos of diversity and mentoring. LRD is not accepting new work at the moment.

These days he is grousing about Go more than Rails.

How long have you been freelancing for?

I was freelancing for more that seven years.

What services do you offer?

LRD is a web application shop. We did a little CRM work, but mostly because that tended to be a part of any serious web product. Clients who needed more than what a stock WordPress install could do didn’t need us. While there was always a strong web component, the distinguisher for our projects tended to be some sort of interesting backend. Always a database, but usually some sort of data processing engine. As a for instance, several of our clients were “a marketplace for…”

In addition, we did a lot of ancillary services. We managed web hosting on AWS, arranged domain registration and certificates, dealt with payment gateways, etc. etc. While we declined a number of projects, once we were on a task I don’t know that there was anything work we said “we can’t do.”

What did you do before freelancing?

I worked various salary jobs. I was at a university for a while in New Orleans, doing a split between desktop support and systems administration. I worked at a movie studio managing the marketing websites (which were all contracted out to Flash shops). I was at a startup dealing with operations and releases. A bit of everything.

Why did you decide to take the plunge?

The startup got acquired and I didn’t want to commute 90 minutes to work at Qualcomm. My friend had been sole proprietor at LRD and invited me on.

How would you describe your first three months as a freelancer?

There was a lot of spreadsheeting to record hours. I was very fortunate to have an established business to join, instead of having to find the first few clients myself.

When you worked for LRD, was it remote or office space near you?

We were a distributed team, although the partners each maintained a larger in-home office that we encouraged folks to come and co-work in. We were starting the process of finding more “official” digs in our last year, but nothing quite panned out.

If there was one bit of advice you could tell your pre-freelancer self, what would it be.

First, you tax situation is going to change a lot. You cannot “hope that turns out okay.” I spend 5 years paying off the taxes I should have been setting aside for the first year. On the other hand, the feds were cool about it.

Second, net+15 or walk. Do no work, do not lift a finger for a client more than one invoice in arrears. Put that in your MSA so everyone’s clear (you don’t need it there, but it’s good to get out of the way and contract discussion are a good place for that conversation.) Larger point: you always have to be ready to walk - half of that is gutting out firing some clients or declining some work, the other half is structuring your business so that you can walk away (or have clients walk away.)

Third, run the business first, do the work second. You can get a lot of things squared away once and for all, but they’ll drag out forever if you don’t jump on them with both feet. Your clients will bug you for work down, but only you want your own books in order. Get your MSA, SOW, and invoicing standardized right away. A bookkeeper is cheaper than you think and worth every penny.

Fourth, winter is cold, figuratively speaking. Plan accordingly. Sign contracts in the summer and plan to have steady work from at least Thanksgiving to Valentines.

Apart from unpaid bills, what other things have flagged to you that it is time to walk away from a client?

There were certainly some clients who went beyond demanding into pathological - places where demands for changes and deadlines became completely absurd and it became clear that we needed to call things off. I’m having trouble remembering details, partly because they weren’t my direct client.

Relatedly, we included some terms in our MSA specifically so that we could flag problem clients early. For instance, we put in terms regarding stop-of-work, late payment, and personal liability (i.e. that the signatories were taking on liability for debts to us directly, not on behalf of the their companies) which were none of them deal-breakers to negotiate, but each was a little warning flag. A client who wants a more lenient late payment policy is planning to pay late.

What mistakes do you see fellow freelancers making?

Undercutting on price. Sales is nerve-wracking, but it’s cheaper than working a bad rate. If you’re signing every lead, you need to bump your rate. Consider not just the hours you work on the client projects, but the hours you spend managing business stuff, doing sales, or sitting idle (and really, idle time should be on your projects (ideally saleable products)) when you compute your effective rate, and then back-compute the hourly you need to be making.

What one thing have you been doing way more of than you anticipated?

Sales, even indirectly. Again I was fortunate (and also mistaken) that my partner did most of the direct sales (mistaken: I should’ve been doing more of that). But we did a lot of open-source work and went to local meet ups as a way to make our name. That was effective (because people in the tech community thinking of you when someone asks can be gold), but we were slow to realize that we should be doing presentations at meetups where our clients would be. Those are tougher to find and get into, but the payoff is much higher - you have to do both.

Have you had to do much marketing to attract new business?

Yes. The most effective was speaking in public. We put a lot of effort into our website, which I think ultimatly we should have economized. People who were already strong leads look to see that you have a website. I can’t remember even a strong lead who saw our website (and therefore: or who saw a web ad). All of our deals started via word of mouth. You cannot network enough. I think that’s even more true of lone freelancers where the greater proportion of their work comes from a manager asking their employee “hey, do you know anyone who would be good for this?”

Can you see yourself working for a company again in the future?

Well, here I am, and happy about it. On point, though: I wouldn’t say “never again” to contracting.

Is there anything else you would like to say on the topic?

There’s a lot to say about the tech industry in the large that freelancing/contracting reflects somewhat. I think maybe we should have a professional organization, and some kind of licensing - that would be good for freelance consulting work, honestly. I think as an industry we’ve ceded the responsibility of vetting our skills and knowledge to recruiters, which is a really broken alignment of incentives. Likewise, I think we’ve abrogated a responsibility to teach, to formalize our craft, and that’s to our detriment.

Thanks Judson!

Thanks so much for taking the time to speak to me.