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Small Firm Roadmap Stories: Build the Tech You’re Missing

Lawyerist Lab is a community where solo and small-firm lawyers go to innovate, test, experiment, and improve their law businessesWe’re interviewing Lab members on their experiences as they align with The Small Firm Roadmap.

“People may not realize that if there’s not a technology or software product out there that works for your needs, you might be able to build one. It might not be as expensive or as complicated as you think.”

Tell me about your practice. How did it start? What were you doing before it started?

I launched my practice in late 1999. We focus on trademark law. 

Prior to launching my firm, I worked at the US Patent and Trademark office for about a year as an examiner reviewing trademark applications.

When I decided to launch my practice, I had a couple of thoughts. One: I knew working for the federal government wasn’t for me. It didn’t meet my professional goals. I wanted to be an entrepreneur — get out on my own.

Also, the internet as a marketing tool and platform was really just taking off at that time. When I launched my business, the majority of law firms didn’t even have websites. I saw an opportunity. 

What kind of opportunity?

I decided to charge flat all-inclusive fees from the beginning.

I also realized that technology was changing the way that firms worked and marketed, particularly in a field like trademarks where your practice can be national. So, I built a website, marketed online, and got my first clients. 

What were your struggles when you transitioned to own firm?

Like most solos, I struggled with being alone. I had a huge support network at the trademark office and in school before that, so being on my own was different. At the time, I didn’t have the wisdom to reach out to find mentors. 

Plus, there weren’t a lot of small or solo IP shops at the time because the market was undergoing an evolution. There were no roadmaps to follow. I really had to make my own way. 

You had your practice for quite a while before you joined Lab. What made you join?

A combination of things. Number one, even when things are going well, I’m always looking towards the future. I don’t want to be static or stuck in place. The practice of law is changing. The management of firms is changing. If you don’t keep up, you’ll get left behind.

Second, I had become tired of going to traditional conferences in the field. You’re surrounded by people who practice in the same field and they have the same type of lectures every year. I was getting so little out of going to those conferences that I wanted to try something new.

I wanted to think out of the box and make fresh connections. And Lab has been so valuable for this. Even if other attorneys in the group are working on different issues, I still get value out of hearing their stories, their obstacles, and how they overcame them.

What else do you find helpful about Lab?

When I was ready to grow, I had no idea how to handle staffing. I had zero experience or training in managing, overseeing, hiring, firing, all of that. To have support and coaching in Lab while I figured all of it out was really important. 

It’s also great to be around like-minded people — attorneys who are thinking differently about subscriptions, billing, staffing, processes, and everything else. Even if we aren’t working on the same issues, just hearing their solutions and stories is so helpful.

The Masterminds [peer-led brainstorming groups] have been tremendously helpful. Being around other people who are sharing their experiences and challenging each other and asking questions and learning is so valuable. 

Finally, one-on-one coaching with Stephanie. I’ve been working on a book, and she’s kept me on track. She’ll ask me questions like, “You finishing that book today? No? OK, what’s keeping you from writing? What’s the struggle? How do we fix the jam?” I can make a list of a hundred things to do, but it’s hard to do them without accountability. 

What’s one area of The Small Firm Scorecard where your firm is doing well? How are you maintaining that growth?

Technology. We’ve always been ahead of the curve there and we’ve kept the progress going. 

Going paperless is huge. You would think it’s not something to brag about anymore, but you’d be surprised. You’re still ahead if you’re paperless. And if you aren’t paperless yet, make it a priority as it opens up so many other doors with efficiency. 

I’ve also found that people may not realize that if there’s not a technology or software product out there that works for your needs, you might be able to build one. It might not be as expensive or as complicated as you think. We built our own product that works as a CRM, an intake, and our docketing system. It’s invaluable. A bonus benefit is that it is a great marketing tool when I tell prospective clients that we’ve built our own proprietary software.

If building a new tool feels daunting, talk to an expert and break it down into pieces – maybe your tool only needs to do one thing to start. What’s one very repetitive task you need help doing that you can’t find the right tool for? 

What’s your advice for someone starting their own firm?

Number one is to find a passion that you can tie into your work. I don’t believe in the separation of work from life. For instance, if you love sports, try to work with sports companies. If you love music, go to music events and network and promote your services that way. Combine your passion and work in every way you can. 

Second, have patience. I used to say, wait six months for progress — and even that’s probably generous. But when the returns start to come in, the results can be contagious. People are calling you because they spoke to you at an event a year ago. It just builds.

And then I’m always looking ahead, so that even when things are good and busy, I’m planting new marketing seeds to make sure there are pipelines of business coming in six months or a year. 

Erik Pelton is all about energy, whether he’s representing clients, addressing workshop or conference-goers, volunteering with Falls Church City’s Economic Development Authority, testing his mettle in a triathlon, drumming up support for charity, or wrangling kids on Bike to School Day. His superpower is making complicated subjects clear, using real-world examples to illustrate his points in an engaging—sometimes-hilarious—way. And as an early-adopter gadget freak, the exploding world of technology and associated intellectual property laws is to Erik familiar and fun rather than intimidating. Erik got his start as a trademark examiner for the USPTO and, in the years since, has grown his law practice with the enduring ideals of customer service, affordability, and clarity.

Legal Software Bill of Rights

As a legal software customer, you have a right to demand a few things from the companies with which you do business. Information, for one thing. Like the price, and like security measures.

You have a right to try software before you buy it. And you have a right to get your data out. And you have a right not to get jerked around during onboarding.

Here’s what you should expect from your software vendors.

The price of legal software shall be published.

In order to buy software, first you have to know what it costs. If there is no price posted on the website, it’s a sure sign that the company lacks confidence in its product and relies instead on a hard-sell approach to convince you that it’s worth the price.

The price of software should be posted on the website, and it should be easy to understand. No small firm should have to schedule a demo or speak with a salesperson just to find out how much software costs.

And while we’re on the subject, regressive pricing sucks. Software companies that offer volume discounts probably aren’t going to care much about their smaller customers. Look for software that offers the same rate regardless of the number of users.

There shall be a free trial, which shall be easy to get started.

You cannot know for sure whether software will work for you until you try it. And trying new software should be a pretty simple endeavor. Download and install. Sign up and start using. Or just click to use a dummy account online.

Sure, some companies feel the need to give you a 30-day money-back guarantee or demand your credit card to get your trial started (and they will automatically start billing you if you don’t cancel before your trial expires). These kinds of “trials” are kind of petty, but they’ll do.

However the trial works, you should be able to try software for at least 10 days (although a full billing cycle is ideal) before you buy.

If software requires onboarding, onboarding should not cost extra.

Some software legitimately requires a team of technicians to install and configure. And some software is so complicated (but still, somehow, useful) that it requires training to use it effectively. If that’s true for your software, the onboarding cost should be on the pricing page along with an explanation for why it is necessary.

But there is at least one legal software vendor that requires you to pay for someone to remotely log into your computer to download the install file and double-click it, and then point at all the buttons and menu options and tell you what they do. And there is at least one CRM vendor that requires everyone to pay for training whether or not they already know how to use the software or are comfortable exploring it on their own.

No company should get to charge you for that kind of thing.

Security measures shall be clearly described.

How is client data encrypted, and when? (Before, during, and after transmission? At rest?) Which encryption technologies are employed?

How does the company control access to encryption keys and client data?

Where is client data stored? How often is it backed up, and can customers access those backups to restore data?

Do any third parties have access to client data? If the company is using a third party for hosting (e.g., Amazon), how does it ensure the third party it cannot access client data? Speaking of Amazon, which many cloud software vendors use to host data, if the answer to any of the above is “Amazon takes care of it,” which of Amazon’s many security options has the company elected to employ?

Is the software HIPAA compliant? Does it conform to any other recognized standards (Like the Legal Cloud Computing Association Security Standardshint hint)?

Does the company use a third-party security auditor?

Nobody should have to dig through hidden pages on the website or speak to a sales representative (who probably doesn’t even know) for this information.

It must be possible to export data in a useful format.

The client owns the file, which means you must be able to return the file to the client. You may need to take your clients’ files with you when you change firms. Or you may need to give the file to an ethics investigator someday. Or you may just want or need an archive of the file for other reasons.

One way or another, it should be possible to export data in a useful format. It may be complicated or clunky, but it should be an option.

Dropbox for Lawyers User Guide

Dropbox is popular with lawyers. According to the ABA’s most-recent technology survey, 58% of lawyers use Dropbox, making it the most popular online file storage option among lawyers. Here is everything you need to know about Dropbox, from how to install it to securing your client files.

Installing Dropbox

Installing Dropbox on your computer is simple and easy. Just download the installer to your computer, and run it. If you do not already have a Dropbox account, you can sign up for one during installation. This video from Dropbox walks you through the process:

After you install Dropbox on your computer, you will have a new folder. On a Windows PC, the My Dropbox folder is located in your My Documents folder. (In Windows, you can make your Dropbox folder behave like your My Documents folder. To do this, right-click your My Documents folder, then click on the Location tab and click the Move button. Then, select your My Dropbox folder, and your Dropbox folder will open whenever you select My Documents.) On a Mac, the Dropbox folder is in your home directory. As of this writing, Dropbox also has mobile apps for iOS, Android, BlackBerry, and Kindle Fire.

Any files you put in your Dropbox folder will be automatically synced to the cloud and to any other computers or mobile devices with Dropbox installed.

Features, Add-Ons, and Pricing

Syncing, File Versions, and Packrat

Image: “This image is a vector file representing a cloud data backup sync concept. ” from Shutterstock.

Dropbox syncs your files between your computers and devices and the cloud. That means your Dropbox folder will have the same, up-to-date contents on every device. With Dropbox installed, you can save a Word document on your desktop, then open your laptop and keep working on the same file. Or pull it up on your smartphone.

You can also use Selective Sync to limit the files that sync to a particular computer. For example, you might not want to sync photos of your children to your work computer. Or your client files to the laptop you use at home.

TipIf you are going to do a lot of file sorting, it’s a good idea to pause syncing on all your computers, or turn them off, and use the web interface. This will help prevent duplicate files and conflicts.

By default, Dropbox saves every version of your file, which you can access from the web interface. It is easy to roll back a file to the last time you saved it, or recover deleted files. It functions like an extended “undo” function. However, Dropbox only saves the last 30 days by default. If you want unlimited file versions and undelete, you will need the Packrat add-on.

For an additional $39/year, Packrat will keep unlimited file history. With Packrat, Dropbox functions as a pretty good cloud backup solution for your files.


Other than syncing, Dropbox’s biggest feature is sharing. You can share any file in your Dropbox just by right-clicking a file on your computer or using the chain icon next to any file or folder in the web app. You can share your vacation photos with your friends or your client files with another lawyer in your office, all with a couple of clicks. Rather than attach files to emails, you can just copy the share link and send it, instead.

Importantly, Dropbox also has a sharing dashboard where you can see all the files and folders you are sharing, and who you are sharing them with.

Sharing is pretty simple. The person or people with whom you want to share don’t even need a Dropbox account of their own, if you just use a link. To do this, click the Share link icon on any file or folder in the web app, or right-click any file or folder in your Dropbox on your computer and select Share Dropbox Link to copy the link to the clipboard. In the mobile apps, just use the share button to copy the link to the clipboard.

Dropbox Pro subscribers can also click the Set visibility / expiration link to set a password or set an expiration date for the share link. When sharing a folder with another Dropbox user, you can also set the permissions to view-only and prevent changes.

Camera Upload

Image: “Vector illustration of an old camera with flash and birds on the background of clouds” from Shutterstock.

The Dropbox apps can help you upload your pictures to your personal Dropbox account. The mobile apps give you the option to automatically upload all your photos; on the desktop app, you can upload photos when importing photos from a camera.

You can enable Camera Upload when you first install the Dropbox mobile app, or you can turn it on or off later in the Dropbox settings. It is an easy way to back up and share your photos, but it is also an easy way to get photos or screen captures from your phone to your computer.

Just a note: Camera Upload is only for personal plans, not business plans (see below).

Dropbox has more detailed instructions for using Camera Upload.

Extra Storage

A free Dropbox account comes with 2 GB of storage. You can get more free storage for referring people to Dropbox (up to 16 GB) or using Camera Upload with the mobile app (up to 3 GB).

Still, if you use Dropbox for most of your files, you will probably run out of space. That’s where the paid plans come in. You can get 1TB of storage for $8.25/month, paid yearly. (The plans are a bit more expensive if you want to pay monthly.)

There are cheaper alternatives to Dropbox if that pricing does not work for you. Of course, one of the reasons Dropbox is able to charge a bit more than some of its competitors is that its widespread popularity means that Dropbox works with most of the apps and services with which you might want to use it.

Business Plans

Originally, there was just one kind of Dropbox account. As more people and businesses started using Dropbox, though, some people wound up with multiple Dropbox accounts. Eventually, Dropbox released business plans, and they are finally becoming useful now that you can use your personal and business account at the same time.

While personal accounts are billed according to how much storage you need, business accounts are billed according to the number of users. All accounts come with unlimited storage and some additional features.

The cheapest business plan is $795/year for up to 5 users. Each additional user is $125/year. Solos and very small firms will be just fine using personal accounts, as long as the storage options are sufficient, but the business plan is a great option for firms with 5+ people who need to share files.

Using Dropbox

Some people only use Dropbox to share or transfer files, like a USB drive but more convenient. While Dropbox works great for that, it is hardly the most effective way to use Dropbox.

Because Dropbox lets you share folders, it can function as an effective, inexpensive file server. Best of all, you don’t have to worry about actually maintaining a file server. It just works, and it keeps everyone on the same page. You can even sync up things like your QuickBooks company file or your Time Matters database. (However, the files will only sync when QuickBooks or Time Matters is closed on one computer. If you try to open your QuickBooks company file or Time Matters database on two computers at once, or before everything is synced up, Dropbox will create a conflicted copy.)

On mobile, Dropbox is essentially the missing file manager. Because of its popularity, many apps support Dropbox as a way to get files onto your phone or tablet. TrialPad, for example, largely relies on Dropbox for loading exhibits. So do the best text editors for iOS.



Image: “Big safe door with Gold ingots.” from Shutterstock.

Dropbox is about as secure as your online banking website. That means your data is transmitted to and from Dropbox over an encrypted connection, and it is encrypted while it is stored on Dropbox’s servers. This is pretty standard security for cloud software that handles private information.

“Dropbox is more secure than anything most lawyers have used to secure their files from the Battle of Hastings until about 5 or 10 years ago.”

There are a couple of things to know about Dropbox security, though. First, data is transmitted over an encrypted connection (SSL). The data itself is not encrypted, however, until it reaches Dropbox’s servers. There, it is encrypted before it is stored on Dropbox’s servers. Second, Dropbox has your encryption key. That means Dropbox can decrypt your files if it has a good reason to (like a subpoena). There are reasons why Dropbox does these things, but there are alternatives with greater security — and some tradeoffs. If you want greater security but you still want to use Dropbox, Viivo may be the best way to have your cake (Dropbox) and eat it too (file encryption).

Dropbox also offers two-factor authentication, which makes it much harder for someone to log into your account, even if they find out your password. To log into Dropbox with two-factor authentication, you have to enter your password as well as a code sent to your smartphone (or generated by an authentication app like Google Authenticator in order to log into your Dropbox account.

If you are storing anything important in Dropbox, you should definitely turn on two-factor authentication for substantially better login security. Make sure you get your recovery code after you turn on two-factor authentication, and store it in a safe place in case you ever need it.

Dropbox Pro and Dropbox Business subscribers can also remotely wipe the files from a device when unlinking it (you can see which devices are linked to your Dropbox account by going to Settings > Security).

Terms of Service

Dropbox recently amended its terms of service to include mandatory binding arbitration and ban class actions. If you do not like these user-unfriendly changes, consider another service. As of this writing, the terms of service for Box and Google Drive did not contain mandatory binding arbitration or a ban on class actions.

With Dropbox, the terms for a personal account are the same whether you pay for the service or not. Some companies, like Google, change the terms of service when you become a “premium” customer.

Who Should Use Dropbox

Dropbox is perfectly safe for most lawyers to use for client files. As Lawyerist contributor Eric Cooperstein wrote:

Dropbox is more secure than anything most lawyers have used to secure their files from the Battle of Hastings until about 5 or 10 years ago. Only the rare lawyer … needs to worry about a higher level of security. … Dropbox is just fine for most solo and small firm lawyers’ client files.

Texas criminal defense lawyer Mark Bennett strongly disagrees, and he makes some good arguments against using Dropbox for client files. Those arguments are even stronger now that we know what the NSA has been up to, and after the Heartbleed showed how a minor error by an OpenSSL developer can lead to a huge security breach. Cooperstein is still right, but many lawyers will want to re-think the cloud and use it in a more limited way from now on.

But that doesn’t mean you should not use Dropbox at all. Indeed, you can hardly avoid it if you want to be productive on more than one computing device. Instead, go ahead and use Dropbox, and use an add-on like Viivo to encrypt sensitive information.