Smaller Law 101: My 2023 Holiday Gift Guide for Disgruntled Lawyers

It’s holiday party season for lawyers, and, man-o-man, have I spent a bit too much time around tipsy lawyers over the past few weeks (disclaimer: I’ve been to 2 parties).

It’s also the time of year for: all-nighter transaction work; squeezing files for extra billable hours; year end bonuses; meetings with compensation committees; and polishing up resumes for when all of the above go wrong.

Long story short, these are stressful, uncertain times, and I seem to be answering a lot of the same questions about leaving Big Law and starting a law firm.

So, for those of you who have stressed-out lawyers in your lives, I offer these suggestions as my 2023 Gift Guide for Disgruntled Lawyers.

Want to start your own firm, but have no idea where to start? Buy your lawyer a year subscription to Clio, a comprehensive online practice management platform that offers everything needed to run a law firm: time tracking; billing; online payments; document management; contacts; case and matter management; and everything else. Clio integrates with hundreds of third-party apps, and it’s designed to be the central hub through which all operations run. It’s awesome and costs about $1,000 per year. And, of course, it’s fully online (and secure), so there’s no need for that $25,000 on-site server that makes those strange buzzing noises behind the locked door at the old law firm.

What about everything else? That’s where an annual subscription to Microsoft365 comes in. For about $150, you get e-mail (Outlook), Word, Excel, Powerpoint, Teams, OneDrive, Sharepoint, and about 25 other programs that you’ve never heard of, but are awesome and useful (Bookings has changed my life). Plus, unless you’ve been living under a rock, you probably know that Microsoft is an industry leader on AI research, and you’ll get to be on the frontlines of Microsoft Copilot. That weird picture at the top of this post? It was AI generated by Microsoft Designer.

I haven’t seen anything about phones yet. Here, you’ve got two good options. The industry standard for video communications, Zoom, is now offering VoIP phone services (with pricing starting at $120 annually). Since you will have to get Zoom (all of the remote court appearances and conferences are on Zoom), this is worth looking into. (I use Ringcentral for phone, fax, and business texting, and it’s a bit wonky, but it works).

What about copies, printing and scanning? Most lawyers probably use some high-capacity printer, which is rented from a third party service (and the firm pays a monthly fee and a per page quota each month). You don’t need that. Find a good, mid-quality print/copy/scan machine from HP, which will cost you about $500.

What about the fancy offices? Don’t sign a 5 or 10 year lease for commercial office space. Instead, call one of the 5-7 fancy coworking spaces that have opened in Nashville. I use WeWork, which has been awesome (and has accommodated me in Austin, Chicago, and Seoul). Other options on Music Row include Ampersand Studios, Industrious, Kennect, and e-spaces. These spaces are all “turn key,” meaning they offer printing, internet, limited staffing, and package handling for a low monthly membership fee, generally ranging from $200 to $350.

What about websites and marketing? Some lawyers do this themselves. I don’t recommend that because branding is too important. For all of my various iterations of my own law firm, I’ve used Huckleberry Branding. They’ve designed my logos, helped with color schemes, designed a custom website, helped with content, and also all the incidentals that come with it all (including letterhead, envelopes, and business cards). While I’m embarrassed to have done this 3 times, I’d hire them again if there were a 4th time. They are awesome, and getting started with good branding is too important to do on your own.

What about staffing? You may wonder about who will do all the “little things” to keep the new firm running. (At my old firm, there was a person dedicated to making sure there were cold Cokes at all the meetings.) At a small firm, the lawyer will do all these little things, as well as the medium and big things. To make it a little easier, I’d recommend hiring a phone answering service. I use Abby Connect, a 24/7 answering service whose goal is serve as an extension of my own firm. I’ve used others (Posh) in the past, and the main differentiating factor tends to be pricing and frequency of use. These services cost range from $200 to $500 per month.

What about everything else? Stamps.com for everyday mail. Simple Certified Mail for certified mail. Simplifile to record documents (state-wide) with Register of Deeds’ offices. Lawpay to accept credit card payments (and, yes, Clio offers Clio Payments). If you’ve got lots of documents and need to super-charge document management, the biggest player in the market is NetDocuments (which I use) and is about $75.00 per user per month. I use Minnesota Lawyers Mutual Insurance as my malpractice carrier, and I can’t tell you if they are any good because I hope to never call them ever (about $150.00 a month for robust coverage).

What if this is still too complicated? Buy them a one-hour “Ask an Expert” call with Adriana Linares, of Law Tech Partners, a lawyer-turned-legal-technology consultant who takes a no-nonsense approach to coaching up entrepreneurs on making the early-firm decisions, as well as the late-firm decisions (I had a call with Adriana a few weeks ago).

It’s wild to think that you can run a fully functioning law firm for under $1,000 a month, but it’s entirely possible. It’s also lots of fun to explore all the innovations in legal technology. It’s an unprecedented time for growth in legal tech, and a lawyer with an entrepreneurial spirit has more options now than ever before in how she can practice law.

If there’s a lawyer in your life who believes her law firm isn’t giving her the freedom to nurture that entrepreneurial spirit, I hope this Gift Guide is the first step to a fruitful and lucrative 2024.

If any of you are thinking about making this jump, reach out with any questions, fears, or complaints. I’m happy to help. If I’ve left anything out or if you have any other questions, let me know, and I’ll respond.

Mic Drop: Happy Birthday to Me and My Law Firm

Today (August 8) is my birthday, and it’s also the three-year anniversary of when I started my own firm (well, August 7). With this post, I’ll ask you to indulge me a bit.

It’s a happy birthday toast to my law firm.

It hasn’t been a straight line, but it’s always been onward and upward. I cringe a little bit re-reading my August 2020 post announcing the move. My mission statement still rings true, but, in retrospect, I hadn’t quite run my “big plans” past the other firm (or the other other firm). I was just so excited to be building something new:

I tend to wake up, involuntarily, at 4:45 a.m. or so, to worry about whether it was the right choice and about all the work to be done to build something. Opening bank accounts. Picking office space. Hiring staff. Hiring lawyers. And, of course, doing the legal work for all the clients. And by “wake up, involuntarily,” I really mean “freak out” about what’s next.

My mistake was that I had no idea what I was looking for, until I happened to find it. It’s crazy that, 3 years ago, I typed out the above words, but it never once crossed my mind to actually start my own firm. Instead, I had spent the prior 3 years looking for, simply, a different Big Law Firm. /s/ Because everybody knows that the best way to have a voice in the big firm decisions and autonomy in your law practice is to move to a Big Law Firm. /end sarcastic voice/

Fail fast. So, I had all these big plans for an innovative way to run a law firm, and then somehow decided that I should definitely open an office for a 100 year old law firm based in a city 300 miles away. Reading that last sentence, I totally see the red flag. In reality, it took about 2 weeks. One more (brief) false start later, I decided to go Solo.

Trial and Error is sometimes the best teacher. I won’t recount the mistakes I made in the first 15 months running my own firm, but I’ll tell you that, by November 2021, I was annoyed, fed up, and ready to find the biggest law firm that needed a creditor rights expert. To that end, I met with a legal recruiter, Tara Boosey (who had an office in my building), and told her that I was sick of it, described what my dream job looked like, and told her to find it for me. Her advice? “It sounds like you already have the perfect job for you.” Not what I wanted to hear at that moment, but such great advice.

Just focus on the firm I have. Then it clicked. The work and referrals had always been there, but the unlikely encouragement really focused me on my path. A past obstacle was that clients tend to call me whenever something comes up, and I fretted about the client who maybe calls once a year for an IP referral or the other who sends me 1-2 complex commercial transactions that are way over my head. How could I help them, if I wasn’t at a huge law firm? Simple: I wouldn’t. I’d focus on exactly what I do (and do best), I’d build a network of small-law experts who I trusted, and the smart clients would appreciate a thoughtful referral to another awesome attorney.

And, then, focus even more. Even though the phone never stops ringing, I bill less hours than I used to at the big law firm. That’s because I also spend so much more doing everything else: marketing, IT, accounting, you name it. There are only so many hours in the day. If I couldn’t accept every new case, then I’d have to decide which of the clients I could help. I began to ask things like: Which clients are jerks? Which ones take forever to pay? Which ones are unreasonable? Which ones don’t listen to me? Those were the first ones to go. I call it the Client Decision Tree.

The good clients sustained the firm. Three years ago, when I announced that I was leaving my old firm, one client lost his mind, thinking he didn’t have the option to go with me. In a frantic email, he wrote “Wherever you are, that’s where I want my cases.” Needless to say, that client made the cut and has followed me through every step, through 4 different email addresses (ugh). Since August 7, 2020, I’ve opened 517 new client matters1. Maybe I’m not as low volume as I thought; that number is surprisingly high. A large part of that (maybe 200) were old matters that followed me when my bank clients said “take everything.” (It turns out that my fears that I wouldn’t have any clients unless I stayed in a Big Law Firm were incorrect.)

Working less is a good thing. Once upon a time, no matter what the old firm’s billable minimum was, I exceeded it. Obsessively. It was unhealthy, and maybe bad lawyering. The law should be thoughtful, strategic work, and “high volume” anything does not create the best product. I had a crushing workload. Billable hour mandates are driven by expenses and overhead, and, if those could be kept in check, I believed that my new model could produce high quality work, balanced with a healthy lifestyle. So far, so good: Last year, my hours hit an all-time low, but my net income hit an all-career high.

The mission statement wasn’t entirely crazy, either. Since opening my own firm, I’ve been recognized as an Attorney for Justice by the Tennessee Supreme Court every year. I have helped a Nashville group distribute more than a million dollars in property tax protection and racial justice reparation funds. I’ve started a charitable program, Lawyers Give Back, that has supported 17 different area charities. And, yes, the firm works really hard in service of our clients. I still lose sleep worrying about my cases–there are just intentionally less of those cases to worry about.

In the end, I discovered that I had my dream job. At the old firm, I took my kids to school maybe 10 times over the course of 5 years. In the last 3 years, I bet I’ve done 300 drop-offs and pick-ups. I’m a better lawyer, and I’m also a more engaged husband and father. (After a “law firm divorce,” I can assure you that your law partners don’t actually love you like family.)

Byeonhosa Noraebang! I never took real vacations; instead, I’d tack a few extra days onto 3 day weekends here and there. This year, my family took a dream vacation, spending 3 weeks in South Korea. Our trip culminated with a great dinner with two Korean banking lawyers (and friends), who took our family to noraebang afterwards (on the 10th anniversary of BTS’s debut).

If you’ve made it this far, you may be wondering what my point is, other than a bit of bragging. That’s fair, but we should be able to authentically celebrate all sorts of successes and not just brag on LinkedIn about being a Super Lawyer.

There’s a stigma attached to being a solo lawyer, which isn’t fair. A lawyer doesn’t have to work at a big law firm to be successful or to produce sophisticated work. Three years ago, I couldn’t comprehend that, a result of years of false messaging from law schools and bar associations. Even 20 years into my own legal career, I fell for that BS, and my ignorance wasted a lot of my time.

Don’t get me wrong. Running a small firm is hard and can be a complete pain in the neck (feel free to read some of my other blog posts on that topic). I often tell people “It’s the best job on earth, and it’s the worst job on earth, but it’s never in the middle. I used to spend a lot of time in the middle.”

I also used to tell my kids that they were forbidden from ever becoming lawyers, because it was such an awful job. Not anymore. Now, for the first time, I can picture a day when one of my kids might take over the little firm.

What a three years it’s been. I’ll conclude this post with a celebratory link to BTS’s Mic Drop (a song in which South Korea’s greatest boy band encourages you to relish your successes and also to tell your haters to annyeonghi gaseyo).

Now, I’ll turn off the work email early and go enjoy a birthday dinner with my family.

  1. A prior version of this post said 549, which is what my billing software shows and sounded bizarrely high. On further research, that included a few adminstrative / pro bono / conflict type file assignments, so I reduced the number. ↩︎

Smaller Law: You Don’t Answer Your Own Phones, Do You?

Last year, I was making small talk with a Medium Firm lawyer at a fancy lawyer dinner, and I was complaining about all the phone calls.

The conversation hit an abrupt stop….

Him: Wait a second. You don’t answer your own phone calls, do you?

Me, after an awkward 5 second pause: HA! No way, of course not, are you kidding? (said, literally, while my phone was vibrating in my pocket with a new call)


One of my favorite parts of having my own firm also relates to the least fun part of it: I make every administrative decision and also pay for every decision.

When the cost of every subscription, new technology, and sponsorship comes directly out of your own pocket, you develop a critical eye when making decisions.

With every one, I always ask: Will this help me serve my clients and/or make their experience working with me better? If yes, I then ask: Is it absolutely necessary?


At my old firm, every fall, a brand new stack of the Thomson Reuters “Rules of Court” books would show up on my desk. It was great. I’m a litigator, and, back then, I’d have stretches where I went to court every day of the week. Those books are useful.

But, not absolutely necessary. Everything in those books is available on Westlaw (if you’re a subscriber). They are also totally free on the Tennessee Courts’ website or the United States Courts’ website. They were a useful luxury.

Even back then, I’d get so worked up when I’d see that cart full of the new versions being delivered to every lawyer at the firm. About half of the lawyers never went to court and most likely never touched the books. At 40 lawyers, the $600 price tag turned into real money fast.

Because the $25,000 invoice didn’t come out of any one person’s pocket, nobody ever questioned the expense. We were a big firm, and buying a set for every lawyer was just something you did.

Over time, I saw dozens of budget items that had accumulated over time, which simply became legacy institutional costs that nobody questioned.


Just like paying somebody to answer your phone.

A disclaimer: I’ve always been a “direct line” lawyer, but my clients generally learn to email me for best results. (I mean, post-COVID, who is making “surprise” calls and expecting the other person to have a substantive conversation with you on the spot?)

And, yes, my old firm had people who intercepted unanswered calls and then flipped them to my voicemail. Nowadays, I use a third-party answering service, Abby Connect, to do the same thing, but for about $300 per month. As long as the client hears back promptly, they haven’t cared at all.


There’s really no right or wrong way to run a law practice. What works for one firm might not work for somebody else.

Having said that, though, there’s a direct correlation between how expensive it is to run a law firm and how many hours lawyers are forced to bill. Everything you read about lawyer burnout and stress suggests that an oppressively heavy workload isn’t ideal.

Sure, frisbees with your law firm logo on them are fun, but, somewhere, there’s an associate attorney billing an hour to pay for that.

When I make a decision for my own firm, I also know that any added cost means added billable hours. Some costs are necessary; others simply aren’t worth the extra burden on my schedule.

Today, I’m lucky that I’m the one who gets to make that choice.

My advice for other lawyers thinking about switching firms? Consider whether your values align with the people who will be making those types of decisions. It’ll be you paying for them.

Also, law firm clients, this same warning applies to you. I mean, you’re the ones who pay for all of it.

Smaller Law 101: Advice on Growing your next Law Firm

Exactly three years ago, I was struggling with two decisions. One, whether to buy a boat. Two, whether to leave my long-time law firm.

As to the boat, the world is full of advice about that. Ask anybody you know, and you’ll instantly hear the joke about the “two best days of a boat-owner’s life.” There’s so much information online (generally negative) that a prospective boat buyer has to actively ignore it all.

As to the second (far more important) decision, I was surprised by how little information was out there. Bar associations tend to avoid the topic like the plague. Their business model is to keep big law firms happy, or, at the very least, to not encourage mutinies. Other lawyers aren’t much help either–you’ll rarely get an honest response. They’ll either embellish (for good or bad) or, worse, let slip to somebody that you’re thinking of leaving.

As a result, most lawyers keep quiet and rely on legal recruiters or their own ego, two very unreliable and heavily biased voices.

In this wild Nashville legal market where lawyers are constantly switching firms (and, in a surprise twist, switching back to the original firm), there’s value in real talk. Sometimes the billable hours aren’t greener at the other firm.

For me, I got the law firm decision right. Having said that, even though I’ve had three very successful years, it’s all been built on a foundation of small mistakes, miscalculations, and lessons learned the hard way.

I could write a book about all the things I’ve learned about entrepreneurship, law firm management, marketing, and psychology but, instead, I’ll write some blog posts here over the next few months as the 3 year firm-iversary approaches.

As for the boat? I totally screwed up that one, a mistake so notable that it was documented on the front page of USA Today.

If you’re considering leaving your existing firm, I hope that these blog posts over the coming weeks will be useful –or maybe just keep you out of the national news.

On Lawyer Stress (a/k/a the Post I will send clients when I raise my rates for 2023)

Do you think you might be having a heart attack?

No matter what the actual ailment is. Food poisoning. Anxiety. Indigestion. Insomnia.

When you wake up at 2am, with a racing heart, and a feeling that something isn’t quite right, and get asked “Do you think you might be having a heart attack?

Well, in that moment, you think one thing. That you might be having a heart attack.

I know this from my own experience, just last month. It was the very early Tuesday morning evening of a very busy week: I had a trial scheduled to start 32 hours later in Memphis and, at the end of the week, a bankruptcy conference in California.

And, in that moment, at 2am, yes, it felt like I was having a heart attack.

Continue reading “On Lawyer Stress (a/k/a the Post I will send clients when I raise my rates for 2023)”

My 2022 Worst of Legal List: A Highly Biased List of Niche Things I Disliked

I promised a follow-up to my “Best of List,” but, since complaining is more fun, I am writing about some things I disliked in 2022.

The courts system’s quick return to pre-COVID practices. You remember my rant when I caught COVID on a 5 hour docket in July. I think courts were too quick to abandon the pandemic innovations and return “to the way law was practiced when people rode horses to court.” Sure, a court might let you call-in for a hearing, but there is always a risk the technology won’t be up to speed, the judge won’t realize you’re on the line, or she won’t be able to hear you on the invariably staticky line. Having seen the trouble other lawyers had with call-in appearances, I decided to never risk my client’s case on a remote appearance. When in doubt and given the option, lawyers will generally appear in person. How about–for some hearings–there’s a process that allows for no other option other than to call-in?

There’s no state-wide, uniform e-filing system. My law practice has a fairly small foot-print. (My marketing materials call it a “curated practice.”) In the 3-4 counties where I do most of my work, I have separate log-ins for the different courts in each of those counties. Each e-filing system has its own set of rules, exclusions, and peculiarities. E-filing is awesome, so I’ll take a bad system over no system. But, having said that, why can’t the State of Tennessee establish a uniform system?

Our Tennessee foreclosure system is entirely based on physical newspapers. Until recently, I had a newspaper subscription, even though: (a) for the past 20 years, I’ve gotten 99% of my news online; (b) my local newspaper had shrunk to about 10 pages (total); and (c) my newspaper carrier generally delivered my morning paper either 8 hours late, the next day, or not at all. Physical newspapers are possibly the worst way to convey information in our modern age, but, nevertheless, Tennessee’s entire foreclosure and UCC sale system is tied directly to published notices in physical copies of newspapers. All over the country, newspapers are going to an online-only model (followed, most likely, by going out of business). But our foreclosure laws haven’t been updated. We’re headed for trouble unless we change these laws.

There’s no penalty for bogus lien filings in Tennessee. Sure, there’s the toothless “exaggeration of lien” statute (Tenn. Code Ann. § 66-11-139) or the confusing “slander of title” cause of action, but, by and large, if somebody records a piece of paper with “Notice of Lien” written somewhere on it (and includes the owner name and property address), they’ve got a totally un-lawful, but also practically-effective, lien. A few years ago, the Tennessee Legislature passed Tenn. Code Ann. § 66-21-108, which gave property owners a nuclear bomb to deal with invalid lien claims, but it was repealed within a year. As it stands now, there’s no useful remedy, other than to pay the invalid lien or to cancel your transaction.

Big Mortgage Lenders refuse to provide payoffs on their debts with impunity. One of the weirdest sub-plots throughout my 2022 was how near-impossible it was to get a payoff from mortgage lenders. In December, I had to sue a mortgage lender to get a payoff (and to stop an immediately pending foreclosure sale). It might have been the dumbest lawsuit I’ve ever filed (dumb as in the other side was dumb to make me go to the trouble): Within 24 hours of my getting a foreclosure injunction, the lender provided the payoff and, within a few hours of that, it was paid off in full. A win, except it cost more than $5,000 in unrecouped legal fees to address an unnecessary situation. There needs to be a law that imposes penalties, including attorney fees, in these situations.

I spent the entire year in a sales funnel. In 2022, after a full year as a small business owner, I took some time to evaluate my existing legal technology and services and what needed to be upgraded. On legal tech websites, I’d enter my email in order to download some awesome “Free Guide To _____” that promised a magical solution or explanation for some common problem or process. Having downloaded a number of those (none of which solved any problem), my phone rang all year long, over and over, with sales calls. It’s not “free,” if I end up in a Sales Funnel. My advice to service providers: How about sharing your expertise, impressing me with your vast knowledge, and leaving me alone, confident that I’ll return to you for my buying needs?

Phone calls from Tom James Company custom clothiers were the worst. If I ever find out who sold my name and phone number to Tom James Company, I will immediately sever ties with that organization (I suspect one of the bar associations did it). Tom James representatives were relentless in 2022. They called me so many times that I remembered the caller’s name (from the prior week’s call), could recite their opening line back to them, and remind them that I was the person who wasn’t interested because I buy all my suits from South Korea, just like BTS (not true, but why not go big, right?). After maybe 25 calls in 2022, I reached out to Tom James corporate, and asked if I could pay them something to be added to a no-call list.

Dealing with global, multi-state law firms. All of Nashville’s medium to big law firms are slowly selling out to mega-law firms. For the most part, I still deal with local folks on my litigation matters, but, on matters where a Tennessee law license may not be required, I have to deal with out-of-towners, and it’s rarely a pleasant, easy relationship. It’s a trend I’m dreading, as these firms bring their billable rates, minimum hourly requirements, other customs into the work they do in the local market. In short, their weirdness makes my job harder.

I miss old twitter. Many years ago, while waiting at a docket call in Montgomery County, I tweeted that I forgot to bring a pen for court. Within a minute, a local lawyer who follows me on twitter introduced himself and handed me a pen. Over the past decade plus of very-regular twitter use, I have found a vibrant and diverse lawyer community who post updates, victories, and advice. It’s awesome. Over the last few months, it’s gotten less active. If twitter as we once knew it goes away, we will have truly lost something.

The Lawyer-Industrial-Complex has gotten out of hand. Have you tried to hire a lawyer lately? If so, you were probably shocked by their hourly rates. The Clio 2022 Legal Trend Report (warning, you have to enter your email to access it) says that, in fact, lawyer rates are too low and haven’t risen with the general rate of inflation. I don’t know about that, but, holy smokes, lawyers and all the law adjacent services are so expensive right now. I’m using a Westlaw Rules of Civil Procedure book from 2020 because a new set (that will be obsolete in a month) is nearly $1,000. Some lawyers say that this isn’t a problem (more money in my own pocket, right?), but, frankly, it’s a trend that I don’t like. Prices are going up, but the quality of service is staying the same.

Having said that, where are all the good, reasonably priced Nashville lawyers? As noted above, I keep a small footprint for my law practice, and I refer out about 2/3 of the “new client” calls I get. My biggest problem with referrals has been “To whom”? I only refer cases to lawyers who will make me look good and will do an awesome job. Everybody on my existing list is swamped right now. What Nashville lawyer does good, competent, cost-efficient work? And, also, is looking for more work? I can’t find him or her. But I’m looking.

My 2022 Best of Legal Lists (Part 1): A Highly Biased List of Niche Things I Liked This Year

Everybody’s doing “end of the year” lists, so this is my list of law-related things that I’ve enjoyed in 2022, in no particular order:

Best Show About Lawyers? Extraordinary Attorney Woo: This South Korean legal dramedy follows Woo Young-woo, a new law school grad starting her career at a white shoe law firm. It debuted in summer 2022 to record-breaking ratings, and is currently streaming on Netflix.

The show offers commentary on the legal profession through a novel lens: Attorney Woo has autism spectrum disorder, so many of the profession’s customs and courtesies are lost on her. Through her unique perspective, the show thoughtfully examines universal issues facing lawyers everywhere, like burnout, imposter syndrome, and nuanced ethical issues (i.e. should an attorney care if their clients are corporate “bad actors”).

Maybe it’s the South Korean cultural influence, but the show presents a thoughtful and refreshing alternative to the typical blinged-out, L.A. Law-style lawyer portrayal. Added bonus? After watching the show, my kids think lawyers are really cool…

Best Lawyer Jokes on the Internet? Alex Su. Lawyer jokes are pretty bad, mainly because they play on misconceptions and miss their mark. Alex Su, a reformed corporate lawyer turned legal tech sales guru, knows exactly where to aim his mockery.

You can find his work on his TikTok page and Instagram, as well as his long-form blog, Off the Record.

@legaltechbro

Reposting the Tik Tok that first put me on the map #lawyer #paralegal #lawschool

♬ Blinding Lights MuchDank edit – Marvie

He may be the funniest lawyer on the internet, but, whatever you do and no matter how brilliant and hilarious you think one of his clips is, never try to explain your favorite videos to a non-lawyer. They will not laugh. Alex has invented the niche category of “lawyer-jokes-for-lawyers-by-lawyers.”

Best third-party service that has made my job easier? Proof Technology, Inc. The most frustrating part of a new lawsuit is often service of process. Especially when you’re dealing with an out-of-state defendant, and you have to hire an out-of-state process server and have no idea who to hire. In my experience, whoever you hire will not care about speed, customer-service, or communication with a “one-off” customer. Unfortunately, your own client will care desperately about all of that.

That’s where Proof comes in. Proof is a nationwide service of process company, who–after you upload your legal documents to their site–does all the work to hire, monitor, and make sure you get your documents served, using their network of servers. Due to their nationwide network, you get the benefit of their buying power.

In the past, I’ve just used a random google search and hoped for the best, but generally expected (and gotten) the worst. Since I’ve started using Proof, I’ve been shocked at how easy this process is. I can’t recommend them enough.

Best Legal Conference? Clio Cloud Conference. Earlier this year, I raved about ClioCon so fanatically that a stranger on twitter attacked me for it. Doesn’t matter to me. I’m signed up for ClioCon 2023 (in Nashville), and I can’t wait.

Best One-Stop-Shop for a lawyer logo, website, and everything else? Huckleberry Branding. I left my big law firm 2.5 years ago, and, since then, I’ve had three websites and three logos (well, the “third” incarnation is going to be unveiled in a few weeks). Of course, there’s an entirely different post about that, but I want to talk about Huckleberry for a moment. They are genius branders, artists, and designers, and they really learn your story and incorporate your vision into building a unique and representative brand concept.

Is it time to upgrade from a bunch of people’s last names yet?

If so and/or if one your New Years resolutions to update your brand, call Mariko.

Other best items? I’ll probably supplement this list a few more times over the next few days, so stay tuned. It’s sort of hard to remember an entire year all at once. Tune in for Part 2 later.

“Clio is a Vibe” – The 2022 ClioCon From the Eyes of a Regular Lawyer

I had a blast at the 2022 Clio Cloud Conference in Nashville.

A legal conference where, at the end, you were sad that it didn’t last longer. Have you ever heard that?

You’ve probably never been to ClioCon then.


The simplicity of that arrow is misleading.
This event was at Opryland Hotel. Everybody was lost, all the time.

Clio is a cloud-based legal practice management platform. With more than a decade of constant feature updates and welcoming third-party app integrations, Clio is designed to be a “one-stop-solution” for running a law firm. Billing. Document management and automation. Intake and client relationship management. Calendaring.

Basically, for everything a lawyer does during the day, Clio’s goal is to make it easier and more efficient. If they don’t offer a solution, let them know, and they’ll create one. One legal tech commentator called their culture “a cult of innovation.”


You probably think this is a paid post. (I mean, who shows this sort of rabid exuberance for legal practice management solutions?)

There are lots of law practice management tools out there, but none have the branding or message that these guys do (or care to have it). Clio casts itself and its users as rebels and disruptors. Clio knows its core audience, and ClioCon is a concert where they play the hits.

I’m telling you, Clio is a vibe.

In his closing address, Clio CEO Jack Newton said attendees were part of a “tribe.” “We are part of a big community here with a common goal of transforming the legal experience for all,” he said.

Legal tech writer Bob Ambrogi wrote this about the 2022 event: “It is no exaggeration to say that this is a conference in which it feels as if every single person is there because they are deeply committed to improving the practice of law and the delivery of legal services through the better use of technology and the innovation of their practices.”

Clio and their some 200 employees were there, at every turn, offering impromptu training sessions, directions (ugh, Opryland Hotel), and friendly smiles.

It was like hanging out with 200 people who really wanted you to be better at your law job, but also were your new best friends, and, occasionally, a life coach.

Part instructional, part sales-pitch, part motivational/self-help pep talk, it was hard not to leave ClioCon fired up about being a better lawyer.

(I actually signed up with FOUR new technology service vendors after leaving.)


The theme this year was, essentially, the world political and economic landscape is a mess, only getting worse, and we (and our clients) are in for some tough times in 2023. What can we, as lawyers, do to prepare and to provide better service to our clients?

It’s different than a typical legal conference because of the diversity of attendees. People come from all over. Most are lawyers, but some are administrative staff and other legal professionals. Many attendees are neither, but work on innovations in legal technology and processes.


Nevertheless, across the board, the common theme was that we (the Clio staff, the attendees, all of us in the room) are collectively collaborating on something different, rebellious, innovative…and all with the goal to provide awesome service to clients.

Every conversation I had–walking all over that awful hotel; waiting for sessions to start; meals–the topic was “how does your firm [insert some technical/practical law practice task].” “What works/What doesn’t.” People were there for one reason: To be better lawyers.

Who can’t help but get fired up about that?


I’ve attended 3 ClioCons now (the first two were remote, due to the pandemic).

My first year, it felt like we all were in on a big secret. In the early COVID world, it felt scandalous to openly talk about things like virtual law firms, document and client communication automation, and fully cloud-based systems. This was a crowd that held zero regard for “The Way Things Have Always Been Done.”

It felt awesome and liberating to not have a Managing Partner hiding around the corner, waiting to tell you that “we’ll form a committee to consider your idea and tell you ‘No’ in 6 months.”


In the past few years, the rest of the industry has come a long way, but they’re still far behind the types of things that are being discussed as a matter-of-fact at ClioCon.

What I’m saying is this: Find your tribe. If you care about things like disrupting the status quo in the legal industry and ways to be a better (and happier) lawyer, come to 2023 ClioCon in Nashville (yes, again) on October 9-10.

You can register here. I’ve already signed up for it.

My only compliant: No karaoke. Clio, if you’re reading this, call me. I can fix this.

Small Law Firm Life: The Best, The Worst, and All at the Same Time

Three Sundays ago, I got locked out of my laptop.

Neither Dell, Microsoft Support, or frantic prayers could save the day. My working laptop was somehow connected to an expired domain (my expired firm), and it was locked shut. (“A very expensive door-stop,” the nice lady at Dell Support in Texas unambiguously explained.)

After spending 5-6 desperate hours on the phone on a gorgeous early-fall day, I had cobbled together the diagnosis: This is exactly what the system is supposed to do in a situation like this; and The remedy was to wipe the computer and start fresh.

This was bad news.


If you’ve ever sat next to me at an event or at a cocktail hour, you know I like to talk in colloquialisms. For me, it’s a way to survive small talk, but also a way to be authentic and also contextually appropriate (i.e. to make a joke).

Maybe the best response from me would be a simple “I’m fine, how are you?” But, sometimes, why not be honest and funny (especially if you are one of the rare Nashville attorneys who has won a city-wide award for their sense of humor)?

If done well, the response is short, funny, but also brutally (and subtly) honest.


While doing the rounds on the 2021 lawyer holiday party circuit, lots of people asked if I liked my small law practice. My response was generally the same: “It’s the best job on earth, and it’s also the worst job on earth. But never in the middle. Sometimes, I miss the middle.”

It was quick, easy, and honest. For more than a decade, at somebody else’s firm, I spent a lot of years in the middle. I billed my hours and won my cases, but I didn’t have any say in the big (or the day-to-day) firm issues. It was frustrating and unfulfilling, but also comfortable and familiar and easy.

Plus, on any day when my computer didn’t work, I had somebody to call who spent their Sunday figuring it out.

In fact, that’s something I told the Tennessee Bar Association’s Sidebar Podcast last year: “My job used to be to show up, do awesome legal work, and write down my time. Now, my job is to do all that, and also take out the garbage.”


Back to the laptop. In the end, let’s be clear: It all got sorted out.

My legal tech “committee of one” had made the right choices about Clio (a cloud based practice management system), NetDocuments (cloud based documents), and a redundant Microsoft OneDrive backup. Plus, I have a backup computer (“Dynamite”) that is fully functional and has been promoted to first chair.

Other than the hassle, wasted time, and the year of my life that the stress cost me, all ended fine.


Last year, after using my “best job, worst job” line at a holiday party, I got a text the next day, from a managing partner at a local Big Law Firm who I had talked to. Maybe I wanted to interview with them and cut out all the hassle of running my own thing, he asked.

All he had heard was the “worst” part, I guess. It was awkward and awful responding (and I made sure to avoid him at the next holiday party), but I had to be honest: “Hey, thanks and I may take you up on that someday, but I’ve had a long stretch where it’s been the ‘best job’ and I’m going to ride this for a while.”

There’s not really a point here, other than to say that you should be sure to back up your documents in multiple places. And, also, that life is too short to live in the middle. And, finally, not to be too braggy, but small law firm life really is the best.

COVID in 2022 and how we’re missing a chance to make the courts safer

After 2.5 years of not catching COVID, I began to think I was special. That, maybe, I had a rare, super-human immunity. That, at some point, future scientists would ask to study my blood to cure unknown diseases.

But, last Sunday, I woke up feeling terrible. My Sunday morning COVID test was negative, so I assumed I’d caught a summer cold.

After 2.5 years of wearing masks, avoiding crowds, and, generally, being really safe, I had hardly gotten sick and, maybe, this is what a cold feels like.

Reality hit two days later, when–still sick–I took another COVID test. And then another. I was 2 for 2 positive.

And I knew that I caught COVID in court.


My last big, pre-COVID night out on the town was a Friday night, February 28, 2020, the week before COVID hit. We went to Cross-Eyed Critters, the best karaoke spot in Nashville. It was the unofficial after-party for our kids’ Parent-Teacher fundraiser, and it was a night for the ages. In retrospect, it was also a post-COVID nightmare, with close talking, jam-packed seating, and no ventilation.

It was also the last time we’ve been in that type of crowd in the past 2.5 years. Early COVID was no joke, and we took it seriously. No more football games, concerts, restaurants, or crowded karaoke for us.

If we didn’t have to leave our house, we didn’t. And, to this day, we still don’t.


The biggest COVID risk for our family has always been me. I’m a lawyer (as you know), and my schedule isn’t always up to me. Part of a lawyer’s job is doing whatever is needed to represent their client, and I take that responsibility very seriously.

Early on, when courts were shut down and virtual, I was fine. In fact, I posted on here all the time about how my job got easier. Lawyers weren’t setting unnecessary matters for hearing, and courts were incorporating new technologies like Zoom trials(!) and e-filing systems to reduce in-person work.

But, despite all the law articles about the Future of the Law, by July 2021, the future was trending back to “the way things have always been done.”

As Nashville lawyer Daniel Horwitz tweeted, “If you thought that we were at risk of staying in a quasi-21st century state of affairs—rather than instantly reverting back to the way law was practiced when people rode horses to court—I assure you, yours fears were never founded.”


And that’s, pretty much, where we find ourselves in July 2022.

It’s a shame, really, because so much of the technology, innovation, and streamlining that we did in response to COVID shouldn’t have been a stop-gap, it should have been permanent.

Those measures didn’t “work” simply because we all weren’t coming down with COVID; they worked because they they were keeping lawyers safe and, also, made the system faster, more efficient, and less expensive.

In a system based entirely on precedent, this wasn’t a surprise; I saw this all happening in November 2020: “8 months in, I haven’t yet seen the more comprehensive changes to court dockets and settings that I had expected. Instead, it’s been a little bit here, gauge the reaction, and then a little bit less in response. In the end, the court system seems to be only making minor tweaks to the ‘usual way of doing things,’ rather than embracing innovative models that could result in future improvements.”

Back then, it felt like we were missing a chance to really make things better. In retrospect, we absolutely did.


Going to court in modern downtown Nashville is a huge pain in the neck. Aside from the unbearable traffic, pedestrian congestion, beer trucks, and construction blockages, you also have to deal with expensive parking, onerous security, and, this time of year, southern heat.

Some matters and arguments may justify in-person hearings. “Bet the company” arguments? Custody battles? Life and liberty at stake? Sure.

The day I caught COVID, I was in court on a heavy docket, opposing a pro se hand-written nonsense Motion (seriously, a piece of paper with a frowny-face would have had more factual or legal basis than what I was dealing with). It was one of the busiest days in Davidson County that I’d seen in years, as I tweeted an hour into my wait:

An hour later, I was still waiting:

My pro se defendant never even showed up, so I ended up winning, but I also sat in a busy courtroom from 8:30 to about noon, just watching other cases (big and small) get argued and responding to emails.

I’m not mad at the Judge on my matter (who is awesome); in fact, when my case was called, he apologized and I assured him that “somebody is last on every docket.” It’s part of being a litigator, right? (Plus, I get to bill for all that.)

But, on a broader level, what’s keeping the court system from putting policies in place that separate cases on a mega-docket into “Will take 30 minutes” and “Will take 5 minutes” stacks and, then, “No hearing needed” or “Phone hearing” stacks?

The Judges can’t enjoy this present system, where 20-30 matters of varying complexity are randomly jumbled together on a Friday morning and the Judges are forced to play whack-a-mole, mixed with lightning-round legal analysis.

If this system is just out of habit and custom, let’s fix that right now. Even without a global pandemic, this can’t be the best way to handle cases.


In my personal life, I’ve valued health and safety over really fun things, like Grizzlies playoff games, exotic trips, and karaoke. But, in my professional life, it’s frustrating to take on so much risk, when it’s both unnecessary and unjustified.

Two years in, we have all this experience and technology, but, nevertheless, we are handling hearing dockets than the same way we did it 100 years ago.

My sharing this experience isn’t meant to complain or scold anybody, but to talk openly about my experience. I know so many lawyers and court staff who have caught COVID in court, but we don’t talk about it, because…it’s embarrassing or we don’t talk about being sick? I don’t know. But, if not talking about it means that we don’t realize it’s a problem, then I hope my story starts that conversation.

In the end, my COVID has passed pretty easily, but I also worry about the people who I came into contact with on Sunday and Monday, before I realized what I had.

What’s worse is, as I type this on Friday morning, my 9 year old daughter woke up with a fever. All because I sat in court last week for 3 plus hours on something that should have taken 3 minutes.

The biggest COVID risk for our family has always been me.

People are getting sick, and we have the ability to reduce the risk. Why aren’t we? What I can do to help?