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10 Minutes with Legal Tech Entrepreneur Gary Kinder

By Luigi Benetton


Legal technology entrepreneur Gary Kinder earned a law degree, but he didn’t go straight into the law. Instead, he taught writing at his alma mater, became a published author himself, and began traveling the country teaching lawyers how to write.

It was during this decades-long teaching stint Kinder realized he could leverage his passion for writing and teaching to create software that helps lawyers hone their skills. In 2011, he launched WordRake Holdings, LLC, and released WordRake 1 in 2012. (Version 3 was released earlier this year.)


When do you wake up? Sometime between 5 a.m. and 6 a.m. I don’t set an alarm unless I have a flight.

What’s the first thing you do after waking up? To please everybody, I put clothes on first, then usually go straight to work. I’ll work for two or three hours before I get something to eat.

Where do you like to work? I have an office separate from the house, adjacent to where I live here in the woods in Puget Sound.

What time do you go to sleep? Around 10 p.m. I would like to get to sleep at 9, but it never seems like I can get there. I like to get a decent night’s sleep and be well-rested the next day. That’s when I get my best work done.

What’s your email strategy? If we’re working toward a new build, a new version, a new release, I’ll turn off my email for four or five hours in the morning and work quietly. I’m like most people. If something dings, I get distracted.

What’s your best productivity habit? Turning off email is one. Then there’s consistency, working every day. When people rush anything, there are always mistakes. I try to pace it, get stuff done every day.

What’s your favorite productivity tool? (You’re not allowed to say “WordRake.”) I’m not? Well, OK. I love my database. It’s set up just for me to produce WordRake. I enjoy working inside that. I’m a bit of a Luddite, not somebody you would think of as the founder of a technology company.

What’s the one habit you wish you could kick? I’m sure I have some … you should ask my wife or my daughters.

Do you want me to go there? OK. Little things … chewing ice is probably not the best thing for you. I drink a lot of hot tea. I get to the office early and it’s cold outside, windy, snowing, so I like a couple mugs of hot tea. I assume it’s OK for you.

Chewing ice and drinking hot tea? My dentist warned me about that. With the temperature difference, it would crack my teeth.

What do you let slide? When a communications service provider (names omitted to prevent legal repercussions) bills me for something I didn’t order, or I can’t read my bill, I want to call them and straighten that out. I set that aside in a pile. The idea is I’ll call tomorrow or next week. The problem is, I know I’ll be on the phone for two hours, and at the end of the call I might not get satisfaction. Because of that, I shy away from those things and they tend to pile up.

I’m not a great correspondent. I get a lot of responses to the WordRake writing tips I send out every week. I just can’t respond to everybody.

What’s the best advice you’ve ever received? We take life too seriously. We need a sense of humor. Don’t sweat the small stuff, and it’s all small stuff.


Tell us about your decision to start a technology company. I wasn’t ready to practice law right out of law school. When I graduated, I accepted a position teaching writing at the law school. Later, I ended up in Sun Valley, Idaho, working as a bellman. One day a week, I was a prosecutor. I had no debts, no relationship and no school, so I started writing as a hobby. The more I wrote, the more I loved writing. After several years I got my first book published (“Victim: The Other Side of Murder”).

I got married and had two girls. I needed more income than I could get from my books, so I moved to Seattle. I thought I could be an in-house editor and help train associates. But I couldn’t get anybody to see that lawyers need editors.

I thought it important that lawyers have access to qualified editors, people who understand law and writing. I traveled around the country teaching writing to big law firms for about 27 years. I began to notice “flag” words (like “of”) that signaled the presence of needless words and developed a process of looking for those words. One day, I realized I had not spotted anymore “signs” of bloated writing, so I applied for a patent. (That’s a long, long process, but potential investors are impressed when they see that you have a patent application.) That first patent was granted about four years later, on Christmas Day 2007, if you can imagine that. WordRake now has seven patents.

What business problem are you solving? Lawyers, like a manufacturing plant, have a product. That product is ideas in writing. They want to make it as good as they possibly can. That’s what WordRake can help lawyers and other professionals do.

Most people who work in a business atmosphere, from insurance companies to real estate companies — even manufacturers, engineers — have to write. Often, that writing is an interface with the outside world. If that writing is not crisp and not grammatically correct, it affects the image of the company.

When you write to your colleagues, your writing affects the image your colleagues have of you. It’s unfair, but that’s the way it is.

What have you had to change in response to customer feedback? We launched the Microsoft Outlook version in 2014. As for Macs, we’ve had people screaming at us since we launched. Many educational institutions want to use WordRake, and many students are on Macs. (Spoiler alert for Mac users: Watch for an announcement from WordRake later this year.)

Otherwise, people always want it to be broader and more accurate.


First, be patient. Restaurants are advised to have enough capital for five years because it will take that long for the public to find you. The same goes for technology companies.

Remember you’re competing for mindshare. And you aren’t even competing against companies with similar technology. You’re competing for attention from people who are just looking for diapers online.

Finally, when looking for investors, don’t take money from people who don’t understand your goal. Make sure they understand and buy into your vision and they’re willing to let you take time to get the business off the ground. Don’t just accept money because it’s money.

Read more about legal technology startups here.

Illustration ©, photo courtesy of Gary Kinder.

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Categories: Innovation, Interview / Enterprising Lawyer, Legal Technology, Legal Writing
Originally published March 9, 2017
Last updated October 5, 2020
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Benetton Luigi Benetton

Luigi Benetton is a business and technical writer specializing in a wide range of information technology and business topics. He blogs about tech and his passion for cars at TechnoZen and is fluent in several languages.  Follow him @LuigiBenetton and contact him at

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