Podcast #89: Starting a Solo Practice, with Mac Power Users Podcaster Katie Floyd

During this week’s podcast, Aaron and Sam discuss why sometimes lawyers should shorten written content, and Sam talks with Katie Floyd, co-host of the Mac Power Users podcast, about setting up her solo practice and tips for Mac and iOS users.

Katie Floyd


After nearly 10 years of working in larger firms, Katie Floyd fulfilled a life-long dream and opened a solo practice with the goal of providing personal and practical solutions to client problems. She believes that technology is the great equalizer for the small firm and solo practitioner. She is nationally recognized for helping individuals and small businesses make the most out of their technology and speaks regularly on the use of technology and the practice of law for the American Bar Association and others. She is also the co-host of the Mac Power Users podcast, which provides tips and tricks for both Mac and iOS users.

You can follow Katie on Twitter, Facebook, and LinkedIn.

Thanks to Ruby Receptionists and Xero for sponsoring this episode!

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Sam: Hello. I’m Sam Glover.

Aaron: I’m Aaron Street and this is episode 89 of The Lawyerist podcast where we talk with Katie Floyd, co-host of the Mac Power Users podcast about setting up her solo practice plus tips for Mac and iOS users.

Sam: Today’s podcast is sponsored by Xero. Beautiful legal accounting simplified. Find out more at xero.com. That’s X-E-R-O.com.

Aaron: Today’s podcast is also sponsored by Ruby Receptionists. Ruby answers our phones here at Lawyerist so that we don’t have to worry about getting interrupted when we’re being productive and we think it’s awesome. Visit callruby.com/lawyerist to get a risk free trial with Ruby.

Sam: Aaron, this week I want to mention 2 things and see if we can kind of synthesize them and come up with some advice for people, and that’s-

Aaron: Doritos and tacos.

Sam: No, not Doritos and tacos but similar-ish? I don’t know. The Clio Cloud Conference, Gary Vaynerchuk gave the closing keynote and essentially what it was all about is he was just emphasizing the importance of creating great content with your potential clients and referral sources in mind and then putting it out there on Facebook or Instagram or YouTube and building that audience and earning those clicks or buying those clicks.

Aaron: I think he even said all successful lawyers should be publishers.

Sam: Yeah. His sort of thrust is that everyone is a media company first because you have to get attention, you have to get people to pay attention to you and then you can sell your services to them, which lots of people resist and lots of people are just gaga over and think he’s the greatest thing in the world. I guess I’m somewhere in the “Oh, I think he’s right,” but then another piece came out on Poynter, which writes about the media, and The Washington Post just decided that its articles were getting too long and a directive came from on high saying “Unless you have a good reason, keep your articles to 1500 words or less.”

That doesn’t mean that they’re not going to do amazing long form content like this great piece on cobalt mining I just read, they’re going to continue doing that but unless there’s a good reason, articles should stay to 1500 words or less and they’re basically just saying that they’re abusing their reader’s time which is interesting and so I guess the bigger question here is if you’re going to be doing what Gary says and creating great content, putting it out there, how should you be thinking about how long it ought to be and how it’s formatted and that kind of stuff, because I’m not sure it’s always obvious and there are a lot of rambly lawyer videos and blog posts out there and so I’m kind of curious how should we be thinking about that.

Aaron: I guess my initial instinct, like my gut reaction is to recoil at the idea that because of social media and attention spans that everything just needs to be shorter because we just can’t stand to read, but the more I think about it, the more I recognize that the goal here is attention and the goal is to provide information in a way that your audience will understand it and hear it, and so you have to be where they are, and in the newspaper business that means you want people to be able to know enough about all of the major topics in the world over the course of their commute, and so they need to be able to skim the whole front page and read some interesting articles but people don’t spend 2 hours reading a morning paper anymore and that needs to just be okay.

I’m a newspaper subscriber, I read the newspaper in print paper every morning but I recognize that I also want to kind of know all of it a little bit more than spending hours on one article.

Sam: One thing that it suggest to me is that you should think about your user’s time obviously and their attention. At Lawyerist, our directive is you should do justice to the subject. You should be thorough and we’re not really as concerned with the length as we are with thoroughness, but this makes me think, well there’s more to it than that, right? We try to respect our readers by using headlines or subheadings that guide people through the article and an introductory paragraph that gives the overview because my assumption has always been that most people only read the title. After that, some people will read the first paragraph to see if this is something they want to read, and then they might scan the subheadings to get the general idea, and so those pieces should give people the general idea.

I think I’m right about that and so maybe length is not as important as helping people assess, get something out of your article without really reading it and then giving them enough if they choose to go deeper to get more. I don’t know how that translates to video necessarily because you can’t let people skim an outline of a video very easily.

Aaron: I think how it translates, how it ties into kind of the Gary Vaynerchuk model and how it’s useful for lawyers to at least think about how they could be doing some stuff is there is now this trend in Facebook, Instagram videos of 1 to 2 minute videos with interesting video content and overlaid text that’s kind of rapid fire overlaid text and you can convey by combining interesting visual content with well written but very short text content, you can convey a fair amount of information in just dozens of words, not even hundreds or thousands, and those at least in the current of multimedia online content are the kinds of things that are performing really well on the internet do a great job of conveying a small amount of information and are interesting for readers and catch them where they are because it is absolutely a fact that no one wants to read a law firm’s full length press release about a case they won or an award an attorney got or whatever.

Sam: Unless you do it interestingly.

Aaron: That’s what I’m saying. No one wants to read the full length press release. That is not to say that no one is interested in knowing what happened and I think lawyers too often get caught up in the form of press releases in the format that press releases are supposed to be written or maybe blog posts that look a hell of a lot like press releases as they’re supposed to be written but do it more interesting and have a picture of a happy client who allows you to have their picture and a picture of the lawyer in court and whatever overlaid with “We just solved this client’s problem and got them an award.” That could be an interesting 30 second video that’s going to convey as much or more information to your potential future clients or referral sources as a press release and you’re taking it to where they are.

Sam: You’re totally on about the press release thing. It makes me think of related problem that we have with writers on Lawyerist, and all of the writers on Lawyerist, most of them anyway, are out there trying to get clients, most of our writers initially have a tendency to sort of wander into the subject. In newspaper lingo, they bury the lead on the second page, and lawyers have this tendency to kind of like give a lot of background before they actually get to the point and the problem with that is most people decide whether or not to stay on the page. That is watch the video, scroll down, read more in about the first 3 to 10 seconds. Somewhere in there. Some people are a little more patient and they give you 10 seconds, some people shut the video down if you haven’t got their attention in the first 3 seconds.

If you’ve taken up that 3 seconds with your firm logo or you’re giving a long introduction to your subject, you haven’t made the pitch for stay on this page and keep reading this thing, and it strikes me that maybe the rest of the length is totally irrelevant, it’s whether or not you grab the person in the beginning and then you can go on and giving them more and more and more detail if you want as long as you’ve laid out in a friendly way, so maybe it’s not so much about length, maybe it’s really focusing on how do I make the pitch to the reader or the viewer or the listener that this is something that they really should stay tuned for.

Aaron: Yup. I think that’s right or even just not even stay tuned but just know that you’re never going to get lengths of attention and therefore have your actual content just be 20 seconds long.

Sam: That is an interesting strategy to.

Aaron: Just give it to them, which in the case of blog posts, like you don’t want a 60 word blog post, at least not as your average, but a 20 second video is totally acceptable.

Sam: In fact, I would rather watch a 20 or 30 second video than a 5 minute video.

Aaron: Especially if in those 20 seconds, there was 20 seconds of content.

Sam: Yeah. Now that we’ve talked about the importance of shortening up content, I’m going to go ahead and move to my conversation with Katie Floyd who does the opposite. I think none of her podcasts are probably shorter than an hour but it’s the very popular Mac Power Users podcast and she recently just started to practice and I think you’ll really going to enjoy my conversation with her about that process.

Katie: My name is Katie Floyd. I’m probably well known on the internet for my podcast “Mac Power Users” and my blog over at katiefloyd.com, but during the day, I’m also an attorney, I practice primarily in the area of estate planning, guardianships, probates, and some landlord tenant law as well.

Sam: Fair warning for the listeners, we are going to geek out a little bit about Mac stuff, potentially more than just a little, but one of the reasons I’m having Katie on is because she just went out on her own and is starting her own practice and so that’s really interesting to talk about too, but Katie, maybe first, tell us a little bit more about Mac Power Users. How did you get into this while being a lawyer and practicing full time?

Katie: That’s a good question. The Mac Power Users podcast I think has been going on since 2009? I stopped counting the years at some point but I think 2009. David Sparks who I know has been on your podcast in the past and I have been good friends for a long time and we both met in person at a Mac World back when they held Mac World several years ago. It was the year that the original Macbook Air was announced is how I date it because they had Macbook Air suspended from the ceiling, and we had several common friends and all of our friends got together and said, “Well, hey, you’re an attorney and you’re an attorney and you both use and like Macs so you guys should get together and do something.”

Sam: Ironically, the podcast has nothing to do with practicing law.

Katie: No, it doesn’t, so we did, it took us several months to figure out what we wanted to do but David and I were both very interested in productivity. You’ve got to remember, the iPhone was in its infancy at this point, there was no iPad, we were very interested in helping people use their technology to be more productive so the title is was very much aspirational. We have a lot of attorneys who do listen to our show, a lot of small business owners, a lot of people who want to use their Macs more productively, and of course now since the iOS has become such a big part of the Apple ecosystem, we of course cover that quite a bit as well.

Sam: The name notwithstanding.

Katie: Yeah. I think if we had known that iOS was going to be such a big thing back when we launched the show, we might have named it a little differently, but it’s teaching people how to use their technology in a way that helps them live their lives and get more work done which is certainly things that are very important to David and I and to most attorneys.

Sam: One of the things that I learned about you listening to I think the last episode of Mac Power Users was that you are not necessarily a upgrade every single time it upgrades. I think you’re waiting for your brand new iPhone 7 but you’re currently using an iPhone 6 which is exactly the position I’m in.

Katie: I was except my iPhone 7 arrived yesterday.

Sam: Okay. Just because you write and talk about being a power user, part of that doesn’t necessarily have to be upgrading every moment that a new thing comes out.

Katie: That’s true because probably more than anything, I am … some people would call it cheap, I would call it frugal.

Sam: That sounds about right for me too. Tell me about how you came to start your own practice. What were you doing before and what you wanted to keep doing, why did you decide to go out on your own?

Katie: I’ve been working for about 10 years as an attorney now. I’ve been happily employed for that entire time so I feel very fortunate, and a couple of things all came together to make the timing for this right. I’ll call myself somewhat of a recovering litigator although admittedly, I do still love litigation and keeping my toe in litigation but I don’t like fighting with people all the time so I was looking to transition a little bit out of all litigation all the time.

A couple of years ago, due to kind of a personal crisis and my own family got exposed very directly to the world of elder law and what happens when as family members age and things happen and they’re no longer able to care for themselves and what happens when you have a plan, what happens when things don’t go according to plan, what happens with all of those end of life type things and realize that a lot of people don’t have help going down this path or maybe they put together a plan but when they put together a plan, they didn’t anticipate how things were going.

A couple of years ago, after I’ve been practicing as a litigator for many years, I decided to shift my practice a little bit and go back to school and went back and got my LLM. I got my LLM in taxation. My particular focus was in the estate planning area of that and because I was working full time while I did that, it typically is a 1 year program done full time, it took me a couple of years to complete that program and people who’ve listened to Mac Power Users have kind of lived with me through that program as I’ve been working full time and a part time podcaster and part time student, but I finished up that degree in May and a bunch of things kind of came together, it seemed like the right time to go out on my own.

My good friend David sparks did it about a year ago and was very helpful to me in that pursuit. I’m very fortunate that I have a fairly good base of clients that I felt maybe I wasn’t going to starve if I went out on my own and very fortunate to be practicing in a community where I was born and raised and have been living most of my life so I had a good base of just friends and family and referral network that I’ve been growing for a long time and so far it’s been going well.

Sam: That’s awesome. You make it sound so casual and I know that those of us who have started their own businesses look back and are like, “Okay, I just did it.” Was it a hard decision or was it really just like, “I kind of want to go out on my own, I think I’m going to try it.”

Katie: It was easy and it was hard in a couple of different ways. It was something that I’ve always been interested in doing, it was something that is always been on my radar, and like I said, the timing for a lot of things just came together to “Why not now?” Certainly, a lot of planning and preparation went into it. I’m a very risk aversed type of person and so this was something that I’d been thinking about for several years before I did it. I think if you had me back on this podcast a couple of years from now, I’ll probably tell you that I wish I had done it years earlier.

Sam: I think so.

Katie: That tends to be what I hear from people so I wasn’t going to do it until a couple of milestones had been met, until I knew that I had certain amount of saving goals achieved that I knew I could survive for a certain period of time even if there was no income coming in because again, I tend to be very risk averse and I know that there’s certainly no guarantees in anything but I wanted to put myself in the best possible position to be able to grow the practice slowly and the way that I wanted to because I also wanted to be in a position where I could be very particular about the types of cases that I wanted to take. I’d never wanted to be a jack of all trades and a master of none and I wanted to be comfortable especially as a solo to be able to say no to things, to say that’s really not what I’m interested in doing and it’s really not something I’m comfortable to do.

Sam: How many months of savings did you try to get in the bank before you went out on your own? People love to ask that question before they go solo.

Katie: Without giving any specific numbers, I would say comfortably an excessive 6 months.

Sam: That’s fantastic. I always tell people as many as you can, but 3 to 6 months is probably a base. Do you have a spouse who is able to help support doing this or are you kind of like you’re going with no parachute other than the one you’ve stitched yourself with savings?

Katie: No, just me and my parachute here, and that was one of both the terrifying and deliberating things about it. I am single, I do not have any children at this point, so on one hand it was a great time to be able to do that because there was nobody relying on me except me but on the other hand, it’s it also terrifying because there is no plan B. There is no other spouse that’s working but if things don’t work out well that there’s anybody for me to rely on. There’s no one else who has an employer paid insurance policy that we can hop on or anything like that, it’s just me, and so the answer to all of my problems and all of my problems is me.

Sam: I don’t ask people to hand over their income statements and I know you’re a month in but I’m curious, how are you? Are you feeling optimistic right now? Are you still in the honeymoon phase or are you worried about when your next client is going to pay an invoice?

Katie: I actually haven’t sent out any of my invoices yet. As we record this, it’s actually the 28th of the month so I’ll be sending out-

Sam: Sure.

Katie: I’m very worried about are my clients going to pay my invoices right now.

Sam: You have some to send.

Katie: I do have some to send and I did take a sneak peek because I can do some quick reporting, and it looks like I’ll be sending out invoices that will probably be about on par with what I was making pretty steadily at the old shop. Now obviously, I will have to cover expenses and overhead.

Sam: Yeah, but that’s fantastic.

Katie: Obviously, for month one, I think that’s not too shabby.

Sam: That sounds like a win for months 1 through 3, through 6 through 9 as well. I guess you alluded to it but sometimes when people go solo, they have like a really well defined philosophy of how they want to practice law, their client service model innovations that they want to incorporate. Do you feel like you have kind of a cohesive strategy or philosophy of how you’re approaching this or are you sort of taking it slowly and seeing what emerges?

Katie: I think one of the biggest reasons that I wanted to go solo is because I wanted to be able to decide how things were running on my firm. I had a lot of flexibility at some of the previous firms that I worked at and then also none at some of the other firms that I worked at and I wanted to be the one who’s able to say, “You know what? I think there’s a better credit card processor that we should be using because this one offers these features and the one that we’re using only offers those features, so we need to switch.” I think that there’s a better way of handling file management so I think we need to switch and I wanted to be the one who’s in charge of making all those decisions. Maybe that was me being a little bit of a control freak.

One of my complaints about some of the other firms that I’ve worked for, and I haven’t worked for that many, is that sometimes they would say, “Yeah, that’s a good idea. We’ll look into that,” and sometimes they’ll just say, “There’s no problems. Everything that we’re doing is perfect. What could possibly be wrong?” I really like being the controller of my own destiny and especially in kind of the Mac power users side in me likes to be able to fiddle a little bit with the technology and decide, “This is the software we’re going to use, this is the solutions we’re going to use, this is the solutions we’re going to use, this is how we’re going to manage our files, this is how we’re going to do those types of things, so one of the big draws for me is being able to have a cohesive experience, and I’m not sure if I’m answering the question that you asked.

Sam: You were but you also prompted me to go off on a tangent here which is maybe a little bit closer to your Mac Power User’s world which is how do you balance doing productivity that is fiddling with your tools and trying to refine them and get them better, because you were talking about part of your desire was to have greater control over how things are done and the tools you use, so how do you balance your desire to optimize versus actually being productive in getting things done?

Katie: That’s hard because I’ll tell you, when I made the decision to go solo and I told some of my law partners, some of them were terrified. They’re like, “Are you crazy? You’re going to have to figure out how to manage files and how to do accounting, you’re going to answer your phones, all that.”

Sam: You’re like, “I know.”

Katie: I’m like, “I know. Isn’t that great?” As a geek and someone who enjoys some of the fiddly stuff of this, sometimes it definitely can be tempting to want to play too much with some of these systems that we’ve put in place rather than actually practice law, so that’s something that I definitely am trying to be aware of, and so these first couple of months especially, I tried to put some systems in place before we even open the doors. September 1 was when we officially launched The Royal We, that would be me and I guess Ruby, and so I’m trying to hold to that and if something doesn’t absolutely need changing, I’m trying to stick with that probably at least through the end of the year before I make major changes and then evaluate and see where to go from there, but it is and so far, so good. I’ve helped study to that but it is very tempting to be fiddling.

Sam: Yeah. I have that problem too and then I got totally obsessed with getting things done for years and then all of a sudden I realize that I’d been using the same set of tools for a long time but also that I could switch tools with no switching time because I had a procedure that I could apply to anything, and then that was a little bit freeing when I realized I didn’t have to care about my tools as much as I used to.

Katie: I guess I had a couple of overarching goals that I wanted to implement. I knew very much that I wanted to implement as much as possible a paperless practice. That was something that was very important to me. I knew that I wanted to have a practice where I could work from anywhere. I wanted to be able to work from home just as seamlessly as I could work in an office and having an office that’s very customer service oriented with estate planning, that was something that I had to have.

In fact, that is to this day continues to be my largest expense is I’m in an office share type of arrangement but I have a very nice office because I have to meet with clients, I have to have a conference room for the type of clientele that I’m catering to, I have to have a presence, and I get a big fancy brick building with signs out front and ample parking and books in the … They’re not my books, but books in the conference room shelf that I go to everyday, but I also wanted to, if after hours or on the weekends wanted to get work done, I didn’t want to have to go to that office, so I knew that I wanted to set some things up in very specific ways that I could get work done from everywhere, that I could get work done from home, from the office, and even be as mobile as possible to the extent I could on iOS.

Sam: I imagine you’re at the point in your starting a practice journey where you will work as much as you need to get work done because you’re not really all that interested in turning things down, right? At some point, you need to start, I imagine you’ll find that you want to start drawing more lines. We had Kristin LaMont on recently who said that going mobile was great but also a challenge because people felt like they were working all the time when before, they could only work from their desks. How do you think you’ll balance that? The ability to work all the time with feeling like you actually have to?

Katie: One of the benefits of having an office and having a dedicated office space thus far, and again it’s only been a month, unless I had a very good reason not to, I have established pretty routine office hours. I’m typically in the office by 8 or 8:30. I’m a morning person so I’m usually up and in there anyway, and I’m typically looking to go home around 5:30 or 6, so unless I have something that has to get done, I’m pretty much done. I have tried to establish general office and working hours and try to make an appearance in the office and my general philosophy has been if you’re in the office, you can kind of make things happen, and if you’re at home working from the couch, sometimes it’s a little bit easier to let things slack, at least for me. I know it’s not necessarily true for other people but it’s always been very helpful to me to get up and go in the office and do things.

That’s how things have been working for me but I agree, it’s very important to have those lines. I have worked probably most weekends but I’ve tried to limit that to more administrative stuff. One weekend was kind of a QuickBooks weekend, one weekend was kind of a file scanning and archiving weekend of taking things from the old firm that they’ve given me in paper and digitizing them to get all that paper out of here and doing those types of things.

Sam: Very cool. We’re going to take 2 quick minutes from our sponsors and when we come back, I want to start talking about some of the tools that you’ve alluded to.

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Sam: This podcast is supported by Ruby Receptionists. As a matter of fact, Ruby answers our phones at Lawyerist and my firm was a paying Ruby customer before that. Here’s what I love about Ruby. When I’m in the middle of something, I hate to be interrupted, so when the phone rings, it annoys me and that often carries over into the conversation I have after I pick up the phone, which is why I’m better off not answering my own phone. Instead, Ruby answers the phone and if the person on the other end asks for me, a friendly cheerful receptionist from Ruby calls me and asks if I want them to put the call through. It’s a buffer that gives me a minute to let go of my annoyance and be a better human being during the call.

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We’re back and Katie, you start a law practice not just as a lawyer with a decade of experience but you have been deep in the weeds on what’s available for productivity and anything else for Mac users, for iOS users and web users honestly, so when you start thinking about how you’re putting your practice together, what kinds of tools did you adopt right away, what kinds of tools are you considering adopting soon, and I get that you’re not even yet a month in but you’re well beyond a month of being a lawyer and well beyond a month of practicing productivity and law practice, and so I’m kind of curious as to how you approach that figuring out what to get which occupies a large part of the stress and concern of new lawyers everywhere.

Katie: A lot of it was based on what did I already have and a lot of it was obviously based on the fact that I am very Mac and iOS based. I run a podcast that’s Mac Power Users so I was not going to have a piece in my office. Though as someone who does estate planning as you might imagine, a lot of that software is still pretty proprietary PC base, so although I do have a Mac Mini in my office that’s my primary workstation, I’m also running Windows in parallels which is a virtualization software because when I actually have to draft, I’m drafting in a PC application on that virtualized PC.

Sam: What’s that software?

Katie: It’s called Lawgic, L-A-W-G-I-C.

Sam: Okay.

Katie: I think they’re more popular in Florida and a couple of areas. I don’t know if they’re necessarily nationwide. I think they picked a couple of states that they really hone in on, and so that’s what I use for my estate planning drafting, but that’s really the only thing that I boot the PC up and at this point, it’s really when I have an estate plan to draft and then I close it back down and do all of my tweaks just using Microsoft Office.

Sam: I heard you mentioned QuickBooks earlier. You’re paperless and I imagine that means a ScanSnap for you.

Katie: Yes. On the finance side, I really didn’t know what to do. I have a good friend who is my personal CPA and has done my taxes for years, and so I just said, “Okay, so this is what I’m doing, you’re going to do my business taxes. Tell me what I need.” She told me that I needed to do QuickBooks online and that was so that she could have access and I could access and so I said, “Fine. Sign me up, whatever I need to do,” so I’ve got a QuickBooks online program. I was not thrilled with some of the billing implementations so I’m using another application for billing.

Right now, I’m using Harvest. I don’t know whether I’ll continue with that but I’ve been very happy with it and it’s fairly inexpensive. It’s like for a solo, it’s a $12 a month add on but it’s got good implementation for time tracking and for invoicing and it does things like being able to let you send invoices electronically so I’m totally paperless and sending invoices out to my clients and then they can actually pay me electronically as well so it will tie in with a couple of payment processors so they can pay me electronically, and I’ve also setup LawPay so I can accept credit card payments and one of the reasons I use that is because they’ll keep money segregated between the trust and the operating account which is very important because I do take retainers on matters that is money that’s not earned for me.

That’s one of the ways because billing is huge, billing is one of the biggest paper generators in law offices and that’s one of the ways that I’m able to keep my billing completely paperless, but for the other stuff, yes, you’re right. I do have a ScanSnap, a Fujitsu ScanSnap iX500. I have actually 2 of them. I’ve had one on my desk at home for years and thought about taking that into the office and realized I was not willing to give it up, so just bought a second one to go in the office. I tend not to generate a lot of paper with my practice. I’m doing a lot by signing PDF’s and we are all electronic filing in Florida now so I don’t generate a lot of paper. Those things just stay on my computer in electronic format but any time a client gives me anything, right there in the office, I will scan it in and then typically hand the originals back to them.

In fact, I’ve actually written that in my retainer agreements with them. I’ve got a section that’s devoted to document and file storage and handling where I talk to them about that I’m a paperless office, that I do not keep original documents unless it’s absolutely required for their matter and that after so many days, after their matter is closed that after I’ve made an attempt to return them that I can discard them and those types of things.

Sam: It’s a smart thing to do. I did that in my retainers as well. It’s funny, I have a ScanSnap iX500 sitting on my desk right in front of me right now too but I was just having a conversation with Aaron, my business partner, that I almost never use it. I open it up about once a month and scan a few pieces of the paper. When I had a practice, I use that more but I generate so little paper and once I converted all of my bills and statements and things to paperless and once I started communicating primarily via email attachments and things like that with opposing counsel, the amount of paper that actually came in my door really dropped. I’m sure if I was practicing actively, I’d be using it more but even still, 3, 4 years ago, I wasn’t generating much paper and I wasn’t using my scanner very much, so even though it’s like an essential tool, I feel like I can see the time when just being able to use Scanbot on my phone is all I need which is pretty much all I use now.

Katie: I actually use Scanner Pro on my phone.

Sam: I have that too.

Katie: Very similar app and what that will allow you to do is take a picture of a receipt or a document that will leave an OCR, find the edges, turn it into a PDC, and I’m sure we’ve all received pictures of documents from clients before and you’re just going, “Why did you send me this?” The Harvest app actually has a nice feature where if you have a receipt, you can take a picture of it and save it to the client account, and the QuickBooks app will also do that so you can keep track of your expenses that way.

Sam: You mentioned file storage briefly. Are you a Dropbox user or do you use something else to sync up client files?

Katie: I am a Dropbox user. I’ve upgraded to pro accounts and I know that was a little bit controversial of “Oh, you’re storing client documents in the cloud.” Florida actually does have an ethic opinion on that which basically they kind of punt it a little bit and said, “You just have to do due diligence,” so I’m using an appropriate pro type account for a business and so I definitely paid for my Dropbox storage and I’ve made sure that I have all the additional security features turned on. I’m using a good password, I’ve got 2 factor authentication turned on, I’ve got notification sets so that if something else connects to my Dropbox account, it will warn me, but it’s great because although I need to be very careful to say Dropbox is not backup, it is storing a copy of your files so it is kind of a poor man or a poor woman’s backup of some sort.

Sam: If you turned on the Packrat extension, it really is back up.

Katie: Right. That’s one of the things that allows me to basically work from anywhere because with Dropbox, my files are on my work Mac, my files are on my home Mac and I can access them anywhere on iOS. I’m also of course making local backups and I’m also doing cloud backup as well. I’m using a service called Backblaze to backup my documents both at work and at home, so there’s really … If anything happens, I’m pretty well covered.

Sam: My new favorite thing about the ScanSnap actually is with the last update or the previous to last update, the ScanSnap cloud option. I’ve unplugged my scanner from my computer and now I just run paper through it directly and it just goes straight to Dropbox and I don’t even have to worry about it which I love.

Katie: Yeah.

Sam: It doesn’t sound like you’re using practice management software yet.

Katie: I am not at this point. One of the philosophies that I went into this is like I said, I’m fairly frugal and one of my concerns was anything that I went into this practice with on day 1 was going to be very hard to get rid of, so I wanted to go in as lean as possible knowing that it would be much easier to add than it would be to get rid of, so I’m not using any practice management at this point, I’m using files and folders. Now I’m using some third party utilities on the Mac to help me organize those things. There’s a great extension, a system preference on the Mac called Hazel that will allow you to automatically rename and file things, and we’ve done several Mac Power Users episode on Hazel, and so I have a lot of Hazel actions involved to help me keep files organized and things like that but at this point, no, it’s just files and folders.

At some point, I might consider adding practice management but I don’t really feel like I want to do that until I’ve probably been doing this for at least 6 months because I want to be able to make an informed and educated decision of exactly what do I need, what features am I lacking, and what exactly am I going to use practice management systems for.

Sam: That is such a good perspective. So many lawyers think they need practice management software and go shopping for it when they don’t have a clear idea of what need they will be meeting with it and that becomes a problem when like if you’re an Outlook user, maybe that meets your needs and you don’t need to be looking at practice management software.

Katie: Again, you said so much as an email, I’m using a Gmail for work account so that’s more than archiving everything that I’m using. I’m also using a third party plugin for Apple Mail called MailTags and I’ve setup a couple specific rules so every time I open a new client matter, it will look at a couple of keywords, who’s the message to or who’s it from or is a couple of words in the subject matter and it’s tagging my mail automatically for me. “Oh, this must be related to the Smith Jones matter,” so it’s another factor to help tag my mail.

Sam: You mentioned Hazel real quick and I want to include links to episodes of Mac Power Users so that people can go see here are some examples of how to use it and what to use it for but can you give us a couple of examples because I know that it’s actually worth giving example of how you can use it because it is such a powerful program?

Katie: I should mention the best way to see what Hazel does is actually watch it in action and David Sparks has done a couple of field guides or a couple of video tutorials on Hazel. I think he’s actually done a video field guide on Hazel so you can actually watch what it does, but Hazel, what it will do is it will watch your files and if you scanned everything in with your fancy ScanSnapper or your scanner on your phone that has the ability to OCR and what that means is Optical Character Recognition, so to be able to pick out the words and see the words in your file, Hazel has the ability to now read the data in like PDF files and of course lawyers work and live and breath in PDF’s, so you can setup specific Hazel rules based on criteria and files.

Here’s a very simple one just for categorizing expenses. You mentioned Ruby, every month, I get a bill from Ruby and that file has a couple of key characteristics in it. It has my account number, it has Ruby Receptionist in it somewhere, so when I download that file from my, I think it’s emailed to me, that PDF invoice, when I download that from my email application, it goes to my downloads folder but it’s named something weird, so Hazel looks at that file, it sees that criteria that I’ve set up. Think of it like a series of If Then statements, so if this criteria is met, if you see this criteria in the specific file, then do these things and what I have Hazel do is rename that file consistent with my file naming system and that’s something that I think is very important especially if you don’t have practice management software to have a consistent way that you name and organize your files and to file it in a particular folder.

It’s going to file it in my business receipts folder under this category, and those are documents that I share with my accountant so that I know when my accountant is balancing my books for the quarter, she’s going to have access to that receipt, and so I do that with a lot of my ongoing monthly business expenses and then I also have similar categories setup every time that I open a new client matter, Hazel’s going to create a subset of folders and certain things that have certain criteria, like if it has a particular case number in it, those are all have … If you’re looking for a particular thing with a particular case number, it’s going to file it in that client folder.

Sam: That is super useful. I always had a manual system for copying over my file templates and I was always accidentally moving instead of copying and it’d be so easy to just grab something like that and make it happen automatically.

Katie, maybe let’s close with one of my favorite things to do with tech forward lawyers which is talking about some of your must have apps. You’ve mentioned some of the services you’re using but what are the things on your phone, on your Mac, on your watch if you have an Apple Watch that you just can’t imagine yourself living without honestly whether or not they have to do with your law practice?

Katie: I’ll try to give you things that are more productivity focused. A couple of things. Obviously, all the attorneys have to deal with calendaring so the app that I use for calendaring is one called Fantastical. It’s available both for the Mac and the iOS. One of the things that I like about it is an addition to it being a full fledged calendar is it has great natural language support, so I can write things in my calendar like “Record podcast with Sam Wednesday at 5:30” and it will automatically create a calendar entry for Wednesday at 5:30 titled “Record podcast with Sam,” and that also works well with dictation so it’s just probably one of the best calendaring applications that I’ve used, so that’s Fantastical.

Another one that I really think all attorneys can be using and it’s one that I recommend a lot for my clients and my estate planning practice is a password manager app. My personal preference is one called 1Password. I think LastPass is probably good as well, but we all know the horror stories of data breaches and what happens when your information gets compromised and the reality is that it will happen and it probably won’t be your fault, it will probably be someone else who gets their data compromised and you just happen to be an innocent bystander, but there’s only so much you can do to protect yourself but the single most important thing you can do is to have strong unique password across all of your sites and it’s a real pain to do that unless you’re using a password manager, so just to have that information stored somewhere else.

What 1Password does is it lets you store that information, it will randomly generate passwords, it will automatically log you in, and one of the reasons that I like recommending something like this for my estate planning clients is what is your plan? If you become incapacitated or in the event when you die, how is someone going to gain access to all of your digital assets? So much of our life is online now. How are they going to access your online banking accounts or even just your email and those types of things? I typically tell them as part of a comprehensive state plan, you also have to figure out how to plan for those digital assets as well, and so if you’re using something like a password manager, that’s just one thing that you have to keep updated and then provide instructions on how to access that and then your fiduciary is covered.

Sam: I know this is a digression but that’s a pretty interesting issue. How do you advice people to do that? Do you tell them to use a shared … My wife and I have a shared password. We use Dashlane, I use Dashlane, she knows that. We have a shared password. Dashlane also has a dead man’s switch which is nice. If I don’t use it for 2 weeks, it’ll automatically email her and let her know that I haven’t logged in and ask her if she wants to or it’s something like that. I know people keep half the password in a safe deposit box and give the other half to their spouse or someone they trust. Do you have a preferred way that you tell people to do it?

Katie: I think that’s a conversation you have to have with the client on a case by case basis based on what their comfort level is, the type of assets that you’re talking about and who the potential fiduciaries are because everyone’s circumstances are certainly different, and obviously what their comfort level is with technology, what I personally and what I think might be right for certain people was I’m comfortable, I keep all of my stuff in 1Password, I keep it updated, and then I have what I call an emergency kit and it’s not mine, I lay no claim to it.

I think Mike Vardy might have come up with this and I actually blogged about it on my law site and it’s basically a one page sheet with information that just basically says “Hi. This is the password manager that I use, this is how you access it, and by the way if you need to get into my computer, this is the password to get in my computer,” because you’re going to need a couple of bits of information just to get access to the password manager, and then I think it also has, “And if this makes no sense to you and if you need help, here’s the name of 2 of my techie friends who can help walk you through this.”

Sam: That is super smart. I’m going to include that link. Any other must have apps?

Katie: I’ve got a ton of must have apps.

Sam: I’m sure you have a long list. Give me 2 or 3 more.

Katie: Give you 2 or 3 more. OmniFocus is my to-do application of choice and to call it a to-do application is really an abomination. It’s really an entire GTD system. GTD is obviously the getting things done methodology. It’s based on a book written by David Allen many, many years ago that has since been revised and updated, but it’s kind of my external brain. It’s where I store everything that I have to do today, tomorrow, 10 years from now. One of the things I noticed is 10 years ago, I put a note in here to renew my passport and it just come up due, so it’s interesting that I’m using the GTD application now that I was using 30 years ago.

Sam: That’s amazing. I know a lot of lawyers use OmniFocus in place of a practice management software. I think David Sparks basically uses it for his practice management software.

Katie: That’s some of what I’ve done too because it’s great for calendaring, it’s great for followup, it’s great for making sure that you can note your deadlines, so there’s that. The other thing, and mine was pretty unique, I use a product called ZULTYS and MXIE, but I think having a basic VoIP solution is a good solution and find the obviously that works best for you. Some people like RingCentral, some people like Vonage. I went with mine because basically, a long time, a business and a client of mine happens to run a telecommuncations company and it worked out well for me, but having the ability to make and return calls from anywhere again kind of goes with that overarching philosophy of I want to be able to run my law practice from anywhere. I want to be able to run it in the office if I’m there where I have a dedicated phone on my desk but I also want to be able to return calls from my cellphone, from my iPhone without people knowing that I’m sitting at home.

Sam: You have a separate business phone number and that’s what you use that for.

Katie: Yeah, I have a separate business phone number, I have a separate business phone. It’s sitting on my desk but it also has a voice component that has an app on my cellphone that if I’m not in the office, I can dial through that app on my phone and I can make and receive calls from my cellphone as though I were on the other film, and I think Ruby can do this to some degree as well, I just happen to go through a different provider for that. For example, this might be kind of scary for someone who’s opening a new solo practice and I’m a little nervous about it but it was a pre-planned trip. I’m taking 2 weeks off in April. My family and I are going to Amsterdam in Holland in Belgium for 2 weeks to go see the tulips, so I’m still going to have to do some work, I can’t take completely 2 weeks off without having any access to work but I’ll be able to e-file, I’ll be able to email, I’ll be able to make calls, I’ll be able to do all of that just by taking my laptop and my cellphone.

Sam: Very cool. Before I say thank you and close, is there anything you wanted us to talk about that we haven’t talked about yet?

Katie: I think the overarching theme of my new solo practice and the way that I’m able to sleep at night is I’ve tried very hard to keep things simple. I can always add later. I think being somewhat frugal and being somewhat prepared for this has … By having savings and by starting off slow, that’s been how I’ve started, that’s how I’ve always been comfortable doing things. I think taking things slowly and building them up from there hopefully will serve me well. Today, I probably backed off of a client that if I were in a different position, I might have taken, but it’s one of those things in the back of your head you know this isn’t going to turn out well and I’m going to regret this if I ended taking it so why don’t I just not take it to being with?

Sam: One of my favorite post on our site is the clients you don’t take will be the best money you never made.

Katie: Exactly and that’s absolutely true. I think one of the best pieces of advice that a judge gave me once is the best decision you’ll ever make is to fire a client. I think going slow and coming at this from hopefully a position of strength and I think it’s at least what give some some comfort in this solo journey.

Sam: For what it’s worth, from somebody who had been there and done that, I think you’ve got the right approach, and I really appreciate you being with us and talking about your practice while it’s still in it’s birthing phase I guess. It feels like it’s in the process of becoming and it’s really cool to get a window and to how that’s happening, so thank you so much for being with us today.

Katie: It’s been my pleasure.

Sam: Make sure you catch next week’s episode of The Lawyerist podcast. Subscribe to The Lawyerist podcast in iTunes or in your favorite podcast app. You can listen to it at lawyerist.com/podcast. You can also subscribe to The Lawyerist Insider, our weekly newsletter. Just go to lawyerist.com and look down the side bar or click on “Newsletter” up at the top. We’ll remind you where to find the podcast whenever we release a new episode. Thanks for listening.

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