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Featured Guest
Katie Floyd

Katie Floyd is a litigator and co-creator and host of the Mac Power Users Podcast. She’s also a consultant...

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Aaron Street

Aaron Street is the co-founder and CEO of In addition to his work growing Lawyerist’s community of small firm...

Sam Glover

Sam Glover is the founder and Editor in Chief of Sam helps lawyers understand the economic, demographic, and...

Episode Notes

In this episode we check in with Katie Floyd, co-host of the Mac Power Users podcast, about her experience setting up her solo practice and the tools she uses to run it.

Katie Floyd is a Florida estate planning and landlord-tenant lawyer who 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.


Speaker 1: Welcome to the Lawyerist Podcast, with Sam Glover and Aaron Street. Each week, Lawyerist brings you advice and interviews to help you build a more successful law practice in today’s challenging and constantly changing legal market. And now, here are Sam and Aaron.
Sam Glover: Hi, I’m Sam Glover.
Aaron Street: And I’m Aaron Street, and this is episode 128 of the Lawyerist podcast, part of the Legal Talk Network. Today, we’re checking in with solo lawyer and Mac Power Users podcaster Katie Floyd, who we originally talked to barely a month after she started her solo firm.
Sam Glover: Today’s podcast is sponsored by Clio, legal practice management software. Clio makes running your law firm easier. Try it for free at That’s
Aaron Street: Today’s podcast is sponsored by Ruby Receptionists and its smart, charming receptionist who are perfect for small firms. Visit to get a risk free trial with Ruby. So this episode, we’re going to try something new and check in with Katie Floyd. She was our guest in episode 89. At the time she was barely a month into her new solo practice, and we thought we’d kind of follow up and see how things went with her, or are going with her. So here’s that update, then followed by a replay of the original interview.
Sam Glover: Hi, Katie. So, when we recorded your podcast, you were just a month into your solo practice, and you hadn’t even sent out any invoices yet, if I’m reading that transcript correctly?
Katie Floyd: I think that’s right.
Sam Glover: So you’re about eight months along now I think, right?
Katie Floyd: That sounds right. I started in September, and we’re here in July.
Sam Glover: All right, well my math may or may not be right, but that sounds close. So how’s it going?
Katie Floyd: Things are going great. I always tell people that I’m happier than I ever have been in my professional practice, but I’m also, the downside of that is I’m working harder than I ever have been before. But it’s a good thing because I’m working for myself and people around me just even notice. They just say, “You’re really, really happy.” And I was like, “Well I didn’t realize that I was that much of a pain before.” Something about working for yourself, I guess you don’t mind working that much harder.
Sam Glover: That’s very cool. Is there something that you feel like you’ve learned about solo practice that you didn’t know the last time we talked?
Katie Floyd: The thing that I learned, because I’ve really been keeping tabs on all of the numbers and things like that, is I didn’t realize that it never rains but it pours. I have gone through times where … In fact, right now, I always thought summer would be slow because we’re recording this … We’re very into June, early July. Summer has traditionally been slow for me, but I am really, really busy in my practice right now. But then, I might go several days and my phone will never ring. And sometimes I’ll call Ruby and be like, “Just checking in to make sure everything’s working.” And they’re like, “Nope, it’s all working.” So one of the things that I’ve learned is that you just have to really keep ahead, keep on top of the workload, buckle down when the busy time comes. And then, when the slow time comes, enjoy them, and then maybe have a few business building products on the back burner and go from there.
Sam Glover: Very cool. So you are one the Mac Power Users. Your podcast, I think, probably dwarfs ours in circulation because I suppose the passionate Mac users dwarf the lawyer population is I’m assuming why. But have you picked up any new tips along the way for running your practice that Mac users who are listening might want to know about?
Katie Floyd: Yeah. So a couple of things that I’m doing differently. The first thing is QuickBooks and I have finally learned to speak the same language.
Sam Glover: Oh, wow.
Katie Floyd: It took a couple of months, and my accountant just kept telling me to stick with it, stick with it, and she gave me some really good advice. She said, “When you start your practice initially, you will have more time than money.” And I was very, very tempted when I first started my practice to hire a part-time book keeper, or something like that, because I was very, very frustrated with QuickBooks. But I would say after about three months of due diligently doing it myself, something in my brain flipped, and I finally figured it out, and it’s not that big of a deal anymore. And the way that I’ve got it set up now is I’m doing all of my own entry. I probably sit down once a week and reconcile everything. All of my trust accounting is in QuickBooks, all of my operating expenses and accounts are in QuickBooks.
And if I have a specific question, my accountant goes in and looks at it, but she basically looks at it quarterly just to make sure that there’s nothing funky and that everything’s on the right track, and files my taxes, and it’s a pretty simple process. So one of the things, the advice that she gave me, she said, “You really need to get over that initial hump and learn how to do it yourself, because when you get to the point that you have to turn that over to somebody else because you’re so busy,” she said, “It’s very important that you know how to do it, because then you know how to keep an eye on it.” She says, “That’s how people get taken advantage of is you don’t know how to do it, and you really rely on somebody else, and then you don’t see what’s going on, and you don’t recognize when something bad is happening.”
Sam Glover: I suppose the flip side is that it can be really frustrating finding a good book keeper when you know how you want it to be done.
Katie Floyd: Yeah, I guess that’s true. But I’m glad I sucked it out. I’m glad I put the time in and ultimately figured out, because now it’s not that big of a deal. The one little tip that I’ll give people related to that, the mistake that I made is there are a couple of different levels of QuickBooks plans, and QuickBooks doesn’t let you downgrade. You can always upgrade, but you can’t downgrade, so I would say start off with the lowest level that you can and upgrade only if you need it, because I think I’m probably paying about 20 or 30 bucks more than I really need to for the level of service that I have, because it’s a really scary process that they … You have to like close down your business and export. It just absolutely ridiculous. And I’m sure it’s a money-making thing, but anyways. So that’s my one tip.
Sam Glover: Good to know.
Katie Floyd: Yeah. The other thing that I would say related to finances is I take credit cards now. And I would say that I also use an automated service. I ended up using Harvest for my billing. And I actually use that for my time tracking. I find that with my practice, I don’t need a dedicated practice management service. I’ve tried a few and I end up just going fine with files and folders, but I do use Harvest for billing and time tracking. My clients love it. I love it because I don’t have to send out paper invoices. My clients love it because they just get the invoice and they can pay online because people are so used to doing that. And I found that my AR has gone down significantly. I mean, I’m typically getting paid in 15 days or less, and I just don’t have an issue with outstanding invoices anymore.
Sam Glover: Very cool.
Katie Floyd: I do pay the credit card fee, but that’s just kind of the cost of doing business now.
Sam Glover: So, our listeners are about to hear a replay of our original discussion. So if there’s anything you want to clarify or qualify, now’s the time to do it.
Katie Floyd: Oh, the one thing that I will say. I didn’t realize how much time I would spend calendaring things and scheduling appointments. So I did pretty quickly sign up for the Calendly, C-A-L-E-N-D-L-Y, service, which now integrates with Ruby. So I’ve actually moved a lot of my scheduling online. My younger clients love it. My older clients, they call Ruby, and then Ruby can schedule for me through Calendly, and that works out great as well. So just those little hacks have been good ways to maximize my productivity.
Sam Glover: Fantastic. Well, thanks for the update, Katie.
Katie Floyd: Yeah, yeah. Overall, it’s going well, so hopefully it continues to. Check in with me in a year or so.
Sam Glover: Will do. Glad to hear it.
Katie Floyd: My name is Katie Floyd. I’m probably well known on the internet for my podcast, Mac Power Users, and my blog over at 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 Glover: And fair warning for 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 Floyd: So 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. 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 Airs 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 Mac, so you guys should get together and do something.”
Sam Glover: And ironically, the podcast has nothing to do with practicing law.
Katie Floyd: 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 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 Glover: The name not withstanding.
Katie Floyd: 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 Glover: And 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 Floyd: I was, except my iPhone 7 arrived yesterday.
Sam Glover: Oh, okay. But so you don’t … Just because you write and talk about being a power user, part of that doesn’t necessarily have to be upgrading on every moment that a new thing comes out.
Katie Floyd: That’s true, because probably more than anything, I am, some people would call it cheap, I would call it frugal.
Sam Glover: Yup. That sounds about right for me too. Tell me about how you came to start your own practice. I mean, what were you doing before and why wasn’t it what you wanted to keep doing? Why did you decide to go out on your own?
Katie Floyd: So 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. And a couple of years ago, due to kind of a personal crisis in 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 realized 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. So a couple of years ago, after I’d 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, and 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 one year program done full time, it took me a couple of years to complete that program.
And people who have 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, and 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. 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.
Sam Glover: That’s helpful.
Katie Floyd: And very fortunate to be practicing in a community where I was born and raised and have been living most of my life, so had a good base of just friends and family, and a referral network that I’d been growing for a long time, and so far it’s been going well.
Sam Glover: That’s awesome. You make it sound so casual. And I know that those of us who have started our 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 Floyd: It was not an easy … 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 has 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 am a very risk-adverse type of person. And so this was something that I had 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’d done it years earlier.
Sam Glover: I think so.
Katie Floyd: 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 that 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 adverse, 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 in 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 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 that’s really not something I’m comfortable to do.”
Sam Glover: How much saving … 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 Floyd: Without giving any specific numbers, I would say comfortably in excess of six months.
Sam Glover: That’s fantastic. I always tell people as many as you can, but three to six months is probably a base. Do you have a spouse who is able to help support during this, or are you kind of like you’re going with no parachute other than the one that you’ve stitched yourself with savings.
Katie Floyd: No, just me and my own parachute here. And that was one of both the terrifying and the liberating 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 also terrifying because there is no plan B. There is no other spouse that’s working that 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 Glover: So I don’t ask people to hand over their income statements, and I know you’re a month in, but I’m curious, 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 Floyd: Well, I haven’t actually sent out any of my invoices yet. As we record this, it’s actually the 28th of the month.
Sam Glover: Oh, sure.
Katie Floyd: So I’ll be sending out.
Sam Glover: Sure, yeah.
Katie Floyd: So I’m very worried about are my clients going to pay my invoices right now.
Sam Glover: But you have some to send.
Katie Floyd: 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, so and obviously-
Sam Glover: Yeah, but that’s fantastic.
Katie Floyd: -for month one, I think that’s not too shabby.
Sam Glover: That sounds like a win for month three, one through three, through six, through nine as well. So 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 Floyd: 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 run in 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 was 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 was in charge of making all those decisions. Maybe that was me being a little bit of a control freak. And when my … 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?” So I really like being the controller of my own destiny, and especially kind of the Mac Power User 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 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 Glover: No, but … Well, 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 Users 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 and getting things done?
Katie Floyd: Well, 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 like manage files, and how to do accounting [crosstalk 00:18:56]”
Sam Glover: And you’re like, “I know.”
Katie Floyd: “Answer your phones and all that.” And I’m like, “I know, isn’t that great?” And so 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 very aware of. And so these first couple of months especially, I tried to put some systems in place before we even opened the door. September one 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 held pretty steady to that. But it is very tempting to be fiddling.
Sam Glover: Yeah, I have that problem too. And then, I got totally obsessed with getting things done for years, and then all of the sudden, I realized 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 Floyd: I mean, 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, 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, a big, fancy, brick building with signs out front and ample parking and books on the … They’re not my books, but books on the conference room shelf, that I go to every day. 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 Glover: And I imagine you’re at the point in your starting a practice journey where you will work as much as you need to to get work done because you’re not really all that interested in turning things down, right? But 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 Floyd: Well, one of the benefits of having an office and having a dedicated office space is 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 8:00 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 6:00. So it’s been … And unless I have something that has to get done, I’m pretty much done. So 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.
That’s always been, 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. So 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 had given me in paper and digitizing them to get all that paper out of here and doing those types of things.
Sam Glover: Very cool. So we’re going to take two quick minutes from our sponsors, and when we come back, I want to start talking about some of the tools that you’ve eluded to.
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Sam Glover: 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. If you want to be a better human being on the phone, give Ruby a try. Go to to sign up, and Ruby will waive the 95 dollar set up fee. If you aren’t happy with Ruby for any reason, you can get your money back during your first three weeks. I’m pretty sure you’ll stick around, but since there is no risk, you might as well try. And 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 in 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 Floyd: Well, 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 PC in my office. Though, as someone who does estate planning, as you might imagine, a lot of that software is still pretty proprietary PC based. So although I do have a Mac mini in my office that’s my primary work station, 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 Glover: What’s that software?
Katie Floyd: It’s called Lawgic, L-A-W-G-I-C.
Sam Glover: Okay.
Katie Floyd: And 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 pick 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 Glover: And so I heard you mention QuickBooks earlier. You’re paperless, and I imagine that means a Scan Snap for you?
Katie Floyd: Yes. So 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 taxed 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.” And she told me that I needed to to QuickBooks online and that was so that she could have access and I could have 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 implementation, 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 dollar 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 in sending invoices out to my clients. And then they could 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 set up Law Pay, 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 are money that’s not earned for me. And so that’s one of the ways that … Because billing is huge. Billing is one of the biggest paper generators in law offices, and that’s one of the ways time I’m able to keep my billing completely paperless.
But for the other stuff, yes, you’re right. I do have a Scan Snap. A Fujitsu Scan Snap IX500. I have actually two 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 PDFs 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 anytime 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 its absolutely required for their matter, and that after so many days, after they’re matter’s closed, that after I’ve made an attempt to return them that I can discard them and those types of things.
Sam Glover: That’s a smart thing to do. I did that in my retainers as well. It’s funny, I have a Scan Snap 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 paper. When I had a practice, I used 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 council, 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, three four 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 Scan Bot on my phone is all I need, which is pretty much all I use now.
Katie Floyd: Yeah. I actually use Scanner Pro on my phone.
Sam Glover: Mm-hmm (affirmative), I have that too.
Katie Floyd: Very similar app, and what that will allow you to do is take a picture of a receipt or a document, it will even OCR it, find the edges, turn it into a PDF. I’m sure we’ve all received pictures of documents from clients before, and you’re just going, “Why? Why did you sent 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 Glover: You mentioned file storage briefly. Are you a Dropbox user? Or, do you use something else to sync up client files?
Katie Floyd: 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 ethics opinion on that, which basically they kind of punted a little bit and said you just have to do due diligence. So I am 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 two factor authentication turned on. I’ve got notifications 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 back up, it is storing a copy of your files, so it is kind of a poor man or a poor woman’s back up of some sort.
Sam Glover: Well, and if you turn on the pack rat extension, it really is back up.
Katie Floyd: Archived, yeah. Right. And I’m also … So 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 Back Blaze to back up my documents, both at work and at home. So there’s really … If anything happens, I’m pretty well covered.
Sam Glover: You know my new favorite thing about the Scan Snap actually is with the last update, or the previous to last update, the Scan Snap 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 Floyd: Yeah.
Sam Glover: And then what kind of … It doesn’t sound like you’re using practice management software yet.
Katie Floyd: 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 one 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 episodes on Hazel.
And so I have a lot of Hazel actions invoked 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 six 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 a practice management system for?
Sam Glover: 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 Floyd: And again, you said so much is in email. I’m using a Gmail For Work account, so that’s more that archiving everything that I’m using. I’m also using a third party plug in for Apple Mail called Mail Tags, and I’ve set up 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 V. Jones matter.” So it’s tagging as another factor to help tag my mail.
Sam Glover: You mentioned Hazed real quick. And I want to include links to the episodes of Mac Power Users so that people can go hear some examples of how to use it and what to use it for. But can you give us a couple 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 Floyd: Well, and 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’ve scanned everything in with your fancy Scan Snap 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 files. Hazel has the ability to now read the data in like PDF files, and of course, lawyers work and live and breath in PDFs.
So you can set up specific Hazel rules based on criteria and files. So here’s a very simple one for just 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 Receptionists 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 this 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. So 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 set up 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 Glover: 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 would be so easy to just grab something like that and have it make it happen automatically. So 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, whether or not, honestly, whether or not they have to do with your law practice?
Katie Floyd: Well, I’ll try to give you things that are more productivity focused. A couple of things, obviously all 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 iOS. One of the things that I like about it is in 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 dictations. So it’s just probably one of the best calendaring applications that I’ve used. So it’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 in my estate planning practice is a password manager app. My personal preference is one called One Password. I think Last Pass is probably pretty 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 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 passwords across all of your sites. And its a real pain to do that unless you’re using a password manager.
So just to have that information stored somewhere else, what One Password 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 your even just your email and those types of things? So I typically tell them as part of a comprehensive estate 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 Glover: So how do … 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 Dash Lane. I use Dash Lane. She knows that. We hae a shared password. Dash Lane also has a dead man’s switch, which is nice. If I don’t use it for two weeks, it will 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 Floyd: 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, what 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 do, and what I think might be right for certain people, is I’m comfortable, I keep all of my stuff in one password. 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. So it’s just kind of a … And I think it also has, “And if this makes no sense to you, and if you need help, here’s the name of two of my techy friends who can help you walk you through this.”
Sam Glover: That is super smart. I’m going to include that link. Any other must have apps?
Katie Floyd: Oh, I’ve got a ton of must have apps.
Sam Glover: I’m sure you have a long list. Give me two or three more.
Katie Floyd: Give you two or three [nore 00:42:58]. 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 Allan 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, ten years from now. One of the things I noticed is ten years ago, I put a note in here to renew my passport, and it’s just come up due, so it’s interesting that I’m using the same GTD application now that I was using ten years ago. So it works.
Sam Glover: That’s amazing. And 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 Floyd: well, and that’s some of what I’ve done too because it’s great for calendaring, it’s great for follow up, it’s great for making sure that you can note your deadlines. So there’s that. The other thing, and mine is pretty unique, I use a product called [Zultis 00:44:03] and MXIE. But I think having a basic VOIP phone solution is a good solution. And find the one obviously that works best for you. Some people like Ring Central. Some people like Vonage. I went with mine because basically, a long time business associate and client of mine happens to run a telecommunications company, and it worked out well for me. But having the ability to make and return calls from anywhere, you know 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 from 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 Glover: And so you have a separate business phone number, and that’s what you use that for?
Katie Floyd: 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 VOIP 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 phone. And I think Ruby can do this to some degree as well. I 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 two weeks off in April.
My family and I are going to Amsterdam and Holland and Belgium for two weeks to go see the tulips. So I’m still going to have to do some work. I can’t take completely two 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 Glover: 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 Floyd: 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, I mean, 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 was kind of 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 end up taking it, so why don’t I just not take it to begin with?”
Sam Glover: One of my favorite posts on our site is, “The clients you don’t take will be the best money you never made.”
Katie Floyd: Exactly. And that’s absolutely true. I think one of the best pieces advice that a judge gave me once is, “The best decision you’ll ever make is to fire a client.”
Sam Glover: Mm-hmm (affirmative), totally.
Katie Floyd: So I think going slow and kind of coming at this from hopefully a position of strength, and I think it’s at least what gives me some comfort in this solo journey.
Sam Glover: Well, for what it’s worth, from somebody who had been there and done that, I think you’ve got the right approach. I really appreciate you being with us and talking about your practice while it’s still in its birthing phase, I guess. It feels like it’s in the process of becoming, and it’s really cool to get a window into how that’s happening. So thank you so much for being with us today.
Katie Floyd: It’s been my pleasure.
Aaron Street: Make sure to catch next week’s episode of The Lawyerist podcast. If you’d like more information about today’s show, please visit, or You can subscribe via iTunes or anywhere podcasts are found. Both Lawyerist and the Legal Talk Network can be found on Twitter, Facebook, and LinkedIn. And you can download the free app from Legal Talk Network in Google Play or iTunes.
Sam Glover: The views expressed by the participants of this program are their own and do not represent the views of, nor are they endorsed by Legal Talk Network. Nothing said during this podcast is legal advice.


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Episode Details
Published: July 12, 2017
Podcast: Lawyerist Podcast
Category: Legal Technology
Lawyerist Podcast
Lawyerist Podcast

The Lawyerist Podcast is a weekly show about lawyering and law practice hosted by Sam Glover and Aaron Street.

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