
In this episode of High Velocity Radio, Lee Kantor interviews Michael Woolf of Boon Legal. Michael shares his journey from technology, video game development, and entrepreneurship to building a law firm designed specifically for entrepreneurs. He discusses the limitations of traditional legal services, the impact of AI on the legal industry, and how relationship-driven, flat-fee legal support can help business owners navigate growth with greater confidence and clarity.
Michael Woolf is a former video game developer and filmmaker who became a corporate attorney, business advisor, and entrepreneur to help build a world where businesses uplift the people they touch.
For more than 25 years, he has worked at the intersection of business, leadership, technology, and law, guided by a conviction that companies thrive when they put human dignity at their core. He helps organizations scale by aligning their systems to serve their people’s highest aspirations.
Early in his career, Michael learned that the stories people tell and the way they treat one another define the experiences they create. As he transitioned from working in entertainment to guiding executives through mergers, acquisitions, and governance challenges, those lessons became foundational.
He discovered that when a company stalls, it is rarely because of poor strategy or a lack of talent—it is often because trust has eroded, culture has been neglected, or operations have drifted away from their purpose.
Today, he helps entrepreneurs identify and overcome those invisible barriers, rebuilding the foundations of trust and collaboration. His practice is dedicated to helping emerging and growth-stage companies remove hidden friction and reconnect with the values that inspired them.
While clients may initially seek legal counsel, they stay because he and his team help co-create systems that allow people to flourish. Whether negotiating an acquisition, mediating a conflict, or drafting a contract, Michael focuses on protecting innovation, empowering teams, and amplifying the positive impact his clients strive to make. He is committed to fostering cultures of empathy, accountability, and sustainable growth.
Beyond his professional work, Michael explores the art of craftsmanship through sculpting, storytelling, and cooking meals for friends and family. Each pursuit serves as an opportunity to gather, listen, and connect, reinforcing his belief that meaningful relationships are built through generosity and attention to detail.
He draws inspiration from purpose-driven leaders such as Simon Sinek, team-building experts like Patrick Lencioni, and negotiation specialists such as Chris Voss. Alongside his wife and children, Michael measures success by the growth and impact he helps others achieve.
As he continues to expand his firm and mentor the next generation of entrepreneurs and attorneys, his ultimate goal is to leave a legacy defined not by personal achievements, but by the communities and leaders empowered to thrive because someone cared enough to invest in their success.
What You’ll Learn In This Episode
- Michael Woolf’s journey from entrepreneur and technology leader to founder of a client-focused law firm.
- The challenges entrepreneurs face when navigating traditional legal services.
- How flat-fee legal models create greater transparency and stronger client relationships.
- The importance of aligning legal support with business strategy and long-term growth.
- Lessons learned from the video game industry and their application to entrepreneurship.
- The evolving role of AI in legal services and professional consulting.
- Why value-based outcomes matter more than billable hours.
- The benefits of preventive legal guidance in reducing business risk.
- Building trust, communication, and collaboration between attorneys and business owners.
- Creating a more accessible, relationship-driven approach to legal services for entrepreneurs.
This transcript is machine transcribed by Sonix.
TRANSCRIPT
Intro: Broadcasting live from the Business RadioX Studios in Atlanta, Georgia. It’s time for High Velocity Radio.
Lee Kantor: Lee Kantor here another episode of High Velocity Radio and this is going to be a good one. Today on the show we have Michael Wolff, who is with Boon Legal welcome.
Michael Woolf: Thank you. I appreciate being on the show. Lee.
Lee Kantor: Well, I am excited to learn what you’re up to. Tell us about Boon Legal. How are you serving folks?
Michael Woolf: Well, I appreciate that. Yeah. So we’re a firm of entrepreneurs for entrepreneurs. I actually came into the business a little bit later in life and was in technology and entertainment, making, uh, video games and films for a couple of decades before I went back to school, as I was just trying to learn more about what it is to, to understand the law in the context of a business owner. And I just, I had some experiences along the way, as one does, and found it to be very frustrating to work with attorneys. And the thing that I found as a business owner was that it can be very lonely and very scary often to, to be in that role. So, you know, I basically, uh, go through my days trying to help folks with making entrepreneurship a little bit less lonely, a little bit less scary. And, uh, I practice what we call happy law here.
Lee Kantor: Now, in your, in your background, when you were an entrepreneur and a video game developer, how was your companies interacting with legal in that regard? Was that something that you were excited about when it was time to talk to legal, like, what was your kind of relationship with the law when you were before you were a lawyer?
Michael Woolf: You know, I think it’s.
Michael Woolf: Not much different than most people that have to interact with the attorney. I mean, there’s, as one of my comedy friends would say, you know, comedy works because the jokes point to something that’s real, right? The fact that there’s a lot of of jokes, jokes about lawyers is really indicative of what people expect from them, whether it’s, you know, things about professional courtesy or whatever those other things are that those jokes entail. But they’re there for a reason because it can it can really feel, you know, even when the lawyers on your side, it can very much feel like a us them relationship. And I think a lot of that has to do with just sort of the history of, of the practice, not, not too different than, say, in the medical world where medical schools used to teach doctors, you don’t talk to your patients and get them to tell you what’s wrong. You’re the doctor. You tell them what’s wrong. Well, you know, if your diagnosis consists of not listening for the the you know what Chris Voss would call the black swan information, right? The, the little nuances If you’re not listening for those things, then you’re missing a lot in terms of how we can help support the folks that we work with or how you can, you know, I mean, just even my wife will will remind me plenty, you know, stop talking and listening.
Michael Woolf: Maybe you’ll understand what I’m saying. So yeah, so part part of that is, is, you know, feeling heard by attorneys can often be difficult. In fact, the number one thing that came out in the last couple of years, uh, reports on things like malpractice. The number one thing, um, I think is both the plurality and the majority. I think it’s well over 50% of cases of malpractice really stem around just poor communication. So I think one of the things that we try to fix really early on is that moment of, of, uh, all I can call it is, is, is really like scarcity type fear, you know, how much is this thing going to cost? Right? That’s, that’s often the very first reaction on most people when it comes to dealing with lawyers, but professional services in general. Um, so what we do is, is we, we take a balance, uh, and look at the risk and say, well, I don’t know that it’s going to give me that much trouble if it’s not exactly right. But that’s a terrible, terrible way to go into making decisions about your business.
Lee Kantor: Now, when what was kind of the impetus to say, okay, you know what? I want to learn the law and I want to, um, be able to serve businesses from a legal standpoint as well.
Michael Woolf: Well, one of the things that came up years ago, and I wasn’t at that point in an executive position, but I was close to the C-suite and I was working, uh, I was working for a small company at the time. You know, you had the owner of the company, you had really one, 1 or 2 people that were, uh, sort of sitting just underneath them. But we had, uh, a project that we were doing and at the time, um, the, the typical contract for the kind of work we were doing, which was something that we, we owned the IP for, and we’re just looking for a production deal and a distribution deal with, with a publishing company. So my understanding was, was very simply that it was a two, a two, uh, product deal. Well, we did the first product and those contracts at the time generally ran that, um, it was usually about a million and a half dollars just to press the disks, uh, for like say a video game to put them on the shelf. Um, then you had the price of at the time, about a half $1 million for the actual development of it. So there’s 2 million there. And, and the way that the contracts essentially run was all the revenue coming in to cover the cost of goods, that $2 million price tag that that came off the top and went back to the distributor publisher. Then they had, uh, essentially like a 4RX, uh, sorry, a four x ROI on the, uh, on the investment.
Michael Woolf: So that’s an $8 million thing. And so from the point after that first amount was returned and now their costs are paid for, then it would turn to an 80/20 split where they get 80% up to that first ROI, and then it would switch and 20% to the developer, 80 or 80% to developer, 20% of the publisher after. So once you get that first, you know, $8 million or so done. Um, great. So at the time we did a half million dollar distribution or distribution production deal. Um, that left that 8 million return. And when the season came around that product in the first 18 months or so, made somewhere between 53 to 56 million is what was reported. Um, give or take. So that means that that company and at the time company of, you know, a dozen or a few more people, um, should have been making some pretty good royalties on that. Uh, to give you a comparison, if you remember the, the original deer Hunter game, you know, Christmas bonuses for the deer Hunter game for that small team of about the same size were BMW for that year. So we’re talking about a good bit of money when you’re, when you’re talking about 45, $50 million going back to the company and, uh, and we get a big fat zero. And my understanding was the reason that we got that big fat zero was because one line was missing out of the contract.
Michael Woolf: And I found myself about 12, 14 months later at one of our competitors doing it directly competitive title to what we were doing at the time. I went to work for them. We put out three titles, uh, in about the next 12, 14 months. And I was offered a partnership and I, I said to my partners at the time, and, and this was such a big deal that reverberated across the industry. Everybody knew what happened, uh, at least to some amount of detail. And they said, listen, we, we want to make you a partner. And I said, first, thank you so much. I appreciate the vote of confidence. And I’m really honored. Uh, but there is no way in hell I’m doing this unless one of the three of us gets some legal education, because at that point, we had doubled our team size. We had about 70 people in house. We were dealing with another hundred and some odd people out of house with, uh, outsourcing and so forth on a, on a massive project. And I said, you know, we’ve got 70 families relying on us to do our jobs, right? And we can’t let what just happened at my last company happen here. And they said, absolutely, 100%, we agree with you and go for it. Uh, so, so that’s how I eventually ended up back in law school. But I never intended to practice law. I intended to go back to what I was doing.
Lee Kantor: Right. So you went to just understand more and have an impact, have more of a say in understanding of how to not get screwed again.
Michael Woolf: Yeah.
Michael Woolf: I mean, and, and if you think about the timing of it, that that whole thing went down roughly around, um, probably Q3 of 28 of 2008 rather. So we’re talking about just before Lehman Brothers collapsed, right? So that slowed down that whole partnership conversation, obviously, but we ended up floating that company for the next two years, uh, as the world fell apart, um, doing our best just to hold on to our crew and make sure people were taken care of. And like I said, try to understand that the job we do doesn’t affect individuals, it affects families. And we took that pretty seriously. Um, and the three of us who were the partners in that, uh, you know, we took the biggest hit. But as the saying goes, that’s because leaders eat last. And we understand our job is to, you know, as Simon Sinek would say, is not not to be in charge, but to take care of the people in your charge. And we take that real seriously.
Lee Kantor: And then how does that translate to boon legal? Like what type of services? Like, how are you doing kind of legal differently for the entrepreneur?
Michael Woolf: Well, I was at a, you know, it goes back to I finished law school and I was recruited by a giant law firm. And at the time, I think there were 1000 lawyers or something around the country. Uh, so we’re talking about a good sized firm. Uh, it’s, it’s a big ship a hundred years or more old. That takes a lot of momentum to, to change the course of stuff. And what I found there was that the, the classic big law stories you hear of. Uh, not only are they generally true, um, but it was more problematic. It was more frustrating for me as a, as a provider of services than I ever was as a consumer because it felt so hand tied by the system that was, uh, we were all operating on. And what I found is that, um, that we weren’t able to be responsive because it was such a slow thing. I don’t want to say that, uh, lawyers are all Luddites. They’re not all Luddites, but. But there’s certainly a good number of them out there that, you know, have trouble. I mean, there were literally, you know, some of the older attorneys of that firm who’s who’s assistants would literally print out their emails every morning, and they would mark up responses on paper and hand it back to have email sent back out. Like, I mean, we’re talking about some, fairly arcane stuff there. So, uh, one of the things I noticed is, you know, the basic movement to become a lawyer is undergrad, law school, internship and practice.
Michael Woolf: And along the entire, uh, usually six ish, seven years of that whole process, all these folks are being told is the only thing that matters is how many hours you build. Right. Um, but we are whether people want to realize it or not, we are in a post billable hour world. Um, there are very few things you can still truly do that with, and I think most of them have to do really with manual labor because you need somebody to physically be out there. So, uh, a material labor contract with a, you know, a company that’s out doing long service or tree removals or whatever those things are, that that’s a fine use for it. But in professional services, It’s a cop out and it hurts everybody along the way. And that was something I discovered when I started my first company back in college, when I just thought I was doing, you know, some freelance on the side and didn’t realize I started a company because I was just so naive about it. Uh, but I did two jobs in the early mid 90s. I did two jobs, uh, on an hourly basis. And I swore I am never doing this again. And I didn’t until, you know, 30 years later, 20 years later, whatever it was that I ended up starting to practice law and I came back to the same thing. This is dumb. Um, and, and so I was thinking about the practice, not from the point of view of the provider in this case, but really put my entrepreneur hat back on and going, you know, if, if there are so many people who are pushing against this thing, we have 80% of both individuals and businesses in this country who don’t have any representation.
Michael Woolf: And then it turns out if you’re if you’re a business, you can’t even represent the business unless it’s a sole proprietorship. You know, you’re not allowed to represent your own business the way you’re allowed to represent yourself. So it becomes a real, real problem there. Uh, and what I realized was I want to fix from the provider side because I didn’t want to do it. I want to fix the inability to communicate deeply with a client and build a relationship. Because when you charge people for every six minutes of your time, they sit there and they look at their clock and go, I really don’t care about your kids, Bill. Let’s get on my thing, you know? And, and so it’s, uh, it’s a problem when you are trying to protect somebody and think about how to protect their business. If you don’t know the nuances of the business, if you haven’t spent the time to really try to understand as best you can what their day to day looks like, what their sales cycle looks like, what their tech looks like, and really dig into it for the black swans to find out how to truly protect them. I think that there’s an incredible disservice. So from my point of view, it was first things first, get rid of communication barriers, which is where we started.
Michael Woolf: No hourly billing model. Everything’s on a flat fee. And guess what? I thought about it real simply. I would do business with people the way that I want to be treated. It’s the old golden rule. So, you know, most people are fine paying for a service or a good, so long as they know what the cost is up front, they’ve agreed to it. Well, that doesn’t happen in legal usually. Um, and again, it’s a professional services issue, not just legal issue, but there’s people out there that get so frustrated because you’re like, what did you build this for? What did you build that for? What did you build the other thing for? And that’s why, you know, across the country, uh, the realization of how much a law firm gets in for every dollar that they spend is only $0.61. And that’s, that’s the average across the country. So, um, you know, our realization rate is almost 90 because everybody’s agreed to what the cost is on the front end. We don’t, we, I’ve never had in nine plus years now of practice, uh, through being legal. I’ve never had a single client that’s come back to me to go, hey, I need to go through this, uh, this invoice with you or this this billing. Not once has that happened because we just eliminated that barrier. And then we went through and started eliminating as many others as we could as well.
Lee Kantor: Yeah. I never understood why professional services likes to charge hourly because it’s so counterintuitive because the better you are at your job, the less time it should take. Like it? It never made any sense to me that like, in some ways, you get penalized by hourly because if you can do the job in ten minutes. Then why are you. Why should that be only a fraction of your hourly rate? Like focus on the value or the outcome you’re delivering, not the time it takes to deliver the outcome.
Michael Woolf: You are absolutely correct. 100% agree with you on that. And the answer, by the way, because I’ve asked the folks at the big firms. Um, I’ve got, I’ve got a friend mentor at a firm, uh, we were talking about AI, for example, and how they’re starting to use it. And this is another national firm, and they have a team of 50 people that are trying to crack the nut on how do we build if we’re not billing by time, like literally 50 people sitting around trying to figure that out? I’m like, why? Why is this hard, guys? Um, it you’re right. It is counterintuitive. And, and that’s what’s giving, frankly, a lot of the frustration in the industry, specifically from, uh, from business clients. And you’re seeing that across the industry now where business clients are leaving their long relationship firms that they’ve been with, particularly the big firms, they’re leaving them, they’re poaching the guy that’s been helping them from that firm, and they can pay that same person it easily. What they’re making is a base plus plus bonuses at the firm, uh, at a big firm, they can pay them that plus, you know, plus plus and stock options and all the rest of this stuff.
Michael Woolf: And then hire another 2 or 3 people underneath them for the same cost. So these folks are, you know, generally speaking, they’re looking at the bottom line going, this is a this is a cost sink. It doesn’t appear to provide an ROI. And, and the number one answer I’m getting from these folks is we don’t know how to charge people for it. And I thought, well, that’s the dumbest thing I’ve ever heard. And the reason it’s the dumbest thing I ever heard is this. It doesn’t take much to go, Okay. If if it generally takes me three days to do this task, but two, you know, 3 to 5 year associates, or I can use this piece of software over here and do the same thing with better results in, you know, 3.5 hours with one person, then I can take that other person and let them do, you know, a whole bunch of other work that they can be billing for? And if I only build half of what I would normally bill for that, because we’re doing it on a value based thing, then who cares? I can make money hand over fist with that.
Lee Kantor: Yeah, and.
Michael Woolf: It’s not a money issue. It’s it’s a creativity issue, I think.
Lee Kantor: Right. Well, and it’s this a lot of like you mentioned, these older folks that are in charge have a lot of, you know, kind of history and the way we do things and the way I get compensated and they don’t want to change because it’ll mess them up financially. I mean, it becomes impossible to Defend to defend the. What AI can do. Ai should be, you know, causing the the legal fees to drop dramatically just because of the speed of what it can do. I mean, how how could the implementation of AI in legal end up costing you more? That seems impossible.
Michael Woolf: Well, I’ll tell you. Uh, if I if I have to guess, it probably looks something like either, uh, well, first of all, you’ve got now I think we’re up to four, maybe five generations of attorney that have gone through this. All that matters is what you think and understand. And I and I have this from, uh, one of my professors in, in, in law school, uh, Michael is, you know, had his own firm for many, many years, was very successful with it, became a mediator. He’s very successful with that business. And he, you know, he was teaching the the I think they called it law. Law office management or something like that. It’s your basic sort of, uh, 12 to 16 week mini MBA incubator kind of class and first day of class. He comes in and on the board, he writes the three things. He writes teachers, clergy, lawyers, right. He says these are the three worst types of business people ever, but not in that order. Right. And and, you know, I say that and everybody says, oh, yeah, well, don’t forget about doctors and don’t forget about this. And don’t forget about that. That’s all true. But understand that, uh, you typically never learn how to run a business. Think about it. These, you know, the, the system that we’ve set up over the last, like I said, about 130, 140 years now has been essentially, uh, you know, uh, pyramid level marketing, uh, you know, it’s Amway with a bigger degree on the wall.
Michael Woolf: You know, better certificate or something. And and unfortunately, that’s a it’s just a terrible business. And on top of it, it it’s generally thought I mean, we pretty much outlawed it in this country because it’s essentially a scam. It doesn’t mean that it has to be, but it’s a pretty easy way to go about it. But the average partner in a law firm today, they’re not doing, you know, eight hours of billable work. They’re doing two, two and a half, I think is the, the right in that range. So even even the big partners aren’t actually doing the billable work. So what are they doing? They’re spending a couple hours reviewing stuff that the underlings or the associates are doing, and the rest of the time they’re selling their salespeople, their, uh, raising the profile in the community. They’re dealing with their charitable things that they can get their names out there and, and all the things that everybody in business does, except they don’t know that they’re doing business work. And so I’m not sure how you change this idea that, um. Oh, well, we have a business model, but hourly billing isn’t one.
Michael Woolf: So when it comes to I’ll give you one example. I was at the big firm and because of my background in technology, they asked me to come in and do a bunch of tech evals for at the time, it was machine learning tools and they had a machine learning tool, uh, that was dealing with due diligence, uh, due diligence work where you have to go through a bunch of contracts and ensure that all these contracts, um, in a, in a merger acquisition deal, these contracts can be transferred and assigned over to the buyer. And so you got to go through them. Now, it took me and one of my partners, uh, over there, one of my, uh, I say partners, one of the associates that was above me, he was, uh, I think 3 or 4 years in on the year, year and a half in and we go through this thing. It takes us three and a half days for the two of us to go through this thing of contracts and you’re literally making an Excel spreadsheet of going, okay, here’s where all these things are that we need within each contract so it can easily found. And here’s what the limitations are, so we can make sure we get these transferred correctly and so forth.
Michael Woolf: I use the machine learning tool when I was doing my eval with the exact same project, because I had a control on it. Right. And we didn’t know before we started that we were competing with the computer. So what, what we did in three and a half days, I could do on the computer, and it took me under three hours to do it and it found stuff we missed. So a couple a couple weeks later, the firm had gone out and licensed the thing, and they paid an enormous amount of money for it for a firm of of 1000 attorneys. We did a thing where the one of the heads of the business department called up, uh, and did a all hands for the business group. And so there were 14, 15 attorneys in, I think, 2 or 3 offices on this call. And they said, all right, we’ve got 15,000 documents that we have to run through for this thing that came up. It’s a last minute thing. We need it in two days or whatever it was. And they said we got 15,000 documents, and all we need to do is put them into one of two categories based on one of these two forms that we start with. And they took 14 attorneys, uh, of all levels from partner down and put them on this.
Michael Woolf: And it took a day and a half or so to go through them all. Well, as soon as they had this conversation, I walked into my, uh, supervising attorney’s office on that. And I was like, hey, um, didn’t we just license this machine learning thing over here that is specifically designed to do this work? And he goes, yeah, you know, we did. And so he picks up the phone and he. Aha. Aha. Yeah. Didn’t we get this thing blah blah blah. And he hangs up and just shakes his head. And I said what did they say. They said, yeah, we have it. We got the license and we’re not allowed to use it. And I said, well, why, pray tell, are we not allowed to use it? And he says, well, they haven’t figured out how to charge for it yet. And I about blew my mind. I was like, are you kidding me? You’re gonna stop 14 attorneys who are doing billable hours for almost two days to work on something this thing can do in a couple hours because you don’t have to charge for it. Let’s see. Let’s take the amount of hourly billing per hour times 12 hours times 14 people. Divide it by half. That’s a good charge, isn’t it?
Lee Kantor: Well, they didn’t want it. That’s the problem. They didn’t want to discount it. They wanted to make as much, if not more. That’s the problem. They don’t care about the customer. They’re not thinking of what a great deal. We just are going to save this customer. All this money they’re thinking of, how do I not lose money based on how I used to do this? That’s their thinking. And that’s the problem. And I think.
Michael Woolf: And I had that conversation, Lee, I had that conversation with our on my exit interview with the chief strategy officer, and I’m sitting there in his office going, I’m using this example and going, this is the dumbest thing. And he said the same thing. Oh, they don’t have charge for it. And I said, this is not hard, right? You got a firm here that’s got 100 plus years of information, data to, to, to look through. You cannot tell me that. We don’t know exactly how long the average and median is of every damn thing we do.
Lee Kantor: They do, but they don’t care. No they don’t. They can’t make more money from it. They can only make less.
Michael Woolf: And that’s the mistake. Because what I said, what I said back to him is we’ll take that same example, right? You got 14 attorneys. You can charge anywhere from a quarter to a third to a half of the hourly billing you would have otherwise lost if they did it by hand. And nobody’s going to blink about it, right? But think about this. If you do that and one attorney is busy for a few hours working with the tool, what if you did that 14 times? Don’t tell me you can’t make more money, right? That that whole idea of, oh, we can’t figure out how to make money with it is, is not a fallacy of the tool. It’s a fallacy of the imagination and the ability to think like an entrepreneur.
Lee Kantor: Right? And 100%, I 100% agree. But in the in the model that they see law is how you described it earlier. Law is only two hours of billable hours. That’s their definition of a day.
Michael Woolf: That’s how they’re doing it now.
Lee Kantor: Right. But now you’re saying charge, use technology so you can have more billable hours. They’re looking at.
Michael Woolf: No no no no no. I’m not I’m not saying that at all actually. I’m not saying to to. Let me let me let me make it a little bit easier because it is a confusing idea. Right. And it seems to be a counterintuitive, confusing idea at that. So what I mean is this in. Let let’s take a let let let’s take the example of just a regular everyday attorney. Okay. A regular everyday attorney in most in most practices, they’re averaging roughly 1800 to 20, 1800 to 2000 billable hour requirements per year. Okay. Now, if you if we’ll take the 2000 hour requirement because it’s an easy one, easy math, 2000 hours is determined by 50 working weeks, two weeks of vacation in this country. So 50 working weeks times 40 hours a week gives you 2000. So if I divide that up, we’re looking at functionally a 40 hour workweek, but it’s not a 40 hour workweek. It’s a 40 hour billable week. 40 hour billable week is what, eight hours a day for five days? Except if you think about this from again, you use the mindset of an entrepreneur who understands the basics of if they’re not even an expert, they certainly understand the basics of project management. I don’t have eight hours in a day that I can devote only to this. Why? Because other stuff creeps in all the time. The phone call to somebody who needs some advice.
Michael Woolf: The problem that you have to fix, whatever the thing. Oh, hey, go to the bathroom, fixing the lunch, taking out a client, etc.. Oh, you got to stop and go to your kids play at school. That’s important, you know? So what happens is we break it down. We say that’s eight hours. But when they’re not accounting for it is it takes roughly 1.35 hours to do an hour’s worth of work because of all those interruptions. So now we’re looking at not an eight hour day, but a 10.8 hour day. That’s essentially 11 hours of work to get those eight in. Well, that’s a 55 hour working week. So now, now that’s if you’re fully stacked up and you don’t have to do any sales, you don’t have to do any relationships. You don’t have to meet with a client that’s just straight workhorse. That doesn’t happen. So that’s how you get to I got to work 60, 70, 80 hours a week as an attorney. And what they’re trying to do because they don’t know any different is they’re trying to figure out, well, gee, if I’m only really working 2 or 3 hours a day because I’m not doing all this work, I got to charge whatever the hundreds of dollars per hour because I expect to make this living at the end of the at the end of each month, and in order to make that living, I get to do so many hours at so many costs and all the rest of it.
Michael Woolf: That’s how I could set a hand. But where the fallacy is, is that they are looking at just the same way that we did with the wheel and the printing press and whatever, you know, television or any other technology that we’ve used is you don’t know what it is. So what is our first instinct as human being is to fear it. But I like a, you know, word processing. Word processing did not get rid of secretaries. Right. Lotus one, two, three back in the day. And WordPerfect, for those of you who are old enough to remember that those did not put secretaries out of business. Okay, the technology is not it’s neither the problem or the thing to fear. All it is is another pencil. It’s a new pencil. That’s it. So the trick is to stop looking at trying to fill your, your your funnel with ours and take the thinking away from the dollars, because I’ll tell you that back in my in my back in my game days, I started a thing. You may have seen it a few years ago where all of a sudden there were all of these, uh, video games for the game consoles around poker, right about the same time. Online poker was a thing. World Poker Tour was coming out. And, and one of the companies I worked for, I worked with a guy named Martin.
Michael Woolf: The two of us sort of developed an engineer and designed what became six, seven, eight years of, of just these poker games for consoles. Um, so I worked in that world for a while. And I remember back in, in 2000, uh, I think for 2005, something like that when Chris Moneymaker won the World Series of Poker, the big thing here in Tennessee, because it was just, you know, a guy, a local guy from rural Tennessee. And the next year it was a lawyer by the name of Greg Raymer. They called him the Fossil Man, that one. And I had the opportunity to sit with Greg one time and we were talking about poker and law. Right. And he, he always brought stuff back to the same place, which is you gotta stop worrying about getting the results because too many people. And, uh, this is really in all areas. I think it’s pretty universal. But people sit there focused so much on the result and the result is irrelevant, right? The only thing to focus on is making good decisions and having a process and learning to love the process, learning to love the craft of the work, not the result of the work, because the results of the work don’t belong to us. Uh, and that’s whether it’s a poker game or legal or doing art for a living.
Michael Woolf: It’s all the same stuff. I said the same thing to my artists over the years is, you know, art is what you do at home. But but what we do here is in industry, it’s the, you know, film industry, the game industry, the, you know, commercial design, commercial arts, etc., that you have to separate the two pieces because we never own the finished product. Our customers do. So it’s not about that. It’s about finding the joy and the purpose of the work and finding the joy in the, in the, um, like I said, in the, the process of doing the work, these are the places we can find the joy. And if you’re looking at it from that point of view, all of a sudden you’re focusing on not, oh, I know how to do this because I’ll tell you, here’s dirty little secret. I’ve never known how to do anything I’ve done professionally, but that’s never been my job. My, my job is not to know how to do the thing. My job is to know how to figure out how to do the thing. Right. So where’s the value in it is it’s not in the hours you spend, it’s in the results that you get for your clients. And I don’t care whether that’s an art client, a video game client, a film client, it doesn’t really matter to me. Does that make some sense?
Lee Kantor: I mean, I’m with you 100%. I mean, I’m a big believer in, um, what is the outcome you desire? You have to have something you’re aiming at that you want, but focusing on the process and the systems, uh, not the outcome anymore. Once you kind of know where you’re headed, that’s directionally correct. I think is okay for most things.
Michael Woolf: Right, right. You’re absolutely right. And guess what? Here’s the thing. Uh, directionally correct is a fun one. I like that because, you know, look, I can get from I live in Nashville, right? I can get from Nashville to Saint Louis in hundreds of different ways. Um, couple easy ones come to mind. I could take a plane. I could drive my car. Okay, great. But guess what? Every single one of those ways we’ve all encountered detours doesn’t mean we’re not going to get Saint Louis in the end, right? But but guess what? You better know you’re going to Saint Louis or you will never get there.
Lee Kantor: Exactly. You got to get that part right. And then, uh, and then once you have a system or a process in place, make sure that you’re paying attention, that it’s still serving you. Because sometimes people latch on to a system or process that used to be a great system or process, but isn’t serving them anymore.
Michael Woolf: Absolutely. And I think that, I think that if you look at professional services as a whole, and I don’t mean just the legal side, I mean accounting, it’s, it’s, uh, medicine, it’s um, uh, the finance, all, all of these big areas. The biggest problems we’re seeing, uh, really have very little to do with the actual work. Everybody knows how to do that, but we’re all struggling with today is what is the best way to get a result that is in the interest of the folks for whom we serve, that is also efficient, both financially but also time wise, because both things matter and we have to do it in a way that balances the benefit for everybody involved. And you’re not going to do that when all you’re thinking about is, oh, well, I gotta, I gotta hit that six minutes, right? And it becomes so toxic. Right? I know, I know off the top of my head, I know six people who I know because I haven’t actually watched them in the room, but I’ve watched them leave the room and we’ve talked about it. I know at least six people right now. Off the top, I can think of who literally will take case files to the bathroom with them so they can highlight and mark up documents because they don’t want to lose the time.
Michael Woolf: Now, that is a sickness, right? That is not mentally well, right. But that’s that’s where we’re putting these people. And then you wonder why, you know, pick your favorite, uh, your lawyers and a whole joke because they’re stressed beyond belief. And then on top of it, and this happens, whether it’s medicine, dentistry, legal, what have you, uh, air traffic controllers, the more your work affects the lives or livelihoods of people, the higher the stress level because we can’t help, as you know, hopefully empathetic human beings, we can’t help but to consider what that impact is. So it’s no wonder that we have enormously high rates of substance abuse, of divorce, of, of mental health issues, uh, you know, heart attacks and so on and so forth. In fields like law, like medicine, like, you know, pick, pick your high stress job. And the stress of it is if I screw up, not only are you going to come after me, right? Which is what we have our malpractice insurance and stuff for. But not only am I in trouble, my partners become in trouble. My business becomes in trouble, and your life and livelihood are in trouble. So that becomes a lot of stress on top of you’re not getting sleep. You don’t have a family life. You can’t whatever. It’s enormously, enormously toxic.
Lee Kantor: And that’s why you’re trying to do things differently. I mean, that’s why, I mean, that’s why Boon Legal exists, because there is a better way and a different way of doing things. Before we wrap, can you share a little bit about maybe a story that illustrates, Somebody working with you. What does that look like? What what do they come to you with and how do you help them get to a different level?
Michael Woolf: Well, that’s a great question. Appreciate it. It’s, um, I’ll say two things. Number one, very few people go to a doctor, lawyer, mechanic, what have you people that fix things. Very rarely do you go to one of them preventatively in this country. It’s just not it’s not what we’re used to. We don’t have universal, uh, or socialized or open medical services. So people don’t even understand the idea of just going for preventative care. Um, but preventative care is great because the more you do maintenance and preventative care, the fewer big problems that you have that you’re not going to know about. So generally speaking, when we see folks come and talk to us, we’re starting from, oh my gosh, I’ve got this dumpster fire that I need to put out and also clean up the mess up. So I joke with all of, uh, all of the folks that I talked to that come in to talk to us and say, if we do our job right, our goal is to go from being part of your janitorial staff, cleaning up your mess to part of your strategy team, where we can prevent them. And so that’s the biggest differentiating factor is our goal is, is literally, and I say this every week in our weekly meetings and probably multiple times throughout the week, I don’t care about transactions as a business person. I’m not interested in it. You know, put me in the lencioni category. What I’m interested in doing is building relationships because again, good decisions get good results, um, Going for good results begets, uh, what’s, you know, referred to as ethical slide, you know, vis a vis, you know, Wells Fargo’s mortgage account showing that they had a couple of years ago where people just started opening accounts for people because, oh, we gotta hit those metrics, hit those metrics, right?
Lee Kantor: Because the incentives were such that that made sense, you know, to the workers where it didn’t make sense.
Michael Woolf: No, it wasn’t even the workers that they found out. It was the, it was the, it was the middle managers that were being pressured for it.
Lee Kantor: Right. Well, I mean, the people who employed there’s a layer of people employed in the organization where they figured out, hey, this is my cheat code, uh, to big bonuses.
Michael Woolf: And it’s, it’s, it’s, it’s going for that, uh, you know, Enron wasn’t very similar. A lot of, a lot of these scandals are very similar. People are going before the results. Well, don’t worry about the results. Focus on making good decisions. Focus on. We are here to build relationships with folks who. We can help, ideally in taking their business to the place where they want it to go. So I’m very, very focused on trying to understand what is it you do? Show me how you’re doing. Let me, let me open up the hood and look underneath and ask some questions because, you know. It’s, you know, tick, tick tick. I’m a technologist. I’ve built all kinds of different types of, of tech. I understand how to talk tech. So again, my job isn’t to do the technology, but gosh darn it, if I’m sitting there and I’ve got a, a client who has a tech platform that they’re bringing their clients into, you think it might be helpful to understand how that works in order to be able to protect them? I think.
Lee Kantor: So I.
Michael Woolf: Think.
Lee Kantor: More information is probably a good thing, not less, in your world. You know, knowing more is only going to help. It’s not going to hurt.
Michael Woolf: Absolutely, absolutely. So that’s one of the big differentiating factors we try to, uh, I will tell you, we offer, say, monthly plans where people, people, businesses can have an ongoing relationship at a set budget price, right? Budget legal is terrific. And they don’t always use every part of that. In fact, most of them, I would say the vast majority don’t use the full complement of services that they get under one of their monthly plans. And yet every single one of them has said the same thing as, I would never cancel this unless there’s something catastrophic. I will not cancel this. I said, what’s the value for you? Because you don’t use all of the stuff they said. The value is knowing if I need you, I can pick up the phone. I can ask a question. I can stop you. Right then have a conversation. And quite honestly, I spend hours and hours talking to my clients and doing very little with those clients of the quote unquote work product. Well, for them, it’s the other way around. The reason I’m not doing all that work is because I have a friend of mine who has a security business, and he’s getting pushback from his clients going, hey, you know, we really have any incidents. We’re going to cut back on security. And he goes, yeah, you’re not having incidents because.
Lee Kantor: You have security.
Michael Woolf: I’m like, you know, it’s counterintuitive, but maybe. Oh, yeah, well, we’re not having incidents. Maybe, uh, maybe we should stop this thing. Okay. Well that’s not. Right. So so we really want to put ourselves in a position where we’re working with the client and developing the relationship that, quite frankly, especially in the C suite, especially from, you know, individual entrepreneurs, uh, business owners that, that have perhaps multiple businesses even, like I said at the beginning, entrepreneurship is lonely and it’s scary very often. And, and we can walk hand in hand with our clients and, and have a relationship where not only, not only can we walk beside them and they can turn to us as a trusted partner in a way they can’t turn to even their own C-suite, right? Because they’re still inevitably the boss, but they can come to us and we can do this all day long in that friendly way to work through and not through the all right, what about this? What about that? And play devil’s advocate with each other and go through the thought experiments and all the rest of it. And we’re looking at it first as business consultants, but business consultants who happen to understand the law, which is a very unique position, or business consultants who happen to understand how to build tech for technologists who happen to understand the law, and so on and so forth. Right. In the ways that you wouldn’t necessarily think about doing it. And so because of that, we’re able to, and I have many times done this, I’ve, you know, on a day to day business, I’ve ticked off plenty of my own clients because I don’t have a problem telling them the wrong. It’s my job sometimes to do that. I can’t represent you and kiss your ass. Excuse me at the same time. Right. So I don’t ever I don’t ever think about that from the dollar cost point of view. I’m thinking about from the relationship point of view.
Lee Kantor: Right. And when you’re there to really serve a person, then part of the service is telling them the truth. And it may not be what they want to hear. And that’s where I think so many professional service people just are yes people. And they’re just like, yeah, we. Yeah, yeah, yeah, that sounds good. We can do whatever. And it’s like, well, I need you to tell me if I’m an idiot here, if I’m being an idiot, I’m thinking I’m doing the right thing. But if you have some insight, it’s your job to tell me otherwise. It’s kind of malpractice on your part.
Michael Woolf: Yeah. And to that point, I think you’re going to see and I predicted this, you know, five, ten years ago that by 2030, this is my prediction. I don’t know if it’ll happen. Maybe we’ll come back and talk about it then. But I predicted that by 2030 you’re going to see at least one, if not multiple lawsuits involving giant law firms for bilking their customers because they’re not using the tools. Um, you’re already seeing plenty of stuff with with funky billing with large clients, unfortunately, at some firms. But when these clients look at these bills for, you know, 250,000 or $1 million or whatever the numbers are, and then they go, okay, why did you spend three weeks manually going through stuff that you didn’t need to do that way. They’re going to have issues. Um, I mean, it will it will come at some point. Um, and I think it’s sooner than later to be honest. Yeah. But I think that holds true for like, if you’re a practitioner and you’re not looking at these things with an insatiable amount of curiosity, not, not to try to figure out your way around it or to exploit it all the rest of it to go, how does the pencil work? I mean, I went to I went to law school late in life.
Michael Woolf: I graduated in 2016 at the age of 45. Uh, most of my class was under 30. I think the average age was like just at 30. And I would say. I couldn’t give you a direct number because I didn’t pull it. But an unbelievably large number, especially of the younger folks, had no idea how to use word correctly to do legal work. And I’m like, you’re gonna be a lawyer and this is your number one most important tool in terms of, you know, writing stuff. And you don’t know that you can use a table of authorities builder and you don’t have to search every single page by hand. I’m like, what? Are you kidding me? You don’t know how to use styles to be able to make a table of contents. I’m like, this is basic, basic stuff. So when you take a look at that and then you give them something like AI, I don’t expect them to know how to use it, right? They’re just freaking out because they can’t use the tools they have.
Lee Kantor: Right?
Michael Woolf: So part of it, and this is, this is part of one of the things that we’re looking into is we have to look at it. And this is, thank God for my game development experience going, okay, you know, we have this, this, this thing now that we call UX design, right? Ux design is a byproduct of laying off the majority of game designers in the game industry in the recession And then going, well, how the hell am I going to make a living? Because nobody knows what I do. But all game design is is user experience. And I used to, I used to tell the folks in my game design teams like your first job is not fun. Fun is again, that’s the result. We’re not looking to build fun, right? Your first job is you’re a teacher because you have to think about a video game. God of war is the best example of this ever, where you have to teach people hundreds, if not thousands of individual commands on a little controller that has somewhere between 8 and 16 buttons. And somehow you’re teaching them to do thousands of things with these intricate button combinations, and you have to do it without using more than about 10% of your screen space. So that’s a challenge, right? But we’re really good in, in that particular area at teaching people how to do stuff that would have otherwise taken ages to figure out, um, uh, you know, the book flow and I’ll, I’ll dare say, uh, Michaela, Chris and Haley, I think is how you pronounce his name, but it’s a very long Polish name.
Michael Woolf: Uh, but, you know, he wrote this book on the flow state somewhere, you know, where you’re vacillating between anxiety and boredom, and that’s where you learn a lot. Well, we’ve been able to do that in that space. There’s no reason we can’t now as, as, as that has blossomed into this UX design. Well, then let’s teach people how to use stuff by designing things well and not doing this. Go figure out how to make it work, which is always what, 1.0? Um, I mean, we’re maybe what one AI 1.2 at this point, you know, if you had to pick a number, it’s very early on and if you’ll remember stuff like WordPerfect to bold a word and WordPerfect used to be, you know, uh, go up to the top and it was, you know, uh, text style. Bold, right? Well, now there’s a half a dozen or a dozen ways to do it in Microsoft Word. Well, why? I only need the one. Right. But the reason that they’ve built all of the rest, whether it’s the hotkeys or the ribbons or whatever, you know, right click pick, pick your poison for how you want to bold text.
Michael Woolf: But the reason they’ve done it is to try to build intuitively to the way everybody thinks about it, not the way I think about it. Right. And so we’re at that place where we’re dealing with functional design, programmer design. We used to call it back in the day, it is, okay, you can use this to do this, but it’s going to be clunky. You’re going to have to figure it out a little bit. There’s no real documentation yet. That’s 1.02.0. We’re going to start to see, I think is where we’re doing less of the instructing and just getting more of the serving because the AI will get smart enough or smart enough is not the right word. It will It will learn enough from the repetition, right, that this is the way we like to have things done, and it will anticipate that. So I think that’s the next step of it. And then we’ll go beyond that. But right now we’re talking about, you know, uh, I would say the majority of people using these tools are not really using them to anywhere close to forget their full potential. The quarter of the potential of what these things can do, because they’re just trying to replace stuff, they’re trying to do tasking, and it can do that, but that’s not really where it’s going to excel.
Lee Kantor: Yeah, I mean, yeah, I agree. We’re at the beginning of the beginning here. This is um, we’re nowhere. This is not this is the worst it’s ever going to be. So I mean, yeah.
Michael Woolf: And it’s pretty damn good.
Lee Kantor: Yeah. I mean that’s the thing that’s so scary. That’s what frightens people because it is pretty damn good. And it is the worst it’s gonna ever be. So both are true.
Michael Woolf: Um, well, so let me let me give you the short, the short positive, uh, to, to leave folks on regarding that. Remember that Napoleon Hill’s book is called Think and Grow Rich, not work your ass Off and grow.
Lee Kantor: That’s right. Right.
Michael Woolf: It’s the it’s that whole thing about creativity. We just talked about. Right. It this is where and this is where the money making comes from. It’s not from these. And so as long as you are able to change the way you think about stuff, not worrying about who produces the finished written document or the finished, uh, you know, pre-manufactured gizmo or whatever it is you’re doing, right? That is a whole hell of a lot less important, uh, than how are we thinking about why we’re designing this thing? Why are we making the choices we’re making in terms of how somebody interacts with it? Why are we choosing to put this clause or that protection or whatever into, uh, into this deal. Not because we’re supposed to, but because it means something, right? That’s where we’re going to excel. And quite honestly, you know, we’ve been moving. When was the, the what was it the one our manager. When did that thing come? Right.
Lee Kantor: Was it even the one hour? Was it like the eight minute, the eight minute manager. I thought it was minutes.
Michael Woolf: Well I mean it’s it’s it’s it’s it’s vacillated. I think there’s a there’s a minutes, there’s hours. There’s whatever it is, I’m sure somebody will correct me in the comments below, but, uh, the, um, but the point of it is, is, is we’ve been in a position for quite some time where if you’re a business owner who’s truly focused on being a business owner and not employing yourself, different things, then we’re looking to day one, when we start doing whatever it is we’re doing day one, when you start your job is you’re replacing yourself. The number one thing to do, because as soon as I can pay somebody else to do what I’m doing and free up the time, do I need to pay them? Yes. But I first got them a force multiplier, and eventually I got people that they’re going to do the same with, and I can start backing away from my day. And so, you know, my brother, who’s also an attorney, he took a ten day cruise with his family. And I said to him afterwards, expecting an answer, 2 or 3 hours, I said, how many hours a day did you work while you were on the cruise? And he says, oh, it wasn’t bad, 4 or 5 hours. And I’m thinking to myself, you got to be kidding me, right? I mean, like, I don’t think it’s great to have to work two hours while you’re on vacation. It completely defeats the purpose of what that is. But five hours is a that’s a that’s a working day. Minus a couple meetings and traveling from place to place. That’s insanity. Yeah. Whereas I just took six days off and I didn’t even touch my phone to look at emails. Right.
Lee Kantor: I like your system better. I think you’re on a better track.
Michael Woolf: I’m trying. Now, does he make more money than me? And has he for a while? A little bit. Yeah. But guess what? I’d sure rather be sitting in Yosemite as I was and and enjoying myself with my wife. Uh, then. Then sitting there and banging my head over some stuff that’s, to me, meaningless. My clients. It’s extremely important. And I always put that on the top of my mind. But for me, I don’t have a dog in that fight.
Lee Kantor: Right.
Michael Woolf: So I’m happy to take a week and just step away and breathe. It was glorious, right? Glorious. We didn’t have Wi-Fi.
Lee Kantor: That was even better.
Michael Woolf: It was terrific.
Lee Kantor: Well, well, Michael, we got to wrap. I got a if somebody wants to learn more about Boon. Boon Legal. What is the website? What’s the best way to connect with you or somebody on the team? And then this is for people, entrepreneurs of any stage, right. This is for a business owner at any stage of their growth. Uh, if they want a different kind of lawyer, this is the place to go.
Michael Woolf: Well, yes, and I, and so first of all, the, uh, the, the URL is www dot Boon, boonlegal.com. So it’s not like Daniel Boon. It’s just, uh, being born out of necessity. And we can talk about that later. Um, but, uh, yeah, boonlegal.com or hello@boonlegal.com if you want to just send us an email. Um, and, and, uh, yeah, we support everybody from formation through M&A. We do everything on a flat fee basis. Uh, our monthly plans are not requirements and we don’t have any commitments. We’re just here to try to help people to build good businesses, uh, to, to build, uh, things that are valuable to the communities for which these people serve and for the constituents they serve, and more importantly, the people in their businesses, uh, who they lead because, uh, the more that we can support our clients and their businesses, the more people, um, that, that, that come behind them that we’re also supporting and we don’t take that for granted.
Lee Kantor: Well, Michael, thank you so much for sharing your story today. You’re doing such important work and we appreciate you.
Michael Woolf: Lee, this has been an absolute pleasure. Um, thank you so much.
Lee Kantor: All right. That’s the Lee Kantor. We’ll see you all next time on High Velocity Radio.

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