Thinking about going solo but stuck in anxiety and overplanning? In this episode, two lawyers who successfully left prosecution and big law share the real math, mindset, and first 90‑day moves that make or break a new solo practice.
In this episode, Steve Fretzin, Jordan Ostroff, & Jeremy Baker discuss:
- Deciding when and why to go solo
- Leaving a firm the right way and preserving relationships
- Planning for cash flow, costs, and the first 90 days
- Using AI and lean tech instead of heavy overhead
- Common mistakes with hiring, planning, and business development
Key Takeaways:
- The decision to launch a solo practice often comes from a clear moment of misalignment, realizing the “next promotion” or status quo is not the life or career you actually want.
- A realistic financial and marketing plan, what you’ll spend, how you’ll earn, and where new files will come from, is more important than a perfect logo, office, or tech stack.
- Maintaining integrity and open communication when you leave a firm protects your reputation, preserves referrals, and can turn former colleagues into long-term allies.
- Early-stage solos should prioritize cash flow and relationships over tinkering with systems; networking your existing contacts usually beats waiting on websites and ads to work.
- AI tools can dramatically reduce startup costs and speed up execution, but they are a supplement to, not a substitute for, consistent outreach and business development.
“What I did wrong in year one was I didn’t hire people, and what I did wrong in year two is I hired people the wrong way.” — Jeremy Baker
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About Jordan Ostroff: Jordan Ostroff is the CEO of Driven Law and Carpe Diem Consulting. A former prosecutor and the first lawyer in his family, Jordan overcame $200,000 in early business debt to build a thriving, low-volume personal injury practice. Now the best-selling author of Love Your Law Firm, he works 20–25 hours a week, allowing him time for family and coaching other attorneys to achieve a similar high quality of life.
About Jeremy Baker: Jeremy Baker is a veteran construction attorney and litigator representing owners, developers, and design professionals. In his sixth year of solo practice, he specializes in cost-efficient solutions for issues like contract negotiation and sustainable design. While an experienced litigator in 30+ venues and dozens of arbitrations, Jeremy prioritizes dispute avoidance and alternative dispute resolution. An early proponent of the Guided Choice Dispute Resolution System, he provides strategic advocacy to resolve high-stakes claims without the need for traditional litigation.
Connect with Jordan Ostroff:
Website: https://www.legaleasemarketing.com/
LinkedIn: https://www.linkedin.com/in/jordan-ostroff/
Connect with Jeremy Baker:
Website: https://designbuildlaw.com/
LinkedIn: https://www.linkedin.com/in/jeremysbaker/
Connect with Steve Fretzin:
LinkedIn: Steve Fretzin
Twitter: @stevefretzin
Instagram: @fretzinsteve
Facebook: Fretzin, Inc.
Website: Fretzin.com
Email: Steve@Fretzin.com
Book: Legal Business Development Isn’t Rocket Science and more!
YouTube: Steve Fretzin
Call Steve directly at 847-602-6911
Audio production by Turnkey Podcast Productions. You’re the expert. Your podcast will prove it.
FULL TRANSCRIPT
Steve Fretzin [00:00]
Hey everybody, before we get to the show, really big announcement for you. This is one of the most important things I’ve done in nearly two decades of working exclusively in the legal industry. It is the be that lawyer community, and it’s officially live today. This is a global platform designed to help lawyers become rainmakers, grow their law practices and take control of their careers. And it’s built for individuals just like you who want more. And it’s also for law firms who want to bring real business development coaching and training to their teams with a strong return on investment. Inside you’re going to find a massive library of content, practical courses, live events and direct engagement with rainmakers from around the world who are there to answer your questions and help you grow. Membership is only 699, per lawyer. It discounts available for groups, and for a limited time, April 15 to April 30, you will get that deal as a founding member at that special rate I just mentioned, you have two weeks take action. Be that lawyer.com/community I’ll say it again. Be that lawyer.com/community to sign up today. Hope to see you there. And by the way, enjoy the show.
Narrator [01:11]
You’re listening to be that lawyer, life changing strategies and resources for growing a successful law practice. Each episode, your host, author and lawyer coach. Steve Fretzin, we’ll take a deeper dive helping you grow your law practice in less time with greater results. Now here’s your host, Steve Fretzin, Hey
Steve Fretzin [01:33]
everybody, welcome to be that lawyer. I’m Steve Fretzin I’m so happy you’re here today. We’re going to have an amazing show. We’re doing something a little different. This is a be that lawyer live. We have a panel of amazing experts that we’re going to be working with today for this show and the next show to make sure that we are helping you to be that lawyer, confident, organized and a skilled Rainmaker. So I want you guys to really take to heart what they’re saying. If you’re looking to become a solo and go out on your own, or if you’re an existing soul looking to take things to the next level, this show is going to be a rock star show for you. So I want to just share that, and again, I think just a lot of great concepts and ideas that will be passed along the way. Even if you’re in big law and you’re never going to leave big law, that’s okay, too. We’re happy that you’re here and listening. So with that, I want to also just mention briefly the new be that lawyer community is up and running. We’ve got nearly 60 attorneys in there and growing. Every single day, there’s open live chat rooms all about growth. We’ve got a library full of content courses you can take, live events like this that you can attend and and lots and lots of communication in there. So check that out at be that lawyer.com/community all right. With that, we’re going to jump in and get started. We’re not doing a quote of the show today. We’re skipping it. We’re going to go right to introductions. I’ve got Jordan Ostroff and Jeremy Baker. Jordan Ostroff, everybody is the founder of carp DM consulting and driven law. And do you want to just take a moment, minute, two minutes, whatever, to just share about yourself, and then we’ll go to Jeremy
Jordan Ostroff [02:58]
Sure, despite how I look. I am still a real lawyer with a bar card in Florida, but I just for me, the biggest thing was I realized being a great attorney did nothing for my life and practice because nobody was in charge. And so I made the decision to focus on being a great marketer and a great law firm owner and hired phenomenal attorneys. And so I’m really excited to share I know we’re focused more on the day one. Let’s go solo. I went solo day one out of the state attorney’s office. So I’m excited to tell you everything I did and what worked and what didn’t. So learn from me.
Steve Fretzin [03:34]
Awesome, fantastic. Okay, everybody, we’ve got Jeremy Baker, who is the founder of Baker Law Group and operation palm tree. Welcome. Jeremy,
Jeremy Baker [03:42]
Thanks, Steve. Tell
Steve Fretzin [03:43]
us a little bit about you. You’re the next contestant on this be that lawyer.
Jeremy Baker [03:48]
So from 2001 until 2019 I was in the big law world. I had two jobs during that time frame. Spent about 14 years at an amla 200 firm, where I spent half the time as a partner, half as an associate, where I left out on my own and launched Baker Law Group right before covid in late 2019, great timing, as always. And I am now, I think, in my sixth year running my firm,
Steve Fretzin [04:13]
fantastic. And then also operation palm tree.
Jeremy Baker [04:16]
Yeah, a couple years ago, I got pretty excited in the topics that we’re going to discuss here today, and so I threw up a website where I now have 50 or so pretty long videos about a lot of the stuff that we’re going to talk about today, sort of documenting my journey from leaving the employee of others and launching your own firm so it’s all free. There’s no paywall or anything like that, so operation palmtree.com
Speaker 1 [04:39]
Yeah,
Steve Fretzin [04:39]
well, let’s jump in and get into things. I mean, it is a scary, scary idea for most attorneys to even consider going solo. And so there was a moment that, you know, each of you had when you were deciding to do that. And I know Jordan, your story is very different than Jeremy’s, but, you know, we all, I mean, me too, I had to decide after being, you know, making great money, and. Corporate world to go off on my own and start the be that lawyer business. How do you what was the moment you kind of decided that, like Jordan, I mean, for example, not to go into a law firm, but to start your own
Speaker 1 [05:10]
gig?
Jordan Ostroff [05:10]
Sure. So mine was really easy. I was a prosecutor. I did. I was prosecuting people for, like, unintentional deaths, so relatively serious, not intentional murders. And so the next promotion for me was sex crimes. I applied for it, thinking I wanted it. They told me, I did not get it. And I was happy, they told me, but I would get the next one. And my heart, just like, fell through my butt, metaphorically, not literally, thankfully. And I was like, Oh, wait. Like, I don’t want the next promotion. And so, like, I sat down with my boss and was like, Hey, what are the options? And they were like, This is the only option. I was like, great. I’m gonna put in notice, and I’ll see you all later, because I don’t want the promotion. And so for
Steve Fretzin [05:48]
me, was super easy. You went home and then you were robed in a Hawaiian shirt from day one,
Jordan Ostroff [05:52]
right? I wish, I wish I committed to Hawaiian shirts way sooner than I really did, but we’ll talk about that more down the line.
Steve Fretzin [06:00]
Right, right. Okay, so it was not, it was not necessarily something you had planned on, but it was like the next obvious thing to do and leaving that type of a role.
Jordan Ostroff [06:10]
Yeah, it was my it was really my only option, unless I wanted to stay stagnant, because they’re just you. They weren’t going to move people up to homicides without going through sex crimes. And I thought that was going to be my route, until in that moment, I realized it wasn’t,
Speaker 1 [06:23]
yeah,
Steve Fretzin [06:24]
and so, you know, here’s Jeremy and a different situation, big law making, I’m sure, great money. And then you’re just like, at a what type of tipping point to say enough of this? Or how did it come about to go out on your own?
Jeremy Baker [06:36]
Well, I suppose a quick and snappy answer to the question would be, I did the back at the napkin math, and I figured out how many hours I spend from the moment I leave my house in the morning until the moment I get back at the end of the night, basically anytime that I’m not spending with friends and family that I’m putting towards my career. And I figured out what was I really, you know, earning per hour. And that sort of made me realize that what I needed to accomplish in my own law firm was not that daunting. I did not need 2000 billable hours at the exact same rate that I was billing at the big law firm. You know, that was an important moment for me. I also, after quite a lot of planning, found the right vendors to build my website with the right message that I was going to take to the market. And it became evident to me that I really thought I could do it because I was leaving big law with two clients, and I financed my firm on a credit card. And so there was some planning that went into it for sure, but it was really more gradual process. My wife’s also a solo she left out nine years ahead of me. I listened to a lot of podcasts, thinking that I’d learn about law, practice, management to help her out. And I kind of went from I’m trying to learn for her this doesn’t apply to me, to maybe it does apply to me, but I’m not interested. To maybe I should be interested. And then I got to a point where now I’m very interested that I don’t know if it’s feasible. And then there’s like a tipping point where I said it is for me and it is feasible, and it is go time,
Steve Fretzin [08:01]
yeah, and there’s, there’s anxiety for lawyers that are looking to make this decision for a number of reasons, but one in particular is, you know, let’s say you’re not taking business with you, right? Like Jordan starting from zero, as opposed to having some clients. Or it could be the overhead, just concern about, like, Hey, I’ve got to get a receptionist, I have to find a location, I have to get all this tech stack. That’s not necessarily the case anymore. I know it was maybe 10 or 20 years ago. How do you guys see what’s really necessary today to go solo, versus maybe 10 years ago? Jordan,
Jordan Ostroff [08:32]
so you all are lucky. You have this thing called AI, which I guess existed when I did this, but not in the same way. And I want to be very clear, I don’t think AI is better than a really good expert in human on most things, but on day one, when you have nothing, Claude can code you a more than good enough website in 20 minutes, versus you spending $5,000 on it, which you might do later. But in terms of like, what is needed to go out on your own, it’s incredibly easy to check all the it’s much easier to check all the boxes now with AI and just get started and then reinvest the money into having humans and other programs do things better for you later.
Speaker 1 [09:14]
Yeah,
Steve Fretzin [09:15]
Jeremy,
Jeremy Baker [09:16]
for me, since I’m the breadwinner and I have four young kids, when I was leaping out, there was some math that I had to do, and I’m certainly more of a social science major type than a mathematician, but it’s pretty simple. I mean, you figure out everything you need to buy. You figure out the cost side. You make some projections about where you think you’re going to get your revenue from. You know, I nailed the cost side. It was a piece of cake. The revenue side, I didn’t wind up getting work from the sources that I had identified, but I had enough confidence that I had an idea that I wouldn’t be just sitting alone waiting for the phone to ring. And so there’s a lot of things that you can do, but I think for me, that was most important. I needed to assure myself that I wasn’t going to, you know, quit a great law firm partnership and then promptly go broke. I.
Speaker 1 [10:00]
Yeah,
Steve Fretzin [10:00]
yeah. Well, and I think it’s smart if you can do, if you’re gonna do it, you know, save up for it like you have an idea that you’re gonna go solo in six months or a year, you know, maybe don’t go on that trip to Europe. Maybe don’t, you know, buy that expensive, $80,000 car, right? Put some money in the bank, get 2030, $50,000 set aside, and realize you don’t have to have an office or a receptionist, or all these things that
Speaker 1 [10:22]
were
Steve Fretzin [10:22]
major cost centers for people going out on their own and having a $10,000 website. So you can do these things on the cheap, and you can get a VA or virtual assistant or whatever. There’s all these options now, which I think is really, really important, but I think putting a plan together where you can sort of look at what those expenses are. And I also think, you know, put a business development plan or marketing plan together, if you can, via me or you or anybody that can help you with that, so that you have an idea of, you know, what relationships you have and what clients you have and what opportunities you can have, so that you can pick up business fairly quickly from, you know, the first month that you’re out. Okay, the other big thing I want to ask you guys about. And again, this might be more of a Jeremy thing, but there’s a lot of anxiety and issue with by the way, word of the day is anxiety, apparently, so. But with people leaving a firm and doing it the right way, and that’s not always easy to do when you’re in a bad culture, when you’re, you know, taking business away from a firm that maybe you didn’t bring it in, but you’re managing it, and you’re their lawyer, and there’s all the different elements of how to do it right, how to do it wrong, I guess. Let’s start with you, Jeremy, and then Jordan, I’d like you to think about like, like, how, what are some things about that lawyers should be thinking about being three to six months before they leave to sort of help protect the relationships and the investment of the firm that they’re leaving so that they could do it in the best possible way? It’s
Speaker 1 [11:42]
a great
Jeremy Baker [11:43]
question, and it was one of my big concerns, because I like to joke that at 14 years of my last job, I was one of the new guys, because there’s a one to one ratio between associates and partners, which is not the most, not the best way to make money for a big law firm, but it tended to have people stick around. And I really knew my couple 100 partners and couple 100 associates very well, and I wanted to get out on good terms. And I was actually ready to go, literally, I could have flipped the switch and left. I think it was like 10 months before I actually did, because I was handling some significant things. Where had I left, it would have been a big inconvenience to my teammates and the clients. And so I deliberately delayed until I had certain very consequential things in a spot where nobody would lose a step, and I was very careful to follow all the rules of the partnership agreement, understand the law. And I was worried when I told my boss that he’d say security is escorting you out of the business in five minutes, out of the building in five minutes. Here’s a cardboard box. But nothing could be further from the truth. You know, my practice group leader threw a party for me, and everybody came, and there were little because I’m in the construction law business, they made little cookies, little hard hat cookies that said, Good luck Jeremy on them. And so I have been able to maintain those relationships, and it has been personally and professionally, wonderful for me. So I think it’s a really good question.
Speaker 1 [13:03]
Well,
Steve Fretzin [13:04]
it ends up being a big time home run if you can pull it off, because then you you realize, hey, there are people I can send stuff to if it’s not a fit for me, and if they have stuff where there’s conflicts or rate issues, they’ve got someone to send work to. So there’s a huge upside if you can pull it off. It doesn’t always happen that way, right? But the goal is, is that, if you can make that work, great? Jordan,
Jordan Ostroff [13:24]
yeah. I mean, look, we have one thing for us as lawyers that differentiates us from each other. At the end of the day, it’s our Word or our reputation, or, you know, whatever you want to call it, like we don’t have a patent and trademarks over specific types of motions or types of cases, we can handle those things. And so I think open and honest communication becomes great. And if you are currently at a firm that’s going to do what Jeremy was afraid of, give you the five minutes out the door. That’s their choice. You know, like, I’ve never done that, and I would never want to work somewhere that would do that. I much prefer when conversations go the way Jeremy has. We’ve thrown parties for attorneys when they leave, same thing along those lines, but I think that all goes back to honest communication. Hey, you know, I’m getting ready to leave. You know, how much notice Do you want? What do you need from me before I go? Here’s, you know, all my files are up to date. Those kind of things become, you know, immensely helpful.
Steve Fretzin [14:16]
Yeah, and when, when someone is thinking about making a move like this. I guess you guys could use your own experiences, like what you knew then and what you know now, right? Is quite different, because you both experienced being out on your own. What are some things that you say, hey, if I could have done this over again, this is what I would have done differently. Jeremy, what’s your hot take on that?
Speaker 1 [14:36]
You know,
Jeremy Baker [14:37]
I spent a couple years thinking about the jump before I left, and so I don’t know that there’s a whole lot that I would have done differently right out of the gate. I have made so many mistakes since, and I make them every day, so I’m not implying otherwise, but I had a good hopefully
Jordan Ostroff [14:51]
not showing up for the webinar as a mistake,
Jeremy Baker [14:53]
though. No, no, I would say that, you know the it kind of depends based upon who you are and what you’re trying to do. I mean, my. Answer would be different if you were a group of lawyers leaving together, and it would be different if you were a somebody who was seeking out consumers, individual people as clients, versus somebody like myself that is a business to business lawyer for me, getting together my list of contacts and making sure on day one when I hit the ground, I was ready to let everybody in my network know what I was doing, is the most important thing that I did, and I think that’s actually applicable to everyone. But so no matter who you are, if you’re thinking of leaving like, get your Rolodex together, connect with everybody on LinkedIn and get ready to let everybody know what you’re doing. But there’s different strategies for different types of exits with in different configurations.
Steve Fretzin [15:43]
But was there you mentioned a lot of mistakes? Was there a particular mistake that happened in year one that you’re like, that you didn’t plan for that you’re like, oh, wow, I really wish I had known this ahead of time.
Jeremy Baker [15:52]
Yeah. I mean, what I did wrong in year one was I didn’t hire people, and what I did wrong in year two is I hired people the wrong way. So, you know, it’s a lot of trial and error.
Steve Fretzin [16:02]
Yeah, damned if you do, damned if you don’t. But there’s probably some takeaways about how you think about hiring, and how you consider, like, like, what your first hire, who your first hire, should be, right from the get go, or within six months, or whatever. Is it an admin? Is it a paralegal, as an associate? And I think that’s maybe something we’ll get to in, you know, later in this episode or the next. But Jordan, what’s your take on this,
Jordan Ostroff [16:26]
on what you just said, or the original question? Yes, Jeremy,
Steve Fretzin [16:28]
yeah. Like, maybe it’s just, if you had to start your firm over again, what would be a one or two things that you would have? Yeah, I wish I had known this then.
Jordan Ostroff [16:36]
So I want to echo what Jeremy said a ton and go one step farther. Like I was a prosecutor for over three years. I did not need cases. I had more than I wanted anytime. I should have been networking. I should have been staying in touch with those people. And so, you know, on day one, going, what, doing, what Jeremy said is great, you know, putting it on LinkedIn, reaching out to everybody, but like, I would have had a really easy time doing it six months earlier. And like, Hey, I don’t need cases from you. Like, Let’s just hang out. Let’s just hang out. Let’s catch up. You know, haven’t seen you since law school, those kind of things.
Steve Fretzin [17:05]
Yeah, yeah. And, I mean, I think that, you know, we do this on the show, and we’ll do this at the end of each episode with you guys, which is, like, what’s your big mistake? And the beauty of mistakes is that we learn from them and we come out, hopefully better on the other side. And so, you know, I had a mistake years ago where I just, I got, you know, shiny Penny syndrome. I was just, you know, picking up every shiny Penny. And I had, I think, four businesses and an association all running, but I was running all of them, and I was just overwhelmed all the time. My overhead was massive. And it took me making those kinds of strategic decisions that I thought at the time were great that turned me around and said, Hey, you better slow it down. Man. You’re you’re running faster than you can actually handle it. So I love that you guys have some good takeaways on those types of things. Hey, everybody, your next big client might call it 8pm on a Saturday night. The question is, who’s picking up with Lex reception? A real person answers every call, 24 hours a day, seven days a week, so you never miss a lead, no matter when they reach out, no AI agents, no voicemail, just professional legal, literate receptionist representing your firm the right way around the clock and right now, be that lawyer listeners get 250 off their first month. Visit www dot lex reception.com/partners/be, that lawyer to claim your offer. That’s www dot lex reception.com/partners/be, that lawyer. Hey, everybody. Steve Fretzin Here and@lawyer.com They don’t just market law firms. They help them grow from connecting millions of consumers to trusted lawyers to smarter intake and industry leading events, they’re building stronger connections across legal visibility, intake events, growth. That’s lawyer.com Check them out today, with proven SEO and digital marketing strategies that drive actual clients to your firm. Rankings.io. Prides itself on proof, not promises. Mentality, the best firms hire rankings.io. When they want rankings, traffic and cases, other law firm marketing agencies can’t deliver. Get more rankings, get cases and schedule a free consultation@rankings.io today, what would you say then? Are the top two or three things that a lawyer should prepare for. And I’ll get I’ll give you an example before leaving. For example, Cleo, is it lawmatics? Is it Clio, is it, you know, one of those, you know, CRMs, like, what’s the tech stack? Like? What are the things that they should be really studying up on and learning and getting comfortable with before they move out on their own? Jordan, what’s your take on
Jordan Ostroff [19:40]
that as of right now, a Claude chat, GPT, Gemini, something along those lines. I would
Speaker 1 [19:46]
not,
Steve Fretzin [19:46]
but at those skills, like being good at setting up those and maybe creating agents, things like that,
Jordan Ostroff [19:51]
maybe I don’t. So here’s my thing. I wouldn’t commit to a platform on day one, because you don’t know what you really need. Clio lawmatics, I think they’re. Phenomenal programs. You may end up with them, but on day one, I don’t think you need that. And eight, same thing for agents. Maybe that might be too far, but like, here’s the thing. You know, we’re sitting here talking both Jeremy and I identified our biggest issue was letting people know what we were doing. Great. Hey, chat. GPT, I just left big law. I just left the state attorney’s office. I’m opening up my own firm. How do I help people know on day one for $0 what I’m doing and do what it says, you know, like just having those conversations to fill in the gaps, because look, on day one you can’t afford us one on one. I don’t think you know, most lawyers are doing what Jeremy did. They’re going with a credit card, and a couple clients I was going with not a credit card, and no clients, you know. So how do you get the targeted information for you? So my tech stack on day one would be whatever AI program I’m most comfortable with to fill in the gaps until I can hire better help.
Steve Fretzin [20:51]
Yeah, I mean, I would throw out that if I was going out on my own again, or if I’m a lawyer going out on the on one’s own, I would put together a plan, right? I would get a plan of, like, how I’m gonna, you know, like a plan with a budget, a plan with a list of names, a plan of where the low hanging fruit is, how I’m gonna leverage that network. I’m gonna start building my brand that way. I have, like, a GPS system from day one of what I need to do, what are my priorities? In fact, one of my clients just left the firm, went to another, and I said the same thing to my goal, man, you need to write like a mini plan about how you’re gonna, you know, lateral properly and and make it happen, and then get the most traction. Jeremy, what’s your take? I want to
Jeremy Baker [21:30]
echo what Jordan said about Claude. I ignored AI until January of 2025, and then I’ve been really paying attention to it ever since. And if you are not using Claude right now you should, you know, as soon as this webinar is over, you should sign up. It’s like 20 bucks a month, like, flip off the, you know, toggle that says that they can train on your data. And it’s very user friendly. And everybody should figure out, you know, where their next vacation is going to be, or whatever, by using this and it’ll it’s a way to figure out how to make it useful in your law firm. So, you know, it’s changing really quickly, as far as you know, the tech stack. I mean, yeah, practice management software. CRM I what I would just say is I wouldn’t allow if people are going to wring their hands for six months trying to figure out what practice management software they’re going to use, then I think that they’re maybe looking for a place to hide because they’re not ready to make the move. It doesn’t matter. Pick one, they all basically do the same thing. I picked one. I’ve been happy with it for six years. I’ve got no desire to change. So there’s some of that stuff. But I think that if you’re really gonna leave, certainly under circumstances like me, where I was gonna go into a bunch of debt, I was taking two clients, I really needed two things, like I needed a financial plan to figure out what I was going to have to spend and how I was going to get money. And I needed a marketing plan. I needed to have an idea for how it was going to turn two clients into more clients and things that people need less than they think to get started. And I don’t know that cost is really an impediment now, everything is really, really cheap.
Steve Fretzin [22:58]
Yeah, yeah. It’s a different world right than 10 years ago. So people can really leverage that via AI. I mean, I’m a chat GBT guy at this stage, I haven’t really touched Claude or Gemini or any of that stuff. What’s your take Jeremy, on why Claude is so much better than chat GBT,
Jeremy Baker [23:12]
it is because their desktop software co work is something they’re ahead of the others with that software in it. It can connect to word, and it can redline documents, and it can look at your emails, and it can do a lot of stuff. You know, for example, I was chatting with it this weekend about what we might do, you know, over winter break with the kids, and we’re talking about, is it Hawaii? Is it Thailand? Whatever? I literally connected Claude cowork to Chrome, gave it access. I logged into my American Airlines site, and I said, run wild and see what’s out there. And it did all the searching that it would take me, you know, weeks to do, and it came back and it said, here are your options, and this is my recommendation so it can it’s not back on its heels playing Question and Answer necessarily the way that, you know, I was sort of using chat GPT like I use Google, right, you know. So it’s an interface. You ask a question, you get an answer. The agent Tech experience, where it can be a little bit more on its, you know, leaning forward, rather than being on its back hills. Answering questions is, I think, what really sets Claude apart. But this won’t age well, because next week, there’ll be, you know, a chat GPT
Steve Fretzin [24:22]
about that’s the rub, right there, right? Jordan,
Jeremy Baker [24:25]
right, right now is great,
Speaker 1 [24:27]
yeah,
Jordan Ostroff [24:27]
I totally agree with that analysis. I don’t know that it’s going to change a ton because, so I’m interested, not necessarily, the differences of what they do right now. What’s the payment model? So right now, open AI has 40 to 50 times as many users as Claude. The payment model is similar to Facebook. It is the user base. So having open AI incorporate, you know, ads into their free account, something like that, like I see that happening claude’s payment right now, most of their money is coming from APIs with developers, and so you have chat GBT being more. Consumer facing, you have Claude being more developer facing, which is why I think, like, Steve, you talked about it, and I like talking to chat GPT more, but I agree with what Jeremy said for like, the hard, you know, rolling up the sleeves and doing Claude is like a night and day difference.
Steve Fretzin [25:14]
Yeah, awesome, awesome. Well, I’ve got one more question before we wrap up with what your, you know, with your biggest mistake you’ve made, being in business and and going solo and scaling up. If there’s somebody listening right now, and you would say, hey, you’ve got 90 days to determine, it’s your first 90 days as a solo did that’s going to determine success or failure, struggle, success, whatever it might be, what would you say are the the main things that are going to turn someone in the right direction? So they’re having success versus struggle? Jordan,
Jordan Ostroff [25:49]
in terms of to make the decision, or once they make,
Speaker 4 [25:52]
let’s say
Steve Fretzin [25:52]
the first 90 days, they’re on their own.
Jordan Ostroff [25:54]
Okay? So the 90 days, right? So here’s the thing. Look, you need money to stay in business. Cash flow is what keeps you in the game? So how are you going to find cases in the first 90 days? Probably for no money or little money, you know, like there’s only one credit card is only going to get so much in Google ads. So who do you know? Who do you already know? Who can you meet? Where can you generate that initial stuff until you can redeploy the capital towards your business? That’s the biggest thing in the first 90 days is have money coming in so you can continue to operate or reinvest it.
Steve Fretzin [26:26]
Cash is king. All right, Jeremy,
Jeremy Baker [26:28]
I couldn’t agree more. I spoke with a lawyer the other day that was under similar circumstances with me, similar practice, business to business. And, you know, he was talking about organic search, and he was talking about, you know, paid ads as a way of propping up his firm at the beginning. And if he was a business to consumer lawyer, you might be able to use local service ads or paid ads to get in front of individual consumers. But his idea for getting work in the first 100 Days was not going to work for what he was looking for. There were good ideas, but there are longer plays, and he needed to get in touch with everybody in his network. Because, as Jordan said, cash is king. And like, what you need to do when you come out of the gate is you have a certain amount of time to get enough clients to dig yourself out of whatever debt you’ve gotten yourself into, and then, you know, step forward or the firm will fail. And so you need a realistic plan in the short term. For me, it wasn’t trying to meet strangers on the internet. That’s a longer play. That’s year one to you know, five. For me, it was every person in my network needed to know what I was doing to maximize my odds of being able to dig myself out of the hole of death that I knew I was going to dig.
Speaker 1 [27:40]
Yeah,
Steve Fretzin [27:41]
I would say I meet with people who are looking for jobs less now than in the past. But that was sort of something that I did just because people say, Steve knows a lot of people, and you should talk with Steve. And I would look someone in the eye when they’re looking for a job. I go, what’s your job? They go, I don’t have a job. I go, you do have a job? Your job is to find a job like it’s a full time job, finding a job that’s your job. And they look at me like, oh, and I think it’s the same thing when you’re starting a solo you need to your job is to get out there and and knock on doors. I mean, you should be looking at at your friends and family. You should be looking at your former law school friends and former partners and other firms. You should be looking at any low hanging fruit that of people you already know. To Jeremy’s point, I think that’s spot on, building up, you know, your LinkedIn profile and making sure that everybody knows that your book cover. I don’t think people realize how powerful something like having a good LinkedIn profile and how that helps, you know, satisfy people’s understanding of what you’re all about. And so as you’re out networking, you’ve got that maybe even before a website, just sending people to your LinkedIn, that’s okay, but ultimately, you know, that’s what we need to do to get the business in the door. And you could then what happens is, a lot you guys can back me up on this. A lot of attorneys get just mixed up in the minutia of it, right, setting up the tech stack, or trying to build that website, or doing all the little things they think are important. And they don’t really get out there, because that’s the harder thing, right? And then that, then they realize six months in, they got nothing except bills. So I think that’s any any final thoughts on that before we move to your big mistakes?
Jeremy Baker [29:15]
Yeah, I would just say that. You know, when it comes to getting clients, and particularly if someone has historically worked for somebody else, or maybe some reluctance to yell as loudly as they can and to let everybody know what they’re doing. But I heard somebody once say something that really stuck with me. Kind of cracks me up every time I hear it. When you sell professional services, keeping what you do a big secret is not a good idea. So you know, you need to let everybody that you you know possibly can know what you’re up to, particularly if you are in need of clients. And then, you know, when it comes to some of the paralysis that can come from over planning, I mean, I’m a planner, and I did a lot of good planning, but I also did a lot of planning that didn’t make a lot of sense, and in hindsight, it was you. Know Me trying to create some comfort for myself around an area where it really couldn’t be created, and it was delay and I was just sort of like getting myself to the point that I was ready to go. So I’m a planner, but you don’t want to plan things that aren’t really going to help you and yell from the rooftop what you’re doing when you get started.
Steve Fretzin [30:16]
Yeah, put your shyness aside for a little bit, right? Jordan,
Jordan Ostroff [30:20]
yeah. Remember Mad Libs, at the very least, Mad Lib right? So I help kind of person achieve certain outcome through what you actually do. I help the best lawyers get out of their practice and actually own a business through one on one coaching, you know, like, That’s it, just mad lib, those three things, and that’s your elevator pitch,
Steve Fretzin [30:43]
yeah, well, and I think, you know, I’ll go back to something I say all the time, and I’ll just reiterate it, that before, you know, years before, or a year before, you go out on your own, you should be, you know, studying, like, getting an MBA in business development and marketing. You should be listening to podcasts like this. You should be reading books. You should be reading articles. You should be talking with rainmakers and interviewing them for yourself personally that what are they doing to be successful people in your space, in your practice, like you need to prepare to go to battle. It’s like, I’m I remember, my brother joined the Marines, you know, like, got a he failed out of college, and then he went, like, in the Marines. And my dad kept saying to him, he’s like, You better do some push ups. You better do some sit up some sit ups, like, you’re going to the Marines. And my brother’s like, ah, and they kept it crap kicked out of him in the Marines, because he didn’t plan for it, right? So let’s not make that mistake. And speaking of make big mistakes, Jordan, what’s one big mistake you made? And because of it, you ended up on the better side of things.
Jordan Ostroff [31:39]
Oh, man, I like that you framed that the second half of it. So I bought a traffic ticket business that I thought would be great to move in with my criminal defense practice. I learned a lot from it. Let’s put it that way, it was a very great learning opportunity.
Steve Fretzin [31:55]
Okay, Jeremy,
Jeremy Baker [31:57]
probably the biggest mistakes was me not understanding how to hire properly, and having a number of bad hires that, you know, set me back in certain ways. I think I’d be further ahead if I did then what I’m doing now when I hire.
Steve Fretzin [32:12]
So you just, you know, we have to make these kind of, hopefully not costly mistakes. I think hiring can be of the more costly mistakes, but you know that’s going to happen a little bit before we figure out what to do. You know how to do it the way that’s going to, you know, stick and that’s tough, but that, but those are very important life lessons. You can’t sometimes you can’t get through it until you’ve been
Speaker 1 [32:34]
through
Jeremy Baker [32:34]
- I also, you know, to your point, you can learn from your own mistakes, or you can learn from the mistakes of others. And that’s why, like, the group that you’re putting together is so important. Steve, one of the best things that I’ve done is I’ve joined a bunch of masterminds. Jordan and I met in person at masterminds years ago. You know, the group you’re putting together now is great, if you can crowdsource the best thinking of a lot of people who are trying to do what you are doing, and you can hear, you know what they have done that has worked and what has not worked. And if you can get in these communities and have people answer your questions instead of learning from your own mistakes, you can learn from the mistakes of others, and that is really a way to propel yourself forward much more quickly.
Steve Fretzin [33:15]
Awesome. Well, listen as we wrap up this first segment on let’s go solo. I want to take a moment to thank our amazing sponsors, lawyer.com Lex reception rankings, io and pimcon, awesome coming up in October, again and again. If you’re interested in hearing more about what Jeremy was talking about and what I talked about earlier the be that lawyer community. Be that lawyer.com/community Jordan. People want to get in touch with you. They want to network with you. Hear more about your business. How do they get in touch?
Jordan Ostroff [33:41]
Sure. So if you look up Jordan Ostroff online, there’s only two of us on the bearded one in the Hawaiian
Steve Fretzin [33:47]
shirt, yes,
Jordan Ostroff [33:48]
thank you. I appreciate that. Steve. Let me know where I send the bribe. No. And then Jordan ostroff.com o, s, t, r, O, F, F. Like I said, there’s only two of us. So I got to the website first.
Steve Fretzin [33:58]
There you go. The more famous of the two, Jeremy, how about you?
Jeremy Baker [34:01]
Best to contact me through Operation palm tree.com. Which is where I’ve sort of documented my journey for everyone. And you know, if anyone’s wondering about the funny name, back when I was at the big law firm, and I was talking to my wife, you know, emailing them over the firm systems, I couldn’t say, like when I leave here, you know, I needed to code word. So the code word was Operation palm tree. And so I decided to name my little passion project after my secret, secret code word with my wife.
Steve Fretzin [34:29]
Nothing like a great story behind a name, wonderful everybody. Well, I appreciate you sticking around for this first segment. You know, we’re coming right back with another segment on, let’s go solo, coming up soon, working with you guys twice a week, every week, on be that lawyer to help you. Be that lawyer, confident, organized in a skilled Rainmaker, take care, everybody. Be safe and well, and we will talk again soon.
Narrator [34:54]
Thanks for listening to be that loyal, life changing strategies and resources for growing a. Successful law practice. Visit Steve’s website, fredson.com for additional information and to stay up to date on the latest legal business development and marketing trends, for more information and important links about today’s episode. Check out today’s show notes.
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