00:00:00 Sana: You know that moment, listeners? Let me let me picture it for you. Everything on paper looks right. You have the career title income, but then there's this disconnect. And it's not that it's broken or it's it's dramatic. There's this misalignment. Something feels off. And, you know, the strange part is listeners, you can stay there for years functioning. You're performing, you're even succeeding. That's the surprising part. While quietly outgrowing the life he once worked so hard to build. And today's conversation, it's like it lives right at the at that edge. You know, this edge between, um, stability and uncertainty, between identity and reinvention, between what you have always been and what you might become.

00:01:10 Sana: So welcome back to your listeners to this blend. I am your host, and today we are sitting with someone who didn't just think about the pivot. You know, that pivot, that transition. But he actually made it after two decades as a trial attorney. Building a serious, respectable career. He reached a point many people would never admit out loud. I stopped recognizing the person doing it. That's a tough place to be. But it's not because he failed, but because he succeeded at something that he had outgrown. And at forty seven forty seven, with more to lose than ever, he walked away and he started from scratch. Yeah. And today he is building the AI Esquire, creating AI powered tools like K, a voice receptionist designed to help small law firms breathe again. But then, honestly, listeners, what makes his story different? That it's not neat. It's not wrapped up very neatly. It's still unfolding. It's an it's it's kind of this ever growing process, ever going journey actually, because, uh, and that's why this conversation matters, listeners. Because if you have ever stood at a fork in your life and you chose the safer road while quietly wondering about the other one, this one's for you. So listeners, meet my incredible guest, Eric Hoffman. Eric, welcome to Bespin. I am extremely honored to have you here with us.

00:02:56 Eric Hoffman: Oh, thank you so much. What a beautiful introduction. It's really great to be here.

00:03:02 Sana: And, uh, Eric, uh. Oh my goodness. I mean, uh, yeah, I mean, especially during Covid post Covid, many people, they have begun to gradually realize that, you know, life is also beyond just the career and the titles and the money. And it's not that you have to leave everything and, uh, you know, think about something else, but then the kind of risk that you took, I mean, twenty years as a trial attorney, I mean, uh, from the outside, I mean, it's a very respectable career. Things were working out for you. So what what exactly began to feel off for you, Eric? I'm I'm really curious. I think our listeners will be very curious to know.

00:03:46 Eric Hoffman: There's a lot of change that happens to a person. I guess when you're a lot of times you take work life and personal life and. And sometimes you believe those two. There are two different people almost. You create, you create one personality. And, you know, maybe one set of expectations for your personal life and then, you know, one for your, your professional life. And I think that's healthy. Uh, there comes a point though, where I, I, II, I developed certain interests. Uh, that was technology. I started to see these exciting developments in technology. Um, and that kind of moved over from my personal life into my professional life because I started to think about how those technological developments could be specifically, AI could be used to help my professional life. And, uh, I started to notice the response from attorneys was very closed. They weren't very interested in it. So I kind of was stuck where I was so excited to do something with this new technology. But the my colleagues were a little more resistant than I thought to use it. So I had a very there was a lot of friction there.

00:05:18 Speaker 4: Mhm. Mhm.

00:05:19 Sana: And was it because of the, the, um, ethical, uh, factors in there, uh, that, you know, you were seeing, especially the, the, um, kind of, uh, resistance or this, um, uh, the, the, the, the doubts surrounding, uh, the AI and this, you know, um, the connection between, uh, or the fact that, you know, AI has the potential to replace humans. That's how the fear kind of has been created or, or manufactured.

00:05:51 Eric Hoffman: Uh, it's an interesting thing. Uh, lawyers are afraid of predominantly one thing. Not so much being replaced by AI, but they're afraid of two main things. One is losing, violating the confidentiality. We may we take an oath and we have to. You've heard of obviously the attorney client privilege.

00:06:18 Speaker 4: Yes.

00:06:19 Eric Hoffman: If you use public AI tools, you can be uploading someone's personal information to say ChatGPT, you know, or Claude or Gemini. Uh, that is not allowed, obviously. I'm sure you wouldn't like your lawyer to be uploading, you know, your personal medical data or private financial stuff into, uh, public, uh, tool like that. So that's number one. And then number two is the. Chance for a malpractice suit. You know, they're they're concerned about, um, hallucinations. And they are concerned that potentially the output could be incorrect. There's been some very high profile situations where attorneys have been caught in court with citations in their memos that were to fictional cases or incorrect citations, and they've been sanctioned for that. So those are some fears that have really kept lawyers on the sidelines from adopting AI.

00:07:32 Speaker 4: Um.

00:07:34 Sana: These are legit ones actually, actually. And I think, uh, uh, you know, when we look at law and lawmakers, um, it would be very, uh, you know, one sided for an entire technology to replace it. I mean, it can, um, enhance or be a great enabler. And that's why that's kind of the, the vision behind AI Esquire. Um, but then I think personally, for me, the listeners may not agree, it would be very far fetched to, to imagine that, you know, the technology is completely replacing, uh, such a crucial, uh, position of, you know, lawmaker or law making or law because it's not for the technology, it's for the humans.

00:08:25 Eric Hoffman: Sure, sure. Yeah, yeah. If I could just comment on that. I, um, I believe it's, I do believe though, it's going to make a big change. The field's going to be changed dramatically. I think law is going to not be replaced by AI, but AI is going to make some probably the biggest and fastest changes ever to the legal profession. And I'm sure a lot of attorneys know that. And that's another fear they have. It's it's going to be some major changes. I, I mean, just one off the top of my head is, um, it's going to make clients expect a lot more because they're going to know that they have attorneys have these tools available. So they're going to expect their contracts to be written same day or, you know, by lunchtime, you know, and they're going to expect, uh, cases to be done quicker and answers to their questions to be obtained quicker. So the expectations of attorneys is going to go up tremendously. And those who don't increase their output and increase their speed and efficiency are going to fall behind.

00:09:42 Speaker 4: Mhm. Yeah, yeah.

00:09:45 Sana: That makes sense. But yeah, we are on pins. So not talking about AI much. Let's let's move on to your your journey in there. Uh, Eric, um, I mean, at forty seven, you made this decision. Um, realistically, realistically talking. It's, it's a stage where most people actually optimize for security, not risk. So it's kind of a blunt question. What made staying feel worse than leaving? Was it just this, uh, you know, kind of keeping yourself updated with the technology or was it more than, uh, this, this reason?

00:10:26 Eric Hoffman: I have to say that it maybe was stability that might have been what, what made me leave strangely. Um, thinking what I mean by that is thinking that I said, look, I'm thinking about myself down the line. Maybe five, ten years. I said, can I see myself doing this for another ten, twenty years even more? And that thought when I thought that way, I got a little bit of a feeling in my stomach, like a little bit of a flutter in my stomach saying, I got nervous. And I said, I'm not sure I want to be in this position professionally that you know, for that much longer because it doesn't change. It's it's static. I want it a little bit more change, as I mentioned. I wanted to adopt certain things that I had grown up, that I had started to like and wanted to make a part of my professional life. So I saw it as being stuck more than being on a path to to a goal. So I said I wanted a major change. I just wanted to shake everything up. And I believed that I didn't do it just one day. Sana, I didn't just, you know, get up from my desk and and walk away. I, I took a lot of time speaking to my family. I took a lot of time doing some research into the market. And, um, you know, at the end of the day, it turned out that the best decision for me was to take what looks like a risk, but to me was a way to step into a position that was better suited for my strengths.

00:12:21 Speaker 4: HMM. Yeah. I think this.

00:12:24 Sana: Speaks of a very big misconception, especially around career transitions, that it's always this dramatic or sudden, like how it's usually portrayed or thought about that, oh, one day, you know, you get out of your nine to five or your, um, whatever you are doing right now, you're not fleeing aligned with that. So just one day, uh, you leave everything and you start everything from scratch. I think it's kind of, um, a to, to some extent romanticized, but then it's not always that sudden or dramatic. You know, there's a lot of calculations done, um, a lot of, uh, research and, you know, probably connecting with people who may have, who would have probably gone through, uh, those turbulent waters and, you know, they have successfully done this transition. So yeah, I mean, that's, that breaks a huge misconception in there.

00:13:21 Eric Hoffman: Yes. Yeah. I believe a lot of people think that when I, especially when I first made this decision, a lot of people saw it as an overnight thing. But no, you certainly if I could give advice to people who might be listening or considering a similar move. It has to be done in stages, and it has to be done slowly. And you have to think about every possibility and and make sure that it is the right step for you.

00:13:54 Speaker 4: Absolutely. Absolutely.

00:13:56 Sana: Let's just take that because this is a million dollar advice. It's a million dollar advice. Uh, okay. Uh, moving on now, Eric. Um, um, and this is more like around identity and reinvention. Uh, because there's this, uh, idea, I think it beautifully has been captured in your even, uh, book title, the runways behind you. Uh, that maybe the past wasn't wasted time. It was, uh, preparation. I mean, not obvious preparation, but preparation nonetheless. And that's you. You just shared that with us, but then you weren't just changing careers, you were changing identity. Eric. So from a trial attorney to a founder building AI tools. I mean, that's not, not a small shift. So how did you deal with that internally?

00:14:57 Eric Hoffman: I was changing. Sana, I was I had become somebody that I felt that there was something inside of me that I wanted to create. I had this very strong, passionate feeling that there was an idea inside of me that I wanted to make real. I had this dream of taking this idea and bringing it out into the real world and making it an actual thing. You know, this turning some something in my head into something for real. And that that is what kick started me into, you know. Into doing that, into making that. And I, if I could comment quickly on the the runways behind you. I like to feel like the runway your, your past is a straight line, like a runway, not a crooked, you know, U-turn or loop de loops and, and and turns and backwards turns everywhere. Every step you take, even if it seems like a U-turn or going backwards, it's really a straight path to get you to lift off, you know, and take off to where you're going to be. So I just wanted to comment on the title of the book. It means a lot to me, that title, because I think people should look at it that way.

00:16:31 Speaker 4: HMM.

00:16:32 Sana: I really and thank you for for sharing that because I think a lot of people fear that, um, pivot means, uh, losing everything they have built. Um, and Erica, let's talk about the AI Esquire because you're not building it, you're solving a problem that you have personally lived through. Uh, so how, how, how different, um, does it feel to build something you believe in compared to succeeding in something you have outgrown? And that's a, that's a deep question, but yeah.

00:17:10 Eric Hoffman: Great question. Yeah, I, so I, it's funny, it's funny, it's, it's very, at first I felt that I would be so great at this that everyone would listen to me because I knew the problem firsthand. And I have all the solutions because I lived through it. But, uh, but it turns it turns out the market is a very brutal place. And one of my first lessons I learned was, even though I did live through it and I, I witnessed phone calls being missed and I witnessed, uh, receptionists saying the wrong thing and, and lawyers getting angry. And it was all kind of a mess. I said, I know how to fix this. So of course, when I proposed the solution, all the lawyers in the world are going to want to buy it, right? You know, but, uh, that's not quite what happened. Um, I had to, uh, obviously learn sales and learn marketing in the modern market and. Right. So that, I mean, that was, it was interesting to me how I, I have the solution and I still feel this way. If if I get my the lawyer I'm calling on to listen to me. I've always been very successful in in getting a positive outcome to a sales call. But the key is everyone's so busy today. Everyone's so cynical about salespeople. Uh, it's very difficult to get that attention. You need to just give someone a thirty second or a one minute demo or presentation. Um, but I still feel that if I can get that attention, um, our answer and our solution is good for, uh, and it's helpful to all attorneys.

00:19:13 Speaker 4: Um.

00:19:15 Sana: And, you know, um, this, uh, expectation, especially when you are building something, which, uh, has this backstory of your own experiences where you actually saw the gap or this gray area or the problem in there. You faced it and now you are building something which is actually going to. Uh, probably solve that exact problem for, you know, your fellow, um, colleagues or. Or the entire, uh, let's say industry in there. I think it's kind of expected that. Yes, it's going to, you are going to get a positive response in there, but I think. You know, when and this is something that in fact, many people who, uh, you know, have transitioned out of or who are going to transition out of their, uh, stable jobs or maybe nine to five or something specific and they're going to build something from scratch. They kind of, uh, will have to go through that, you know, a lot of self-learning in there. Uh, maybe they would go for coaching or, or, or, you know, finding mentor or networking because it's quite difficult to, you know, kind of that barrier point itself is a huge thing to, to cross.

00:20:35 Eric Hoffman: Yes, that's, that's the, that has been the most difficult thing. If I'm, if I can just say for me, son, I just learning learning what I don't know, I guess learning, you know, learning what I need help on and to say, gosh, yeah, I'm a forty seven year old founder and I need to learn cold calling and I need to learn how to do something basic like that. It's, it's difficult. It's not as easy as it sounds. And yeah, there's, uh, and there's some great people out there who are, like you said, coaches and I would highly advise anybody to utilize the amazing people out there who are either coaches or mentors or some call them gurus, but they're, you know, out there. There are some that are fantastic and they can really help you avoid mistakes. Uh, that you would have made, you know, without their guidance. So we're lucky enough to have that out there today. The ability to contact people and YouTube and obviously all social media and, uh, learn from other people, that is one of the most important things, I think, to being successful.

00:21:54 Speaker 4: Absolutely, absolutely. No doubt in that.

00:21:56 Sana: Eric, before we conclude, um, kind of, uh, a bit of a nuanced, uh, question here. So there's this growing narrative that, uh, everyone, uh, should follow passion or make a big pivot, but realistically, not everyone is in a position to do that. So do you think this kind of advice can sometimes be misleading or even harmful.

00:22:26 Eric Hoffman: Yes. It's a great, um, it's a great point. And yes, it could be, um, you, it's part of what I mentioned before where it's not something that can be done quickly, it has to be planned and you have to take account of your individual situation, whether it be financial, whether it be educational or your family. I have a family. You know, we I didn't have a million dollars in the bank or, you know, anything close to that. Uh, so it wasn't like, uh, you know, there were a lot of financial considerations, family considerations, you know, you want to look. So, uh, I would say you have to take stock of where you are, what your needs are, who relies on you and the people that you know, care about you, uh, And what their needs are and their opinions are, and you have to make the decision that makes is best for everybody because it's it's not a selfish decision. Decision. You make a decision for everyone who cares about you too. So, um, you have to have a lot of talks and be very open and honest with, with what could happen, both good and bad. And so, so the answer yes, it could be negative. If you don't do the appropriate analysis of your situation and the pros and cons of making such a move. But it can be done. It can be done. I think in almost every situation, if you if you plan correctly.

00:24:08 Sana: Yeah, let's have the caveat in there. If you plan correctly. Yeah.

00:24:12 Eric Hoffman: Yes, that's definitely the caveat.

00:24:15 Sana: Okay. So, um, That. I mean, honestly, listeners, I think, uh, these aren't simple or feel good transitions. They definitely come with trade offs. That's something we cannot dismiss. Um, and sometimes, you know, there are contradictions that we don't fully resolve. So I think it's very important to, uh, you know, if you want to take some highlights from this episode, I would highly, highly suggest advice. Take this as the topmost highlight from here. And of course, uh, Eric, um, our listeners, if they would further would like to connect with you and of course, explore more about AI, Esquire, the work that you are doing, uh, you know, what's, what's your vision behind it? They would love to know more about it, how they can reach out to you.

00:25:05 Eric Hoffman: Yeah, I love it when listeners reach out to me by email or on my website. So, uh, the website is ai dot I o, which is A I e s Q u I r e I o, and my email is Eric, E r I c at Esquire dot I. Oh, and if anyone writes to me and says they heard me on your show, Sana and and and asks me, I will send them a free copy of the book just for being a listener and because I love for them to read it. And it would be my gift to you for, for listening to the show. And, uh, it would be a pleasure for me to send you a copy of the book. So, and if you have any other questions or want to discuss, I love when that happens and listeners write to me. So go ahead and write and we can, uh, have a conversation.

00:26:02 Sana: That's beautiful. That's generous. For listeners, I'll mention all the details, all the links in the show notes. So reach out to Eric. Just share with him that you heard him on this blend and, uh, do get the copy free copy of the runways behind you. Eric's book and know more about Esquire and, uh, listeners. Honestly, I mean, this episode, I think, um, not episode I, I must say there's something honest about a story that isn't finished yet. There is no clean ending here, no polished. And then everything worked out, you know, it's all, uh, you know, flowery and all fluff. It's just a person standing in the middle of the build, figuring out as they go. And maybe that's the real takeaway from today, that the pivot isn't about certainty, it's about alignment. And it's not about escaping fear, but choosing which fear you are willing to live with. Yeah. So, uh, thank you so, so much, Eric. Um, I absolutely loved how candid you were and, uh, very balanced and, and mature take on this because it can be really, really a very romanticized, you know, it can go to extreme, but I was in it certainly.

00:27:28 Eric Hoffman: Yeah. No, this has been a pleasure. What a great, great time I've had. Thank you so much. What an insightful discussion. I those are some new questions I haven't really had before. So, uh, you really got to the core of everything there. So thank you so much.

00:27:46 Sana: Thank you. Thank you so much for, for, uh, sharing those words and listeners. I mean, yes, if you find yourself drawn to conversations like this one, the ones that don't rush to conclusions do follow this blend. Do connect with Eric, check out his book. He's behind you. And of course, of course. Take care. This is your host, Sana. I'll catch you in the next episode of this blend. Thank you.