Transitioning Out Of The Law To Legal Marketing With Andy Cabasso [TFLP 130]

Today, I’m sharing my conversation with Andy Cabasso. Andy is a former lawyer and startup founder that began by starting a legal marketing business in law school with a former college roommate. 

He ultimately ended up moving into that full-time and selling that business and starting another one. We’re going to be talking about Andy’s transition out of the law and into legal marketing, and startup creation. 

And as always, we’ll have some tips for you if you’re thinking about leaving the law. So without further ado, let’s get into my conversation with Andy Cabasso.  

About Andy Cabasso

In 2008-2009, Andy was in his last year of undergrad, studying business. This was at the same time as the great recession, so it’s safe to say his next steps weren’t clear. As he was shifting, he was advised to go to law school by some mentors.  

Even though Andy said he would tell his past self not to go to law school, he did quite well. But, during his second year, he realized that this path wasn’t for him. At the time, he wasn’t able to articulate it, but he was disillusioned by the many things, including the billable hour model. 

Moving Out Of The Law and Into Legal Marketing

Andy saw his path out of the law while applying to work at different firms. The websites he looked at were terrible, and he saw a common mistake among all of them. These firms weren’t connecting their content to their target audience.  

He joined forces with his roommate, a freelance web designer, to start a side-hustle. Through Andy’s experience, they found a huge opportunity in web design and online marketing for lawyers. 

Andy graduated from law school and started practicing. But after a while, his side hustle grew and became a full-fledged business. So, he moved out of the law and focused on his legal marketing agency full-time.

The Acquisition Of The Agency

As the business grew, Andy formed partnerships with other companies in the legal space. One day, one of those companies approached Andy and his partner and proposed acquiring their business. It would be a win-win for everyone involved, so after negotiating, the agency was sold.  

After selling the agency, Andy stayed on for a few years. They liked his marketing so much, they wanted him to stay on and do their marketing on top of running his former agency. So, he did that for a few years until his contract was up.  

The Birth of Postaga 

After leaving his former agency, Andy started working on a few other businesses. While tossing around ideas with his partner, one thing they saw was the effectiveness of quality link building for legal marketing. 

The way it works is that if you get enough links from relevant websites, your site will rank better on Google. But this can be a very manual and labor-intensive process, so they sought to streamline and automate the tedious parts of it.

This became Postaga, which Adam and his partner founded and launched in May of 2020. They launched on Product Hunt, where they were very successful. The day it launched, Postaga became the #1 Product Of The Day. This success brought in a lot of investors and publicity.

From there, Andy and his partner continued to build Postaga. And last year, they joined a startup accelerator program where they have been working on it ever since.  

Time To Start Transitioning Out Of The Law? Here’s Some Advice:

A common problem with my clients is the belief that they don’t have any transferrable skills to work out of the law. This feeling is a part of the whole sunk cost concept. Most people looking to leave the law feel that all the time and money has been wasted. 

However, Andy reflected that his time in law school gave him many beneficial skills, like writing and analytical thinking. As a lawyer, you likely have these skills too. The skillset you develop in law school can be extremely helpful out of the law. 

But if you’re unhappy and you need to make a transition, you can’t view it as a bad investment. Andy says to think of it as an investment to yourself instead. All that time and money went into a skill set and experiences that can help you move forward.  

He invited my listeners and readers to reach out for any advice on transitioning. You can also check out Postaga for their cold email, link building, and other services. With the code podcast50, you can get three months for 50% off! 

And if you haven’t yet, I highly suggest downloading my free guide, First Steps To Leaving The Law. Until next time!

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Sarah Cottrell: Hi, and welcome to The Former Lawyer Podcast. I'm your host, Sarah Cottrell. I practiced law for 10 years and now I help unhappy lawyers ditch their soul-sucking jobs. On this show, I share advice and strategies for aspiring former lawyers, and interviews with former lawyers who have left the law behind to find careers and lives that they love.

Today on the podcast, I'm sharing my conversation with Andy Cabasso. Andy started a business in law school with a former college roommate and ultimately, when he graduated from law school, while he started practicing law, he ended up moving into that business full-time, then selling that business and starting another one. That is what we're going to be talking about on the podcast today. Let's get right into this conversation.

Hey, Andy, welcome to The Former Lawyer Podcast.

Andy Cabasso: Hey, Sarah. Thanks for having me.

Sarah Cottrell: I am really excited for you to share your story. Can you start with introducing yourself to the listeners?

Andy Cabasso: Sure. My name is Andy Cabasso from New York. Back in the day, I went to law school, graduated, started practicing law, then found a path that diverged from that and ended up starting my own business, grew it, sold it and now, I'm on startup number two right now.

Sarah Cottrell: Let's talk a little bit about why you decided to go to law school in the first place.

Andy Cabasso: I was in undergrad in my last year and it was 2008, 2009 as the great recession was happening and I had studied business in undergrad, and I was not really sure what my next steps forward would be. At the time, I was studying film production and video production, and I had worked at a few TV stations, then realized that wasn't for me. I was enjoying filmmaking and enjoying working on the TV stations, and everything like that but I didn't want it to be my career. As I was shifting and thinking what I would do next or what I would try out, some of my mentors were advising me to go to law school.

I was studying business and I was thinking, “Maybe I would start a business someday, but I have no idea what I would do exactly.” The job prospects were looking really, really bleak. I know in hindsight, with the knowledge I have today, I would probably have told myself, “You know, don't go to law school. Don't take on that debt, just because you're not 100% sure what to do next.” But that was me. I did well in school, took the LSAT, did reasonably well on those, then got into and went to Fordham Law.

Probably, during my second year, after I did an internship over the summer and was starting to get into the clinics, and everything like that and more stuff that was closer to real legal work, I was realizing that this path probably wasn't for me. In particular, I couldn't super articulate it so well at the time, but there was something that if I were to go practice at a firm or at a large firm, like so many of my classmates and I were looking to, we would be beholding to this billable hour. Hour work would be measured in tenths of an hour and just by the amount of labor we were putting into our work, and not at all really feeling like being productive, or being efficient felt like it wouldn't be as valued.

Over the summer, through my legal internship I had, they brought in consultants from some investment bank and they were teaching us like Excel hacks, and shortcuts for Excel because they were saying like, “You know, when we're at this investment bank and everything like that, time is money and we need to know these keyboard shortcuts. This way, we get out of the office at 10:00 PM instead of 2:00 AM.” It's like, “Oh wow.” But at the same time, I was like, “Well, even if I am more efficient, that doesn't do better for the firm because that's less hours that I am billing for the client.” Me, wanting potentially just to be the most productive I could be, if I could streamline and automate the tedious parts of my job, that would not really be rewarded. I was a little disenchanted with that.

Sarah Cottrell: So many things. First of all, 100% the billable hour is one of the chief nemesis of The Former Lawyer Podcast. My experience was very similar because in fact, one of my strengths in general is my ability to work quickly. When I graduated and started at a law firm, it very quickly became apparent to me like, “This is actually not an asset,” then it just reveals how questionable the entire system is because the incentives to perform better just don't exist. Anyway, 100%, I totally hear you on that, but even to go all the way back to, so I laughed when you said 2009 because I graduated from law school in 2008, so a different stage but going out into a similar situation for many people. My class coming out of law school was the last one to experience the typical hiring, like my summer class at the firm where I summered at, my 2L summer had a hundred summer associates.

Andy Cabasso: Oh, that was frustrating too. In law school, at the job fairs and everything, they would have recent graduates come and talk about working at, I remember, someone was like, “Oh yeah, I was at Proskauer here in New York. They rented out Madison Square Garden one night for all the interns, so we played basketball on the court that the Knicks play at. I graduated in ‘06 or whatever.” I'm like, “Yeah, a cool story bro.”

Sarah Cottrell: You’re like, “Welcome to not my life.”

Andy Cabasso: But they're not hiring anyone this summer. It seems like the law school has forced OCI, even though firms are going to bring on one or two total summer associates because the school is making them. Otherwise, they don't get to come back and do OCI again next year, and have access to the pool of students.

Sarah Cottrell: It was a very grim time all around. It sounds like when you went to law school, you said mentors were giving you advice to go to law school and it sounds like, and you can correct me if I'm wrong, but the experience that a lot of people have where they're getting to the end of their undergrad career, they aren't really sure exactly what they want to do, law is seen as a good path generically for people who don't know what they want to do and don't want to be a doctor, so a lot of people get put on that path by, in many times, very well-meaning people.

Andy Cabasso: People who are also not practicing lawyers though. They're like, “You're smart, you should go to law school.” With the meritocracy that is undergrad and like, “You do well and you get good grades,” the extension of that seems to be like law school for a lot of people. I felt like that was the case for a lot of my classmates too who all did well in undergrad but didn't know what to do next and it seemed like this was the next right thing to do.

Sarah Cottrell: People advised you to go to law school and you ended up doing that, so by the time you got there, were you in a headspace of like, “Maybe I want to practice law, maybe I don't. I just want to do businessy things. I think law may fit into that in some amorphous way that I can't totally articulate,” or had you convinced yourself or decided like, “Oh, I want to practice law. Being a lawyer is my path”? Does that make sense?

Andy Cabasso: Yeah. I was open-ended really, I was like, “All right, I think I want to be doing business afterwards.” But maybe in hindsight, I would just tell myself, “Work at a firm as a paralegal or something for a while and see if this is really something that interests you. Don't just take on debt to see if this would be a good way forward.” But anyway, I was open to different possibilities and seeing things like, “Would there be a career forward in law that would work with what I wanted to get out of a career?”

Sarah Cottrell: As we've already talked about the period of time where you were in law school, then coming up to graduating from law school was just a very grim time, especially for people graduating from law school, talk to me a little bit about by the time you got to the end of your three years, what were you thinking about your potential career in law? Did you have a plan? Were you still like, “I just need to find a job.” What was your thinking?

Andy Cabasso: I saw a path forward that came about in law school because when I was applying to work at different law firms, I would go to their websites and check them out, look at their about us pages and all of that, and most every firm I was looking to apply to had a terrible, terrible website. Reviewing hundreds of law firm websites, I was seeing the same mistakes they were making every single time, whether it was these sites that were just meant to be a resume or business card for the lawyer or the main attorneys of the firm or if it was like a larger firm, just seeming really disconnected from their clients and target audience.

I was thinking, “I could do something about this. I have a business background. I'm not a web designer but I could help lawyers market themselves better online,” because I saw a lot of opportunities there. My roommate from freshman year of college at this time was doing freelance web design work and we started talking about working together. I found this market that I saw had a huge opportunity and that I thought, “We could do web design and online marketing for law firms.” This started out as a side project. I graduated law school, I found work and was practicing but what started as a side project of doing marketing for lawyers became a business. Because we were doing a good job marketing ourselves, we grew and this became clear that it was a full-time job. I quit practicing and ran, and grew, then eventually sold this successful agency, focusing on legal marketing.

Sarah Cottrell: Let's talk a little bit about, so you said you did start practicing, ultimately, you ended up quitting to work in the business full-time, so when you started practicing, because you said the business grew organically, so when you started practicing at that point, was it at the point where you already saw the possibility that if it continued to grow, you would be leaving the practice or at that point, were you still like, “Okay, I have this thing, which is an opportunity but also I'm practicing law”? Does that make sense?

Andy Cabasso: I was very hopeful. I really wanted it to be successful. I was putting as much time and effort as I could into making it successful because at that point, I didn't see myself enjoying a career practicing law, at least, where I was. I was putting all my effort into making the best possible that this marketing agency that I'd started would be successful.

Sarah Cottrell: Tell me a little bit more about why you didn't see yourself practicing. Is it primarily what we talked about before, the issue of this billable hour model makes no dang sense or were there other pieces to it as well?

Andy Cabasso: There are I guess a bunch of other things. Like the things that I enjoyed most in law school, I probably most enjoyed a moot court class I did, mock trials, and everything like that. I had a lot of fun cross-examining witnesses and preparing opening statements, and all of that, but the night before I would have to do any of these exercises in class, I'd be stressed out and anxious. It was very low stakes. It's for class. I was talking with the professor who's a practicing trial lawyer. He was like, “Yeah, I'm stressed out constantly. I have to go in front of a judge, juries, and opposing counsel and I have to make sure that I put forth the best arguments I can, and a lot of just thinking on my feet to do the best I can for my clients.”

Being the thing I was enjoying most, that was also stressing me out. I don't think that was for me. In terms of transactional work, I took some business-oriented classes as well and I did some legal internships at organizations. One thing that was a little disheartening was that doing deal side stuff or working for business or for clients, you are helping other people grow their businesses. I was more envious of those people running the businesses in those roles that was where I wanted to be, that was where all the action is, not in drafting and reviewing agreements. I probably would have been terrible at transactional law. I couldn't bring myself to get through these dense contracts and things like that. It just wasn't for me either.

Sarah Cottrell: I've heard that from so many people, especially people who have been practicing at a law firm, then move in house because, like what you said, they want to be closer to the business side of things. The reality is that even if you're in a business, if you are the lawyer—you're still the lawyer—it depends on the different companies and how they divide the roles, but many people have shared to me this experience of where they have actually gone and worked in a role like that, thinking it would get them closer to the business side and realizing like, “Oh no, I actually have to go to the business side if I want to be on the business side.”

Andy Cabasso: The problem I felt was being an in-house counselor or something like that, that is not a fun role to be in because you are really the backstop to a lot of the things that the business wants to do. Like the CEO and the founder or something that say, “All right, I want to do this or have this product or do this. Can we do this?” The lawyer has to be like, “Okay, you can do this but here's what you need to look out for or here's what you need to avoid.” It didn't really feel like it was so collaborative or creating solutions but it was like, “Here's what someone else wants to do. Here's how I can best help them to do that.” But yeah, it just felt like a backstop situation.

Sarah Cottrell: For sure. Talk to me a little bit about the nuts and bolts of building that company, that original company that you built with, I think you said, your freshman year roommate.

Andy Cabasso: Yes, that was really lucky that I had this business partner who I get along with, that I've been working with to this day, who had this background that was necessary for what I wanted to do, and was game to work with me. Building this agency, some of it was definitely like learning on the job. I wouldn't say that I was the most skilled marketer the day that I started but I was definitely much more in tuned and aware than the firms that I was working with, so I could offer advice from the perspective of someone with legal background who understood their market a little bit but also understood design aesthetics and general marketing concepts because I was also finding that in particular, a lot of the firms that didn't have a great web presence were not as mindful about important marketing concepts, just from the very basic perspective of, “Well, what's the point of your law firm's website? Because I go to your firm's website, I can't access it so easily on my mobile phone. There's not a lot of information on the site itself. What is this for?” I could speak the language of our clients very well.

I also did a lot of blogging and content marketing, creating articles for helping lawyers to better understand marketing their websites. That was a big source of leads for us over time because—and this is probably before I had the understanding of SEO and digital marketing that I do today—which was that I was writing content, just based on conversations that I was having with lawyers. The questions that they were giving me, I was just turning into blog posts. I figured that they would be searching for these things online, and they were, and that drove a ton of traffic and got us a bunch of clients.

I remember early on, I wrote some blog articles about different legal software, like Clio, MyCase, and Rocket Matter and reviewing those, that got us a ton of traffic because other lawyers were searching for that. I figured lawyers who would be searching for practice management software were at an inflection point in their business where they were either starting up the business or they were looking to add on new technology and hopefully, at the same time, maybe they'd be considering building out their firm's web presence as well. Doing that marketing really helped us but one important lesson that I got from that, that I would also just tell our clients constantly, was that when you were creating content, whether you're blogging or creating any other content for your website, the most important thing about the stuff that you're writing is not your writing style but writing for that audience.

I could write blog articles for lawyers using legalese, legal terms, and things like that because they were my audience but lawyers couldn't drop Latin in their bios or their helpful articles about what to do if you get arrested or anything like that because their client base aren't lawyers. They don't know anything about statutes or anything like that, so the content that they were creating needed to be geared toward that audience so I could help them understand that perspective and make their content and their website more accessible.

Sarah Cottrell: Their clientele are Googling things like divorce lawyers near me, not like, “What are the standards of review of a blah-blah-blah.”

Andy Cabasso: Sure. A great example of that is in New York, divorce law is often called matrimony law, a matrimony lawyer. No non-lawyer ever used the term matrimony law. No one searches for a matrimony lawyer. They'll either search for a divorce lawyer most likely or maybe a family lawyer. For marketing, a lot of it was just tweaking the messaging and making sure it was accessible to the people that you wanted to reach with the site. For law firms that weren't geared towards consumers, like people hiring divorce lawyers or injury lawyers or anything like that, firms that were more geared towards corporate clients, they also needed to make it so their content was accessible to those clients.

What are they coming to the law firm's website for? They want to know that the law firm has experience in the esoteric things that this client wants. If we're talking like corporate law, some M&A transaction, something that looks identical to what the client's matter is. The client wants to see that this firm has that experience. Just broadly saying on a web page, “We handle M&A transactions, licensing, or intellectual property,” just broadly, that's not going to be reassuring to a client who is referred to this particular firm.

Sarah Cottrell: Let's talk a little bit about, in terms of the agency, were you—well, I guess your business partner—were you doing the whole gamut, like building websites, content marketing, SEO, all of those things or were you just doing certain pieces of it? How did that work?

Andy Cabasso: We started out just doing web design and that was all we did. Then over time, we added on additional services when we were comfortable that we would be able to deliver well on them. We started out doing a pilot project with one client to do paid ads. Some of it was like a learning experience for us but we were really trying to make it as low stakes as possible, nothing like super high budgets or things like that. We worked with some other consultants as well to make sure that we'd be able to do this right. Once we were able to deliver for the client and we were all happy with our processes and workflows, we started offering those services as well.

The same thing went for SEO. At first, we outsourced our SEO to another agency, then over time, as we thought we could do a better job in the agency we were outsourcing to, we brought that in-house and we built the systems. Really the most important takeaways from building this business were having repeatable processes, having documentation for everything so if we needed to, when we’re hiring people, we could onboard them quickly and they could know exactly what they needed to do. Even if they've never done super similar work, we would have this workflow for every single client project. Whatever their different types of projects were, we'd have a workflow specifically for SEO that was repeatable.

This way, it would also make sure that the business could be scalable. As we would take on more clients, nothing would fall through the cracks because we built these processes and systems in-house. With that also, I was working towards trying to make it so if I had these systems in place, we have things to be accountable to. The dream is to be able to have this business running fairly streamlined with my team, so I wouldn't need to be working in the business every single day. I could be working on the big picture things for relatively growing the business and not working on site designs, revisions, or client work or things like that.

Sarah Cottrell: Talk to me about the acquisition. When you started the company with your business partner, was it always with an eye towards being acquired eventually or is that something that bubbled up over time?

Andy Cabasso: I will say everything, it was part luck, part right place, right time. I'm not going to say here that I was some brilliant mastermind and that I knew that this would happen. I had no idea that we would be acquired in a relatively short period of time, but we had a lot of the right pieces in place. We've built up a business that had recurring revenue, so we had this asset that could be sold, we've built up our brand in the legal industry, and we had formed partnerships with other companies in the legal space. Because we were doing a lot of marketing and we were building partnerships with other legal tech firms to refer business back and forth when we could, so we had a lot of mutual clients with other legal tech related companies.

One day, one of the companies approached us and said, “We're looking to get into the legal marketing space. Are you interested in being acquired? We would bring your company on to ours. We have a lot of mutual clients, so this would be a win-win for everyone in that your company would get exposure to our audience, ours would get exposure to yours. There's a lot of cross-selling opportunities here. We could grow both businesses faster.” That was their perspective. It made sense to us. After negotiating everything like that, it all worked out.

Sarah Cottrell: So you started the business in '07-ish, I guess when you were in law school still, is that right?

Andy Cabasso: I was in law school starting in '09.

Sarah Cottrell: Oh, right. Sorry.

Andy Cabasso: I was in law school starting '09. This became a real business, like we incorporated and everything like that in 2013, and we were then acquired in 2016.

Sarah Cottrell: Oh yeah, that is fast. I know we talked about this a little bit before we started recording but one of the things that I hear from people all the time—and this was an experience I had myself—is you go to law school, then you often get in this head space of like, “Well, all I'm qualified to do is lawyer things,” which I know you and I both agree that is not actually true. There are many things that you can do with the skills that you develop in law school. Can you talk a little bit about that and how you saw that play out in your experience of building, then selling this company?

Andy Cabasso: Sure. I guess there's a lot I feel like I could talk about with this but a few things in particular. One, going to law school and having this legal background helped in terms of creating a business that was focusing on the legal market. In building this business, I was introduced to a lot of other businesses that were catered to the legal market. Most of the people at these businesses had a legal background. They either were in big law, then saw a problem and started this company or something like that. That was a very common path that we saw. But for people with an entrepreneurial event, having a background in law, if you want to have a product or business that serves lawyers, you can speak very well to that market. I can just say from experience of having myself and also a team of salespeople, the clients always liked talking to me, just by virtue of me having a law background. That was a very strong selling point.

Our clients could relate to me or thought I could relate to them better by having that legal background. Even if I wasn't the best salesperson on the team and I don't know that I knew so much more than any of my colleagues about running a law firm, especially years out and as like the other people on my team had been working with clients just as much as I had, but that definitely was a plus. Beyond that also, some of our marketing I did, I gave CLEs. I could present in New York, I could present CLEs because I am a licensed lawyer. Being able to do CLEs and speak to other lawyers as our target market, that was super helpful and validating as well. That was really something good to have there.

But I would say that if you're looking to get out of the legal industry and not do something that serves the legal market or lawyers, there were definitely some skills I'd say that I picked up from law that were useful otherwise. I don't want to be too arrogant here but I'm very confident in my writing abilities, not just legal writing or anything like that, but just my writing skills in general. I saw that I could create copy and content that's coherent, and also just much quicker than a lot of my colleagues. If I'm creating a blog post, which is very different from drafting a contract or brief or anything like that, I found that a lot of the skills associated with just organizing your thoughts, crafting your arguments, seem to just naturally translate pretty well. Maybe it wouldn't if you're just thinking about it like, “Really?” But I found that it was super transferable.

Then there's just the analytical aspect of being able to pick certain ideas apart, to have an analytical mind to, when you're dealing with new concepts, looking for the holes, looking for the weaknesses, looking for the strengths, which is also helpful for entrepreneurship in terms of vetting new ideas or things like that. I'd say that was probably an underrated thing that I don't think about every day but it's there. I'd say if today, let's say I had graduated law school, I'd been practicing for a while, and I was looking to get out of practicing law, I might be concerned like, “Well, I've got these years on my resume of having practiced law. If I'm looking to get into something else, who's going to want to hire me or what can I offer?”

I find that having the mind that law school develops is very useful in a lot of different settings. But making the transition to a different career, you're starting from scratch going from being a practicing lawyer to something completely new in a different industry, that's going to be just like entry level at any other industry or space but you have this thing on your resume now that is a very good advantage to have in a lot of different career paths.

Sarah Cottrell: I think to your point, a big part of it is learning how to see your skills as transferable so that you can then articulate to other people, other companies, and other businesses why your skills would be a good fit, which like you said, there's so many things, like for example, the writing piece, the analysis piece, especially if you're someone who works with all lawyers, you often don't really see those as strengths because those are the skills that everyone around you are developing and using. But when you go into other environments, you realize, “Oh, these are actually skills that are useful.” There tends to be the sense amongst lawyers of like, “Well, everyone is like this.” It's like, “No, actually, that's not true.”

Andy Cabasso: In the past few years in particular, some people have reached out to me on LinkedIn saying like, “I'm looking to make a transition. I don't want to be practicing law anymore but I've been practicing for years. How do I make the transition? I feel like I have these skills that are just not useful to other businesses.” But if you're starting from scratch in a new space, I'd say the skills that you have can absolutely be useful now. You may not have specific experience with coding or marketing or anything like that, but you've demonstrated that you have some writing and analytical skills that can be useful in a new career path. But just like you don't have experience in this line of work, you're going to have to start from the bottom in terms of getting relevant experience to go up in that career. It's just starting all over again from the bottom of the ladder.

Sarah Cottrell: 100%. This is something that I talk about with the lawyers in my program all the time. It really does become a question of like, “Okay, really, what do you want to do?” It's not so much a question of being able to position yourself for it. It's knowing what it is that you want to position yourself for. Five years ago, you sold your first company and I know that you founded another company. Talk to me about the last five years and this new company.

Andy Cabasso: Sure. After I sold the agency, I stayed on for a few years. They liked our marketing so much, they wanted me to stay on and do marketing for the whole company, as well as run our agency as well, so I did that for a few years, then after our contract was up, I started working on a few other businesses. One of them in particular started from my experience with the agency that I had. I was just with my co-founder, we were tossing around ideas and one that we had was that when we were marketing for ourselves, and for our clients, one thing that we saw was that a very particularly effective marketing strategy for helping your site rank better in search was the quantity and quality of other websites linking to your site.

For example, if The New York Times links to your business's website, your business website is going to show up better in search results for a lot of different keywords related to your business because that link from The New York Times tells Google that your site is relevant and of good quality. What a lot of people in the SEO space try to do is they do a lot of manual outreach to other sites to say to them, “Hey, I saw that your blog covers this topic and you've got this great article. I've got a blog article myself that I think dovetails yours nicely. Could you do me a solo and link to my article and yours?” If you get enough links from relevant real websites, your site will rank better. But the problem is that processes can be very manual and labor intensive, so not being one to enjoy manual labor intensive processes, we sought to streamline and automate the tedious parts of it.

That became Postaga, which we built. We launched it officially in May of 2020. We launched on this site called Product Hunt, which is for new startups and products. We were very successful on our launch there. We became the number one product of the day when we launched and we got a bunch of investors reaching out to us from that. We got a bunch of publicity, which was really great. Then from there, we continued to work on the business, we joined a startup accelerator program last year and have been working on this ever since.

Sarah Cottrell: That's super cool. I'm going to restrain myself from nerding out about SEO but yeah, SEO is really interesting, and for me, has been a huge for Former Lawyer because there are lots of lawyers who, like me, back when I was in Biglaw and miserable, go to Google and search for alternative careers for lawyers like, “What can I do that isn't being a lawyer? or “I hate being a lawyer.”

Andy Cabasso: Oh, I got that book. There was a book called What Can You Do with a Law Degree? that I got while I was in law school. I was like, “This is maybe a little bit late.” I felt like the book was also a little bit dated.

Sarah Cottrell: It's interesting. I think one of the things that your story illustrates really well is that when people are thinking about doing something else after they've graduated from law school, often, they see their options as very limited like, “Okay, if I don't want to be a lawyer, then my options are compliance and a couple other things that are very legal adjacent.” Yes, the original business that you built was obviously serving clients in the legal space but in terms of the skills, I think it's really helpful for people to hear that you don't have to be that limited in the way that you think about what your options might be.

Andy Cabasso: At the time when I was graduating, I didn't really see any other lawyers that were pivoting and doing marketing that I was looking up to in particular. But one thing that I had seen during one of the career day sort of fair things, there was a person who started a mobile game development company. I think he had started at a big firm, like Proskauer or something like that. I don't know why that one's in my head in particular, I mentioned it twice but he started at a big firm and he left to start a mobile gaming company called Astro Ape. His name was Chieh Huang. His mobile app gaming company got acquired by a company called Zynga, which is a much larger mobile gaming company. I think recently, Zynga just got acquired by another larger company. I don't know if it was Rockstar Games or something like that, a major, major, major gaming company.

That's his experience with first starting a mobile gaming company, then after that, he started a company called Boxed I believe. He runs this company that is basically groceries and household items delivered to your door, like Costco but over the internet. He came to our career day panel and I was just in awe. I'm like, “Well, you started a business and you're working on your next business, tell me how you got out and why?” He's like, “I was just tired practicing law. I want to do something different and I had this opportunity with these friends, and we went for it.” That was hugely motivating for me in particular.

Sarah Cottrell: I think it is really helpful, like you said, to see what's possible.

Andy Cabasso: For sure. Being able to see that someone else has done it, that someone else has gone through law school or practicing, then found an alternative path, it may not have seemed super possible. I'm like, “Well, what transitions have people made successfully or what have they done?” Having that example was super helpful. I try and be helpful whenever I can. If anyone hits me up on LinkedIn or Twitter, if they have questions about transitioning or starting a business or getting into marketing or anything like that, I'm happy to offer whatever advice I can or if you want to build a business or get into a business that serves the legal space, that also could be an option as well. I'm happy to help when I can.

Sarah Cottrell: That's great. Andy, as we're getting to the end of our conversation, is there anything else from your story or any advice that you would like to share that we haven't had a chance to talk about yet?

Andy Cabasso: I'd say one thing in particular is I feel like going to law school and during it, down a certain career path, there is this sunk cost feeling that I've invested all this time and money into practicing. If I'm going to change career paths, I'm starting at the bottom, effectively, I've wasted all this time, effort, and money that I've spent. But if you're unhappy practicing and you need to make a transition, if it's right for you, if you're ready, if you need to make a transition, then you can't really view it as this past investment that you've made. If anything, you've invested in yourself. You have an increased skill set now and you have increased experience.

Now, not everything may translate super 100% well to your new career path but you have this skill set. You are who you are today because of the experiences that you have. You can use what you've gained from your past experiences moving forward. But if you're unhappy with where you're at, just viewing this as saying, “Well, I have this investment that I put in, I have this time that I put in,” I don't think that you are stuck and I don't think that you should view yourself as just having the sunk cost, having this investment that you can't do anything else.

Sarah Cottrell: I think that's really helpful. One of the things I talk with my clients about all the time is this idea of like there actually are costs that cut both ways. Yes, there are sunk costs but there also is the cost of continuing to do the thing that isn't really the thing for you. You could have graduated from law school and been like, “Well, I graduated from law school and that's a sunk cost, so this business, it's cool but I'm a lawyer now,” and that would have been an option but the cost to that would have been not building that first company, not being in the position now to build this company that you're building now. I think that's also a really important thing for people to think about when they're thinking about the issue of sunk costs. It's like there are more costs than just the sunk costs.

Andy Cabasso: Sure, absolutely. There's the cost of moving forward. Are you going to find satisfaction doing what you're doing, moving forward? Are you stressed out? Are you burnt out? Very much the mental health and substance abuse issues are just rampant in this space. If you're suffering from any of that, is continuing on this path right for you or worth it to you for the future of where you'd be if you continue on this path?

Sarah Cottrell: Literally could not agree more. Andy, where can people find you and your company online?

Andy Cabasso: I'm pretty easy to find online. I don't think there are any other Andy Cabasso out there. On Twitter, I'm at @andycabasso, on LinkedIn I'm Andrew Cabasso. My website is Our platform that we built helps with cold email outreach, for link building, PR, and sales. If you want to check it out, if for any reason, this is relevant for your business or something you're looking to do, a coupon code podcast50 will get you three months at 50% off. Feel free to hit me up if you have any questions about transitioning, getting out of the practice or just if you want to brainstorm what could be right for you, I'm happy to help.

Sarah Cottrell: Awesome. Thank you so much, Andy, for sharing your story today.

Andy Cabasso: Thanks, Sarah. This was fun.

Sarah Cottrell: Thanks so much for listening. I absolutely love getting to share this podcast with you. If you haven't yet, I invite you to download my free guide: First Steps to Leaving the Law at Until next time, have a great week.