Web exclusive: Attorney building new business to help solo firms succeed

Jason Massaro

Jason Massaro has been a practicing lawyer for nearly 30 years and now he is launching a new consulting business targeted at helping small solo firms. 

Indiana Lawyer talked to Massaro about his experiences as a lawyer and what he hopes to accomplish with his consulting business, The Office Down the Hall.

What is your law background?

I essentially had kind of almost two careers…when I got out of law school in ‘96, I went to Valparaiso [Law School], and I practiced for about the first 10 years up in the Region. I did primarily insurance defense work on more complex cases on the insurance defense side.

I did that for about 10 years, and I just kind of wanted to do something different and a little bit maybe more challenging and complex. I’m originally from Chicago.I didn’t want to go back there. I looked around and Indy seemed to be a good market, and believe it or not, it was still kind of growing back then and was not nearly what it is today. So, I interviewed with several firms downtown and got in one, [but] it no longer exists. 

I was tasked with kind of finding, “Do I go into another law firm, or do I start my own?” And when it didn’t look like things were going to turn around, I decided to kind of venture out, which was extremely scary. So, I started about the latter part of 2010/2011, with [a] very, very small office.

It was really difficult because I didn’t have any clients. It was kind of one of those things where the clients that I did work on were either devoted to the other lawyers at the firm, or they went out of business, or I wasn’t really kind of allowed to take them anywhere. And so, I really had to learn a lot of things that were different than any practice I had before.

I was the litigator down the hall… So when I started my own firm, all of that was new. I didn’t know anything about SEO or websites or anything.

Tell me about your new venture with The Office Down the Hall?

The background of the name is kind of interesting, because I’ve had numerous lawyers who practice in mid- or large-sized firms, and they’re just like, “I could never be a smaller solo because I just cannot see losing that resource, to go down the hall to another office, another lawyer, and collaborate with him or her on a particular issue I may have…I would just lose that if I was a small solo.”

And there is definite validity to that, and I had to deal with that [when] starting. So what we want to do with this new firm is provide that resource for those individuals who have, for whatever reason, chosen to be a small or solo or kind of what I call a burgeoning firm, where maybe other lawyers have come together because they wanted to shift their focus a little bit. 

We wanted to be that source where people could confidentially and comfortably reach out to someone who could either help them in an aspect of the litigation or be a side-by-side collaborator for the entirety of litigation or come in and look at their business practices.

Lawyers went to law school to be lawyers, not necessarily businesspeople. And I don’t know that they necessarily know that those things are lacking. We want to help them. 

How has the mentoring you’ve experienced influenced your pivot from running a solo practice to running a legal consulting business?

The mindset becomes, for every second that I’m not working on a client’s matter, I’m not making money… but the mentoring lacks because of that mindset. It costs a lot of money to mentor people.

That’s (mentoring) such an important need. It’s something that I realized when I started practicing. So, we’re there to offer that as well.

So far, what has the process been like while transitioning from private practice to legal consulting?

We’re not quite up and running yet, we’re looking at probably mid Q1, of 2025. 

So, we had decided to retire at the end of 2023 and I had a handful of clients…we kind of kept those on. And as things kind of slowed down, I realized that while I could stop, I just kind of felt this urge to continue on, but in a different methodology — still in the practice of law, but not necessarily keeping on with all the rigors of litigation, but really kind of  changing my focus to helping other lawyers.

You talked about how scary the transition was from working at a law firm to opening your own solo practice. How has doing that given you the confidence to pursue this new business that is different from what you’ve done before?

I’m an extraordinarily competitive person and failure just kind of isn’t an option for me. I mean, I’ll just work as hard as it takes. I just don’t quit. I’ll find the resources. I’m very resourceful. I make relationships well. I understand when I need help. I’m not afraid to ask for it, and I like a challenge. 

This is by no means easy, and I have no way of knowing whether it will succeed. I believe it will, but I just draw on my prior experience with starting the firm.

Like I said, I didn’t have any idea about so many other aspects of the practice of law. I knew business, I understood its concepts, but starting my own firm was a completely different animal. I just had to kind of learn as I go.

What do you hope to accomplish in the first year?

For 2025, I would like to have at least five to 10 law firms that I can say we really helped turn it around for them.

What do you want to say to those on the fence about seeking legal consulting to make them understand the importance of it?

The first thing I see with a lot of lawyers, and especially since they’re generally, in the litigation sense, so competitive, [is] that it’s okay to ask for help. 

And the second thing is, you’re a business, and you have to invest money in your business. It takes money to make money.

I think if you can reconcile those two issues, looking at how a consulting firm can assist your practice, legally or business wise, will kind of bring it home.

Clients interested in working with The Office Down the Hall can contact Massaro at [email protected] and visit his website at http://www.odhlegalconsulting.com.