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Steven Leahy’s Framework for Proactive Business Owners Building a Tax-Resilient Business

Principal Attorney at the Law Office of Steven A. Leahy, PC

In this episode of Wytpod, Stephen Bland interviews Steven Leahy, a tax attorney and founder of the Chicago Tax Team. Steven shares his journey from law school to building a successful tax resolution business. He discusses how IRS problems are often symptoms of deeper issues like poor bookkeeping and how his firm adopts a holistic approach to resolving them. Steven outlines his five-step process for helping business owners stay compliant and introduces a subscription model to provide ongoing support. The discussion also covers his thoughts on the future of legal services and advice for aspiring attorneys.

The Law Office of Steven A. Leahy, PC or Chicago Tax Team is a legal firm specialising in helping business owners resolve IRS problems through a comprehensive five-step program.

Steven Leahy
Principal Attorney at the Law Office of Steven A. Leahy, PC

Hello and welcome to the latest Wytpod. I’m Stephen Bland, your host with Wytlabs, a full service marketing agency. Today’s guest is Steven. Steven, feel free to introduce yourself and let our viewers know about your background.

Sure, my name is Steven Leahy. I’m an attorney. I help business owners solve IRS problems. And actually, I think we have a whole new way of looking at taxes and business. And that’s kind of what we help people do.

Awesome. What inspired you to become an attorney? Go ahead.

That’s a long story. I think really what I wanted to do was run my own business and I already had a business degree. So everybody told me, well, you don’t need an MBA. You should probably get a law degree. So I went to law school thinking I was going to start my own business. And I did start my own business, but it was a legal business.

Awesome, awesome. So who is the ideal target audience for your firm now?

We help business owners, mostly with tax trouble, but actually we help business owners who aren’t in tax trouble who want to avoid it. But most of my businesses, how we began is starting people helping business owners who have tax problems. And then what I learned was that many people, companies who have tax problems, tax problems is just a symptom. The real problem turns out to be bookkeeping and other issues like that.

And so if you solve the tax problem without solving the accounting problems, you’re just gonna go right back to what you were doing before and having problems. And so my goal is to help business owners solve their tax problems forever.

Also, in what areas are you servicing?

We help people mostly in the Chicagoland area, but actually I can help people all over the country with tax problems.

Okay.

Guy, you say you do anything in the US for tax problems? All right, here’s a good question for you. What makes you different than your competitors?

Pretty much, yes.

Again, we take a holistic approach. I think there’s a lot of people, again, who want to fix your tax problem, but they’re not really fixing the problem. So I think a lot of business owners don’t really think about taxes until it’s too late. I always tell, know, the IRS has always been a silent partner in your business, but they’re silent no longer, right? They’re very active now. And more and more, you’re going to have interactions with the IRS.

And so you need some plan to address that. And I think that’s what makes us different than an accounting firm or a tax resolution firm, because we take that holistic approach and try to solve not only your tax problems, actually we have a five -step program. So first, we want to solve the problem that you have. That’s important. Second thing, you have to look at your business structure. Too many people are sole proprietors.

Or for instance, I help a lot of realtors who are 1099, right? And they don’t look at themselves as business owners, but they are. So you have to look at your business structure. Third thing you gotta do is you gotta look at your accounting system. As I mentioned, you can’t really, you have to have a good accounting system these days in order to avoid IRS problems. Fourth thing, once you do all of those three things, now you can talk about tax planning and trying to reduce how much taxes you pay. And then the fourth thing, compliance, gotta stay in compliance. And that means doing your tax returns on time, making estimated payments as they come due, payroll, all of that, are obligations for every business owner.

100%. What are your most popular services that you have?

I think we begin with tax resolution. I don’t like to call it resolution, but people with tax problems, that’s probably our most profitable or what we do most. I also help people with bankruptcies, you know, because I help companies with financial issues. And bankruptcy is one of the remedies. And too many of these outfits who are helping people with taxes, they don’t even

Yeah.

Offer that there’s really only six things you could do if you had the IRS money. So the first thing you do is you could pay them Most people that’s why there’s come to see me because they can’t pay them The second thing you can do is come up with some sort of an instalment agreement The third thing you can do is come up with some offer and compromise, which I think is totally overblown and and misunderstood Next thing you can do is get yourself in currently not collectible status and that’s just proving that you can’t pay the IRS

Yeah.

Fifth thing you can do is go into bankruptcy. Bankruptcy and tax is a very complicated area of the law. And the last thing you can do is nothing. And that’s what a lot of people do before they come to see me. One of them is pay, and one of them is do nothing. So really, there’s only four things I can do. And if one of those things is bankruptcy and your guy isn’t offering that, well, I think you’re missing something.

Gotcha, makes total sense. So what’s the future plan for yourself and the firm?

Well, I think we’re moving towards a membership model. We have already done that in that we have a subscription plan. As I mentioned, these things don’t go away right away. And so people need ongoing help with taxes, with the IRS, with their tax troubles. And so I came up with this subscription plan. Now, one of the things we’re trying to move to is more of a, you know, kind of a do it yourself so I can help people who can’t afford an attorney, give them information about how they can go about solving these problems. Then done with you, where we have a group, maybe video, I do some master classes. And then of course we do it for you, and done for you. So that’s the model. If you go to fightbacknow.com, you could sign up, have an email newsletter every day, we talk about everything that business owners need to think about. Productivity, taxes, IRS, marketing, things like that. So I’d encourage everybody, go to fightbacknow.com, sign up for the free newsletter.

Awesome, awesome. What activities have you done since the start of the firm that’s been the most successful to promote yourself and the brand?

I do a lot of radio interviews and I’m doing a lot of podcasts and things like that to get the word out. Advertising, obviously you have to do some advertising. I do some advertising on radio, but I had a radio show for some years. I still appear on a lot of radio shows and I do my own podcasts and things like that. But you have to advertise and mostly I’m doing it online and on the radio.

Gotcha. Well, since most of our listeners are attorneys, aspiring attorneys or entrepreneurs, what are some challenges that you faced in the past few years and how are you able to overcome them?

Well, I think the biggest thing I mentioned, the subscription plan, I think a lot of attorneys, I just was on a podcast called the Subscription Attorney Podcast, and he talks to attorneys about adopting this subscription model, getting away from the hourly billing and things like that, flat rate fees. I think that’s a big way. I think that’s what’s happening in our industry. And I think a lot of attorneys ought to look at that.

I can tell you that in my practice, it’s changed my practice for the better. This one and done, you know, working, working, working to get clients and then helping them and then they’re gone. And then you’re working, working, working to find more clients. It just doesn’t make sense. doesn’t, you know, once you find someone that trusts you, you should keep selling them what things that they need. And there’s a lot you can do to help them. And that’s what you should be doing in my mind.

Awesome, awesome. What piece of advice can you give someone that’s looking to start a firm here in the next year?

Well, I think new attorneys, and I can speak to this because I have two sons and one son has been a lawyer now for a year. My youngest son is in his third year of law school. So, you know, I think a lot about this. I mentioned I have a podcast. I interview a lot of attorneys. And one of the questions I always ask them is, you know, what advice would you have for my sons?

So that’s kind of what you’re asking me. And here’s what I would say. Too many attorneys kind of fall into a job. And that’s why a lot of attorneys don’t like their work. Find what you love to do and then do that. You don’t have to make a ton of money right out of law school. I mean, it’s great if you can, but sometimes that’ll trap you. Don’t get trapped. Do what you love. The law has such a varied interests, right? Every area that you can imagine needs a lawyer. And many attorneys don’t even practise law. They do other things because being an attorney really does train you to do so much more. So do what you love. And I think that’s attorneys in almost everybody, right? Do what you love. And as they say, you never work a day in your life, right?

100 % I’m with you. See if there’s anything I haven’t asked you that you want our listeners to know.

No, I think I want people to know more about the IRS and to realise that the IRS is not your friend, that they’re really gearing against business owners. Attorneys seem to make some money and that’s who they’re targeting. And so you should get your ducks in a row, right? Make sure that you have this accounting system set up, that you have your compliance regime in place.

And then again, then you could start talking about reducing your taxes with tax planning. Because too many people just react. If I ask people, hey, what was your tax, what did your tax bill last year? What did you pay in taxes? They’ll tell me something like, well, I got $2 ,000 refund, but they don’t even know what they paid in taxes, right? So look at your tax bill. What did you pay? Then your eyes will open like, wow, I didn’t realise I was paying that much. Now you could take action to try to lower that. And that’s what I would encourage people.

Yeah

Awesome. Definitely. Definitely Steven Leahy. We can find you at chicagotaxteam.com and it’s also it’s a fightbacknow.com as well. Thank you so much for coming on the podcast. I appreciate your time today, Steven. Thank you.

FightBackNow.com. Sign up for my email newsletter. Yeah, my free email newsletter.

Well, thanks so much for having me. It’s been a lot of fun.

Definitely.

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