#156 From Attorney to 700+ Units with Justin Spiller
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Justin Spiller, a double Buckeye from Ohio, transitioned from a 7-year corporate law career at firms such as Bailey Cavalieri to full-time real estate entrepreneurship in 2016. His legal training provided critical advantages in risk assessment, contract analysis, and business structuring, which proved invaluable in building a real estate portfolio now exceeding 700 units. Before entering real estate, he launched a successful photo booth business, gaining hands-on experience in operations and scalability. He was driven by his father-in-law’s advice to pursue a recession-proof, recurring-revenue business, which led him to real estate after recognizing its resilience and steady cash flow. Justin leverages AI tools like Grok—valued for real-time legal insights and risk detection—to draft demand letters, review leases, and improve contractual language based on Ohio case law. He views AI as a productivity enhancer rather than a replacement, emphasizing that it consolidates workloads but requires human oversight to maintain legal accuracy and context. His journey illustrates how legal expertise and entrepreneurial agility can converge to build sustainable, scalable real estate ventures.
Episode Introduction, Market Update, and Guest Background
You're listening to the Reinvest Podcast, where each Tuesday we show business owners and entrepreneurs how to diversify into real estate by equipping you with the tools and tactics to build generational wealth.
Your hosts, Garrett Gatton and Seth Simonello.
Hey guys, welcome to another episode of the Reinvest Podcast, episode 155.
Speaker 2
I was going to try to steal your intro.
I was too.
Speaker 1
Slow.
Yeah.
You weren't.
You weren't.
Speaker 2
Quick enough wasn't quite fast enough this time.
Maybe next week.
Speaker 1
Got a good episode here today with Justin Spiller.
Justin, we're going to get into your story here very shortly.
But Seth, what are you seeing in the market side of things commercially investment related?
Speaker 2
Well, now that we're through this brutal winter, anyone that doesn't get winter, like people that are in the South, I mean, I guess even Texas got a little winter this year.
In Florida, they got cold.
But anybody that doesn't get a winter, you don't quite understand.
But man, it really affects the cycles here.
But we're seeing a lot of buyers come out of the woodwork, a lot of people starting to really get active again.
Now that we're through the thick of it, it seems like people prepping for spring, people prepping for that life change.
So starting to see a lot more activity across the board, commercial, residential.
So it's kind of got me excited.
I always feel energetic when there's opportunity out there.
So it's kind of like, oh wow, it's fun.
Everybody's moving again.
Speaker 1
It feels like people are starting to do deals again, which is nice.
But well, somebody that could speak to that today is Justin Spillers.
Justin, you're kind of a you're, we're in your backyard or you're in our backyard, I don't know which.
But you're from Ohio.
You're an Ohio guy says you're a double Buckeye.
What does that mean?
Speaker 3
Yeah, went to Ohio State for undergrad and law school.
Speaker 2
So nice.
Speaker 3
Got 2°.
I just thought if I kept going to grad school, I'd get better football seats.
Speaker 2
What did that work out or no?
Speaker 3
Their peaks at 4, you can't get any better seats than four after after undergrad.
So I thought I'd like sideline passes by year 7 maxed out.
Speaker 1
I will say we, we have a, a client of ours that does some, some construction related work for Ryan Day.
And was it 2 years ago maybe Ohio State was playing for the national championship and he was like, hey, you know, I depending on how this game goes, I might be doing a job for him so.
Speaker 2
Which two years ago was good, was good.
Speaker 1
So that's right.
That's right.
Speaker 2
So actually, sorry, while we're on the Buckeyes, I met the previous Brutus mascot.
Oh, seriously?
Yeah, so he was he's actually working at a local factory here in Lima.
OH, believe it or not.
Speaker 1
Sorry, I'm sorry.
Speaker 2
And so, but he is a great job so.
But I, I just thought it was funny.
That was like, I was like, oh wow, he's just a regular person, so.
Speaker 1
He's Brutus.
That's amazing.
Justin, you have a degree as in a corporate attorney.
So did you, you got your law degree.
Give us a little background kind of through your professional career and then right when you transition into real estate.
Justin's Journey: Law Career, First Business, and Legal Advantages
Yeah, so I went to underground Ohio State, always knew I wanted to go to law school, pretty law, my father-in-law into a really large business.
He said I, I told him I wanted to get in business on my own.
He said, go to law school.
It's the one thing you can't learn on your own on the streets.
So he wished he would have went.
So I took that advice, stacked up, got a finance marketing degree pre law and undergrad.
Went to law school focused on corporate real estate law practice for about 7 years, large from downtown Columbus, OH, then a local firm here in Sidney, OH.
During the gamut of small business entity formation, helping companies grow all the way to when I was in Columbus working for Fortune 50 companies on M&A work, securities offerings.
So kind of got to see it all.
And then in 2016 was able to go full time in entrepreneurship, start investing at that time with my business partner Brandon.
We bought our first property then and we've grown it to a little over 700 units now.
Speaker 1
Man, So what was the law firm in Columbus that you joined and did mergers and acquisitions for?
Speaker 3
It's called Bailey Cavalieri.
They're downtown.
That was like the epitome of experience there in the US Bank high rise.
I had a corner office, all glass windows overlooking N so I could see the Ohio State football field walking in wearing a suit and tie and a briefcase every day.
That was super cool experience.
And then working with the best of the best corporate clients, just super high expectations working non-stop.
It's the billable hour you got track your time every six minutes.
I'm working 60-70 hours a week.
Get to the office, it's dark, leave it's dark.
So good time to grind.
When I was young, free kids, but got that out of my system, paid off all my student loans, got debt free.
Was kind of the goal.
Kind of figured out which businesses I wanted to start.
I had a couple of side businesses during that time, but 2016 was able to take the plunge and go into business full time for myself.
Speaker 2
So what were some of those other businesses that you'd started to explore with before maybe you jumped in full time?
I mean, what, what kind of stuff were you into?
Was it only real estate stuff or was it just you were kind of everywhere Uber driver?
Speaker 3
Yeah, Now even other than that first business in undergrad, me and my friend had the idea of putting a green screen into a photo booth.
And so we created the first ever green screen photo booth in Columbus and we grew it to five booths.
We had 12 college kids running them.
We're doing events all across the mid central Ohio.
And then we added on photography, DJ and everything and kind of one stop shop events company.
So that was the first four rated business that then an undergrad and in part law school sold that company and that was kind of the start of the entrepreneurial venture, so.
Speaker 1
Like did you, I mean, did you sell it for a profit, A profit?
I mean like.
Speaker 3
Yeah.
So we, we did pretty good, probably could have sold it for more if I knew how the fun Hermosi structure of actually creating value and not having that key man risk in it, which we were just, we were kind of done with it.
We were ready to move on to the next thing.
But yeah, we did 100,000 in revenue with just photo boost in the first year, which is pretty miraculous.
Storing them in a a storage container, two of them in a horrific part of Columbus, having college kids go there with our key lock, get the stuff, trust them to bring it back.
It was just like everything you can imagine going wrong in the first business.
You learn real fast.
Speaker 1
Funny that you were an attorney at this time and.
Speaker 3
I know this is pre pre attorney.
OK, so this was this was this was undergraduate.
Speaker 1
Aware of the liability after yeah, this.
Speaker 3
Is this is before I really knew what I was doing?
Speaker 1
That's pretty cool.
I I can only imagine some of the things that would happen in a photo booth.
I'm sure you've got some stories off camera.
We'll talk about that later.
But very cool.
So but I want to drill down on the advice that your father-in-law gave you.
Did that prove to be true?
A.
Speaker 3
100% going to law school, I probably stayed practicing an attorney maybe a couple years too long, but the experience I got was invaluable.
Knowing the out of perimeters and boundaries of the legal side of everything.
You can just make calculated decisions better than anybody else.
From the sense of I know what my worst case scenario is, I know what the risks are.
I can read any contract, I can read any agreement.
We used to do all of our own title work.
I do all this obviously over on PSA's we've gotten really creative in a purchase agreement that we're doing some things I've not heard anybody else do.
So that aspect has just been super advantageous like some.
Speaker 1
Sub 2 stuff.
Speaker 3
We we used to do all kinds of creative financing back in the day.
It helped them too, Yes, but not from the sense of that so much.
But yeah, just knowing the legal aspect of all parts of your business is super helpful.
AI's Legal Impact and Discovering Real Estate's Potential
What are your thoughts on AI and attorney work?
Speaker 3
It's going to decimate them.
They're going to get absolutely yeah, associate attorneys.
They're only needed because the partners don't want to do the grunt research work and AI does it now instantly.
So it's going to be super interesting.
I'm actually unbelievably fortunate because the prompting needed and knowing when AI is hallucinating, like it just makes up case law and it still does.
Like it just makes up case law.
That's not true, but the principles that it gives you is spot on.
So if I would say, hey, write this demand letter, I literally just did this.
I got, we just did a big patio audition.
I got a dented stainless steel door for our built in grill and I wanted to return.
And the return policy was literally the the stupidest thing ever.
It was like you couldn't have opened the box.
You had to warn us in the first five days.
Like all this stuff.
And I just said, AI, I'm an attorney.
Give me a hammer demand letter.
And it gave me this like, hey, you breached consumers practices act.
You did this.
I'm coming after you for triple damages.
The class action law slow stuff.
This instantly did it.
I copied paste to send it to him instantly.
Like we'll refund you, throw the throw the thing away.
You don't have to return it.
So like that is super good because like I just pasted it.
I took a little out where I knew like that's pretty stupid.
Like no one would say that, but 98% was spot on.
So that stuff is so good.
And even now I use it probably one to two hours a day, both as the operator, but even on the attorney side.
And then I run every agreement through it first like a, what's my three blind spots?
What am I missing?
Where what could go wrong?
Where should I add it?
It's just it's so good, especially with our leases.
I've gone through every provision in our lease and just said hey how do I make this better and and knows the context update of who I am and it just gives me the best language possible based upon Ohio case law.
Speaker 1
Now are you paying for like the closed loop ChatGPT or is this a different?
Is this copilot?
What's your AI tool you're using to do this?
Speaker 3
Yeah, so I've used a lot.
Brock is my favorite by far, the one that's X.
So Elon Musk is in my opinion the best because it can pull real time information from the the web and it uses all the X data.
So I use grok.
I think the paid accounts like 20 bucks a month or something cheap.
But that's my AI of choice.
Interesting.
Speaker 1
Yeah, I just had to ask about that because that's been kind of a hot button, you know, a hot topic in terms of how that was going to disrupt the the legal industry.
And I mean, essentially with so many and we didn't talk, we're not here to talk about AI.
But I think it's worth noting on the, the, it's a job consolidation versus like a total replacement of jobs, I think.
And so it's people that know how to use AI that are going to stay in some of these positions because it's going to consolidate the work.
It took three people to do, it's not going to take 1.
And I think attorneys are kind of subject for that so.
Speaker 2
Let's go back.
You started some businesses, you in 2016, you said, hey, I'm going to make the plunge and work for myself.
And so you exited attorney work at that point, right?
Yeah.
OK.
And then when did you know it was going to be real estate or what led you to real estate?
Speaker 3
Yeah, I don't, I definitely did not think it'd be real estate going in again.
Same father-in-law kind of said, hey, get in a business that's recession proof and you have recurring revenue.
And so I was thinking more like bread and eggs and like the food everyone buys good times it bad got customers always buying it.
So explored some manufacturing worlds that area and then real estate kind of came out of nowhere.
I read looked like everybody else, rich dad, poor dad, kind of got down that rabbit hole, bigger pockets, etcetera.
Really like the concept of it.
I had a lot of clients that were operators and they would dump their money into real estate like everyone does now.
And I'd always ask them like, why are you doing that?
What's the benefit?
And they would tell me all the tax benefits and I kind of pieced it all together and I started looking at buying my first single family home as a rental property.
And that's why I ran into my business partner Brandon.
But we bought our first one, started growing it and eventually that became the best opportunity vehicle and the whale that kind of swallowed the rest seeing that we could make go the most money there and had the best kind of runway, if you will, for a career.
But it checked both those boxes, right?
Our residents are reoccurring revenue stream.
They always pay us.
We don't have to go out and hunt for new ones that often.
And then in good times and in bad people need a place to live.
They pay their rent first.
So indirectly check the boxes.
I was chasing from an early age but I did not know it was going to be real estate.
Podcast Summary
Key Points:
Justin Spiller, a former corporate attorney with a law degree from Ohio State, transitioned into real estate entrepreneurship in 2016 after gaining extensive legal and business experience through his work at firms like Bailey Cavalieri.
His early entrepreneurial ventures, including a green screen photo booth business, provided foundational experience in operations and risk management, which later informed his success in real estate.
Justin credits his legal background for enabling smarter decision-making, risk assessment, and creative contract structures in real estate, while also leveraging AI tools like Grok to enhance legal drafting, identify lease flaws, and ensure compliance with Ohio case law.
Summary:
Justin Spiller, a double Buckeye from Ohio, transitioned from a 7-year corporate law career at firms such as Bailey Cavalieri to full-time real estate entrepreneurship in 2016. His legal training provided critical advantages in risk assessment, contract analysis, and business structuring, which proved invaluable in building a real estate portfolio now exceeding 700 units. Before entering real estate, he launched a successful photo booth business, gaining hands-on experience in operations and scalability.
He was driven by his father-in-law’s advice to pursue a recession-proof, recurring-revenue business, which led him to real estate after recognizing its resilience and steady cash flow. Justin leverages AI tools like Grok—valued for real-time legal insights and risk detection—to draft demand letters, review leases, and improve contractual language based on Ohio case law. He views AI as a productivity enhancer rather than a replacement, emphasizing that it consolidates workloads but requires human oversight to maintain legal accuracy and context.
His journey illustrates how legal expertise and entrepreneurial agility can converge to build sustainable, scalable real estate ventures.
FAQs
His experience in contract analysis, risk assessment, and business structuring allowed him to create smarter, more resilient agreements and identify potential flaws early. This gave him a significant edge in managing real estate transactions and minimizing exposure to liability.
The photo booth venture taught him hands-on operations, scalability, and risk management—key lessons in running a business with multiple moving parts, which directly translated into his ability to manage and grow a real estate portfolio efficiently.
He realized that real estate offered both recurring revenue and strong demand during economic downturns, as people consistently need housing. This combination aligned with his goal of building a stable, long-term income stream.
He uses Grok to draft demand letters, detect lease flaws, and generate contract language based on Ohio case law. The AI identifies risks and suggests improvements, helping him create more accurate and legally sound agreements quickly.
After observing clients invest in real estate for tax benefits without understanding the underlying value, he started analyzing the model himself and realized the combination of steady cash flow and demand made it a superior long-term business model.
Yes, he emphasizes that AI provides fast insights and drafts, but he always reviews and edits the output to ensure legal accuracy, context, and alignment with his business goals—acting as a productivity tool, not a replacement.
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