E143 | Mike Miligan: How This Financial Advisor Pays Only 2% Tax – Legally

What if the secret to building wealth wasn’t working harder—but paying smarter?

In this episode of The Proven Entrepreneur Show, host Don Williams sits down with Mike Milligan, Certified Financial Planner and founder of 1 Oak Financial, to unpack the tax strategies and mindset shifts that helped him build a multi-million dollar business—while legally paying just 2% in total tax.

Mike shares his journey from counting cash in coffee cans for his grandmother’s cornbread sandwich hustle to becoming a bestselling author of The One-of-a-Kind Financial Plan. You’ll hear how desperation sparked innovation, and how real-life lessons shaped his mission to help entrepreneurs build wealth and reclaim time.

Whether you’re a founder, real estate agent, B2B leader, or aspiring entrepreneur, this episode delivers actionable strategies and real-world wisdom to help you thrive financially.

For information on how to work with Don visit us at https://donwilliamsglobal.com
You can also reach out to Don Williams at https://provenentrepreneurshow.com
 

Watch the episode here

   
Hey, Don Williams here with today’s episode of The Proven Entrepreneur Show. I’ve a real expert for you today, a financial expert, Mike Milligan from 1.Oak Financial. Welcome to the show, Mike.

It’s nice to be here, Don. Thanks for the invitation.

Man, my pleasure. Thank you so much for coming. So tell us a little bit about 1.Oak Financial, what you do, who you serve, why you do it, all that stuff.

One, Oak Financial is a dynamic financial services firm, headquartered in Norfolk, Virginia. But we serve all of the United States, including all the way out to Hawaii. I’m the founder of the firm. It formed five years ago as a company called Ideas by Mike, currently has 21 employees. With our partner employees, we’re over 100 in total. One of the things that’s unique about this firm is that

I’ve written a book called the one-of-a-kind financial plan. See, one oak doesn’t, it’s not about a tree or about an acorn. It’s about being one of a kind, one oak. And we genuinely believe that everyone is unique. They have their own stories. They have their own desires. They have their own life to live, but they get bottled up in what the one size fits all. Financial world wants them

to do with their retirement accounts, their investment accounts, their life insurance, their retirement income. And what they’re missing is that the biggest expense you ever have is your taxes. And so we actually do tax planning, retirement income planning, then we do investments, long-term care planning and legacy. It’s all detailed in a book I wrote called The One of a Kind Financial Plan that’s available out on Amazon. It’s Amazon bestseller.

Hmm.

And it’s great, created a lot of traction. I mean, it’s something that we live out in our company, but we help our clients live. Because if you want to live a one-of-a-kind life, you probably deserve a one-of-a-kind financial plan.

Yeah, I love that. I love that. And if you want to live a one of a kind life, you got to have a mission and a goal of what that’s going to be. And so that makes perfect sense to me. So, Mike, tell me, most people think of financial advisors as like numbers guys.

Tell me a human story that got you into this business and I can tell that you want to serve people, that you want to help people. So tell me something on the human side, not the number side.

Well, I could go back to my first client, and it’s a story that I chronicle and a story that I learned from even now, 36 years later. My grandmother, my grandmother granny, and my… her granny, and then my pa, his name was Walter, her name was Elizabeth. My grandpa was a construction owner, so he owned a company that worked on building roads.

But when I was about 11, he just wore out. Like he was physically, couldn’t do anything, had a lot of ailments, refused to go to the doctor because he was a proud Southern man. We finally went to the doctor. They found out that it wasn’t like aches and pains from like muscles. It was cancer, full body. I was the son of a high school mother. My mom, I love her dearly. She is like one of my idols in life.

We grew up together, but Granny and Pa were instrumental in like my upbringing. And so, I got to witness firsthand what it was like for someone who’d been married 50 years to lose the love of their life, but also lose the primary financial support. And Granny knew how to do something very well. She knew how to be a wife, she knew how to be a mother, but she also knew how to cook food. And she had this recipe that people always asked her to make. It was a collard sandwich. So, two…

Hmm.

deep-fried piece of cornbread cut in half with collard greens that were just amazingly seasoned in the middle. And so what she did is she just started, you know, to cope with the grief of losing my pa, right? She started making them. And then she would take them to festivals, and she would take them to convenience stores, she would take them to lunch sites. And I get to saw her build a business out of desperation. She innovated out of desperation.

And I didn’t know what that meant. Don, I was just living with her, right? I was living life. And so she asked me to count her money. We put it in spiral down notebooks, we would put the money in Folgers coffee cans. We would also wrap the big bills up in tin foil and put them in the freezer and she would write liver across it. Because she said if I ever got if somebody ever rosemary, they’re never going to take the liver out of the freezer. Right. And so they’re not stealing liver, right. And so

I agree, they’re not stealing the liver.

So Granny, through middle school and high school, she brought me along for the ride. And I I helped with sales. I counted her money. I was, you know, I count her as like my first client because she taught me what it was like, but I met somebody else along the way. That was a branch manager in a bank who I just thought was the coolest guy in the world because he wore a suit. The only other person I knew in that life, in my life at that time who wore a suit was the preacher man, right?

But I saw this guy, and I used to think preacher men dressed very well, right? And I saw the banker wearing it. I was like, how do you become this? And that’s what I wanted to become is I wanted to become a bank branch manager. Because I loved money, because I got to play with it, count it for my granny. And I saw this guy wearing a suit, and I wanted to dress like that. So wanted to become a branch manager. So I went to college. First person in my family to go to college. And when I was there, right, I got introduced to investments, trust management, estate planning. I was like, that’s what I want to do.

Right. know, Don, Tom Brady was meant to be a quarterback. And Tiger Woods was meant to be a golfer. Peyton Manning was meant to be a quarterback. Derek Jeter was meant to be a shortstop for the New York Yankees. Mike Milligan was meant to be a financial planner. And I date that back to like seeing my grandmother, right, helping her, helping her build a business. But not only am I supposed to be a financial planner, I’m supposed to be a financial planner who’s an entrepreneur.

I love that.

own my own business, think outside of the box because that really that’s one of a kind.

Yeah. And thanks granny. You did a good thing and did it because you had to do it. But many times that’s what happens with a successful or proven entrepreneur. So let me ask you this. What’s a common big money mistake you see entrepreneurs make over and over and what’s the smarter path that you’d advise them to take?

Entrepreneurs make the biggest mistake they make is with, I think they make two huge mistakes, one with money and one with the business. The first one I think they make with money is they don’t pay their taxes. And then they don’t realize what the tax strategy can be that you have because you are a business owner. See, I can talk about this from a financial planning side because I know the tax code. mean, I’ve done it, know, taxes when you’re a business owner, entrepreneur,

you get the whole dollar, right? If you’re an employee somewhere, you don’t get the whole dollar, right? As an employee of somewhere, you get something less than the total dollar because taxes are taking out Medicare, Social Security, your benefits, all that’s taken out, so you’re getting some percentage of the original. As a business owner, you get the dollar. And then you get to deduct your expenses, and then you get to pay taxes. Totally different as an entrepreneur versus an employee.

But what you don’t realize is there’s a lot of stuff in the tax code, like the Augusta rule, right? That allows you to use your personal residence for business, right? So the Augusta rule allows you to have meetings in your home as a business expense and pass money from your business onto your home tax free. And that’s an expense before you pay taxes. Another thing entrepreneurs don’t realize is you’ve got this, if you drive to multiple locations,

for your job, you can buy a car and expense it. It’s called bonus depreciation, section 179 bonus depreciation. There’s a lot of stuff that’s on TikTok and Facebook that tells you how to do it. But the thing about taxes that entrepreneurs don’t know is that taxes can come pretty low. Don, I’m gonna let you in on a secret about my life. Do you mind if I do this? I am such a proponent. I’m an American. I love being an American. I love being a patriot. I will pay my fair share of taxes.

Tell me.

But I want to pay the least amount I possibly can. So my wife and I actually moved to San Juan, Puerto Rico. Now, my corporate headquarters is in Norfolk, Virginia. Remember that part of 1.Oak Financial where across the country, all the way I have an office in Hawaii, all the way back to Norfolk. But I’m a resident of San Juan, Puerto Rico because as an entrepreneur, I can import money into the island with a couple of restrictions, You know, closer connection, have a residence.

do more in Puerto Rico than I do here, live more in Puerto Rico than I live here. But on that money, I pay 2 % tax. And when I mean tax, I mean 2 % total tax. You know, don’t, the money that’s imported, I don’t pay federal tax, I don’t pay the state tax on it, I don’t pay social security tax, I don’t pay Medicare tax. I pay 2 % federal. I am such an advocate for entrepreneurs of understanding the tax code that my wife and I will live in paradise for six months plus a day. We actually live more than that there.

But I’m such that I will sacrifice living in Puerto Rico to pay the least amount tax possible while still running a multi-million dollar business back home. And so that’s like the first mistake is taxes. And that’s something that I help people solve for, entrepreneurs solve for is the tax. And the second thing I have is I think entrepreneurs don’t pass on responsibility in their business. And I mean, you can’t pass on ultimate responsibility, right, of managing the business, but

What you can never replicate is time. And so if you’re doing 100 % of the things in your business, right, and you can’t grow, it’s because you’re doing 100 % of the things in your business. You have to find out like if there’s 14 things that make your business successful, what are the three or four things you like doing the most and then hire to do the rest. Because if you hire somebody to work full time, and they can do it 80 to 90 % as well as you can, it allows you to get that time back.

And like if you really want to exponentially grow as an entrepreneur, bring people in, create opportunities for people and realize if they’re doing it 80 % of the way, 80, 90 % of the way you’re going to do it, it’s going to give you back the time to grow your business.

Man, I think that is pure gold. If you can find somebody who can do it even 80 % as good as you, you should offload it. Okay. And go to, go to things that you’re magnificent at that are in your zone of genius and work there only. So.

That’s right.

Right.

That’s not what

I thought you were going to say was gold, by the way.

well, you know, you hear different things. The other thing is on the tax thing.

You know, entrepreneurs, they’re looking at their P &L, what’s their biggest expense? And truthfully, for most of us, the biggest expense we have in life is our tax load. know, and so anything you can do to lighten that. And I totally agree, we’re brothers from other mothers. I want to pay every…

dime that I owe, but I don’t want to owe any more than I have to. And so it’s just a matter of applying some knowledge and some logic. And if you don’t have the knowledge or have the logic, that’s why, and you’ve heard this a hundred times on the Proven Entrepreneur Show, talk to a professional, talk to somebody who they already know, okay, and let them help you. Many times entrepreneurs, we think we’re saving a nickel.

because we’re going to figure it out ourselves, but I assure you, Mike has forgotten more about financial services than the average entrepreneur will ever know. And so you just reach out to an expert, make it simple, get your time back. Okay. Now I’m looking for a, a case study and an anonymous case study where you helped an entrepreneur or a family completely transform. me the before and after.

that you can without identifying the client.

I I love talking about my story, but I’ve already kind of given away the ending of that. Instead of paying 37 % federal tax and 5.5 and 3 quarters in Virginia, I’m paying 2%. So I’ve given you away the end of the story on that one. So I mean, I guess I’ll talk about from an entrepreneur standpoint, I’ve got a, know, real estate agents are entrepreneurs in the grand scheme of things. They’re 1099 for the most part.

and they don’t get paid unless they close business. And most entrepreneurs it’s the same way, right? Whether you build homes or you own a retail shop, you own a restaurant, you don’t get paid until you sell something or build customers. But we’ll tell the story of a female realtor. She came to me as a…

looking to actually trade referrals. you know, having centers of influence, it makes building clients up a whole lot easier. But when we started talking, she had a little bit of whole life insurance, a Roth IRA, and she had some money sitting in the bank. What she didn’t have was a tax strategy. She had a CPA.

right? That was doing her taxes, but she wasn’t an S corp. She was just paying. She wasn’t drawing a salary for herself, right? She did not have someone on her team doing the $10 or $12 an hour work. She was doing it all from soup to nuts. And when we sat down and realized, and she told me she was 32 at the time, she said, I want to be a millionaire by the time I’m 40 years old. Okay, we’re going to fast forward a little bit.

She’s been a client now for five years. And she’s 37 years old. Again, when I met her, she had about 40,000 to her name. She was selling about eight or $9 million in real estate per year. Fast forward to this year. She now has a closing transaction coordinator with her, a social media person doing her social media, closing $13 million a year with $700,000 of liquid savings, right? That is invested not in a savings account.

she is going to hit the goal of a million dollars. now she, and where we were able to find that extra money done is her tax rate went down from 24 % to 7%. Right? And so we found money to save by first finding it in taxes and then getting the money invested. And a lot of times, you know, like people that are small business owners, most of their wealth is built up in their business.

Mm-hmm.

And, you know, rightfully so because they want to invest in themselves. They see a problem that they think only they can solve. So, yes, you should invest in yourself. But what you should also do is save in case you can’t solve the problems or you don’t have enough people to solve them for. That’s what I was able to prove with this one. Do want to hear the twist in that story, Don? She’s now my wife.

Yeah, I do.

So when we met over five years ago, not only was she trying to find someone to get to that, you she was trying to find a business partner to help get more business, but she had come off of a long relationship and so did I, right? And she still to this day still asks me for the flyer so we can refer people business to each other. And I’m like, I’ve never given it to you, but I’ve given her a ring.

and we are building a one-of-a-kind life together.

I love that. What a great story. Okay. We’re, into the fourth turn. I can see the, I can see the checkered flag coming. Okay. If you had a minute or two to give entrepreneurs that golden financial tip that could help build and protect wealth for the next decade. And I think I know what it is, but what would that be?

Most people at this point would say build your team out. Find somebody who can really help you, who’s not just creating historical documents, like not just doing your taxes or not just putting you in like a one size fits all. And yeah, that’s true, right? Find somebody who is an entrepreneur like you. I so often, like in my business, Don, find entrepreneurs who put their investment accounts or their…

their tax work with somebody who’s an employee of a bigger firm. Right? So they’ll go down to their local bank and use the financial advisor there. And those people are not bad. Those financial people are not bad. But really, what I tell you is, if you’re an entrepreneur, work with an entrepreneur. Right? Work with somebody who pays their own phone bill, who owns their own building, who pays, who has employees of their own. Right?

you

because entrepreneurs working with entrepreneurs will get each other. Entrepreneurs who work with employees do not get the encouragement or the real advice to actually grow business. What they get is what managers pass down from organizations. So I would tell you, if you’re an entrepreneur and you are working with a financial advisor or a CPA who does not own their own business,

truth.

Right, nobody, they may own their book of business, but if they work for a national firm where they get a W-2, they do not understand you, the entrepreneur. And I mean, if you want to work, if you want to work with one of the best entrepreneurs out there in this space, I’d say reach out to me.

Yeah, great, great advice. There’s a real brother and sisterhood for those of us who sign the front of the check, as opposed to those who sign the back of the check. And there’s just lessons we’ve learned and things we know that would terrorize and exhilarate people who have not learned those lessons. Mike, my

I’ve never heard it put that way, but.

Correct.

Real pleasure to have you on the show today. If somebody wanted to reach out to you or your company, share the best ways to do that, please.

The best, the easiest way to do it is just go to MikeMilligan.com. We don’t over complicate this. If you want to go and learn more about how I educate, coach and plan with people, MikeMilligan.com, there’ll be a link to 1Oak Financial there. And if you want to go to the company website directly, it’s the 1oakfinancial.com, one of a kind financial.com.

Love that. Mike Milligan, thank you so much for being my guest on today’s episode of The Proven Entrepreneurship.

Thanks folks, we’ll see you next time. Bye now.