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278. Financial Advice Every Solopreneur Needs to Hear · The Life-First Solopreneur

• 0:00
  Carly Ries: We have on financial expert Mike Milligan, who breaks down the paralysis penalty, which is the costly mistake entrepreneurs make when they delay financial decisions. And he shares practical strategies solopreneurs can use to reduce taxes, build smarter systems, and take control of their money. And Mike also shares the powerful story of how selling collard sandwiches with his grandmother shaped his entrepreneurial mindset. And it's a reminder that building a business and a future you're proud of often starts with simple lessons and the courage to take action. You're listening to The Aspiring Solopreneur, the podcast for anyone on the solo business journey, whether you're just toying with the idea, taking your first bold step, or have been running your own show for years and want to keep growing, refining, and thriving.
• 0:46
  I'm Carly Ries, and along with my cohost, Joe Rando, we're your guides through the crazy but awesome world of being a company of one. As part of LifeStarr, a digital hub dedicated to all things solopreneur ship, we help people design businesses that align with their life's ambitions so they can work to live, not live to work. If you're looking for a get rich quick scheme, this is not the place for you. But if you want real world insights from industry experts, lessons from the successes and stumbles of fellow solopreneurs, and practical strategies for building and sustaining a business you love, you're in the right spot. Because flying solo in business doesn't mean you're alone.
• 1:22
  No matter where you are in your journey, we've got your back. Mike, the topics we are going to get into today, I think are so important for every solopreneur out there. But before we dive in, we wanna ask an icebreaker question that we ask all of our guests, and that is what do you wish you would have known before you jumped into this crazy world of solopreneur ship?
• 1:44
  Mike Milligan: I wish I'd known how crazy I really was. You know, I don't mind taking risk. I don't mind you know, jumping first. I mean, I'm gonna be the first one if we go on vacation together that said, if there's a cliff to jump off, i will be the first one to say, let's do it. And then I'm gonna be the first one to do it.
• 2:02
  The second one to you know, the first one to repeat. But I just wish I'd have known how crazy the world of entrepreneur really is. It is the wild West. It is the great, the last great frontier. It's the place that freedom exists. you could do and be whatever you want to. There's a saying I often say that the only thing spotless that we have is the future. Being the entrepreneur allows you to create that future.
• 2:30
  Carly Ries: I love that. Well, and I was talking about the topic of the day. We're gonna dive into the financial world which some people, speaking of the future and the unknown. Some people hear that topic and they run for the hills because they're afraid of it. And some people are like, I need to know everything. we love having financial experts on the show because often you guys have different takes on different things. So from your take, I wanna ask you, what is this paralysis penalty that you talk about? And how does it specifically show up for Solopreneur who delay those financial decisions like I was just saying, because they're so overwhelmed or unsure of who to trust even?
• 3:09
  Mike Milligan: Well, I think if I wanna answer that one, but I wanna answer one other thing right off the top of the bat. If we're talking directly to solopreneurs who have an entrepreneurial spirit. If you're going to get financial advice from somebody, get some financial advice from somebody who is an entrepreneur. Right? The person at the bank, the employee at Merrill Lynch, the JP Morgan employee, they just don't understand you.
• 3:33
  They don't pay the bills. They get a check every two weeks. They're there to sell you but they don't understand the nature of what a true entrepreneur is. so The first thing you should do is find an entrepreneur financial professional.
• 3:49
  Somebody that signs the front of the check, not the back of the check. Somebody that pays the light bill. Somebody that owns their own building. And you know, it's somebody that understands what it takes to, struggle to make payroll or even not taking pay that month for yourself so somebody else gets paid. So that's the first thing.
• 4:07
  But the paralysis penalty is something that we talk about all the time because we're all And this is most entrepreneurs don't suffer from this. They suffer from being hyperactive when it comes to making decisions. The paralysis penalty is being presented with an opportunity and from lack of education or lack of trust that it's the right thing for you, you do nothing. You just sit there, you're paralyzed. often where that happens mostly in the world of financial planning and especially to entrepreneurs is when it comes to tax planning.
• 4:46
  Taxes are the thing that will drive entrepreneurs out of business. It will just you know, if you don't hit a payroll tax, if you don't pay your social security tax, if you don't pay quarterly estimates. And then all of a sudden you come to April of the next year and you're like, holy cow. Where do I get the money now to pay uncle Sam? you got the money all along the way, You just didn't realize as an entrepreneur, need to start, a third of it is the government's, a third of it is yours, a third of it's the business, right?
• 5:18
  And so every dollar you bring in as an entrepreneur is not yours. And the sooner you realize that, the sooner you break that paralysis penalty. You can actually go to real growth.
• 5:29
  Carly Ries: So what are some of the most overlooked tax strategies are that solopreneurs can start implementing? Even today, I feel like the new year rolled over and I already started thinking about tax season. And I'm like, ah, so what can they be thinking about to reduce taxes without like super cocky structures or anything?
• 5:46
  Mike Milligan: Well, you know, the ones that entrepreneurs forget about, and your listeners may say right away, I know about these, but they forget about the home office deduction. They forget to record all of their expenses. They forget to have, some kind of tool that says, I just went to office max and I spent $37 and you forget to put it down. They also mix a personal credit card and a business credit card way too often. the best thing you do is, if you're a business owner, get a business credit card, get a business account, run everything through there because it makes tax planning a lot easier.
• 6:21
  But here are some things that most entrepreneurs don't know about till it's too late. If you're a solopreneur, you could save more money tax deferred using a solo k than any other employee of another company out there. And if you're a true solopreneur and you're married, even though your spouse may or may not be in the company, you can actually do, a solo k for you and your spouse through that business. So you could actually save a lot of money for your future. The number this year, I think $77,000.
• 6:57
  So you could put away a $154,000 if you're really successful and do something really cool. So that's the first thing, saving for your future to help save taxes today. But then there's some really cool things that solopreneurs could do. Have you guys ever had a guest talk about the Augusta rule at all? Do you know what the Augusta rule is?
• 7:15
  Joe Rando: Doesn't ring a bell. No.
• 7:16
  Carly Ries: Joe, you would remember more than I would.
• 7:19
  Mike Milligan: Joe, are you a golfer at all?
• 7:21
  Joe Rando: I am not. No. I tried it. I was terrible. I tend to like things that involve more sweat.
• 7:31
  Mike Milligan: Okay. That's fair. Well, there's a tournament that happens every year in Augusta, Georgia called the masters. Now Augusta is not known for being the hotel mecca of the world by any stretch of the imagination.
• 7:44
  They have one event, it happens one week a year and then Augusta turns into a sleepy town all of a sudden. But a senator a while back got with some people in Augusta, got something passed through the IRS code that allows for residents of Augusta to rent their home out for forty days per year. The week of the masters and the week after the masters. Think about it. So for forty days a year, they rent their house out and it's tax free. As a business owner, you could do the same thing. You could rent your home out for fourteen days a year. It doesn't have to be consecutive like the masters. You could have 14 mastermind sessions at your house.
• 8:35
  You could have 14 client parties at your house. If you have contract employees, instead of going to rent a conference room or going off-site where you're spending a lot of money to rent, rent your home out and you could take money from your business into your personal name tax free. There's some structure around that that you have to do, but it is amazing. Like in 2024, my wife and I were able to get a $192,000 out of our business. Tax free.
• 9:12
  Joe Rando: But question on that. So when I do that and I take it personally, you know, take it out of the business and put it personally, that's taxable income to me personally. Right?
• 9:20
  Mike Milligan: It's not. Because you're using it under the Augusta rule.
• 9:25
  Joe Rando: Okay. So the Augusta rule applies everywhere, not just Augusta.
• 9:29
  Mike Milligan: exactly Got it. That's exactly right. But it's out there. There are some other things out there. You've got the section one seventy nine deduction about buying a car that's over 6,000 pounds.
• 9:40
  You know, that's typically reserved for people that move heavy material and all that. But if you're a business owner, you drive to not the same place every day, you could do the same thing. You could buy a car, let the business buy it, you could depreciate it. There's five or six other tax loopholes like that that the solopreneur, business owner has an opportunity to use that most people don't. My wife and I took advantage of one that is the greatest one out there.
• 10:09
  We're actually residents in Puerto Rico. We've actually moved to Puerto Rico. It's where our driver's license is. It's where we spend the most time. It's where we are closer connected to than anywhere else.
• 10:21
  It's where we give money to charity. And because we're there, money that is made in the Mainland United States that is imported into Puerto Rico avoids federal taxation. And we only have to pay a small, small, small tax in Puerto Rico.
• 10:38
  Joe Rando: Interesting. Question. What about subchapter s elections?
• 10:45
  Mike Milligan: Oh my gosh. that is one joke. Glad you asked that. Because I went from zero to 60 and blew through three red lights and that was the sub chapter s, right?
• 10:56
  So sub chapter s, it created a payroll for yourself, saves a significant amount of social security and Medicare tax. Paying yourself a reasonable salary, on a payroll that it allows you to take above that payroll distributions for the company that are not subject to,
• 11:19
  Joe Rando: Self employment tax.
• 11:20
  Mike Milligan: That's right. Exactly. And that's a huge saving by the way. That's when you do the employee and the employer part of that and then you add back the Medicare side of that, that's between 14 and 16% that you could save just by electing sub chapter S and acting like a business running the payroll.
• 11:37
  Joe Rando: Yeah. I mean, we should point out that there are some things that come with that. You have to have an annual meeting and, file some paperwork and things. But, you know, I mean, I look at, like, Zen business. They'll do all this stuff for you for pretty much peanuts.
• 11:50
  Mike Milligan: That's exactly right. Yeah. I mean by the way, if you're a solopreneur, who are you having the meeting with? I mean, it's you yourself.
• 12:00
  I mean, we technically could have, three business meetings right now, put them on the notes and it'll be recorded right now. Right? So it's a requirement. It's a checkbox. Anytime there's a loophole, anytime there's something you have to do, there are some requirements you have to fulfill to actually make them work.
• 12:21
  Carly Ries: So Mike, you just seem like you have a treasure box of all these like little things people can be taking out of it.
• 12:27
  And Joe, you're asking such great questions. I wish I was asking these great questions but I am one of those people where it sounds like you're speaking Chinese for a lot of this. And I know that I need a lot of hand holding in my own business. And so for people, you say that people trust car sales people often more than they trust financial advisors in any way, shape, or form. How do they find the good ones?
• 12:52
  Like Joe, you talk about Zen business, but if they wanted to work with a real person, one on one and all that, what should they be looking for? first you said they need to be an entrepreneur.
• 13:05
  Mike Milligan: Yeah. You know, Joe probably has a lot of great opinions on this too, but my opinion is everybody has problems. And if you could articulate what your problems are and you feel like the solution be given to you genuinely solves your problem, you found somebody that's right. Unfortunately, we get this feeling and I don't like to think business owners should trust their gut because a gut is something that will get you in trouble.
• 13:38
  A lot. But what you should do is trust what feels right to you as you go through the process. And so if you have problems and you feel like you're getting the same solution that everybody else is getting and it just kind of puts lipstick on a pig for your problems, then you need to go find somewhere else. I mean, if somebody was experiencing heart pains, they're not gonna let the ER doctor necessarily do the surgery on you. They're gonna wait for a cardiologist unless it's an absolutely critical emergency, right?
• 14:16
  They're gonna wait for the specialist, the cardiologist. We all have a specialist, a financial specialist that we need to find to help us grow to the next level. You know, in those one size fits all, those ER, those triage, the ones that do the same thing over and over in the financial world are sitting in banks and investment companies. They're not out living the entrepreneur world like your listeners are.
• 14:44
  Joe Rando: Mike, can I tell you a story? Because I think it ties back to this. So a while back, I sold a business, had a nice windfall. I took half of the money, and I gave it to my preferred financial adviser. And I took the other half, and I gave it to somebody that was more all corporate like you describe.
• 15:11
  And because a team had invested in this business, so I wanted to thank them. I gave him, like, three years. And the one with the entrepreneurial guy, the guy that I had identified using kind of what you just described, it was crazy. I just killed it. I was just killing it.
• 15:32
  And the other one that was what Robert Kiyosaki calls diversified, it was just that check the boxes. I actually lost money. I actually had a lower principal after three years than when I started, and I basically said, guys, I gave you a shot. Closed it up, moved it over. And you're absolutely right.
• 15:52
  I mean, you have to find that person. I don't wanna be in index funds. It's just not me. I wanna be thinking hard about what I'm investing in, and you gotta find that person that's willing to do that
• 16:02
  Mike Milligan: I mean, would agree with that. Like if you just wanna live life, passively. I mean, most entrepreneurs don't really live life passively. Why do you invest passively? I wrote a book called the one of a kind financial plan.
• 16:17
  It really inspires people to kind of live a one of a kind life. And it is like you said, Joe, you have to take more control of your money. If you don't, it will control you. It will influence the decisions you make later in life.
• 16:35
  And sometimes the first decision is the most important decision. It's who do you trust? Who doesn't feel right? And that's a really big decision that shouldn't be solved in one thirty minute meeting. It should be multiple meetings where you feel that you've been heard, your problems are clearly laid out, the problems you didn't even think about have have come to the surface And you have a plan to address the biggest expenses and the biggest risk you have in your life.
• 17:06
  And that's where our firm looks to do that. That's where I look to educate people. And then like, I even coach financial advisors, like ones that are looking to get out of those big box advisory firms into doing something on their own. I coach them to be unique and one of a kind. And that's because we are going to be more of an entrepreneur economy, even more so than we are now.
• 17:35
  We're gonna be that even more so in five years, in twenty years, in fifty years. Right? There's going to be Amazon, Tesla, Microsoft, and then a bunch of small businesses. And, you know, those three companies I've mentioned, there may be another one in there.
• 17:52
  But those three businesses are gonna do pharmacy, banking, retail sales, car sales. They're gonna do it all. And then we're gonna be left behind on the entrepreneur side to serve our communities or to solve a specific niche that like we are passionate about solving.
• 18:12
  Carly Ries: So for people who are just starting out as a solopreneur, and like you were saying, it's the wave of the future, it's already happening right now. What are some of the basic, not taxes, but just some of the basic financial systems that they should put in place once their business starts generating some income?
• 18:30
  Mike Milligan: Well, like if you have a specialty, you obviously see as a solopreneur, something that you could solve, whether that's a real estate agent, opening a new restaurant, whatever it is, you see a problem that you could solve, you need to spend a little bit of time upfront learning about finances. Whether that is like I teach a personal financial planning course, whether that's finding somebody like me who in nine hours over six weeks, you could get some tools to be able to go find, to ask the right questions. But then you need to start acting like a business from the beginning. And realizing that if nobody was ever gonna take my class, I'll give you a sneak peek in thirty seconds.
• 19:19
  Treat every dollar that comes in as a third of it is not yours. It's somebody else's, it's taxes or it's gonna be some deduction that you take. A third of it needs to be for growth and a third of it is yours to live on. And if you live within that basic framework of a third, a third, a third, right? Then you're already 90% further along than most business owners who start a business.
• 19:49
  Then what I would say is hire or get a really good tax planner because that's the biggest expense you're gonna have in your business that can be controlled, right? It is by far and away a controllable expense if you know how to dot the i's cross the t's and do things. So get a tax planner. And then as you're growing, make sure you have a really good, and bankers serve a purpose for a reason. Get a good banker. Somebody who you could go to if you're trying to build a 7 or 8 figure business, get a really good baker you could see face to face. If you're gonna be smaller than that, like a 5 or 6 figure business, you could do that through americanexpress.com. They have people right there that are there for you to call.
• 20:38
  But if you could get educated, a tax planner and then a banker, then you're ready to really start building your business and building wealth because there's a lot of things I can't tell people how to do with their business. I can't tell somebody who makes a widget how to make their widget better. I can't tell a plumber how to do his job better. I can't tell a doctor how to build his business from scratch. But boy, all that other stuff I could tell you exactly how to stay out of trouble. I can show you the pitfalls. I can show a lot of the failures that I personally have had in business and I've seen others have. I keep you out of those failures. And that's part of being a community and learning together is how you do that.
• 21:19
  Carly Ries: Well, so we're talking about the beginning and I saw this on your one pager and so I was very intrigued by this story about like, what lesson have you learned from your earliest business experience selling sandwiches with your grandma, I believe?
• 21:34
  Mike Milligan: It was. Collard sandwiches.
• 21:35
  Carly Ries: Collard sandwiches. How does that directly translate to modern solopreneur businesses? I just feel like there's a story here we need to hear.
• 21:43
  Mike Milligan: I didn't realize, when I was doing with my grandmother, building her business. I didn't realize what I was doing. And I feel like that's what a lot of entrepreneurs and people get in the business world. They don't know what the first one, three, five years, they just don't know what they're doing. But what I didn't know and what I've been able to reflect on almost forty years later is my grandmother innovated out of necessity.
• 22:09
  She did not want to start a business selling collard sandwiches. She wanted to be the wife to the love of her life, Walter, who was my grandfather. But he got cancer. Life happened. And he unfortunately passed away way sooner than he should have.
• 22:28
  And so here she is at 64, the breadwinner, her stud, because she called him her stud, like literally that was her man. her stud passed away. He brought in the money, he provided her comfort and safety and they they owned a small business themselves. He owned a construction company. They didn't exactly trust the government.
• 22:50
  So they didn't pay into the social security system like they should have. They didn't have a four zero one ks, right? Because they were products of the great depression. Not directly, but they were old enough to remember the great depression. So they they lived in a cash system.
• 23:08
  Well, the cash after my grandfather passed away started running out. And so my grandmother did the only thing she knew how to do which she made these collard sandwiches that he loved. I remember the first time she did it, I was with her. We went to a job site where he used to work. She showed up and she got all these hugs and people like, hey, how are you doing?
• 23:30
  She goes, well, she said to them, I need to pay the Bell South bill but I didn't want to ask for the money. So I made you guys lunch. Will you guys buy these for me? She literally sold them out of love.
• 23:44
  She fed somebody. They all gave her 5 or $10. For at a time, by the way, that you go to McDonald's and get the big mac for 99¢. Right?
• 23:54
  So this was a sacrifice. She literally counted up that money. We went down to the Bell South Building. She walked into the door, paid the bill with cash.
• 24:06
  She came out. She had like $7 left and she said we're gonna do this again tomorrow. And we did that over and over again to pay bills, right? And so literally, I learned how to sell when I was 11, 12, 13 years old because I would walk up to people and say, yeah, my granny made this today. Would you like to have this for lunch?
• 24:25
  Or would you like to take some home for dinner? And I learned sales through that process but we did it because we had to. We had to pay bills, right? We had to put food on our table. but it was so simple. People may be saying, well, a collard sandwich, what in the heck is that thing? It's just cornmeal that's deep fried and made into a bun with collards that come right out of the garden that she would put ham hock in. I don't even know what her secret recipe was, but it was good. And she'd put them in between, she'd wrap them up and we'd go sell them.
• 24:53
  And she eventually made that business into a fair business, almost like a state fair. If you guys ever been to a state fair, like the oddities of the state fair, her oddity was a collared sandwich. And I was at fairs with her when I was 14, 15 years old where she would sell 2,000 collared sandwiches on a weekend. Just crazy stuff.
• 25:12
  But that was the first business. We counted every penny. We counted every nickel. We counted every dime.
• 25:18
  But we recorded it on a spiral bound notebook paper and we stored the money in Folgers coffee cans until the until the cabinets got so full of cans that we had nothing to do. She would put the biggest bills, the 20 fifties and hundreds. She would line them, she would wrap them. She would put them with tinfoil and write liver across of it and put them in the freezer. She because she said, if anybody ever comes to rob us, they're not taking the liver.
• 25:48
  That's that was her thing. And so, I mean, there's just so much wisdom, so much uncommon small town wisdom that happened that I saw firsthand and you know, I loved it. I love sales. I loved helping her. I went to school and I would come home and I would say, Granny, let's go.
• 26:07
  Like that's what got me up every day. I did what I had to so I could do what I wanted to. And I loved it. And so I went to college. Along the way, we eventually opened our first bank account because the cupboards got too big.
• 26:22
  And so we went to the bank and there was a guy in there that was wearing a suit who I just thought was the coolest thing in the world. the only other person I knew that wore suits at the time were preacher men. And I did not wanna be a preacher man. But I wanted to wear a suit.
• 26:39
  So I asked him like, how did you get the job at the bank? And he told me, went to college and I did this and we had many conversations. So that's what I did. Nobody else in my family went to college, but I did it. I went to college so I could be a banker.
• 26:52
  What I didn't realize though was that this wild journey, I was never meant to be the person in the bank, counting the money. I was meant to be something greater than that. I learned that from my granny, that entrepreneurial spirit. And I took what I learned is twelve years working for Wall Street banks, to be able to come out on this other side as the next chapter, the end of my life chapter of my working life is going to be to help people gain real wealth.
• 27:20
  Through creating one of a kind financial plans so that they can live a one of a kind life like my granny did. Right? We were poor, but bam, we loved it. Absolutely loved it.
• 27:30
  Carly Ries: Mike, I had a few other questions I was gonna ask you, but we're not gonna ask because that was the best way to end the episode. I just thought it was so heartfelt and I'm like, you know, we're gonna cap it there. We have the two questions we always ask all of our guests, but that was just a great way to end this episode. But again, before we hop off, we have to ask you because we ask everybody, what is your favorite quote about success?
• 27:51
  Mike Milligan: Tony Robbins said, by changing nothing, nothing changes.
• 27:56
  Carly Ries: I hear he's been successful.
• 27:58
  Mike Milligan: He's a pretty good one to follow. he also breaks things down really simply and it's so true. If you're not willing to change, you're gonna have the same exact life you have. And that's one of the things that we want to Mike Billigan. I like to say be one of a kind. I want people to know that they're unique. They have purpose in life. and you're meant to live a one of a kind life. That's what this world needs. It's what we all need.
• 28:30
  Carly Ries: Love it. Mike, thank you so much. If people wanna learn more about you, where can they find you?
• 28:36
  Mike Milligan: Mikemilligan.com. Go there. You'll find all my socials. You'll find YouTube. You'll find Instagram.
• 28:42
  You'll find it all. Mikemilligan.com.
• 28:43
  Carly Ries: It's easy as that. Well, thank you so so much for coming on the show today. We appreciate it. this has just been so helpful. And listeners, thank you so much for tuning in.
• 28:51
  As always, leave that five star review. It helps us spread the word to other solopreneurs like you. Share this episode with a friend and subscribe on your favorite podcast platform including YouTube. We'll see you next time on The Aspiring Solopreneur. You may be going solo in business, but that doesn't mean you're alone.
• 29:09
  In fact, millions of people are in your shoes, running a one person business and figuring it out as they go. So why not connect with them and learn from each other's successes and failures? At LifeStarr, we're creating a one person business community where you can go to meet and get advice from other solopreneurs. Be sure to join in on the conversations at community.lifestarr.com.