Don’t Become An Entrepreneur

March 17, 2026|Podcast|

The Success Tax Podcast - Eric Green and Tony Carter | Entrepreneur

 

Everyone wants to be their own boss… until they realize what that actually means.

In this episode of the Success Tax Podcast, Eric Green and Tony Carter break down the real reasons you shouldn’t become an entrepreneur — from crushing hours and zero work-life balance to financial pressure, failure, and brutal self-assessment.

They share hard-earned lessons from law firms, cigar shops, real estate deals, failed partnerships, and side hustles that turned into multimillion-dollar ventures. This isn’t Instagram entrepreneurship. It’s late nights, missed games, unpredictable paychecks, and learning to own your mistakes.

If you’re dreaming about going out on your own — or already in the trenches — this episode will help you decide:

  • Are you ready to sacrifice comfort for control?
  • Can you survive without a steady paycheck?
  • Are you willing to fail… and keep going?
  • Do you know what you’re actually good at — and what to outsource?

Because the truth is simple: entrepreneurship isn’t for everyone. But if you’re willing to deal with the hard parts, it might be exactly where you belong.

Raw. Honest. No fluff. Tune in before you quit your job.

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Don’t Become An Entrepreneur

At Least Until You Hear This!

Welcome back to the show. I’m Eric Green. I’m joined by Tony Carter. We’ve gotten questions and everything such as why you shouldn’t be an entrepreneur or when should you decide, “This isn’t for you?”

The list is long and distinguished.

I’ve had businesses and ventures fail. I had partnerships that failed but I’ve had some that have worked out well. Tony and I start talking about over cigars, what are the big three reasons not to be an entrepreneur? The truth is, we’re going between AI and all of the tools that are available. Bigger companies are going to be in trouble. I do think White collar jobs are going to be in trouble, if the goal is to work at a company and punch the clock.

If you want to be an entrepreneur, it’s never been easier. Access to capital has never been easier. When I started my law practice, Tony, I would mail hard copy to 300 accountants, invite them to a talk and hoping people show up. We would do a talk. I’d rent the room. I’d pay for cocktails afterwards and some hors d’oeuvres.

I’m dropping $3,000 or $4,000 or $5,000 the hope to get cases and that’s how I built my practice. Now, I can do a webinar in Zoom. I can email hundreds of thousands of accountants and invite them in. With the automation tools, I can create marketing campaigns, social media posts, and show. There’s so many tools at your disposal now. Let’s talk about this. Who should not be an entrepreneur?

The person who doesn’t want to put in long hours because it’s not a 9:00 to 5:00. You and I know that very well. Most people take a hobby and want to go make a job. You’re not going to start at 8:00 and end at 4:00.

It’s funny because I hear from lawyers, given that I have a law firm. I’ll hear from friends of mine who are big firms, “I just love to work for myself.” Be careful what you wish for. I will tell you. I probably work as many hours as they do. Now, admittedly, I have a little more control. I can work at home. I don’t answer to anybody but, in many ways, if you think about it. I tell people I work for an asshole. I don’t get paid if I don’t work.

You work for a firm and payday comes. It’s directly deposited in your bank account. If I don’t collect, it’s on me. In many ways, it’s a different type of pressure. The pressure of the job is your answering to someone you have to make sure your client or whoever you work for, is happy. Your time is not your own. You get asked permission to take your vacation. When you’re self-employed, that pressure goes away. You have different pressure.

I got to bring in business. I got to collect the money. I’ve got to get the work done. I could sit and watch Harry Potter if I want all day long. I’m just not going to collect anything. I’m not guaranteed a paycheck, which, by the way, was my big one on my list, but we’ll get there. When you’re going to work for yourself, if you want to succeed, there’s a great video. I forget who he was talking about, but he mentioned billionaires. Elon Musk slept in the office. Jeff Bezos slept in his office. Bill Gates slept in his office. Do you see a trend here?

People that are all in on their business and if this is your thing, if you’re going to cut your logistics line and just go it alone, you’re in. You are the army of one. It is going to fall on you. I will tell you and I’d love to hear your take on this because you were a state trooper who became an entrepreneur. I would not have it any other way. No matter how much the stress is, I’d rather be in control of my destiny than waiting to find out if I’m going to get laid off when the market goes down or we lose a client and, all of a sudden, I’m going to lose my job and my livelihood.

The satisfaction you speak of was readily apparent. When I purchased a cigar shop over at Rocky Hill years ago, I was still working for the state at the time. On my off time, I would go to cigar shop. I had a business partner there and he was there an hours. I couldn’t be there, but much of those very first few hours in the morning was the best ever. A freedom to turn that door yourself, that key, that lock and walk in that store with all the lights off and flip them on. I can still smell that cigar shop.

I could still think about how great I felt change. Even something as simple as taking the garbage out and changing the ribbon on the register we used to use back then. Going in the humidor and looking at what we should call front marks and realizing what needed to be rotated to increase sales. It was an education and a wonderful experience. I agree with you. I loved being there. It wasn’t the most lucrative business. It was okay. We did alright, as we talked about. We weren’t losing money.

What you learn in that and by owning your own business, it’s wonderful. You have to want to put that time in as we’re talking about. It’s not a 9:00 to 5:00. They were nights there. The guys would come in. We were supposed to close at 6:00. I’m telling you, I didn’t leave there till midnight. I would prop the door open so people would know we’re still open.

Cars would come in at 8:00 at night and some of the guys from the Chiefs State Attorney’s Office would come in and they would sit. It would be midnight and we were still going. That’s the price of doing business, but our sales increase dramatically in the first twelve months as a result of that door staying open like that. The relationships and networking that happens in that is phenomenal.

When I went out of my own with my own law practice, I needed the work. If a couple wanted to meet at night because they were both home and the kids were up. I was going to meetings 8:00 at night in Saturday and Sunday. It made my wife crazy, but that was it. I would go meet with clients and I’d be checking the PO box every day. On Saturday, the letter and the check would come. I would sit Saturday night and Sunday, do all the work so I could “bill” and collect the money on Monday because I had to pay my mortgage.

In other words, you’re working just as hard if not harder but it’s for you and you’re building something. By the way, I’ve been getting an education from private equity people and investment bankers. If you can build something then it’s valuable. There’s an old saying, “If you work for yourself, you’re building your own future. If you work for someone else, you’re building theirs.” That is one way to look at it, but you’re right.

If you work for yourself, you are building your own future. If you work for someone else, you are building theirs. Share on X

To the point, if you are going to be an entrepreneur, understand you’re going to work as hard, if not harder than you’re working now. Probably harder but it is for yourself. On that note, by the way, for those of you who are married or in a relationship, it’s good to make sure your partners on board with that. As an accountant, I’m going to Leave the big firm and I’m going to be on my own. It’s great to have a plan, but I want to let you know.

What you will find is you got to do what needs to be done like staying at the cigar shop till midnight. Why? It’s because at 8:00 to 12:00, you got people coming in and you’re going to make your money. Running out on weekends, meeting with clients, staying up Saturday night getting stuff done and Sunday night getting stuff done. You’re going to skip the game. I didn’t go to some of the UConn football games. I had season tickets. I had to do work.

What you’re speaking to now, Eric, is work-life balance. I giggle or laugh when people talk about like, “I’m going to start my own business.” They then eventually work into a conversation about work-life balance and I’m like, “I don’t recall any balance.” It was 90% work and 10% everything else I had to split.

When I started at Deloitte as an intern, they took us all out the Scottsdale. They had a training facility there. They always brought in the managing partner from their LA office. I don’t remember his name. He’s a work out guy. A big guy, rode a motorcycle and had a component hill like long hair. He looked like a biker. He was the lead partner. He had a $10 million book of business. He was an animal in terms of business development and everything else.

Somebody stood up and asked him, “What do you do to maintain work-life balance?” At that point, that was becoming a thing. His answer was, “I have not.” He said, “I get up at 5:00 AM and I work out. That’s my work-life balance. After that, I’m going to work all day. I need to make sure other things are happening. I got client meetings at night. I may have to fly out to meet with a client the next day. If there’s work-life balance, I’ve never seen it or I’ve never seen it with anyone who’s ever succeeded.”

As we’re helping our readers, don’t talk like that work-life balance. If you want work-life balance, then you go get a 9:00 to 5:00 or an 8:00 to 5:00 or a 7:00 to 3:00 You can pretty much schedule around that. You make sure you’re expenses don’t exceed your income, which you can afford. You could maybe strike work-life balance if that’s what you want for yourself, but that is not the life of an entrepreneur particularly when you’re new.

 

The Success Tax Podcast - Eric Green and Tony Carter | Entrepreneur

 

Could you do that? Yes. I’m going to different position now. Let’s say my partners walked in here after this episode and said, “Get out.” My feelings would be hurt, honestly. We’re friends or I thought we were, but I’d be in business the next day. My clients are coming with me. I am in a position where I can have a Calendly or something like that, and I set my hours. By 5:00 PM I’m done. Also, if no one comes in that week it’s okay.

I’m telling you. You could start out and have parameters. It’s not a bad idea, but I have to tell you the truth. You’re going to probably find a client. You need the money and the client is not available when you think you want to be available. We’ve told new associates, “I will try not to bother you at night. I’ll try not to bother you on the weekend. I do want to respect your space and balance of some sort but you need to understand something. If the client comes in and we have a deadline on Monday, you’re going to be working that weekend.” There’s no other way around it.

That’s the nature of the business. If you don’t like that, don’t be a lawyer in private practice. Go to work for the government. Go to work for a corporation. Go find something else to do. Teach. I’m going to go back to that whole series we do with Rick Wells about Gameplan. Games have rules. When you’re going to go do something, investigate what you’re getting into. What are the actual rules?

I do get this. About once a year twice a year, I’ll get emails from law students who want to talk to me and I will always try to find 15-30 minutes sometimes to do a Zoom with them. I tell them, “Honestly, this is what I did. I have the book about building a million-dollar practice.” I’m pretty blunt about the good and the bad. When my wife read it, she said, “Are you sure you want to share all this?” I’m like, “Yes.” If nothing else, I’ll be honest. With the good and the bad that went through, the same with you. They are lessons. I agree with Tony on that one. If you’re going to go and be your own boss, start your own business, be an entrepreneur. Understand you were going to work at least as hard if not harder than you’re working now.

Don’t use language like work-life balance because there is none. Don’t set yourself up for failure by setting an expectation that is not real.

Do not set yourself up for failure by setting unrealistic expectations. Share on X

That also leads to what I mentioned briefly, understand something. Tony, and I had done an episode about the biggest mistakes entrepreneurs make. One of them was being undercapitalized. If you’re an army of one, if you’re in the business, you can’t be undercapitalized. What I mean is, can you live without a paycheck? There’s a pretty good chance you’re not going to get paid for a while. That might be a long while.

Do you have a partner or spouse and you can live on that income? Have you set aside enough money? You’ve got to have a plan. Now, when I left the big firm and went on my own, I had friends of mine. I told them my plan and they began introducing me to people. I have lined up about ten estate plans. I set up the appointments and then gave my 30-day notice, which I was required to. I was at a level where it was 30 days.

I have lined up some work out of the gate, but I will tell you. Out of those ten, two of them ended up backing out. They told me we had a date. They ended up canceling and never ended up coming in as clients. The best laid plans. You need to make sure that you can live without that paycheck for a while. When you buy a property, I’d love to know like, “I have a tenant since day one. They’re going to start paying me.”

That’s not real. If they pay you at all, depending on the tenant and the markets you’re in. Particularly with assets like real estate and how they perform, you talked about this during our last episode briefly, looking at being realistic again. You’re talking about paychecks now. If you’re in the real estate game, that’s your money. That’s your paycheck. You’re either going to make money by positive cashflow monthly.

My understanding is that’s probably going to be minuscule, depending in the game. You’re making money on a appreciation and value of that asset over time. I don’t know any other way to make money off of it. It’s going to take some time before you get one unit and maybe that unit is making you a few hundred dollars a month with positive cashflow on that after everything.

You get a second one, now you’re up to $400 to $600 a month. You get a third one, so on and so forth. Now you got something going there, but you always have to keep in mind to keep an eye on that asset to make sure it’s performing. It’s going to be a while before you’re able to collect real money, substantive money to help you live your lifestyle.

If you haven’t read, I urge anyone to read. Go back and check out those game plan episodes where Dr. Wells helped us break down. That is not just for a business. It’s for your own personal life. It’s everything. You need to have a game plan no matter what you’re going to do. This is one of them. If you just map this out, “This is what I want to do. This is how much time it’s going to take me. This is how much I’m going to have to carry this. By the way, I need to carry myself. How am I doing that?”

It’s okay to start as a side hustle but at some point, the side hustle either goes away and it’s just a hobby or you going to turn it into something. What tax rep network was, it was a means of marketing my law practice. I never thought tax rep itself would blow up and become a multi-million-dollar training program, which it is. At some point, I identified this is a real business and then moved into that and leaned all in on it. It’s gone very well. On that note, though, if you want to be an entrepreneur, you have to understand things sometimes don’t work out. I would always suggest you will fail.

It’s almost required at some point.

 suspect Tony can tell you about the bad real estate deal he got involved in. I am partnership. We were going to launch. I was going to automate the real estate closing business. I thought I had enough connections to get those. I was working with somebody and we were going to do this. We were ahead of our time but it was something we couldn’t pull off. I lost $10,000 or whatever it was over the course of the year and a half and it failed.

I never thought of myself as a failure. We just couldn’t put those pieces together and/or in some cases, I’ve had somewhere and we’ve talked about this. I can make it work, but how much effort, how many hours, and how much money? At some point, is this where I want to spend my time? If you’re going to be an entrepreneur, where you’re going to start something, your vision and your meaning.

You’re going to create something that other people don’t even know exists. You need to understand something. You got an uphill battle. There’s a chance it will fail, and that is a risk you’re willing to take. You’ve looked at it. You’ve considered everything and you make the decision to go. You go all in, but some fail.

They do fail, Eric. I was sharing with you that we started this book club probably at the beginning of the 2026. There’s a group of eighteen of us. Not all eighteen make it every time we have it. It was in between 6 to 10 people. It’s a good little group. the first book we read was As a Man Thinketh. I can’t help it when you start talking about this. I think about that book. If you go in the business for yourself, you have to own it.

 

The Success Tax Podcast - Eric Green and Tony Carter | Entrepreneur

 

You can’t be in the business of pointing fingers when things don’t go well because to your point, you have to expect it’s not going to go well. Realize that you are where you are in business for better or for worse as a direct result of your thinking. The way that you plan, which makes my next point. If you look at yourself or someone’s ever said to you that your executive function skills are lacking. Meaning how you regulate your emotions, your ability to focus and pay attention to things. Your ability to plan, to organize. If you are lacking in those areas, especially if you’re a new and a small business.

You better be realistic in your assessment of your own skills and get people on the team that can help you with those things like a bookkeeper. If you’re not good at that, you have to recognize you should not get into business for yourself if you have no ability to assess your own skillset. What that meaning is, where do I come up short in that?

I have an accounting background. I’m a tax attorney. I could do our bookkeeping but I don’t. It’s not a good use of my time and I’m not that good. I haven’t done it in 30 years. It’s something I couldn’t. Is that a good use of your time? When I talk to entrepreneurs and they’re doing everything like that. I would tell them, “Get the bookkeeping to a real bookkeeper.”

Honestly, why do you have that time? I have to tell you. Jeff and I don’t have enough time to continue marketing. We could do more marketing. Our time is better spent bringing work in to the firm and creating content for tax rep. if I’m sitting around and putting the bank transactions and all that stuff. That’s the stuff you give to a bookkeeper.

There are times when it’s not just time and value of money. If I need to get the business to a place and we talked about this. You have a dream, but when you break down what you need to do, now you have a plan. Your goal is to execute the plan. I’m willing to being the bookkeeper unless you’re building a bookkeeping business. It’s not part of it. Your focus has got to be all in on growing. We have to do a whole episode just on this. It’s the concept of look up, not down. Drive revenue.

Revenue is the lifeblood of your business. Don’t worry about, “I should cut the Wall Street Journal for $189 a year. I don’t want to pat $150 a month on the bookkeeper.” That is money well spent. Your job is to drive revenue. If you have revenue, now you’ve got cash. If you’ve got cash, you can hire help. You can spend more in digital marketing. We’re going to hold series on all of these things like digital marketing, revenue and all of that stuff.

Revenue is the lifeblood of your business. Share on X

The point is, your time is best spent. We haven’t talked about this, but let someone else do the bookkeeping. Tony’s got to be looking for the next deal. He makes money on the deals. Not doing the bookkeeping. Focus on pushing the top line up. When you go out, your job is to get clients, create the better product, keep improving on the product, watch what your competitors are doing and keep improving and moving.

With AI now, if you’re standing still, you’re falling behind. The point is, you’ve got to be willing to fail. That doesn’t mean you should just accept it. If it’s within your power to change it, do that. Make sure you have the patience in place, but you have to identify what your time is best spent doing and what is better off to push off to other people want to free you up. Honestly, my bookkeeper is better at it that I am. Dawn is doing my tax returns. She’s better at it than I am. Let them do what they do best. Let me go do what I do best.

I want to make the last point about self-assessment as a new business owner. You have to set your own skills. You have to be brutally honest with yourself in terms of, “This is what I’m good at. I can turn wrench. I can swing a hammer like nobody’s business. I cannot do books. I cannot do accounting. I suck at it.

I’m terrible at it.” Stay out of that. Give it to someone else. To your point, except that as a necessary expense of the business the same as you put fuel in your trucks or your car or whatever you’re driving to go to a job site if that’s the nature of your work. Having that bookkeeper on speed dial or getting them over your monthly bank statements is essential.

By the way, when we spoke about this, we had Dawn Brolin on the show. Know how to use your accountant, meaning I don’t want them just doing the books. I want the reports each month reasonably quickly after the month. I want to have at least quarterly meetings of where are we, what’s going on, and have they noticed any expenses getting out of whack. Again, I got so much going on. I’m not paying attention. I’ve had them catch. Who is this that they charge $375 to get credit card? I don’t know. As it turns out, it was something we were using but the name changed. They caught that. I wouldn’t have.

If someone got my credit card and they will whack me $200 a month, I’d never know. Now I’m losing $2,500 or $3,000 to some scammer and it’s only because it wasn’t big enough to hit my radar. The bookkeepers all over it. Not only you get the books done, but you need to be reviewing them. That’s the point. It’s the information they do. On Tonys point, understanding what you’re good at and what you’re not good at. If you’re going to then hire people, you can do it intelligently because they’re going to fill the gaps that you can’t.

If you will hire people, do it intelligently. They will fill the gaps that you cannot. Share on X

That’s it. That’s perfect.

Folks, we’ve told you why you shouldn’t be an entrepreneur. In all, honestly, both of us would tell you. You want to be an entrepreneur. In fact, many of us are going to become entrepreneurs, whether you want it or not. This is the world is headed. If you can’t sustain yourself or if you’re afraid of failure, I would start dealing with that stuff.

Lay the groundwork so that you can start this. Maybe it starts as a side hustle. If you’re having this incredible fear of failure, talk to other entrepreneurs. Join groups like the Freelancers Union or any of that so you can talk to other people. Unless you want to like open a casino, you don’t have to go huge. Many of these tax rep started as a side hustle. What I invested was time, which I was willing to risk. With that, hopefully we’ve told you why you shouldn’t be an entrepreneur in the hopes that you’ll deal with those things and become one.

Best of luck to you all.

Tony, thanks for taking the time as always. Everyone, thanks for reading.

 

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