How to Set Up Your Own Business and Save Taxes in California for 2024


As a financial planner who works with women and LGBTQ professionals, a lot of my clients are self-employed and small business owners. As a small business owner myself, I’ve had to figure out how to navigate the legal of setting up our business and hiring.  I always turn to Jaime Santos of Santos Walding LLP for help. Jamie is a native of the East Bay. She got her law degree at UC Berkeley and she has been in legal practice for 20 years. After working at top tier law firms she started her own law firm specializing in estate planning, business law, tax planning, and nonprofit management. So we wanted to invite Jamie here to talk to us all things self employed and small businesses.

In this 35-minute video webinar, Jaime answers the following questions and more. If you’re short on time, these key points in Q&A below are broken out from content of the video: 

Key Points



Jenni: I’m Jenni Dazols. I’m a financial planner who works with women and LGBTQ professionals. A lot of the people I work with are self employed and small business owners. As a small business owner I’ve had to figure out how to navigate the legal shenanigans of setting up our business and how best to structure our business. To figure out these questions Lisa and I turned to Jamie Santos for help. Jamie is a native of the East Bay. She got her law degree at UC Berkeley and she has been in legal practice for 20 years. After working at top tier law firms she started her own law firm specializing in estate planning, business law, tax planning, and nonprofit management. So we wanted to invite Jamie here to talk to us all things self employed and small businesses.

What are the steps to take as a solo practitioner, freelancer, or contractor to start your own business? (00:56)  

Jenni: So if we assume that we’re talking to somebody who is self employed…perhaps they’re a solo practitioner or maybe they have a few contracts or they’re thinking about starting their business….what are some of the things that they need to make sure that they’re putting in place as they start their business

Jaime: Okay, so as you can imagine, the world of business is, is quite large. So I’m going to sort of narrow my answer down to someone who’s going to be so starting a sole proprietorship. And that’s, you know, a single person who’s starting a business. They’re starting a business where they’re not going to create a separate entity, like a corporation and work under that, but they’re just sort of working for themselves.

They want to be their own boss. And the steps for that are, similar from state to state. And in California, it’s pretty set. The first thing you want to do is actually 1) Pick a name. You may want to use your own name. For example, my law firm uses my last name. Or you may want to come up with a creative name for your business.

So you think of the name and then the next step, which some people don’t tell you about, but I think is a good idea, is 2) Do a Google Search to find out if someone else is using that name, especially in your particular field or in your geographic area. You don’t want to run into a case where you think you’ve came up with the name and then you get a cease and desist letter the next week from this company that’s been in business for 10 years. 

So now you’ve got a name. If it’s not your own name, what you need to do is 3) Register that name as a fictitious business name. And the place that you do that is with the county recorder. It’s one page application you walk in you put in the name you give them 20 bucks I think and now you have a fictitious business name.

4) Get a Business License. Then you got to think about licenses permits and zoning clearances, right? So depending on what kind of business you are you may work from home. You may need to work in an office. You may need a retail space. All this stuff is really dependent on what you’re going to be doing for business. And so you have to think about licenses and permits. Now, a lot of people ask me, like, do I really need a business license if I’m going to be working from home? And my answer is 99 percent sure the answer is yes unless you live in an unincorporated town or village your city has regulations about running a business. So check in with the city you live in. If you’re working from home, check in with the city that you plan on running your business in if it’s not from home.

And then another good idea would be to 5) Apply for an Employer Identification Number. It’s a tax ID number that’s specific for your business. It helps to separate you from your business. So, for example, if someone needs to give you a tax form at the end of the year, you don’t have to go around giving everyone your social security number. You can give them your business’s tax ID number and keep yourself a little bit separate.

Let’s see. Finally… If you plan on having employees, since you mentioned employees, you would need to 6) Register in California with the Employment Development Department. That’s the EDD. And they’re responsible for taking out from people’s pay paychecks, they’re responsible for taking out unemployment insurance disability insurance payments, etc. So every time you hire a new employee, you need to reach out to them and let them know about that.

Jenni: Okay

Jaime: And that’s the simple version.

Jenni: So if I’m living in Oakland or I’m living in San Francisco, I gotta make sure I have my business license.

Jaime: For sure.

When should you consider forming an LLC? (04:48

Jenni: Alright so now I’ve got my fictitious name. I’ve registered myself. Now there’s the question of business structure. So when should I consider becoming an LLC versus just a sole prop?

Jaime: Right. So LLC stands for Limited Liability Company. And it’s an entity. It’s something separate from you. So in California, the Secretary of State regulates entities, whether they’re limited liability companies, corporations, and a few others. And in exchange for paying them a fee every year, the state provides you with a shield from liability. What that means is that unlike when you’re sole proprietor and you are not separate from your business, your LLC is now a separate entity from you. What people are interested in doing when they seek out becoming an LLC is saying, “Well, if my LLC gets sued, I don’t want people to reach my personal bank account.” That’s the main reason for setting up an LLC.

Some people can’t set up an LLC, so I just want to throw that out there. Professionals, anyone with a license such as doctors, lawyers, architects, and therapists have to start a different type of organization, but you can still get protection.

Finally, the protection’s not absolute. You’re protected from things like if you made a mistake and someone lost some money. They could sue you. If you were really wrong and they won their lawsuit, they can have the assets you have in your business. They can have your cell phone. They can maybe have your desk. But you don’t have a house in there so they can’t get to your house.

But now let’s say that in your business you got “a little extra” one day and you actually attacked a client. Now, if you cause physical harm to someone, they can actually reach outside of your business and take your house. So just, you know, be cool and don’t lose it with your clients.

Jenni: I also understand one of the biggest things that LLC is that it protects you if you had taken debt out and then you default on the debt.

Jaime: That’s right. As long as you don’t personally guarantee the debt, as long as the debt is purely in the name of your business, then you’re not on the hook for it personally, just the businesses if you have an LLC.

Jenni: If you have a sole prop?

Jaime: There is no separation between you, you and your sole prop. You are one in the same. You’re in the mirror. It’s just you.

How can you set up a business with a partner? (07:25)

Jenni: If I’m starting a business with someone else what are my options?

Jaime: Right. So before we had entities like LLCs and corporations, we just had general partnerships, right? You could, you could get together with someone and create a partnership with a contract without a contract. You could still do that. You could also have the option again. With the state of California to create an LLC, but this time you can do it with another person, two other people, any number of people.

This is called a multi member LLC, and then, of course, you can start a corporation with, with someone else. So there are definitely options. Some require this extra step with the Secretary of State. Some require just making an agreement with your partner.


What are the differences between C Corp and S Corp? (08:07)

Jenni: Let’s talk about corporations. So there’s regular corporations and there’s S corps. So can you tell us a little about the difference of those and what we should be thinking about?

Jaime: So a regular corporation is known as a C Corp. The C just stands for the section of the IRS code. This is sexy stuff here. The section of the IRS code is Section C. So, that kind of corporation is the one that you think about when you think about Coca Cola, YouTube, Google. These are all C Corps. They have shareholders. And they have a board of directors. The shareholders own the company. The board of directors runs the company.

Everyone loves to learn about S corps because they probably have seen a lot of ads targeted at them as a small business person saying they can save lots and lots of tax money. I’ll tell you right now, I’m not a big fan, but it can work for some folks. An S Corp is not an entity. An S Corp is a way of being taxed. So you can take a regular C Corp, you can even take an LLC, and you can go to the IRS and say, “Hey, I would like to be taxed like an S Corp.” And then the IRS gives you the ability.

They placed this label on you, “S Corp,” and now you’re taxed as an S Corp. What’s the difference in taxing? You probably heard that C Corps get double taxation, and people complain about that sometimes. The corporation, because it’s separate from its shareholders, pays tax on its profits. And then is pays dividends to its shareholders, so it basically gets taxed twice.

An S Corp is kind of hybrid company that allows you as either a single person or as a partnership to be treated sort of like a hybrid between a corporation and a regular company.

So instead of being taxed twice, you’re only taxed once. And there is a potential for savings by being an S Corp.

When is it worth setting up an S Corp as a small business owner? (10:31)

Jenni: So these ads that are targeted to small business owners that are talking about how S corps are going to save them money…what are they talking about?

Jaime: When you are self employed you pay tax. Everybody who earns money in the United States pays tax. A self employed person pays income tax and what the IRS likes to call “self employment tax”. Self employment tax is nothing more than Social Security and Medicare and everyone pays it if they’re earning money.

Okay, now, in comes the S Corp. The way that the S Corp is structured you must become an employee of your own S Corp and you remain a shareholder of your S Corp. So you’ll earn part of your money as an employee and you’ll earn part of your money as a shareholder earning dividends, or in this case, we call them distributions.

Over here, you’re going to pay Social Security and Medicare tax. Self employment tax. Over here, you’re not. So the difference is, how much can you get paid as a shareholder and save in those taxes? And the answer is you save about 15.3%. And, therefore, if you’re  making $30,000 or $40,000 a year over in this bucket, you’re going to save a few grand.

The flip side, or at least the trade off, is that it’s harder to run an S Corp. There are more rules and there’s definitely more risk involved. The IRS pays more attention to S corps than they do to sole proprietorships. So, even though the risk of audit is still low for most people, it’s a little bit higher for an S corp than it is for a sole prop.

So you have to weigh the pros and cons. If you’re going to be saving $4,000 a year is that worth all the extra work? For some people the answer is yes, absolutely. I need those $4,000 to live on. For other people it’s maybe I should wait and think about this a little bit more.

Sometimes there is a sweet spot in terms of like how much money your business is earning. So if your business is only earning $40,000 or $50,000 a year, I would never advise you to start an S Corp. I would say you’re going to spend money and you’re not going to make it back in the savings. On the other hand, once you get up to $80,000, $90,000, $100,000 then at that point the scales start to tilt a little bit and you really could do some analysis and figure out if it’s a good time for you to jump into an S Corp.

I mentioned that what you’re earning over here, in this bucket, you’re earning as an employee. Well, the IRS says what’s keeping you from like paying yourself $10 as an employee and taking everything as distributions? Well, what’s keeping you from doing that is the law. The IRS says you have to pay yourself a reasonable salary. And even though they don’t define what reasonable is they tell you how you need to figure out what reasonable. So they look at geography, what it is that you’re performing, and what your business does. Do you have any employees who are also earning money for you? Are you the only person responsible for making the money in your company?

So while having something like earning $10,000 and paying yourself out $90,000 that might be reasonable in some universe where you do very little and you hire lots of other people to run your company. But in the case we’re talking about now where we’re talking about one person or maybe two or three people in a multi member S corp or multi shareholder S Corp, it’s never going to be like that. People are going to be at the 50% threshold, or even more, 60%, 70% percent salary versus distributions. So, now this pot over here where you’re saving money is getting smaller and smaller.

Jenni: Gotcha

Jaime: But, it does work. I mean, it can work.

Jenni: Then tell me too about the California Franchise Tax for S Corps

Jaime: Right, the extra costs. When you’re a sole proprietor, you’re filing one tax return with the IRS and one tax return with California. When you bring in this S corp idea, you’re already an entity. You’re an LLC that became an S corp. That S corp now has to file its own tax return. It has to file a federal tax return. It has to file a California tax return. So there’s extra expense there. It also, it doesn’t pay federal tax, but it does pay California tax. And the way that that California tax is calculated is there’s a minimum of $800. It can never be any less. If your S Corp makes $0, how much do you pay? $800. If your S Corp makes about $60,000, how much do you pay? $800. And the more that it makes, the higher that amount goes. I think the threshold is around $66,000. After that, it pays 1.5% percent on every dollar that you earn. So, more taxes.

Jenni: You’re going to pay on this franchise tax which is extra for being an S Corp as well as the added tax filing expense. Then there is the headache of having to figure out how to pay yourself the salary and set up payroll to do that. You also have to be more mindful about how you expense things. I’ve heard something about an accountable plan. Can you tell us about that when it comes to expense?

Jaime: Sure. So when you’re a sole proprietor, and let’s say, you drive your car for business you keep track of your mileage. At the end of the year when you’re filling out your tax return, you get to take a deduction for the value of that mileage that you drove. You don’t have to have your company pay you back for the miles that you drove or pay you back for the gas, but you get a deduction for it.

So now in an S Corp you’re not actually self employed. You’re an employee and you’re a shareholder. You can’t just deduct your use of your car because it doesn’t belong to the S Corp. Instead, you need to ask for a reimbursement.

So imagine you, you work for a company, right? It’s not your company. You’re working for Google. Google says, “hey Jen, I want you to  take your car and go run this errand. Then let me know how many miles you drive and we’ll pay you back on your next paycheck. So you’re getting a reimbursement for that. It’s exactly what you need to do now for your own S Corp.

So an accountable plan is nothing more than a reimbursement plan. It’s called an accountable plan by the IRS. You’ve got to have certain things in place for the IRS to recognize it as valid. I won’t go into the list, but you know, basically you need rules and policies in writing. And you need to make sure that your employees are asking for their money, like every month or every two months. You can’t wait till the end of the year and pay yourself for all the miles that you drove.

So it’s extra bookkeeping on the part of you as an individual. It’s extra bookkeeping on the part of you as your S Corp. But the good news is if you have the money and the S Corp to pay you back, it’s one way of getting money out of the S Corp and into your pocket. So that in addition to the salary that you’re earning, you can be reimbursed for your home office expense. You can be reimbursed for the business use of your phone, for the business use of your car. If you make a mistake and take a client out for a business meal and you use your personal credit card, it’s a way to get reimbursed for that from your S Corp. So it has its, it has its benefits. It is just more work.

Jenni:  So it sounds like with the S Corp the main benefit is you can save potentially on self employment tax, but there’s all of these other headaches. So if you were talking to somebody what would be in total net income of a small business where it makes sense to consider an S Corp?

Jaime: Yeah. If you are a single person, right? So if you were a single member LLC and you are thinking about becoming an S corp, I’d say if you’ve got consistent profits of about $80,000 a year. Go talk to your CPA, go talk to a business attorney about figuring out if it’s the right time for you. You don’t need an attorney to do it. It’s an election that you can have your tax preparer or your CPA bake or you can do it on your own. But definitely get some advice about what the rules are.

What are the most frequently missed opportunities for expense deductions in small businesses? (19:31)

Jenni: Let’s switch topics to expense deductions. Although there are a lot of headaches to owning your own business, the positive is that you can expense the cost of doing business and this can dramatically help your tax situation. So what do you see are the most frequently missed opportunities?

Jaime: So I feel like there are at least at least two different kinds of small business owners, right? There is the person who thinks that everything is deductible including my sandwich that I eat at my desk during the day and the person who thinks the only thing deductible is rent, right? Or maybe the cost of a computer that I do nothing with except for my business.

And the truth of the matter is that it’s somewhere in between. I like to tell people what the actual law is because I find it helpful when they know what the law is. So, according to the IRS code, in order for an expense to be deductible as a business expense, it has to be both “ordinary and necessary” for your business.

That is the definition. So what does that mean? It can mean a lot of different things for a lot of different businesses, right? But the way that I like to think about it and I advise people is to think very, very expansively about what is ordinary and necessary for your business. So something that’s ordinary just means that everybody who is an attorney or everyone who’s a financial planner can expect to have this kind of expense.

Something that is necessary is something that is particular to the way that you do something. So the example I like to give is let’s say you run a yoga studio. What’s ordinary expense for a yoga studio? You’ve got rent, you’ve got yoga mats, you’ve got water, you’ve got statues, you’ve got incense, you’ve got candles. These are all ordinary. You see them in every single yoga studio. And you can expect to be able to deduct that.

But now let’s say you’ve jumped on the bandwagon and you now want to offer “goat yoga” at your yoga studio. You need goats, right? And so you need to rent them, lease them, and buy them. You need to understand goat behavior. You might need to go to the petting zoo and pay five dollars to get into the petting zoo. You may need someone to train you on how to use those goats. Now, not every yoga studio needs that, but you need it.

It’s “necessary” for what it is that you do. So what I tell people is to think about not just who they are and what they do, but what’s the whole story about what it is that you provide. What is it that you’re providing to your clients? You’re sharing your experience with them. You’re sharing your knowledge with them. You’re sharing your research with them. You’re sharing a lot of things with them. Think about everything that goes into who you are in order to provide your clients the experience that they’re having.

It’s your narrative, right? If you are ever, unfortunately called to be under audit under the, to the IRS, just showing them their numbers, isn’t going to help you. They’re going to ask you questions about your business. You know, they’re going to say, what is this entry here for goat food? I don’t understand this. Right. And it’s your responsibility to have that narrative and have that narrative ready to be able to explain to the IRS why that expense was necessary.

So, think about who you are and come up with a narrative of why you need these expenses. You’ll find a whole bunch of expenses that you didn’t realize you could deduct. So, if you are a therapist, and your clientele are children, you may tend to go to Pixar movies a lot.  This example happens to me every time I work with with a therapist professionally. I ask them, “have you ever gone to see a Pixar movie and walked away thinking you could use that in a session with little Susie or little Mark?” And every single time they say, “yeah, I do that all the time.” Well, that movie now just became deductible. And they hadn’t thought about that before. But that’s a tool that they’re using in their therapy.

So think about it expansively. Who are you? What do you do? What do you bring to your clients? And you’ll find lots of expenses.

What business expenses raise red flags for IRS audits? (24:21)

Jenni: That’s really helpful I haven’t thought about that in that context. So is there a percentage in which you will start raising red flags? Let’s just say you’re deducting 80% of your business income. Let’s pretend you earn $100K and you’re deducting $80K. If there a percentage that raises red flags that could cause an audit by the IRS? What expense categories raise red flags that could cause an audit?

Jaime: Yeah. So I don’t have an actual answer for that. There are plenty of companies that don’t make a profit. What the rule with the IRS rule is, is that if you don’t show any profit for more than two out of five years, they can send you a letter and say, “Hey, we think that you’re not actually a business. We think you’re a hobby.” But you can actually respond to that. And if you can show them facts and evidence that you are actually a business, maybe you’re just, you know, ramping up, or maybe you’re having a bad few years then you’re not going to get in trouble.

So how do you prove you have a business? You have a website. You have business cards. You have advertisements. You buy things for your business and you really try to sell them or try to sell services. So the answer to “how many expenses can you take?” is that the IRS says you have to take all the expenses you have. You can’t hide them. Not only do you have to let them know about all of the income, you have to let them know about all of the expenses.

But your second question about particular categories. The categories of expenses that the IRS is most concerned about because they get abused the most are things like travel and meals. I have experience talking with IRS agents where they’ve told me that the reason the audit was happening was because this particular person had almost 40% of their expenses on travel in that particular year, and that set up a red flag.

Now that’s not enough. I don’t want to scare people, right? That’s not enough necessarily to become a target for the IRS. You still have to have bad luck, right? You still have to have your name pulled out of a hat. But that’s what puts your name in the hat. So travel, meals. It used to be home office, though I think COVID changed the way we think about that. Everyone, including me, has a home office, right? So I think the IRS has sort of taken their foot off of that pedal for a while. But just again, if as long as you have your narrative and as long as you have the proof that you spent the money and what you spent the money on, you will survive an audit.

Let’s say the IRS is interested in this $20,000 trip that you took in 2023 and that was for business and you have the receipts and you have in your itinerary all of the business contacts that that you met with while you were on your trip. That’ll be the fastest audit in history. You’ll be out in a few minutes because you’ll be able to just show them that it was valid. So I wouldn’t worry about it so much.

Jenni: That’s helpful

What tax considerations should people think about if they are a U.S. business owner and spending significant time living abroad? (28:08)

Jenni: My last question is kind of a one off, but I do think that there are people who do this, including myself, who are running a business that operates in the U.S. and their clients are in the U.S., but they’re traveling a lot. Part of the reason they’re doing this is for lifestyle flexibility, spending a big chunk of their year abroad or maybe they even consider themselves residing abroad. Is there anything that they should be aware of running a U.S. business like this from a legal or tax standpoint? 

Jaime: Well, the first thing that comes to mind is the dyed in the wool rule is that no matter where you earn your money, if you are a U.S. citizen or a U.S. permanent resident, it’s going to be taxed by the U.S. So, if you have your business, but you’re off in Athens, hanging out there for a few years, you still have to file tax returns.

And if you’re earning that’s taxable that income will be taxed by the U.S. Where it gets complicated is if it’s also being taxed by the place that you’re living or traveling in you may not necessarily be double taxed. So for example, I said Athens, right? Greece and the United States share a tax treaty where they each say, well, hey, if someone’s paying you tax on Greek income, we’ll give them credit for it. And the U.S. says, okay, if you’re paying Greek income tax, we’re going to give you credit for that. So that’s the good thing about it. 

Generally, you find out pretty quickly which countries around the world have higher income tax rates than the United States. Usually we’re on the low end compared to especially European countries. So, yeah, you’ll have to file a tax return and you have to pay tax, and it just matters where you’ve paid tax first. If you already paid it where you’re living, the U.S. will give you credit.

What paperwork do I need when hiring contractors both in the U.S. and abroad? (30:10)

Jenni: So speaking of abroad, I know that a lot of self employed folks who may hire contractors who live abroad. Maybe they found them through Upwork. Maybe it’s a virtual assistant or a product designer who lives abroad to support them in their business. What steps what things should they be considering?

Jaime: Okay. So you’re a U.S. business and you’ve hired a contractor and they’re not physically in the United States. The first thing you need to know is are they a citizen of the U.S., or are they “a foreigner” when it comes to income tax. So anyone who’s not a citizen or a permanent resident of the United States is considered a “tax foreigner”.

If they’re a U.S. Resident, you have to collect a W-9 from them, just like if they were physically in the United States. A W-9 collects their social security number, and their address. It’s a way for you to be able to report how much you’ve paid, if they’ve earned more than $600 during the year. You report that to the IRS, and the IRS is then expecting to find a tax return from this person, even though they’re living abroad.

For the foreign contractor the only difference is you want to collect a W-8 instead of a W-9. So if someone is a U. S. citizen, you get a W-9. If someone is a foreign citizen, you get a W-8. And depending on what kind of organization you are, you may have to collect withholding taxes from the U. S. citizen, but you would never have to do that from the foreign citizen. The rules are kind of complicated.

The other thing I want to say is regardless of what your contractor is going to be doing and whether they’re U. S. citizen or foreign citizen, I highly recommend always having a written contract. It’s going to benefit you multiple times over.  Number one, just to have clarity in what the expectations are with your contractor. But also, especially in the state of California, the rules about independent contractors versus employees have shifted and become so strict in the last few years. You really want to make sure that you have a contract and that it is valid under California law.

Jenni:  Thank you. That’s actually really helpful. Thanks Jamie.

Jenni’s takeaways (32:42)

Jenni:  So I hope you enjoyed that conversation with Jamie. Here are my big takeaways: 

If you’re self employed or thinking about self employed, you’re going to want to be thoughtful about your business structure, as this has big implications on the legal and tax side of things. The default for anyone starting is to become a sole prop, but I would advise that if you’re serious about your business, even if it’s just a side gig, it’s worth considering whether an LLC makes sense for you. That’s because an LLC separates your business assets from your personal assets. And that can be very important in protecting you from financial and legal liability.

As for S Corps so there is potential tax savings to be had by becoming an S Corp, but there are also… extra costs. So you’re going to want to be making at least $80,000 in net income. That’s net income after deducting all your business expenses to start for this to even start making sense.

Regarding business expenses and what’s taxed, what’s deductible, my biggest takeaway from Jamie was be expansive in how you think about it. So if spending money on XYZ can support the narrative of what you’re doing with your business, then yes, it can be considered a business expense.

Beyond these issues, there’s also a lot of other issues that are probably top of mind for you as a self employed person. These might be things like, 

  • How do you best manage cash flow? Especially when your income and your expenses are variable.
  • Do you have a backup plan for emergencies, both personally and business wise?
  • How much of your profits should you be investing towards your business goals versus your personal goals?
  • What is the best way to save if I’m self-employed? Is a SEPs, solo 401k, or simple IRAs best for me?
  • Tax planning. How do you project how much you ought to be paying in estimated tax? How do you make sure you have cash flow to pay that so you don’t avoid a big tax surprise and not have cash to pay for that.
  • Are you capturing all of the potential business deductions? What about the qualified business income deduction?
  • Health insurance. How do I get health insurance if I’m self employed and not working for someone else?

Jenni: So, yeah. It, if you’re your own boss there’s a lot of freedom in that, but there’s also a lot more questions and room to optimize for that. If you want a sounding board to talk about any of these things, feel free to reach out to me. I specialize in helping self employed women and LGBTQ make a plan for your money so that you can feel confident about your financial future while having the freedom to work and live on your terms. So please reach out. And I’m happy to do a free consultation with you. Thanks.