Tax Planning Strategies for Small Businesses

The Difference Between Tax Preparation and Planning

For most business owners, business tax planning feels like something you deal with once a year, usually under pressure, and right before a deadline. That mindset is expensive. After more than 10 years as a CFO consultant and tax strategist, and previously serving as an IRS agent, I’ve seen the same pattern over and over: businesses don’t overpay taxes because the rules are unclear, they overpay because they’re reacting instead of planning. Real tax planning isn’t about loopholes, it’s about aligning how your business operates, pays people, invests, and grows with the tax code working for you instead of against you.

If you’re a California business owner, investor, or entrepreneur, capital gains tax isn’t just a line item it’s a strategic risk. I’ve spent over a decade helping business owners navigate capital gains planning, and one thing is consistent: most people dramatically underestimate how much California takes. Unlike the federal system, California does not reward long-term investing with lower tax rates. That single fact changes how you should think about exits, portfolio rebalancing, and real estate decisions. This guide breaks down how long-term capital gains tax works in California in 2025, where business owners get burned, and what you can do to keep more of what you earn.

Before I dive into some year end tax strategies East Los Angelesbusiness owners can and should be making, I want to address some rumors and misinformation about the SALT workarounds that are available to some of our clients (though not all). Essentially, 22 states (as of this writing) have enacted legislation that enables business owners operating in a partnership or S-corp to deduct their state and local taxes (SALT) beyond the 10K cap that exists on federal returns. These are the states that currently provide this workaround in some measure:

It’s Monday the 20th, as I put this together, and many of our East Los Angeles clients and friends are gearing up for a very different kind of holiday week. I’m very aware that while the holidays are a time of joy for many, they are just as often a time of pain for a significant portion of my contacts as well. That’s probably especially true this year. Missing loved ones, loneliness, and pain can sometimes be the most prominent decorations of this season, and if that’s the case for you, know that you are not alone and that you are loved and appreciated. Not only by us here at Team Gelfuso, but undoubtedly by more people than you could possibly imagine. THAT is the bottom-line, real-world truth, whether you believe it or not right now. And by the way, we are still meeting with East Los Angeles clients to help them with year-end issues, so feel free to use this: uplevelservices.com/contact/schedule-an-appointment/ (I can’t guarantee our availability, as we have a LOT of client work to handle these few days before year-end … but we’ll do our best!) And, while I often write about important business, financial, and tax-related matters, I thought I’d share with you my annual prayer for the holidays. It’s worth printing and clipping near your monitor, so you can remember it, even beyond this week. I can’t take credit for its authorship, and I don’t honestly remember where I got it. But it’s good.

These days, I’m often glad that it’s our busy tax filing season, so that I have an easy excuse when political conversations are happening: Oh THAT [crazy new political story]? Huh, didn’t see it — I’m too busy with tax season. With all of the chaos out there, the division and shouting — from Washington to Facebook to right here in Downey, it’s helpful to try to tune out the shouting and focus on what is actually in our sphere of productivity. So speaking of being productive, it might be time to get moving on your tax files, if you haven’t already. The IRS did a study a few years ago that computed that the *average* time that it takes to complete a tax return is 22 hours. And obviously, that number varies by the return, but I’m reminded (again) of the blessing that it is to free our clients’ TIME — not to mention the additional deductions we find, the stress we remove, and the security we can provide in knowing that it’s being handled right. Already, we have many, many Downey tax clients who have filed, have received refunds and have written us notes telling us that they’ve never been more pleased with their filing experience. And of course, this makes me happy, as you might imagine.Now, I’ve got something here that we posted towards the beginning of January, but as we are moving into the depths of March, I thought it would be worth posting once more… Christopher J. Gelfuso Tax Paperwork Checklist “We are not retreating — we are advancing in another direction.” -Douglas MacArthur With the increased penalties associated with the ACA in 2017, and all of the other changes every year, filing your taxes on your own is not for the faint of heart — even with nice-looking softwares on the market which purport to make it easy for you. But that’s what we’re here for. Let us be your easy button. Below is a list of what you will need during the tax preparation process. Not all of them will apply to you — probably MOST will not. Nonetheless, it’s a useful checklist. Before you get overwhelmed: yes, this is a long list — but it’s the unfortunate reality of our tax code that it’s not even comprehensive! But these items will cover 95% of our Downey tax clients. Really, this is for ensuring that we’re able to help you keep every dollar you can keep under our tax code. Even if for some strange reason you won’t be using our cost-effective services this year, feel free to use this list as a handy guide… Personal Data Social Security Numbers (including spouse and children) Child care provider tax I.D. or Social Security Number Employment & Income Data W-2 forms for this year Tax refunds and unemployment compensation: Form 1099-G Miscellaneous income including rent: Form 1099-MISC Partnership and trust income Pensions and annuities Alimony received Jury duty pay Gambling and lottery winnings Prizes and awards Scholarships and fellowships State and local income tax refunds Unemployment compensation Health Insurance Information * All 1095-A Forms from marketplace providers (if you purchased insurance through a Marketplace) * Existing plan information (policy numbers, etc.) * If claiming an exemption, your unique Exemption Certificate Number * Records of credits and/or advance payments received from the Premium Tax Credit (if claiming) Homeowner/Renter Data Residential address(es) for this year Mortgage interest: Form 1098 Sale of your home or other real estate: Form 1099-S Second mortgage interest paid Real estate taxes paid Rent paid during tax year Moving expenses Financial Assets Interest income statements: Form 1099-INT & 1099-OID Dividend income statements: Form 1099-DIV Proceeds from broker transactions: Form 1099-B Retirement plan distribution: Form 1099-R Capital gains or losses Financial Liabilities Auto loans and leases (account numbers and car value) if vehicle used for business Student loan interest paid Early withdrawal penalties on CDs and other fixed time deposits Automobiles Personal property tax information Department of Motor Vehicles fees Expenses Gifts to charity (receipts for any single donations of $250 or more) Unreimbursed expenses related to volunteer work Unreimbursed expenses related to your job (travel expenses, entertainment, uniforms, union dues, subscriptions) Investment expenses Job-hunting expenses Education expenses (tuition and fees) Child care expenses Medical Savings Accounts Adoption expenses Alimony paid Tax return preparation expenses and fees Self-Employment Data Estimated tax vouchers for the current year Self-employment tax Self-employment SEP plans Self-employed health insurance K-1s on all partnerships Receipts or documentation for business-related expenses Farm income Deduction Documents State and local income taxes IRA, Keogh and other retirement plan contributions Medical expenses Casualty or theft losses Other miscellaneous deductions We’re here to help. Let me know if you have any questions. Warmly, Christopher J. Gelfuso  (562) 259-7777   UpLevel Business Services  of Downey

I know your business. Because we deal with clients like you all the time, I’ve got a leg up on all those “gurus”, since I’m right there in the trenches with you. – Christopher J. Gelfuso Christopher J. Gelfuso here, your tax and accounting professional. I know that we haven’t posted much before, but starting this week I’m hoping that you and I can have a conversation about your business. You and I both see the headlines. Questionable government decisions, taxes sure to rise in the next few years (whether or not it will really help the economy) your clients and customers are feeling a new pinch, and, well… overall the deck is stacked against small businesses like yours and mine. Right there in your neighborhood, I know that businesses could use a “shot in the arm”. Not Just “Tax Tips”… As I look over business tax returns and the books of our clients and associates, I often find ways to help the bottom line with little-known tax savings, etc. But I also see that if I could help “fix” sales, marketing, management and leadership problems for my clients it would go a long way to help. I don’t pretend to have all the answers, but I’ll pass along what I’ve seen work for me, and for other clients like you. And, I’ll be frank…if I can help your business THRIVE during these economic times with my advice, it helps MY business. I like keeping my clients doing well, because it means that our services will be paid for! And as our clients grow their businesses, their need for our services also grows. It’s a true “win, win.” But the problem is that there’s a lot of confusion out there about how to grow your business right-with cost-effective, powerful strategies which cut through the clutter and create sales. There’s a ton of so-called “experts” out there, and they often give conflicting advice. So starting this week, we’ll be sending you notes and tips on a weekly basis-offering “Real World” Business Strategy (which you can use) and guidance for increasing sales, improving leadership, and all-around business growth and development. And I hope you’ll forgive me if I lay aside “accountant-jargon” and give it to you straight! Here we go… Christopher J. Gelfuso’s “Real World” Business Strategy First Steps in This Economy / Getting To Know You In the coming weeks, we’ll discuss both general concepts and specific strategies…but now, in this first week, here’s a good start (plus a question for you): The fastest way to fix financial problems in your business is to fix the sales problem. Yes, I know – everybody’s business is “different”, but I’ve seen it across almost every business category: Make more sales and a host of problems disappear. (Now for some of you, I know that your increasing marginal costs are making your sales less powerful, but we’ll address that in the future.) So how do you do that? Well, there’s obviously a bunch of good answers to that question-but for a quick surge there are three lists to get ahold of right now. Existing Clients “Lost” Clients Targeted Prospects The first one might be obvious, but I’m continually amazed at how many businesses don’t maintain good records of their current customers. These are the easiest folks to sell to again. They’ve already indicated interest in your business, and have demonstrated it with their wallet. Go back to them this week with a promotion just for them, and the results will be better than any other list. “But what if I don’t have a list?” Good question, and if that’s the case: start one now. Whether it’s by giving an incentive at the point-of-sale or client meeting to have them provide you their details, or if it just means hiring a high school kid to compile all the data for you – this list is your most important asset in your business. I’ll address the other two groups in the weeks ahead, as well as creative strategies for going after your existing customers, but I’ll leave you with this request: Help Us Help Your Business! Would you take a moment to drop us a line with one of the following? A) Let us know what kind of service you’d like to see us provide for you and your business in the future, which we are not currently providing you. Or B) Would you write me a quick note about how well we’ve already served you? Businesses like yours are looking for a good tax professional-and we’ve found that what business owners really want to know is what others say about us, not what we say about ourselves. Your note would really help! We’ll be back again next week! Christopher J. Gelfuso

Christopher J. Gelfuso here, your tax professional. I know that we haven’t posted much before, but starting this week I’m hoping that you and I can have a conversation. You see, there hasn’t been an environment like the one we’re now facing in this economy and in our nation for quite a while. The fact is-I know you’ve got questions…about personal financial strategy, about tax specifics and about how to steer your way through these times we’re living in. Not Just “Tax Tips ”… I won’t pretend to have ALL the answers, but I’m going to do my best to give you information from the “real world”. Yes, there’s a lot of so-called “experts” out there (theorists, authors, or multi-millionaire “gurus”) who make it their job to spout opinion. But more often than not, they don’t know what it’s like to face the things that you and I face-right here. I also want to give YOU the chance to contact my staff and me about questions you’ve been having. I’ve found over the years that people generally want more (not less) from their tax professional in terms of communication and relationship. So you’ll be hearing from us more. Bottom line: starting this week, we’ll be making a major effort to keep in touch with you on a weekly basis offering “Real World” Personal Strategy (not just pie-in-the-sky theory) and guidance for growing wealth, keeping sane in this world, and all-around personal development. And it will NOT be just tax tips (it’s our job to take care of all that for you anyway). Sure, there will be tax items you’ll need to know about-which we’ll send your way-but I believe you’ll find these notes to be interesting and useful on a variety of levels. So let’s get started, shall we? Christopher J. Gelfuso’s “Real World” Personal Strategy True Wealth / Getting To Know You In the coming weeks, we’ll discuss both general concepts and specific strategies…but now, in this first week, here’s a good start (plus a question for you): Christopher J. Gelfuso’s Thought: Learning to be content in all circumstances is the foundation for generating real wealth, especially in this economy. Why do I say this? Well, it’s my job to help people “ride out the storms” in their financial life. And I’ve noticed a very real difference between those that handle it well…and those that, well, don’t. See, relative to their income, the rich are frugal. They save and invest. They spend less than 65% of their take-home pay on day-to-day expenses. They save at least 10% in their retirement accounts and another 5% in taxable savings. They direct another 10% toward unknown big purchases. And they even live frugally enough to give another generous 10% to charities. Now-remember when I said this would be “real world”? The fact is, I know that you may not be even close to this, and you could even be feeling guilty right about now. That’s the LAST thing I want to do to you, but here’s what you CAN do right now: Set it as your personal goal to increase (or start) your household money moving in these directions: 1) savings 2) retirement 3) short-term (big purchase like a car or furniture) savings and 4) giving. This week, choose ONE of these categories and move money there, however small the amount. Then, when you do so-let somebody know you did it. Not to brag, but to settle it into your mind. You’ll find that taking a positive direction in one of these areas-even if it’s just a measly 5 bucks-will go a long way to increase your peace of mind. And with THAT peace of mind, you’ll handle the upcoming storms real well. That’s the Real World, my friend. And finally, my Question: How could my staff and I serve you better? Would you take a moment right now, to reply to this email with one of two things for me? Either… A) Let us know what kind of service you’d like to see us provide for you and your family in the future, which we are not currently providing you. Or B) Would you write me a quick note about how well we’ve already served you? Lots of people like you are looking for a good tax professional-and we’ve found that what people really want to know is what other people say about us, not what we say about ourselves. Your note would really help! Thanks! To your success, Christopher J. Gelfuso 

Our hearts remain with those in Houston and, now, South Florida, who has been dealing with such a massive disruption of their lives — and during a time of year that is already one of the busiest. The IRS has set up a “catch all” page for those cleaning up from Harvey, Irma, and other such disasters, and it can be found right here: https://www.irs.gov/newsroom/tax-relief-in-disaster-situations . And here’s a recent article that goes into deeper detail about financial and data recovery in the wake of disasters: https://www.accountingtoday.com/news/irs-offers-taxpayer-disaster-planning-and-recovery-advice-for-hurricane-irma And, of course, if you have been impacted by any of these disasters in any way, we are here for you (or for your friends)! Allow us to help you sort through the financial muck so you can better deal with all of the mess of cleaning up other aspects of your life. A quick reminder, before I get to my subject of the day. Friday, September 15th is the estimated tax payment deadline for the third quarter. These estimates are for people with income that is not covered by withholding through payroll. If you are an independent contractor or have your own business, call us to set up a much more convenient and potentially tax saving method of paying in your taxes! And, well, speaking of Downey businesses, I have too many friends who start one or seek to turn around a flailing one, using this principle as a guiding light. That would be a mistake. Why Price Reductions are Bad Positioning for (Almost) Any Downey Business “How many things in your life do you do automatically, routinely, that is a waste of time but you don’t take the time to remedy them?” -Robert S. Scott I discuss this all the time with my Downey business owner clients — how to price their services. You see, often, we might hear consumers say, “Well, I would buy it if it were in my price range.” And, that idea tempts many business owners to lower their prices–just to sell more products. However, as you already know, price reductions sometimes create more problems than they solve. For example, price reductions… * Decrease net profits * Lead to the purchase of lower-quality products * Increase customer demands to drop the price even lower! * Require even more sales to make up the difference in revenue * Need a larger quantity of products And, in the end, there will always be someone willing to go out of business faster than you. Remember this: price is not a benefit. The close of a sale is not determined on the cost of your product. If you truly “sell” your customers and prospects, they will purchase your products/services no matter what price you determine. That’s the plain truth — and you’ve probably seen it in your own purchase patterns. If a customer or prospect doesn’t buy — and they claim the cost had something to do with it — you can guess they probably wouldn’t have purchased anyway. As a small business owner, and marketer, your job is to sell your products and services. But the actual art of selling has nothing to do with the price of the product. By the time your contacts find out about the price, they should be determined to purchase no matter what the cost. So, find “real” benefits (value) to sell to your customers and prospects. Help them to see how great their life is with your product, and you’ve got a customer. Point out their current pain, and your contact will do anything to get rid of it. Set your prices and hold fast. If you’ve marketed correctly, you will still have customers anxious to do business with you. Price gouging is a horrible thing — but, really, that’s a bogeyman that lives more in our heads than in real life. Charge your worth. You deserve it. Feel very free to forward this article to a Downey business associate or client you know who could benefit from our assistance — or simply send them our way? While these particular articles usually relate to business strategy, as you know, we specialize in tax preparation and planning for Downey families and business owners. And we always make room for referrals from trusted sources like you. Warmly, Christopher J. Gelfuso  (562) 259-7777   UpLevel Business Services