THE TAX IMPLICATIONS OF YOUR SIDE HUSTLE Many taxpayers have side gigs that have a significant impact on their taxable income. From Uber drivers, to carpenter contractors, to horse racing, to manufacturer reps, to part-time real estate agents, to organic beef farms… you name it, and we’ve probably seen it. And from a tax-compliance standpoint, there is an important distinction between hobbies and businesses that are operated with the intention of earning a profit. Understanding this distinction could save you thousands of dollars come April 15th. Hobby Loss Rules: If an activity is not intended to earn a profit, losses from that activity may not be used to offset other income. The ability to deduct losses on your tax return will ultimately be determined by the Internal Revenue Service. If the IRS determines that the taxpayer did not enter into the business activity with a profit motive or that the taxpayer continued losing money in an activity with no intention of ultimately making a profit, the taxpayer will lose the ability to deduct those losses. These rules apply to individuals, partnerships, estates, trusts, and S corporations. Hobby or For-Profit Business? When determining the real intent of the taxpayer’s activity, the Internal Revenue Services will look at a number of factors in assessing whether or not the activity is motivated by profit: ​ whether the activity is conducted in a professional, businesslike manner the qualifications of the taxpayer or the taxpayer’s advisors the amount of time and effort spent by the taxpayer or the competency of the taxpayer’s agents and employees the potential for appreciation of the venture’s assets the taxpayer’s history in operating other businesses the taxpayer’s success or failure with the particular activity the ratio of profits to losses and how that compares to the taxpayer’s investment in the enterprise the financial status of the taxpayer, the economic benefit of the losses, and the taxpayer’s primary source of income the personal pleasure or recreation the taxpayer derives from the activity ​ While the taxpayer must engage in the activity with a genuine profit motive, a “reasonable” expectation of profit is not required if the probability of loss is much higher than the probability of gain. The IRS will likely view all the facts and circumstances to make their decision, but more weight is given to objective facts than taxpayer statements. One simple way to get off the radar screen of the IRS is to show a profit. If the gross income from the activity exceeds deductions for three out of 5 years, the activity is presumed to be conducted for profit. Read more articles Failing to order your affairs to minimize your tax burden could cost you significant money - so don't wait to take action. If you have additional questions or need some planning help, please reach out to us.

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WHITE PAPER INTRODUCTION WIN ONE, LOSE ONE, WIN ONE... The W-L-W case was a fun case for our team. There was complexity due to the types of income this family was generating and the stakes were high because they were in the 39.6% tax bracket in the prior tax year. They were also paying AMT (the alternative minimum tax). This can be a very tough tax to deal with because it can wipe out our ability to take certain itemized deductions. ​ Both the husband and wife worked. The wife was a high-producing business owner and the husband worked in corporate America. We projected their tax liability to be in the $110,000 range when we started the case, and both the husband and the wife made it clear that they were tired of paying too much in taxes. They felt like their current advisory team was doing little to help them accomplish their goals. THE CHALLENGE With more than half of the income in this case coming from W-2 income, we believed we could still make a difference for this family. This, however, was one of the first cases where the majority of the income was not coming from the small business owner, but coming from a corporate employee. THE SOLUTION We had three goals heading into this case: Lower their taxable income by $15,000 Shift the sources of the income of the business owner Reduce or eliminate the AMT Penalty ​ ​ In the end, we could not get to our first goal and we did not fully eliminate the AMT penalty. However, we were able to lower their taxable income by $12,500. ​ We were surprised at the smaller impact we had on their taxable income, but we were even more surprised when we discovered that we lowered their overall federal tax liability by $14,000 a year. ​ We were not able to fully eliminate the AMT penalty for this family, but we were able to reduce it with two strategies: We reduced their adjusted gross income by structuring the compensation differently for the business owner and this lowered the AMT penalty We suggested shifting one asset from their personal balance sheet to an LLC. This reduced the portion of the itemized deductions that they missed as a result of the alternative minimum tax. The $14,000 in annual savings that we were able to generate for this family was outside the norm of what we had done in the past, but the additional complexity of their situation gave us more opportunities to be creative!​ Save as PDF More White Papers ​ JSZ: Junior Sam Zell CWS: Could-A-Would-A-Should-A SOO: Starting Over, And Over

JULY 2016 MONOTELO QUARTERLY ARE YOU PROTECTING YOURSELF From Your Corporate Income? ​ While there are potential tax savings with a corporate structure in place, it is critical that the corporation be the entity that actually earned the income. ​ WHAT DOES THAT MEAN? A fundamental principle of tax law is that income is taxed to the entity who earns it; and any attempts to divert the income away from its true earner are not recognized by the IRS. AND WHAT DOES THAT MEAN? It means the corporation (not the business owner) must be the entity that contracts for the services that it will have you (the business owner) provide. It means the corporation needs to be the entity that gets paid (not the business owner) for the services provided. It means the corporation must have control over the income it receives. Once it receives the income, it can then direct it to the business owner via payroll or a shareholder distribution. ​ WHAT ARE THE MAIN TAKEAWAYS HERE? If you have self-employment income, you should consider the potential tax benefits of a corporation At Monotelo, we believe that clients who have self-employment income should consider the potential benefits of structuring their business as a corporation. That is because a corporation can provide asset protection and potential tax benefits that are not available to the self-employed individual who files a Schedule C with their tax return. 1. Have your clients or customers write their check directly to the business. Do not accept checks written to you personally. A check made out to you and signed over to the business puts the business owner at risk of double taxation and penalties. ​ 2. Have the corporation pay you a salary for the services you are providing to the corporation. ​ 3. Make sure that all contracts and agreements with clients are between the client and the corporation, not between the client and the business owner. Save as PDF October 2016

September 2019 SMALL BUSINESS TIPS Quarterly: Oct 17 How Will Your Real-Estate Sale Be Taxed? When you sell real estate property other than your primary residence, the tax implications of that sale depend on whether it qualifies as dealer or investor property. Each of these classifications is taxed differently and carries its own benefits and drawbacks. ​ Dealer Property: Property you hold for sale to customers in the ordinary course of a trade or business is considered Dealer Property. House flipping is a common example of dealer property because you purchase the property with the intention of fixing it up and selling it for a profit. ​ Profits on dealer sales are taxed at your ordinary income rate which can be as high as 37 percent and are also subject to the self-employment tax of 15.3 percent. Dealer sales cannot be used in 1031 exchanges to defer taxes by reinvesting in another property. ​ One advantage of dealer sales is that any losses on a property are considered ordinary business losses which can be fully deducted in the year of the sale as opposed to capital losses on investment property which are limited to $3,000 per year. ​ Investor Property: Property that is held to produce income or long-term appreciation is considered Investor Property. Rental properties are the most common type of investor properties. ​ Profits on investor sales are taxed at capital gains rates which are capped at 20 percent if you own the property for more than one year. Investor property sales are also not subject to the 15.3 percent self-employment tax. ​ The cost of investor properties can also be depreciated over the useful life of the property, although the depreciated cost will need to be recaptured at the time of the sale. Investor properties qualify for 1031 exchanges which allow you to reinvest the profits from the property into a similar property and defer the taxes on the sale until you sell the new property. One disadvantage of investor property sales is that the deduction for capital losses is capped at $3,000 per year unless you have capital gains from another sale to offset the losses. ​ Generally speaking, if you sell a property at a gain you will receive favorable tax treatment if the property is classified as investor property and if you sell a property at a loss you will receive favorable tax treatment if it is classified as dealer property. ​ Classifying Your Property Sale Identifying the correct property classification is not as simple as determining which will give you better tax treatment. In classifying your property sale the IRS will look at multiple attributes of the individual sale and your overall situation: ​ Intent: One key area the IRS will look at when classifying your property sale is your original intent in purchasing the property. If you purchase a property with the intent of fixing it up and reselling for a profit, then that property is considered dealer property. If you buy a property with the intention of fixing it up to operate as a rental property it will be considered investment property. Even if you sell the property before collecting any rent you can classify it as an investment property if you can demonstrate that your original intent was for it to be a rental property. Documenting your intent at the point of purchase is critical to defend your position before the IRS. Holding period: Generally speaking, the less time you own a property before selling it the greater the chance the IRS will classify the property as a dealer property. Frequency of property sales: If you are regularly buying and selling properties you are likely to be classified as a dealer. “Making a Living:” If a significant portion of your income is made through buying and selling properties you are more likely to be classified as a dealer. ​ These attributes are examples of what the IRS looks at to classify your property sale but not a definitive list. There is no standard formula to follow and you need to evaluate the characteristics of each property sale on its own. Understanding the distinction between a dealer and investor property can help you avoid surprises in tax season. Proper planning and record-keeping can also ensure that you receive the best tax treatment available to you when you sell your property. ​ For help determining how your property sale should be classified, please reach out to us. Previous Article

Quarterly: Oct 17 ...Better Decisions This article is the second part of our series on decision making. Applying some of the information from Thinking, Fast and Slow, we are diving into the research from Nobel Prize winner Daniel Kahneman and how he breaks down our decision-making process into two systems. ​ Notes from Better Thinking... : ​ To keep things simple Kahneman breaks down our thinking process into two systems that he describes as “System 1” and “System 2.” System 1 is intuitive and emotional, fast and easy. It is reactive. “There was a shark attack last week, I am never going to the beach again.” System 2 is deliberative and logical. It is also slow and requires effort. “What are the chances of getting attacked by a shark? Is swimming in the ocean more dangerous than swimming in a community pool?” The challenge with our System 1 and System 2 thinking is when we "think" we are an expert, or we have a life experience that impacts us. This perception of “expertise” or the impact of life experience can shape our decision-making process in a profound way. That’s because life experiences build the heuristics that we use as short-cuts to make System 1 decisions. Some of these heuristics are helpful, and some are not. If I were to ask you what is more probable: Dying in a train accident or getting struck by lightning?...Most people would say train accident. That’s because System 1 kicks in, pulls up memories of train accidents in the news and assumes that there is a higher probability of dying from a train accident than getting struck by lightning. This System 1 action is referred to as the availability or familiarity heuristic. But according to the National Center for Health Statistics, we have a higher chance of dying from a lightning strike than we do from a railway accident. According to that same study, Americans are two and a half times more likely to die from a bee sting than from a dog attack. Like bee stings, average market gains over long periods of time aren’t as headline grabbing as train crashes or market crashes, so they are not as prominent in our minds. Investors are quick to succumb to System 1 thinking when we avoid “riskier” asset classes, especially when we have the impact of the great recession burned into the back of our minds. By focusing all our attention on the potential for short-term fluctuations in performance, we ignore the fact that these “riskier” asset classes can be the ones that have the greatest long-term impact on portfolio growth. The familiarity heuristic may not only cause us to avoid high-performing asset classes, it can also work against us by biasing us toward things we are familiar with. According to JP Morgan, people living on the West Coast tend to overweight the technology sector, while people living in Texas tend to overweight energy; and people in the Midwest tend to overweight industrials. While it is wise to invest in asset classes where we have an edge, it is a statistical improbability that the entire universe of Texans has an edge in energy investments. And it’s equally improbable that the entire universe of Midwesterners has an edge in industrials. While System 1 might convince us all that we are “experts,” we can’t all have an edge. Not everyone is the “smartest person in the room.” The irony of the familiarity heuristic is that it can cause us to avoid “riskier” asset classes on one side and cause us to overweight our portfolio on the other side, ultimately creating more potential hazard from a lack of diversification and concentration risk. We are all swayed by our personal biases and deceptive thinking from time to time. The key to managing our thinking is to simply recognize that we are inclined to be biased. Rather than reacting to System 1 and our biases, we need to access System 2 and ask ourselves deeper questions. ​ System 1 thinking looks at the high performing mutual fund and says “this fund has significantly outperformed my other mutual funds in the last two years. Let’s sell my underperforming funds and buy more of this fund.” ​ System 2 thinking looks at the high performing mutual fund and asks: “Why is this fund outperforming? Did the manager tactically recognize the hot sectors? Or was it always invested in this sector, and this sector happened to outperform the last two years? How likely is it that this sector will continue to appreciate when it is extremely expensive today? Let’s sell half of this holding and move into something that has more potential to grow.” ​ System 1 thinking looks at a marginal company in a stagnant industry and says: “Wow this company has not grown earnings in the last three years, there is no way I would own this stock.” ​ System 2 thinking says: “This company has not grown earnings in the last three years, but the balance sheet is stronger today and the market cap is one-third of what it was three years ago. At the extremely depressed valuation, I’m willing to bet that this company will converge back to a more-normal valuation when investors begin to recognize the safer balance sheet.” ​ Boiling it Down: System 1 can do a pretty good job of keeping us alive in the jungle, but may not serve us as well when seeking to maximize our long-term wealth. That’s where we need to recognize that we are inclined to be biased and our short-cutting heuristics may be hurting us. Tapping into the benefits of System 2’s slow thinking can help prevent us from making costly mistakes. Read Part Three: ".The Fallacy of the Formula"

Frequently Asked Questions Monotelo Quarterly Tax Tips White Papers How To Avoid An Audit Do you have a PTN? EAs and CPAs What is your tax background? What records? Fees File electronically What if I get audited? Who will sign my return? When will I receive a copy of my return? How do I find you? Do you have a PTIN (preparer tax identification number)? What is your tax background? What records and other documentation will you need from me? How do you determine your fees? Can I file electronically? What happens if I get audited? Who will sign my return? When will I receive a copy of my return? How do I find you if I have a question or a problem after tax season is over? ​ Do you have a PTIN (preparer tax identification number)? ​ All of our tax preparers and client-facing staff who are involved in the return preparation process have their PTINS. Feel free to ask for the PTIN of any staff member involved in return preparation. ​ What is your tax background? ​ Most of our tax preparers are either CPA's or Enrolled Agents. A Certified Public Accountant (CPA) is certified by the state to act as a public accountant. A CPA is the only licensed qualification in accounting. To be certified, candidates are required to pass an exam. Most states also require an ethics exam or course as well as continuing education credits. A CPA may specialize in tax but not necessarily: there's a wide range of CPA services including accounting, auditing, financial planning, technology consulting and business valuation. ​ An Enrolled Agent (EA) has earned the privilege of representing taxpayers before the Internal Revenue Service by passing a three-part comprehensive IRS exam. The EA status is the highest credential the IRS awards. EA's must adhere to ethical standards and complete 72 hours of continuing education courses every three years. ​ What records and other documentation will you need from me? ​ We will need all your W-2's, 1099's, 1098's and other verification of income and expenses in order to prepare your return. We do not need individual receipts. Please do not send any individual receipts unless we request them. You must retain all your receipts in case of an audit by the IRS. ​ How do you determine your fees? ​ Our fees are completely transparent - you can view our fees on our Fee Schedule . ​ Can I file electronically? ​ Yes, after your return is completed, you will receive E-file consent forms (Form 8879) and be given the option to have us electronically file on your behalf after you review and approve the return. ​ What happens if I get audited? ​ As Enrolled Agents and Certified Public Accountants, we are authorized to represent our clients before the Internal Revenue Service. We can respond to questions and represent you in front of the IRS. ​ If there is an error on your return and it is our fault, we will fix the error, file an amended return on your behalf and you will not be charged for any amended return preparation fees. ​ Who will sign my return? ​ Your tax return will be signed by the person who performs the final review of your return. This person will have a PTIN and the PTIN will appear next to their signature. We can give you the name of the person who will be reviewing and signing your return at the time we receive your tax documents. When will I receive a copy of my return? ​ You will receive a complete copy of your return after we finish preparing the return and the tax preparation fees have been paid. You can choose to receive an electronic copy, a physical copy or both. You will need a copy of your return to review it prior to filing or having us E-file on your behalf. ​ How do I find you if I have a question or a problem after tax season is over? ​ Our offices are open twelve months a year. If you receive a request from the IRS or your state department of revenue, we are available to meet in person, or connect by phone or email. ​ Click Here to check out the IRS website for more resources in choosing a tax preparation firm ​

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Beware of Hedge Fund Managers Bearing Gifts Quarterly: Oct 17 "Do not trust the horse, Trojans. Whatever it is, I fear the Greeks even when they bring gifts." According to Greek mythology, the Greeks had struggled for nearly a decade to penetrate and conquer the city of Troy. In an act of trickery, they constructed a huge wooden horse, hid men inside it and pretended to sail away from the city. ​ Ignoring wise counsel, the Trojans opened the gates and unknowingly opened the door for the Greek army to enter their city. Shortly after the Trojans brought the horse into the formerly impenetrable area, the Greek army sailed back under the cover of night and stationed their men to attack. Once the Greek army was in place, the men crept out of the horse and opened the gates for the rest of the army to enter and destroy the city of Troy. ​ The term "Trojan Horse" has metaphorically come to mean any trick or strategy that causes a target to invite a foe into a securely protected area. We correlate this story to the appeal of hedge funds and private equity to a high net worth investor and the economic reality that is likely to follow. Diverging from our normal lines of discussion, we are going to explore the implications of the Tax Cuts and Jobs Act (the new tax code) on alternative investment income. ​ The tax implications on alternative investment income are staggering. The new US tax code raises the bar so high that most alternative investments will fail to pass the test for the average high-net-worth investor. ​ The term “high-net-worth investor” is a relative term. After all, nobody wants to be the one millionaire on an island of billionaires! Rather than defining high-net-worth by the size of someone’s balance sheet, we are going to define it as anyone with an annual income above $400,000, the beginning of the 35% tax bracket for married couples filing a joint tax return here in the United States ($200,000 is the beginning of the 35% bracket for a single filer). ​ For today’s discussion we are going to use the 37% tax bracket to define high net worth, so technically this would be a married couple with a taxable income above $600,000 or an individual with a taxable income above $300,000. A brief history lesson on our tax code and investment management fees: The “two and twenty” fee structure (2% management fee and 20% performance or carried interest fee) charged by hedge fund and private equity managers has always been a challenging hurdle for alternative investment managers to overcome. Prior to 2018, however, the US tax code took some of that sting out of the bite by allowing investors to deduct their investment management fees once they surpassed 2% of adjusted gross income. In other words, a tax payer with $1 million dollars in adjusted gross income could deduct the investment management fees that surpassed the $20,000 mark (the 2% hurdle). The new tax code however, has removed investment management fees from the list of itemizable deductions. The colossal impact of this change comes down to the fact that 100% of your investment income flows through to your personal tax return and your investment management fees no longer offset that income. It’s like the opposite of a tax-free municipal bond. Instead of receiving income on which the government will not tax you, you are required to pay tax on income you will never receive. Let’s take the example of a married couple making $700,000 per year from their employer plus another $150,000 of income from their alternative investments. To keep things simple, we will make the following assumptions: ​ The couple earns $700,000 in wage income from their employer The alternative investment is custodied in a traditional taxable account (ie. non-retirement account) The alternative investment generates $150,000 of investment income on $1,000,000 of invested capital Half of the investment income is taxed at the investor's ordinary income tax rate and half is taxed at the long-term capital gains rate The investment manager is paid $20,000 from the 2% management fee and $26,000 from the 20% performance fee ​ Description $150,000 Of Investment Income ($20,000) 2% Management Fee ($26,000) 20% Performance fee $104,000 Net to Investor Before Tax Tax Liability +$42,750 (Federal Income Tax) +$3,885 (Net Investment Income Tax) Cannot be deducted on Schedule A Cannot be deducted on Schedule A $46,635 Additional Tax Liability The investor receives $57,365 after investment management fees and federal income tax, and still has a state income tax bill to pay. This 5.7% return is a long way from the 15% gross return generated by the hedge fund manager. Keep in mind, we are just looking at the tax implications of alternative investment fee structures. Considering the fact that the HFRI Equity Hedge Index only returned 3.38% over the last five years (according to Hedge Fund Research, Inc. – 2/28/19), we haven’t even begun to address the impact of performance fees on net returns to investors. Potential Solution: Asset Location One potential way to address this problem is to put investments with high management fees into tax-deferred retirement accounts instead of traditional taxable accounts. The challenge with this option is that it puts the investor at risk of being subject to UBIT issues (unrelated business income tax). Because of the potential UBIT and ERISA issues, some managers and many custodians will not accept retirement assets in alternative funds. This asset location issue is a critical piece of the wealth preservation and accumulation puzzle. Unfortunately, this mission-critical issue is often missed by the wealth management community due to a lack of knowledge about our tax code. Conclusion The Tax Cuts and Jobs Act creates a very challenging hurdle for many alternative investments to overcome. Investors should be careful to analyze the net after-tax return on their investments and make sure they are being fairly compensated for putting their capital at risk.

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THE AMERICAN RESCUE PLAN ACT We apologize in advance for the tax speak in this update. Sometimes it’s hard to remove the tax language and maintain accuracy. Please stay with us for the next three minutes and reach out if there are any points that need additional clarity. This is part one of a series we are writing to keep you informed on the American Rescue Plan Act of 2021 (ARPA), the legislation that President Biden signed into law on March 11, 2021. While we are planning to provide more insight over the next few months on how this legislation impacts you, in today’s article we will attempt to summarize the most important components of the new legislation. The Quick Summary: The American Rescue Plan Act of 2021 (ARPA) is an extensive relief bill that includes changes to income and payroll taxes, expansion of unemployment benefits, and another round of stimulus payments. Like the two relief bills that preceded it, this new law is extensive, with significant implications on businesses and tax payers. Partial Exclusion of 2020 Unemployment Compensation – The ARPA provides an exclusion from income on the first $10,200 of unemployment compensation received per taxpayer if the taxpayer’s adjusted gross income (“AGI” – remember this term for today’s update!) is less than $150,000. Once AGI reaches $150,000, all unemployment compensation will be taxable. This cutoff at AGI of $150,000 applies to all taxpayers, regardless of filing status. Recovery Rebates and Stimulus Payments - One of the most important provisions of the ARPA relates to additional stimulus payments that will be sent to individuals. These payments are $1,400 ($2,800 for joint filers) plus $1,400 for each dependent on the taxpayer’s return. Unlike the prior stimulus payments, all dependents claimed on a return will be included, regardless of age. Just like the prior recovery rebate checks, there is a phase-out range based on AGI. The AGI phase-out ranges are: ​ Joint filers: $150,000 to $160,000 Head-of-household filers: $112,500 to $120,000 All other filers (single, married-filing-separately): $75,000 to $80,000 ​ Checks will be issued based on the latest tax return that has been filed and processed. This rebate check will be reconciled on your 2021 individual income tax return in the form of a credit . In other words, if you do not receive the third stimulus check and you qualify to receive it, you will receive it through your 2021 tax return. Individual Changes - Some of the more significant tax law changes from the ARPA relate to the child tax credit. For 2021 the credit has been increased to $3,000 per child ($3,600 for a child under the age of six) and is now fully refundable. The new law also increased the age of qualifying children from 16 to 17. As with many other provisions, there is a phase-out based on AGI in excess of threshold amounts. It is important to note that half of this credit will be paid out in the form of an advance starting on July 15, 2021 and will be made monthly through the second half of the year. If the advanced payments you receive exceed the amount you qualify for on your 2021 tax return you will need to repay any excess amount. We will have more details on this later in the year once the IRS puts the system in place to handle these advanced payments. Other provisions in ARPA that also impact individual filers include: ​ Expanded Child Dependent Care Credit – For 2021 only, the credit was made fully refundable and it was increased to 50% of qualified expenses. The credit will be reduced gradually down to 20% of qualified expenses as your AGI exceeds $125,000 and gradually phased out completely after your AGI reaches $400,000. The amount of eligible expenses qualifying for the credit have been increased to $8,000 for one individual and $16,000 for two or more individuals. Premium Tax Credit – The change in ARPA applies to 2021 and 2022 for the premium tax credit for health insurance. The credit is now available to individuals with higher incomes and increases the credit amount for those already qualified. For 2021 only, advance premium tax credits will be available for individuals receiving unemployment compensation. ​ If you have any questions about how these changes will impact you please reach out to us. Failing to order your affairs to minimize your tax burden could cost you significant money - so don't wait to take action. If you have additional questions or need some planning help, please reach out to us.