May 19, 2020

The Psychology of Taxes on Entrepreneurs

CPA services
business taxes
entrepreneur tax
Bizclik Editor
7 min
The Psychology of Taxes on Entrepreneurs


by Greg Crabtree

As an accountant, I have a unique vantage point to observe how entrepreneurs change their decisions based on tax policy.  My focus as a business advisor is making businesses more profitable first, then dealing with the tax implications of profit.

As much as I would like to focus on profit, I regularly have to “reprogram” the entrepreneur’s thinking on taxes.  With new clients, I often have to overcome the advice given by their former CPA, who would inevitably advise them to buy more equipment at the end of each year to avoid paying taxes.  Folks, this is just plain dumb unless your goal is to never build wealth from your business.

I would classify entrepreneurs into three groups when it comes to taxes:

  1. No Taxes, No Way Nate – This guy will do anything possible, including cheating, to pay no taxes.  From our experience with clients we turn down or terminate, this problem is likely bigger than even the IRS estimates.
  2. Accidentally Profitable Alex – This guy is so focused and passionate about his business, that he forgets to plan for success, and the resulting taxes often come as a surprise. Many times this is from a cash out event rather than ongoing profit.
  3. Eddie the Enduring Entrepreneur – This is my favorite type of entrepreneur to work with because he is building a lasting business that will be a tremendous wealth-generating engine for himself and his family.  This entrepreneur is often held back by bad advisors who encourage him to waste wealth to avoid taxes, but his instinct and common sense frequently help him overcome the faulty counsel.

The only type of tax that you can make No Taxes Nate pay would be a sales tax (or VAT – value added tax).  But given Nate’s predisposition to not pay any taxes, he will find a way to skim or avoid the tax all together.  Unfortunately for us honest entrepreneurs, we will endure audits because of Nate, since that is the only way the tax collector can find him.

Accidentally Profitable Alex does not make decisions based on taxes until his first major tax event occurs.  Once that event happens, he may change his name to Nate if he perceives the tax impact is too great.  Alex is likely to be a “one’er,” which is the term used for someone who can be profitable once, but cannot repeat the success.

Eddie is the guy we should focus tax policy around because he is the guy that employs the bulk of the workers in the U.S. economy.  Employment studies have shown that 70% of all employees are employed by privately held businesses and 100% of all new job growth comes from private business.  Publicly held businesses kill as many jobs as they create and that is just the nature of the beast.  Every time a publicly held business has purchased one of my clients, the public business has decreased employment of the company purchased, not increased.  They are inherently geared toward buying the “business” done by the private company, bolting it on to their infrastructure, and off-loading the private company’s management.

Since I started in public accounting in 1978, I have seen multiple tax ideas played out and the varying business decisions resulting from each policy.  I can honestly say that no policy proposed has ever caused the result the policy maker wanted, with the possible exception of the 1986 Tax Reform Act.  This is the tax act that eliminated tax shelters and lowered tax rates to 2 simple brackets, 15% and 28%.  This was the first time I saw my clients get focused on making profits and just pay the taxes.  Unfortunately, the 2 brackets eventually turned back into 6 brackets that topped out at 39.6%.  In addition to Federal taxes, states have continued to raise rates as well, and the average income tax rate runs around 6%.

What is the Optimum Rate?

I can honestly tell you that somewhere between 25% and 30% (federal and state tax combined) is the point where entrepreneurs will push forward to make more money rather than just put it on pause and take care of their own.  It also helps to have fewer brackets and get to the top bracket relatively quickly.  Simplicity has a tremendous power to move people to action and release them from the paralysis that lack of understanding brings.

Policy makers need to understand that entrepreneurs can always trim growth and just take care of themselves and their core employees when uncertainty abounds.  When they are presented with a flat economy like the one we face now, they need long-term certainty to encourage them to take some risks.  When they think their hard work will be eaten up in taxes, it takes all the incentive away.

Disconnect between Cash Flow and Taxes:

In my interaction with entrepreneurs from around the world through the Entrepreneurs’ Organization, it struck me that U.S. entrepreneurs are significantly under-capitalized compared to their counterparts in Europe and Asia.  Easy credit played a big part in this, but tax policy also plays a huge role.  The typical U.S. entrepreneur rubs two dollars bills together and tries to make a profit.  They start without capital, with just and idea and a dream, and find a way to make it work.

The disconnect that policy makers do not understand is that during the capital building phase of the business (typically the first 5 years in business) all of the after-tax profits are plowed back into the business.  Politicians make comments about taxing the rich people, but the ones I deal with that have a business that shows $300,000 in profit are having to pay an average of $120,000 in taxes (40% federal and state) which only leaves $180,000 to put back into the business to repay debt (remember, you encouraged them to start a business and borrow to start it).

Until you have sat in the conference room going over the final year end numbers with a business owner, you have no concept of the disappointment they feel to learn that what appeared to be a success of $300,000 in profit is really only $180,000 (which they used to repay debt so their cash balance did not change).  And if they are diligent and have no bumps in the market, they will be out of debt in 5 years.   Those are big “ifs”.  We found that we have to monitor this quarterly with clients because they spend their profits and leave no cash for taxes.  When they have no cash for taxes, this starts the death spiral of their business because the IRS is now a creditor of last resort.

The Case for Simplification:

Taxes may never be simple, but folks, we can do better than this.  Also, I would be a happy practitioner if I never had to help someone file another tax return.  We do not need tax preparation to be a jobs program, all of those folks can easily be used to do other useful and more productive things.

Here are my ideas from the real world:

  1. Go back to 2 simple brackets, 15% and 25%  - You need to keep the top bracket at 25% since we need room for inevitable increases in Social Security and Medicare tax rates or limits.  All income would be treated the same (i.e. no capital gains).
  2. Simplify taxation of C corporations by allowing a tax deduction for dividends paid.  This will encourage public companies to pay out excess capital back into the marketplace, plus you can withhold taxes on the payment and increase tax cash flows to the Treasury.  This would also help small privately held C corporations eliminate double taxation and put them on a level playing field with S corporations and LLC’s.
  3. Withhold taxes on flow of funds – since the tax brackets are lower, it is more reasonable to withhold taxes on payments made to owners.  Any money taken out by an owner of an S corporation, C Corporation or LLC would have taxes withheld on the payment (no shareholder loans!).  This would encourage owners to not fall into bad habits of taking money out of the business without considering tax implications until it is too late.
  4. Eliminate itemized deductions – it is time for us to realize we only pollute the thinking of the taxpayer when we make something deductible.  You can adjust personal exemptions and a standard deduction to some reasonable level to protect the lower income levels, but after that, make it simple and non-tax motivated.

Greg Crabtree has worked in the financial industry for more than thirty years and founded Crabtree, Rowe & Berger, PC, a CPA firm dedicated to helping entrepreneurs build the economic engine of their business. In addition to serving as the firm’s CEO, Crabtree leads the business consulting team—helping clients align their financial goals with their profit model and their core business values. He is the author of Simple Numbers, Straight Talk, Big Profits! For more information, please visit:  

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Jun 8, 2021

Six issues at the top of tax and finance leaders’ agenda

Kate Birch
4 min
As businesses accelerate their transformation journeys, tax leaders are under increasing pressure to add strategic value. Deloitte reveals six tax trends

New Deloitte research reveals that tax leaders are under increasing pressure to add strategic value as companies accelerate business model transformation, from undergoing digital transformations to rethinking their supply chains or investing in green initiatives.

According to Phil Mills, Deloitte Global Tax & Legal Leader, to “truly deliver value to the business, the tax function needs to rethink its resourcing model and transform its technology infrastructure to create capacity and control costs”.

And the good news, according to Mills, is that tax and business leaders have more options at their disposal to achieve this.

Reflecting the insights of global tax and finance executives at global companies, Deloitte’s Tax Operations in Focus study reveals the six issues at the top of tax and finance leaders’ agenda.

Trend 1: Businesses seek more strategic counsel from tax

Companies are being pushed to develop new digital products and distribution channels and accelerate sustainable transformation and this is taking them into uncharted tax territory. Tax leaders say their teams must have the resources and skills to give deeper advisory support on digital business models (65%), supply chain restructuring (49%) and sustainability (48%) over the next two years. This means redrawing the boundaries of what tax professionals focus on, and accelerating adoption of advanced technologies and lower-cost resourcing models to meet compliance requirements and free up time.

According to Joanne Walker, Group Tax Director, BT Group PLC, "There’s still a heavy compliance load today, but the vision for the future would be that much of that falls away, and tax people become subject matter experts who help program the machine, ensure quality control, and redirect their time to advisory activity.”

Trend 2: Tipping point for resourcing models

Business partnering demands in the tax department are on the rise, but 93% of tax leaders say their department’s budget is remaining flat or falling. To ensure that the tax function can redefine itself as a strategic function at the pace that is required, leaders are choosing to move increasing amounts of compliance and reporting to a combination of shared service centers, finance departments, and outsourcing providers that have invested in best-in-class technology.

Trend 3: Digital tax administration is moving faster than expected

in addition to the rising focus of the corporate tax department partnering with their business counterparts, transformative changes to the way companies share tax information with revenue authorities is also creating an imperative to modernize operations at a faster pace. Nine in 10 (92%) respondents say that shifting revenue authority demands on digital tax administration will have a moderate or high impact on tax operations and resources over the next five years—and several heads of tax said the trend is moving faster than expected.

"It’s really stepped up in the last couple of years," says Anna Elphick, VP Tax, Unilever. "Tax authorities don't just want a faster turnaround for compliance but access into a company’s systems. It's not unreasonable to think that in a much shorter time than we expect, compliance will be about companies reviewing a return that's been drafted by the tax authorities."

Trend 4: Data simplification and lower-cost resourcing are top priorities

Tax leaders said that simplifying data management (53%) and moving to lower-cost resourcing models (51%) must be prioritized if tax is to become more proactive at delivering strategic insights to the business. Many tax teams are ensuring that they have a seat at the table as ERP systems are overhauled, which is paying dividends: 56% of those that have introduced NextGen ERP systems are now highly effective at supporting the business with scenario-modeling insights. Only 35% of those with moderate to low use of NextGen ERP systems said the same.

At Stryker, “we automated the source P&L process for transfer pricing which took a huge burden off of the divisions," says David Furgason, Vice President Tax. "Then we created a transfer price database to deposit and retrieve data so we have limited impact on the divisions. We are moving to a single ERP platform which will help us make take the next step with robotics.”

Trend 5: Skillsets are shifting

Embedding a new data infrastructure and redesigning processes are critical for the future tax vision. Tax leaders are aligned — data skills (45%) and technology process experience (43%) are ‘must have’ skills in a tax department of the future, but more traditional tax specialist knowledge also remains key (40%). The trick to success will be in tax leaders facilitating the way these professionals, with their different backgrounds, can work together collectively to unlock lasting value.

Take Infineon Technologies, which formed a VAT technology and governance group "that has the right knowledge about how to change the system to ensure it generates the right reports", according to Matthias Schubert, Global Head of Tax. "Involving them early was key as we took a greenfield approach, so we could think about what the optimal processes would look like and how more intelligent systems could make an impact 

Trend 6: 2020 brought productivity improvements

Improved productivity (50%) and accelerating shifts to remote working (48%) were cited as the biggest operational benefits to emerge from COVID-19-driven disruption. But, as 78% of leaders now plan to embed either hybrid or fully remote models in the tax function long term, 34% say maintaining productivity benefits is a top concern. And, as leaders think about building their talent pipeline and strengthening advisory skill sets, 47% say they must prioritize new approaches to talent recognition and career development over the next two years, while 36% say new processes for involving tax in business strategy decisions must be established.

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