Entrepreneurial Maturity

I wish I could take credit for the term “entrepreneurial maturity” but I can’t. Credit goes to Jason Jones, a licensed public accountant who offers CFO services to businesses. In writing about his challenges in working with businesses, Jason says:

(T)he challenge I immediately discovered was in finding small business clients who had the entrepreneurial maturity to realize what they needed to know financially in order for their business to thrive and survive, and who had a strong awareness of their own conscious incompetence accordingly.

All too often, I got referrals from professionals and inquiries from prospective clients, only to engage in power struggles with the client in formulating business/financial strategies, which were often rooted in a combination of unconscious incompetence (they don’t know that they don’t know) and “Founder’s Syndrome” (since they’re the founder/owner, they know everything about the company they need to – they often hire “yes men” to help reinforce their flawed way of thinking). But I digress.

In other words, a business owner who has entrepreneurial maturity knows what they don’t know.

The challenges Jason writes about in his blog post are the same challenges I have faced in working with some small businesses. Here’s an example of a real conversation that took place with a business owner who’s business was always struggling with cash flow in its first couple of years of existence. The owner had been complaining that his advisers weren’t asking the right questions, so I was trying to be proactive:

Me: “Let’s look at where the money is coming from and where it’s going and start setting up strategies.”

Business owner: “Well, a growing business consumes resources. No business in its first few years has a big profit margin. That’s just the way it is.”

Period. Conversation over.

No review of finances was done.

ID-100260221This owner would go on to periodically complain about how hard it was to run a business, and how no one was helping him.

That’s an example of an owner who hasn’t matured enough to realize that he was talking to a knowledgeable professional who was trying to help him. Instead, the owner made a declaration that indicated he knew all about it and nothing further needed said. Yet, this same business owner still complains that the professionals around him aren’t giving good advice.

This scenario happens far more than it should.

As a professional, it’s hard to deal with.

I like working with startups, especially the people who started like me — on the side, from scratch — and have grown. But logically, these are the folks who have the least entrepreneurial maturity.

Sometimes I catch myself lacking in entrepreneurial maturity too.

I’m not sure what the solution is.

Time. Experience. A realistic view of the struggles of running a business.

And an acknowledgment that as business owners, there are things we won’t know.

Image courtesy of Stuart Miles / freedigitalphotos.net

IRS Says Online Sorority Is Not Tax Exempt

computer-room-415141_1280Tax law says certain clubs and social groups are exempt from income tax. This can include college sororities. But according to the IRS, this doesn’t apply to sororities created by online schools where the sorority members never meet face-to-face.


A national, for-profit college (the IRS ruling didn’t say which one) started an online sorority. Reading through IRS Letter Ruling 201434022, it appears that this sorority operates similar to other sororities, except almost all activities take place online.

Section 501(c)(7) of the Internal Revenue Code says organizations organized as a club for organized for recreation is exempt from paying income tax. This would seem to apply to a sorority, but the IRS relied on a series of old revenue rulings from the 1950s thru the 1970s, and a court case from 1965, in ruling that an online sorority doesn’t qualify for tax-exempt status.

What is “Social”?

The IRS ruled that because the group didn’t have face-to-face meetings, it didn’t qualify. From the ruling:

Commingling and the promotion of fellowship are not a material part of your operations. Commingling is a necessary and material part in the life of an organization exempt under Sec. 501(c)(7) and is deemed present if such things as meetings, gatherings, and regular facilities are evident…. Face-to-face interaction is important for members of a social club. Organizations that do not afford opportunities for this personal contact among members are not entitled to exemption under Sec. 501(c)(7), even though they may be organized not for profit with no part of their earnings inuring to the benefit of shareholders.

In reading through the rest of the ruling, it appears to me that the IRS may be open to saying an online group could qualify for not-for profit status if there are recreational aspects to the group and/or if the group forms local chapters that engage in periodic group events and activities:

While you engage in some face-to-face interaction at your conferences held once a year, the majority of your activities are performed in an individual capacity and over the Internet rather than face-to-face. Additionally, the topics discussed at your face-to-face meeting and over the Internet pertain more to your organizational aspects rather than the promotion of any recreational or other nonprofitable purposes. Further, you do not expend money on social or recreational purposes.


It looks like the group has the right to appeal this ruling. If I were them, I would immediately update bylaws and create local chapters that have periodic meetings and social outings and see if that would help get the not-for-profit status approved.

Image courtesy of user “Stux” on Pixabay.com


Putting Profit First While Planning for Expenses

In July, Michael Michalowicz, who writes books about entrepreneurship (which I have heard are very good; “The Pumpkin Plan” is fall-163496_1280on my to-read list) wrote a blog post titled “Take Your Profit First, Always.”

The gist of the post is, instead of looking at profitability as “Income minus Expenses = Profit” you should flip the formula. “Income minus Profit = Expenses.”

Pay yourself first, then spend money on expenses. As the author says:

In practice, as deposits from sales come in a predetermined percentage, for example 15%, is immediately transferred to a separate profit account. The remainder is available for the business leader to run business as usual. The business owner will see his available cash (which has had the profit already deducted) and make decisions accordingly. The new equipment purchase may be delayed, or a more cost effective alternative may be found. A new hire won’t be made because the money is not there, and perhaps the entrepreneur will conclude was unnecessary in the first place.

As Mr. Michalowicz correctly points out, most of us who own businesses make decisions based on how much cash is in the bank today. By flipping the profitability formula, it forces the business owner to pay themselves first (or at the very least, to leave a reserve in the bank).


This is a great way to look at things. In fact, when I shared this article on Twitter, I stated that it was brilliant advice. But there are some cautions.

ONE: New businesses typically have legitimate expenses that are true business needs. You might have to accept a lower profit margin at first in order to get your business going. Note the key phrase is “true business needs.”

TWO: The real point of all this is: business owners need to put thought into major expenses. This means looking at the numbers and determining if you can really afford to hire an employee, or buy equipment, or upgrade software. Maybe it’s worth it to spend the money. Maybe it can wait. And maybe it’s not worth it at all.

Image courtesy of PublicDomainPictures on Pixabay

When Does the “1099s to Veterinarians” Rule Start?

My blog post in January about issuing 1099s to incorporated veterinarians has become one of the most popular posts I’ve ever www.irs.gov pub irs-pdf f1099msc-page-001written. It’s generated phone calls, e-mails and questions. The most-common question is: when do we need to start issuing 1099s to incorporated veterinarians? When does this rule start?

The answer is: there’s not a “start date” to this rule. The IRS’s guidance was in a letter ruling that simply said “yes, 1099s should be issued to incorporated veterinarians.”

In other words, the IRS says it’s how things have always been.

Which brings up a question of: what about prior years? I suppose the IRS would say the technical answer is to file the 1099s late. That seems like crazy talk to me. I would lean towards starting to issue the 1099s from the time of the IRS ruling (December 2013) and forward.

S-Corporation Compensation Revisted

In May I wrote about a friend of mine who owns an S-corporation and who received bad advice from his CPA regarding the salary rules for S-corps.

My friend’s corporation took in about $25,000 of gross income and netted about $10,000 after expenses. He drew out nearly all of that $10,000 profit for himself.

Despite what his CPA said, the IRS’s position and case law are quite clear that since he drew money out of the corporation and he provided services to the corporation he needs to pay himself a salary.

But what should the salary be? And what if the year has ended and the W-2 deadlines have passed, but the corporate tax return still needs filed?

Here are some options:

ONE: Find legitimate expenses the owner incurred, and call the draws expense reimbursements.

My friend could legitimately document his cell phone usage for business (paid out of personal funds) as well as mileage.  As long as there’s a written reimbursement policy in place, (which — shockingly — my friend DID have), he could legitimately argue that some or all of his draws were reimbursements rather than salary.

Another thing he had going for him: in his articles of incorporation, a resolution was created that specifically said that he would pay the startup costs out of his own funds and the corporation would reimburse him.

In his case, between the startup costs and other reimbursements, he was probably close to the $10,000 mark and could reasonably say his salary that first year was $0.

TWO: File the payroll forms late.

What if there were no reimbursements (or no documentation in place to justify reimbursements)? You could classify some or all of the draws as salary and file the payroll forms late and pay whatever penalties might be assessed. While this is the least desirable, it’s probably the most “right and proper” fix.

THREE: The 1099 route.

One thing I’ve done before – and it’s admittedly not “right and proper” – is to have the owner issue himself a 1099 for some or all of his draws for the year in question, and then get real payroll set up for the current year and going forward. Doing this results in the FICA taxes being paid on the owner’s personal return (in the form of self-employment tax) rather than on the corporate side. Again, not right and proper, but it’s a quick and dirty fix in a pinch.