Owning a small business –lessons learned

At Goldstein Law Group, S.C., we serve as outside counsel to business. Accordingly, it is sometimes easy to forget that we, ourselves, are also in business. In February of this year, we celebrated our 15-year anniversary (and nearly 30 years of law practice for me). It’s been quite a ride.

Mark Goldstein Owner/Attorney Goldstein Law Group

We have been afforded the unique opportunity to learn, not just from our own experiences, but from our clients as well.

Here are a few such lessons (paired with a few favorite quotes):

Shep lived by three rules: 1) Get the money, 2) Remember to get the money, and 3) Always remember to get the money.

– Supermensch (The Legend of Shep Gordon)

The rules of business may be simple, but execution can be far more difficult. Create systems, and follow them, but recognize that your systems are just a start. They will need to be revisited and tweaked and, at times, violated or even discarded. Knowing when and how to do this is the key. For example, foregoing your own paycheck – less than optimal, but it happens (no matter what they say about “always pay yourself first”). On the other hand, foregoing payroll taxes or payments to your bank or health insurer is inviting trouble.

– Office Space

If employees are not your solution, they may very well become your problem. Long before recent events, demographic forecasts suggested staffing would become a great challenge. In years since, we had the pandemic, the push for remote work, and now “quiet quitting.” How do you feel about the compensation and benefit package you are currently offering? Can you demonstrate that it has helped you attract and retain (the right) employees?

There's two types of motorcyclists; those who have crashed, and those who have not yet crashed.

You will undoubtedly hear from other business owners who have flaunted the rules (or simply been ignorant of them). Examples include taxation, minority business owner rules, exempt/non-exempt determinations, and all the regulations relative to independent contractor status. Some of them will suffer the consequences, and others may never. As for yourself, know what you don’t know and keep your own counsel. Having trusted attorneys, accountants, mentors, and other advisors will help you keep your bearings.

In the end, Teddy Roosevelt captured it well when he talked of his admiration for the “man who is actually in the arena, whose face is marred by dust and sweat and blood, who strives valiantly, who errs and comes up short again and again, because there is no effort without error or shortcoming, but who knows the great enthusiasms, the great devotions, who spends himself for a worthy cause…” And yet there is nothing noble about stumbling into the same traps as generations of prior business owners or those easily avoided.

Thanks to the MMAC for the community of business owners it has created and serves, and for providing me this opportunity to reflect on all that I’ve learned over the past years. Onward!