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Side Gigs Beyond the Cockpit

Apart from the career earning potential, the glamour factor of the position and the opportunities for travel, one of the most rewarding aspects of the job of a professional pilot is the schedule. Even at the more junior levels, most pilots spend less time actually working – flying the plane – than do their 9-5 non-flying counterparts in other industries. Add a few years of seniority into the mix, and the amount of time pilots have available to either pick up more flying, spend quality time with family, or engage in another career adventure is significant.

There’s a true story about a career-aspiring pilot who, after earning his hours as a flight instructor, got his then-dream job flying for a corporate flight department. It was a career he enjoyed and it afforded him a rewarding lifestyle. Years into his career, like many other pilots, he found out that his professional aviation schedule afforded him much free time; he had enough time on his hands to start dabbling in another career interests. In his particular case, besides being a pilot, his other dream job was to be an NFL referee. He pursued that dream and was successful in landing the unique opportunity. Before long, his second “hobby” dream career became his primary career and he left flying.

That story is not presented as a tale encouraging everyone to follow other dreams and leave the industry but to illustrate that, as a professional pilot, your schedule and unique set of analytical skills/leadership qualities give you options. Over the last several years, there have been many career changers coming over to aviation. Many of them – originally aviation bound – ended up diverting their career during a time when the industry wasn’t strong. In some cases, they came back while, in others, their “backup” career ended up being more lucrative and rewarding. Aviation became the hobby on accident.

We find ourselves at another point in aviation history when the industry might not be as rewarding to as many, and there are many pilots looking for a “side gig” or backup career. Even in good times, it is not uncommon for pilots to make use of their significant downtown to more-than-dabble in a side business.

FranNet, a franchise consulting company with over 30 years in business, states that pilots have always been good candidates for buying both startup and existing businesses or franchises. “Franchising provides a road map,” explains CEO Jania Bailey. “It provides the back-office support that we’re used to so you’re not flying without instruments.” In her opinion, pilots are a well-educated group and have a very unique schedule, allowing aspiring entrepreneurs to take to the skies of other career ventures, even while maintaining their flying jobs. And being in business for one’s self is an attractive option for many. FranNet reports that they have definitely seen a surge of pilots in the last few months, due to some of the uncertainty of the industry. Even after the industry rebounds, so many of the opportunities available can be run as a semi-absentee owner and by the time things pick up, you’ll have a well-oiled machine. “Be sure you’re working with people that are credible,” Ms. Bailey warns when it comes to franchising.

Franchises and other people’s businesses are, of course, but one option, as Adam LoSasso and his father discovered – both flying with a major airline – when a too-good-to-be-true opportunity in yacht sales presented itself. Having hit what he felt was the pinnacle of his career, Captain LoSasso wanted more than just a Captain’s position and seniority number. He took a two-year leave from his airline and the father and son duo purchased a yacht brokerage company. When asked about the commitment to pursue and grow his new business, Adam reported, “It is time consuming. If I was working full-time at an airline, it might not be possible.” He also commented that the initial cost of getting into the business was more than expected and to have some emergency money stashed away. By the time his leave is up, Adam and his father will have the business relatively self-sufficient. With other employees on hand to see to the day-to-day tasks of running the business, the two of them can go back to doing something they love in flying the line for their respective companies.

For those pilots wanting the spread their wings but stay closer to home. Aquiline Drones, an Unmanned Aerial Vehicle training and business development company, was founded by professional pilot Barry Alexander. Not only do they provide participants with the knowledge and training required to work in the UAS industry, their company gives graduates an LLC with which to conduct their own drone business, insurance, and finance options for acquiring a commercial grade UAV. But according to Vice President Roger Nunamann, perhaps most importantly is their Drone on Demand proprietary software program which provides “an entire ecosystem, a tool of employment” to help pilots market themselves and identify work in their immediate surrounding area. With the ability to set one’s own schedule and work as much as they want, Aquiline Drones can enable pilots to earn a six-figure income which they can pursue as both an alternative or supplement to a normal “flying the line” position.

Everyone comes from different backgrounds and has likely learned – maybe even mastered – many skills on their way to professional pilothood. For some, starting or running a business might be an area in which they are already well-versed; but for many, this may be a whole new world. And just like getting some additional training before flying a new aircraft or into a new area, make sure you educate yourself on all aspects of this business venture. For example, apart from the division of focus while still trying to maintain one’s primary career, there are some financial aspects of dabbling in a side career that all pilots need to keep in mind.

- Minimize personal guarantees. Many small business owners don’t think too much about using personal credit cards or signing a vendor note for business expenses but, keep in mind, you’re signing a personal guarantee. If your business doesn’t make it, you are personally responsible and creditors can – and will – come after you!

- Make sure you understand – or go get an understanding – of accounting. Hours, weeks and months could be spent on accounting. One of the biggest mistakes made is when it comes to double entry accounting. Too many small business start ups try to keep their books by inventing a convoluted excel spread sheet system. That doesn't work. Using a GAAP (Generally Accepted Accounting Principles) compliant double entry accounting system will ensure that balance sheets actually do balance. Having a good bookkeeper that understands these concepts will be a savior here, as will having a good CPA.

- If you plan on having employees, know the difference between W2 and 1099. One requires a lot more work on your part but garnishes more company loyalty and longevity. The other is less work intensive, but you give up a large amount of control of that employee. You also have to keep in mind that, depending on the business, workman’s comp insurance may or may not be something that is necessary, and 1099 independent contractor workers do not get this.

- Tax compliance; there’s more than just income tax! There’s payroll taxes (for W2 employees only), social security tax, FICA taxes, country and/or state taxes, taxes on revenue, property and assets … the list goes on.

Even with proper due diligence and the greatest of intentions, the stress of having a second business often wins out in the end. “Entrepreneurs by nature are optimistic,” cautions Tom Smith, CFP and Vice President of FAPA Financial Services. “But failure rates are high. Roughly half of startups will last 5 years. The reasons are varied (bad market research to establish a need, poor management, not enough working capital, bad business model, poor marketing, ignoring customers...) but all result in financial failure. Understanding financial risks require knowledge and discipline in accounting, taxes, legal structure of the business, type of employees and benefits, sources and uses of capital, and others. Starting and operating a small business is not for the faint of heart.”

A career in flying is not for the faint of heart either; less than 20% of everyone that starts a venture into aviation ever finishes, so pilots are already a cut above the rest. Still, while a side business venture can be exciting, it is a very involved process. “Lead with education”, advises Jania Bailey. “Be willing to know what you don’t know.” It’s those small aspects of ignorance that will end up being the biggest thorns in your side. It’s the unexpected that will haunt you. You have to know exactly what you’re getting into, so do your research and seek the counsel of others. Treat your side business planning just like you would treat an IFR flight plan across the country; ecome available with all information concerning your proposed business adventure and you’ll be stacking the deck as much in your favor as possible.