Side-Hustles, Parallel Entrepreneurship and Multipreneurship

Having a "side hustle," as either a money maker or as a social impact hobby, is healthy for personal growth. It exposes you to solving problems different from those of your "day-job" and opens your mind to a different set of mentors, coaches, collaborators, and partners. Sometimes you'll be engaged in a different industry altogether, enabling you to grow your knowledge, experience, and skills.

Another manifestation of the side hustle is "Parallel Entrepreneurship." This two-track model allows you to innovate, adding products and services, pivoting to adjust to shifting demands and market conditions, either under your main business or under a new cap-table. (Just make sure that if your parallel entrepreneurship is in the same industry category as your primary job, you aren't in violation of any clauses of your employment contract).

Should you become a Parallel Entrepreneur? Depending on how you define it, perhaps you already are. The last ten years have seen an explosion in the "side hustle" and many entrepreneurs have a hobby that qualifies as a business. Mine happens to be a nonprofit, Giving Forward, with cause marketing as the mission. If my vision manifests itself, we'll be generating millions for other nonprofits within a couple of years. I've done it before and I'm stubborn (LOL: my earlier invention, We-Care, was a platform that "inspired" Amazon SMILE after generating $8.3 Million for nonprofits. Amazon Smile is currently at over $350 million). I'm also active in helping my wife's business grow and thrive, so that counts as a side hustle as well.

Does Parallel Entrepreneurship Actually Work?

The press, VCs and the business community are fascinated with serial entrepreneurs, e.g. Richard Branson, Elon Musk, Pierre Omidyar, and others. They talk much less about entrepreneurs who’ve successfully run their businesses in parallel. Jack Dorsey recently stepped down as CEO of Twitter (he’s also the CEO and co-founder of financial services startup Square, which in December changed its name to Block). Both companies are successful by any ordinary metric. However, tech companies are held to a higher standard. Publicly held tech and digital media companies are judged by the "comps" of their most successful peers.

Some might argue, based on Jack Dorsey's decision to focus on one company exclusively, that parallel entrepreneurship doesn't work. Clearly, Jack did an amazing job getting both companies to where they are today, and he did it on parallel tracks. Therefore, I would argue that parallel entrepreneurship works, and we see more evidence of it every day. (That doesn't mean that investors and analysts necessarily see the vision behind the entrepreneur's change in focus (or correctly perceive his or her consistent focus on innovation)).

It's easier when the CEO of a company has a new product idea that fits firmly under the brand and mission of the existing company. Then it's a new product or a brand extension. When a founder's new idea doesn't fit under the mission or brand of the current company, that's when a new startup is most likely. Another reason to structure the new startup business as an independent entity is valuation. The "comps" and valuation methodology of each industry and product line are quite different. Therefore, sometimes a separate cap-table is optimal.

Sometimes founders who lose control of their Boards are pushed out because the Board is convinced that the visionary is no longer needed, now that the business roadmap is clear. They think that the visionary may distract focus from the cash-cow parts of the business. The most famous example of this is Steve Jobs’ departure from Apple, only to triumphantly return later. Jobs remains an inspiration to founders everywhere, particularly those who have faced losing control of their BoDs (Interestingly, Recode reports that some Uber directors worry that former CEO Travis Kalanick — who was ousted — is trying to game the outcome in his favor, especially after he told several people that he was “Steve Jobs-ing it.)”

Are You Game for Multi-Track Entrepreneurship?

Every person's motivation for a side hustle or hobby that has business or nonprofit elements to it is different, but if you are enjoying your side hustle, this activity can serve as a break from your daily focus area and routine that can be personally liberating as well as potentially lucrative.

I've found that given how much I love business, marketing, and advertising, simultaneously deploying my brain in both a cause marketing / nonprofit context and the agency and technology (platform invention) context is refreshing and invigorating, particularly because my hobby business is a nonprofit.

To each their own (on however many tracks one is comfortable on)!