At its core, The American Dream has always been about entrepreneurship. But due to mass employment by large corporations – and the rise of cushy jobs with benefits – recent decades have seen entrepreneurship become less popular. Fortunately, digital advancements and a shift of values has helped reintroduce entrepreneurship as an accessible and viable employment option for many.

Coinciding with this shift is an increasing recognition of the people who make it on their own. We’re pretty passionate about helping entrepreneurs too, which is why we’re doing our part to celebrate Entrepreneur’s Day this year. Here’s what you should know about the history of this celebratory day, and how entrepreneurship is transforming with time.

Recognizing Entrepreneurship

It’s no coincidence that Small Business Saturday is held during November, which was established as Entrepreneurship Month by president Obama in 2012. Both of these celebrations can be traced back to Grasshopper co-founders David Hauser and Siamak Taghaddos, who teamed up to create Entrepreneur’s Day in 2010. Entrepreneur’s day was originally founded to recognize contributions to entrepreneurship, business, innovation, and job creation.

Now, Entrepreneur’s Day has inspired an entire movement that includes Small Business Saturday, a yearly presidential proclamation, and an entire month dedicated to the mission. Grasshopper’s co-founders and friends are even working to make Entrepreneur’s Day an official US holiday to be held on the third Tuesday of every November.

Given the many contributions that entrepreneurs and small businesses provide, one month of recognitions doesn’t feel like enough. But in a world fueled by global corporations and impersonal connections, Small Business Saturday and Entrepreneur’s Day remind us to support their hard-working contributions throughout the year.

Trends in Entrepreneurship

As defined by The Small Business Administration, a small business is a company that employs less than 50 people (in the manufacturing field) or less than 100 (in wholesale trade). By this definition, there are currently 28.8 million small businesses in the country, and that number is only projected to rise.


However, it’s interesting to note that America’s small businesses are actually getting smaller. In fact, the average size of small businesses has shrunk by nearly 20% (according to Intuit), and 96% of small businesses have 50 or fewer employees (SBA). Furthermore, new businesses are making a point of staying lean and nimble, because it helps them get ahead faster.

Women-Owned Businesses

As entrepreneurship becomes more accessible, the parameters around who owns small businesses – and how and where that work is done – have shifted. This has led to another important trend amongst the small business community: the rise of women entrepreneurs.

The 2016 Kauffman Index of Startup Activity reports that last year, the rate of female entrepreneurs saw its largest increase in two decades. The same report noted that “female new entrepreneurs have a higher likelihood of being opportunity entrepreneurs than do their male counterparts, with 84.6 percent of the new female entrepreneurs in the 2016 Index not coming from unemployment, compared to 78 percent for males.” This means that more and more women are becoming entrepreneurs in an effort to seize an opportunity and pursue independent employment, not because they have to.

Solopreneurs and Independent Workers

We’ve discussed how today’s small businesses are becoming smaller and more efficient. At the extreme end of this trend is a rising population of solopreneurs – entrepreneurs who work entirely alone. Thanks to apps like Uber, Airbnb, Up Work and Etsy, becoming a solopreneur is easier than ever.


And as more people leave the office for their own personal ventures, businesses small and large are working to accommodate this trend. Remote, freelance, and contract roles are a popular choice for businesses because they enable on-demand adoption of talented, impermanent employees. Without the need to provide office space or benefits, independent contractors are a dream come true. The small business report by Intuit projects that by 2020, 43% of the US economy will be comprised of on-demand workers.

Entrepreneur’s Day asks us to consider the ever changing landscape of entrepreneurship, and how new trends and technologies are redefining what it means to achieve The American Dream.