When did 'entrepreneur' become a dirty word?

The novelty of entrepreneurship is changing

In one of my earlier letters, I stated, “building a business has never been easier, but building a profitable one has never been harder.” I also explained that “the world has slowly shifted from wins being defined by selling what people need to what people want, and technology is merely a host of that virus.”

Today’s entrepreneurial landscape reflects both of these realities. Why? Because anyone can start a business now, and whether it turns a profit or not often seems secondary. In fact, the very definition of success in business has changed, with society questioning whether the novelty lies in creating a profitable venture or merely one with an exit strategy. Meanwhile, our financial world teeters precariously, balancing debt on one side and supercomputers on the other. Public money moves at lightning speed, investing has been democratized, and SaaS businesses continue selling inflated dreams to investors still hunting for the next "New New Thing."

Fighting the stigma

The revolution of computer technology in the '90s sparked a generation widely labeled as "entrepreneurs," who swarmed the hives of Silicon Valley in a hunt to find the key to the future of technology. These pioneers became rockstars, gracing Rolling Stone covers while painting a picture of Silicon Valley as the Eden of creativity on our planet. Soon, more money flowed through Palo Alto than Wall Street, and the youth of tomorrow began dreaming of California beaches, with surfboards in one hand and Macs in the other, instead of grinding 12-hour days at a trading desk.

Today, especially if you’re under 30, telling someone you’re an entrepreneur often triggers a few familiar stereotypes: they might assume you’re involved in crypto, running an OnlyFans, coding the next big app, or constantly fundraising. While there are certainly other paths, these are the ones that dominate public perception. In a world where building a business has never seemed more accessible, older generations often question the legitimacy of your venture unless you can prove it’s turning a profit. For many of them, the idea of entrepreneurship still carries the expectation of tangible results - solid revenue, a steady customer base, or at least something they can understand from traditional business models. If your business doesn’t fit that mould, it’s met with skepticism, as though the ease of starting a venture today makes it less credible.

The fear of risk must not be a preventative

The truth is, the tools to become a solopreneur have never been more widely available. Between online universities, digital courses, virtual learning, and social media, the internet provides a colossal structure of resources for the next generation of entrepreneurs. As Musk once said, “you can learn almost anything off YouTube.” So why discredit the next generation for taking a leap? Is it their fault when investors cry wolf as soon as things go sideways? Of course not. Founders are smart on selling investors on a concept that’s probably going to fail, and while this appears a fashionable trend, the investor’s greed often outweighs their logic.

The challenge lies in the fact that natural human tendencies will always result in a cohort questioning any disruptive or innovative movement that goes against the status quo. However, it’s basic economics that as the barrier for entry loosens, the competitive market increases. We can certainly expect that as technology democratises starting a business, that the volume of poor start-ups in the ether will increase. But while entrepreneurship may not carry the same "cool" factor it once did, it’s easy for a generation to look back and be sentimental.

I have a theory that the current generation isn’t fearful of failing, but failing publicly, even if the financial risk is small. With every action amplified through social media, being branded a failure publicly increases their perceived risk-factor. However, the fear of failure should never prevent aspiring founders from taking risks. It’s those very risks that spark the movements capable of transforming perceptions and changing the stigma around entrepreneurship.