This essay sheds light on the dark side of entrepreneurship and elucidates how to avoid loosing money as an entrepreneur when growing brands. Moreover, how to alleviate depression as an entrepreneur is delineated in this essay. The dark side of entrepreneurship is often an overlooked topic since it is out-shined by rare entrepreneurial success stories that grossly embellish the life of an entrepreneur. In spite of its merits, entrepreneurial endeavors have a proclivity to go awry and culminate in egregious failures for prospective entrepreneurs. At least 70% of business fail within the company's initial ten year period and cannot stay afloat in the long haul in spite of all the goodwill, brand equity, brand loyalty, and brand recognition they accrued over the years. The crux of the issue lies in prospective entrepreneurs not having the business acumen to be able to consistently grow nor efficaciously run a successful business in the long haul. They simply do not understand that a successful business is all about unalloyed innovation, shrewd marketing, and robust communication with customers. Building a brand as an entrepreneur is an eminently challenging endeavor with no paved road to guaranteed success and does not always culminate in a successful outcome in spite of the entrepreneurs best strategic efforts. Establishing a profitable brand may require tens of thousands of hours of strategically and incessantly working hard seven days a week for decades as you attempt to deliver unprecedented value to the marketplace. Since the job prospects as a future employee are so grim and bleak for college graduates, it seems as though the only viable career prospect in a hyper competitive marketplace is being a full-time entrepreneur. Allocating thousands of hours applying for low paying jobs is an unwarranted, loss of time investment. This is because, the search for a job simply bears an enormous opportunity cost. The precious time squandered on completing meaningless job applications can be otherwise earmarked towards fostering a potentially profitable brand with no earnings cap. Attention is undoubtedly the new currency of the digital era. Millennials emphatically understand the importance of entrepreneurship and brand building to attain wealth from selling product placements, earning royalties, and generating advisement revenue. Moreover, millennial content creators also understand the importance of brand build so that they eventually receive subscription revenue, generate sponsorship revenue, and reap monthly Patreon donations from patrons. In spite of its merits, entrepreneurship is not without its plethora of dire issues. The dark side of entrepreneurship can be multifaceted and usher in a host of issues into the entrepreneur's life. First, entrepreneurship typically involves years of agonizing struggles as you undergo the toils and travails of building a brand from the ground up. Amid this brand growing time period, it is unlikely you will generate any profits. Furthermore, you will essentially be working unpaid which can culminate in you depleting your savings and liquidating any asset you might have just to sustain yourself and keep your brand afloat. Entrepreneurs must be willing to work unpaid to grow their brands and may even go years without receiving a single penny from their brands. Second, your personal life will be comprised and adversely suffer as you consistently pursue your entrepreneurial endeavour. In other words, as you devote the majority of your finite time into growing your brand and a building a prospectively profitable business, you will not only work long hours each day, but will also struggle to maintain relationships. This is because, your life will be dedicated to turning your business profitable as the never ending bills further pile up. This new focus on cultivating a profitable business will overshadow the need to prioritize your relationships with others.