Entrepreneurship is not for the faint of heart, a fact starkly illuminated by these figures: 20% of newly established businesses falter within their initial two years, a number that swells to 45% within the first five years and escalates further to 65% within the initial ten years. Only 25% of new businesses endure for 15 years or more. Yet, in the face of such daunting odds, why do numerous entrepreneurs with solid business plans and palpable passion find themselves on the path to failure?


Let’s dive into the most common entrepreneurship challenges, shedding light on the crucial aspects of selecting a service or product, developing a sales strategy, establishing starting funds, combating burnout, navigating staffing issues, expanding wisely, managing cash flow, bridging the gap in marketing knowledge, and making strategic hiring decisions.


Common Entrepreneurship Challenges


Selecting a Service or Product

The first hurdle in the entrepreneurial journey often involves choosing the right service or product. The market is teeming with opportunities, and deciding what to offer can be daunting. It requires thorough market research, identifying gaps, and understanding consumer needs. 

A meticulous analysis of personal strengths and passions can also guide founders in selecting a venture that aligns with their skills and interests.


Developing a Sales Strategy

Once the product or service is in place, the next challenge lies in crafting an effective sales strategy. Many new founders grapple with finding the right balance between aggressive marketing and authentic relationship-building. 

A robust sales strategy involves understanding the target audience, leveraging digital platforms, and creating a compelling value proposition.


Establishing Starting Funds

Financial constraints can act as a significant roadblock for budding entrepreneurs. Establishing starting funds demands careful planning and resource allocation. Seeking funding through various channels such as loans, investors, or crowdfunding platforms is often necessary. 

A solid business plan can make the venture more appealing to potential investors.



One of the most common entrepreneurship challenges is stress. 33% of entrepreneurs struggle with depression and burnout, and it’s not hard to understand why. The entrepreneurial journey is demanding, and the passion that fuels the inception of a business can sometimes lead to neglecting self-care. 

Founders must recognize the signs of burnout, implement effective time management, and cultivate a support network to sustain the long-term health of both themselves and their ventures.



Building the right team is pivotal for the success of any business. New founders often need help attracting and retaining skilled employees. 

A well-defined company culture, competitive compensation packages, and professional growth opportunities can significantly impact staffing success.


Expanding (Wisely)

The temptation to expand rapidly can be alluring, but it comes with its own set of challenges. Scaling too quickly can strain resources and dilute the core focus of the business. 

Founders must approach expansion strategically, ensuring that each step is well-calculated and aligns with the overarching business goals.


Cash Flow

Maintaining a healthy cash flow is crucial for the sustainability of any business. In fact, 82% of small businesses fail due to cash flow struggles. 

Entrepreneurs often grapple with delayed payments, unexpected expenses, and economic downturns. 

Implementing effective cash flow management strategies, such as invoicing promptly and negotiating favorable payment terms, is essential for financial stability.


Lack of Marketing Knowledge

It’s 2023, and a solid online presence is non-negotiable. However, many new founders need more marketing knowledge to navigate the complex world of digital marketing. 

Investing time in learning or hiring a marketing expert can bridge this knowledge gap, ensuring the business effectively reaches its target audience.



As the business grows, the challenge of making strategic hiring decisions becomes paramount. Bringing the right people on board is instrumental in achieving long-term success. 

Owners must define clear job roles, conduct thorough interviews, and prioritize candidates who align with the company’s values and vision.


Bottom Line

The hurdles entrepreneurs face are numerous, from selecting the right service or product and crafting a compelling sales strategy to managing finances, combating burnout, and strategically expanding. Staffing decisions, cash flow management, marketing expertise, and informed hiring add complexity. 

Yet, despite these daunting odds, the resilient entrepreneur can turn entrepreneurship challenges into opportunities. By addressing these common obstacles head-on and implementing thoughtful strategies, founders can buck the statistics and build a resilient and enduring business.


Dan Marzullo is Founder & CEO of Drafted, a content marketing agency, Mentor for the UCCS Scale to $1M Boot-Up Camp, Certified Entrepreneurial Mindset Facilitator, and Career Development Instructor at ACC. Click here to learn more about Dan and work with him.