The Hardest Parts of Growing a Business

The Hardest Parts of Growing a Business

The Hardest Parts of Growing a Business

Growing a business is no easy feat, and there are numerous challenges that entrepreneurs face along the way. To provide you with valuable insights, we’ve gathered 15 expert opinions from CEOs, founders, and other business leaders. They discuss the hardest parts of growing a business, ranging from maintaining work-life balance to task prioritization.

  • Maintaining Work-Life Balance
  • Handling Increasing Competition
  • Scaling a Cohesive Team
  • Preserving Quality During Expansion
  • Challenges With Distributing Equity
  • Hiring the Right Leaders
  • Building Brand Credibility
  • Validating Niche Ideas
  • Changing Obstacles Stemming from Revenue
  • Competing with a Limited Budget
  • Securing the First Deal
  • Cultivating a Strong Company Culture
  • Adapting to the Market
  • Managing the Cash Flow
  • Ensuring Proper Task Prioritization

Maintaining Work-Life Balance

As an entrepreneur, there are few things more difficult than finding a sustainable balance between your business and your personal life. It’s not a cliché that when you’re growing a business, you never really stop working—there have been plenty of days where work has followed me home, around the house, and even to bed as I think things over.

This is not sustainable and can actually hurt your business in the long run. You need to find a balance where you can power off the part of your brain that’s responsible for the business and engage with other aspects of your life. Easier said than done, of course, but ‌having a small physical ritual to separate the two works wonders.

Try physically closing your computer and putting it in a drawer at the end of the day— it doesn’t really matter what it is, as long as it’s something you do every day to mark the end of your work.

Onno HalsemaOnno Halsema
CEO, Contentoo

Handling Increasing Competition

One of the hardest parts of growing a business is navigating increasing competition. As a business expands and gains success, it inevitably attracts the attention of both new and established competitors in the market.

This heightened competition demands constant innovation, adaptability, and vigilance to stay ahead of the curve and maintain market share. To effectively manage the competitive landscape, a growing business must stay up-to-date with industry trends, foster strong customer relationships, and continuously invest in research and development to differentiate itself and create a sustainable competitive advantage.

This challenge is particularly difficult because it requires balancing resources between addressing immediate needs and planning for the future.

Will GillWill Gill
Event Entertainer, DJ Will Gill

Scaling a Cohesive Team

As a business of one, I struggled for years to scale my time. It didn’t make financial sense to pay someone else to do the things I could do, especially on non-revenue-generating activities. In the first few years, growth took the form of price increases and offering new services.

A few years ago, I started looking more closely at ways I could grow my business without raising my prices. I built a team of writers who could support more client work as well as new services I could offer that didn’t require huge time investments. These ideas seem obvious now, but the path to growth isn’t always black and white. I feel like these next steps to growth revealed themselves when the time was right.

The longer you work on your business, the better you’ll be able to spot these opportunities.

Alli HillAlli Hill
Founder and Director, Fleurish Freelance

Preserving Quality During Expansion

Scaling my business while retaining the standard and integrity of my products has to be the most challenging aspect of any expansion. This demands thorough preparation and execution, as well as considerable time and resource commitment.

I make sure that my staff is the appropriate fit and has the knowledge and experience needed to enable growth. In addition, even as my company grows, I need to keep my focus on providing excellent customer service. This can mean integrating new operational management methods and procedures and coming up with fresh marketing and promotion strategies for my company.

Overall, the fundamental challenge is consistently balancing expansion and sustainability, while keeping the needs and preferences of my customers at the forefront of my business strategy.

Adam WrightAdam Wright
CEO, Human Tonik

Challenges With Distributing Equity

It’s difficult to decide how much equity each owner of the business should receive. Additionally, if the business takes on additional investors or partners, it can become even more complicated to apportion equity appropriately. This is because ensuring that everyone gets an equitable stake in the company requires thorough research and analysis of what percentage of ownership would be fair and advantageous for all parties involved.

It’s important to make sure equity is fairly split in order to prevent future disagreements and ensure everyone is properly compensated for their investment or contribution. Furthermore, it’s vital to review the company’s ownership structure periodically as the business grows and evolves.

Shelby OliphantShelby Oliphant
Director of Operations, Bryar Wolf

Hiring the Right People


Finding the right leaders, delegating work, and finding the right employees. Building a business is all about finding, evaluating, and hiring the right people to do the job better than you.

However, this is the hardest mind-switch for entrepreneurs, because in most cases, you think you can do things better than the people you hire. In some cases, this is true, but in others, you have to let it go.

You cannot build a business without being great at hiring and finding the right people.

Matt WarcholinskiMatt Warcholinski
COO, Brainhub

Building Brand Credibility

I run a digital marketing company that primarily acquires clients through a variety of digital channels. That means having a positive online reputation and appearing credible is crucial for successfully signing new clients. But establishing your brand can be very difficult when you’re starting from nothing.

We have the domain expertise and experience that potential clients are looking for, but the upstart company simply doesn’t have the same brand recognition and hard-won reputation as more established players. This is a problem that can be overcome. It just takes a lot of work to get out in front of customers and demonstrate your unique competencies when you’re relatively unknown.

Temmo KinoshitaTemmo Kinoshita
Co-founder, Lindenwood Marketing

Validating Niche Ideas

Knowing if your niche idea will fulfill the industry need that you’ve envisioned, and creating a product or service according to that idea.

An idea can sometimes misunderstand its industry, and sometimes a product or service gets lost in translation from idea to creation. It can be a challenge to not only take a great idea but also translate it into real life and make it work for the industry need that you originally sought to fulfill.

Shideh KavianiShideh Kaviani
President, Naked Wardrobe

Changing Obstacles Stemming from Revenue

Drawing from my experience as a founder, investor, and operator, businesses face distinct challenges depending on their revenue levels:

$0-1M revenue: At this stage, businesses consistently struggle with finding product-market fit. The challenge is to figure out what to sell, identify the target audience, and reach them in a reliable manner.

$1-10M revenue: The hardest part here is ensuring consistent quality in service delivery. Businesses now understand what to sell and who to sell it to, but they must establish processes and secure the right talent to deliver their products or services at a larger scale. This can be particularly challenging for businesses offering non-standardized services.

$10M+ revenue: At this level, businesses often find that their primary channel plateaus, limiting further growth. Consequently, they need to discover and develop secondary and tertiary channels to maintain growth, which can be as demanding as finding product-market fit multiple times.

Rafael Sarim ÖzdemirRafael Sarim Özdemir
Founder and CEO, Zendog Labs

Competing with a Limited Budget

Competing with larger brands on a smaller budget is one of the hardest parts of growing a business.

As a business owner, it’s important to make a living from your business but also to generate profits you can reinvest for further growth. While some entrepreneurs strike gold and quickly reach that reinvestment stage, most must build their businesses slowly and steadily.

Established brands often have the advantage of investing more easily in areas such as conversion rate optimization, content writing, link building, and pay-per-click advertising. This enables them to grow even faster, making it difficult for smaller businesses to catch up. Finding creative ways to stretch limited resources to compete with big brands can be a significant hurdle for entrepreneurs seeking to expand their businesses.

Axel DeAngelisAxel DeAngelis
Founder, NameBounce

Securing the First Deal

The hardest part of being an entrepreneur is making those dreams a reality—closing your first successful deal. It is a milestone that every entrepreneur has to get through, and it can be incredibly daunting.

Despite investing time and money in building a wonderful website, I was nervous about how clients would respond and perceive my product. I was worried about whether the marketplace would be accepting or not.

But once I closed my first successful deal, that apprehensive feeling was replaced with tremendous confidence and motivation. Everything henceforth was about making improvements, scaling up, and branching out.

Nick RivadeneiraNick Rivadeneira
Founder, Racebuilds

Cultivating a Strong Company Culture

Maintaining a strong and cohesive company culture can be challenging as a business grows. The influx of new employees, processes, and locations may dilute the organization’s core values.

To mitigate this, businesses must actively communicate and reinforce their culture while fostering an environment that encourages open dialogue and empowers employees to contribute.

Aysu ErkanAysu Erkan
Social Media Manager, Character Calculator

Adapting to the Market

Adapting to market changes is one of the toughest business growth aspects. It requires high flexibility, willingness to change, and constant vigilance. The market is constantly evolving, and keeping up with new trends and emerging consumer needs can be challenging.

Staying ahead of the curve requires a deep understanding of your industry and a willingness to invest in new technologies and techniques. As a business owner, you must always seek opportunities to improve and innovate. It’s a never-ending process that demands hard work and a willingness to take risks. Adaptability and staying ahead of the curve are the keys to success in business.

Adrian PereiraAdrian Pereira
Co-founder, Eco Pea Co.

Managing the Cash Flow

One of the hardest parts of growing a business is managing cash flow.

Cash flow refers to the movement of funds in and out of your business over a period of time. It is necessary for any business, regardless of size, to maintain adequate cash flow as it pays for everyday operations, such as inventory and payroll. Failure to manage cash flow properly can lead to serious financial problems, which may even put the future existence of your company at risk.

In order to successfully manage your cash flow, you must implement best practices such as tracking spending, creating budgets, monitoring accounts receivable and payable closely, paying vendors on time, pursuing debt collection in a timely manner, negotiating payment terms with suppliers or customers when possible, taking advantage of early payment discounts, and using financial software to gain better visibility into your finances.

Irina PoddubnaiaIrina Poddubnaia
CEO and Founder, TrackMage

Ensuring Proper Task Prioritization

When growing a business, there are a lot of different tasks that need to be completed in various aspects of your business. It can be challenging and overwhelming to prioritize different tasks and identify what you should spend your time and money on.

My one tip for prioritizing your business tasks is to define the current goal you’re working towards (i.e., gain more clients, become more profitable, increase conversion, etc.). Before starting a task, ask yourself if this task will bring you closer to your goal. If the answer is “no,” try to identify the right time to complete this task and focus on a different one that will bring you closer to your goals.

Inbar MadarInbar Madar
Founder and Business Consultant, M.I. Business Consulting

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