Custer’s Last Stand, the Dade Massacre, and Your Business

On June 25th, 1876, Lieutenant Colonel George Armstrong Custer infamously led 210 men into battle against 2,000 Sioux and Cheyenne warriors. Although it’s commonly believed no U.S. soldier survived, historians believe there was at least one man who made it out of the conflict alive.

Approximately 41 years earlier, a lesser-known U.S. military commander led his men into a similarly disastrous situation. Army General Francis L. Dade 107 took men on a mission to relocate a Seminole tribe. But, the soldiers were ambushed by 180 Black Seminole warriors, and just 3 of Dade’s men survived.

In both instances, the leaders ignored advanced intelligence and severely overestimated their forces’ abilities to carry out their respective missions. Additionally, both tragedies were completely avoidable, but neither leader would listen to reason and allowed arrogance and the pursuit of glory to cloud their judgment, resulting in senseless slaughters.

Entrepreneurs should take these historical tragedies to heart. Particularly when they don’t see any real downsides. It’s not easy to get past legitimate confidence but it’s quite dangerous to overestimate what can be realistically accomplished. So, let’s take a few moments to look at how such attitudes can lead to unnecessary, messy, and costly mistakes, and offer strategies for entrepreneurs to maintain a healthy balance of confidence without veering into hubris.

The Perils of Arrogance in Small Business: Avoiding Costly Mistakes

Small business owners often wear many hats, juggling the roles of visionary, manager, marketer, and more. While confidence is a crucial trait for any entrepreneur, unchecked arrogance and overconfidence can lead to a series of missteps that can threaten the very survival of a business.

The Pitfalls of Arrogance

It all starts with ignoring market feedback. Arrogant business owners might dismiss customer feedback or market research, believing their vision is infallible. This can lead to products or services that don’t resonate with the market, resulting in poor sales and wasted resources. For instance, a restaurant owner might ignore diner complaints about the menu, leading to decreased patronage. But, this example certainly isn’t all. Here are some more common mistakes:

  • Overlooking financial prudence. Overconfidence can lead to lavish spending on non-essential items or ventures without proper financial analysis. This might manifest as spending on an extravagant office space or an unnecessary expansion, draining cash reserves that could have been used for more critical operations.
  • Underestimating competition. Thinking you have no real competitors can blindside a business when a new or existing competitor gains market share. An example is a local bookstore owner who believes their personal touch is enough, not noticing or preparing for the rise of online book retailing.
  • Poor decision making. Arrogance can foster a culture where questioning decisions is discouraged, leading to groupthink. Decisions made without diverse input can miss critical flaws, as seen in businesses that pursue a flawed product launch without sufficient critique.

And last but not least – neglecting relationships. Overconfidence can make owners dismissive of their employees, suppliers, or partners, damaging relationships vital for business success. This can lead to high staff turnover, supply chain issues, or missed collaborative opportunities.

Strategies to Avoid These Mistakes

Fortunately, there are several strategies you can use to prevent your company (and yourself) from falling into such traps. However, none of these measures are easy and will prove especially difficult. And it begins with the most difficult – the ability to cultivate humility. You should regularly seek and genuinely consider feedback from employees, customers, and peers. Humility involves acknowledging that you don’t have all the answers and being open to learning. Still, this probably won’t be enough. So, here are some more steps to take:

  • Engage in continuous learning. Stay informed about industry trends, new technologies, and business strategies. Workshops, seminars, and reading can keep your knowledge current and prevent complacency.
  • Financial discipline. Implement strict budgeting and financial oversight. Use cash flow projections and financial advisors if necessary to make informed spending decisions rather than emotional ones.
  • Competitive analysis. Regularly analyze competitors not just for weaknesses but also for strengths and innovations. Adopt a mindset of healthy competition rather than dismissive superiority.
  • Inclusive decision making. Foster an environment where team members feel safe to challenge ideas. Diverse perspectives can lead to more robust business strategies.
  • Relationship management. Invest in your relationships. Acknowledge the contributions of your team, maintain good terms with suppliers, and engage with your community or customer base.

What’s more, utilize basic risk management. Always consider the worst-case scenarios in your planning. This doesn’t mean being pessimistic but rather being prepared for various outcomes, which can mitigate overconfidence.

Arrogance and overconfidence are not just personal flaws; they are business risks. While confidence is essential in entrepreneurship, it must be balanced with humility, curiosity, and a willingness to adapt.

By fostering an environment of continuous learning and open communication, small business owners can not only avoid costly mistakes but also pave the way for sustainable growth and innovation.

Remember, in the world of business, it’s not about being the loudest voice in the room but about ensuring that voice is informed, considered, and collaborative.

Want to Accomplish More?

Do you want your company to grow faster and earn more while you spend more time with your family doing all the things you started your business to do?

We can make that dream a reality. Give us 30 minutes and we will show you how to get your life back. Skeptical? Good! Put us to the test.

You can call us for your free appointment at 480-240-1226, or, if you prefer, send us an email. You can also visit us at Waters Business Consulting Group to learn more about us and the services we offer.

Like this article?

Share on Facebook
Share on Twitter
Share on Linkdin
Share on Pinterest

Related Posts

I Want to Create a New Position for My Small Business – So How Do I Go about It?

August 25, 2022 No Comments

Entrepreneurs wear many, many hats. It is not at all unusual for a small business owner to perform several different roles. But, this Jack of all trades, master of none can’t go on in perpetuity. The longer it lasts, the less chance there is that the business can scale up. In order to grow a company, it’s necessary to have help and many business owners reach a point where it is unavoidable. So, they make a few hires but still continue to perform various functions until they realize that a new position will free them up to pursue their main goals. Hiring should Equal Growth It’s very common for small business owners to be nervous about their first hires. However, they eventually get past this and the team settles into a comfortable routine. This can easily result in a false sense of security and it’s not at all unusual for the owner to slip right back into or continue bad habits. If a heavy workload causes your employees to feel overwhelmed and frustrated, it may be time to add new positions to your department. Hiring an additional staff member or two can help you split tasks between employees more equitably and give employees the time they need to devote to their work. —Houston Chronicle Sure, someone has to perform those functions and the owner typically feels it is his or her responsibility. But, there comes a time when it’s clear that handing off at least some of those tasks to someone else would be very beneficial. What generally holds a business owner back is not having a clearly defined position, as they did with previous hires. Fortunately, there are some steps you can take to create a new employee position. How to Create a New Employee Position for a Small Business When it becomes obvious that you’re taking on too much, be it administrative tasks or something else, it’s time to seriously consider hiring someone to do that work for you. Here are some steps you can take in order to create a new employee position: Estimate its ROI. Before you start posting job openings, take some time to work out the most likely return on investment. Ask yourself if one or more of your current employees can assume these responsibilities. If not, then it is more likely you need to create a brand new position. Just work out a realistic scenario on how much this will add to expenses and what size return of investment you’ll get for this potential hire. Determine if it’s part or full time. Next, you’ll need to determine whether this is a part-time or full-time position. Go over your schedule and create a ballpark figure of how much time you spend on these tasks. This will give you a pretty good idea of the number of hours you’ll give over to a new employee. Plus, it will tell you how much time you gain back doing more important things. Compile a list of applicable skills. Last but certainly not least, you’ll need to create a list of applicable skills that a new employee would need to possess. This will also tell you if these responsibilities are truly interrelated or if they are a mixed bag. What’s more, it will point you in a more specific direction and help you to hone in on the right personality. What other suggestions do you have for an entrepreneur who is considering creating a new team member role? Please share your experiences and thoughts so others can benefit from your input! Interested in learning more about business? Then just visit Waters Business Consulting Group.

Read More »

The Hidden Risk of Undercutting Prices in Small Business

December 4, 2025 No Comments

We’ve all heard that giving people more for less is a clever business strategy. After
all, who doesn’t want to pay a lower price for a given product or service? Most
consumers will jump at the opportunity to save a little money. But this philosophy
doesn’t always apply. And sometimes, it can backfire big time. That’s right—lower
prices don’t always translate into higher sales levels. In fact, lower prices may have a detrimental impact on a business’s bottom line. But why?

Read More »