What Not to Do: Lessons from My Biggest Business Failures and What I'd Do Differently

What Not to Do: Lessons from My Biggest Business Failures and What I’d Do Differently

Failure is often described as life’s greatest teacher. Looking back on my entrepreneurial journey, I’ve found this to be absolutely true. My path has been filled with successes, but it’s the failures that have shaped my perspective, refined my strategies, and helped me grow into the business owner I am today. If I had known then what I know now, I would have avoided many costly mistakes. My goal in sharing these lessons is to help you sidestep the pitfalls I fell into and build a sustainable, vision-driven business.

1. Starting Without a Vision

One of my earliest mistakes was diving into businesses without a clear vision or long-term plan. For example, my first major venture, Audio Empire, achieved rapid growth but lacked a defined purpose. We were busy growing, but we didn’t know where we were headed.

The Lesson: Every business needs a “North Star”—a guiding purpose that informs every decision. Without it, you risk losing focus, which leads to wasted time and resources.

What I’d Do Differently: Before starting any venture, I’d spend time defining its core mission, setting measurable goals, and establishing a clear roadmap. This vision should be revisited regularly to ensure the business remains on track, and the associated goals should be broken down into incremental steps to ensure the best likelihood of success and achievement of the vision. Don’t be scared to stretch yourself beyond what you think is possible. 10x your goals!

2. Neglecting Proper Planning and Systems

When I launched a construction company, I failed to prioritize systems and planning. We had no budgets, no proactive accounting, and no project management tools. This lack of structure led to slowly finished or unfinished projects and financial inefficiencies.

The Lesson: Strong systems and clear project management are non-negotiable. They ensure operations run smoothly, projects stay on schedule, and costs remain under control. Expectations should be clear to everyone involved, and performance should be evaluated very frequently based on those expectations.

What I’d Do Differently: I’d implement tools and processes early on to track expenses, allocate resources, and monitor progress. Hiring experienced operations specialists would also have been a game-changer.

3. Ineffective Team Management and Role Alignment

I’ve made the mistake of hiring employees who needed to be told what to do at every turn. These “doers” relied on constant direction, which meant I had to do the thinking for everyone. This approach stifled growth and created unnecessary stress.

The Lesson: Successful teams are built on proactive problem-solvers. Employees should be capable of taking ownership, defining the path to desired results, and implementing plans.  The only thing needed from you should be the desired end result and how that task or project relates to the overarching strategy of the business.  

What I’d Do Differently: I’d clearly define desired outcomes and hire people who could figure out how to achieve them. While “doers” may have a place in certain roles, they should be supervised by “thinkers” who can lead effectively.

4. Mismanaging Deferred Maintenance

In my personal real estate portfolio, I failed to realize that my property managers often prioritized repairs over capital expenditures (capex).  I failed to properly account for the difference, or set appropriate budgets for each so that I could identify when repairs were being made when capex was needed instead. This lack of oversight resulted in deferred maintenance and significant financial strain playing catchup on years of "bandaid" repairs on major problems.  It also resulted in hundreds of thousands of dollars or repairs with no long term value, money that could have been spent on the needed capex instead.

The Lesson: It’s crucial to differentiate between ongoing repairs and long-term capex. Proper budgeting for both is essential to prevent small issues from snowballing into major problems.

What I’d Do Differently: I’d create detailed budgets for repairs and capex, review them regularly, and adjust as needed. This would ensure sufficient spending on preventative maintenance while controlling repair costs.

5. Over-Leveraging Without Strategic Reserves

I’ve also learned the hard way about the dangers of over-leveraging. At one point, my real estate portfolio was so heavily leveraged that unexpected expenses created immense stress.

The Lesson: Leverage can accelerate growth, but it must be paired with financial safety nets. Building reserves for predictable but infrequent expenses is critical.

What I’d Do Differently: I’d strategically set aside reserves for taxes, insurance, capex, and make-readies. These dedicated funds would provide stability during lean periods and reduce the financial strain of unexpected costs.

6. Ignoring Expert Advice

One of my biggest regrets is not acting on advice from experienced team members, like Noel, who urged me to implement systems and budgets in my construction business. Ignoring this advice proved costly.

The Lesson: Listening to experts and acting on their recommendations is essential for growth and efficiency.

What I’d Do Differently: I’d foster a culture where feedback is valued and implemented. Seeking out and trusting advisors early on would have saved me significant time and money.

7. Lack of Exit Strategies

Both my property management and construction companies became burdensome because I hadn’t planned for how they would scale or exit. I held on too long, which drained resources and energy.

The Lesson: Every venture should begin with the end in mind. Whether it’s scaling, selling, or shutting down, a clear exit strategy is essential.

What I’d Do Differently: I’d outline exit strategies from the outset, ensuring they align with the business’s goals and my personal vision.

8. Defining and Living Your Desired Company Culture

One of the most overlooked yet critical aspects of running a successful business is defining your company’s culture and core values. I’ve learned that if you don’t specify to your team how they should act and what they should believe, they will default to their own interpretations of what’s right. This can lead to misalignment and inefficiencies.

The Lesson: Your company’s culture should be a reflection of your personal core values and beliefs. Once you’ve established these values, you must “walk the walk” by referencing them daily and modeling them in every interaction. Doing so will make it clear who truly aligns with your vision and who does not.

What I’d Do Differently: I’d define my core values and integrate them into every aspect of the business. Regularly communicating these values ensures everyone on the team understands the desired culture. Employees who aren’t aligned will quickly become apparent, and having a team of true believers will dramatically enhance the effectiveness, profitability, enjoyment, and overall success of the business.

9. Defining Your Role and Building the Team

Understanding your role within your business is essential for long-term success. Are you the operator or the visionary? Will your role evolve over time? Without clarity on these questions, you risk spreading yourself too thin.

The Lesson: Identify your desired role early and plan how your responsibilities will evolve as the business grows. Building the right team around this clarity is equally crucial.

What I’d Do Differently: If I’m not going to be the operator, the first (or possibly second) hire should be an operator who can oversee day-to-day operations. If you hire an assistant first, ensure they have the potential to grow into an operator role. From there, the operator should build the team around their own strengths, weaknesses, and needs (with your input of course). This strategic approach ensures efficiency and alignment as the business scales.

Conclusion

Looking back, every failure contained a valuable lesson that has shaped my entrepreneurial philosophy. From the importance of vision and planning to building strong teams and financial reserves, these experiences have taught me what not to do.

My hope is that by sharing these lessons, you can avoid similar pitfalls and build a business that is not only successful but also sustainable and fulfilling. Remember, failure isn’t the end—it’s an opportunity to learn, pivot, and grow.

What lessons have you learned from your own failures? I’d love to hear your stories and insights!