How These 13 Business Leaders Learned From Their Mistakes

How These 13 Business Leaders Learned From Their Mistakes

We’ve asked 13 business leaders, from managing partners to directors, to share the most impactful mistakes they made early in their business journey and the lessons they learned. From the pitfalls of misguided partnerships to the importance of leveraging industry networking opportunities, this article offers a wealth of insights from those who’ve been there and learned from it.

• Misguided Partnership Distracts From Core Focus
• Inflexibility Hinders Reputation and Expansion
• In-House Marketing Leads to Ineffective Promotion
• Early Investor Involvement Hampers Future Financing
• Underestimating Online Advertising Stunts Growth
• Over-Commitment Leads to Entrepreneurial Burnout
• Over-Reliance on Single Channel Limits Development
• Learn to Delegate and Trust Employees
• Recognize the Value of Outsourcing
• Ask the Right Questions in Underwriting
• Choose a Single Competitive Advantage
• Prioritize Clear Team Communication
• Leverage Industry Networking Opportunities

Misguided Partnership Distracts From Core Focus

Early in my business, I pursued a partnership opportunity that didn’t bring any benefit to the business. Although it seemed like a great idea at first, the partnership ended up asking for services that we weren’t able to provide and were outside of our expertise. This was a mistake because it distracted us from our core focus and led to wasted time. 

From this experience, I learned that starting out; we need to stick with what we know and make sure that each venture complements the primary goal—growth. If an opportunity arises but doesn’t clearly fit within what your business provides, sometimes turning it down is best.

Julia Kelly, Managing Partner, Rigits

Inflexibility Hinders Reputation and Expansion

In the early days of our business, a significant error we made was inflexibility with nearly everything we did. We assumed one-size-fits-all training modules would suffice for every business. For instance, we implemented a generic program for a manufacturing company that was nearly identical to what we’d used for a retail client. 

The difference in industry safety needs was vast, leading to inadequate preparedness. This oversight significantly affected our reputation. The critical lesson we took away was the necessity of tailoring our training to suit each business’s specific needs and industry standards. 

Today, our dedication to adaptability forms the bedrock of our services, enhancing the quality and relevance of our training, which‌ has increased client satisfaction and business growth.

Haya Subhan, General Manager, First Aid at Work Course

In-House Marketing Leads to Ineffective Promotion

As an inexperienced business owner, I made the mistake of keeping the marketing team for my brand in-house. This proved to be a costly mistake for my startup. There was no marketing plan to work with and the software the team was relying on was outdated. 

This resulted in the ineffective marketing of the products/services offered by my business. The revenue generated was much lower than what we had in mind. However, this mistake served as a learning experience for us. 

We sought the services of agency specialists to promote our brand. These professionals had insight into the latest trends and software related to marketing. We could double our sales rate with the help of these professionals.

Eli Pasternak, CEO, Liberty House Buying Group

Early Investor Involvement Hampers Future Financing

One mistake I regret to this day is taking in investors early on when I started my business. We needed money, of course, and we felt that getting some backing from an angel investor would help our business really grow. 

However, we had to really part with a huge chunk of the equity, and once we finally hit scale and needed more money to maintain growth, we found it very hard to raise money by selling more equity. Looking back at it now, we would have been better off working with venture debt or simply trying to bootstrap the business from the start.

Young Pham, Founder and Project Manager, Biz Report

Underestimating Online Advertising Stunts Growth

One significant mistake I should have made early in my business was investing in online ads. As a new business, I underestimated the power of targeted advertising to reach potential customers and drive growth. 

By not leveraging ads, I missed out on opportunities to expand our customer base and increase brand awareness. I learned from this mistake that strategic investment in advertising, particularly in the digital space, is essential for gaining visibility and attracting customers in today’s competitive business landscape.

Michael Sena, Founder and CEO, SENACEA

Over-Commitment Leads to Entrepreneurial Burnout

Running a business can be challenging and demanding‌. Early in my business, I made the critical mistake of over-committing to extra tasks, leaving myself burnt out. 

This taught me an extremely valuable lesson as an entrepreneur to manage my time wisely and be keenly aware of how much of a workload I can handle without stressing myself out.

Brian Lee, Co-founder and CEO, Arena Club

Over-Reliance on Single Channel Limits Development

In my early days, I got entangled with a channel that initially gave my business a much-needed lifeline. The product-market-channel fit was immediate, driving crucial cash flow when the stakes were highest. It felt like a boon, and I unknowingly got stuck in that groove for far too long.

The mistake came to light when I hit a roadblock trying to scale my revenue. The businesses I reached through this channel were smaller, with diverse needs and constrained paying capacities. This was limiting my growth.

Only when I experienced this bottleneck was when I fully comprehended the implications of my initial choice. Theoretical knowledge is one thing, but the sting of experience is an unparalleled teacher. 

Interestingly, I was completely oblivious to this mistake while it was happening. It was an unknown-unknown—the most perilous risk in business. So, always be vigilant for such blind spots, as they may be silently stunting your growth.

Rafael Sarim Özdemir, Founder and CEO, Zendog Labs

Learn to Delegate and Trust Employees

I made the same mistake that nearly everyone does when they first manage their own employees—I tried to do everything myself and burned myself out. 

I had no choice but to learn to trust my employees and learn to delegate. We start businesses because we want agency. Don’t trade that agency for control over every detail. Hire great people, and delegate.

Rick Berres, Owner, Honey-Doers

Recognize the Value of Outsourcing

One mistake I made early in my business that had a significant impact was believing I had to do everything myself. As an entrepreneur, it’s easy to forget that delegating tasks can be beneficial. I thought outsourcing would cost too much and so tried to handle all the roles myself. 

This ultimately led to burnout and wasted resources, as there were areas where I simply wasn’t experienced enough. The lesson here is to recognize when you need help and take advantage of what others can offer. 

For instance, if something needs engineering work but you don’t know how to code, hire a coder rather than spend hours learning it yourself—this will free up your time for other, more important activities.

Amy Ling Lin, CEO, nailsalon.nyc

Ask the Right Questions in Underwriting

It took me multiple attempts to get to what is perceived as the right information in the underwriting sector. Here, you learn more from experience, rather than an already available guide. 

Despite collecting a multitude of information, it’s a few key points that play a major role. We arrive at this by asking the correct questions, which again is a trial-and-error process. What I did is not ask enough questions, which is a prime role of the underwriting team to find a viable solution. 

But, through arduous teamwork, we could produce viable results. Though I had to go through many routes to arrive at this realization, what helped me most was my team. We worked, both individually and collectively, to produce effective results for the company. Since we had open discussions, my mistakes had a minimal impact.

Marco Andolfatto, Chief Underwriting Officer, Apollo Cover

Choose a Single Competitive Advantage

One mistake I’ve made in business was to be “stuck in the middle.” This means that I wanted to compete for both price and quality. I charged less than other digital marketing agencies. And, I delivered a superior product. 

This resulted in my margins suffering and an unsustainable model. The lesson was to pick a direction. Either compete on price, or compete on quality, but don’t do both. This is a common problem among new businesses that are desperate to bring in new clients. 

The best solution is to pick a direction and stick to it. Over time, you will get the right customers and your business will be more sustainable because of it.

Dennis Consorte, Digital Marketing and Leadership Consultant for Startups, Snackable Solutions

Prioritize Clear Team Communication

I didn’t establish clear communication with my team from the beginning, which resulted in misunderstandings, delays, and frustration among team members. 

I learned to prioritize communication and set expectations early on. For example, I implemented weekly team meetings and encouraged open communication channels for feedback and suggestions. 

This mistake taught me that communication is the foundation of a successful business and that it should be a top priority to avoid any potential issues or setbacks.

Roy Lau, Co-founder, 28 Mortgage

Leverage Industry Networking Opportunities

In the home improvement industry, networking is a great way to gain more business opportunities, and the best part is there are plenty of businesses in our industry that help each other out all the time. 

In our early days, however, we failed to see how helpful these connections can be. And although we freely recommended our partners, we should have relayed to them how important it was for us to do the same, too. 

However, we learned our lesson enough and soon stayed in touch with our industry partners to keep reminding them to recommend our services. Now, we are part of a highly active network where bringing one another more business is standard practice.

Neil Platt, Director, Emerald Home Improvements

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