Business Mistakes Learned the Hard Way: 5 Entrepreneurs Share their Story

Where are you in your entrepreneurial pursuits? Idea stage? Development stage? Growth Stage? Whatever stage that may be, there is excitement and uncertainty. Many of us know to seek out mentors, business coaches, and peers about their experiences and insights. For good reason too: learn from them. Listen to their advice. Take their words of wisdom and apply it to your own situation. Yet, regardless of where we are in the process, we will encounter obstacles and problems. We KNOW we will make mistakes; we KNOW there will be failure, but we fight to minimize the depth of failure. However, there are situations that pop up without warning or they creep up on us to create havoc. These 5 entrepreneurs share their story and lessons learned:

Jennifer Tamborski

Jennifer Tamborski, Virtual Admin Experts: “Hiring people and being a leader is entirely different from the corporate world. I hired employees and set them loose, assuming they knew what I knew. When they came back to me confused and lost, I realized I didn’t have the processes necessary for my employees to effectively perform their job. It’s a process I had to learn as I taught them.”

Lesson learned: a clear, concise, communication and documentation plan must be established. Follow-up with employees is just as important as follow-up with clients.

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Chris MacLellan

Chris MacLellan, Whole Care Network: “My theological background inspired me to trust without hesitation. That approach to life did not transfer well to business. I didn’t discover this until I handed over the IP (intellectual property) to a business connection in which the gesture was not reciprocated. As a result, I lost lots of money and my humility. It took a great deal of time to restructure my business, much of which conflicted with my trusting nature.”

Lesson learned: Life skills do not always transfer well to business skills.

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Mary Scott

Mary Scott, Make Believe TV: “Create a clear, contractual arrangement for each project which includes payment agreements and pricing for situations that influence the service offered. All decisions must be clear and understood before the project (or any part of the business arrangement) begins. If it isn’t clear, it will cost a lot of time, money, and frustration.

Lesson learned: Do not rush into a project without the proper documentation.

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Angie Monko

Angie Monko, Harmony Harbor Coaching: “I jumped into business without a clear plan, quickly becoming distracted by multiple business objectives. I didn’t recognize the situation until ~18 months later when cash flow and momentum declined. It took another 18 months to create a business plan and to begin recovery.”

Lesson learned: Create a business plan, follow it, and revise as your business shifts and grows.

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Paul Heirendt, True Bearing Advisors: During my corporate days, I had ‘two young guys’ working with me. They frequently joked, ‘You’re not the boss of me’, which resulted in them learning very little and becoming a liability rather than an asset. I eventually left the corporate world and took one of these young guys with me. As his urging, we moved into his uncle’s free office space in downtown St. Louis. The caveat: the uncle’s son must become the CEO of my company. With no written partnership and nearly 100% of the company in my name, I dealt with legal issues, lost opportunities, lost revenue, and lots of bad blood.”

Lesson learned: It’s better off not partnering unless each member can prove their value AND share the same business goals.

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These entrepreneurs faced some crushing blows to their business growth but regrouped, adjusted and recovered. Communication and documentation were the top business issues. How can you apply their lessons? Share your ideas or stories below.

Kristen Edens
Kris the Scribbler

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