5 Mistakes I Made in My Business and What I Learned From Them

by Evan Keller

We entrepreneurs thrive on an inner fountain of optimism and courage. While these God-given virtues help us scale astounding heights, they also set us up for catastrophic falls. How so?

We simultaneously and unwittingly possess the ominous dark sides of these strengths we so prize. A healthy optimism can morph into a false sense of invincibility, and taking big risks can yield triumphs – or collapses equally as grand.

In my over-optimism about people (thus extending unwarranted trust), I took these five unwise risks early in my business career:

1) Bad choice of business partner

I took on a business partner I hardly knew who made me angry every single day as I did 95% of the work.

2) Compromise on the fine print

When the fine print of a contract with a national company made me uneasy, I went ahead and signed it after their local representative assuaged my concerns in writing. When he broke his promise, I was stuck in a contract that cost me thousands of dollars while providing no benefit to my company. 

3) Trusting an untrustworthy employee

I employed a mechanic to service our fleet and believed his excuses for not properly documenting his expenses while he spent tens of thousands of my company’s dollars on auto parts for vehicles I did not own.

4) Bad equipment decision

I purchased a $52,000 dump truck from an out-of-state dealer sight unseen without having a mechanic check it out for me, and am still dealing with problems from a poorly maintained truck.

5) Opening a door to the unscrupulous

Before adding a homeless man to our payroll, I had him demonstrate his skills on a jobsite where he broke his leg. He sued for Worker’s Compensation coverage which he was not eligible for because he was not yet on our payroll and since he tested positive for cocaine in his post-accident drug test! We won the lawsuit, but only after a stressful 18-month ordeal.

With ten more years under my belt and far more now to lose, here’s what I’ve learned from these failures:

My optimism is tempered with realism about human depravity and a world where things often go wrong. (Matthew 10:16: “I am sending you out like sheep among wolves. Therefore be as shrewd as snakes and as innocent as doves.”)

Trust but verify. I’m now slow to enter into contracts, and I’ve created employee accountability systems to encourage honesty and expose dishonesty. (Proverbs 27:23: “Be sure you know the condition of your flocks, give careful attention to your herds.”)

All manner of cheats and thieves view a thriving company as a target. I cannot let their evil-doing rob my joy and peace. I pity, not fear them. I leave them to God’s judgment while trusting him for good results as I keep doing business with integrity. (Proverbs 24:19-20: “Do not fret because of evildoers or be envious of the wicked, for the evildoer has no future hope, and the lamp of the wicked will be snuffed out.”)

These darker sides of courage and optimism won’t have the last word. While we must moderate the scale of risk, and manage well the risks we do take, we must still press forward, believing that we can indeed co-create good things with God. (Proverbs 24:16: “Though a righteous man falls seven times, he will get up.”)



Evan Keller has been married to his precious wife Karen of 25 years – a nurse who’s an accomplished cook. Member of Christ Community Church (Evangelical Free) in Daytona Beach and Rotary Club. Enjoys 12 nieces and nephews, close friends, art, the blues, books, paddling, backpacking and basketball with urban kids. Evan is Founder/CEO of Tree Work Now Inc, an industry-leading, multi-million dollar tree company serving 2,000 clients annually. He is also Founder/Executive Director of Creating Jobs Inc whose business mentoring/training programs serve entrepreneurs in Florida, Honduras, Haiti, and Mexico. Author of GrowBook: 24 Essential Drivers of Small Business Success, Evan is also the former Divisional Director of Florida for InterVarsity Christian Fellowship.


GrowBook Developing WorldGrowBook is a 300-page, 25-session business training curriculum on how to grow a healthy company. GrowBook is filled with practical how-to steps and thought-provoking questions on key aspects of growing a business. GrowBook is easy to follow, conducive for discussion, and action-oriented. It is a comprehensive field guide for SME’s, with sections on leadership, market position, production, sales/service, employees, finance, and giving back. Biblical values are integral to each chapter, but are presented discreetly for use in sensitive contexts. Find out more.

GrowBook is available on Amazon for $12, with all profits advancing Creating Jobs Inc’s mission to: “mentor and train entrepreneurs to grow companies, create jobs, and help communities thrive.”

The following editions are currently available:

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