by Matt Thomas

Meet Julie and Jake. They are both mid-market CEOs. Julie runs a well funded SaaS company. She co-founded the business with a close friend who has since moved onto another project. Now Julie sits alone at the top of a healthy organization with dry powder, optimistic investors, and a newly formed board of advisors. She recently graced the cover of a popular technology magazine and is celebrated as an up and coming CEO to watch. Her company consistently ranks high on national “Top Places to Work” lists. Julie’s executive team is strong and in a recent company wide leadership evaluation, the feedback was nearly unanimous. Julie’s people love her and they trust her.

Jake leads a large manufacturing operation. He bought the business from his dad 5 years ago, has tripled revenue, and recently acquired two of his biggest competitors. Privately held, the buck starts and stops with Jake. He has a reputation for being aggressive, unpredictable, and charismatic. Last year, Jake turned over half of his executive team for the fourth year in a row. Weekly he scrolls through the glassdoor reviews trying to guess which former employee posted each negative review. For the past two years he has worked with an executive coach focusing primarily on vulnerability in the workplace. He has not made much progress. Jake’s people fear him and they do not trust him.

Other than industry and origin story, what separates these two? They are both bright, driven, and eager to leave their mark on the world. Their organizations have clear vision, values, and strong financial models. From the outside looking in they would both be viewed as tremendous success stories. So what gives?

A mentor of mine recently hit his 80th birthday. In a recent small gathering of friends, he took some time to talk about what he has learned along the way. For decades this individual was a high profile leader of large organizations. He has written dozens of books, mostly on leadership, traveled all over the world speaking to groups of up to 100,000 people, and counseled both Presidents and foreign dignitaries. The scale of his influence would be difficult to quantify. He has aged gracefully but has not escaped without his fair share of wounds and the scars to prove it.

He reflected on a season in which he made a very public mistake and the subsequent fall out for him and his family. In some circles, his reputation was forever tarnished. He experienced, first hand, the fragility of success.