Why Failure Is Your Friend

By Hayes Drumwright, CEO of POPin

I wrote my new book, Management vs. Employees, based on my own experiences as a serial entrepreneur in multiple industries. The book addresses a major problem that has plagued companies for decades: How can leaders bridge the power gap between management and employees in a way that inspires both to engage?

As a serial entrepreneur, I’ve bootstrapped several businesses that have generated over $500 million in annual revenue. However, much of my book involves revealing stories of personal failure that I’ve encountered along the way. My goal is to illustrate the mindset and methodologies that leaders must take to succeed.
How have I failed? Let me count the ways. At age 25, I launched a tech company that grew to $23 million in revenue, only to soon implode – forcing me to lay off more than 100 people and shutter the business.

I launched my next IT company with just $100 of my own money, and I bootstrapped it to $400 million in revenue without any outside funding. Then at one point, we ran into a serious cash crunch, forcing me to cut salaries by 20% across the board. You can imagine how that went over – so badly, in fact, that I was ousted by the senior leadership team and soon left the company to build my current startup, POPin.

My laundry list of missteps also includes a venture capital firm that didn’t make a single investment for four years, and a Napa Valley winery that had to destroy eight of our first 13 barrels of cabernet due to shortfalls in quality. You get the idea: My path to success has been paved with some very clunky bricks.

As for my new book, I have sought to apply these life lessons to help other entrepreneurs avoid similar mistakes. Throughout many ups and downs, I have found that’s it critically important to close the gap on apathy and entitlement at all levels of an organization in order to create an engaged workforce that can scale up organically. In fact, this has become my ultimate goal and mission in business.

This book provides corporate leaders with a roadmap to bridge the hierarchical gaps separating management and employees to gain company-wide acceptance of transformative strategic initiatives. Real-world examples demonstrate how to take responsibility for uncovering and fusing the inspiration potential at all levels of your organization, and how to neutralize the insidious culture of fear and apathy.

Why is there a divide between management and the employees they lead? Why does each group have such an incredibly hard time understanding the other? Why do over 70% of corporate initiatives fail? It isn’t because of a lack of communication from the top. And just talking louder isn’t going to fix it.

Most every turnaround CEO knows that the answers for turning around a company lie within the company. The job is to unlock those answers by building trust with the employees in the trenches. It is a pretty simple plan, but with so much employee apathy directed towards management, building that trust can be difficult.

Entrepreneurs, CEOs, and everyday leaders can learn something from watching a turnaround. They can learn how to avoid it. At some point in a startup’s growth, there gets to be too many employees for the founders to have personal relationships with. Then in almost all companies there will come a period of hardship where leaders will have to make tough decisions that employees don’t understand or agree with. This is when apathy will get a foothold.

Apathy is the killer of trust with management. No matter the amount of your outbound communications, if you are talking to apathetic listeners, your initiatives to scale the business will fail. If companies keep driving corporate goals down their employees’ throats with one-way communication methods, they shouldn’t be shocked by lackluster results. I have published my book in response to this reality, in the hope that it will enable other leaders to nurture a transparent and curious culture that engages employees to join in as enthusiastic accomplices in the larger strategic plan.