Love Your People (eBook)

Introduction

“I feel stuck.” I listened intently as the first-time CEO paced the room, nervously running his hands through his brown hair. “We’re growing, but our growth has slowed. I know I’ll need to raise more money soon, and I’m already exhausted. I spend most of my time at work and hardly any at home with my wife and kids. I don’t know how much longer I can do it.”

Mark was young and intelligent. He’d already been successful in larger corporate endeavors, and now he had clearly built the right product for his market. So where had things gone wrong? His pacing slowed, and he looked down.

“Truth is, I’ve never felt more alone. When I look around, I can’t tell if my team is in it like I am. I don’t know if they truly understand what I’m trying to build.”

I nodded with understanding. As a former CEO and now a CEO coach, I’ve heard several versions of Mark’s narrative many times.

He explained how he spent most of his time on operating issues or problems, feeling like he constantly watched over his people to ensure they did things the right way. He began to question whether or not he could make this business as successful as he knew it should be, and he doubted himself, embarrassed that he didn’t know what to do.

Unfortunately, Mark’s predicament is not unique. Most entrepreneurial leaders run into a similar situation at some point in their journey.

If you’re in this situation, don’t give up. The world needs people like you, and this book is written for you. I’ve found that solutions exist to all these problems, and they all rely on effective leadership, which is exactly what this book teaches you.

Learning Entrepreneurial Leadership Firsthand

My passion for growing businesses and people started at a very young age. My father was a union pipefitter, and after working for other companies early in his career, he decided he could do it on his own. His company, Rely-on Fire Protection, installed fire sprinkler systems in buildings throughout Pittsburgh. I vividly remember helping him build his first work truck in our driveway, affectionately named “Sanford” after the 1970s junkyard show Sanford and Son. He started with an old 1967 International cab, and he welded a custom steel bed frame specifically designed to carry pipe for his new business. He built a bed out of wood, and I felt lucky to help him bolt the planks onto the welded frame. Now, looking back as a parent, I’m sure I was more trouble than help, but as a young kid, I believed I had assisted him in building that truck and, therefore, his business.  

I also have the painful memory of watching him shut down the business a decade and a half later. The decision to close his business was necessary but devastating to our family. As with most entrepreneurial families, my father’s business permeated our entire lives. As uncomfortable as this experience was for me and my family, it helped shape me. It lit a desire in me to assist great people in creating amazing businesses.

Unfortunately, it took me a while to realize my purpose: my gift for growing great businesses and people. Because of my father’s failed business experience, he strongly encouraged me to work for a Fortune 100 company where I could “make a lot of money and have the security of working for a large company.” He didn’t want me to experience the pain of trying to make payroll and the stress that goes along with running your own business.

I started working for large companies like GE, US West, and Avaya. I quickly climbed the ranks of finance, operations, and other general management roles, taking a brief break for business school in between. However, it wasn’t until more than a decade into my career that I reconnected with my passion. I was working for a large telecommunications company that wanted me to launch an in-house incubator to generate new revenue streams. It was part startup and part venture capital inside the well-funded safety of a larger corporation. In a very short period of time, we succeeded in starting, buying, and growing a handful of businesses within our corporate umbrella. It was fun, and we were incredibly successful.

This experience ignited my passion for growing businesses and building great teams. It formed the foundation for many of the principles I teach today. Largely, these businesses succeeded because of the people running them. I was fanatical about attracting and hiring the best people. I found that if I helped set the vision and the framework for success and then got out of the way, these businesses thrived. I provided my people the autonomy to do the work the way they wanted, and then I supported them when they needed help. I discovered that this simple recipe became the roadmap to growing great entrepreneurial businesses.

Shortly after my corporate venture experience, I felt it was time to leave the shelter of a large corporation. I left to help grow and scale a new payments software startup in Denver named PaySimple. As one of the first few employees, I transitioned from leading several thousand people and managing billions of dollars in revenue to guiding just a couple of people and almost no revenue. I also moved from a spacious office and large expense account to a small office in a loft above a Mexican restaurant. And I loved it. I spent less time in meetings and more time creating. We assisted small businesses by ensuring they collected and managed their cash effectively, which was the exact problem that had put my father out of business years earlier. I was fired up. I had found a home where I could put my passion to work.

My PaySimple days taught me how to be truly entrepreneurial. We scrutinized every dollar we spent, and time was of the essence. By design, every day, we spent a lot of money, investing in people, tools, and systems to grow. As a guy who was used to generating a lot of cash in my other, more established businesses, this made me uneasy. Fortunately, the founder, Eric Remer, remained calm and steady as we worked through these early days. From Eric, I learned that vision and belief play a huge role in entrepreneurial leadership. Rarely does a startup move in a straight line from idea to success. Typically, businesses make many changes along the way. Through this experience, I learned that belief and a clear vision are critical parts of effective entrepreneurial leadership. At the time of this writing, PaySimple now trades on the Nasdaq under the name EverCommerce.

In my days since PaySimple, I’ve run multiple businesses and have been fortunate enough to experience many successful exits. I refined the principles I share in this book in a business named Zen Planner—a software company focused on helping fitness businesses. I was fortunate to have led Zen Planner for seven years, growing it by more than 50 percent a year. A dozen publications recognized the company as the best place to work. We were wildly successful, and we had a hell of a lot of fun. We ultimately sold Zen Planner in 2017, which generated a fantastic return for those involved.

I’ve used my proceeds to invest in many entrepreneurial ventures and to co-launch a venture capital company named Springtime Ventures, which holds investments in more than forty companies at the time of this writing. I’ve also coached dozens of CEOs and now serve as executive chairman for more than a half dozen companies, most of which are investments of a fantastic private equity company, Mainsail Partners.

Over the course of my life and career, I’ve learned a lot about entrepreneurial leadership. Above all else, I’ve discovered that to be a great leader, you must love your people.

Why Love?

I’m very consciously using the word love—a word that people are so afraid to use in the business world. Don’t be afraid of it. Love is an opportunity for you to excel above your competition by attracting the best talent and enabling them to thrive.

In the business sense, love is the opposite of fear. If you were looking for a job, would you want to work at a place where you were loved or where you felt afraid—one where you want to perform because you know your leaders care about you, or one where you must perform because you’re afraid you’ll lose your job or face criticism if you don’t?

Unfortunately, way too many leaders still lead by fear. I know this because I used to be one of those leaders. They are authoritative and commanding, and they believe that instilling fear in people motivates them to perform. This may have worked for my grandfather, but it doesn’t work anymore. This old thinking is just screwed up. I’ve hired many leaders who have achieved some degree of success in larger organizations but failed dramatically in entrepreneurial roles. Their experience in each differs for a reason. Unfortunately, many corporate environments still reward old-school command-and-control leaders. And as long as they reward those leaders, we likely won’t see much evolution in the leadership of those organizations.

On the other hand, entrepreneurial leaders focus on winning the hearts and minds of their people. And to do this, they must understand what their people actually want.

I fundamentally believe that people want to do great work. They want to be successful. They want to participate in something special and know that they are contributing to a meaningful impact. It is up to you to love your people by setting them up for success and helping them...