When does someone become an entrepreneur? In my case, I suspect it was always embedded in my nature.
Early in life, I believed that I had skills that were marketable. I started my own business as a teenager, around age fifteen or sixteen, the age when most kids are getting jobs and getting a driver's license—all that proto-adult stuff. A lot of my friends got jobs at restaurants, so I did the same… for about one week. That’s when I realized I'm not a manual labor kind of person. It was a pivotal experience for me. I felt I would be doing the world a disservice if I did not go out there and do the best I could to create my own opportunities, for myself and for others. That led me down the path of entrepreneurship
I mulled over what I had learned from the working/job route, thinking about what wasn't for me, and in so doing, inspiration struck. I realized I wasn’t destined to be a miserable failure or a service-industry drone. The skills needed for restaurant work—or retail work in general—weren’t my skills. Where I excel is assessing problems, creating plans, designing software, and helping people understand that there are better ways to do things.
So, instead of going back to the restaurant job, I started a company.
I went to an older friend who could help me fill out the incorporation paperwork. The idea was a technology company, specifically focusing on desktop computers that we would build from scratch. Building non-gamer PCs may sound kind of silly or unimpressive by today's standards, but this was before you could walk into a Best Buy or Walmart and buy a computer off the shelf. I believed that it was a company with great potential.
At the start of what became my first entrepreneurial venture, we were using my parents’ house as our “corporate office.” After the laborious work of building our first computer, we were naturally eager to see our creation come to life. But when we flipped the switch on our very first computer—darkness. And I mean darkness everywhere. We had overloaded the power supply to the house! Soon after, my parents decided we needed our own workspace, so we went to find work and an office.
The lesson? Always be prepared to pivot, because you never know what’s coming next.
Eventually, our work building computers led to building software programs to carry out small actionable items for businesses. That naturally progressed to doing network installations. We basically did anything related to technology, and it was a great proving ground for me. The work helped me refine who I was and what type of technology I wanted to embrace to help others. I gravitated to the software side of things because software is adaptable to planning, and that’s my strong suit. My objective: How do I get from A to B, and how do I get other people from A to B?
I ran that software and hardware company for three or four years, at which point I met some folks at a networking event who owned a similar company. We eventually merged our firms, and the rest is history. We've been working with each other in various capacities and different startups for more than twenty years.
That’s the abridged version of my start as an entrepreneur. I suspect most people don’t go down that path so early in life. But I’d like to believe that everyone who finds the entrepreneurial path does so because of an insight or pivotal moment, like the one I had in my teens.
For me, that pivotal moment was born out of inspiration. There are moments when we realize we can do something better or, as in my case, that we aren’t cut out for what we are doing with our lives… or—even better—both. That’s what keeps entrepreneurial-minded people motivated. It’s not necessarily money or fast cars or other material things that motivate us. Reaping some rewards for our efforts is just a bonus. Our real motivation is in the creation and execution of a vision. Entrepreneurs are people with dreams who speak and act too loudly and passionately to be ignored!
I’ve been traveling through the startup world for so long that I quickly recognize defining moments for the company and its owners and employees—moments that either cement who they are or inform how they will evolve and who they will become. This is always an indication that the company is pivoting. That pivot can lead to great success, or it can instead be the first step on the road to failure.
Looking over the whole entrepreneurial timeline, I will talk about some examples from different startups that I’ve been involved in. As I write this book, I am acting CEO of Cicayda, the third company that we've started in the legal space, and I’m engaged in merger and acquisition talks that could lead to the company being acquired by another firm. We've launched startups, and assisted other companies in other verticals, but we've focused on the legal sector for a while now.
The patterns outlined in the following pages represent critical growth phases. My aim is to provide you with as much insight as possible into these phases ahead of time, so that you can plan for growth instead of flying blind into the maelstrom.
For simplicity’s sake, I’ve laid the book out in six sections:
Chapter 1: Know Thyself helps you assess yourself, your strengths, and your weaknesses in relation to leading a company.
Chapter 2: Know Thy Company lays out the stages your company will go through from startup to maturity.
Chapter 3: Know Thy Role combines the first two chapters and talks through the different roles you will play as your company grows.
Chapter 4: Cultivate Thyself is about filling in any gaps you may have noticed about yourself while going through Chapter 3. You could also call it “personal growth.” It’s also about taking care of yourself so you don’t burn out and impair your well-being as you grow your company.
Chapter 5: Right People, Right Places looks within your company at the most important resource you have—your people—and helps you to understand how to empower them to be their best, for their own sake and for the sake of the company.
Chapter 6: Strengthen Your COAR offers the model—actually a mantra—that I use in large and small ways to help me lead and grow my companies.
My entrepreneurial career has been primarily concentrated in the technology sector—the software space, to be more precise—so the stories I tell and examples I offer are centered on software businesses. But the lessons I’m talking about here are universal. They apply to anyone with an entrepreneurial spirit who is drawn to the world of company-founding and leadership. This story revolves around growth patterns—both your own and that of your company—and gives hints about what to expect and how you should prepare.
(Note that I won’t be covering specifics about business operations and management. My colleagues, Glenn Hopper and Billy Hyatt, have their own books that extensively cover those topics. As such, I’ve asked them to weigh in here in places where their observations are relevant to the topic.)
My goal with this book is to point out the inevitable revolutions that all entrepreneurs go through as they start, grow, and let go of companies, one after another. You may recognize your own experiences as you read, you may see solutions to current issues, and you may get ideas about what’s on the horizon for you. Wherever you are, and whatever business and/or personal space you are in, I’m confident that you’ll come away with valuable and useful insights.