What I’ve Learned In Ten Years as a Bootstrapped Entrepreneur

What I've Learned In Ten Years as a Bootstrapped Entrepreneur

2006 was a memorable year for a lot of reasons. Facebook opened its doors to the general public. Zinedine Zidane headbutted Marco Materazzi during the World Cup Final. And for some reason, Americans paid a total of $62 million to watch Snakes on a Plane.

But the most important event for me in 2006 was founding my company, gothamCulture.

Last month marked my company’s ten-year anniversary. And as I reflect upon my journey of bootstrapping and growing a professional services firm, I came to the conclusion that what I’ve learned might benefit other entrepreneurs out there who may be growing their own businesses.

I learned many of these lessons the hard way, and I hope they help you avoid the same mistakes.

1. There is a difference between being self-employed and being an entrepreneur. I learned this lesson from a mentor in 2009. It’s a difference that can be illustrated by answering one question: Do you spend your time working in the business or working on the business? Those who are self-employed tend to work in the business, delivering the goods or services that the company provides. Entrepreneurs, on the other hand, focus on growing the business and letting other professionals deliver to customers. It may seem like splitting hairs, but I can tell you from experience, this is a fundamental distinction that had a profound impact on the future of my entrepreneurial journey.

2. Hire the best people for the job at hand. This goes for employees as well as key vendors who can help you focus on the things you do best, like accountants or lawyers. You’re not an accountant, and while you may think that you’re being fiscally responsible by trying to do everything yourself, these activities are likely not something that you’re a) passionate about doing right and b) not something you have the right skills for. Having the right team enables you to focus on activities that have the most impact. Learn to rely on experts so that you can move the business forward in other ways.

3. Leadership is not role-specific. I’ve experienced this throughout my professional life, both in the military and the civilian worlds. I’ve also seen that it’s a terrifically underutilized resource. Just because someone holds a lower role in your organization doesn’t mean they don’t possess tremendous ability to influence others. The trick, I’ve found, is to identify these people and to develop them for roles where they can use that influence in the best interest of moving the company forward.

4. Demand excellence and remove roadblocks quickly. High-performing people often begin to resent those who don’t bring their A game every day. By creating a culture where exceptional performance is the goal and team members are mutually accountable, we’ve created an environment where people are free to raise challenges and concerns and work out solutions to roadblocks. If someone on the team doesn’t meet our mutual expectations, the message is clear and quick. If that person doesn’t get on board, they don’t last long. Your culture isn’t going to be for everyone.

5. Always have a contingency plan (or three!). Things very rarely go according to plan. Rather than rolling the dice and hoping for the best, I learned early on to be very intentional about planning for contingencies. They say in the military that your plan only lasts until the first shot is fired. After that you have to rely on your training. You must be able to adapt in very uncertain environments. Preparing for contingencies rarely results in you having a perfect plan for any possible outcome, but it does help ensure that you’re thinking critically about the variables and you’re not relying too heavily on your primary plan panning out no matter what.

6. It’s all about relationships. People do business with people they know, like and trust. I learned this lesson from a former janitor at the University of Michigan who went on to found and grow one of the largest janitorial services companies in the state. Developing and nurturing honest and mutually beneficial relationships is what makes the business world go round.

7. The structure of your compensation model has a significant effect on day-to-day behavior in the organization. Make no mistake, every system and process in your organization will have significant impact on behavior. I’ve become a self-taught expert on the topic of compensation planning over the years, as I have seen the unintended consequences of these plans play out in surprising ways. Take extreme caution when designing your systems and processes to ensure that they are reinforcing behaviors that align with your values.

What I've Learned In Ten Years as a Bootstrapped Entrepreneur8. Every decision we make in terms of our processes is made with the field consultant in mind. Everything we do must from a support standpoint must relieve our field staff from administrative tasks. While we’ll never completely eliminate administrative tasks from our folks in the field, we make every effort to design our systems so our team can spend their time doing what they do best: serving our clients. It’s surprising how quickly a bureaucracy can develop that saddles people with activities that add no value. It’s something you must constantly be on the lookout for. Give your team the tools and support they need to do what they do best.

9. Transparency allows for honesty and trust. My company is an open book. This transparency removes doubt and establishes trust. It also allows for honest dialogue that engages the entire team in providing their ideas and input in ways that have more impact. Because they understand the details of the business, they are able to inform their thinking and provide much better input to help drive the business forward.

10. No matter how well you think you’re communicating; myths will begin to form. These myths may hold people back if they aren’t surfaced and talked about. I make it a practice to listen very carefully to not only what my team says, but how they say it. Minor variations in wording can send clear signals that myths and fables are beginning to spread. This is my trigger to refocus my communication efforts to set things straight. If you don’t actively manage the collective narrative, you may wake up one day to a company that bears no resemblance to your intentions.

11. Play like someone else’s sole mission in life is to eat your lunch. I consider this lesson to be my personal key to success over the years (and it may have stemmed in no small part from some kid taking my lunch in elementary school). At its core, it’s really about passion and hunger. If I can attribute my personal success to any one thing, it would be that I never rest. I never stop to pat myself on the back and I never take my foot off the accelerator. This is because I realize that there are other folks out there who get up every day determined to stake their claim and put us out of business.

I certainly don’t have all the answers. The lessons I’ve learned over the years have come at a cost, but they have been invaluable. I’ve made mistakes (BIG mistakes!), but each one has taught me a critical lesson that I’ve been able to apply in the future.

There is no one right answer in the life of an entrepreneur. No one right path or recipe for success. And it’s exactly this fluidity that make entrepreneurship so appealing to me and others I’ve met over the years. What are your biggest lessons learned? I’d love to hear your own story in the comments section of this article so that we all might continue to learn from each other.

This article originally appeared on Forbes.

 

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