Startup Basics

10 Insights from 10 Years Running a Business

Guest Writer
President and CEO
4 min read
Opinions expressed by Entrepreneur contributors are their own.

It's easy to focus on the glamor of entrepreneurship, as startup worship is turning a growing number of once Average Janes and Joes into global celebrities. But, the truth is, starting a business is incredibly hard work. Even the savviest entrepreneur can't perfectly anticipate the challenges of growing a company.

A decade ago, I co-founded Pluralsight with three very smart and talented individuals. Now, as I look back on my entrepreneurial journey, I humbly offer 10 helpful observations from my 10 years as an entrepreneur and CEO:

1. Find your passion and build from there. Make sure you’re fully invested in your cause since, after all, it’s what you will be eating, sleeping and breathing for several years. At Pluralsight, all the founders were passionate about education. When we realized that passion would sustain us, we quit our day jobs and got to work.

Related: Turn Passion Into Profits? Oprah, Seinfeld and Branson Certainly Did

2. Work with partners who have the same goals and expectations. It is imperative that founders and ground-floor employees share the same vision from the start. It's helpful to go through the exercise of taking the company to a series of possible conclusions so when road bumps occur you'll have the confidence and collective muscle memory of knowing how to deal with it.

3. Don't raise funding without a reason. Too many founders rush into the Series A because they lack discipline or feel it's a rite of passage. Venture backing validates a company and provides essential growth resources, but it also reduces autonomy and can make a startup fat and lazy. Accordingly, it's important to have a very specific purpose for independent financing before getting on the fundraising circuit.

4. Be open to growing quickly through acquisitions. Sometimes an M&A strategy is the best (and quickest) growth path. In our case, our professional audience was hungry for IT, open source and creative content beyond our core software development offering. Using our venture funding, we acquired four companies in eight months to plug these holes and meet customer expectations as quickly as possible.

5. Pivot often. The road to startup success is littered with the remains of companies that were either complacent or too comfortable with the status quo to pivot on their business models. Pluralsight started out as a classroom training company. Eventually, we realized we were limiting our audience with this offline approach. In 2008, we moved our entire business online, a pivot that has paid huge dividends for us.

6. Rally your team around an aspirational mission. Every company needs to know why it exists and the value it provides. Ideally, a company's vision will convey professional and personal growth opportunities for employees and the sense of being part of something that will make a credible impact on the world.

Related: Change the Rules: 5 Ways to Bring Mission Into Your Business

7. Culture trumps everything in hiring. You don’t want your employees and new hires to look at their job as a “desk sentence.” Find people who embody your company’s core values and are a cultural fit.

8. Hire people who are smarter than you. This point might bruise your ego but, in the words of Bill Nye, “Everyone you will ever meet knows something you don’t.” Companies stand to gain from bringing new perspectives, different backgrounds and brighter minds into the fold.

9. Continually improve. Push employees to hone their skills and develop new ones. Consider offering tuition reimbursement programs and paying for certification exams to encourage this behavior. Management needs to continually improve as well. As an executive team, we read a different book together each quarter to make sure our playbook stays focused and fresh.

10. Be OK with being wrong sometimes. Does your work environment embrace new ideas? We understand, as all companies should, that honest attempts at getting it right will sometimes result in failure. That is a rudimentary part of the learning process. As long as failure doesn't stem from negligence or incompetence, it should be welcomed as part of the process that moves the company forward.

Building my first company has been a rewarding, exhausting and enlightening experience, and it's given me perspective I wish I'd had a decade ago. Here’s to the next 10 years!

Related: Afraid of Failure? Think Like a Scientist and Get Over It

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