It takes different strokes to move a company

In his latest column – “Starting and Finishing” – Fred Wilson writes about the different skill sets needed to found a company and then to build the business. Many times the founder is not the person to take the company to the finish line. As Fred says, “The skills that get you from idea, through initial product, past product market fit, and into a market leading company are very different from what it takes to manage a 200-500-1000 person global business that needs to execute well across a range of dimensions and keep everyone aligned, motivated, and working well together.”

Too many people these days are focused just on starting (raising money) and not enough on finishing (building a growing self-sustaining business). Can a founder make the transition to full-time CEO? Definitely, as I outlined in my post “When can a founder be a good CEO?” This is a very interesting topic for me since I have lived many of these issues, which I think helped me become an effective CEO.

I spent my first four years out of school teaching at Naval Nuclear Power School. Working for one of the world’s largest bureaucracies, I learned by observation many important lessons on the challenges of managing a large organization. I also had my first exposure to a top-notch leader who I could watch in action. Spending over 1,000 hours in the classroom also helped me develop tremendously valuable teaching and presentation skills.

I then started a business with my own money, which taught me the many challenges of running a business. After years of doing that I took a corporate job for 19 months working for one of my previous customers. The experience there was valuable as I learned how large companies bought technology.

I then founded a venture-backed technology company that we built from zero to over $50 million in annual revenue and a $200 million exit. After that I jumped into another startup as CEO and was able to launch a product that attracted a nine-figure acquisition from a Fortune 500 company.

The common theme through each step of my career has been learning from every experience. If I had never worked for any organization other than my own, I don’t think I would have been nearly as effective as a CEO.

Like most athletes who are better off spending some time in college to mature both emotionally and physically before moving on to the pros, the best CEOs have a broad set of skills and experience they have developed over their life. If you try too hard to short-circuit all of these experiences, I think it is hard to fully develop your capabilities. The best advice I can give is this: Focus on finding positions where you can learn and develop without biting off so much that you can’t recover from a failure.

Related Article:

Student Entrepreneurs: If Peter Thiel Calls — Hang Up (Mike Olson on LinkedIn)



  1. great article… and so very true!


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