David Gardner is a serial entrepreneur and angel investor based in Cary. He sold ProviderLink to Compuware for $12 million in 2006. Four years later, he sold Peopleclick to a New York private equity firm for $100 million. Among his portfolio of 25 local startups are FilterEasy, Stealz, Validic, ArchiveSocial, FotoSwipe and Fortnight Brewing. He had two exits in 2013: Magnus Health (after it raised a round) and ChannelAdvisor.

Gardner wrote The Startup Hats over Christmas 2013 and it is now available for purchase in both paperback and ebook. He shares excerpts of each chapter with ExitEvent readers in 13 installments. Here’s part eight. 

Special deal for ExitEvent readers: save 70% on The Startup Hats. On December 9th, The Startup Hats ebook is available for $2.99 for Kindle, Nook and Apple devices. 
The manager’s hat is the one hat that will enable you to take off all of the others to some degree. If entrepreneurs read and benefit from my little book here on how to put on the startup hats, then I would seriously consider writing another book called “Taking off the Startup Hats”. It would focus on how to grow your venture beyond the startup phase by effectively learning to delegate those hats and responsibilities to others. 
Successful entrepreneurs are typically movers and shakers by nature. We are almost always ambitious type-A personalities that move fast and get things done, but these beneficial traits early in a venture can turn to work against us when it comes to the seemingly slow and inefficient tasks of management, responsibility, delegation and company culture building. 
What we can get by with in a small team can become a major problem as your venture grows, which unchecked can even be the primary cause of an otherwise excellent venture’s failure. You pretty much have to be a control freak to successfully wear all of those startup hats required to get your company going, but you have to learn how to take them all off if you want to grow your company beyond what you as one individual can achieve. It’s a bit of a paradox. The very personality traits that make you successful in the first place will cause you to fail just a short time later. 
The reason I’m qualified to speak on this subject is because I was once a really bad manager. I sold some of my companies way too early and left a ton of money on the table simply because I could not master the art of management, and it was stressing me out. This is a very common problem for entrepreneurs. Of the dozens of startup technology companies that I grew up with that went public, I can think of very few where the founding CEO was actually able to make the transition from great entrepreneur to great manager. I’ve always had a tremendous respect for the late Steve Jobs who struggled so mightily with this transition that he actually quit the company he founded, but then returned years later with newly acquired management skills that enabled him to lead Apple to unimaginable new heights. 
As a full-time investor and advisor now to early-stage startup companies, I spend a lot of time talking to my CEOs and helping them with the various issues they are facing. I have found it far easier mentoring them in how to put the hats on then in how to take them off. 

The manager’s hat is so different from all of the other hats. The other hats are about doing stuff quickly and efficiently and getting immediate results. Management is not a sprint, it’s a marathon. If the other hats are about hunting, then the management hat is more akin to farming. It requires patience and I know very few entrepreneurs that I would call patient by nature. Being a great fighter pilot does not prepare you to sit in the control tower and direct all of the new fighter pilots. It is a skill that must be learned and it’s critical if you want to continue to grow and remain in control of your venture. 

David explains how to move from cockpit to control tower in the rest of his chapter, available for the devices listed above.

Read other excerpts from The Startup Hats here.