Catching up with old friends is one of the best parts of visiting Seoul, a city where I used to live some 20 years ago.

One such friend has recently started his own venture after spending many years as an executive with investment banks and most recently with Google’s Merger & Acquisitions team. After years of targeting successful startups for acquisitions, he was hungry to do something on his own.

Now, as his web-based company is nearing its launch, he was both excited and concerned. The “execution” component of the plan had taken some toll on him: The long hours, the personnel issues, the repeated re-evaluation of the plan, and the constant self-doubt while always having to be a cheerleader to the rest of the team.

He has a good plan, the one that had him excited six months ago. But now, the inertia of day-to-day execution has clouded that vision a bit. He just needs a friend to tell him to look up once in a while. These are typical cycles that all entrepreneurs go through.

There is a big difference between the mindset of investors who are used to asking the tough questions and modeling businesses versus those who start such businesses. The former are taught to be skeptical but attentive for key “models”. The latter are eternal optimists who believe in a vision and are driven by their passion.

Some people can make that jump across investor-to-entrepreneur divide, but it is not a natural thing. The jump the other way from entrepreneur-to-investor seems to be an easier transformation.

Regardless, I look forward to his eventual success.