Always be a First-time Entrepreneur
Why? The history of the industry is filled with successful startups led by people who’ve never “done it before”. You’d think that being a second-time entrepreneur is actually better than being a novice. I’ve found things to be quite the opposite. A first-time entrepreneur is better capable of an effective response to out-of-process contingencies that occur in the real world. They let go off ideas that aren’t working, tend to talk less and are more generous at offering new solutions to old, relevant problems.
That’s who my money would back. And yet, a second-time entrepreneur needn’t forget that they can learn to be both.