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DK: A lot of startup people and business people talk about the “trial by fire” approach. Do it, tweak it. Ship, then test. Lots of advice, but it’s hard to know when to stop analyzing and press ‘Go.’ Any thoughts on knowing when to take the leap?

DG: Business decisions and life decisions are similar. You have to make them with the best base of information you have at the time.

At the end of the day, [pay attention] if your “gut” doesn’t feel right about something.

All the right numbers or reasons on paper about why you should do something won’t cut it if you aren’t passionate about the opportunity inside.

DK: What about an early-stage entrepreneurs?

DG: At the end of the day, nothing validates success but success. That means getting out and actually doing what you think is the right thing to do.

Focus focus focus on doing one thing well. If you find it isn’t working out the way you planned, adapt.

DK: What should business owners ask themselves as they prepare to leap from a words-on-paper business plan to a real-life enterprise?

DG: To help make this business decision process easier, ask yourself some questions:

1. Can I defend my decision from a (market, competitor, service, ROI, unmet demand) standpoint?
2. Have I thought through risks and have strategies to mitigate. Are there some risks I am willing to take regardless and if so why?
3. If I don’t do this, what is the “cost” in terms of lost opportunity? Will someone else come along and steal my idea in the near future? Will I lose business to someone else already in the market?
4. What’s the worst thing that could happen if I proceed? (that I can anticipate happening, at least)
5. What does my gut tell me when I wake up at 5 am thinking about this? Is it the same answer at 5 pm? Always let your body tell you what your brain may not want to.