Ashley Bloom talks startup lessons, the investment mindset and futurism with the prolific entrepreneur, Dan Martell.

Feeling weary just before midnight, I was met by the steely gaze of Dan Martell, a proud Canadian, husband, and father of two young boys. He’s a five-time tech startup co-founder (two failed and formative, two successful acquisitions), frequent investor and 500 Startups mentor, with all his current focus on Clarity, a platform for paid business advice via phone calls.

Within a few minutes it’s as though I’ve downed a long black or two, buoyed by Dan’s high energy and very Canadian earnestness.

His biggest two lessons from failed startup number one (Maritime Vacation) and two (New Brunswick Host):

1. He picked too small a market (Canada only, and the very specific niche of cottage vacations that was limited to a market of 300). The action step: Think bigger than your neighborhood, street and…