I Wouldn’t Wish Entrepreneurship On My Worst Enemy

“Entrepreneur” has turned into a buzzword. Entrepreneurship isn’t sexy. It’s not glamorous. It isn’t really even fun. It’s pain. It’s angst. It’s often more stress than any human should have to endure. And it doesn’t matter how “successful” you are. You are still susceptible. Cameron Herold told me that he got hit with a monstrous…

Failing My Podcast Interview with James Altucher

I had just wrapped up eight in-person interviews over three days with Toronto entrepreneurs and I’m now headed to the Big Apple for an interview with James Altucher. Let’s back up a couple months. I email James about being interviewed on my show. He replies to that initial email within five minutes and says, “Sounds good. I’m…

What I Learned from Nik Tarascio, CEO And Aviator

It’s a Sunday evening in New York City and Nik and I meet up for dinner over indian food in Murray Hill. We share a meal and walk over to his apartment by the Flatiron building to record the conversation. I wish I recorded everything. The most interesting conversations happen with no microphone on. It…

Taking Calculated Risks and Elevating Your Network

Jayson Gaignard was heavily in debt, had driven his business into the ground and was starting to hit rock bottom. He was creeping closer and closer to filing bankruptcy. At this point, shockingly, he decided to do two things. First, he decided to max out $10,000 on a credit card for an event Tim Ferriss…