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I was scared when I left the corporate job for the first time. I was even more scared when I was thrown out of graduate school and had to explain why to my parents. When I was first separated and then divorced I was ashamed to tell people about it. When I lost all my […]

Kelly Francis ‏@KellyFrancisLaw: How do you know when you’re thinking too big or aiming too high (if that’s even possible)? Answer: In the mid-90s I had an idea that lasted about the amount of time it takes to drink two beers. I say this because I had the idea at a bar and it was […]

 [Some expanded answers from my regular Thursday Twitter Q&A session] HOW TO DEAL WITH BURNOUT? Lemuel Goltiao ‏@suburbandude: Any advice for someone who’s experiencing burnout? Answer: I have to confess something. I am feeling a little bit of burnout. I’ve been doing this blog for a little more than two years. I probably write, on […]

One time I wanted to sell my company to HBO. The CFO was looking at the numbers. They were willing to buy it for a tiny amount but it was an amount that would’ve taken me about one billion years to save because that’s just the way I roll. I figured I would quit after […]

Scott Miller ‏@sbmiller5: if you have a startup can you succeed if you place personal health and family above business? Answer: I was talking to a fund of funds manager. He was overweight and had a nervous tic. His CFO once called me and said, “James, I don’t know if this is right or not […]

The psycho-pharmacologist asked me, “so what can I do for you today?” and I said, “The only thing you can do for me is write me a check for one million dollars but I doubt you are going to do that.” He laughed. I had been sent to him by a psychologist who couldn’t write prescriptions and […]

I needed some help so I decided to call the richest, most successful person in my rolodex. The only problem is I had no idea if he was rich or not and he wasn’t in my rolodex. But I wrote him anyway and said, “Can I meet with you?” It was in May, 2011. About […]