I’m terrified…

Courage is in fact scary. A lot of people admire courage when they see it, but don’t identify it within themselves. There’s absolutely nothing wrong with being scared. However, just like all emotions, you can harness it for something really powerful. Courage can be instinctual, but it is also the internal battle we have inside over action and inaction. It takes courage to be your authentic self, especially if that self goes against the grain.

This is my book, it just happens to be in blog form. Often when I tell people snippets of how I got to where I am today, I’m encouraged to write a book. I weighed all of the reasons for doing so and put it off for many years. Mostly, I wanted the book to matter to someone and to help inspire them with their own life story. I wanted the book to have the biggest impact possible, otherwise why do it?

Before putting all of this out there, the scariest thing for me was public speaking. I somewhat conquered that fear. I spoke a little bit about this journey on the TechCrunch Disrupt stage and after I got off stage, I was approached by some literary agents. A person on Twitter introduced me to an agent that I didn’t realize was one of the best in the industry - Amanda Urban.

I often don’t know what I’m doing, but I forge ahead anyway. So, I took the call with her and it was all incredibly exciting. I wanted to take the plunge and do a book. The problem was that I had a relationship with WME that I valued and I didn’t know how to navigate it. It turned out they have a literary department and I was encouraged to go there instead because of my existing relationship. I let Amanda know and she was incredibly disappointed. She had an amazing vision for this book that would redefine business books and memoirs.

I got to work with my new agent and he found me a writer that I really like. We worked on several proposals, but the agent didn’t think he could sell any of them and didn’t like what he saw.

Meanwhile, I told a few friends about this journey and they all gasped when I told them I said no to Amanda Urban. I learned just how legendary she is. After several rejections from my agent, I decided to go back to her, on my knees, and see if she’d take me back, but she’s understandably not interested.

So, I’m the idiot who turned down Amanda Urban and I’m now walking away from WME and I’m the idiot who’s going to put this book out on Substack instead. I’ve decided I’m not going to follow a formula. I’m going to do this my way. It may be all wrong, but I’ll control every part of it and who knows, maybe some publisher will come along and want to make it into a book after all. Hell, maybe even a movie. Who knows. I was caught up with the mental image of a shiny book, with a pretty cover and the permanence you feel when you author something like that.

Books are great, but they aren’t the only answer to getting a story out there. I love books and if I did this, it would have been nice to have one, but I decided I don’t need it and neither do you. If you want, you can just print these emails and staple them all together when we are done.

So why Ugly Duckling? Well, you’ll just have to find out. I do want to warn you though that this won’t be like any business book or memoir you’ve ever read. I’m not going to hold things back and I’m going to show you some very human things. Being human is messy and not tidy at all, so fair warning, some of these stories I’m going to tell are dark. But I’m here writing this, so obviously there was a light at the end of the tunnel.

I’m excited to continue my journey with you.


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From being homeless to becoming a VC. My story.


Investor, friend, person, explorer and now author.