Bojago Philip James's Blog

Courageous Conversations

I was at a seminar recently when I first heard the phrase "Courageous Conversations". The speaker used the words to explain the difficulty in facing up to and in having certain conversations. For example, it would be hard to say "I'm in the country illegally, and would like to apply for legal residency" or for someone to finally tell  their spouse "I had an affair five years ago."

I started this blog to...well, actually, I don't think I was ever really sure. I knew I'd learned a few things along the way, I knew that writing about ideas helps clarify them for me, and I wanted to make it easy for others to get the benefit of what little knowledge I'd manage to accumulate.

I've read a few posts recently that I've found really helpful and refreshing in their honesty:

- Ben Pieratt, Founder and CEO of Svpply, a NYC based social shopping site, wrote a post that Business Insider called the "Best Blog Post" written by an Entrepreneur that they'd read. Read his post here.

- Michael Lazerow, Founder and CEO of Buddy Media, another NYC based company, this one makes tools that make it easy for brands to manage their social media presence. Read his post here.

These posts are raw and open.

Ben's post, which starts out by saying "I truly have very little understanding of what I am doing", is about the abyss founders stare into every day, when they get up, walk to work, and then realize that they havent got a clue how to do what's in front of them. Every Founder faces this regularly, but most of us are too scared, or too caught up in the Great Man Theory, to ever admit any weakness.

Michael's post systematically breaks down his recent fund raising process, in which he calls out a lot of the bait and switch tactics VCs are famous for. Quote: "Many firms will throw awesome terms at you – a high valuation, more management options, founder-friendly preferences (I'll explain those later) – only to come back a month later and change them, or, better yet, pull out all together." This happens all the time, and its endlessly frustrating to entrepreneurs who have to crawl, hat in hand, to omnipotent VCs every year or so, and then spend months on a process (basically an elaborate game of chess) which is totally orthogonal to actually building the business. Problem is, as much as we all hate it, if you don't do it, the company will run out of money and die.

Both pieces are excellent examples of Courageous Conversations, and you should read them.

I'd like to have such conversations on this blog myself, but telling the world that you are scared, or in the case of the VC expose, biting the hand that feeds you, isn't easy.