Every startup should know about “the line” – its the threshold where you’ve “gone too far” – like kissing a girl in high school, or taking a joke too far. You don’t want to “cross the line” (ethically, brand-wise, etc…) as a startup, but not enough startups push hard enough. In the early stages, you need to know where the line is and get up close enough to build momentum”.

In November of 2011 I sent an email to Charlie Hoehn who is the mastermind behind Tim Ferris’ record breaking, New York Times best selling book launch of The 4-Hour Body. I had read the book earlier that year, and did a lot of research into Charlie and his tactics for doing a product launch of this magnitude. Charlie was at the time acting as Tim’s email gatekeeper (or so the rumours went), so I figured I’d hustle to get some more great authorship for our project StartupPlays.com.

I  cringe looking back at these emails but I think they act as a good reference point for “How not to send an email pitch”.

So charlie got back to me within a few hours with this one liner: “Thanks Mike, but I’ll have to pass on this. Charlie”. I sat on it for a bit and decided I’d send him another quick note asking for feedback on why the deal was not attractive to him and he sent met his:

Bad right? But great on Charlie for giving me feedback. I learned a lot from the exchange, and did the research afterwards (to little, to late). Turns out Charlie is not the kind of guy you want to send an email like this to. He’s very active in speaking out about cold email reach-outs, and has even shared his personal experience with reaching out to Tim. If I had approached the situation in a softer manner, tailoring my pitch to charlie’s temperament I would have stood a better chance.

I crossed the line while seeking early authorship on StartupPlays. Try not to repeat my mistake.