"I failed miserably at this for two simple reasons: I hate rejection"<p>Rejection is tough on everyone. Good sales people do a few things to mitigate this that I've noticed and practiced. One thing is to think of it as a game to expect a certain amount of rejection as part of what you do in advance.<p>I mean if I told you right now to pick up the phone and call someone and pitch them and there was no outcome and I paid you $20 to do it you probably wouldn't have a fear of doing that. If I told you that I would pay you if they hang up on you $20 but $0 if they don't you probably would all the sudden not be afraid of the hangup, right? It's all a psychological game. Same thing with approaching a girl in a bar.<p>Second thing though is that some good sales people don't pick up on social cues as well as others. So they don't feel the rejection as much as sensitive people do. If you are cold calling the same micro expressions that might turn a sensitive person into jelly completely escapes many good salespeople. Same with just a voice. It takes time to get over this automatic reaction but it can be done with practice just like anything else. (Although you don't want to turn it off because the same skill is really good for negotiating.)
"Worse, I had to admit to my wife that I failed. I couldn’t even pay my half of the mortgage."<p>Three cheers to the significant others that are patient with entrepreneurs and willing to put up with us!
6 customers at $199 a month is almost $1200 per month. Sure, it's not a fortune, but I wonder why it wasn't enough for "leave it running, work on something else, cash the checks, see what happens" to at least be one of the options.
We'd been running EventVue for 3 years, were exhausted and at the end of our runway when Brad Feld (one of our investors) asked us one question: "Are you still having fun?" When we couldn't honestly answer "yes", his advice was "Then quit! Life's too short." We announced we were shutting down the company the next day and I've never felt more relieved.
"2 - Hire a good salesperson" - "I couldn’t afford #2 "<p>Why not partner with a good salesperson someone who isn't afraid to pick up the phone and make sales calls?
I remember hearing once (possible on Marco Arment's Build and Analyze) that million dollar ideas aren't created overnight. Companies like Rovio (creators of Angry Birds) had to suffer through tons of failed products before they struck gold. I think this article shows the value of perseverance and poses a very important question: when do you quit and try something new.
Excellent post Ryan. Working in enterprise software our sales guys here No a hell of a lot more than Yes.<p>When I hired the last two new guys, I said .2 is a great batting average in baseball. You'll never be close to that in enterprise software. It's a numbers game. Heard those types of speaches all the time in grad school regarding startups and sales.