I’m confident and capable in customer meetings, but not conferences. In bars, but not clubs. In cafes, but not markets.
Expertise, and thus confidence, develops in silos.
The most shy person you’ve ever met can explode into life and become the king of the room when the topic of conversation shifts toward his area of expertise.
I stopped hating sales when I had talked to enough customers to deeply understand the market I was working in.
Customers suddenly began to love taking meetings with me (and I stopped feeling like a fraud) because I could reliably leave them with helpful insights, regardless of whether or not they bought our stuff.
Those nightmarish early meetings were the price of developing expertise for an unfamiliar process (sales) in unfamiliar industry (advertising).
While we still had zero customers, we hired a “sales guy” to help do “sales stuff”. We chose him because he was the most sociable and outgoing person we knew. That’s a helpful raw ingredient, but it was useless without the specific industry expertise and a solid understanding of how big sales work.
1. There are no magic-bullet hires in the early days of a startup, because the founders’ domain expertise trumps any generic skill that an outside candidate would bring to the table. That’s good news, because you can do it all yourself, and bad news, because you should do it all yourself.
2. Your broad personality traits do not prevent you from becoming extremely good at specific key tasks, even if they oppose your nature.
Getting comfortable with sales was truly, deeply painful for me. It was almost certainly the worst year of my life, which I endured only because the alternative was to fire my friends and default on my investors’ trust.
But importantly, I didn’t need to change my nature to become an “outgoing” person. I just needed to gain enough experience in that specific arena to shift from…
“Please let them say ‘yes’ quickly so I can leave.”
“I wonder what their problems are? I bet we can help.”
 That ultimately happened anyway, but for a more legitimate set of reasons than simply fearing meetings.
 People think I’m outgoing, which is because I’ve shifted my entire social and work life into the few arenas at which I happen to have accumulated expertise. Take me out of my primary context and I’m hopeless.