Read the full breakdown of this conversation: How to Sell When You Hate Selling — the key insights, my take from the coaching seat, and the full transcript.
You know you should be putting yourself out there. Pitching the idea, asking for the meeting, telling people what you’re working on. And you keep not doing it, because some part of you is waiting until it’s more polished, more proven, more ready.
Emily McSherry built her prototype for under a thousand dollars and sold it to five universities before it had a single feature that makes it impressive today. She started her career doing 500 cold calls a week, and she’ll tell you plainly that 80 percent of whether it works is what’s going on in your head before you pick up the phone.
This conversation is the practical version of ”stop waiting.” Not a pep talk, but the actual mechanics of how you ask.
In this episode:
- Why testing your assumptions is cheaper and faster than building the thing
- What ”good enough to sell” actually looks like, and why it’s much less finished than you think
- The difference between pitching at someone and asking them a question, told through a story about buying shoes
- Who to go to first when nobody knows who you are yet
- The two versions of you that can walk into the same conversation, and why only one of them gets a yes
About Emily:
Emily McSherry is the founder and CEO of Advize, a platform that helps students learn about careers by watching short video interviews with people actually doing the job. She grew up in a small town in rural Texas where she had no idea what was possible, did everything right in college, and still left feeling lost. She then spent close to a decade in recruitment in Los Angeles, training recruiters how to headhunt, which is where she figured out that the fastest way to learn about a career is to ask someone questions about it. Advize now holds over 12,000 video interviews.
Connect with Emily:
- LinkedIn: https://www.linkedin.com/in/msemilymcsherry/
- Advize: https://advizehub.com
Connect with Limor:
- Website: https://limorbergman.com
- Podcast: https://limorbergman.com/podcast/
- LinkedIn: https://www.linkedin.com/in/limorbergman/
- Substack: https://limorbergman.substack.com
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