How casual can early sales communications and product demos be when selling to traditional corporate clients?

2026-06-25 · Lounge

Hi,

Do not go out and buy a suit (or more accurately in your case, put on the one you already own). If you try to fake being some hyper-formal corporate guy, they are going to smell the inauthenticity a mile away. People want to do business with real people, and being authentic is your biggest asset.

But while you can certainly keep the casual tone, make sure that casual dress doesn't mean casual content. You will still need to keep your demos tight, professional, and focused on their problems. Think about how good you are explaining the rules of games to people. That's exactly the process you're going to use for explaining how a product is going to solve someone's problems for them. Your ease, competence and ability to make genuine connection will enable you to be amazing at this. It takes preparation and practice.

But there is a trap here you need to watch out for. Don't confuse "being yourself" with choosing your own convenience.

I had a post get a huge amount of traction recently; the one where I complained about voice-memos. A lot of founders send them because speaking feels faster than typing. But you have to ask: "Am I making this easy for them, or just easy for me?"

If an East Coast corporate client has to sit through a rambling, informal video to get to the point, you've made your convenience their problem.

Public Hand Raises only. Questions anonymized; answers are Marc Randolph's mentorship responses with names redacted.