taylor desseynvp of community

don’t be afraid to go for the ask #techcareer #careeradvice #careergrowth

2 Jun 2025 · 0 min

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0:25

Taylor Desseyn shares how they casually DM'd a podcast founder who raised a $40 billion Series B and got them on the show. The lesson: ask for what you want. Most people won't, so you have an edge if you do.

I go for that. I just had a, I had a podcaster founder of a, of a startup in LA who raised $40 billion Series B round. I was like, there's no way I can get him. My wife listens to the podcast. I texted my wife and said, guess who's coming on my podcast? She goes, no way. I said, yes. Because you know why? I just slid into his DMs. I go, hey man, listen to your podcast. Love it. Do you want to come on my podcast? He goes, absolutely. You'll be amazed at the people who actually say yes.

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