If you are going to do this, I believe it's possible for you to have a productive conversation (as in, not a screaming match "debate") with Destiny about certain topics you are knowledgeable in - Internet infrastructure, payment processors, journalism, censorship, etc.
But to be honest, depending on how much he researched you, in his head you are probably the "angry, right-wing, transphobic owner of the doxing website Kiwi Farms", so it's likely he will steer the conversation towards doxing, harassment, transphobia and so on.
Destiny, despite his numerous flaws, doesn't usually try to go for gotchas unless the tone of the conversation turns hostile or you start confidently talking about shit about which he's better informed than you are.
I think the first few replies summarized what you should be aware of, but I'll highlight these points:
- Start the conversation in good faith, he's become less charitable to people that are hostile, hypocritical, inconsistent, or trying to use rhetorical debate-bro strategies against him, so doing any of those things is the easiest way to turn the conversation into a shitshow. He can talk to people with opposing views normally as long as the tone of the conversation is calm. All of the points below apply only if the conversation starts turning into a debate.
- He has a tendency to really dig down and nitpick some small part of something you said if it goes against the facts he knows, so if you can't explain whatever it is you're talking about to him from first principles, be ready that he might challenge you on it, and will spend 30 minutes deconstructing some extraneous detail you're wrong about.
- Be prepared that he's going to ask for sources about anything that contradicts his worldview, and they're going to have to be mainstream, "reputable" mainstream-adjacent, peer-reviewed studies or primary sources. He usually doesn't do this unless he prepares for a debate, but if you contradict something that's core to his worldview, he might bring up some sources of his own that "prove" he's right.
- Be prepared that he might push you to give specific answers to controversial questions that paint you as a bigot/racist/villain to 90% of his viewers if you answer them "wrong", so think about the most damaging questions he could ask you, and how you'll answer them if he does (honestly, if it gets to this point just stick to your principles, no point cucking if he's already in debate-bro mode and trying to do as much "optics damage" as he can).