The young man earlier said the entertainer introduced him to the businessman.
While staying in the businessman's home in 2016, the second complainant alleges he was indecently assaulted by the prominent New Zealander.
A few months later the entertainer began sending emails and Facebook messages to the young man and wanted to meet and discuss future work opportunities.
"I had a lot of respect for [the entertainer] and I still wanted to keep a nice connection with him," the young man told the court.
But, he added, he also "felt strange about it".
"The way he wanted to get me to meet with him felt very forced."
"From my incident with [the businessman] that previous year it had kinda broken a lot of trust for me and my walls came up," he said.
The second complainant said he was unsure of the entertainer's motives, especially because he had introduced him to the businessman.
The recorded conversation between the entertainer and the young man begins with the complainant talking about suing for psychological damages.
The entertainer, however, told the young man he couldn't sue in New Zealand but there were other ways to resolve matters.
"At least I can get in there and do the [entertainer's] fixing thing," the defendant said.
"Over to you, I'm gonna f*ck your life up bro, I can love as much as, and I will still love you no matter what happens ..."
The entertainer then encouraged the young man to talk to a well-known Auckland lawyer who could draft, what the second complainant believed, was a "contract".
"If you are going to do it, do it soon though," the entertainer said.
"Do what soon?" the young man replied.
"Talk to [the lawyer]," the entertainer said.
"I just think that sometimes the system is so against you, it's just so against you, but this way you could make the whole thing, if you wanted, disappear."
The entertainer continued: "Look, the best thing of it all is that you are very clever, by doing this, if we get it done, I can go, and I can get more and then you're out of the picture ... I think though, blackmail and things, could come out, but it's about your career ... Right, your career, not about money for damages, about money to empower you, to be this great thing.
"You're a very strong young man, that's what I like about you – there are some people that just have too much crush ... they can crush, people out there who can crush people."
As the conversation continued, the entertainer began asking more questions.
"But if you made a, what do you call it, a report or whatever, making [a] written thing, [the lawyer] can help you with that, terminology I'm sure."
The young man replied: "A report ... what do you mean?"
The entertainer said: "Well, you've made an accusation haven't you? Well, if you want to withdraw it, that's her job, she'll go with you, like all the others, what's your gut feeling?"
The young man wasn't sure, however, and compared the talks to a chess game.
"But you've won, it's no chess game, I'm in the middle here now," the entertainer said.
The second complainant replied: "Well, I may have won, but maybe I don't think I know I've won."
The entertainer quipped: "Oh no, you've won, you've only won, the only thing to look at is you've won, yip, you've won."
But the young man said: "The money's not an issue for me, it's more about, abuse of power ..."
The entertainer, however, continued and described his "thing" was to "dissolve it, get rid of it".
"Let's get you started on this career and let me ascertain some funds from [the businessman] at some point, which won't be hard, I can assure you of that, that's why [we] get rid of yours and I shall do the rest," he said laughing.
"You'd be surprised what money can do to buy people who you might know, you know what I mean? I know they can get nasty, that's what I don't want to see, the most important thing is you.
"He has enough money to buy people to survive ... give [the lawyer] a ring this afternoon, I'll ring her first to say you might be ringing," the entertainer said.
The young man later told the court: "My heart just sank ... [the entertainer's] intention was just to get me to talk to [the lawyer] to retract my statement."
He later met with the lawyer, whose identity is suppressed, before he gave the recording and a photograph of a $15,000 bank cheque to Detective Anthony Darvill, the police officer investigating the businessman.
The young man told the court he believed the cheque was "hush money".
Later in the day he also began talking about what the Crown has termed the "Gold Coast plot".
It involved hiring a public relations expert and tens of thousands of dollars to "silence [the complainant]", Crown prosecutor Simon Foote has said.
The complainant - who was living in Queensland - spent an afternoon of shopping and was wined and dined on the Gold Coast before again being asked to drop his claims against the prominent New Zealander, the Crown alleges.
However, the young man also secretly recorded a conversation there.
The two other people involved in the "Gold Coast plot" in May 2017 will later give evidence for the Crown but have already been given immunity from prosecution.
All three defendants had their interim name suppression revoked earlier this week by Judge Russell Collins after a successful legal challenge by the Herald and Stuff. But their names will remain secret after lawyers for the accused indicated an appeal to the High Court.
The jury trial, which is set for four weeks, continues.
