To chat with Yancey Strickler is to undergo a sustained exercise in envy control. Less then a decade ago, 35-year-old Strickler was a music journalist, scratching out a living by reviewing indie bands for Pitchfork and the Village Voice. Now he's the boss of Kickstarter – the crowdfunding site that has helped to get everything from boundary-pushing technology to Oscar-nominated movies off the ground. His site has raised over a billion dollars in the last five years, of which Kickstarter took a 5% commission. Strickler describes it as a public trust; last year Kickstarter funded more artists in the US than the National Endowment for the Arts, a federal body set up to support artists.

Anyway, I'm a current journalist turned nothing at all. Perhaps he's on to something. Perhaps journalism definitely is dead and it's time to jump ship. If that's the case, this is the time for me to follow his lead. Not by starting a wildly successful startup of my own – that sounds like quite a lot of a faff – but by launching a Kickstarter project. And so, offered an interview with Strickler, I did what anyone with some nous and self-respect would do: I pitched him my ideas.

SH: Idea one: a T-shirt with a load of monkey puns on it.
YS: That's pretty strong. Do you have any pun examples?

I've got three. First: Mo monkey, mo problems.
Yeah! Ha ha!

Second: Goodyear Chimp.
Yeah …

I pretty much ran out after two. The third one is Landscape Marmoset, but I'm not sure that works.
I don't understand.

It's a play on Landscape Architect. It probably needs more work.
Right. I don't know about that last one. Maybe, like, some landscape architects would be super into that. You could hit those landscape architect mailing lists really hard. You know, I did a T-shirt project. It was based on Fugazi. They refused to sell T-shirts, so people made their own with "This is not a Fugazi shirt" on them, because Fugazi rejected all merchandise. So my project was called "This is not a Kickstarter shirt", and the idea was that the only thing on the shirt would be the stats from the project. There's one person in London who I saw in the street with one once. But T-shirts are a good idea.

Idea two: artisan food is big on Kickstarter. How about a food truck where all the meat is guaranteed to come from an animal that's been brought up with a human name?
So you could meet the pig whose random parts you're eating?

Yeah. You'd hand over a hotdog and say: "This was Kevin. His life was short but he wanted for nothing."
Right. Right. I think you could probably do well for that. I wonder if … [glances over at our photographer, who looks appalled]. You look terrified. But we might have reached peak food truck. We might be post-food truck now. I don't know. A food bicycle, maybe? Perhaps a traditional restaurant? I just backed a burger joint in Shoreditch. I backed that for about 10 quid or something, so I'm owed a burger and fries. Certainly your idea seems very farm-to-table.

Idea three: just a load of crap that doubles as a bottle opener.
Yes! Yeah! You know, there's something interesting in this. One of the strangest, most prevalent things on Kickstarter are slim wallets. We have lot of those. A lot of wallet projects. And we started to look into it, and found that a wallet is actually a training wheel for a product designer. It's one of the easiest things to manufacture and produce. It teaches you the supply chain and how to produce something. You have to deal with manufacturers, but the product itself is very simple. We've seen a few people start with a slim wallet and then go on to something else because they've got a sense of how it worked. So I have a sense that a bottle opener might be in a similar vein. It might be a seemingly cheap tchotchke sort of thing, but it might also be an educational tool for someone to learn how to make something. My own wallet is a Kickstarter wallet, in fact.

What percentage of everything you own came from a Kickstarter project?
Quite a lot. It'd be funny to try to live for a year on only Kickstarter products. It'd be like "I need someone to launch a project for water today, I'm kinda thirsty." We'd need Kickstarter plumbing, a Kickstarter house …

What about a tracksuit that closely resembles formalwear?
That's very shrewd. Generally, anything to conceal human laziness will be pretty strong. Sweatbands, sweatpants, sweatshirts; I think you could do pretty well. There's the 10-year hoodie, which I think is our biggest fashion project, or close to it. A formal sweat? You know, Kanye's got his leather jogging pants, so you could be in a similar school, maybe.

Next: a song about me believing in my dreams, accompanied by a video of me dancing on a cloud.
I think you would get probably no backers, but you could easily launch that.

There are lots of music projects on Kickstarter, though.
Music does really well. Music has one of the highest success rates.

So what you're basically saying is that the only thing wrong with this idea is me as a person.
I don't know. It depends on what you want. How much money would you want to raise for it?

I dunno. Ten grand?
Ten grand to record one song? Yeah, I think this would be a no-go for ever. Strike that one out.

Finally, a version of Kickstarter that only charges 4% commission.
It only charges 4%? You know, you could do that. Certainly we get a lot of competition, with people doing the exact same thing as us.

And I could fund it through you?
Uh, soon you could. I think. I don't know. I'm not sure what my answer to this one is. It's currently prohibited. Not because it's direct competition, but because we don't fund software businesses. I think that's gonna change at some point. Things change, you know?

OK. So which of these ideas is the strongest?
I guess the T-shirts.

Great. So, in terms of rewards and incentives, what should I offer my loyal backers?
You should do offer the T-shirt for something like 15 or 20 bucks, something like that. I wouldn't offer too many colours. With my T-shirt project I made the mistake of offering eight different colours and it got complicated with the T-shirt vendors. Pick one or two colours and make your life much easier. Maybe I would consider offering a T-shirt for a higher amount, where you would add your picture to it, so you are the monkey – not you the creator, but the backer – that'd be a good gag gift for mum and dad.

I'm going to be rich!
Another thing I would do is … I don't know whether you saw the Planet Money T-shirt project from an National Public Radio journalist in New York? They made the T-shirt through Kickstarter, but used the project to tell the story of how the T-shirt was made. So they went to the factory in Malaysia. They went to New Zealand, I think, to see where the sheep was raised and see where the wool came from, they tracked the entire product from them raising the money on Kickstarter to the shirts arriving at people's doors. That actually ended up being really fascinating. For you, I would suggest documenting as much as possible how you did this.

A Planet Monkey T-shirt.
Well, maybe just document the 30 terrible designs you came up with before you found the one that was good. I think that stuff's always entertaining. Humanising it might be quite fun.

Finally, how I can promote my project?
A lot of tweeting. You're gonna want to make a video that's very strong and cross-post it on YouTube. Look for your audience. Maybe there are some monkey-related messageboards that you could be a part of. Is there a London zoo? Are there monkeys at London zoo? Maybe people outside London zoo are your core audience. You could just try to wear the first version of the T-shirt very proudly and hope that someone asks you how they can get one. Every day you should wear that shirt.

What if I committed a horrible crime while wearing the T-shirt?
Would that work?
In the monkey T-shirt! Yes! Get arrested in the monkey T-shirt!