Name: This Hedge-Fund Manager Has a Warning for Rookie Options Traders
Uploaded: 2026-05-01T15:50:00Z
Duration: 6 min 38 s
Description: He's lost millions making movies and built a fortune trading derivatives. But how much of it was really up to him? Skylar Capital founder Bill Perkins joins Gunjan Banerji for The WSJ Money Interview to break down where skill ends and luck begins.

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He's lost millions making movies and built a fortune trading derivatives. But how much of it was really up to him? Skylar Capital founder Bill Perkins joins Gunjan Banerji for The WSJ Money Interview to break down where skill ends and luck begins. Photo: David Wells

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He's lost millions making movies and built a fortune trading derivatives. But how much of it was really up to him? Skylar Capital founder Bill Perkins joins Gunjan Banerji for The WSJ Money Interview to break down where skill ends and luck begins.

This Hedge-Fund Manager Has a Warning for Rookie Options Traders

On each card, you're going to tell me if this thing is driven more by luck or skill. There's just one rule, nothing can be 50/50.

No 50/50, got it. Oh man, winning big on a out of the money call option. Let's just go with the luck and then I'm gonna put one skill for actually picking it.

I wanted to ask you this because of this boom in options trading.

Right.

Right? Over the past few years, and you are a big fan of taking on leverage.

Right.

Taking on big risks. And there are all these traders out there who call themselves degen traders.

Right.

They say they wanna take big risks, but I think there's a difference between taking smart calculated risks and YOLOing your money, right?

Yeah, at the end of the day, you wanna beat the house, right? Like Vegas is built on 0.6% edge, right? So when you're trading options or buying options, you're basically saying, hey, this is an underdog to happen, but it's positive expected value. And so that's a skill, right? But any one particular event, that's just luck.

What do you think has led to this boom in risk taking in America? Sports betting, prediction markets, options trading,

People's desire to not be hourly workers. That cohort of people, they probably have always existed, but now the tools are there for them to do it. And then now you have like Robinhood and E-Trade and all these platforms that are allowing people to do this.

But many options traders, rookie options traders do not make money.

You know, it is non-trivial to beat the market.

Like you, you are a professional derivatives trader. What is your message to all of these rookie options traders, prediction markets traders, sports betters?

You have to do a lot of homework and you need to be stoic about it. You need to be non-emotional about it. You're a salmon swimming upstream and most of us die, but some of us actually get to spawn. And so I don't fault them for trying to swim upstream. This is what they want to do, but a lot of us are just gonna die and not get to spawn.

Let's do the next one.

I'm gonna pick that one.

Okay.

That one feels lucky. A perfect vacation.

You are the pro at this.

I'm a pro about this. And this is a lot, a lot of skill. I'm gonna throw all these over here on skill and I might get one for the weather.

Okay.

And one for extraneous events that can happen and go wrong or go right for luck, right?

What's your number one travel tip?

Always take the bike tour. I've gone on fancy yacht trips and blah, blah, blah, but I've gotten so much fulfillment out of, hey, we're gonna meet this guy. You got E-bikes and you're gonna tour this area on a bike and go through the city. You get tons of coverage at an outdoor environment, a little bit of exercise if you take off the E. So always take the bike tour.

How much does a luxury vacation cost on average?

It depends on whose luxury.

Your luxury.

My luxury vacations are a function of how much money I have at the time. I mean, I've had luxury vacations where it's like, oh, we spent a million dollars this summer. I have it, and it's like, we spent 20K and I've been on one when you don't spend anything. You know what I mean? Like we worked our way through that summer, right? And so it really depends. What you really wanna be doing is designing it correctly for your wealth level to get the most out of it.

Yeah.

Not just considering that time period, but the entire arc of your life. All right, producing an Oscar winning film. Wow, I'm gonna go more luck than skill. I've made a lot of bad movies and I made maybe some good ones or cult classics or whatever, but you're making a piece of art and it can be great, but the taste of the Academy may change. Your film may hit the zeitgeist of the time and kind of hitting that cultural chord at the right time is a lot of luck. The scale part is, is like, it takes a lot of work and a lot of skill to put a good narrative out.

You were a trader for years. You decided to get into movie production.

Yeah.

How do you decide when you've been successful in one field, how much time and money to allocate to kind of a side project?

Well, I kind of kind of did it willy-nilly, like, oh, I can afford to lose that because I realized.

What was that number?

At the time, I was like, oh, I can lose a couple million bucks. And then it got was like, oh, I can lose 8 million bucks.

And you accepted that going into it?

Yeah, I accepted that.

Okay.

And I tell my friends who like, because of my experience, they're like, well, what is it? I wanna invest in this movie. I said, listen, unless you wanna go to the parties, make a piece of art that hasn't been done, or be a patron of the arts, that's your return. It's not the money. Even the best movie investment is your worst investment amongst all the other types of investment you do.

I wanna end with this one, I'm gonna cheat.

Throwing a great party.

This is the most excited I've seen you in the entire interview, by the way.

Yeah, I'm so excited, 'cause I love, I love throwing a party. And I tell my friends, I don't throw bad parties. Right, Baxter? First it's the theme. It's designing how people get around.

Okay.

Eat food, et cetera.

What do you mean how they get around?

How do they go to the bathroom? Where do they eat? Do they have water, et cetera? Anytime you have a friction point like that, it takes away from the user's experience.

Okay.

Right? Who do you invite, who do they talk to? Who are they gonna interact with? That curating a vibe, skill, skill, skill, skill, skill. Who you are as a host, how you show up.

Yeah.

How you get into the mental framework to get everybody on the vibe. That's a skill, not that much luck.

I have two final money questions for you. What is your worry-free spending number where if an item or an experience or something is below this number, you will not think twice about purchasing it?

A thousand. Not even, like, not even like unconsciously, but, you know, each one has its category of that trade. It's like, hey, it's this unique one of a kind trip. We're going to like, I don't know, Katmandu, and you get to go do this, whatever, whatever. That might be like 20,000. Like it's a no brainer, gotta go. And I'm not gonna like be on my deathbed, like, I have 20 grand, I should have went to Katmandu.

What do you want that you don't have right now?

A yacht. If yachts didn't exist, I don't know if I would be working. There was a time when we were trading and we were making all this money, and I was like, we're gonna buy the yacht. We're gonna buy the yacht. I was gonna chop a yacht with a friend and I think my share was like 25 million and their share was like 25 million, 25 to 30 million. But that's not what gets you, it's the two to $5 million in maintenance a year. So it's not the CapEx, it's the OpEx. Right? So really you're like, I need, if I'm gonna buy a yacht and I'm probably gonna use it over the next 10 years, you're talking about $75 million. No yacht for me, unfortunately.

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