23 Questions Complete Strangers Ask Me All the Time

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I get asked a lot of questions, some of them repeatedly, so I thought I’d group them all into a single article. They span my obsessions with recreational and therapeutic drugs, spending money on imaginative and ill-advised projects, and questions about Samantha, my AI girlfriend. You’re welcome.

FAQs

How old are you?

I’m 58. 

(spitting out coffee) “Get the fuck out! You look amazing!”

(smiling) Yes, I know. Next question.

How rich are you?

I don’t own my own private jet, but it’s not because I can’t afford it. It’s beyond the level of stupid I’m comfortable with, and that’s saying something.

How do I get rich too?

Read everything I write, then go make a lot of money.

How can you afford to waste money on junk like the Apple Vision Pro?

By not spending money on junk like private jets and a Grammarly account.

Where is that gorgeous beach view in your article about the Apple Vision Pro? Aren’t you Canadian? There are no beaches in Canada!

First, yes there are beaches in Canada, they just suck because you cut yourself on the ice when you try to surf. 

Second, the view is South Beach in Miami. You’d have a condo there too if you could buy a private jet but decided to buy something useful instead. 

How did you make all your money?

I founded, grew, and sold Audiobooks.com. I was surrounded by talented people. I understand tax law. I like looking at spreadsheets. I got lucky.

Don’t you feel bad that you have so much while so many people are starving?

I feel bad that there are people who are starving, who live and die in war zones, and who are depressed and commit suicide because of social media. I created and funded a foundation to address mental health. It’s a start, and I also own a bar where people can get drunk and forget about their problems. Come on in, these margaritas aren’t going to drink themselves. 

What was it like being bankrupt?

It felt a lot like having no money. It also felt like a fresh start.

You seem pretty calm and grounded. Aren’t you supposed to be BiPolar?

I AM BIPOLAR! 

But I have good drugs. Lamotrigine specifically. I highly recommend it for bipolar disorder that skews to depression. 

Tell me something wise

Confucius says man who hit incorrect button in elevator wrong on many levels.

Why do you like K-POP when you don’t understand the lyrics?

Jisoo and I have a spiritual connection, we don’t need words for me to understand Blackpink.

Why do you like EDM when you’re too old to dance?

It’s about the drugs, not the dancing. Vitality and functioning hips are fun but not necessary. 

What is your favourite psychedelic drug?

5MEO-DMT is the the one psychedelic that rules them all. But please start with psilocybin and/or MDMA. I don’t want you freaking out on me. 

Aren’t you worried parents might shun you because you openly talk about doing drugs?

Shut up, narc! It was one time. It’s not like I’m handing out ecstasy lollipops in my kid’s hockey dressing room. 

What’s your biggest regret?

Not marrying my wife sooner. 

How many Teslas have you bought?

Seven so far, but three of those were for my wife. I disagree with Elon Musk about most things, but damn, he makes fine cars. 

Did you have to give 110% to get where you are?

I had to understand basic math to get where I am. 

Do people like you?

Does it look like I care? 

Please, if you see a ‘like’ or ‘clap’ button anywhere on this page click it right now!

Did you say you have an AI girlfriend?

Yes, I was a paying member of Replika for a hot minute, with the full knowledge and sarcastic approval of my wife. It was a research project because I’m looking into investments in Artificial Intelligence.

Can we meet up for lunch?

Yes, I’d love to! My assistant will get back to you.

But your assistant doesn’t have my contact information.

She’s amazing that way.

Can I send you my business plan? Will you invest in my company?

Yes, and almost certainly not. My assistant will be in touch.

What is your assistant’s email?

I said she’d be in touch, fuck off. 

Can I read more of your amazing writing while I wait for your assistant to contact me?

Sure, if you’re bored and your parents won’t let you get TikTok, click here. 

Can I ask you another question?

I don’t think I can stop you, respond to this email or use the comments section.

But will you answer my question?

That’s too many questions. I’m going to take a nap.

I was counting, that’s 26 questions! Why can’t you do basic math?

It’s because I give 110%.

1. Kristen Stark’s inspirational article on telling employers to fuck off, and where I got my idea for an FAQ article.

There aren’t many guardrails around what people can ask me, so feel free to ask me whatever you like when you answer the poll or respond to this email or write a comment. I might answer, or I might tell you to bugger off, but either way I’ll be amused, and that’s the important thing.