I want you to hate me

Hello friend,

Travel Bulletin: I'm in Toronto at TIFF this week. Anything cool happening?

Here's what I'm thinking about…

I want you to hate me.

I want you to read my newsletters and seethe. To think, "God, he's just THE WORST," as you hate-scroll. Or mutter "fucking tool" when I say something obnoxious on a podcast, white-knuckling the steering wheel.

Not all of you. Just some. Maybe 2-3%—that's the sweet spot.

Ten years ago, this would have struck me as insane. I would have wanted the opposite. Then I read a Warren Buffett quote that became toxic when I took it too far, lived in a reputational cage for a decade, and finally found my way out via a book that felt like someone handing me the keys to my own cell…

Read the full essay →

A few weeks ago, I hosted my third annual Interesting People event.

I'm still buzzing. I recently described the feeling to a friend as a "low grade MDMA high that lasted for 3 days". Everyone gelled perfectly, we got lucky with the weather and logistics, and most importantly, we packed the room with 150 fascinating people from the worlds of science, comedy, business, and philanthropy.

It was easily our best one yet. I'll write more about it soon, but in the meantime, here's a few highlights:

• Dan Mangan making me cry like a baby (and delivering one of the best live performances I've ever seen - check out his new album, it's beautiful)

• Alex Forman and Nash Park ruthlessly roasting my friend Julien when he revealed he owns a Jurassic Park themed jeep

• Will Mannon opening for Hannibal Buress… in Mandarin

• Doing a sauna session with Sauna Royalty, Dr. Rhonda Patrick and Dr. Ashley Mason

• Matthew Dicks explaining the best way to punch someone (through their head)

• Learning to write Onion headlines with Scott Dikkers

  Trump Swears Mayan Temple on Epstein's Island Only Used for Human Sacrifice

  Trump Changes Name of 'Miss Teen USA' Pageant to 'Miss Definitely Legal Age USA'

• Jon Glaser reading letters that revealed that his dead dad was In Z.Z. Top (the book he wrote about it is hilarious and his new comedy album almost made me crash my car from laughing so hard)

• Me and my brother dropping to our knees to do a Wayne and Garth style "We're Not Worthy!" when we met Bill Oakley

I honestly can't believe how well it went. A huge thank you to my friends Monica Lim and Nick Gray who help me put it on every year.

Speaking of events, I'm hosting one for lonely conglomerateurs (yes, that's a word, and if you ever want to get punched in the face, introduce yourself as one).

There are tons of support groups for executives and CEOs, but none for folks who run holding companies. It's a unique role with a rare structure and set of challenges.

Frankly, it can be pretty isolating because there are so few people who can relate to our problems (of which there are many: perverse incentives, compensation negotiations, reporting complexities, etc).

In fact, I so rarely meet people who I can talk to about these problems with that I had to start my own event. It turns out, there are dozens of us!

I hosted the first Conglomerateurs meetup in May in Vancouver, and it was incredible. We assembled a collection representing hundreds of companies and many billions of dollars in revenue across the group. We spent 3 days diving into our collective problems in a super confidential format, and everyone really clicked.

Now, we're doing it again. In early January. It will be very intimate, with less than 30 people attending.

This one is in Maui at my absolute favorite resort, and we're giving everyone the option to bring their families along to enjoy the resort while we talk business, and I've got some incredible guest speakers coming.

We have a few spots open, so if you run an at-scale holding company ($25M+ in revenue, at least three businesses, serial acquirer) and you're looking for your tribe, you should apply.

Do you want people to like you?

The answer is very simple: ask questions.

I was recently on the East Coast for business and I had lunch with someone who, no joke, over the course of an almost two hour meal, went on a monologue about himself and asked me exactly zero questions.

At the end of the meal, as we were walking out of the restaurant, he remarked, "man, that was fun!"

It was. For him...

Read the full essay →

"I want to send you something I'm working on…"

Ugh. My friend Matteo asked to send me his mattress gadget. I didn't want it.

I knew it would end up rotting in my basement with all the other expensive health tech, next to my Theragun, red-light therapy panel, and infrared-sauna blanket.

I guarantee you've heard of Matteo's company: Eight Sleep...

Read the full essay →

I've been rediscovering The Beatles.

My love affair started the moment I hit play on Rubber Soul…

I was fourteen and I'd just gotten a Sony Discman. On the way out the door, I grabbed an interesting looking CD case with four shaggy-headed dudes on it from my parents' music collection and threw it into my backpack.

I pushed the shiny disc into the player, threw on my headphones, and listened to the album straight through as I gazed out the window on a sunny drive to a cabin we'd rented for the summer.

It instantly clicked. The perfect album, and one I've listened to hundreds of times since.

Over the past few days, I've been devouring John & Paul: A Love Story in Songs, Ian Leslie's wonderful new book about the relationship between John Lennon and Paul McCartney. If you're into The Beatles, or even just interested in how creativity happens, it's a great read. It's been the perfect way to revisit their epic catalog (195 songs) and discover the stories behind each track.

Today, I've been driving around blasting I'm Looking Through You, which, beneath the psychedelic riffs, captures McCartney's painful realization that his girlfriend had fundamentally changed: that the person he'd fallen for was no longer the same person sitting across from him. I'd been listening to this song for decades without even knowing what it was about.

Trust me on this one: if you like The Beatles, read this book.

More importantly, if you don't like The Beatles, then this needs to be rectified ASAP. Stop what you're doing and listen to Rubber Soul all the way through, otherwise we can't be friends.

Random Stuff:

• The new Naked Gun movie is absolutely hilarious. I think it's the first movie I've seen in theaters with my sons (6 and 8) where we all laughed our heads off together. Akiva Shaffer (The Lonely Island), the director, never fails to bust my guts. Trailer

• I enjoyed this conversation with my friend Lydia Chen on her podcast Escape 9 to 5. You can listen to it on Spotify.

• Messages are ruining my life. Hundreds a day and they're split across iMessage, WhatsApp, Signal, and Slack and having to jump between all those apps to keep the notifications at bay stresses the hell out of me.

  But not anymore, thanks to Beeper.

  It's like Superhuman for texts and combines all of these services into one insanely fast, keyboard-driven interface. So good.

• Nerdy Finance Question: I need a venture fund admin service to mark all our investments + manage day-to-day operations + track investor updates for my 150 or so personal venture investments + the Tiny Rolling Fund. Who's the best? Would love some recommendations.

• I'm hiring a full-time AI automation nerd to work with me to help me with personal automations + some workflows within my various businesses.

  You: eat, live, and breathe Lindy, Airtable, and the like. Have never seen a task you can't automate. Are insanely high paced and obsessed with AI.

  Email me examples (ideally in a Loom) of some of the cool automations you've built. FULL-TIME ONLY, with a three-month contract to start.

Victoria Stuff:

• A nice new restaurant opened in Oak Bay. It's called Liv Bistro. I've been for dinner a few times and been impressed. Check it out.

• Need a personal trainer? Talk to my trainer, Tameer. He's a competitive powerlifter, super down-to-earth (critical for a trainer), and he comes to your home (huge time saver). He has a few spots opening for new clients.

• If you like Vietnamese food, I'm hooked on Original Pho. There's two locations, one in Langford and one on Fort Street—both are great.

That's all for now…

-Andrew