We just calling everything that’s automated AI-powered now

Always remember how badly you once wanted what you already have right now

At any point in life, you can just decide to live a different life It’s one of the most powerful (and scariest) secrets around. Everything is a concept in your head

Once you make 100 bands a month you realize how free-flowing and loose capital systems are The idea that a good job is like 200K a year and people bust their ass, really messes with you

Taken 30 mins apart

5D chess move by @sama - He said none of their best ppl take the offer. If you take it, seen as not top talent anyway - Zuck might not even be offering 100M but now this becomes the market price - Everyone else at Meta feels envious

Jay Z works at Square, Dr Dre works at Apple, Nas is one of the best VCs in the world

How to sabotage a workplace by the CIA sounds similar to a lot of company culture manuals today

What are the best things you’ve bought under $500 that you really enjoy or have dramatically improved your life?

Canada, where we only retain ppl that want to make less than 200K for life Where you should never dream big

Airbnb services fees competing against eth gas fees

Alpha leak: Airbnb adds services like personal chefs, trainers, security, nannies, etc I tried to run Airbnb through same internal software I’ve built to monitor Robinhood, Hims, and a few others. Let’s see.

Gotta admit the way Zuck just copies what works and drops a billion users on it is super gangster

Unfortunately, no crying in the casino

Rarely, but sometimes, in life and business, all you have to do is sit and wait for your opponents to make unforced errors

The next FAANG will be SSSSS for Square, Shopify, Stripe, Spotify, SpaceX

When I was 23 i got a job consulting at McKinsey, felt so cool because I got to travel all the time, live out of hotels, etc A decade later, that sounds like a nightmare. Legit hate traveling for work and try to fly back same day so I can sleep in my bed

Venn diagram of people focused on winning and people that want to have coffee chats and go to networking events

I love PG and what he stands for. I met @paulg once at YC and got to attend a YC event in 2012 and was inspired for life That said, the analogy that rich kids basically get more shots on goal is 100% accurate. Everyone in the replies saying it’s cope has never been systematically poor. Maybe they were a broke student but imagine knowing you have to pay for your parents and siblings when you get your first job. You basically become the first person in your family to ever make 100K+/yr. Everyone is depending on you to eat, the risk you have to take to start a startup is beyond any reasonable risk humans take at that age. Most of the ppl on Twitter don’t know what the bottom looks like, I started from the bottom. I hate excuses. Growing up seeing other kids able to spend or save their whole salary was surreal to me. I been through it and made it. It’s very real.

Let me share a little known part of my life: In my early 20s, I briefly spent some time working at McKinsey. Felt extremely high status, they paid me 250K/yr, and had to travel all the time I lived in the Ritz by Central Park Mon-Fri, fly back to Toronto for the weekends, worked at 53rd and Lexington. Business class flights across the world, per diems, travel concierge, etc, etc. Bruh, let me tell you it was the most miserable experience ever. First of all the work was not interesting. The novelty of the travel and money wore off after a few weeks. The worst was the people. The people themselves were nice but so high ego. Some of them had families they barely saw. I'm not telling anyone to not do it, in fact you should try it. Just saying it's rarely as nice as it seems, so be careful before you romanticize something that's not real

I want to share the story behind why I joined Opendoor (It might be a little long. I'm not media trained, so this will be straight from the dome and I'm just going to hit send at the end) The last 4 years I was basically retired. I started a small fund and was having a great time investing. I live a pretty modest life so I never really planned to work again. Over the years so many companies reached out. I met with the execs of large public companies, celebrities and athletes that were starting software companies, and so on. Some I really considered, but always ended up say no. It wasn't about the money, they offered insane amounts but I just liked my simple life. I'd drop my kid at school, bike to the studio space I share with a bunch of my friends, spend the day reading, investing, coding, grab a coffee, and head home. I've always been fascinated by asymmetric risks. Usually I do it from the sidelines like any other retail investor. I've also seen how often consensus is flat out wrong. I was at Shopify as a lowly PM when this short seller report came out in 2017 calling the business a pyramid scheme. It was crazy to reconcile what I was seeing in front my eyes, a company operating at maximum excellence, hypergrowth, etc and everyone else repeating whatever they heard. Turns out they were wrong. I saw this a few times over. Before Shopify, while I was building my first startup, everyone thought we were idiots. These were credible people with serious sounding job titles at hot tech companies. We ended up getting acquired by HubSpot. Turns out they were wrong. When Carvana got decimated, and even today, people love the narrative that it's a fraud. Turns out it's a great business that people just don't understand. I was deeply invested in the business and knew the business was turning around while at the same time the media was publishing fear. Turns out they were wrong. After Robinhood got decimated, same thing, people were unable to consider that the business can change and evolve. I posted an experiment and my P&L on twitter and people DMed me calling me an idiot, over indexed, going to 0, and so on. Not just the anon accounts but real people I know and respect. Turns out they were all wrong. I guess I'm not just fascinated by asymmetric risk but I'm addicted to situations where I think everyone else is wrong. At Opendoor, it's incredible man, I get to actually do the work, not just watch from the sidelines. I get to work with people that are at the top of their craft and fully committed to the mission. So, when the opportunity came up. It was an instant decision. I "un-retired" and am all-in on the biggest bet of my life. We'll see how it works out but you already know where I placed my chips. At the end of the day, none of this shit matters. We just have to ball out, have fun, and pursue excellence. I'm not doing this for the money, I already have more than I can spend in my lifetime. I'm doing this for the love of the game and most importantly, I'm doing this because I think everyone else is wrong.

1. Being an exec 2. Being a founder 3. Raising money 4. Traveling for work

Product Manager when someone asks a technical question

Elon couldve bought Lyft instead of Twitter and have an existing rideshare marketplace to lease model 3s to the drivers (and introduce robotaxis over time)

Early in your career, it’s more important who you directly work for than where you work

New workspace

What is this style of design called where it feels like tech and software are blending in with nature

Everything has 3 costs: 1. Upfront cost 2. Opportunity cost 3. Maintenance cost This applies for material and non-material objects. We tend to focus in 1, sometimes consider 2, and rarely think about 3.

A startup I invested in long ago shut down recently I shared this note with them. Figured I’d share publicly since it applies to anyone that tries something and fails.

There are 3 types of angel investors: 1. Sends wire, never speaks again voluntarily 2. Replies "awesome!" to every monthly update 3. Emails you with "have you seen this?" and link to every competitor that raises a single dollar

Canada might be the only country on Earth that has both an immigration problem and a brain drain problem

The problem I have with most new VCs man, is that they have built and accomplished nothing. They’re literally unqualified to give you feedback on your startup. I know a lot of them personally too because I invested in their past failed startup where they shipped nothing for a few years then failed up to some random firm

If my home was burning and I had the resources to save it, no question Anyone saying otherwise is brainwashed or braindead

Friend just signed for a 1.5M mortgage, pays 75K a year in just interest (5% APR) So he's paying his annual salary (post-tax) in interest. And it's higher than median household income in Toronto

My first job ever in investing is running this fund Plz send positive vibes betakit.com/roach-capital-cl…

If you grew up poor and eventually "made it", there are still 2 aspects that don't really get resolved 1. People will depend on you so it's harder to compound 2. The people closest to you still have a scarcity mindset so every risk you take is seen as too risky

Today at @Opendoor we’re introducing two new features: 1. A 100-Day Home Warranty covering major systems and appliances. This is available on every Opendoor home right now, nationwide. 2. The 7-Day Home Test Drive. Move in up to 7 days early, experience the space, try out the lifestyle. If you don’t love it, leave it. Live in Dallas today, nationwide soon.

Gm, Sep 17, 2025, time to go all in Will share more as we start building. I hate to lose so I’m going to give this every ounce of my energy and focus. In my mind, there are only two possible outcomes: we win or I die. Time to get to work with @nejatian and @shrisha.

2.5M house in Toronto vs LA...

In 2019, after I left Shopify I started focusing on investing my own portfolio I did research on Snapchat, saw they had like 50% of 18-25yo in the US as DAUs. Ended up buying a large amount. Then I wrote a pitch on what I’d do if I was a PM at Snapchat, cold emailed, told me if I was around LA to stop by. Flew to LA, chatted/interviewed and got an offer. Negotiated for max stock, no cliff, monthly vest, minimal base salary. Was just before the pandemic, when I flew to LA was the only person on the plane wearing a mask. Joined at the pandemic bottom, stock went up 5x from there

Today is Day 7 of working on Opendoor The most important realization so far: I have higher conviction today in this mission than ever before

The world’s tiniest family office, Roach Capital, has acquired $500K worth of $OPEN today Mission aligned, love this team, let’s get back to work 🫡

The average Canadian midwit: - Still taking covid vaccines - Healthcare is excellent here - Earning a median salary of $42K a year (30K USD) - Kids are being indoctrinated at school - Competing against 2K ppl for a entry level job - Vacation to a 3.5 star resort once a year

I met a guy, raised 1.5M on pre-idea (pre pre seed), now raising again at 3x cap with the idea ???

My start at Opendoor might be the funniest and my favorite one yet

Domino’s pizza tracker was before it’s time. The neural nets of pizza tech

It’s a strange time to share personal news. In a turn of events, I am now employed. I’m joining @Snap to help build commerce into the ecosystem. Will still continue to make angel investments and work on experiments.

Marissa Mayer is the perfect example of a corporate success that got rich af but now conflating that with ability to build startups from scratch Success in a big company is different than success building from scratch, almost no overlap in skills

HBO's silicon valley wasn't a parody, just ahead of it's time

I’ve worked at startups that I started and sold, Shopify, Snapchat, and have seen many companies intimately Right now at Opendoor is the most exciting work of my career, and hopefully it will be the most impactful to everyone

Unreal sunset, unedited pics (except whatever the iphone does automatically)

The ideal startup team today: 1 “CEO” - PM, partnerships, marketing, support, data, growth, etc 1 Designer - Design, front-end 1-2 Engineers For anything else hire a contractor or just learn it You can build almost anything with this team composition. 3-4 people is all you need. Anything else is fluff.

A funny observation from founders I work with: Investors investing $10K do more diligence than investors investing $1M

This morning I got mugged in Toronto I was supposed to get a payment of 42.5K and after the CRA robbed me I ended up with 17K This is the only retention issue for talent in Canada, nothing else comes close

Man. Invested in a company in 2021. $1M ARR app. Founder raises some money then just completely loses it. Loses the plot Starts clout chasing, starts executive coaching for money (with no real experience), no updates, company goes to 0. Drains every last dollar and finally shuts down with absolutely nothing built or attempted over the last 4 years. Grift season

If you joined Shopify in 2016 with a $100K annual grant, it would be worth $20M today As a bonus, it would’ve been liquid the whole time and you would have outperformed their VCs that sold at IPO

I've been buying Ethereum daily over the last few weeks Bank fraud dept called me and asked where I keep transferring money I told them "the future"

I wish there was a mens wellness place that had all of these things for a membership: - bloodwork, VO2 Max - dexa scans - nutritionists, athletic trainers - massage - recovery like normatec, ice baths, cupping, etc - TRT, IV drips, and other supplements Does this exist?

Wrapping up the week here and flying back to Toronto Lots of progress. Lots of work to do. Listening to customer calls on the plane for the next 5 hours. We need to be relentless and build an exceptional experience for people to buy and sell their homes. It will take time but we will make consistent forward progress.

We don’t want you to buy a house, we want you to love a home Soon you’ll wonder why it was ever different

Magical products are a result of someone putting in tremendous amounts of work They're outworking us so much that we can't believe it, so we conclude it as magic Work harder and don't let anyone outwork you. Make magical things.

Cool yea here’s my come up story: - Math at Waterloo, transferred to CS at University of Toronto - Started a software co, sold to HubSpot - Started a payments co, soft landing - Joined Shopify as a PM. Worked on mobile, mobile sdk, POS, POS apps, POS hardware - Joined Snapchat. Worked on AR commerce, payments, lenses - Was angel investing the whole time. Started a venture fund. Tiger Global and myself are the largest LPs. - VC fund doing decent. Investor in Replit, Railway, Carry, Wander, and many others. - Got interested in public markets. Learned everything I could. Started making concentrated bets. Biggest wins have been Tesla, Meta, Carvana, Robinhood. A bunch of side quests along the way. Lmk if any questions about this

Tomorrow we will take a small step towards changing the way people think about buying homes forever It won’t happen overnight but this is the beginning. We’ll keep going piece by piece until the job is finished.

I'm planning to create a series of short videos on product management. They'll be 5-7 mins, each covering a single topic with an example and some visual models. It'll be free on YouTube. What else should I add to this outline. Here's what I have so far:

For all the people complaining that CS grads should stay, put your money where your mouth is and start paying up Min 200K CAD TC for new grads, 500K-1M TC for experienced ppl in 90th percentile

Things you should not worry about early in your career: - Title - Picking job based on max comp - Picking job based on status - Picking job because the company feels “safe” Things you should worry about: - Who you will work with closely - Will you learn - Will you have max impact

If Coinbase can rescind offers, would they be okay if candidate accepted an offer and backed out at the last min

Good early stage founders look unsuccessful for a long time Bad early stage founders look successful before doing the work

Your life should be a series of increasingly larger bets You make a bet, then it plays out and once you capture most or all of the value, it’s time to go back to thinking about the next bet Larger could be size or risk or discomfort, bet just means adventure to keep growing

I’ve been at Opendoor for 11.5 days now. Want to share some quick thoughts: 1. Great things take time and often won’t look obvious from the outside 2. Every thing we (as humans) build is a function of speed and quality. Sometimes one is needed more than the other. This isn’t my first rodeo, I’m not trying to look good at my job, I’m here only to win.

A mini thread on the Mimetic Theory, Peter Thiel, and taking asymmetric risks. First, let's understand the Mimetic Theory. It's a fancy way of saying we want things because other people want them. Here's how it applies to the way we make decisions:

90% of all PM jobs in tech are fake Take full ownership of a product and make good decisions and you'll be in the top 10% All these checklists of tasks that we're taught are tactics, not strategy Source: I was a PM at Shopify, Snapchat, etc.

This is really cool analysis. My main takeaway from this is that a single guy, Jaan Tallinn, led the Series A of Anthropic Had to look him up. He was the founder of Kazaa, Skype, aped into Bitcoin, then led the Series A of Deepmind and Anthropic. Also apparently still lives in his hometown in Estonia... Insane arc

There are only 2 types of people: 1. People trying stuff and learning 2. People making fun of and laughing at people trying stuff Guess who wins

Apparently they also use the heloc to buy a car... Fam this is the definition of over leveraged

Death by Venture Capital

I think the biggest flex ever is making it big and you still having a loving family, wife and kids love you If you have this, you have won. Nothing else needed, anything else will be an unforced error

Idea for a new venture fund: - Invest in solo founders or tiny teams with proven ability - Fund creative people - Invest very early (ex. idea) - $200-500K - Annual dividends after a threshold Building software has changed completely in the last 6 months. We'll see more founders that can build a brand, software, a business, distribution, and run it all with a tiny team. We've already invested in a few of these at @RoachCap with @kerooke building August and @preshdkumar building The Wellness Company. One more not announced yet. If there is a Roach Fund II, this will be it

Dang, this was long. Congrats to anyone that actually read it through

A software engineer in the 90th percentile in Canada makes 2x less than their counterpart in the US and 3x less than SF The median SWE in Canada earns less than UK or Australia

Went to bed last night at 2am, woke up at 7a, drop kid at school, flight, straight to meetings, finally at the hotel at 11p Excited for this next bet and have deeper conviction than ever before after today, so the day was well spent, though very long

The team we build is the company we build…

Honestly, if you're a grifter Canada is an excellent place to live

This guy founded and sold 4 companies, is mega caked, and still grinding out here 630pm on a Thurs

What are modern day scams that we’re all acclimated to? For example is there any real basis to preventative wisdom tooth removal

In my time so far, my biggest bets have been on companies that were highly underrated or even marked for the grave Shopify, Snapchat, Carvana, Robinhood. To me, each one was a canvas for learning, building, and reinventing Shortly, I’m going to make the biggest bet of my life, the masterpiece In this game, where risk is the only currency that matters, call me the Merchant of Death

When I broke my ankle, I had to wait 7 months to get an MRI in Canada Went to the US and got it same day, $200. Lost faith in this social public welfare health system for life

Another one: Speed is of the utmost importance If you’re 2x faster than your counterpart you can be wrong half the time and still be ahead. You’ll also have 2x the number of reps so your decision making will improve and be right more often

I’ve had lump sum windfalls from selling companies, stocks, etc but making 100K/month recurring was the most insane feeling Probably what it feels like to smoke crack. That’s why my account is labeled as an Addiction Treatment Center

No bonus points for going through unnecessary pain

You think Jeff Bezos would move to Bali and post pictures of his meals if he was launching Amazon today?

The most thoughtful people I know think in probabilities while everyone else is thinking in absolutes Every decision or outcome has a probability tied to it

One final small announcement before I sign off for the year: I wanted to grow @RoachCap so we raised a ~$5M fund for investing in early stage companies This is the first time I've brought on outside LPs and will be Roach Capital Fund I.

No complaining

When I left, they were really confused because I'd just been there a few months. I kept replaying that steve jobs quote in my head: "Have the courage to follow your heart and intuition. They somehow already know what you truly want to become. Everything else is secondary." This line has served me very well a number of times in my life

Gm, the pursuit of excellence is realizing limits are just conventions most people never question

Pick your commerce leader Shopify will become Amazon faster than Amazon can become Shopify

My path as a PM: - McDs cashier @ 21 ($9.75/hr) - PM intern @ 22 ($4.5K/mo) - Math tutor @ 23 ($25/hr) - Sold first co @ 24 (Got the 💰) - First PM job @ 26 ($100K) - Shopify PM @ 27 (📈) - Snap PM @ 31 No such thing as timeline for life. Your journey is defined by only you.

Crazy. You literally make more as a refugee than a new grad software engineer in Canada