I just published "Product Management Mental Models for Everyone", a latticework of ideas for building products blackboxofpm.com/product-man… Also coming to you in tweet form: 1⃣-4⃣: 💰 Figuring out Where to Invest 5⃣-🔟: 🎨 Designing and Scoping 🔟➕: 🚢 Shipping and Iterating

"Swinging the Pendulum" is my favourite operating principle @Shopify. I learned it here and used for many years in leadership. It's a metaphor we used to communicate when we need teams to start optimizing for the other end of the spectrum. Here's how it works:

Want to build a better mint.com... where it might have been today if it never got acquired and left for dead in 2009: - ML classifying that actually works - Privacy-first (paid, no ads) - 3p apps (tax, calcs, etc.) - FIRE mgmt - mobile 1st What else should it do?

PM is an awesome job: make big decisions about the product, often be the face of it in presentations/meetings, etc. I haven't been one for years now and have since led almost every other function, so I feel like I can share a different perspective freely... PM is the worst job:

Applications for Shopify's #DevDegree close Feb 17 - work @Shopify & earn CS degree in parallel - WE pay tuition & salary, ~$160k over 4 yrs - after grad, u have: $(vs debt) + CS degree + real world exp The best opportunity in education on the planet. devdegree.ca

I once vented to a C-level about all the problems I was facing with reports/peers/stakeholders, and how I feared politics was taking over the culture of the company. "Brandon, the only antidote to company politics is growth." that really stuck with me over the years

Brought a new baby into the world on Thursday and got vaccinated today, both stellar experiences. Thank you 🇨🇦 health system and front line health care workers

To be clear, PM is an awesome job and it's a privilege to be able to determine product direction. But in my experience, PMs get zero empathy day-to-day despite being some of the hardest working/impactful ppl in a company So next time you see your PM, give em a hug 🤗 and say thx

The Dev Degree from @shopify is open for applications. In 4 years students get: 1. CS degree 2. 4,500 hrs work experience at a tier 1, global company 3. Salary, vacation, and a solid network This is the most zero-downside, massive-upside opportunity in education today👩‍🎓💻🤑📈🤝

While I've always loved investing & have managed my portfolio for 20 yrs, I wouldn't call myself a good investor. It's so hard to be good that I don't even try - instead, I've devoted most of my learning to how to avoid being bad. 1/x How to Not be a Bad Investor (thread) 💸:

every time I come to Silicon Valley, I’m reminded that being the right-sized fish in the right-sized pond is the most important career decision for most ppl

The Science Center shut down seems like it’s the LEAST polarizing issue this city has seen in a decade People love it, and no one wants it to move. That viewpoint seems to cross cultures and socioeconomic classes. The ppl aren’t dumb- everyone knows something sketchy is up.

After an unreal 7.5 years, I decided to hang up my @Shopify bag at the beginning of this year. It's hard to process all the memories, but when I reflect on my time here I think about the words: ambition, resilience, kindness, and growing-up...

Had my 1st night at home as a new dad last week. The baby started crying, and I kid you not, I deliriously said: "Hey Google, stop."

Leading large teams over the past few yrs - the most in my career - has been rewarding, but also very challenging I'm lucky to have been given that opportunity, but it's still hard, and walking an infant around the kitchen counter 1000x on pat leave helped me reflect on why 👇

If the public raises $6M, can we keep the science center open? @oliviachow @fordnation I’ll personally commit $10k if you commit on your side and we raise enough.

After coding everyday for two months, I am convinced that programming is going to be a core part of a Product Manager’s job in the next 5 years or so. Huge paradigm shift in the role incoming. Prototypes and evidence of user/market validation will be the new project proposal.

I'm completely broken today. I could barely look at my kid in the morning without welling up. If the targeted murder of 8 Asian women doesn't evoke rage in you, maybe we aren't alike after all. The media will ignore this as they have ignored all Asian hate crimes in the past yr

See the report from the 3rd party eng for the Science Centre. Says cost to repair is~$6MM, $4MM to be spent this year, and $2MM over the next ten years. Does not reco closing the facility. Wtf is this corrupt bs. $4MM now is peanuts for the social good documentcloud.org/documents/…

The neighbourhood "ice-cream truck" business model but for fresh, high quality coffee and baked goods would kill it right now. Instead of the "kids chime", play hipster coffee-shop music on blast: people order cortado from their porch. ☕️🥐💸

Two months into a home renovation and the parallels to building software are stark: - complexity emerges once your start building - design and engineering in tension - time/money/quality tradeoffs - sequencing nightmare - stakeholder mgmt (wife) Using all my PM skills for real

After all these years, if I had to structure teams around a single principle it would be: organize them around the people who care the most [about whatever goal/problem] caring > skills, experience caring == pace, grit, empathy...the rest you can learn on the job

There are 3 ways to enable a team's work: 🏁- Give them a goal but they own the timeline ⏰- Give them a timeline but they own the goal 💸- Give them both with limitless resources (eg. ppl/$) to make it possible Anything else and you're fooling yourself or don't trust them

Shooting hoops at the park in between mtgs & a 13 yr old wearing a raptors sports camp t-shirt challenges me to a 1 on 1. Thought about the best role model I could be at that moment...and proceeded to whoop his ass 11-1 Took it like a champ, huge respect for the little man.

1/ The way China has been portrayed by media over the last 4 years is a huge driver of the increase in Asian hate/violence, and also why it's under reported by media.

Fun read. When I joined @Shopify in 2015 I thought I was late to the story, but all the crazy stuff was just about to happen. Thankful for the ride. Amazon selling us the webstore biz was my 1st project, and a great subplot itself, for another time. bloomberg.com/news/features/…

4. Constant Anxiety Imagine your whole job is having ultimate accountability for the output and zero direct control on the input. Couple that with "go faster" from #2 above and constant "no" from #3. You haven't PM'd until you've sighed and declared "I'm fucked."

I took off all of 2023. Focused on health, family, travel… yada yada yada it was great. But during that time my brain atrophied, my work ethic diminished, and it got harder to focus. Despite a deep desire to build again, I've found that getting back to a grindset has been hard... It’s slowly getting better now, and I wanted to share some reflections on how I've reinvigorated myself. While I don't think there's anything novel in these ideas, for any people out there that are struggling to find the spark again, these things have worked for me. 1/ Understanding my own psychology for building was the foundation. Why I'm building has changed so much from when I was younger: from money and status to impact, adventure, and friendship. While this change in mindset will help me be more patient, long term maximizing, and selective about who I work with and what I work on, the tradeoff is that I've lost the urgency I used to have of, well, being broke. That's a big problem, because urgency is paramount for success. So a lot of my focus has been trying to trick my brain into feeling pressure and growing my brain's capacity to work. 2/ Growing capacity through adding friction to your life One of the most interesting realizations has been that the more friction I've added to my life, the more I'm able to produce. Too much free time has made me lazy, so taking it all away has proven to make me value time more. Changing my daily life to require more effort has also increased my capacity: - I stopping paying for all these privileged services I had like house cleaning, laundry, yard work, etc. - I started cooking ~every meal for myself and my kids. - Bike everywhere, no ubers This is like an extra 2 hours of lost time everyday, but paradoxically the extra busy-ness is making me perform at a higher level with the remaining time. Also I'm sleeping way better. 3/ Purposely creating social pressure (in the right amounts) As status maximizing animals, we are rarely unaffected by expectations. The more people I’ve told I’m building, the more pressure I've purposely created on myself to produce something. The balance and tradeoff here is that you don’t want to create so much status pressure that you make status maximizing decisions instead of product maximizing ones. A classic example is being afraid to show early prototypes and experimental ideas to people for fear of being judged to be performing way below expectations. The truth is at this stage in my career, I think people have high expectations of what I’ll be able to build, even though I haven't done a true 0 to 1 in 15 years, and that pressure can lead me to hold things back much longer than is optimal for speed to product-market fit. There's a point where I think too much social pressure is a negative, but better to just create it first then slow roll after imo. 4/ Be around people grinding Creative energy is infectious. Hustle is infectious. Competition is infectious. You have to surround yourself daily with that energy to sustain prolonged effort. - Joining @535Toronto brought community, physical proximity, and fun - Working out of public libraries full of students vs. coffee shops full of 30-somethings - Saying yes to more cold emails from first time founders, and seeking out and catching up with old colleagues There's probably a half-life for all these tactics, but I know over time my mind and body will adapt and it will become the new norm for me again. And while I'm not quite near 2019 Brandon levels of productivity, I'm encouraged to be on the way... To all those trying to reinvigorate themselves, happy building 🙏

I’m up to over 55 angel investments… is there software out there to help manage & contribute to portfolio cos? Features like: 1. Cost basis, markups, etc 2. Sync with email to know most recent update 3. Open roles to help with recruiting 4. Feed of customer and company news

Remember you once dreamed of the life you have now

Dear Santa, this year I wish for @SlackHQ features to help protect my and my team's focus/sanity 📵 1. /Dnd weekend 2. Let ME choose not to notify someone when I msg 3. Schedule messages to be sent later 4. Notification settings at user lvl so one person can reach me in emergency

Would be a really great day for @Wealthsimple trade to launch in US...

1. Thankless When a designer/eng produces work (the product), it's objectively exciting and ppl on the team celebrate (esp the PM) When a PM produces work, aka figuring out what to build, on avg they get - "ok... [you better be right]" or "by when?" best case you get a nod😐

Walk in clinics in Toronto drive me insane This pic is one minute after the neighbourhood walk in clinic opens. This is the second room, there’s another full of families through the doors. Doctor still isn’t here, 45 min late. 3-4 hour wait even if you come 10 min early. These are privately owned clinics but I guess the owners see these lines and think they don’t have to compete. If there’s any clinic owner out there who wants to destroy the competition, increase profit, AND give people what they want, I’d love to work with you on a simple change that will fix this entire process. I’ll build and implement the entire thing for you. 1. Let people join the walk-in waitlist online, requiring a $50 deposit. 2. Notify them 30 min and 15 min before the appointment 3. 10 min grace period for being late, after which you lose the $50 deposit 4. If you make the appointment on time, deposit is returned and it’s free Do this and there will be no more wait lines, no more coalescing large groups of sick kids together to infect each other, no more frustrated parents This will increase profits and outcompete because people will rather have an appointment 6 hours from now waiting in the comfort of their home than 3 hours in a germ infested waiting room

It’s funny how 12 months ago everyone thought that Product Management was dead Now it feels like it’ll be the only job left

When we bought our house the last owner asked us to continue their tradition of doing cotton candy on Hallowe’en We thought it was random, but it’s turned out to be one of the most fun, joyful things ever to bring to the neighbourhood Served over 300 tonight

Grateful for the life lottery I won. They had it hard so I could have it easy. Thanks mom, dad, and 🇨🇦

Cybertruck design is cray, but imo very strategic: 1. Existing stigma against Teslas as lame, esp from truck drivers 2. Use Roadster playbook where electric was also "lame", so they made bad ass sports car & beat ppl over the head to overcome stigma 3. Make fucking tank

I wish I could filter all tech advice/experiences by size of org and user base it was learned from... What is good advice for scale A is often bad advice at scale B and disastrous at scale C

Bolt is Eating itself (thread):

In 10 years there will be hundreds of companies built by ex-Shopify employees, and thousands funded by them. Flywheel: We hire entrepreneurs to build Shopify -> they build a platform for entrepreneurs -> employees learn to be entrepreneurs here -> they fund entrepreneurs -> ...

By swinging the pendulum and changing focus periodically, we essentially accepted more extreme outcomes in the short term, but in the long term arrived at the middle ground we sought after

5. Useless until proven useful When an eng/designer joins a team, it's celebrated because ppl see them as tangibly helpful to output (more code, UX) When a PM joins a team, it's default skepticism and they have to prove they should even exist. "What do you even do anyways?"

A friend got my 2.5 yr old a full size motorized excavator that took two hours to build and takes up half the width of my house Not sure if great friend or troll. Possibly both.

2. Eat shit all day (from above) When ppl see PMs interact often with leadership, it's mostly perceived as enviable. Truth is most of what they're hearing is "Why isn't it done?", "Why isn't it growing?", "This product sucks" note: this is shit the team doesn't need to eat now

Excited to share that I invested in the film "38 at the Garden" about @JLin7's epic night against Kobe 10 yrs ago. Premiering at @Tribeca in June Linsanity meant so much to me and the Asian community - grateful I could support Frank Chi, @Travon & @Samir4GTG in getting this made

Interesting poll results. I think that everyone who's considering leaving 🇨🇦 is simply over-valuing money in their life. Just like earning $1 as an entrepreneur is more fulfilling than 10x as an employee, building a company in Canada to me is 10x more rewarding than building elsewhere, because Canada is my home. Yes, on average we are less ambitious and risk taking than the US. Yes we have higher taxes. Yes it's harder to build a business here. But the flip side is that we are also a more harmonious society. We have less crime and less financial inequality. We are rich in natural resources and rule of law. We are full of diverse people, and have a culture of tolerance, acceptance and kindness. That's worth protecting and grinding through many generations of bad policy, in order to make it better for the next generation of Canadians. Cap gains inclusion can go to 100% - I'm still building here, because winning here means more to me than just the money.

3. Eat shit all day (from around) PMs only create output through others, so every interaction is basically asking (begging) people to do more work or trade off their quality standards, and no one likes that. Hence constant "no.", or "find another way", "too bad"

I used to call my 8 month old son a “covid baby” because he was conceived and delivered during the pandemic. He just levelled up: conceived, delivered…and contracted 😭 Going into a brutal family quarantine for next two weeks, wish us luck.

Swinging the Pendulum is hard to use because it makes you look inconsistent and disorganized as a leader. But it's a realist operating principle that acknowledges the limits of communicating nuance in large company, and it IS consistent - just over the long run.

Years ago I told my boss how a great hire changed my life. I got some subtle leadership advice in return. Me: "If I could only find more ppl like her..." Him: "Keep in mind, you can't have too many *great* ppl on a team. They'll trip over each other. You mostly need good ppl"

After a 3-yr hiatus from writing, I've found the motivation to break the silence: next week, I'll be interviewing the elusive @craigmillr, former CPO & CMO of @Shopify, and a company legend Sign up to get it first: blackboxofpm.substack.com Have any questions for Craig? Reply 👇

6. Lonely There's often more than one eng/UX person on a team: they can pair, they can collaborate, they have community everyday PMs have their spreadsheet and keynote presentation

Got 4 investor update emails this wknd: reading the ups & downs of these founders reminds me that being (a tiny) part of their journey is half of my "returns" Win or lose, seeing people create something with nothing-but-persistence has a huge impact on my own hopes and dreams

This us open women’s final is so nuts: - a Filipino/Ecuadorean Canadian vs. a Romanian/Chinese brit (also born in 🇨🇦) - both teenagers - both low rank and come out of nowhere to beat the best in the world on the way to the finals Beautiful symbol of the power of immigrant grit

Happy Halloween 🎃 from the little guy/avocado

1/ It's painful to see racism against Asian Americans/Canadians intensify during COVID. This article by @JohnTheCho hit hard and made me reflect on a lifetime of that pain. As someone born in 🇨🇦, it's times like these where sadly I feel I have no home. latimes.com/opinion/story/20…

On resilient culture: every time you swing the pendulum, you end up blowing up roadmaps of many teams. When you do it regularly, though, you train teams to let go of their sunk cost and embrace company > team > self (assuming you communicate The Why effectively, which is hard)

Common cold reach outs I get are from students/early-career ppl who aren't from eng/design backgrounds, want to be PMs in tech, and are looking for advice on how. (tldr; build stuff) It's so energizing to see PM become something people actually focus on becoming at age 20🔋

It's been a while, and this one took some time but I hope it's useful: I just published “The First Principles of Product Management” medium.com/p/the-first-princ…

Will do my best to only buy Canadian 🇨🇦 for the foreseeable future @shop please let users filter for Canadian merchants only. Easy win and generalized utility - let’s go

My friend after 15 years as a software engineer

Things I'm bullish on in a digital by default working world: - timezones - meritocracy (less likeability, more on output) - better mgrs and mgmt theory - transparency - diversity Work will have a different social meaning, but the actual productivity could increase a ton

Excited to officially launch Ads on our App Store today! With over 3000 apps, it's harder than ever for new devs to get discovered, so we're happy to share that we're also providing $100 in free credits for all new devs, today and in the future.

This presentation took me 3x longer than normal due to pat leave brain atrophy. 🧠😴 But omw to SF now & excited to share what we learned building Shopify's platform, and what platform work means for PMs. Might even write an accompanying post after...been too long ✍️🤔

After 37 investments to date, fewer things in my life have been as broadly rewarding as angel investing: meet inspiring founders, grow 🇨🇦's tech ecosystem, make $, and do it alongside friends and operators from @Shopify. Thankful everyday I got lucky enough to be participating

This Google sheets plugin is a great example of product extension platforms at work. My opinion on @figmadesign instantly went from "don't care" to "take my money". Also, spreadsheets still rule the world & all products should integrate with them even with no obvious use case

New desk, new view, new beginnings let’s go @535Toronto

🛍️Shop Pay is now a NATIVE checkout option in Facebook and Instagram. This is bananas and another level for Shopify. Merchants - if you aren't already, it's time to get on this train 🚄

Incredibly proud of the team for 🚢ing this today. Thank you also to our app partners, who have been very patient with us during this rollout. Things we ❤️ about it: 1. 🔥 new design 2. Collections for apps in French, German, and Japanese 3. 100+ new subcategories of apps

We're kicking off #ShopifyUnite in style this year, with a beautiful new developers.shopify.com landing page that features some incredible stories from some of our developer partners! Check it out 🙌

Shopify can make this decision precisely because we're mission-driven to create more entrepreneurs above all other concerns More developers --> better apps/stores --> more successful merchants --> more devs --> ...

Only the mayor can get me out to a conference. #homecoming

I just published "Managing and Developing Product Managers" blackboxofpm.com/managing-an… (I make the most boring post titles ever)

Haha sure When growing, people focus on the team game because the continued success of the group is optimal for the individual When stagnant, people (esp the ambitious) end up focusing on increasing their share of a fixed pie == optimize for themselves instead of co == politics

App developers often want to build for the masses on Shopify, but I always remind them why building a "niche" app on apps.shopify.com is a great strategy Solving a problem for 0.5% of merchants, at $20/mo, makes you a $1M ARR business growing at 50% YoY

yes nytimes.com/2020/11/24/magaz…

In the last 12 months, our little team grew from ~20 to 110 people 🙃 My big takeaway: the diff b/w great ppl and good ppl is exponential when you’re growing quickly. Great ppl scale themselves and still manage to do the work, good ppl can only do one. The difference compounds.

stop seeking the right answer, start seeking the best trade-off

We're usually heads down executing with the teams, but yesterday my leadership team got together to celebrate the year Couldn't be more proud of this group & their accomplishments over the past few yrs. Am lucky and grateful🙏 Follow them to track ppl making waves at Shopify:

It also had two very powerful second order effects: 1. it allowed breakthroughs on the product 2. it trained our culture to be resilient to change

By far the biggest leadership learning for me in the last 6 months has been learning the value of staying silent. Still learning... Let teams feel ownership, solve their own problems, and organize the way they see fit. This has held true in 1:1s, meetings, and slack channels.

Just got this sick hoodie for my lunar birth year. Dopest Chinese Canadian swag I've ever seen - nicely done @roots

If left down it for a week, this Facebook outage could enable some epic A/B tests on society

Excited to share that @Shopify participated in @pipe's latest round. @harryhurst and team are building an important capital market, one that is founder-first and mission aligned with our focus on creating more entrepreneurs

Our COVID Response Plan: - 90 days free to all new signups - Gift cards now available for all plans - Local in-store/curbside pickup and delivery for POS - $200m commitment on Shopify capital - Community forum, live webinars & online meetups for support shopify.com/covid19

We'd often oscillate on telling teams to, eg: - optimize for speed vs. focus on quality - everyone needs KPIs vs. only qualitative goals - don't think about revenue vs. generate revenue! This seems needlessly confusing - why weren't we consistent, why didn't we choose?

Spent some time analyzing my angel investment portfolio recently and wanted to share the good, bad, and ugly. Stripping out advisory/board shares, I've made about 65 investments to date: 10 are dead, 2 sold, and the rest are still alive in various states of health. 1. Investing Overview When I started angel investing, I had no idea what I was doing. I would just cold approach founders at the end of a demo/meeting or twitter DM ppl. As time went on, deal flow improved and I starting writing cheques more frequently (thanks @Shopify). I also got smarter about selection via more reps and also some work experience in investments/M&A. You can tell by the timeline of these investments that I made the vast majority during the ZIRP + Covid Bubble years of 2019-2021. That of course will likely not bode well in the long term and I expect to have terrible returns vs eg. Nasdaq

Excited to share my conversation with @craigmillr, former CPO of Shopify & a humble giant in 🇨🇦tech We discuss: - his early career & 9+ yrs at Shopify - Key decisions in Shopify's product history - Hypergrowth & being an exec 👀 piped.video/6F1iN4sAVEs 👂open.spotify.com/episode/7fa…

While we work hard to make this scale possible, @Shopify's ecosystem is a huge part of what it takes to pull off the most important day of the year for our merchants Thanks to all the @ShopifyPartners out there who are all hands on deck and in war rooms this wnkd 🙏👩‍💻👨‍💻📞

Pretty strong response from @JustinTrudeau. Easily his finest moment as PM, gotta give him credit. Likely the right move too - tit for tat is surprisingly game theory optimal in trade wars. piped.video/live/92rutFiIWAM…

Thrilled to share our strategic investment and long term partnership with @Yotpo today. Yotpo is one of the most impactful partners in our ecosystem & their apps are used by hundreds of thousands of merchants on Shopify. @ttagrin and @omricohe 🤝

Inspired by this, I'm joining in If you are under 25 and $2,000 or less can change your life, please apply for a trajectory changing grant here: justinmares.com/apply-for-an… I'm sponsoring $10,000 USD, with 50% reserved for 🇨🇦'n youths (just put that you're 🇨🇦 in the 'FYI' field)

10. Finally, you always need to put up a front as the leader. To your team, to your peers, and to your bosses. It can be draining and lonely. At the same time, leaders don't deserve sympathy, because it's an incredible privilege that many would dream of having. still hard tho

too many to thank but: @skanwar for the partnership @atleeclark for being my internal cofounder @vlaurenlee for mking me look good @anna_lambert_ work bestie @craigmillr @harleyf for the wisdom & having my back @tobi for building the co that chg'd my life 🙏 (what's nxt? tbd)

I have a solution for the debate on using a 6-page memo vs. decks-that-oversell-reality: purposely ugly decks

Really proud of the @shopify Toronto team today 🙏. 100s of us got together & donated $20k+ to support the victims of last week's Danforth tragedy. Funds are being administered by @PaulaFletcher36 and @mfragedakis Support it here: gofundme.com/danforth-strong #danforthstrong

Early rendering. Steps for coffee merchants (post truck) 1. signup for Shopify 2. add Shopcodes app apps.shopify.com/shopcodes 3. get QR codes for products 4. activate @shop pay for fast checkouts 5. orders come with buyer address so you know which house to leave the coffee on

It’s so crazy to me that I barely Google anything anymore, like ever. From 1000 times a day to zero in 2 years. Truly unimaginable back then.

What a time to be alive. Let's go! #WeTheNorth