• In university, I spent 3 years running a startup incubator, hosting countless pitch competitions and hack-a-thons.

• After graduating, I spent 2 years doing due-diligence and strategy work for Private Equity firms and their portfolio companies.

• After that, I spent a year building my own startup, after pitching for and securing seed funding via a SAFE.

So I know a thing or two about what investors are looking for. And if I had to some it up in a single sentence, it would be:

Investors are looking for businesses with minimal risk.

This is true no matter what stage they invest in. What varies at each stage are the types of risk they’re concerned with.

For example, growth/late-stage investors targeting mature companies might worry about:

• Regulatory risk — Will changing regulations break this business’s moats? Will new compliance burdens lead to unexpected costs?

• Macroeconomic risk — Will tariffs and geopolitical issues screw up this business’s supply chain? Will international customers churn?

• Liquidity risk — Will IPO/M&A markets be open? Can investors get their money out?

Meanwhile, early-stage investors targeting startups worry about simpler (though more uncertain) types of risk. Like:

• Market risk — Is there any real demand for this? Is the market big enough to support a 100x return?

• Technical risk — Can this technology even be built as envisioned? Might it require far more time and resources than expected?

• Financial risk — Could this team run out of capital or mismanage their cash flow before reaching sustainability or the next funding milestone?

In-between funding rounds, a founder’s job is to de-risk the business—to consider what risks investors will obsess over when you next fundraise, and do what they can in the interim to minimize those risks.

For early-stage startups raising seed funding, there’s one thing they can do that will de-risk their business more than anything else. If they can do it, funding of some kind is all but guaranteed.

Traction. Do you already have a product with paying users?

Traction isn’t a lofty hypothesis, it’s undeniable proof. Proof that there is a problem, there is a market, there are people willing to pay for a solution, and you are capable of building that solution.

Whatever other risks investors still see in the business, traction in a sizeable market can be enough for at least one of them to write you a cheque.

Unfortunately, non-technical startup founders find themselves in the difficult position of having to de-risk a business with nothing but a slide deck.

They can address Market Risk simply enough. Surveys can validate there’s a problem worth solving; back-of-the-envelope math can point to a sizeable market; letters of intent (LOIs) from prospective customers can indicate a willingness to pay.

But there’s little more de-risking one can do without a product.

As a result, I’ve seen the same movie play out countless times:

• A non-technical founder pitches their idea and says, “this is a huge opportunity, we just need the capital to build it.”

• To which the investor says some flavour of, “If you can’t build it or find someone who can, I’m not interested.”

And that chicken and egg problem stops many founders from participating in the startup world. You need money to pay engineers to build the thing, but no one’s going to give you money unless you have engineers to build the thing.

Of course, this is where I bring up AI.

But my advice isn’t so simple as “Step 1: vibe-code your product. Step 2: profit.”

Because one of the risks we haven’t discussed yet is competitive risk—most VCs don’t invest in direct competitors. So they want to pick the winner.

So even if you’ve vibe-coded an MVP and earned some traction with it, how do you make a strong case that you’re positioned better than another startup with a stronger team or an incumbent with existing distribution?

Sure, you might be first to market, but does that markedly improve your odds of success over the long-run?

That said, I believe non-technical founders, even in a post-AI world, need to be more strategic. In addition to a vibe-coded MVP, they need two additional ingredients:

1. A moat

2. Explosive growth

The Moat:

There are 7 moats (or what Hamilton Helmer calls 7 Powers). I’ve written about them before, and I’ll likely do so again soon. They are:

• Scale economies

• Network economies

• Counter-positioning

• Switching costs

• Branding

• Cornered Resource

• Process Power

I’m sure you understand most (if not all) of these moats intuitively just by their names. The common theme of all moats is that they are both durable and differential. A business can’t just be a good product that a small number of users love. It must also build a defensible moat that compounds with growth.

The growth part is important.

If you only have 10 users, your switching costs aren’t defending a very large slice of the pie; your branding is weak; and your network and scale economies are easy to catch up with.

In contrast, a functional MVP with built-in moats whose adoption is growing rapidly is the foundation for a durable business. One that can defend itself from competitors until an engineering team is brought online to build the next evolution of the product.

Take the example of a non-technical founder aiming to build “Airbnb for household items”, allowing people to rent power tools, camping equipments, party decorations, and other useful possessions from other users on the platform.

This business will have benefit from network economies—the platform becomes more useful the bigger the user base grows.

If the founder vibe-codes a “good enough” website and/or mobile app and rapidly snatches up the early-adopter base, then they’ve got a significant edge on the competition. In a network-effects driven market, the winner is the business with biggest user base, not the one with the best-engineered platform.

So non-technical founders: your day is coming, if it’s not here already. Think hard about the moat(s) your business can have and your go-to-market strategy for viral growth.

Only with moats and growth can a “good enough” vibe-coded app be good enough.

Save for Raptors games, house work, and the occasional outing with my mom, he worked every hour he was awake.

How do you top that?

His work ethic: remarkable. His return on his time invested: less remarkable.

No doubt, my dad did incredibly well for himself. Especially given his humble beginnings. But his output didn’t match his input.

And for a long time, that didn’t compute to me. How could a man working every waking hour for decades be anything less than a billionaire?

I didn’t know the reasons why, but my mom sure did. She yelled them at him often:

• “You’re always doing the work yourself! Hire and train someone!”

• “You’re undervaluing yourself! You could charge twice as much!”

• “You’re doing too many things! Just focus on one!”

My dad knew all this too. He knew he should look for leverage, put a higher price on his time, and focus all his energy on one endeavour.

But knowledge isn’t enough. He let his habits steer him down the same road each day, and it takes a lot of conscious effort to put your hands on the wheel and turn down a different path.

I’m my dad’s son. I’ve got the same instincts to grind it out—to focus too much on how I can work harder and too little on how I can work smarter.

But when my dad passed, that started to change.

I stopped being so diligent with my Habit Tracker, got rid of my accountability coach (which I talked about in my last article), and instead started doing something I’ve termed, “Unit Vectoring”.

In math, a Vector is a quantity that represents both magnitude and direction. A Unit Vector is a Vector with a quantity of 1—it represents only direction.

When we work towards a goal, both magnitude and direction are relevant. You want to move towards your goal (direction), and you want to do so quickly (magnitude).

But for whatever reason, my brain focuses mostly on the magnitude part of it. Intense effort is something I can feel. A properly chosen direction comes with less immediate feedback.

But direction is what deserves all our attention. Unless you have your direction right, magnitude is just a distraction.

If you want to go to the beach in L.A., the best way to guarantee you never get there is to head North, South, or East. It doesn’t matter if you’re on foot or in a sports car.

But if you head due West, you’ll touch sand eventually.

Unit Vectoring is my daily reminder to focus only on direction and ignore magnitude.

The way I often phrase this intention to Zameer (my CEO, bestie, and roommate) is: "Let’s focus on doing the right things, the right way, in the right order. And the future will take care of itself.”

I still work hard, but the panic is gone. Less thrashing, more progress.

Productivity with peace.

And when I moved to Boston 3 years ago, I had a lot of goals.

• Become a highly-respected name inside my company, Boston Dynamics.

• Build a million-dollar side-hustle outside work hours.

• Become a lethal pickup-basketball player.

• Get (and stay) in the best shape of my life.

• Write a newsletter with a massive following.

• Call all of my friends back in Canada regularly.

• Maintain and grow a network in Boston.

• the list goes on...

I crafted a long list of habits that I felt were the right set of inputs for all these goals. And I tried my hardest to stick to it.

But I just couldn’t keep juggling all those balls for more than a few days before one or two dropped. I made progress on all those goals, but could never declare victory on any one of them.

Of course, my self-flagellating mind chalked this up to a lack of effort on my part. I could do all these things, if only I had the grit to stick to the program.

So about a year after landing in Boston, I went on Fiverr and hired a great guy named Michael to be my ”accountability coach”.

Every morning, I’d text him Michael a plan for the day. And every evening, I’d text him a reflection on the day along with screenshots of my habit tracker.

In the year that followed, my effort and consistency improved, but my results were more or less the same. I never “broke through” on any of my goals, and I’d still drop a ball every few days.

Until 8 months ago, when I wrote my first line of code for Wednesday Waffles.

That’s when every ball dropped.

There’s discipline and then there’s devotion. Discipline is about forcing oneself to act, often through self-control and willpower. Devotion is a more natural, love-driven commitment that makes actions feel effortless.

I was disciplined with my habits. I was devoted to Wednesday Waffles.

Waffles was—is—an opportunity to make a meaningful difference in the world, and do it while working alongside some of my best friends.

Few things feel as important when compared to that. And, honestly, few things are.

Some things—like staying healthy and spending time with your loved ones—are important no matter what season of life you’re in. But some things—like working on your lefty layup at the YMCA—are not. You need the wisdom to know the difference.

But out of sheer habit, I kept working with my accountability for a few months after starting Waffles. I’d send the morning plans and evening screenshots, same as before. But my heart wasn’t in it.

I gave myself permission to let go when my father passed away. He lived “groundhog day”, working tirelessly towards every one of his professional goals every single day, until the day that he died. And it didn’t look fun.

I’m now choosing to see life as a cycle of seasons—each with its own weather, each asking something different of me.

This season is Waffles. My job is simple: show up, ship joy, repeat.

So I’ve thanked Michael for all his help these past couple of years and am now taking things one day at a time.

My new metric for a good day is one line long: Did I push Waffles forward? If the answer’s yes, that’s victory.

Some balls have dropped. Rubber ones—like learning how to dunk—bounce. The glass ones—my health, the people I love—will stay in hand.

Everything else can wait til next season.

Last week, our co-founder David got married. He and his wife are practicing Christians, and throughout their traditional Nigerian wedding, church ceremony, and reception, God was joyfully celebrated and gratefully acknowledged throughout. Watching their faith unite their relationship, families, and community of friends in Toronto was genuinely beautiful.

After the wedding, some of our close friends stumbled back to my place, tipsy and still in suits and dresses. We talked late into the night about God and religion. By 3 am, we resolved to attend Sunday Service at David's church the next day.

Hungover, tired, and barely on time, we actually followed through.

It was an amazing experience.

Upon arrival, there was free coffee and friendly mingling outside the church. On our way in, David's pastor recognized me from the wedding, pulled me aside, and offered to chat about my Dad's passing if ever I needed it. Inside, the church felt like a concert—the band played for half the service while pastors preached.

When they invited people to come forward for individual prayer support, I found myself lining up. I paired with a young volunteer named Ivan, who offered a touching prayer for my Dad. Even for someone who didn't know the words to the songs or how to pray, I felt welcomed and comfortable.

Throughout the service, we were gently prompted to engage with strangers—nothing intimidating, just simple things like "give seven people around you a high five" or "ask someone new about what they did this weekend."

At the end, newcomers were encouraged to meet outside, ask questions, and learn more. It felt exactly like a community. If I were religious, the first thing I'd do moving to a new city is find a church like this.

The service was perfectly crafted for building and maintaining strong community bonds:

• It was genuinely fun. Whether you were greeting guests, serving coffee, playing in the band, or simply sitting in the pews singing along, everyone was smiling.

• It was effortless. Building deep relationships requires a lot of conscious thought and planning—you need to find people with shared values, build trust with them through vulnerable experiences, and commit to investing in the relationship regularly. Sunday Service gives you all of that out of the box. All you have to do is show up at the same time every week. Effortless.

• It fostered new friendships. The welcoming atmosphere, the casual coffee chats, the friendly greetings at the door, and the simple invitations to connect with those around you during the service all combined to effortlessly foster new friendships.

• It was inclusive. Young kids, older people, even atheists—everyone felt welcomed and involved. No one felt out of place.

• It was designed to grow. Friends brought friends, who were then invited to become members and encouraged to support opening new churches elsewhere.

I walked away wondering how I, as someone not religious, could find a similar kind of community. It clicked for me pretty quickly: this is exactly what we're trying to do with Wednesday Waffles.

Now I'm wondering: how do we infuse Wednesday Waffles with the best of Sunday Service?

• How do we make it fun? Can the app spark excitement and anticipation every time you record or watch a waffle, instead of feeling like a chore?

• How do we make it effortless? Can we create a predictable rhythm for making and watching waffles, reducing stress and enhancing ease? Can a user reap most of the powerful benefits by simply showing up on Wednesdays?

• How do we make it inclusive? Can we design an app where users feel comfortable inviting anyone—from colleagues and grandparents to distant friends?

• How do we foster new friendships? Can we make an app where you not only bring your existing deep connections, but could potentially make new ones?

• How do we make it grow? Can we gently encourage users to continually invite loved ones, organically expanding our community?

I’m not religious. I never was, and I likely never will be. But still I yearn for many of the beautiful things religion offers, like community.

But maybe we can create a community that isn’t tied to a religion but still offers much of the same benefits. Maybe, just maybe, Wednesday Waffles can be our Sunday Service.

“The only kind of writing is rewriting”

— Ernest Hemingway

I’m happiest when I’m writing code. And yet, a couple of weeks ago, I was dreading the idea of writing another line for my startup’s app, Wednesday Waffles.

Our app has tons of terrible reviews, all related to our ever-growing list of bugs. And, if I’m being honest with myself, even if we were to squash all those bugs overnight, I don’t think we’d be left with an app whose UX is perfect match for the problem we’re trying to solve.

I knew that incrementally improving the app just wasn’t going to get us where we want to go. I felt stuck. Until I started thinking like a writer.

Any seasoned writer knows that the magic of a great book is never found in the first draft.

A great writer is willing to treat their first draft as an outline, not a finished product. They’re willing to rewrite their second draft from scratch, with a meaningfully different plot and cast of characters. They’re willing to hand that second draft over to beta readers to rip to shreds before writing their third.

And the very best writers are will continue that maddening cycle of destruction and recreation until they can look at their manuscript and say, honestly, “That’s the best I can do.”

In the writing world, there’s an expression for this ruthless cutting of the imperfections you’ve grown to love:

“Kill your darlings.”

In the software world, we should also get comfortable with the art of revision. Sometimes that means letting go of code we’ve poured months of effort into, and embracing a fresh start to craft the masterpiece our users deserve.

After all, the best products, like the best books, come from the courage to throw out work and restart.

So that’s what we’re doing! We’re tossing out v1 of the app and building the next version (v25) from scratch.

I brought up the idea to Zameer (our CEO), and after some back-and-forth, he was bought in. We jumped in a product meeting the next day and put together the plan that we are now executing:

• We’re changing up our tech stack (Supabase → Firebase, Stacked → Riverpod) that will let us move faster in the long run.

• We’re rebuilding from the ground up with test-driven development to ensure major bugs don’t hit production and hurt our users.

• We’re totally revising the user experience using all we’ve learned these past few months, so this next version is not just less buggy—it’s also just better.

We’re “killing our darlings”, and I’m thrilled about it. I’m writing code with a smile on my face once again.

I hope you smile too when you use the new version.

“Guys, turn your cameras on. Dad’s in the hospital. He had a heart attack.”

In shock, I began packing my bags to fly back to Toronto.

The weight of the moment hadn’t hit me yet.

5:34am, Mom called again. This time, it’s a front-facing video of my Dad in a hospital bed, surrounded by doctors, with a machine aggressively performing CPR on him. Mom wanted to show us what was likely to be his last moments.

It slowly started to hit me.

6:06am, I called an Uber to the airport and woke up the two friends I was living with in Vancouver. As I began to explain the situation, Mom called once more—this time to tell me we’d lost him.

Then it hit me.

“That’s okay! That’s okay!” was all I managed to say, in some haphazard attempt to comfort my Mom and sister.

“I’ll be home soon. And mom. I love you.”

With shaking legs and tears streaming down my face, I turned back to my friends and told them my dad had passed. They hugged me tight. I got in my Uber and headed to the airport, buying a $1,000 ticket to Toronto on the way.

At the airport and on the flight, I texted friends and family, letting them know what had happened. The tears wouldn’t stop coming, and I needed support.

When I landed at Pearson airport, it took me 30 minutes to find the exit. I wandered around in a daze. It felt like a dream. I watched my body move without me controlling it.

When I finally got into another Uber to get back to my family home, I resolved to be strong for my Mom. I wanted to be one less thing for her to worry about. I planned to handle all the affairs, as I thought the freshly-minted “man of the house” should, shielding her from the burden.

When I opened the door, my mom greeted me with a smile and a hug. I immediately crumbled into heaving sobs on her shoulder.

In the hours that followed, the outpouring of love and support that streamed through our home was both amazing and agonizing.

Friends and family piled in with food, flowers, and condolences. Mom’s phone and doorbell rang every 30 seconds.

I wanted to lighten her load, but couldn’t. More than once, I asked her if she wanted to clear everyone out so she could decompress. She said, “Everyone here needs to feel welcome and grieve too.”

She handled it all with such grace, never shedding a tear and patiently retelling the painful events of that morning over and over again for anyone who asked. I was in awe of her strength.

The crowd finally dissipated around 10pm. My aunt, uncle and cousin arrived soon after, with my sister scheduled to arrive the following morning. That was the only collection of people I truly wanted within reach at that moment.

That night, I slept next to my mom for the first time since I was a kid. Before turning off the light, I read a text from my friend Reagan, gently encouraging me to share my grief with my mom instead of trying to be stoic and strong.

I did exactly that.

I told her I loved my Dad and missed him. I told her I felt I'd been a bad son. After the tears subsided, I asked her questions about my Dad—questions I'd planned to ask him someday, but always deferred to later.

For two hours, she shared openly. I learned about my dad’s tragic upbringing as an orphan in India; how badly he'd been treated by the people that were supposed to love him; and how, despite it all, he never had a bad word to say about anyone. Throughout their relationship, he'd often ask my mom, “What do you see in me?” She saw his heart—it was unmatched.

My “brave face” held for the next two days. My Dad’s memorial was the next time it cracked.

It was an open casket—my first time seeing Dad in person since my sister and I flew him out to Boston for a Lakers game. It was hard to see him cold and still. But he looked to be at peace. It was a much better final image of my Dad than him under the CPR machine in the hospital.

Despite only a couple days’ notice, the turnout for the memorial was incredible, which is unsurprising for an incredible man.

I knew half the attendees pretty well, vaguely recognized another quarter, and didn’t know the final quarter at all. But every story each attendee shared with me had the same theme: my dad was one of the kindest people they'd ever known.

After the memorial, we got to work settling Dad’s affairs. And there were plenty.

Packing belongings, selling his car, freezing credit cards, switching subscriptions, notifying the government, backing up passwords, signing countless forms…even now, there’s still lots left to do.

But once the brunt of the work was behind us, true healing began.

By the time my sister left, a couple of days after the memorial, I was still foreboding the future. I was so concerned about how my Mom would hold up without my Dad around.

By the time my aunt, uncle, and cousin left, one week after Dad died, I felt for the first time that we’d all pull through this. That everyone was going to be okay.

And by the time I was ready to fly out a few days after that, leaving my mom alone in the house, I felt happy again. I even found myself excited to see what the next chapter of my Mom’s life would like, after the dust settled.

As I write this, flying back to Vancouver, I’m ready to return to normalcy. Though my routine will look much the same as before, I feel like I’m forever changed in innumerable, wonderful ways.

I learned a lot about myself these past two weeks, but I also learned a lot about my loved ones.

I have one hell of a mother, who was the emotional rock for my sister and I these past two weeks (as she has been for the past three decades).

I have one hell of a sister, who holed up in our basement for 4 days straight, tying up countless loose ends before having to fly back to Seattle for work.

I have one hell of an aunt, uncle and cousin, who flew in and stayed with us for a full week, without needing to be asked. They brought so much life into the house at a time when we really needed it.

I have one hell of a partner, who travelled overnight from LA to Toronto on short-notice to support me and my family. Her nightmare of a flight path deserves its own article.

I have one hell of a group of friends, who delivered meals, sent flowers, drove long distances to attend Dad’s memorial, and checked in on us every day.

And I had one hell of a father, whose name I am so proud to carry. I spent too much of my angsty youth resenting him. Now, I want nothing more than to someday be half the man he was.

I’m 28. My dad should still be here. But losing someone so young teaches you a lesson that you’ve heard a thousand times before but never truly understood:

Tomorrow isn’t promised.

So if you love people, tell them often. If you have a dream, chase it. And look for the joy in every moment of your life.

Love you Dad 🧡 I hope I see you again some day.

Up until three weeks ago, I was in Boston, juggling my startup around the edges of my schedule, while holding down a full-time job at Boston Dynamics and trying to maintain a healthy relationship with my girlfriend.

Now I’m in Vancouver, full-time on my startup alongside my cofounders, and my partner’s in LA. My daily schedule is wide-open with few distractions. You'd think I'd be pumping out new features and fixes daily.

But strangely, I feel less momentum on my startup here than I did back in Boston. I'm not moving the ball forward nearly as fast as I'd hoped.

Honestly, I've put very little of this newfound time into the startup itself. Instead, most of the incremental time has gone towards upgrading my Shopify app and doubling down on writing and filming content.

And I'm not even sure why I’m doing those other things. All I know is, I always do this. When I find extra time, I immediately spread it thin across multiple projects instead of doubling down on the one or two things that really matter.

So this morning, on my 28th, I went to a cafe to figure things out.

Sitting here, fidgeting with my coffee cup, I recalled something from The Right Call—a book by sports journalist Sally Jenkins.

I couldn't dig up the exact quote, but I found an interview with her from the Washington Post where she made the same powerful point:

[People are] afraid to say, "That's the best I can do."

And it's an inhibitor, that instinct to say, "I'm going to hold back a little bit because I don't want to disappoint myself, and I don't want to have to say, oh, I failed." And I think the great ones, that's the real separator there.

Champions are willing to break their own hearts. They really are, and that's the best that I can describe it.

You know, I see so many people who feign nonchalance about something, and I certainly did that earlier in my career, because if you feel like, well, I don't care that much about this, then you don't have to disappoint yourself, and you don't disappoint other people…

But if you go about it with… "unembarrassed intensity," if you commit to doing that, you can really surprise yourself.

— Sally Jenkins

I don't pick stocks. All my money is in index funds. I always diversify.

And while diversification might be smart for money, it’s terrible for time.

I need to stop hedging my bets and fully commit to my startup. No matter what happens over these next few months, I want to look back at this summer and know without hesitation:

“That was the best I could do.”

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See you next week — Rayhan

6 months into building my startup, Wednesday Waffles, I'm here to concede that mobile app development is way way harder.

Here’s are the top 6 reasons why:

1. Apps Need Approval

Our app was rejected 6 times before we were finally approved. Every new release is a new battle.

Meanwhile, you can deploy a site in the next 5 mins if you want to. Aside from SSL certs & CORS, the web is as close to a permissionless world as you'll find.

2. iOS/Android Nuances

For sites, you basically never need to think about what browser your users are running—everyone's on Chromium.

For apps, even if you're using a hybrid framework, you'll still end up writing platform-specific code for iOS & the many flavors of Android.

3. Client-Side Patching

Bug on your site? Redeploy and get your users to press "Ctrl+Shift+R". Bug in your app? Submit a fix to both app stores. While it's in-review, stop the bleeding by patching with "Shorebird". Pray it worked, or you're doing it all over again.

4. Versioning Matters

On the web, you can deploy major front-end and back-end changes concurrently.

For your app, the "Expand-and-Contract" strategy becomes your best friend. There's a long tail of users that won't update their app for a while, but still need it to work.

5. App Store Reviews

Web or mobile, SEO is tough.

But at least when someone sees your blue link on Google, they don't also see a 1 to 5 star-rating.

Apps need great SEO + great reviews. You need to make sure you request reviews from your users and do so at the right time.

6. Native APIs

This is the big one.

Why do you download the app instead of going to the site?

Chances are it's because the app to enriches the experience using your camera, contacts, geolocation, notifications, deep linking, background video/audio etc.

You're probably building an app and not a responsive site because you need these native APIs.

You need to request permission from your users to access all of these features, and often also maintain core app functionality for the users that reject them.

—

That’s my top 6. What did I miss?

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See you next week — Rayhan

I got to Vancouver a week ago, ready to go all-in on my startup, Wednesday Waffles, with my co-founders.

The first thing I did was set up my new work desk. The second thing I did was glue my ass to it.

I had one big goal for my first week here: finish a highly-requested feature for my Shopify app, QuickGift. Once done, my girlfriend could grow that revenue stream for us while I focus fully on Wednesday Waffles for the summer.

I thought it would only take a day. I was wrong. I didn’t plan for half the tasks I needed to do, and the ones I did plan for took twice as long. Classic.

I ended up skipping the first three days of WebSummit. I told myself working on my startup felt more "founder-like" than walking around a conference listening to people talk about their startups.

Gift Receipt Email Customization in QuickGift — it’s live now!

This morning, I finally went to WebSummit. Mostly because I didn’t want to waste the ticket.

Now I’m sitting here, right after hearing JaVale McGee and Metta World Peace talk about their new careers in venture capital. And I’m asking myself: did I make the right call this week?

In just three hours, I’ve learned a bunch, had some fresh ideas, and feel more excited to get back to work. Skipping a few hours of desk time was totally worth it.

I’m not mad at myself, but I’ve made a note for next time: a little change in routine can go a long way.

Routine helps you get work done. But breaks—planned ones—make the work better. A week of pure output feels productive, but creativity needs input. Talking to someone outside your usual circle, walking without your headphones, going to a conference like this—those things shake your brain awake.

Sometimes, the break is the work.

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See you next week — Rayhan

You: “Didn’t you quit your job to focus on your startup?? A new project would just be a distrac—”

Me: *Puts a finger to your lips* “Shhh shhh…”

Before you say another word, read this quote from the book, Range. I’ve shared it so many times since reading it 6 years ago, I can almost do it from memory:

“Compared to other scientists, Nobel laureates are at least 22x more likely to partake as an amateur actor, dancer, magician, or other type of performer.

Nationally recognized scientists are much more likely than other scientists to be musicians, sculptors, painters, printmakers, woodworkers, mechanics, electronics tinkerers, glassblowers, poets, or writers, of both fiction and nonfiction. And, again, Nobel laureates are far more likely still.”

David Epstein, Range (2019)

TL;DR: Creative side projects build up transferable skills and lateral-thinking, which can improve your odds of success with your main project.

But if I’m being completely honest, none of those benefits are why I want to take on a side project.

I love working on my startup, but it’s slow and discouraging at times. I want another source of excitement and momentum in my life that feels low stakes and is totally my own.

For me, I think the perfect side project is doubling down on content creation.

Writing regularly has forced me to think through my ideas, dive deep on interesting topics, and develop my copywriting skills. It’s also been a huge source of pride for me.

As a bonus, if my content earns me a meaningful following, then I have a channel through which to tell the world about personal projects I work on, now and in the future.

If I cap my content creation time to 5-10 hours per week, I don’t see it negatively impacting my performance at my startup.

My plan is to expand beyond this newsletter into another medium. It’ll likely be short-form video (TikTok, Insta and YouTube) or short-form writing (Twitter, BlueSky, and SubStack Notes). Or both!

I’m not sure what shape the new content will take. Like this newsletter, it’ll probably be months of erratically iterating before I find my footing. All I can promise is that from June 1st onwards, you’ll be seeing (and hearing) a lot more of me.

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30 minutes ago, I had the pleasure of listening to a heater of commencement speech by Alison Schmitt — 4-time Olympian and 10-time medalist.

Among her many quotable lines was this nugget:

“Fear doesn’t show up when you’re standing still. When it does, it’s a sign you’re growing.”

I’m moving to Vancouver on Friday to go all-in on a startup with some friends. I’ve felt a lot of fear this past week leading up to it.

Thursday. My team at Boston Dynamics took me out for drinks to celebrate my final day of work. Lots of friends showed up, and it reminded me of the love and meaning I felt at that company. I feared never finding that again.

Saturday. My partner and I threw a going-away party. Standing in the corner of my apartment, I could see 40 of our closest friends smiling and laughing together in the same room. I feared losing them to time and distance.

Today. I sit with my partner and her family at her sister’s graduation ceremony. When I’m in Vancouver, she’ll be in Los Angeles. I fear losing everything we’ve built together if I can’t find a way back to the United States in a few months.

Fear keeps telling me to stay in Boston. But it’s the same voice I heard three years ago, alone in my first apartment in Cambridge, sobbing into my hands, certain I’d made a mistake.

I hadn’t.

I wish I could put an arm around my younger self and describe to him all the blessings that were about to come his way. But since I can’t go back in time, I’ll put an arm around my present self instead.

I’ll remind myself that I’m moving to Vancouver to chase a decade-old dream of building a successful startup. I’ll remind myself that love isn’t constrained to a zip code—it can survive and deepen as long as I put in the effort. And I’ll remind myself that wherever I find fear, I find growth.

My compass is pointing in the right direction. Now it’s just a matter of moving forward.

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Tony Robbins

Quitting my job was weird.

I zoom-bombed my boss’s 1-on-1 with my boss’s boss. I began delivering the spiel I’d rehearsed, starting with, “I don’t know how to say this,” before going completely off script and blurting out, “I”M LEAVING BOSTON DYNAMICS.”

From there, I fumbled my way through all the bullet points I wanted to get across:

• “I’m grateful for everything you’ve done for me.”

• “I’m happy to work another 4 weeks if that’ll make for a smoother transition.”

• “I didn’t get poached. I don’t have anything else lined up. I just want to move to Vancouver for the summer to spend time with friends.”

• “After that, I plan to find some way to get another visa to live in Los Angeles, where my partner is moving.”

They asked if there’s anything they could do. Could they set up a working arrangement for me on the west coast? In Vancouver? Or L.A.?

God knows my parents and sister would want me to say yes—All three of them took turns calling me to tell me how stupid I was for giving up a US work visa at a time like this.

U.S.-Canada tensions are high. Trump slapped a 25% tariff on all Canadian imports, Air Canada bookings to the U.S. are already down double digits, and there’s a new deportation horror story every day.

Pair that with an economy wobbling on a knife‑edge and A.I. rattling software jobs, and bailing on a cushy gig feels like the opposite of a high‑IQ move.

But I still said no. Because the real reason I’m going to Vancouver isn’t just to spend time with friends—it’s to go all‑in on my startup with my co‑founders who live there.

History has a phrase for moves like this: burn the boats. In 1519 Hernán Cortés landed in Mexico, torched his fleet, and left his men no retreat. Since then it’s meant one thing: remove every escape route so the only way forward is through.

That conversation was four weeks ago. It’s Friday night, May 9 2025, and I just finished my last day at Boston Dynamics. The boats are ash.

As far as I’m concerned, the only path to reuniting with my partner in L.A. runs through Vancouver and this startup. Let’s get to work.

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I hoard mission-critical tasks and I don’t delegate enough. I've justified this by thinking, “I’m just doing the work that needs doing.” But that’s only half of the truth.

The other half? I’m scared.

I want to feel important. I want to feel needed. I want to feel safe. And building a team that doesn’t need me feels terrifying.

But I want to be a better leader—the kind that builds people up and helps them grow. The kind that shares critical tasks, delegates responsibility, and sets the team up to thrive, even without me.

Making that change stick isn't easy. I’ve learned that my most reliable strategy is finding selfish reasons to keep doing the right thing—even when it’s tough.

I don’t lie. Mostly because honesty matters deeply to me, but also because, selfishly, I'm terrified of ruining my reputation.

I try hard to be generous. Primarily because generosity feels good and meaningful—but also because, selfishly, I believe it comes back around.

Until recently, I didn’t have a selfish reason to be a truly selfless leader. Then I remembered something from a talk I hosted at Boston Dynamics.

I invited a respected leader to speak to a group of early-career engineers. Someone asked (as someone always does), “How do you get promoted?”

He replied:
"You need to do the job you want before you’re hired to do it. Eventually, higher ups will just make it official."

A fair pushback followed:
"But how can you do that if you’re already swamped with your current job?"

His answer stuck with me:
"If you don’t have time, you have to MAKE time. If you're an individual contributor, get so good at your job that you can finish it in half the time. And if you're a manager, make your team self-driving. Develop your people and systems to the point that neither need you. That's how you create space to work on other things."

That clicked for me.

I shouldn’t fear building a team that doesn’t need me. I should strive for it, selfishly, because it frees me to tackle bigger things—and ultimately become more valuable to the company.

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They consider the lifespan of their code, how often that code is likely to be revisited, and the performance/reliability needs of the systems for which that code applies.

Simply put: Software Engineering is Programming integrated over time.

For me, the transition from Programmer to Software Engineer wasn’t some watershed moment I can pinpoint, like a caterpillar turning into a butterfly. It was more like a Sapling growing into a tree—There’s a long period of time where you’re like, “Is that a sapling or a tree?” until eventually it grows so big that everyone agrees, “yeah, that’s a tree.” (Rough analogy, I know).

I spent a few years with a foot in both worlds, until recently when I noticed a few signs that I’d fully crossed over into “Software Engineer” territory:

1. “That’s a clever solution” started sounding like an insult.

When I was starting out, I lived for clever solutions. Every time I shaved a few milliseconds off a loop, I felt like I’d just split the atom. But after revisiting one too many Rube Goldberg functions I’d written months earlier, I realized “clever” often meant “cryptic”. These days, I aim for boring code—predictable, readable, and dull in the best way.

Like choosing an unsexy, fuel-efficient Toyota over a flashy, unreliable sports car. You won’t turn many heads, but it’s a smart move for your daily commute.

2. I started “shifting left”.

I used to treat security, extensibility and performance tuning as afterthoughts—stuff I’d deal with later if it became a problem. Then I had to clean up enough of my own messes to know that “later” always costs more. I learned to spend the extra hour upfront, triple-checking what I was shipping and welcoming thorough code reviews instead of dreading them.

I’d much rather take a few minutes washing dishes while I cook dinner than spend an hour chipping solidified grease off of a baking sheet the next morning.

3. I began treating cloud dashboards as “read-only”.

I’ve participated in one to many late-night firefighting sessions trying to recover the state of my prod environment to never again want to flip a switch or turn a knob in my cloud provider’s UI.

Nowadays, if it’s not in version control, I don’t trust it. Environment variables, Database migrations, resource configurations—they’re all committed now.

If it’s not reproducible, it’s not real. Terraform is your friend.

4. I stopped looking for perfect solutions.

Prepping for job interviews with LeetCode taught me that there’s a right answer to every problem. Working a real job taught me the opposite—there are no right answers, only acceptable trade-offs.

Every decision—every line of code—is a negotiation between speed, simplicity, scalability, and sanity. Now when I design something, I ask: "What’s the right trade-off for this moment?"

I’m not building for the highest score on LeetCode; I’m building for people—my colleagues and our users. And people need systems that work, not that impress.

5. I realized all my problems are human problems, not software problems.

I used to think bugs were my biggest enemy. Then I started leading projects both at work and at my startup, Wednesday Waffles. Now I know the hard part isn’t the code—it’s the collaboration.

AI can write my code for me, but it won’t stop me from merging an untested PR the night before launch if I want to. It won’t stop me from wasting time on low-priority tickets if that’s what I want to work on. It’s not going to make sure every engineer on my team understands how that new feature works if I don’t dedicate some meeting time to telling them.

That stuff’s on me.

Great engineering is about great systems, strong habits, and exceptional character. The hardest problems I face today aren’t technical. They’re social, emotional and organizational.

—

Programming is about getting things to work. Software engineering is about keeping them working. It’s about building in a way that respects time—yours, your teammates’, and your future selves’.

If you found yourself nodding along, congrats! You’ve graduated. Welcome to the long game.

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Beyond all that, he also takes ownership of every emergency situation. And that’s the quality I’ve grown to appreciate the most.

When something breaks and I have no clue how to fix it, I know I can always turn to my manager. He’ll calmly join me on my sinking ship, shouldering that big-ass spoon of his. Without a word, he’ll begin scooping out water. And he won’t stop until he’s bailed me out.

I’ve seldom had to wave the white flag like that and surrender a problem to him. But it’s a huge comfort to know that I always have the option to when things get hairy.

Except I don’t anymore… at least not at Wednesday Waffles: the startup I’m building outside of work, serving as CTO. There, I’m the guy with the shit-eating spoon, and it looks a whole lot smaller in my hands than it does in my manager’s.

The weight of that never really dawned on me until February 5, a couple of weeks out from our scheduled public launch date. For some undiagnosed reason, our system for syncing data between the the app and the remote database (a system only I was familiar with) was barely working. Users weren’t seeing each others’ posts and messages.

I called my CEO to talk through the problem and he assured me we’d fix it. But I saw doubt on his face for the very first time. I was doubtful too. I genuinely had no clue what was going wrong.

My Fight-Or-Flight instincts kicked in, and I wanted to choose Flight. I wanted to wave my white flag and have my manager swoop in to rescue me. And that’s when it hit me:

No one’s coming to bail me out.

It was a terrifying, hopeless feeling. But it was also clarifying. There was no wiser, more seasoned engineer with a spoon bigger than my own who could come save our sinking ship. For the first time, I understood what true ownership means — that when your Fight-Or-Flight instincts kick in, Flight isn’t one of your options.

So I chose to Fight instead. I embraced ownership of the problem. I asked myself, “What would my manager do?”, and I went from there. And a coffee and an all-nighter later, I found the hole and I patched it. I bailed myself out.

Being a founder is downright terrifying sometimes. And despite my deep-seated belief that we’re building something the world wants and needs, the startup survival stats are a reminder that there’s no guarantee that we’ll be paid back for all the fear and stress we’ve endured.

But I have to constantly remind myself that this business is not the asset I’m building. I am the asset I’m building. Every knockdown is an opportunity for me to stand up stronger, looking more like the man I wish to be than before I hit the mat.

So to any founder reading this: Know that no one’s coming to bail you out. And that’s gift. Grab a spoon.

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Do they describe me as chill, or intense? Agreeable, or rigid? Relaxed, or serious?

I try pretty hard to be the guy that’s easily satisfied. Satisfied with our plans for the evening, the topics we talk about, the people we’re with, the food we order, the movie we put on.

The easily-satisfied guy is very satisfying to be around. He wants to do whatever you want to do, and he thinks everything you say is funny and interesting.

Problem is…I’m not really that guy. Not to the people closest to me, at least. Ask my parents, or my sister, or any girl I’ve ever dated — I’m never satisfied.

Despite demonstrating zero potential throughout my teenage years, I always had a grand vision for how my life was going to go. All the things I’d accomplish. And it was easy to entertain those big dreams because I had all the time in the world to turn them into reality.

But then in my second year of university, I realized, “Oh shit, I’m way behind schedule.” By then I thought I’d already be rich, powerful and notorious. But I was 0 for 3.

So from then onwards, I cranked up the speed on the hedonic treadmill, breathlessly trying to catchup to that perfect vision of myself. And despite the fact that he keeps pulling further and further away into the distance, I still find myself chasing after him to this day.

I work, I write, I read, I lift weights, and I repeat. I don’t do much else. And the people closest to me — the ones that really know me — have learned that I’m not an easy person to be around when I’m not allowed to do those things.

Why write about this now? Because I’m working on a startup, Wednesday Waffles, and I get increasingly obsessed with it each week that passes. As that happens however, I let my co-founders — my best friends in the world — see more and more of the real me.

Sometimes I'm too intense and opinionated. Sometimes I push back on others’ ideas too aggressively. Sometimes I expect too much of myself or others. Sometimes I’m in a bad mood. Sometimes I’m not the guy they love.

The guilt and anxiety about this built up to a climax last night, where I had a heartbreaking dream that involved one of my best friends, Luke.

Cliff notes on Luke: he’s the best guy you'll ever meet. He’ll give you the shirt off his back floor (he doesn’t like wearing it anyways). His love and respect is worth a whole lot to me.

The dream was nothing crazy. Luke walked side-by-side with some nameless, faceless dream character while I walked alone a few paces ahead. At some point, I overheard him say, “Ray’s great. He works hard. But sometimes he doesn’t appreciate how hard you’re working. You learn to tune him out.”

That’s it. That’s the whole dream. And man, it hurt me.

One of our co-founders, Fahd, gave us some words of wisdom when we started working on this project back in November:

“We’re friends first. Don’t let this change that.”

My entire 20s, I’ve been like a hot-pocket fresh out the microwave — warm and inviting on the outside, murderously hot on the inside. Approach with caution.

I need to cool down. My fire burns hot, and I can’t let it burn the people I care about.

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His posture towards AI is one of the ways. He’s always trying out new AI tools, seeing if they can give us more leverage to move faster and grow bigger while keeping the team lean.

That’s the exact right thing to do, and if I were a rational human being, I’d see it that way.

The problem is — I’m not rational. I’m a practicing software engineer that has had to watch AI rapidly improve at doing the things he’s spent years getting good at. Plus it’s doing those things faster, cheaper, and sometimes even *deep sigh*… better.

Every now and then, my ego compels me to tune out the AI news for a while. I did recently. And last week, just as I’d given myself enough time to slowly climb out of my existential hole, my CEO spartan kicks me back in by sending me this delightful opinion piece about “vibe coding”.

The writing is beautiful. The message is terrifying.

TL;DR: the promise of AI coding agents — the kind that can build features and fix bugs without supervision — is close to being realized.

Already, Cursor helps our team write code. Copilot helps us review PRs. Sentry helps us fix bugs. It can’t be too long before these disparate systems are piecemealed together with minimal human-in-the-loop.

Now if you’re new to my newsletter, (1) thanks for doubling my audience, and (2) you should know that I’m an AI optimist. On balance, I think AI is going to significantly grow the market for skilled labor. But I also think it’s going to significantly change what qualifies as skilled labor.

I spent 5 years becoming “skilled” as a person who writes code. But AI will code better soon. So then — what does it mean to be a great engineer in the age of AI?

For over a year now, I’ve been feeling around in the dark for an answer to that question. My fingertips have grazed one a few times but could never grab hold.

Until last weekend, when I was kicking it with a friend who works at the same company as me. We watched March Madness and ate a 2.6-pound poutine/shawarma freak-show called “The Meltdown”.

We also talked lightly about a couple of co-workers. We gushed a lot about one and grumbled a little about another.

For the one we admired, we talked about his clear thinking. His approach to problem-solving. How his love of the game inspires the hell out of us. Ya, his code doesn’t take your breath away, but damn-near everything else does.

For the one we had feedback for, we talked about his tendency to get distracted. His lack of rigour when testing his work. And how it was hard to feel like you could rely on him to get his tasks done on schedule. Ya, he writes code as good as anyone, but he isn’t the easiest to collaborate with.

And that’s when I finally wrapped my arms around the answer I’d been grasping for: great engineering is about great process. And it always has been.

At my current startup, Wednesday Waffles, 2.5 part-time devs got an app on the App store and earned 3,000 users in 4 months. I’m really proud of that, but honestly we could have done it in 2 if we weren’t so busy stepping on each other’s toes in the codebase. Or merging PRs without discussing them first. Or prioritizing features over bugs. Or choosing the wrong thing to work on entirely.

At times it felt like anyone of us working alone could have moved faster than all of us combined, and it’s only now that I feel like we’re firing on all cylinders. Not because we’re vastly better Flutter developers than we were 4 months ago, but because we started to establish systems and decision making frameworks with the discipline to stick to them.

My problem isn’t that AI is devaluing my coding ability. My problem is that I ever thought my coding ability was what was valuable in the first place.

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He writes about startups — which is a topic I’m obviously very interested in — but I’d read this guy’s thoughts on the state of Myanmar if wrote an essay about it.

I just love his writing style. And I only really understood why when I came across this Casey Neistat quote:

❝

“The best steak houses serve their filet on a plate with nothing else. Shitty franchises cover theirs in sauce and other shit to distract you from the fact you’re eating dog food.”

The point being that good writers write short articles in simple language. It’s the bad writers with nothing meaty to say that cover up their small ideas with big words and other “steak sauce”.

One of the downsides of living in a post-ChatGPT world is that steak sauce is free and within reach at all times.

If you want to build a startup today, there’s nothing stopping you. ChatGPT 4o can write all your website copy. Stable Diffusion can churn out 50 social media graphics for you. Claude 3.7 can write thousands of lines of code for you.

On balance, I think this is a wonderful development for the world. But back when things took longer to execute, we thought much harder about how to execute and what to execute on.

We’re living in a golden age where it has never been easier to build something. But to paraphrase my favorite essayist, Paul Graham: you have to build something people want.

So let’s never lower our standards. Let’s always micromanage our AI tools. And let’s make sure that the “abundance” we create together is a pile of gold. Not a pile of garbage.

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I expected the road to get here to feel like a marathon.

It felt more like a Spartan Race.

We were constantly coming up against obstacles that challenged us in new ways and slowed us down tremendously. We ended every sprint tired, sweaty, covered in a mud and mildly disappointed that we didn’t cover more ground. And oh look, there’s another obstacle ahead. Terrific.

But hey, we launched an app in 3 months. We have 1,303 users. And last someone checked, we were sitting at #45 on the ‘Social Networking’ charts on the iOS App Store.

Let’s pat ourselves on the back.

Though I fought my team on it in the early stages, I have to admit that launching fast was a great idea. The rate of learning is faster. The pressure to improve is greater. And the thrill of seeing strangers use something you built is intoxicating.

But here’s my balanced recommendation to any product builders out there: launch fast, but roll out slow. By that I mean ramp up your user base slowly. Don’t “open the flood gates” to your entire wait list.

We had intended to launch our app last week, but had to push it back a week due to the App Store rejecting the version we submitted due to a couple of minor nits.

Thank god for that.

We rolled out that version to our small batch of external testers instead and the app had an unanticipated bug that made it completely unusable.

We then launched this past Tuesday to give users a day to get setup on the app in advance of Wednesday — the high-activity day for our app each week.

Thank god for that too.

Here are some of the things that immediately went wrong on Tuesday:

• Users’ data wasn’t syncing with the remote database due to another uncaught bug.

• Users couldn’t create accounts or login because we kept running out of Twilio credits faster than we were being auto-charged to replenish them.

• Speaking of Twilio, people in Norway couldn’t login because support for that geo-location was disabled by default.

• We got 429 and 544 rate-limiting errors in our database due to the number of people using the app all at once.

• Parsing of users’ phone numbers didn’t work as intended for certain country codes, so the app was unusable for people in Australia.

We patched all those holes as quick as we could and by the grace of god the app held together on Wednesday. But we really lucked out. If we had launched when we wanted to and fired all our sales & marketing bullets at once, we would have wasted a lot of great work that our Go To Market team has done over the past 3 months.

So launch fast, but roll out slow.

• Start with external testers that you know personally and will be patient with your bugs.

• Ramp up slowly, and see what bottlenecks you hit with your third-party services and back-end infrastructure.

• Spread out to different regions methodically. See how different folks are affected by query latency and security features of your third-party services.

…Or you could just stand in front of the thundering herd with your fingers crossed and pray your app holds up. Either way, you’re going to learn! And that’s all that really matters.

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But it’s also the hardest.

She doesn’t let me get away with bad habits or negative energy. We’re both super intentional about the life story we want to write for ourselves, and we’re constantly bumping elbows while doing so. It requires empathy and sacrifice to make it all gel.

I resented her for it early in our relationship. I questioned if she was the right person for me.

But I soon realized that I got exactly what I wanted all along. I wanted to be in a relationship that made me a better version of myself. I wanted to grow, and this what growth feels like.

My relationship with my co-founder & CEO is the same.

We’re working on a social app together, along with 4 other friends and, man, has it been fun. But it hasn’t come without its difficult moments, especially in the early stages when you’re still learning how to work with each other. Understanding each other’s strengths and weaknesses.

In the case of our CEO, he’s got a lot of strengths:

• He’s incredibly persuasive and rarely takes no for an answer.

• He’s got more ambition and “delusional optimism” than the remaining 5 of us combined.

• He has unparalleled speed and endurance, willing to sacrifice any semblance of work-life balance to move the ball forward.

But I’ve come to realize that all the reasons why you admire someone are also the reasons why they frustrate you. In the case of our CEO:

• His persuasiveness and indomitable will means it’s tough to nudge the ship in a different direction than the one he’s charted out.

• His ambition and optimism mean we’re constantly missing deadlines or cutting corners to meet them.

• His speed and endurance means the rest of us are panting just to keep up, often feeling tired and overwhelmed.

I resented him for all of these things when we first started working together. But once I got over myself, I realized that this isn’t all too different than my relationship with my girlfriend.

My CEO is giving us exactly what we all want and need: growth and our best chance at success.

• It’s great that he’s difficult to debate with. We’re all forced to improve at standing our ground and selling our arguments.

• It’s great that he sets goals too ambitious to meet on schedule. We’re playing out the age-old adage, “Shoot for the moon. Even if you miss, you’ll land among the stars.”

• It’s great that he’s forcing us to sprint on wobbly legs. That’s how we all build up the cardio to outpace everyone else.

In other words, he’s playing his role perfectly. As CTO, I have to learn to play mine. He sets the standard for speed and ambition. I need to set the standard for engineering excellence. That means sometimes being a countervailing force — ensuring corners are never cut in service of ambitious deadlines.

Now back to work…

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