Matt Healey

Travel junkie. Payments and fintech @juspay. Prev: @amazon, @Mastercard. @TCDDublin, @TempleUniv alum - opinions my own

[JUSPAY @juspay]

Subscription businesses win with seamless payments.

@recurly is now live on @HyperSwitchIO.

One integration to unlock more payment methods, flexible routing, and scalable merchant onboarding and management.

[Matt Healey @Mheals16]

@AlfieJCarter Content

[Matt Healey @Mheals16]

@coldemailchris Playbook

[Matt Healey @Mheals16]

@peter I’ve gone down a rabbithole with obsidian. Has been great for knowledge management and long term projects but have found that Google tasks works better for tracking and follow ups

[Matt Healey @Mheals16]

@TechCrunch disrupt today and it’s easier to get seed funding than it is to get a water.

You can either wait in line for 5 minutes for a fountain or pay $7.88.

[Matt Healey @Mheals16]

@jamesplloyd Totally unrelated, but I was thinking we should plan an in person team summit in Europe in Nov / Dec

[Matt Healey @Mheals16]

@NWischoff Good luck! Just did the same two weeks ago (from SoFL). So far the family is loving it.

[Matt Healey @Mheals16]

@MiamiDadeCounty @GoMiamiDade @iflymia I spent 2.5 hours on 95 going home from Miami to Fort Lauderdale yesterday. Today, riding #ourcounty ‘s “transit system”, metro rail breaks down, waiting for train, no guidance or announcement. Now using pricey but reliable ride share. Still a 2+ hour commute.

You are a joke.

[Matt Healey @Mheals16]

Let’s go! 🚀🚀🚀

[Juspay Hyperswitch @HyperSwitchIO]

🚀 We’re thrilled to share that @HyperSwitchIO has surpassed 15k stars on @github

🌐 As an #opensource payments platform, we're proud to see our mission resonating worldwide

Github #Repo - https://t.co/LaYrZKtB7T

[Matt Healey @Mheals16]

Me trying to explain the difference between rules based transaction routing and dynamic, intelligent routing when someone brings up their "orchestration layer."

[Matt Healey @Mheals16]

@peter I’m with you. My daughter figured out how to use Alexa and my Spotify algorithm has never recovered since.

[Matt Healey @Mheals16]

@peter Love this! Something I’ve always thought of doing but put off. Thanks for the motivation!

[Matt Healey @Mheals16]

@jsfranklin221 @stripe Congrats, they’re lucky to have you!

[Matt Healey @Mheals16]

@regulatorynerd Agreed. Might also be a good way to incentivize greater fee transparency between networks and channel partners (and ultimately end merchants)

[Ashley Mayer @ashleymayer]

One of the most interesting metrics of company culture is what I call the "work to do the work." How much time is spent on information gathering, stakeholder alignment and decision making, and how much is spent on actually doing the thing. An early startup's biggest advantage is that alignment tends be easy, since you have a small team all working on the same product, a founder who is the ultimate decision maker, and a necessary bias to action (maybe a 1:10 WTDTW:W ratio). As you scale, this ratio invariably shifts: bigger teams, more hierarchy, more complexity, more feedback to inform future decisions. Good processes should be in service of helping teams make and communicate well-informed decisions so they can still spend the bulk of their time actually moving things forward.

The problem with a high WTDTW ratio isn't just that it slows teams and companies way down, but that it changes the incentives of an organization. In a company with a 10:1 ratio, for example, employees are rewarded for their ability to navigate and influence the organization, rather than producing results. I distinctly remember a moment in my career when I realized, with horror, that I was pouring the vast majority of my creative energy into solving problems in the WTDTW realm (and getting real personal satisfaction from playing that role well)...but I was exhausted by the time we actually got to execute. And it's a dangerous trap, especially for executives, to think that all the "strategy" is in the WTDTW bucket, because the creativity, iteration and debate that goes into actually bringing something to life is where the magic happens, whatever your company's size. 🪄

[Matt Healey @Mheals16]

I felt this in my bones 🙁. That’s the challenge of working at large, mature tech orgs. Often, the messiness is the the goal for some of the leaders who are in a position to make the necessary changes.

[Shreyas Doshi @shreyas]

It is easy to make fun of PMs & engineers in big companies who are just launching features, moving pixels around, and are focused on “outputs over outcomes”, but you must understand that some environments are so messed up that a launch (really _any_ launch) is by itself a huge achievement requiring superhuman effort.

Contrary to what people might like to believe on Twitter, these PMs & engineers know that this is not ideal. They know they should be doing things differently.

But the mess around them is just overwhelming. It would be impossible for anyone at the level of an Individual Contributor (IC) or a first-level manager to fix the mess.

While mindlessly scrolling through your Twitter feed, you might think you can fix it.

You ran & exited a highly successful startup
You declined the Thiel Fellowship at 16
You scored 1600 on your SAT
You were a silver medalist at the IMO
You graduated at the top of your class at MIT
You were 30 under 30, thrice

So you are quite certain you can fix Google, you can fix Meta. Heck, you think you can fix both Salesforce & Adobe before it’s time for lunch.

But you can’t. You could be Steve Jobs, you might be Elon Musk. But as an IC or a first-level manager, you won’t be able to fix any of them. Guaranteed.

Plus, in some cases, it is actually just fine to focus on outputs. This is when your product has already succeeded, you are benefitting immensely from Legacy Momentum. With the success came this mess. So this now means that the locally optimal solution as an ambitious and energetic IC is to just launch a thing. Something. Anything.

Ultimately, the onus of fixing the mess is on the leaders (usually Directors & above). They *can* actually fix it.

But some think this total mess is a necessary part of their scale (wrong).

Some are fine with the mess because it benefits their personal career agenda (bad).

Others just don’t know how to fix (very common).

Most leaders try introducing new, better Process to solve this problem. Not all Process is bad, and sometimes you can fix certain issues quickly with Process. But, while Process can be a good temporary band-aid for execution, it is not a permanent fix for deep organizational wounds.

You see, most execution problems are not actually execution problems at all. They are:
1) Strategy problems, or
2) Culture problems, or
3) Interpersonal problems

So the right approach for solving the mess is to have the judgment to debug the real problem, have the courage to formulate a solution that might involve ruffling some feathers, and then get the mandate to go solve it properly.

But unfortunately, this is hard work that requires
A) tremendous skill and
B) trust from fellow leaders & execs

A is rare and B is often in low supply because of the short-term pressure of OKRs & targets and political agendas.

At the right levels, with the right people, it can be solved, but it is by no means easy. And so the problem persists in every large company — at least until the founder returns or a unicorn non-founder CEO like Satya Nadella manages to turn things around.

And until then, the only thing you can do while you are still an IC at this company is put your head down and ship something. Anything.

[More Perfect Union @MorePerfectUS]

BREAKING: The Biden administration is ending bank overdraft fees as we know them.

Under a new Consumer Financial Protection Bureau rule, overdraft fees at large banks will be strictly regulated and capped as low as $3. Low-income Americans will save billions.

[Matt Healey @Mheals16]

This sounds like a dream!

[Dan Hockenmaier @danhockenmaier]

The way that Jensen Huang runs Nvidia is wild:

40 direct reports, no 1:1s
- Believes that the flattest org is the most empowering one, and that starts with the top layer
- Does not conduct 1:1s - everything happens in a group setting
- Does not give career advice - "None of my management team is coming to me for career advice - they already made it, they're doing great"

No status reports, instead he "stochastically samples the system"
- Doesn't use status updates because he believes they are too refined by the time they get to him. They are not ground truth anymore.
- Instead, anyone in the company can email him their "top five things" with whatever is top of mind, and he will read it
- Estimates he reads 100 of these everyone morning

Everyone has all the context, all the time
- No meetings with just VPs or just Directors - anyone can join and contribute
- "If you have a strategic direction, why tell just one person?"
- "If there is something I don't like, I just say it publicly"
- "I do a lot of reasoning out loud"

No formal planning cycles
- No 5 year plan, no 1 year plan
- Always re-evaluating based on changing business and market conditions (helpful when AI is developing at the pace that it is)

This org is optimized for (1) attracting amazing people, (2) keeping the team as small as it can be, and (3) allowing information to travel as quickly as possible

[elle ✨ @heyellehogan]

I’m at the airport reading, and a man in his ~60s walks by me and says: “Great book. Wish I had it earlier.”

So I ask, “Really? Why?”

That sparked a convo about how he went from Harvard MBA to investment banking in NYC… to an existential crisis at 35 where he lost himself, gave it all up, found himself, met his wife, and built multiple business.

What stuck with me the most is how he talked about his wife. He just LIT up.

“If you think I’ve had an interesting life, you should meet my wife! She’d blow you away. She blows everyone away. She’s the most impressive woman I’ve ever met. She’s my linchpin.”

Me: “What advice would you give for choosing a life partner?”

Him: “If you have a big vision and want a big life, you need someone who knocks your socks off. It’s gotta feel like winning the lottery. This person is your #1 advice giver. Your lifelong backup. Your companion for thousands of meals, events, problems. You need someone better than you in a lot of ways. Whose mind and heart amaze you. I wake up every day like, ‘How on earth did I land her?’ She says the same thing. That’s when you know.”

Then he showed me like 300 pictures of them and their kids on vacation around the world.

Couple goals. 🥹