I always struggled with double-entry accounting, even after I got an MBA. I could do it and mostly memorized my way through a lot of the jargon, but it wasn’t until I took a systems view to accounting that I really understood the mechanics of how things worked. …


I’m listening to what you’re saying. I’m sorry if it feels like I’m not. It’s just that my mind is racing. My mind is racing most of the time. It races harder when I try to stop it from racing.

It’s not an “inner monologue”. Inner monologues, I presume, are…


Originally published on somehowmanage.com, I’m publishing it here for posterity. There’s also a fun comment section on HackerNews around this article.

It’s a common narrative in tech to design products with the assumption that users are stupid and lazy. I think that is both disrespectful and wrong.

The idea is…


@nickmorrison via unsplash

I often write design documents even if no one will read them.

There are a lot of resources out there on how to write good design documents. …


@reidzura via Unsplashed

I see a common pattern with startups and teams I’ve advised or been a part of. I call it the Software Over-specification Death Spiral, or SODS for short.

It looks like this:

  1. Product Manager (or CEO, Engineering Manager, etc) drafts up some sort of specifications or requirements for a new…


https://unsplash.com/@f7photo

On many teams I’ve advised or been a part of, code is generally viewed as an asset. Only some code, the “bad code”, is considered technical debt. The highest-performing teams, however, viewed things differently. For them, all code is technical debt on some level.

Programming vs. Software Engineering

Software requires two broad classes of…


One Question

Learn how to tell who is a great worker, and which of your workers can be great leaders

Illustrations: Thomas Hedger

Growing teams need managers, and who better to manage a team than someone who is already part of one? While that may be true, picking the right person to become a team manager can be a lot harder than it looks. …


Credit: @hannynaibaho, Unsplashed

Over the past few weeks, after joining Monarch, I started writing code again. For context, save for a few side projects here and there, I haven’t written much code in the past two years (focusing instead on management, writing, and product).

The first thing that stood out: I am somewhat…


I left Quora about 5 months ago. Last week, I joined Monarch Money. I’d like to talk about why I made those decisions, and I hope this will be useful for others who are thinking through their careers.

Leaving Quora

Last year, my wife and I had a baby (little Ahmed Osman…


Photo Credit: Bruno Nascimento on Unsplash

If you are a founder or manager, one of the highest-leverage activities you can conduct is hiring. And in our competitive market, it’s just not something you can afford to screw up.

A common model for recruiting processes is the recruiting funnel. From a company’s perspective, if you look at…

Osman (Ozzie) Osman

Co-founder, Monarch Money. Ex-Quora, Google.

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