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The Best Hidden Features of VLC

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The Best Hidden Features of VLC

VLC is easily one of our favorite media players (and yours too). However, it's not just a one-trick pony. Under the surface, there's a wide range of features that you might not have known it could do.

Download YouTube Videos

The Best Hidden Features of VLC

We've discussed plenty of ways to download YouTube videos before. However, you have one option already installed on your computer. VLC lets you play and download YouTube videos right from its desktop interface. Here's how:

  1. Find a video on YouTube—like this one—and copy the URL from the address bar.
  2. In VLC, head to Media > Open Network Stream.
  3. Paste the YouTube link in the box and click Play.
  4. Under Tools, click Codec Information.
  5. In the box that says Location, right-click the block of text and click Select All. Copy this text to your clipboard.
  6. Go back to your browser and paste the link in the address bar. This will open the source file directly on YouTube's servers.
  7. Right-click the video as it plays and select Save Video As.

You can also record clips from YouTube videos as they're streaming in VLC by pressing the red Record button in the player itself. This isn't as direct of a rip, but it's handy if you need to grab a particular clip out of a long video.

Record Your Desktop

The Best Hidden Features of VLC

Desktop recording software ranges from poor quality and free to incredibly powerful and expensive. VLC manages to strike a balance between both. In our tests, it wasn't powerful enough to, say, screen record a movie. However, for showing someone a problem you're having on a computer or providing quick instructions on how to perform a task, it's more than enough.

  1. Under Media, click "Open Capture Device."
  2. Click the "Capture Mode" dropdown and select "Desktop."
  3. Modify the frame rate. 15 f/s will probably be good enough for desktop recording, though 30 may be required for more fast-paced movement.
  4. Click the dropdown arrow next to "Play" and select "Convert."
  5. In the "Profile" dropdown, choose MP4.
    1. At this step, you can click the tool icon to modify the settings of this profile. Here you can modify things like resolution or bitrate. We'll use the default settings for now, but you can come back here later if you need to tweak the final product.
  6. In the Destination box, choose a location to place the finished file.
  7. Click Start.

Once you click Start, VLC will stream a feed of your desktop into itself behind the scenes. Let it run while you record your workspace. When you're done, you can click the stop buton in the player controls to end recording.

Convert Video Files

The Best Hidden Features of VLC

VLC also has a pretty decent video converter built in. If you have a file that needs to be in a different format to upload or play somewhere, you may not need to download an entirely different application just to convert it. Here's how to convert between one file and another:

  1. Under Media, click "Convert/Save."
  2. Add the file you want to convert in the File Selection section.
  3. Click "Convert/Save."
  4. In the Settings section, choose the type of file you want to convert the file into under Profile.
  5. Give the file a name and location under Destination.
  6. Click Start.

The converted video file will be deposited in the target location. VLC certainly isn't a replacement for a more robust application like Handbrake. However, for simple jobs, it's probably the only video converter most people have on their machines.

Record Your Webcam

The Best Hidden Features of VLC

Your webcam may or may not have come with software to take pictures and record videos. However, chances are VLC has some advantages over both. Not only can you choose several different types of formats to record to, you can also tweak a number of fine grain settings if needed. This is helpful for making YouTube videos or recording video messages to send to friends or relatives. Here's how to record video from your webcam:

  1. Under Media, click Open Capture Device.
  2. In the "Capture mode" drop down, select DirectShow.
  3. For "Video device name" choose your webcam.
  4. For "Audio device name" choose your microphone.
  5. Click "Advanced options."
    1. If you want to use the software that came with your device to control input settings, choose "Device properties."
    2. Otherwise, enter a value for "Video input frame rate." 30 is a good rule of thumb for smooth video, though you can use less if you're not concerned about quality.
    3. Click Okay.

At this point, you have two options. You can click Play to play live video through VLC and record segments as needed by pressing the red Record button. Alternatively, you can choose "Convert/Save" from the dropdown and select where you would like the recorded file to go. Both methods have their advantages. The former allows you to preview your video and take clips in short bursts. However, this method requires headphones, as it can create a feedback loop. It also may cause a more sluggish recording on slower computers.

Using the Convert/Save method avoids the feedback problem but it also doesn't provide you much information on what you're looking at or when you're done recording. You can stop the recording by pressing Stop in the player, but there's no indicator that you are still recording at the time.

Subscribe to Podcasts

The Best Hidden Features of VLC

You might not think of VLC as a podcast manager, but if you use it regularly, it's actually pretty handy. To add a podcast, you'll need the RSS feed of the show. As an example, we'll use Lifehacker alum Adam Dachis' Supercharged podcast here. The RSS link will probably look something like this:

Once you've found the RSS feed for the podcast you want to keep up with, follow these steps:

  1. In VLC's sidebar, scroll down until you see Podcasts.
  2. Hover your mouse over Podcasts and click the plus sign on the right.
  3. Paste the RSS feed URL of the show you want to add.
  4. Click OK.

Now, your podcast of choice will appear in the Podcasts sidebar section. Click on the name of a show and you'll see a list of available episodes. Double click on any one of them to start streaming.

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21 days ago
Did not know VLC had all these features.
24 days ago
Handy. I had no idea VLC could be a screencap app.
Sioux City, Iowa
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How To Make A Pumpkin Look Like Somebody

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(No Artistic Talent Required!)

It’s Halloween! This holiday is second only to Christmas in terms of the amount spent per year on decorations (in the USA, anyway). But for some of us, there is more to it than cheap, mass-produced rubber spiders, talking skeletons, and so on. It’s yet another excuse to be creative, in a geeky way.

So let’s carve pumpkins! When I was a wee lad, my brother and I took black markers and made an outline of what we wanted on our pumpkins, then dear old dad would cut them with a sharp knife (which we, of course, weren’t allowed to play with). Think triangular eyes, a simple nose, and a snaggletoothed mouth. Now that I am older, I find this is way too efficient, and much more time can be frittered away with this exercise…

Basic Carving Outline

(Apologies in advance for saying so many things you already know… or just skip this section.)

  1. Get pumpkins. You can grow them, get them at the store, or visit the kitschy farm down the road. Look for ones you can easily spread your hand across, they are the right size for single page (8 ½ x 11) paper patterns.
  2. Get a paper pattern. They come in books, but more sophisticated ones can be found online ( is a favorite of mine), and printed out (laser printouts are preferred, as they are nearly impervious to pumpkin juice).
  3. Tape the pattern to the pumpkin (This means you don’t actually need artistic talent. Just trace it!). This is easier if you have cut some notches in the paper so it bends around the pumpkin. I say use lots of tape. Cover every bit of the paper with tape. That way, if it gets pumpkin juice on it, it won’t fall apart.
  4. Cut the top off. Angle it, so the top doesn’t fall in. (If you cut it straight up and down, this will happen quickly as the pumpkin ages.) Alternatively, some experts prefer cutting the bottom out of the pumpkin instead of the top. This may make the pumpkin last longer, especially if it is out in the weather. But then you may need a chimney. Either way, I leave a notch so the original orientation of the lid can be quickly reestablished.
  5. Scrape the guts out. Scrape the part where the pattern is applied extra hard, if you are going with a three-level pattern (explained next), so the light shines through nicely. Keep some seeds to bake and eat, if you are into that (I am not).
  6. Cut the pattern. Unless you are being really fancy, this can be done in three levels:
    • Skin left on. This is of course the darkest.
    • Skin peeled off. Much more light shines though.
    • Cut all the way through. This is the lightest.

There are many tools for the job. For cutting through, knives really can’t get a high level of detail compared to the special-purpose pumpkin saws they sell these days. (Cut as perpendicular to the surface of the pumpkin as possible so the piece is easily extracted. If the piece doesn’t pop out easily, cut it into bits.)

For scraping the skin, I haven’t found anything better than a pocket knife. Just cut the edge around the area (this makes nice clean lines), then if the area is small/thin pick it out with the knife point, or if it is large, cut it into pieces to pick out. (Cutting up and down the grain of the pumpkin is easiest, if it is convenient given the shape of the area to scrape.) They also sell tools with little loops on the ends as part of store-bought kits, but I prefer to live dangerously and use my trusty knife.

The order in which the areas are cut out has a profound effect on how hard it is to execute the design without breaking anything. This is hard to pin down in words, but as you don’t want to paint yourself into a corner, you also don’t want to be cutting/scraping anything that has very little structural support. Starting with the smallest details is never a bad idea.

  1. Take the pattern and tape off.
  2. Cut air holes in the back if the pattern doesn’t involve many areas that are cut through.
  3. Put a candle in, light it. Pumpkins are >90% water, so putting them on your cement steps with real fiery candles in doesn’t sound that dangerous.
  4. Take pictures of your handiwork! (See the last section.)

Additional Steps

  • Invite some friends over, and have your sister-in-law with the Johnson and Wales degree make the snacks.
  • Add beer and/or wine, to taste.
  • There are also tailor-made power saws (reciprocating, not circular) available, and these are quite helpful for designs with lots of long cuts. Some people also use power tools to scrape the skin, such as a Dremel tool. This works, but I advise against combining this with #1, or #2 in particular.

How To Make Your Own Patterns

Making your own patterns is a great way to get geek technology involved in what otherwise would be a nice, earthy-crunchy hobby. This is not that hard, but you will impress people who don’t think of these things.

Get a picture using a digital camera, Google image search, or whatever. This could be easy, or not. But you won’t know for sure until later steps. Here’s what I used this year:

Crop the picture. Convert it to black and white. (I used to use PhotoShop when I had an employer that could justify the expense of having a legit copy. Now I use the GIMP.) If you look closely at the hair, you can see that I touched it up a little, in preparation for the next step…

Convert the image to three levels. I use black for skin, gray for scraped, and white for cut through. This gives an impression of the final result, but generally uses more precious toner than doing it the other way ’round. This year I just adjusted the color curve in GIMP, but I am sure I have used other means in the past.

This should result in a 3-level image:

There are a few things to note here. Obviously it is tricky to pick the levels to get something that is true to the original image. However, you also have to be aware that gravity will claim anything that is completely surrounded by a cut-out (white area). You can (in order of preference) either just erase these (in the image above they are tiny), keep fussing with the levels until there aren’t any, add supports to them, or go back to step 1 (pick a new image).

Cut the pumpkin. It may look like complete crap in the daylight:

Fear not! in the dark, things look better than you’d think, given the number of mistakes you may or may not have made in the cutting process:

Get addicted, and do more pumpkins next year. Here are a few samples from our parties. (See if you can spot the shameless plugs for our company.)

Taking Good Pictures

So even if your pumpkin doesn’t look that good, you may be able to salvage it by creative use of your digital camera.

  • Use full manual mode. That way you can adjust the picture by trial and error, and keep the most appealing one.
  • Unless you can hold still for 15 seconds, a tripod is a must.
  • Stop the camera down. (This may not apply to your camera, but the one I got for a mere $150, 6 long years ago works best stopped down, as it blurs less. I realize that this is counter-intuitive since there isn’t a lot of need for depth of field, and the light is low. But that’s what I do.)
  • Same goes for film speed. Use the slowest one, as you get the least noise in the dark areas. Even though this is counter-intuitive in low light settings.
  • Then adjust the exposure time to make it look good. Take a few. Use 2 seconds, 4, 6, 8, 10, 15, and then keep whatever looks best. Usually, it takes a lot of work to get a digital photo to look almost as good as real life, but with pumpkins, it is pretty easy to make things look even better than reality, just pick the right exposure.
  • The first photo shows approximately what the pumpkin looks like in real life (you will have to trust me on this). The second shows the exposure I liked the best, which soaked for a bit longer.


I’d like to thank my wife for starting this tradition, and cleaning the house before every party. And all our friends, for their contributions to our growing gallery.

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21 days ago
Not what I expected to see on an engineering blog in the HP family.
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Why Pennsylvanians should vote for Tom Wolf

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Though I was born and raised in Pennsylvania, I haven't lived there for years. So why should anybody in the state listen to me about who to vote for as their governor? Because, this time, I can personally attest to the character of the best man for the job.

Tom Wolf is an outstanding candidate. Since I'm someone who cares about education and job creation and women's health and opportunity for workers and criminal justice reform, workers, it's easy to see that Tom's platform aligns with my political positions. But I want to offer an insight into talk about something deeper.

My parents came from the most humble roots. Take my dad — born while India was still under British rule, he grew up with no running water or electricity, with only a grade school that could barely keep up with his voracious mind. And all of this undergirded by unreliable nutrition due to erratic farm crops destabilized by colonial policies that resulted in one of the worst and deadliest famines in human history.

Yet despite all this adversity, my father persevered, coming to the United States, getting his PhD, and with my mother, becoming a leader in both their community and their careers while providing their community and industry while providing two kids with nearly boundless opportunity.

Tom Wolf in Orissa

What does this classic American story have to do with Tom Wolf? Well, in that poor, fragile region where my parents dad grew up, one of the first interactions that many in the area ever had with a westerner was with Tom Wolf, who chose to serve in the area as a Peace Corps volunteer. volunteer.

Tom's work focused on stabilizing and growing agriculture in western Orissa, the Indian state my family is from. Here is a man who was born with all the privilege and opportunity that America could afford a man, and who chose to serve those who had the least.

This is what leadership is, enabling people to live their best lives on their own terms by working alongside them with respect.My parents succeeded because they

Now, my father succeeded because he worked hard, and they were was already on the path to an amazing life when Tom's work began. But countless others had their prospects permanently improved because someone who had everything was sincerely interested in helping those who didn't have nearly as much.

Leaders must be curious

Tom Wolf And Tom had an honest respect and intellectual curiosity for the culture that he was engaging. As is the custom, my parents' wedding in India involved almost the entire population of their respective hometowns, with multiple days of celebrations and events. The only American, the only white guy, the only person of such privilege who was curious and committed sincere enough to be present at such an event was Tom Wolf.

From that bond of witnessing their marriage to decades later, in my youth in Pennsylvania, Tom Wolf and my parents stayed true friends. As my mother's career succeeded she still made time to host legendarily delicious and decadent multi-course dinners of Indian cuisine at home, and I can remember a number of times when Tom Wolf would show up and dig into the food with the gusto of a native.

Now, it's been decades since I've seen Tom Wolf. I was just a kid when we interacted, so I can't say that I know the man today, man, or that he'd even remember me. But I know how fondly my parents speak of a friend who knew them in their lives before they came to America, a friend who cheered them on as they cheered him on, over years decades as they all went on to become accomplished community members and entrepreneurs in Pennsylvania, and loving parents at home.

Around elections, everybody trots out clichés like "character matters", but what do these phrases really mean? I think they must be a way of asking, "What did this person do with their time on the Earth back when the cameras weren't looking? How did a person use their privileges and good fortune to serve others?" In short, what is the sincere nature of a person who wants us to give them power?

These are the ways to measure a leader. Many people can say the right things about a slate of political positions, and mean it. But if we're going to give someone the power and the great privilege of serving as a leader, then we should expect that they've proven their character.

Tom Wolf has proven his character. He earned the respect of my parents a world away, nearly half a century ago, by honestly and sincerely engaging with people he'd never known, and simply being of service. That's what leadership is, and that's why as someone who was born and raised in Pennsylvania, who still counts many friends in the state, I ask all of you to elect Tom Wolf today.

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24 days ago
This is an endorsement.
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Coworkers Should Be Like Neighbors, Not Like Family

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All companies want engaged employees. After all, people who are engaged put in effort that goes above and beyond the minimum that’s required to complete a task. They are less likely to look for another job. And they project positive energy, which improves the mood of other employees and customers.

One way to increase engagement is to foster a “neighbor” relationship.

Research on types of relationships suggests that we can break the world up into several kinds of relationships. I refer to the three that are particularly important in the context of business as strangers, family, and neighbors.

Strangers are people with whom we do not have a close connection; if we need their help, we pay them to provide it. Families are people with whom we have a close bond and for whom we do whatever is needed, often expecting nothing in return. In between strangers and family are neighbors — people with whom we have a reasonably close relationship, who offer us help, and expect help in return.

It’s not good to have a workplace that consists primarily of strangers, because every interaction becomes a fee-for-service transaction and strangers are not motivated to go above and beyond the specific tasks presented to help the organization fulfill its goals. Moreover, the social environment in a workplace full of strangers does not energize employees to want to come to work.

Likewise, it’s dangerous for most organizations to function as a family, because not all employees will pull their own weight. It’s an inefficient and demoralizing way to work.

But with our neighbors, we try to balance what we do for them and what we get from them over time. We construct covenants in which everyone shares a common vision and agrees to do what they can to work toward these common interests.

In a healthy workplace, neighbor-employees work hard, secure in the knowledge that the organization is looking out for them. The organization succeeds because its employees put in a reasonable amount of extra time and effort for each other.

There are several ways to promote a neighborhood in the workplace. At the core of each of these techniques is a demonstration that the organization has a broader vested interest in its employees. This reassurance is particularly important for publicly traded companies that are normally focused on improving earnings each quarter.

One way to support neighborhoods is training. Many companies provide extensive training opportunities for their employees, which give them a chance to develop both work-related and personal skills. This demonstrates that the organization is interested in the employees’ long-term best interests. Any investment in those training opportunities pales in comparison to the cost of replacing people who leave the company.

A second way to promote a neighborhood is to provide regular opportunities for employees to engage directly with higher-ups. Being a part of the neighborhood requires a feeling that the organization knows who you are and cares not just about people in general, about you in particular. Without some points of contact to the upper management of the company, a business unit might become a neighborhood, but that neighborhood may feel disconnected from the rest of the organization.

A third component of the neighborhood is that it needs to have a shared purpose. Residential neighbors are bound together by the desire to create a community that benefits the people who live there. Similarly, companies need a shared vision that transcends the individuals. For example, at the University of Texas (where I work), I have worked with our operational staff to help the various units (like construction, emergency services, and power) to reconnect with the mission of the university in order to make those units feel like a more central part of the neighborhood.

Finally, it’s important for all managers to look for signs that an organization is slipping from a neighborhood to a group of strangers. The biggest signal that a neighborhood is eroding is when employees start finding reasons not to support broader initiatives within the organization because of the narrower job that they have been assigned. They may give excuses for focusing on their particular job instead of what the larger organization needs. When this happens managers need to return to the above approaches, demonstrating that the organization cares about them and remind them of their connection to the broader mission.

Although it does require effort and resources to maintain a neighborhood, the investment is quickly repaid.

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25 days ago
I like the neighbor metaphor better than the family metaphor for sure.
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Dan Frommer on CurrentC, and Why Retailers Are Unlikely Devise a System Customers Will Like


Dan Frommer:

While Apple Pay is designed to make payments as easy as possible — by riding on existing payments infrastructure, with security and privacy in mind — using CurrentC actually looks harder than typical payment techniques. Because it’s designed to skirt the existing credit-card infrastructure, CurrentC’s current version only supports payments via checking accounts and certain store cards. And it comes with a questionable privacy requirement: To “confirm your identity,” CurrentC demands both your driver’s license number and social security number.

When it comes to actually paying, the system gets even more cumbersome. CurrentC describes the process on its support site: You need to select a “Pay with CurrentC” option on the register, activate your phone, open the CurrentC app, enter a four-digit passcode, press the “Pay” button, “either scan the Secure Paycode that the cashier presents (default) or press the Show button at the bottom of your screen to allow the cashier to scan your Secure Paycode,” select the account you want to pay with, and then press a “Pay Now” button.

John Moltz quips:

Not only will I never use this system, I will strangle the first person I’m behind in a checkout line who tries to use it.

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28 days ago
The more I hear about CurrentC, the worse it sounds.
27 days ago
Assymptotically approaching a black hole of stupid ideas.
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1 public comment
28 days ago
Cumbersome, insecure and little buyer protection. Might be great for retailers, but I see practically no customer incentive to use it.
Bellevue, WA

#define CTO


I joined Stripe as an engineer in 2010. I began by working on the backend infrastructure: designing the server architecture, creating our credit card vault, and producing internal abstractions to make people’s jobs easier. I loved writing code, but I also spent a bunch of time on other things: figuring out our recruiting program, shaping the culture, or making our first T-shirts (which have been banned since we hired our first designer). I wasn’t doing these things particularly because I preferred them to coding: instead, I had a very strong vision of the environment I wanted to be a part of, and I was willing to go out of my way to make it exist.

As time went on, I accumulated more and more responsibilities which were not strictly writing code. As Nelson Elhage liked to put it, my job became full-time “early employee”. My days were filled with writing cultural guides, acclimatizing new people, running our recruiting program, and the like. I’d often think it was time to give up on coding altogether, but I somehow always found a way back to it.

About a year and half ago, we officially declared me CTO. It was really just putting a word to what I was already doing — the most common reaction was “wait, I assumed Greg was CTO already”. This post is the story of what happened next: finding a partner to build our engineering team with, and figuring out my role as the organization changed.

Around last summer, to keep up with the needs of our engineering team, I started doing 1:1s with everyone. I would stack them all on a Tuesday, and be completely burned out by the end of the day. By the time I was recharged and productive again, it’d be next Tuesday, and it’d be time to do it all over again.

Through this time, I knew I was faced with a choice: the technical route or the people route. I’ve never found anything I loved more than writing code, but at the same time I knew we had a responsibility as an organization to support the amazing people we’d hired. I was talking with one of my friends, the CTO at another company, who told me about how transformative hiring a VP Engineering had been for him. I’d heard of VPs Engineering before, but I’d never really considered that you could actively go and get one. So I resolved to find a VP Engineering, and convinced our CEO and others internally that this was a good idea.

Internally, no one wanted the role. We’d hired primarily great individual contributors, people who like me wanted to be building, and correspondingly hadn’t hired anyone who really wanted to be managing the entire group. So it was clear we were going to have to hire from the outside.

Over the prior year and half, I’d been meeting with a bunch of professional managers to ask them for advice. A very small number had really stuck out to me as the kind of people who, if they were ever available, I’d work with in a heartbeat. But timing never works out that way, so I prepared to spin up a recruiting firm.

And not to be too anticlimactic, but during that time one of those managers, Marc Hedlund, coincidentally became available. I talked to everyone on the team to talk about the idea of hiring a VP Engineering generally, and this candidate particularly, and then all 25 engineers sat down to talk about it as a group. We didn’t know exactly what the role would be, though we knew one thing it would entail: lots of 1:1s (primarily with engineers today, and primarily with managers as we scaled). So we figured that the best strategy was to focus on whether the candidate would be great at 1:1s, and then once he was here figure out the rest of the role together.

We then set up interviews with Marc: four days of back-to-back 1:1 or 1:2 meetings with everyone on the team from 10a-6p, as well as a talk to the whole company. I asked him several times whether this grueling back-to-back interviewing was actually ok: it seemed like the kind of thing that would require superhuman stamina. But he reassured me that yes, this was totally fine. And sure enough, he was great.

I also talked with a bunch of people who had worked with him previously, some of whom were references given to me by Marc and some of whom were backchannel. There were very clear themes in the feedback: “he’s been an amazing influence and mentor for me”, “I still keep in touch”, “I’d love to work with him again”. I very much wanted to be working with someone who others say that about.

Finally, just as important was figuring out how well Marc and I would work together personally. Between the two of us, we’d have responsibility for growing and shaping the engineering team, and we’d be in trouble if we weren’t acting in concert. We spent a bunch of time together, talking about some of the problems Stripe was facing, Marc’s view on management and leadership, and the like.

I asked him, “How would we resolve disagreements?” His answer: “Well, we’d talk about it, like we’re doing now. The ideal setup is one in which we trust each other to work to make engineering better, and if either one of us has significant concerns about an approach, we talk about it, and if those concerns remain then hold off on that solution.”

Later, when I asked him what he thought about the process, his answer was “you folks have clearly never hired a manager before”. He took on the task of designing our management interviews. Ironically, I’d had much the same reaction to my own interview process back in the day, which had motivated me to work on our engineering interview design.

So we brought Marc in. In advance of his start, I added him to the email lists and added him on IM. We spent many hours talking over what was going on at the company, how to approach particular issues, reviewing email drafts for each other, and the like.

Once he started, I immediately transitioned all the 1:1s over to him. He also told me that I should feel free to send him any other stuff that I wanted off my plate (music to my ears given how overwhelmed I was at the time). Recruiting in particular was one that he suggested could make sense. I was actually kind of surprised: I’d never really known where recruiting fit, and had never really expected to be able to stop running our program. But it turns out that recruiting is typically part of the VP Engineering’s role. In fact, I slowly realized that the role I’d developed organically actually was almost entirely the usual VP Engineering role.

As time went on, one important shift was making sure that when people would take problems or issues to Marc rather me. The best thing I did on this front was take a vacation (my first ever) to Hawaii, and then holed myself up with a few engineers building CTF3. I also transitioned more and more responsibilities: because Marc was now talking to so many people, he was much better situated to know the problems any given group was facing, or how an organizational change was playing out.

The integration for any new executive is never smooth. There are false starts, and the rockiness of any change — in some places the culture needs to change to match the executive, and in others the executive needs to change to match the culture. I suffered from something I think a lot of engineers do, which is having trouble distinguishing “not the way I’d do it” from “bad”. Marc would run recruiting, or hold the team lead meetings, or communicate, in a very different way from me, and it took a while for me to really grok that everything was still ok.

The best advice I’ve gotten here is you have two traditional choices for how to delegate: you either delegate completely (and maybe you define some principles, but otherwise you have to leave the execution alone), or you stay involved in all the details. The latter model can work — think Mark Zuckerberg’s involvement in product — but you really only get to do it for one area. (There’s also a non-traditional approach, which is to train some people to be really good at simulating you, and have them run the delegated function. This may work but is not necessarily healthy.) But universally, “sparse micromanagement” (the best term I’ve heard for jumping in to some random issue, overturning all the decisions, and then disappearing) is the worst.

The way Marc and I worked through this was actually pretty simple: we spent way more time together. We started doing two hour-long 1:1s a week, one on Monday and one on Friday. There would be times when we wouldn’t have a ton to say, but it was incredibly important that we’d spend a bunch of time saying what we were worried about, what we were working on, where things are going. As a result, I went from having a bunch of issues where I didn’t know how Marc would react, to never being more than a few days from finding out, to eventually having a good enough mental simulator of him that I’d basically know how he’d respond. We employed a few other communication tricks, such as both getting IM on our phones or using the pattern of “I plan to do X thing; will time out and go for it in 24 hours barring objections”.

When you have a rapidly-growing company, you’ll find the organization itself constantly changing out from under you. As Marc learned to make changes in the organization, I found myself having to re-learn the same. We went from being an organization of close friends to being a post-Dunbar’s number company, where we had to figure out how to operate well even though some people have never even met. Having a partner in this (especially one who had run larger organizations) was incredibly valuable, and I don’t know how I would have made it through otherwise.

I’d expected that I would find myself suddenly with a role vacuum, and I’d get to fill it however I wanted. This was hugely appealing: since about a year in, my role had been almost entirely reacting to the problems of the day. This would be the first time I’d have a chance to define what I wanted to focus on.

I went on a bit of a CTO vision quest, asking about 20 different CTOs and VP Engineerings to describe their roles. I went in expecting every CTO to be chief architect. But I wanted to know how they pulled it off: I was trying to be chief architect in addition to “early employee”, and I had no idea how to do that job well part-time. (And most scarily, I felt our systems were being held back because everyone was assuming that I would be on top of the problems.)

But to my surprise, I found only one CTO for whom that was true. Everyone else viewed themselves as the facilitators of the technology organization. Sometimes this was about connecting senior engineers. Sometimes it was mentoring. One thought-provoking case for me was a CTO who was effectively head of product. I realized that there’s a huge difference between head of product and head of infrastructure: a good product is simple and digestible, so one tends to quickly distinguish bad from good. In contrast, you can tell good infrastructure only by building on it extensively. So it’s much more tractable to be part-time head of product than to be part-time chief architect.

I realized the most important thing to do was to empower our engineers to make big changes and improvements (plus, we’d been hiring some especially amazing engineers recently, and anything else would be kind of nonsensical). Marc and I set to work on enabling and encouraging major projects to improve the core of Stripe. I also started an “architecture working group”, a group of engineers available to help others build better systems, and a forum for figuring out where we’re taking our infrastructure.

However, one thing I hadn’t anticipated was suddenly losing my feedback loop. I had a snapshot of the organization from back before Marc joined, but I wasn’t getting any updated information. If I tried convincing someone that X was a problem, or Y was the right approach, all my anecdotes and evidence were from the before-time. It was like being a ship formerly tied to shore, but now adrift after someone cut the lines. And most worryingly, the problem was getting strictly worse with each passing day.

I spent a bunch of time thinking about how anyone can even know what’s going on in an organization, or what the problems of the day are. I came up with at most four possible mechanisms:

  1. Doing the work: if you’re, say, writing code, you have direct experience with what’s good and what’s bad.
  2. Talking to lots of people: you get an aggregate view and can tell what the sentiment is.
  3. Observing the work: maybe you could try to be architect-y and read all the diffs. (I actually once spent a month doing this, but it felt like a waste of time — most of the work was reconstructing the author’s state of mind.)
  4. Plan the work: you could try to plan everything out, though I’m actually not sure that this is sustainable without some other feedback loop.

I realized I was doing none of those. And looking at that list, I knew exactly which one would make me happiest. The question was how to get there.

I played with a variety of patterns for writing code. Many of them didn’t work: for example, “go off in a corner, come back with a prototype, and dump it onto an engineer to maintain (or just leave it unmaintained)”. I know there are CTOs who do this, but I’ve never found a variation that feels great (if you’ve seen this working, please let me know). An incrementally better version was “work with an engineer from a team, and build a new prototype together”. But this was also a bit of an uphill battle, since it required constantly fighting for people’s time.

I’d met another CTO at a dinner who told me he’d recently gotten back into coding. I met up with him asked him to reveal his secrets. How had he done it? He looked at me and said, “Coding’s the thing that I love. I knew I’d do a far better job at writing code than at anything else. I just needed to figure out how to get leverage out of it.” For him, that was improving both his company and the industry better by building an open-source platform for their infrastructure.

This was last month. I’ve started working on a team and writing code again. It’s not been easy: there are a million other things that come up. But the more time I’ve spent immersed in producing code, the better perspective I’ve had on the organization, and the better I’ve been able to support people, get them excited about what we’re building, and help them improve their work.

Sometimes I wonder whether I’m justified in making this choice — am I missing higher-leverage activities by focusing on code? But one of the best pearls of advice I’ve heard (from yet another CTO) is that it’s not about time management, it’s about energy management. It’s important to find activities that recharge you (independent of leverage) so that you have the energy to deal with the high-leverage draining stuff.

What my role will look like from here, I have yet to define fully. I’m too busy coding.





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