Charlie Harrington

About Library

'Escaping Web' Season One Retrospective


My friend Oz Nova and I started a podcast last year called Escaping Web. With a million and one podcasts out there, you might be wondering about our catchy tagline? Our special hook? Our unique... perspective?

Escaping Web is a show celebrating software engineers who've found their calling beyond routine web development.

The idea for the podcast began with the observation that most engineers who "break into tech" (read: bootcamp grads or "non-traditional" aka non-CS degree backgrounds) typically begin their careers with web development roles (👋 hi!), and that these engineers often find themselves in a rut after a year or two. Bored at work. Feeling unfulfilled. Looking for something more... (name your favorite Disney or Pixar "I want..." song).

As the head of Bradfield School of Computer Science (an online school for working software engineers "seeking mastery"), Oz meets lots of interesting characters who fit this mold -- and many who've broken out... into fields like graphics, quantum computing, database design, etc.

Our podcast interviews these engineers to learn what makes the tick, and more importantly, how they found something that they're passionate about at work. Was it a six-month sabbatical to intensely study computer architecture or discrete mathemathics? Or something else?

Mostly, Escaping Web is a podcast about learning how to learn how to learn.

We recorded six episodes last year with six amazing individuals. You can find more details and links to the audio below, along with the voluminous shownotes (which grew and grew with each episode).

We recently decided to put the show on indefinite hiatus (don't worry, I'm calling it Season One), and I'll use the next section of this post to go through some of my own learnings about starting a podcast in 2019.

Starting a podcast

It's easy! Everyone says that, and I pretty much agree. Here's a simple list of the things you need to do to release your own podcast:

  1. Record one or two episodes of audio
  2. Edit them (optional)
  3. Upload them somewhere on the internet that is publically accessible
  4. Generate an RSS feed that can tell podcast directories where to find your audio files
  5. Tell the podcast directories (e.g. iTunes, Google Play, Spotify) the URL of your RSS feed
  6. Line up sponsorships with Squarespace, Linode, and a subscription coffee service (also optional, unfortunately)

But that's it! Podcasting is still an open medium. There are also services that can take care of some of these steps for you. I'll run through my experiences with each step now.

1. Recording audio

This one should be easy, you'd think. But it's not. In fact, this one is the primary reason that we went on hiatus. Given the format of our show (bi-weekly interviews with guests), we had a large scheduling onus to coordinate between ourselves and our guest-of-the-week. I think this challenge alone put the pin in "season one" and I think I'll need to do a better job with coordinating schedules if we resume the show. One thought, which I'm only thinking of now and wish I'd thought of earlier, would be a Calendly link for guests to sign up on.

Even if you're not doing a guest-of-the-week format, there's still a mental hurdle to clear of "coming up with something interesting to say" on each episode. That's where your show theme and host chemistry can really make or break you. Shows like The Flop House really nail this combo: not only are they individually and collectively hilarious, the "bad-movie-recap-of-the-week" format keeps things interesting and fun every single episode. Similarly, the Apple-oriented Accidental Tech Podcast has become less about Apple news for me, and more about the trials, tribulations, and just-plain-fun quirks of each of the hosts. This is where podcasts have this dangerous turn as a replacement for human-interaction. When I'm thinking to myself, "Oh, Casey, it's time to get a new computer," I know that ATP has me hooked. I'm happily hooked, but hooked nonetheless.

If you do give Escaping Web a listen, you might agree with me that I think we missed the mark on developing host chemistry. We don't really have any Siracusan "follow-up" segment to provide weekly continuity (and highlight the strange things in our personalities that keep us up at night). There's also no regular cadence on what "Oz and Charlie are up to."

I still think we went the right way with the interview format for our show, but I'd love to strike a better balance in the future. A show like John Gruber's The Talk Show does this incredibly well. It's an interview show with a short rotating cast of characters, which makes it feel contiguous. For example, I know that John has a stack of like 400 bundles of firewood in his garage because of an accidental Amazon overpurchase. It's this kind of magic that you seek.

Weren't we supposed to be talking about recording audio? Oh, right. There are two formats for this, one of which should be ignored given our current collective quarantining:

  1. In-person, each with an individual mic and headphones
  2. Over Skype, using Skype Call Recorder (and Piezo as a backup)

The goal here is to get separate tracks for each speaker so that you can mix and edit them separately. In the case of Escaping Web, we went with an unfortunate third option:

  1. In-person, sharing one mic with no headphones (and occasionally over Skype with Charlie and Oz sharing one mic)

Why? Why, oh why, did we go this route?

Mostly because Oz already had this big ol' Blue Yeti mic, and we didn't want to invest more in a more expensive rig. This was probably (definitely) a mistake, which you can hear in some of the episodes like Grant's (sorry, Grant!). When you have one mic, even if it's a "good one", it's impossible to get the voices right.

I, for one, am extremely loud. Oz, not so much. Our guests, somewhere in between. Can't you just fix this on the editing floor? Maybe... if you know what you're doing (I don't). Take this advice: like The Beatles discovered in the '60s, magic can happen in the studio edits when you've got multiple tracks to record on.

I've gone on quite a bit already, and we're still in section one, but I should mention something about the Skype recording experience. It's great! I always hear podcast hosts grumbling something or other about Skype, so I was happy to discover that the experience of recording with Skype Call Recorder was seamless. It automatically splits your call into multiple tracks. I also fired up Piezo as a backup. We didn't go the full-redundancy route of having each person record their own audio and send it back to me, and we never got burned by this. But I can understand why this important. Also, we didn't go the route of ensuring that our remote guests had any sort of quality mics or anything like that. Maybe this is why Terry Gross has her guests go into a radio studio for their interviews. In our case, it was hard enough to align schedules that sending over recording equipment to our guests would have been a clear no-go.

2. Editing audio

This can be another rabbit hole time-warp. But it's also not that bad, and maybe even fun.

Our shows ran about an hour or so, which meant we had about 90 minutes of audio, give-or-take. My goal was always to try to edit the show the same night that we recorded it. I wanted to just get it done. This worked the first few times, but less so after a while after the excitement of the first few episodes wore off. The edits became a looming thing on my to-do list for the next few days. One of those to-do's that's not that that hard... um, to do, but you've just got to sit down and do it. And ain't that just the challenge of all to-do lists?

So, what is editing? I'm not totally sure. Here's what I tried to do:

My tools were the free and awesome Audacity (I'm not sure if this works just yet on MacOS Catalina) and Apple Logic (although you could use the free GarageBand just as easily). I watched a few YouTube videos on editing podcasts, plunked around and did my best. The sound quality is pretty bad on some of the episodes. Someone with real editing chops could have made them sound better, but I think the real culprit was the lack of quality mic-ing of our voices.

Admittedly, the thing I looked forward to most about the edits was coming up a variation on our intro music theme that I "composed" with the on-screen keyboard in Logic. I like to make weird little songs on Logic/Garageband while on flights, and this was too good an opportunity not to get a little musical and a little weird. Each episode is different. I hope you like them!

3-4. Hosting files and generating RSS feed

Now we're into what "folks in the biz" call "podcast hosting." I combined items 3 and 4 because these tend to go hand-in-hand.

There are many podcast hosting companies out there. If you're following along, time was our biggest constraint in this entire endeavor, so we decided to outsource this part of the process rather than whip something together ourselves.

I chose Transistor.FM for our podcast host. I listen to their maker podcast Build Your SASS, and I've loved following along with Justin and Jon as they document their challenges and wins and concerns as they build Transistor from the ground up. In addition to making it really easy to upload your audio and generate your RSS feed, Transistor also provides (1) an automatic website generater for your show and (2) a listener analytic dashboard. They also provided fantastic customer support when I had a few questions about the process. Definitely worth the $20 a month for our young, growing show.

Unfortunately, now that we've gone on hiatus and we don't know when we'll record our next episode, we decided to cancel our subscription. I've finally done the work of hacking together a simple solution to maintain an RSS feed for our show using public GitHub Pages repos to host our RSS feed and audio files. I think this will work fine, unless we suddenly get a ton of listeners out of the blue. But given what I saw in the Transistor analytics, I think we'll be okay for now.

5. Adding your RSS feed to the directories

One slight bummer is that, even with a podcast hosting service, you still need to submit your show to all the different providers separately. These are places like iTunes, Spotify, and Google. There's a few more, too. Stitcher is one. I don't know all of them off of the top of my head, but there are definitely a few more places that you can share your show. Still, the iTunes directory, Spotify, and Google are the big three that "matter."

This is mainly a bummer in that, if you've made it this far, you're ready for your show to hit the world by storm! Don't forget to allocate enough time for your podcast to be (1) approved by iTunes and (2) appear in iTunes. If you're somebody who's expecting a big "launch day", be aware that this can take something like a week or so.

To take the other side of this, I've actually now found it to be an advantage to have a direct relationship with each of the podcast directories, because I've been able to easily update the URL of our RSS feed to my new GitHub pages solution.

Oh! Also, your show needs show art. Here's what I sketched up for Escaping Web, and Oz (for some strange reason) loved it, too.


Our spider has a Nand gate on its back. Cute.

6. Finding sponsors!

Whoops. We never did this one. This is especially unfortunate, because I think I'd do a great ad-read.

Promotion is hard, in general. Not just for podcasts. Maybe obscure cream can rise to the top amid the noise vortex (mixed metaphor?), and I think we were at least semi-creamy, and now I've lost my train of thought. But... yeah, we didn't focus on promotion and I think we could have done a better job at this. I give us a thumbs-down on this effort.

We did set up a Twitter account for the show (@escapingweb), and Transistor helped by auto-tweeting each new episode as soon it went live. I also tried to get the companies of our guests to re-tweet us, but this was only semi-successful. Like I said (did I say this?), content marketing is hard. We just wanted to talk to interesting people and put our show out there to the world for people to hear it. And we achieved that, so that's nice.

In fact, I wanted to share some of the things that folks Tweeted about our show that make me happy:

Highly recommend the @EscapingWeb podcast for any programmers out there

Lots of great stories from folks who entered the field untraditional and are killing it 💪🏼#100DaysOfCode #coding #webDev

— Clifford Fajardo (@CliffordFajard0) September 5, 2019

Agreed. @EscapingWeb is one of my favorite podcasts. Excited to listen to the latest episode!

— Madison Kanna (@Madisonkanna) September 5, 2019

Great episode, but it was really difficult to hear Grant

— Vegard Stikbakke (@vegardstikbakke) November 21, 2019

Yes, I know, I know. The audio on the Grant episode is the worst. I'm sorry, world. But thank you to everyone who tweeted about the show and shared with their friends.

Also, everyone says that leaving ratings on iTunes is "super-helpful", and I encouraged some folks to do that. We got thirteen 5-star reviews. Is that good? Probably not. But at least they were all fives! Two of my close friends even left a nice written review, and also one person I don't recognize at the moment (but probably also know personally).


Still, these tweets and these ratings and the personal texts we both received meant a lot to me and Oz. So, thank you!

What I learned from season one of Escaping Web (other than how to make a podcast)

Interviewing is challenging. Duh. But I really thought that I'd be pretty good at this right away, and I wasn't. It's a craft that demands practice. I hope to do more of it in the future, if you'll allow.

Take to time to explore things deeply. This is critical to finding your path at work, in life, in the woods, wherever. And, yet, it's so hard to do this if you have a Nintendo Switch (that's why I still only have a Super Nintendo). Our guests found this time in many different ways (from sabbaticals to switching teams at work to taking online courses).

Find a friend who's way smarter than you and spend time with them. This is me talking about Oz, by the way. Every time I hang out with Oz, I learn something about computers or education or whatever that blows my mind and leaves with an even bigger backlog reading list. Thanks for season one, Oz!

And, with that, the retrospective is complete! Onto the shownotes and audio. There are links to amazing things below, and I hope you find them useful in your travels. Here's a short preview of the ones that kept coming up again and again, which probably means something that I'll leave to the reader as an exercise:

Shownotes and audio for Escaping Web

1: A Quantum of Sad Things Happening To Felix Tripier of IonQ

Felix Tripier is a software engineer at a quantum computing company. He's also eating cold lasagna out of a coffee mug.

Find out how Felix Tripier went from high-school and college dropout (watch out Silicon Valley, he's a double-dropout) to working as web developer at several Bay Area startups to presenting his open-source research at a quantum computing conference, leading to his current gig as a software engineer at IonQ, a quantum computing company. Charlie and Oz dig into Felix's study habits and learning goals, briefly dip into theoretical computing topics before coming up for air, and altogether forget to introduce themselves, Felix, or the podcast itself.

Links and resources:

2: Epic Slacking with Roo Harrigan of Slack

Roo Harrigan is the Strategic Engineering Projects Lead at Slack. She’s also the self-proclaimed Mentor Queen.

Find out how Roo Harrigan went from an all-around generalist (product manager, project manager, sales demo'er, customer support agent) to a software engineer on the platform team at Slack, and now the Strategic Engineering Projects Lead reporting to Slack's CTO. Charlie and Oz dig into about Roo's tips for finding mentors, achieving flow state, and onboarding engineers. We also learn that Oz has never worked in the food services industry. Oh, and they remember to introduce themselves and Roo at the beginning. Progress!

Links and resources:

3: Getting Time Serious with Richie Artoul of Uber

Richie Artoul is a software engineer on Uber's Observability infrastructure team. He also really likes distributed timeseries databases, like a lot.

Find out how Richie Artoul went from bootcamp grad to infrastructure engineer at Uber, where he's now building their open source metrics platform M3 and their open source distributed timeseries database M3DB. Charlie and Oz dive into Richie's tips for side projects, reading programming textbooks, finding mentors at work, and navigating large engineering orgs like Uber. We also learn that Richie recently took up Jiu-Jitsu (just like Oz) - and now Charlie's hoping for a Vader / Obi Wan style "roll" in their future.

Links and resources:

4: A Graphic(s) Conversation with Lauren Budorick of Figma

Lauren Budorick is Graphics Software Engineer at Figma. She’s also read the 1989a .gif spec, yet still refuses to pronounce them as "JIFs."

Find out how Lauren went from bootcamp grad to Graphics Software Engineer, first at Mapbox and now at Figma, where she's building their prototyping rendering engine. Charlie and Oz dig into Lauren's tips for learning linear algebra, how to see everything in the world as a triangle, and navigating a company without managers. Charlie and Oz also each try to recount stories of "achieving the impossible", and both painfully fail to remember the exact details of their anecdotes.

Links and resources:

5: Learning Your Stripes with Grant Wu of Stripe

Grant Wu is a Software Engineer at Stripe on the Ruby Application Infrastructure team. He also hates scary movies, but still can’t stop himself from reading their IMDB synopses.

Charlie and Oz dig into Grant’s study habits for self-guided learning (like building a toy kernel and toy compiler) — and how those low-level projects influenced his path to Stripe. The gang gets into it over bootcamps, baking bread, and learning to play music — all with the broader theme of exploring what it means to be creative. To top it off, we learn that Oz has a joint degree in math(s) and the (Australian) law?!

Links and resources:

6: Algorithmically Speaking with Elliott Jin of Triplebyte

Elliott Jin is the Interview Team Tech Lead at Triplebyte. You're gonna hear a lot about Project Euler in this one.

Charlie and Oz explore Elliott's path down the various intellectual rabbit holes (mostly Project Euler) that led him to software engineering at Dropbox, teaching the Algorithms course at Bradfield, and now leading Triplebyte's Interview tech team. Elliott also reveals the correct way to read a textbook (of which Charlie hadn't the foggiest), and Oz and Elliott try to explain to Charlie how they motivate students in their classes through "guided struggle."

Links and resources: