High Low Piccolo with Ian Steyn

In the show's first ever video episode, Ian is joined by Justin Jackson, the CEO and co-founder of Transistor.fm (and the reason this podcast exists)! As it turns out, video has found its way into every corner of the company in the past few weeks, and together Ian and Justin reflect on  lessons learned through video's impact on customer support, engineering, product design, and business growth.

Justin talks customer calls, while Ian reflects on gaining so-called "expertise" in video questions and docs. Both feel the tension of mediating between customer expectations and engineering priorities, and reflect on how that tension can be used towards forward progress. Finally, Justin discusses what indicates that a new product really is in demand, and Ian celebrates the launch of his own little product (the integration project has been deployed!). 

Timestamps:
  • (00:00) - Intro
  • (02:04) - HIGH - Justin
  • (05:11) - Discussion: Get out of the way
  • (07:01) - HIGH - Ian
  • (09:01) - Discussion: What is needed for continued growth?
  • (14:12) - LOW - Justin
  • (17:11) - LOW - Ian
  • (19:40) - Discussion: How can we reduce the friction?
  • (23:25) - PICCOLO - Justin
  • (26:47) - PICCOLO - Ian
  • (30:18) - Wrap-up

Links:

Creators and Guests

Host
Ian Steyn
Computer Science Student
Guest
Justin Jackson
Co-founder of Transistor.fm

What is High Low Piccolo with Ian Steyn?

Every episode, Ian shares a high-low-piccolo about his learnings as a software intern: a success, a challenge, and something interesting.

Justin:

Listen, people. If you've been listening to Ian this long, he teased you along with the five, ten, fifteen minute episodes. Now it's time for the big one.

Ian:

Hello, and welcome to the fourth episode of "High Low Piccolo with Ian Steyn", where I share with you a success, a challenge, and something interesting I learned in the past two weeks. I am the titular Ian Steyn, a curious guy and computer science student doing a summer co-op at Transistor FM, the company that hosts and distributes this very podcast. Today, we are on video, and joining us is Justin Jackson, the CEO and co-founder of Transistor FM. Hi, Justin.

Justin:

Hey, I'm excited to be here. I've been listening. I'm your number one fan. Listen to every episode.

Ian:

You really are, because you're the one who asked me to do this podcast.

Justin:

I can't tell you how pleased I am that you're doing this. I think this is - I mean, I figured that you should probably do one as a part of your summer co op, but it's ended up being - I think every new hire from now on out should have to make a public podcast.

Ian:

There you go. We've started a trend.

Justin:

Yeah. Yeah. We're gonna we're gonna institute it as a thing that needs to happen. I think it's great, just to have somebody journaling their experience as a new employee is interesting, to hear your perspective as a comp sci student.

Justin:

And now you're kind of reflecting on your education, but also kind of applying different things and learning different things. I think all of that is such helpful... it's probably helpful for you. It's certainly helpful for me. So, I've been loving it.

Ian:

Great. Yeah. Well, it has been good for me. You've wanted me to reflect on what I'm learning, but I'm also interested in what you are learning and what your two weeks have been. So let's jump into it.

Ian:

Okay. Justin, what was a personal success for you this week in the world of Transistor, and what did you learn from that?

Justin:

I got on a call with a customer called Kent C. Dodds.

Ian:

Oh, yes.

Justin:

Who is a highly influential JavaScript educator. He's got, like, 350,000 followers on Twitter or something like that. And he's one of the early users of our video podcasting features. And he's been really pushing the video beta, running into bugs and problems.

Justin:

And what I was getting in chat was he was getting frustrated about some things. And I think because he was getting frustrated, it was getting hard for us to deal with it in customer support chat. And to me, that is a signal - as soon as there's any sort of discord in a text-based chat, I've just learned the hard way, you've gotta jump on a call. As soon as you start to feel any sort of like, okay, they're getting frustrated, I'm getting frustrated: jump on a call.

Justin:

It instantly humanizes the other person. And I was also just excited to have Jon join me on the call, my co-founder (he's the engineering side of Transistor). And I think customer calls are incredible because you can get an immediate sense of what's going on in their world that brought them to Transistor. We see things from our perspective, which is just, oh, here's a customer who's having a hard time, or here's a customer who's pushing the limits of the feature, or here's a customer that, you know, isn't doing things the right way or whatever.

Justin:

But we are just a means to an end to them. In fact, Kent had this great line. Every customer call always has incredible lines, and I always try to record them if I can, like I get their permission. But he had this great line where he says, "for me, the value prop of Transistor is as soon as a listener pushes play. Everything else he says is just friction for me."

Justin:

So for us, Transistor is our world. We're like, this is a cool software we're building, and we're doing it the right way and all this. But for a creator, Transistor is just a means to an end. He finishes recording, and everything that happens from recording to having it live on Spotify or Apple Podcasts is friction. And you've probably experienced some of this as well, right? Like just the editing and...

Justin:

So getting a window into a customer's life, I think, is always a gift. Even just seeing their background, what context are they in? Are they at home? Are they in the basement? Are they in their spare room? Are they at an office?

Justin:

You get an instant sense of who these people are. It humanizes the customer, which I think is really important. And so, yeah, that was my high.

Ian:

I think it's interesting to think of it as, like, the ideal is: you finish recording a podcast episode and then you're done. Because some people do really enjoy, the editing process and other aspects. But we don't provide that even. So like for us, we are just making... Transistor is just making the distribution easier and providing the other stuff.

Ian:

And so it might be neat, someone can appreciate it as, like, a good bit of software. But it is still something where they wanna get through that process as fast as possible. It's not necessarily entertainment or something for them to be in the Transistor software.

Justin:

Yeah. I think most products - well, maybe not every product, but most products - could benefit from getting out of the way.

Ian:

Mhmm. Yeah. Honestly.

Justin:

There can be a self importance with products where they think, "Well, no. We are the product. Like, respect us."

Ian:

Yeah.

Justin:

But, really, I think most people's frustrations and you can probably identify with this as a user. Like, just get out of the way. Instead of having to navigate layers of UI and getting through really difficult workflows, my preference would actually be for us to remove more things from the UI and make it dead simple for someone who does wanna click around with a mouse and do things the old fashioned way.

Justin:

That is actually most of our customers. 80% of our customers are just very simple use cases. So simplify the actual UI for them, but then add more of these advanced features in the API.

Ian:

Sure. Sure. Yeah. That'll be an interesting balance to kinda try and find.

Justin:

Mhmm. Yeah.

Justin:

So Ian, what's your high from this past week?

Ian:

Well, so both of the other customer support people, Michael and Helen, have had time off in the past few weeks.

Justin:

What!?

Ian:

I know. Don't tell them I told you.

Ian:

So this weird thing has happened where they still know more about most stuff in customer support than me. But I'm the one who's consistently been here while we're ramping up our video podcast launch, our video features and, like, beta testing that feature.

Ian:

And so recently, Michael's been calling me, like, our "resident video expert", which is funny because I feel like I'm anything but, especially, you know, compared to the engineers who are actually implementing this stuff.

Justin:

Mhmm.

Ian:

I'm asking them questions all the time. But in terms of onboarding people and answering their questions and knowing where we're at with that, I do feel like I have a pretty good handle on it.

Ian:

Like, I've been trying to keep our documentation up to date. I've set up shortcuts and templates for myself so I can respond to customers about video questions really quickly.

Ian:

Even yesterday, I was working with you to start contacting people who signed up for the video early access wait list. And, yeah, I'm just happy to like take ownership of that weekly task and of video stuff in the customer support chat right now because someone kinda has to and I'm so immersed in it right now that I feel like I can handle that.

Ian:

Yeah. It's just it's nice to be able to see a question coming in and to feel like, oh, I know that I can answer this one because I've answered three other questions like it today and I have written down the answer for myself.

Justin:

Yeah. Yeah. Can I ask you a question about that?

Ian:

Please do.

Justin:

So first of all, it seems like one side of this was Helen and Michael left, which created the opportunity for you to then have to step up. So getting called on to step up is one piece of it. And then it feels like people need a certain amount of challenge. It can't be so much that it's overwhelming.

Justin:

And then on the other end of it, you kind of develop this confidence. How do you think a company or a team can create those opportunities on an ongoing basis? Because it feels like most roles have, like, an initial period where you're kind of ramping up, then it's like, oh, this is so hard. This is all confusing, I don't know.

Justin:

But even for you now, you know, compared to where you were in May and where you are now, you're much more comfortable.

Ian:

Yeah. For sure.

Justin:

And I think there's also just this - again, ownership, self confidence, feeling of autonomy - there's all these good feelings that come from that.

Justin:

So how do you think a team can create that environment? Or is it even possible to consistently create that environment where people can rise to the occasion, build up this sense of like, "yeah, I did that. It's motivating."?

Ian:

Yeah. That's an interesting question. I don't know. Because for me, it feels like that's just my standard space that I operate in. I think because I'm a student, I'm very early in my career, I'm constantly, like, learning stuff.

Ian:

But, I mean, Marco, who works here in the shared office space we work in was telling me the other day, he had a friend who quit software engineering like ten years in, because he was frustrated at the fact that he kept having to learn new stuff. He was like, "I already know the thing. Like, just let me use that knowledge that I have instead of continuing to learn."

Ian:

So what I hear is that in the technology space that is sort of built in because things are changing all the time. There's always new challenges that come up that you have to learn.

Ian:

But I don't know. Like, my experience right now as a student is that that's just how it always is. I can't say for sure if that will sort of happen on its ownn, you know, in the future of my own career - or if that will need to be fostered somehow.

Justin:

One thing that seems to be true is that you can't stay stagnant. Like, at first, I had this thought that we could just get to the point where we were all comfortable and calm and that would be the ideal state. But what I've learned, I think, is that actually that that's not good for a company because humans - at least most humans that are driven - wanna continue to learn, wanna continue to progress, wanna continue to move forward. We want a goal that we're going after.

Justin:

And so, yeah, it wasn't until we, for example, this past year, set the goal to tackle video, which felt like a very difficult problem, that I felt like, "wow, now we're growing again. Now there's a challenge. Now, you know, we're running into to difficulty that we didn't before," but it kinda feels good. There's something related to that that's can be motivating.

Ian:

As you're talking about this, I'm forming, like, a formula for this, which is - I think part of it is: growth happens quickly when it is required. It's that thing of "necessity is the mother of invention." Like, I have needed to gain a bunch of knowledge about our video beta because customers are constantly asking about it.

Ian:

And so not just giving someone a project just to learn, but, like, a project that has a point to it.

Justin:

Has purpose. Yeah.

Ian:

Yeah. That part is important.

Ian:

And then also, like, just allowing people to do things that they haven't done before or that they don't seem a 100% qualified for at the start of the project. That's something that I've appreciated as an intern here, is that I've been given some responsibility, and that has allowed me to, like, step up and grow and learn a bunch of stuff from that.

Justin:

Yeah, no. I think that's I think that's it. There's obviously a lot of other challenges for leaders, which is just fitting that puzzle piece together and figuring out, you know, what can we accommodate as a team. A lot of other questions on the leadership side.

Justin:

Right, yeah. I see what you're saying. There's some there's some things you gotta work out.

Justin:

It's challenging. It's - yeah, it can be totally challenging.

Ian:

So just to reframe again, just in case anybody new is listening to this. On this show, "low" is not necessarily a bad thing. It can be low in the sense that it's something that was more boring or more difficult.

Ian:

It can be bad; it's supposed to be something that was an opportunity to learn, though. So what was your low this week, Justin?

Justin:

I... mine is a little bit of a frustration.

Ian:

Sure.

Justin:

And it's nobody's fault. Ultimately, it's my fault. Ultimately, it's just the thing that happens. But we have a list of 1500 people that want video podcasting. And the essence of a list like that is that it gets cold.

Justin:

So some people signed up two months ago, and they were hot. They were warm leads. They wanted to accomplish something, which is: they wanted to publish video on Apple Podcasts and Spotify and YouTube. And that motivation brought them to our website, which is already a gift - to get anybody to show up to your website. And then for any of them to opt in to saying, "Yes, I want this thing."

Justin:

A lot of these are existing customers. A lot of them are brand new people. And I just see before my eyes, it's like the list is degrading because people's motivation subsides.

Justin:

Jason Fried has this great quote where he says, "Inspiration is perishable." And I think that's true for customers.

Justin:

They get inspired one day to say, "You know what? I'm gonna fix that door lock. Like, it's been bugging me forever. I'm gonna go to Home Depot. I'm gonna get it done."

Justin:

But if there's too much friction or too much waiting or too much in the way of them achieving the thing, they'll be like, "Ah, forget it. I'll just..." And then it goes back to the back burner. So I have an incredible amount of impatience and desire for us to be reaching out to this list, for us to be communicating, and for us to be onboarding as many as we can.

Justin:

We've onboarded, I think, 158 people, which is fine. It's in beta. There's lots to figure out. But this is just the tension in my soul. It's been like this forever. It is impatience.

Justin:

It is a good impatience, I think, because we've never had a waiting list for any feature that's 1500 people. Never.

Ian:

Right.

Justin:

So the the fact that there's so many people interested - like, there might be ten, twenty people that have signed up today, and - I'm just eager to get to them. So that's my low. High in that we finally did something about it. Like, we sent out a big bulk of emails. But that's that's my low for this week.

Ian:

That is interesting. It's it's honestly not too dissimilar from my low.

Justin:

Okay.

Ian:

My low is kind of like the flip side of my high. Where because I'm so immersed in doing customer support for video, I'm also very aware of the rough edges hat our features have right now.

Ian:

You know, people are catching all these little cases where our product doesn't quite do what they expect or they're trying to do something and it doesn't work. And that's a good thing actually because, you know, that's like the whole point of doing beta testing before you fully launch a product - we're getting people to to do some testing for us.

Ian:

But I also feel the tension where people are, like, eager to start using this. They have something that they wanna do now. They wanna post videos now for episodes instead of, like, backfilling it three months from now.

Ian:

And so I sympathize with the customers. I think I'm like, "Yeah, man, you wanna do something reasonable? But it doesn't work." And part of me just wants to fix that right away for them.

Ian:

But then on the other hand, I also sympathize with the engineers who are fixing all these things. Because I know that they wanna fix stuff, but they can't do it all at once. You know, it is a process. They have to do one thing one day and another thing another day.

Justin:

Yep.

Ian:

And so the challenge, I guess, is just managing that tension.

Ian:

Managing it internally because it it doesn't help for me to get too stressed out about things that are outside my control.

Ian:

Like, for example, Apple requires that users go to them for approval for video. And so we have to be sending people to them and then they come back to us and there's like friction there. But there's not really anything we can do about that just yet.

Ian:

And then also, I'm learning to kind of manage that tension externally as well.

Ian:

Like, how can I translate from the customer side to the engineering side? Like, "Hey, here is a clear structured explanation of the problem that needs to get fixed. Here's how high of a priority it is." And then also translating the other way, like, "Okay, hey, customer, we're working on it. It's gonna take some time. We're still in beta testing."

Justin:

What's great about hearing you articulate that is that I can... I immediately see that whole process, and I wanna fix it in a structural way. So two things I think that would help us a lot.

Justin:

One is, have everybody that wants video go into their distribution settings and say, Request Apple Approval. And then that goes into a CSV file that we batch upload to Apple every week. They approve, and then we notify the user, "Hey, you are now ready for video. All you need to do is upgrade your account to the the professional plan. You're ready to go." That would immediately cut out a huge amount of our friction in this process.

Ian:

Totally. Yeah.

Justin:

So I think that's still a lot of friction because they have to wait. I don't like making people wait. I hope Apple fixes this because making people wait kills momentum, like we mentioned before.

Justin:

The second piece, I think, is that if we look at customer service as a process, the thing we're trying to avoid is contacting the engineers and saying, "Hey, this thing's broken, or we need you to run an SQL query, or we need you to use whatever system you have on the back end to determine if they've submitted their approval for Apple yet."

Ian:

Yeah.

Justin:

What I would like to see is a support engineer in that role, where they they have, you know, access to SQL. They can make queries. In the command line, they can get all the information. And they are a buffer, a protective wall around the engineers.

Justin:

So we can do things that don't scale manually. I think in the process, we can implement another person there. And that would be... and that might mean all three of our current support people just have more of that like, it might be painful in the short term. Like, we have to train people up and get them the right security stuff.

Justin:

And there's danger there. And there's challenge. But I think there would be a benefit to that - to fixing that whole process.

Ian:

Yeah. Yeah, because there's things that, like, are issues that are sort of long term - you know, it's a user story, the product needs to get updated with that, that thing needs to be fixed.

Ian:

But then there's also things where, like, this user just needs their video on Apple right now. And the engineers have to go in and investigate and run a script or something. And that takes time away from their ability to improve the features faster.

Ian:

So it's like we're getting lots of good feedback because we're doing beta testing. But it also causes this, like... it throws some wrenches into the smooth processes that we want.

Justin:

Yeah. And ultimately, there's always gonna be some mess. That's just the reality of life. We're actually never gonna get back to normal. So now we just have to figure out a new process for, you know, addressing it the best we can. Acknowledging there's always gonna be some mess for every single person in that whole flow, but we can at least address the main points of friction and, you know, make the whole process better.

Ian:

Yeah. Yeah. Piccolo.

Ian:

Justin, what was your Piccolo this week? And how clear are you on what I mean by Piccolo?

Justin:

I think it's just something interesting I learned. Is that right?

Ian:

Pretty much. Yeah.

Justin:

Okay.

Ian:

It's just, Piccolo has nothing to do with the instrument other than that it rhymes with low, high low Piccolo. I love it's just something else interesting that happened for you this week or that you learned.

Justin:

I mean, it's good format. So it's related to what we've been talking about. I've been loving this writer who writes on business startup topics. His name is Rob Snyder. And he talks a lot about how customer desire and motivation really works.

Justin:

And a lot of people are like, well, how do you know if there's enough customer demand for the thing that you're building? Right? That is essentially the problem in business is that you're thinking about offering something, but you don't know if enough people are going to actively want it. Right?

Ian:

Right.

Justin:

And his response is, the evidence is that they are actively trying to buy despite all of the impediments that are put in their way. So it's like, "Hey, this feature's not really done yet. We can't really release it." They're like, "Please just give it to me anyway."

Ian:

Right, yeah. That's happening for us.

Justin:

That's happening for us!

Justin:

You put up friction. Like you say, "Well, to access this, you're gonna have to put in your credit card first." Right? There's you know, maybe your marketing materials aren't ready. Maybe your processes aren't ready. But despite all of the bits that you feel aren't ready yet and it's not quite right, people are actively trying to buy.

Justin:

Now, the death knell for any business is when there's silence. Like, you you finally getting get around to offering the thing, and people are just kinda like, "Meh." They're not actively trying to buy.

Justin:

But a good early signal, and we're getting it with video, is despite the fact that you have to ask Apple for approval, and despite the fact you have to sign up for a waiting list, and despite the fact that you have to upgrade, and despite the fact that you have to you know, despite, despite, despite, despite, "I still want it."

Justin:

That is kind of the holy grail of customer demand. That's what every business wants. It is incredibly difficult to find and capture in the real world.

Justin:

In this case, I observed it. I knew that the demand for video was there. I've been wanting this for a while. And then to capture that wave of demand when it comes is obviously not easy.

Justin:

But the signal that you're looking for is that despite the fact that you just have a coming soon page, they're finding you on LinkedIn and DMing you and saying, "I know it says coming soon, but is there any way I can get access now?" That is the signal you're looking for.

Ian:

Yeah. That's interesting. I mean, I know exactly what you mean because we are really experiencing that right now. But I hadn't really thought of it in such articulated terms before.

Justin:

What was your Piccolo?

Ian:

Yeah. So my Piccolo this week is honestly kind of a high as well. It's just that my integration project is deployed now.

Ian:

So I did a little project to allow us to create customer support stories (or tickets or whatever you wanna call them) in our customer support software. And then it gets posted to our project management software right away. And the link comes back to the customer support software.

Ian:

That's just a little process that I got to improve. And in particular, this past week, what I got to learn about was how to deploy my code on a Cloudflare Worker. And so I got to work with Jason and John a little bit. I had a call with them, which was fun. (Those are our engineers).

Ian:

And it was nice to do that not only in theory, but, like, actually practically sit with them and be like, "Okay, this is where it's gonna live." It's owned by a company account so that when I leave, it's still around. And what's like a practical way that I can get the API secrets to John and Jason. Mhmm. And okay, now that it's running, how do we check that it works?

Ian:

And that's something I hadn't thought about. So Jason was like, oh, just add a little endpoint to the API that just... you can go to that URL in the browser and it'll just like show up as like "success" or, you know, "health check true." And so I did that.

Ian:

And now I'm like, oh, that's a great little tidbit to know for the next time I design an API endpoint or an app or something: add a little health check so I can check that it is running.

Justin:

Yeah. What an awesome project. Because that's kinda everything. You had to say, "Okay, here's a problem that somebody's having. There's enough demand there that they've asked me to build it."

Justin:

And then you have to... there's all sorts of decisions you had to make. Like, it could have been for example, the software could work totally different. It could be like, oh, you've actually gotta go to a separate Google form and the link just opens up a separate Google form and then it gets submitted and notifies you in Slack.

Justin:

But yours, you submit it right in the context in Shortcut, and then it automatically posts back to the conversation thread as a note. And that is a product decision. That is a problem solving on a higher level than just like, "Oh, here's like a bunch of code I gotta write or here's whatever." This is like, "Oh, I've gotta actually make some shaping decisions on how I'm going to shape up this piece of software and implement it."

Ian:

Yeah. The hardest parts of this project were definitely not the coding. There were coding things I had to learn, but it was the decision making of like: What tools are appropriate for this? What resources can I use that the company already has? What do the users - the three users - need?

Ian:

So that was a good little microcosm of developing a product.

Justin:

Yeah. I love it. Well done.

Justin:

From my side, you've done excellent. This is like ... you're past your first month now. Right? You're about a month and a half in?

Ian:

Yeah. I think I'm almost at two months. This is week... well, no. Not quite. This is week six and seven that we're reflecting on right now for me.

Justin:

Yeah. Yeah. I think you've I think you've done great. This has been really wonderful to have you on the team. You add a lot to our team meetings. It's exciting to see somebody else learning all this stuff. It's exciting to hear your reflections on the podcast.

Justin:

So I just wanna say that publicly that I've been impressed with your work so far.

Ian:

I appreciate it. You don't know if it's public yet. I might edit it out. I probably won't, but...

Justin:

If you're a UBCO professor listening, give this man a good grade.

Ian:

Thanks. I'll play that for them. Yep.

Ian:

Thanks for joining us, Justin. This has been "High Low Piccolo" with Ian Steyn and Justin Jackson. Thanks for listening, and tune in next time to hear about more interesting stuff that I am learning.