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May 20, 2024 22 mins

This episode of Podversations  features Jonathan Strickland, host of TechStuff, and iHeartPodcasts President, Will Pearson…

As the host of the podcast TechStuff since 2008 (and over 2,000 episodes!) Jonathan Strickland really knows what he’s talking about when it comes to audio. That’s why we had him join Will this week to talk all about how the podcast landscape has changed in the past decade and a half and where he sees it going in the future. He talks about the inspiration behind his episodes, when (or if) he felt like he had a handle on podcasting, and why this became his creative outlet. For all the audio junkies out there, you don’t want to miss this one!

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Speaker 1 (00:04):
iHeartRadio presents Podversations, a weekly discussion with the biggest names.

Speaker 2 (00:08):
And influencers and podcasting.

Speaker 1 (00:10):
Want to one of the secret psychic rituals, Scrub stars
Zach Brath and Donald Fazing News before Every Fake Doctor's
Real Friends Taping how Vice News parachutes into war zones
to rescue journalists from life threatening situations, Or why Keegan,
Michael Key and Blumhouse believe three D audio is the
future of storytelling. Whether you're a newbie trying to break
into the podcast game or an exec trying to refine

(00:31):
your playbook, Podversations is the easiest way to keep your
pulse on the industry.

Speaker 3 (00:45):
Hello and welcome back to the iHeart Podcast Speakers series.
I'm Will Pearson, President of iHeart Podcast. As you know,
we like to get together each week with one of
our favorite creators or producers talk about what they're up to,
and today is a really special treat because we're getting
to talk to somebody who's been doing this pretty much
as long as anyone in.

Speaker 2 (01:03):
The podcast space. We're going back well over a decade.

Speaker 3 (01:07):
One of the originals in podcasting, mister Jonathan Strickland of
tech Stuff.

Speaker 2 (01:11):
Jonathan, thanks for spending some time with us.

Speaker 4 (01:14):
Thanks, well, way to make me feel my age.

Speaker 2 (01:16):
Yes, yeah, yeah, it's well, you might not be old.

Speaker 3 (01:20):
But the podcast in podcast terms, I don't know if
there's an equivalent of like dog years or whatever, but
it's been around since pretty much the beginning, and actually
you and I both joined iHeart at the same time
as part of the acquisition of Stuff Media sometimes more
publicly known as How Stuff Works at the time to
come on board and really grow the podcast division here.

Speaker 2 (01:40):
But you were part of an.

Speaker 3 (01:42):
Original roster of How Stuff Works shows that was stuff
you should know, stuff you missed in history class, stuff
to blow your mind, tech stuff. I am glad that
we eventually learned every podcast didn't have to have the
word stuff in it. But it's a really special group
of podcasts. But before we get to that, can you
take us back pre this would have been pre two

(02:04):
thousand and eight, right, and tell us a little bit
about what you were doing before you started Tech Stuff.

Speaker 4 (02:10):
Sure.

Speaker 5 (02:11):
So, in my previous life, I worked for human resources
management consultants, so I worked for the bobs in office
space essentially, and I worked for that kind of industry
for about seven years, and I was good at what
I did, but I didn't have a passion for it,
and I even had senior consultants tell me. They said

(02:32):
that I really needed to move on and do something
that was passionate about because they could see that that
was I had the capacity for it, it just wasn't blossoming.
That's when I got an opportunity to interview for How
Stuff Works, and I got a staff writing gig.

Speaker 4 (02:49):
I was one of two.

Speaker 5 (02:49):
Staff writers, the other being Tracy Wilson, who is the
host of Stuff You Missed in History Class? And I
got hired on and after a more than a year,
we had the opportunity to launch podcasts. So I had
started to focus on the technology sector on the website,

(03:10):
so it was kind of a natural progression to think of,
why don't we use you to host our co host
at that time, a show that focuses on technology and
how it works.

Speaker 2 (03:21):
Yeah, well you mentioned Tracy Wilson.

Speaker 3 (03:23):
It's funny, you know, one of the legendary co hosts
of Stuff You Missed in History Class, quite possibly the
biggest history podcast in the medium in terms of a
number of people who've listened over all these years, and
Tech Stuff of course, with tens of millions of downloads
to the podcast.

Speaker 2 (03:40):
Over the years. You may be approaching one hundred million plus.

Speaker 3 (03:42):
I don't know that the total number, but it's been
a ton of listening that has happened over the years.

Speaker 2 (03:49):
So tell me about the beginning of the podcast.

Speaker 3 (03:51):
How you were working with how Stuff Works on the website,
working to write articles there, and then this idea came
about of you know what, we have all these incredible
articles and it feels like there could be a life
beyond these to be able to translate some of this
language into the spoken word and be able to put these.

Speaker 2 (04:09):
Out as this new thing called podcast.

Speaker 3 (04:12):
Maybe go back to that moment when it was a
decision was made to start doing this with tech Stuff.

Speaker 5 (04:16):
Yeah, it was exciting because there was a lot of
early evolution. We learned as we were doing and things
changed pretty quickly, but it was in a thrilling way.
So when we first started, the idea was that these
are going to be very short form podcasts. You know,
we had had a show called brain Stuff that had
been publishing for a little while and those were maybe

(04:37):
a minute or two minutes long per episode when it
was first running. So the idea was let's try and
keep this to around five minutes an episode, and it's
two people. It was me and my co host, Chris Bollette,
who was my editor at the time, and as you know,
well I am a chatty Cathy. Keeping something to five
minutes is very challenging for me. And it was also
supposed to be referencing and existing article on the website,

(05:02):
and the goal was sort of a brand extension to
help drive traffic back to the site. As we all know,
getting people to convert from one form of media to
another form of media is challenging, particularly if you're talking
about podcasts to web.

Speaker 4 (05:16):
It can happen, but it's challenging.

Speaker 5 (05:19):
So we started doing this, but we realized one the
time format was not conducive to us having an intelligent conversation,
so we expanded to ten minutes, fifteen minutes, and then
eventually we were told go as long as easy to yeah, exactly.

Speaker 4 (05:34):
And then two.

Speaker 5 (05:35):
The other issue we were running into is that because
technology evolves so quickly, that if we were referencing articles
on the website, there was a chance that the material
we're referencing is already out of date. So we eventually
were allowed to move away from that as well, and
we would still touch on things that were on the website,

(05:55):
but we didn't have a strong mandate that every single
episode had to reference a particular article. And I think
that's where we actually saw the show flourish.

Speaker 3 (06:06):
And I think about you mentioned the early days and
some of the topics that would come in. I'm curious
in terms of the show development, what was the initial
goal or once you sort of moved beyond let's just
make sure that we're covering things that are covered in articles,
how did the mission of the podcast begin to take
shape in terms of how you saw it existing in

(06:27):
the world.

Speaker 4 (06:28):
It was very.

Speaker 5 (06:29):
Organic, and I think ultimately what Chris and I settled
on is that both he and I love to learn,
and then we love to share what we have learned
with each other and then through extension.

Speaker 4 (06:41):
To the audience.

Speaker 5 (06:42):
So the way that we worked back when he was
my co host is we would independently research a topic
and we would not share our notes, we wouldn't make
an outline. We would sit down to have a conversation
about what the topic was, and the conversation is what
would become.

Speaker 4 (06:59):
The episode of it.

Speaker 5 (07:00):
And because we both are naturally curious, and we both
love to share what we have learned. I think that's
what ended up becoming the kind of central mission of
tech stuff, is that the hosts love to learn new
things and they love to share that with you.

Speaker 3 (07:18):
I know that for us over the years that we've
worked together, the number of times that we've come to
you and said, Jonathan, there is this new topic in
the world, and we can't wrap our heads around it.
The first time people started talking about NFTs, the first
time people really started thinking about the world of cryptocurrencies.

Speaker 2 (07:37):
Of course, we're currently in a.

Speaker 3 (07:38):
Moment where everyone's trying to wrap their heads around the
future and capabilities around AI. What were some of those
first ones that you remember people coming to you and saying,
because I mean, so much has changed over these you know,
several years that you've been working on tech stuff. What
are some of the biggies that you remember people saying, Jonathan,
you got to help me.

Speaker 2 (07:58):
I have no idea what this even means.

Speaker 4 (08:00):
This again will give you a hint of how long
I've been doing this.

Speaker 5 (08:04):
Yeah, but a big one, and this is true, A
big one was cloud computing. Yes, there was there was
a time where no one knew what cloud computing meant,
right it was it was a buzz term, and no
one was really sure what that actually would mean. And
so I did episodes where I explained cloud computing, grid computing,

(08:25):
cloud storage, you know, which got into things like specific
brands like Amazon Web Services or Microsoft Azure and all
these sort of of things. And I feel like it
was really helpful at the time because a lot of
people were hearing these terms, but they didn't have a
deep understanding. And when it eventually boiled down to cloud
computing is it's computing, but it's someone else's computer that's

(08:46):
doing it, they started to get it. But like we've
had other examples too, big data is another one. You know,
big data was again for a long time, a buzz phrase,
and for a while, we were really good at collecting information,
but not so good at analyzing it. And once that turned,
once data analysis became more sophisticated, and we could suddenly

(09:10):
find a signal in all the noise of that data
that transformed everything as well. So anytime there's a new
technology five G is another great example. Anytime there's a
new technology, especially one that gets a big marketing push
behind it, having the ability to come in and remove
all those layers of obfuscation and marketing speak to get

(09:32):
to what the actual nut of the subject matter is.
I find that really satisfying.

Speaker 3 (09:54):
There's always these moments and culture and pop culture and
in terms of media coververage or something that hits you know,
whether we want to call it a tipping point, your
partner Malcolm Gladwell on some projects together, but or something
like that, where it is just part of everyone's conversation.
And of course what we're living through right now is
that conversation around AI and where it's heading. Do you

(10:18):
feel like you're usually pretty good at knowing when these
moments are going to come or do they ever take
you by surprise to say, you know, oh my gosh,
this went from talking about the future to suddenly talking
about No, there's actually a tremendous amount we can do
right now with this technology.

Speaker 5 (10:35):
It's amazing because there are times where I feel like
I'm simultaneously surprised and not surprised at all, and it's hard,
it's hard to articulate.

Speaker 4 (10:44):
But AI is a great example of.

Speaker 5 (10:45):
That because obviously, artificial intelligence is a discipline that's decades old,
and it covers an enormous spectrum of topics within the
computer world. Generative AI is obviously what most people are
focused on right now.

Speaker 4 (10:59):
It's the splash.

Speaker 5 (11:00):
That's just one application of artificial intelligence. So I wasn't
exactly shocked when generative AI kind of took center stage
back in like a couple of years ago, but I
was surprised at how quickly it did, because I knew
it was already a thing.

Speaker 4 (11:16):
We had already seen.

Speaker 5 (11:17):
Text to image generators out there, but the chat bots,
while they had been increasing in sophistication, hadn't really reached
the level that we would see with you know, chat
GPT for example. When that hit and then when everybody
jumped on it, that surprised me a little bit. I
don't think it should have, necessarily, because we saw the

(11:38):
same thing with an FTS a couple of years earlier,
and that what will happen is that everyone will hear
about this new thing. Everyone has the fear of missing out,
of being left behind, and so everyone's jumping in without
having a fully formed strategy of what they're actually doing
or even what they're actually trying to achieve, and everyone's

(12:00):
kind of flailing in the dark. Simultaneously hoping that they
get to the other side where the light is before
everyone else does. And it's a little comedic and a
lot scary at times.

Speaker 3 (12:14):
I see I can be a little of both of those.
So with AI in particular, and think about your world
as a podcaster and a communicator. How do you see
it changing your job? How do you see it changing
what you do on a day to day. What does
it look like to be a podcaster, especially in this
category a year from now, two years from now. I

(12:35):
know that could be really difficult to predict, but maybe
talk a little bit about that.

Speaker 5 (12:38):
It concerns me a little bit in the sense that
I would love to be able to use AI to
help me, for example, research topics and get a deeper understanding.
But at the same time I also know about AI's
tendency toward hallucinations and confabulations, which is where AI, when
it's faced with a lack of information, will vent information

(13:01):
and present it as if it were authoritative. It's like
if you opened up an encyclopedia and you didn't know
that the editor was drunk that day and just started
making stuff up when doing the entry on say ancient
Babylon and you think it's real, but turns out it
was all made up. That can happen with AI, So
it makes me a little nervous to rely on it there.

(13:24):
I see it as a potential wonderful tool, depending on
how you actually put it into use, Like I could
see ways of doing podcasts where you utilize AI for
an entertainment purpose and it could be phenomenal. I also
see it as a kind of scary threat for people

(13:45):
who are writers and even podcasters, because we've already seen
examples of AI that's capable, quite capable of imitating voices,
like if you have a certain amount and if you're
someone who I don't know has more than two thousand
podcast episodes under his belt, you have an awful lot
of training material for that AI to develop a voice

(14:08):
similar to your own. So it's one where I think
the potential is phenomenal, but it requires incredible stewardship to
be able to realize that potential without causing more harm.

Speaker 4 (14:22):
Then you get benefit.

Speaker 3 (14:23):
And finding those areas, like you said, of really trying
to be disciplined about it, areas where we can do
some things that we've never been able to do before.
As you know, having these conversations and really looking at
the technology as we have been for a couple of
years now around things like translations, you know, knowing at
some point we would love for someone who's primarily a

(14:47):
Mandarin speaker and someone who's primarily a Spanish speaker to
be able to listen to tech stuff and really trying
to get there and knowing that the technology has advanced.
It's definitely come along with There have been points where
we've evaluated and said, you know what, it's not there yet.
We needed it was at sixty percent. We want to
watch it get to seventy percent. Want to watch it

(15:08):
get to eighty percent and get to a place where
you can acknowledge it's not perfect, but it is great
to be able to give a listener access to a thing.
I'm curious about your your thoughts on that as well,
because it does seem like there's opportunities to do things
that just previously wouldn't have really been possible or sort
of financially possible to pull off in a scalable way when.

Speaker 4 (15:30):
It comes to accessibility. I'm all for it.

Speaker 5 (15:33):
When you're talking about inspiring uses of technology, ways to
use technology to increase accessibility to whatever you're talking about.
That always fills me with incredible hope and joy. I
love seeing.

Speaker 4 (15:46):
That, and so using AI in order to.

Speaker 5 (15:50):
Achieve those kinds of goals I think is incredibly noble
and I would love to see more of that. Whether
you're talking about translation or you're looking for ways to
deliver material to people who are differently able and may
not be able to enjoy a particular piece of media
the way most people do. I think that is phenomenal.

(16:11):
So I am fully behind those approaches. The concern I
have is when it gets to the point where the
AI is like, I'm gonna start making Mandarin tech stuff
episodes without that Jonathan Strickland person at all.

Speaker 4 (16:23):
That's let's just cut out the middlemand like.

Speaker 2 (16:25):
I got this, Yeah, yeah, exactly, Yeah.

Speaker 4 (16:28):
I know how to make puns and Mandarin. Let's just
do that.

Speaker 3 (16:32):
It's definitely going to be very very interesting to watch,
you know, And there's a lot of a lot of
really smart and fascinating companies that are doing great work
in the space that are evolving very quickly. You've actually
had the chance to work with some and to help
these companies sort of translate into you know, popular conversation

(16:53):
what exactly is that they're trying to do. And it's
been a great experience for these brands to be able
to work with like yourself and a great communicator like yourself.
Can you talk a little bit about those experiences working
directly with brands?

Speaker 5 (17:05):
Oh?

Speaker 4 (17:06):
Sure, Yeah.

Speaker 5 (17:06):
So, for example, in the House to Works Days, I
had a show called Forward Thinking that was in partnership
with Toyota. More recently, I've done a podcast called The
Restless Ones with T Mobile for Business, and I have
found that the beautiful thing is that when the relationship
is a healthy one, it's very collaborative because you all

(17:28):
have the same goal at the end of the day,
and that goal is that you want to reach the listener.
You want to be able to convey the message in
a genuine way, and you want to make sure the
listener knows that you're being earnest and sincere. To me,
the important thing is making sure that everyone's expectations are
managed and they're set at at the right level, and

(17:48):
that you're all working together toward that end. We had
so many conversations with T Mobile for Business about making
certain that the material we produce is meaningful to the
listener that it's not just trying to sell a message
to them to a potential customer.

Speaker 4 (18:05):
In order to.

Speaker 5 (18:06):
Make it something worth listening to, you have to make
sure that the material does have that sincerity behind it,
and sometimes that means asking tough questions. But if you
can't answer the tough questions, you can rest assured the
customers are going to ask that down the line anyway.
So it's better for you to get ahead of it
and to make sure that you're being honest, because I

(18:32):
know that you know this. We're raised in a society
where we're so surrounded by marketing and advertising and all
this sort of material that we can recognize in a heartbeat,
and we can tell when something is real versus something
is insincere or it's just an advertising message, because we're
surrounded by that all the time. And if you don't

(18:55):
take that into account and make sure that the messaging
you're crafting has meaning kind it beyond this marketing message,
you're going to fail. I mean, you might create something
that at the end of the day on paper, shows
that you met your obligations, but no one's going to
listen to it. So you want to make sure early
on in those in those relationships that you have these

(19:17):
conversations and you realize like, okay, we now know what
it is, we're presenting what we're trying to craft, and
we have have metrics to say whether or not we've
achieved that. It makes it so much easier and people
respect you for it.

Speaker 1 (19:31):
You know.

Speaker 5 (19:32):
Like I said, listeners are smart. If they listen to
something and they recognize that they're just being sold to
and that's it, chances are they're just going to check out,
even if they really like the person who's the host
of the show.

Speaker 3 (19:43):
Yeah, it makes sense, and it takes that partnership to
really get it right.

Speaker 1 (19:47):
You know.

Speaker 3 (19:47):
Fortunately, as you said, T Mobile for Business really got it,
really trusted you really were collaborative and figuring that out.
That's why we've done, you know, multiple seasons with them. Also,
I go back and think about, you know, Smart Talks
that we've done for several years now in partnership with IBM,
both with you as a host and a voice and
Malcolm Gladwell from our partnership with Pushkin, and it's just

(20:11):
been really fun to be able to create these shows
that yes, they're working closely with the brand and helping
a brand communicate many of their messages, but actually, at
the end of the day, just putting out something that listeners.

Speaker 2 (20:22):
Really enjoy it. It's not an easy task, but it's
been fun seeing that come together. But before I let
you go, Jonathan, I would.

Speaker 4 (20:30):
Love to hear what's on your mind this week?

Speaker 2 (20:32):
What are you talking about? What are you what episodes
are you working on?

Speaker 5 (20:35):
Yeah, so I literally just finished recording an episode about
discontinued operating systems. I know that's exciting, right, But really
the reason why I did it is because all the
really juicy drama in tech is behind the scenes most
of the time, and so if you're talking about things
like discontinued operating systems. In this case, I was telling
the tale of Next Step, which was the operating system

(20:58):
for the next computer, which was what Steve Jobs worked
on after he was essentially forced out of Apple and
the classic Mac operating system, which ended up becoming a
total chaotic mess by the nineteen nineties, which was the
reason they brought Steve Jobs back into Apple. That's one
of the reasons why I love doing tech stuff is that, yes,

(21:19):
I am talking about these nerdy techie things, but it's
almost a gateway into very human stories and you start
to understand, Oh, the reason our technology is the way
it is isn't just because of ones and zeros or
circuit boards and CPUs. It's because of the people behind them,
and sometimes the really messy altercations they would get into

(21:42):
while trying to forge what at that time was our
technological future. Now it's our past.

Speaker 4 (21:47):
And then you think, that's why my iPhone is like this.

Speaker 3 (21:51):
Yes, it's pretty wild, and I love being able to
lean on you for those stories. But Jonathan, I tell
you this all the time, but it's phenomenal what you've created,
and you know, for the millions of listeners who've been
able to rely on you for not only entertaining information,
but accurate information, it's been a real service for the

(22:12):
industry and for listeners. So congrats on everything you've accomplished
with tech stuff. Looking forward to another decade and a
half of tech stuff. I don't know if you're ready
to commit to that, but I know we would love
for that to happen. But yeah, thanks again for spending
some time with us today.

Speaker 4 (22:27):
Thanks so much, Will. This has been a real pleasure.

Speaker 3 (22:29):
That's awesome, and thank you guys for tuning in. We'll
be back again next week.

Speaker 1 (22:41):
Conversations is a production of iHeartRadio. You could find more
from the biggest names in podcasting on the iHeartRadio app
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