Follow the Geeks - CTO030

Machine-generated from the episode audio and not hand-corrected, so names and technical terms may be imperfect. The audio is authoritative.

Welcome to episode 30 of the CTO Advisor Podcast. com and the author of Follow the Geeks. It is an incredible series of 10 stories of technologists that followed, I would say, I would say non-traditional career paths or towards entrepreneurship, but I think it's becoming the future of work. There's a lot to learn in this career-focused episode. Hope you enjoy it. So Jason, can you go ahead and introduce yourself? Hey, I'm Jason Heiner. I'm the editor-in-chief, global editor-in-chief of Tech Republic and also long-form editor of ZDNet.

And I've written a book recently, Follow the Geeks, which is about 10 digital entrepreneurs, 10 digital innovators and the future of work. And so really passionate about that topic. And yeah, I write about business technology. Both of our publications focus on helping people who are using technology to get their work done and people who are trying to, we help them make good decisions about technology. And so that's the stuff we're passionate about. A lot of the times these decisions have huge implications for the person's career and for their company.

And so in that sense, we feel the responsibility to helping them be smarter and make good choices and all that kind of thing. So as a disclaimer, I'm a contributor for Tech Republic, which is where I actually know you from. From the most part, I think a couple of years, we met a couple of years ago at a event that CBSI hosted. And I was invited as an attendee and it's been a great relationship since. One of the things I don't get a chance to too often, I have to apologize for it.

I know you happen to be on the Twitter network quite a bit. Yeah. And one of the things that I found interesting was your passion for long form writing over on ZDNet. What's some of the cool projects you guys are working on over there? Yeah, I do. I do care about sort of in-depth reporting and original reporting. There's a lot of stories out there. There's a lot of news and buzz and overlap and all that. And so we're always trying to look for those stories that people aren't telling, that are important, that are significant, and that are being overlooked and places where we can go a layer deeper.

I write some of these once in a while, but even more so, I edit them, I assign them. I work with journalists on the topics to pursue and the things to do. So yeah, we've done a lot of really great ones. We had one last fall on NASA, how their 20 year experiment to use virtual reality to train astronauts, because it's hard to train people how to do something that they've never done before. And there's no place on earth here to kind of simulate it.

So yeah, we do a couple of these stories a month between ZDNet and Tech Republic. And they're always, always, you know, fascinating. We really are always trying to get at these with some original reporting and share some stuff with people that they can learn from and that, you know, lessons that they can learn from and hopefully apply to their own business. So one of the things that I really appreciate about your passion for long form, and I don't want to get too kind of journalistic on it.

We'll get into the discussion on careers pretty shortly, is that the hook into careers is that journalism has changed quite a bit. I was listening to, I think it was, it was a couple of shows on over on the TWIT network and they were talking about the number of trade racks that have folded over the past few years. And that's forced a change in journalism and a change in the career paths of many, many talented people that for probably good reason thought that they had careers for quite some time.

And so in order to do chase passions like long term or long form projects, you have to adjust to the current market. And I think ZDNet and Tech Republic are doing a great job of mixing kind of the short hit stuff that I do. And then the long form stuff that your team is working on. One of the things that I wanted to really talk about because you wrote the book, Follow the Geeks, which is, I hope we get a little bit of time to talk about the different way you approach writing a book, which I thought was really cool, is, you know, you had basically what, nine or 10 stories of technologists that pursued entrepreneurship in very different ways.

How did you get the ideal for the book? A lot of it was based on the fact that so many people I knew, their careers had been disrupted in one way or another. They got laid off from a job or they couldn't find a job in the kind of career they wanted, or they just couldn't quite do it the way they wanted to do it. They had a vision for the kind of storytelling or reporting or podcasting that they wanted to do and they couldn't quite do it the way they wanted to do.

So eventually, a lot of these people were reluctant as entrepreneurs. There were 10 of them and a lot of them were reluctant entrepreneurs. They kind of had to start their own thing just to be able to do it the way they wanted to do it. Part of my thesis was that the future of work's a lot more entrepreneurial and that doesn't mean everybody's gonna have to start their own startup. I think it does mean that, because even within big companies, big companies are looking for people to act more entrepreneurial, whether it's organizing into smaller teams based on project or changing even teams based on project, pulling people from different teams for projects and having them work together on little sort of task forces or temporary teams.

I mean, I've got a full-time job and so it's hard to have the time to write. So I had this idea and I pitched it to somebody that I was working with, Lindsey Gilpin, who at the time was working for me on the staff at TechRepublic. We were talking about books and we were talking about the future of work and all this. And I told her about this idea and I didn't really want to do a traditional book. And I said, but if I did it, I'd written some books before and it's really not a great process.

It takes too long and it doesn't often make much money, but what money it does make, like the publishers and the bookstores make all of it and the authors really don't get any, even though they sort of work tooth and nail for a long time. I was like, look, if I was going to do this, I would just release the chapters on the internet and then self-publish it when I was done. And usually everybody I told about this idea, they sort of looked at me like I was nuts and for good reason.

And Lindsey said, actually, that's a great idea. That's pretty cool. If you're going to do that, you should actually crowdfund it. That would be a really great way to sort of involve the audience in the whole process too. We released, as we wrote the chapters, we split the work. I also needed somebody to help me with the work and that's why Lindsey was really great. com. And when we released it, we also asked for feedback and people did everything from sort of crowdsourced copy editing to telling us things that were wrong and you need to be fixed or giving us more information or sometimes telling us, oh, that person was great.

Did you ever think of this person? You know, one of your first chapters, chapter one is on Baratunde Thurston, which I read his book, How to Be Black. You couldn't probably have started out with a better crossover person. And I was just captured from the beginning because as a technologist and as someone who needs to support their family, there's two parts of your story. One, how do you successfully self-publish a book? And two, as a technologist, how do I move, how do I protect myself from job loss?

You know, if you read the work for 2020 or any of the books in the future, kind of the future of work is, you know, you can look through all 10 of these examples and some folks, I think Veronica Belmont might be an example. I can't remember if it was Veronica or another one that went back and forth from being a entrepreneur to a full-time employee to an entrepreneur. And they just had this entrepreneurial spirit and I really, I personally related to that.

Yeah, it's funny. A lot of people have felt that way about Veronica's chapter because I think hers is really representative of a lot of people today who, because so much work is available through contract gigs, right, and she's taken contract gigs in different ways and sometimes had two or three different ones at a time and sometimes had one big one kind of going at a time. And I hear a lot of that from people like yourself that have experienced similar things and have done work that way.

In one of the chapters too, Chase Jarvis says, a quote to the effect of, our parents had one job, we'll have five, meaning like five different employers and our kids will have five at a time. Obviously they won't have five. Some people have meant like, oh, that doesn't sound like a very fun future. And obviously five jobs at a time doesn't mean you're going to five things every day, but a lot of them are project-based or different kinds of gigs that you have with different companies and some spin up and some spin down at different times and some overlap and all of that.

But the future of work is probably, sliced up in different slices in more efficient ways than it is today, or at least some of it is. And I think my career, I think has been representative of that journey in which, I think at the end of the day, you don't say that I'm Keith Townsend and I work for AtV or, it's a throwback a little bit that you have a trade, you have something that you offer. Chase, I thought was a great idea.

Me was a great example. He had these fundamental skills that he had. He was a teacher, he's curious, he's a artist and throughout all of his endeavors, he kind of kept those principles intact. And you look at the multiple things that he's done over his career to his current projects and you see a consistent theme. And I think that's, I think consistent throughout the book is that when you look at each one of these people, they didn't go off and do something that was fundamentally different than what they did from when they were full-time employees.

Even probably one of the most successful examples in your book, Leo is a radio guy. Yeah. And both Leo and Tom to varying degrees of success, they both were radio guys. And if you look at what they do today, it's very much like what they did outside of college. It's true. They just adapted for today's mediums. Yeah, adaptability is really key. That's one of the big themes I came away with from doing this book is the people that were and are the most successful in this that we learned about.

You're right, Keith. It's like they have this core idea of the work that they're most passionate about and they think they can do the best. But then they had this, they balanced that with this adaptability. They learn new technologies. They learn new ways of doing business. They learn new ways of interacting with their customers, in their case, their audience. And then the tools they use are different, are always different and always changing. And the methods that they use to interact with and interface with customers is always changing and really in a constant state of revolution over the past couple of decades.

But that core bit of who they are and what their mission is, they sort of is kind of constant. And I like that a lot. I feel like that's the thing that almost anybody can take away from this and apply to what they do in kind of whatever way. I gotta put the two hats on that. One, I knew you before the book and now I'm reading the book and it's just caveats that as I talked to you that are brought out.

And one of them is that what I really enjoyed the work that you and Lindsey did is that these are not all fluff stories. These are, I mean, some of these guys had really tough setbacks from Tom leaving the Twit network, folks getting laid off, to some people even getting fired from their jobs. And then some of them having failed endeavors and then coming back from it and going there. So it speaks to the journey, which is a career. And these are just snapshots of portions of their lives.

And I like that. We both wanted that to be part of the story. You know, they all had, those are a couple of the other themes is one, they all had big setbacks and sometimes really tough setbacks. You know, O'Malley, his story, like he made a big bet with GigaOM about changing the way media works and, you know, bet big and ultimately it didn't turn out the way he wanted. And we talk about that in there. You know, Leo had some really tough times getting to where he wanted in his career.

He talks about like, it took him, you know, decades to really get to do what he really wanted to do and be independent. You know, whereas you look like the last chapter, which is, you know, Maya Penn, you know, who was an entrepreneur from the age of eight, which is- That was amazing. Remarkable. Really, really remarkable. And for her, it just was that she didn't have any fear. You know, she didn't have any fear of doing it. And so, you know, those are really important themes, I think, was that, you know, but they have the, you know, people had setbacks, they had adaptability, they had this like core mission to what, you know, some of the things that they, you know, it's not always one thing.

Sometimes it's two or three different things like that they're most passionate about or they think the work that they can do best or the vision that they can bring to the world. But we, you know, bring those themes kind of throughout. And we wanted to, we didn't want to make any of their setbacks, you know, we didn't want to shuffle them under the rug. We wanted to let that be part of the core bit of the story because everybody can relate to that.

You know, everybody can relate to pain and setbacks and difficulties. It's just, you know, part of life. And so, and all these people landed on their feet, you know, they all found a way to land on their feet. And so hopefully there's some inspiration in that. Yeah, and I think at least for me closing out on comments, and this is a enterprise IT blog and podcast. And I think for folks who haven't bought the book yet, I think I highly recommend the chapter on Gina Trapani, who's probably the most relatable person from an enterprise IT perspective.

She's a programmer, she is, I don't think she'd be offended if we called her a geek. She is in a book called Follow the Geek. She is truly, you know, she's a computer science hack that if you follow kind of her, you know, she's a classic programmer who would like to be just in a corner off to herself. She exposed herself in a really wild way by creating Lifehacker. And now she's banging away at code again, doing what she loves. And the journey is really great and interesting.

And I think it offers a unique perspective for the enterprise IT audience. Yeah, I do think too for enterprise IT, Juliana Rodic, chapter eight, she, you know, did this work. She worked in enterprise IT with databases and she worked for a Sprint during the run up to the internet, you know, working on the internet backbone for them. She was an engineer at Sprint. And then she later goes off when she's from Kenya. And when, you know, things went bad there in that country, she and some of her fellow, you know, geeks and coders created this product Ushahidi, which was enabled people to crowdsource reports on violence as well as, you know, opportunities for aid and that kind of thing.

And then that project, which is this open source project has become critical to countries and governments and nonprofits and, you know, election agencies and all kinds of people all throughout the world. It's become one of the world's most popular open source projects. And so she's pretty remarkable too. But yeah, that's funny. That's chapter three is called the programmer, chapter three, the programmer and chapter eight is the engineer. And so those two are definitely for our enterprise IT friends, ones that they'll especially enjoy, I think.

Yeah, and I think for my fellow bloggers, you can't, you already talked about the own story. We all, I think how much we all bitterly miss the original GigaOM. I think a lot of us can relate to the pain of that story. And I think OM was extremely raw and it was just a really great recap of where he was at and where he's gone. So I couldn't recommend the book any more than I think I already have. I think it's not just a great book for technologists, but for people who want to get inspired and have a path forward to work if they need to work for the next five to 20 years, I think it's a must read.

So Jason, where can people find you? Where can they find a book? Where is it available? Yeah, cool. com. That's our site, obviously, which has information about the book, about each of the chapters, about all the people we cover in the book. com. You can read any of the chapters by, you can read the introduction, the opening to each one. You can also find the book on Amazon and Audible and iTunes, iBooks. You can find the paperback and the e-book on Amazon.

You can also get the paperback, the hardback, and the e-book on our site. You can follow, there's also on Twitter, it's at followthegeeks is the Twitter account. You can follow me, at Jason Heiner. At Lindsey Gilpin is my co-author, who did just a great job and is an amazing writer. Really, the two of us just poured our heart and soul into this book, because these are just some great people and some people that we learned so much from, and we just figured other people would, too.

Anybody that wants to think more creative about your career, that's who we were writing for. Well, I really appreciate it. For those of you who are not familiar with the podcast, you can find this podcast on iTunes. com, and that's it for episode 30 of the CTO Advisor. Thanks a lot, and have a great day.