White Collar Crime (part 2): Interview with Jakob Kerr

On today’s episode, Brook and Sarah are joined by Jakob Kerr, author of Dead Money (2025) to discuss white collar crime and its place in mystery.

Discussed and mentioned

Dead Money (2025) Jakob Kerr

Michael Clayton (2007 film)

Shudder Island (2003) Dennis Lehane

Sharp Objects (2006) Gillian Flynn

About Jakob Kerr

https://www.jakobkerr.com

Instagram: https://www.instagram.com/jakob_kerr/

For more information

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Transcript

This transcript is generated by a computer and there may be some mis-spellings and strange punctuation. We try to catch these before posting, but some things slip through.

Sarah	Welcome to Clued in Mystery. I’m Sarah.
Brook	And I’m Brook, and we both love mystery.
Sarah	Hi, Brook.
Brook	Hi, Sarah. We are very lucky today to have an interview episode with Jakob Kerr. And Jakob is a writer and the author of Dead Money. In addition to his work as an author, he is a lawyer and communications executive in San Francisco’s tech industry.
Brook	He was one of the first employees at Airbnb and spent a decade shepherding the company from tiny startup to global phenomenon. Jakob has also been a bartender, sports writer, and for one disastrous afternoon, the driver of an ice cream truck. After 15 years in San Francisco, he recently returned to his native Pacific Northwest, where he now lives with his wife and children. Welcome, Jakob.
Jakob Kerr	Hi there, thanks for having me.
Brook	Thank you so much for coming on. We’re really excited to talk to you about your new book and also, you know, white collar crime in general.
Jakob Kerr	It’s ah one of my favorite topics. Always happy to talk some white collar crime. Sure.
Brook	Excellent.
Sarah	I think white collar crime can be more interesting sometimes than what we think of as traditional mysteries.
Jakob Kerr	I agree. It gets a bad rap sometimes. There’s not as much, you know, it’s a little bit harder to capture in a story, which I think we’ll talk about perhaps. um But I, you know, the stakes are really high. The the the money figures are super high. There’s a lot of danger and and violence involved in its own right. So, I think it can be fun for mystery.
Sarah	Well, let’s start by talking a little bit about how your background at Airbnb and working in Silicon Valley influenced your decision to write a thriller that was set in that world.
Jakob Kerr	Sure. Yeah, I was you know very fortunate to spend over 10 years at Airbnb. I was one of the first employees there. Um and my takeaway from my time in the tech industry has been this: Outside of royalty, I don’t think any group of people in human history has been treated better than the average tech employee. um You know, my wife works in hospitals and healthcare.
Jakob Kerr	And at the end of every day, we’d exchange work stories and it would just reinforce how strange my office was, you know, ah closing down for two weeks during Burning Man and Prosecco and kombucha on tap. And, you know, a lot of the color that’s in my book, Dead Money, is just pulled straight out of my real-life experience. um You know, a ball pit in the office and massage therapists. And we had a full-sized Airstream trailer where you could, you know, do conference calls, right.
Jakob Kerr	So this very kind of larger than life over the top setting. There’s a lot of sort of, there’s this kind of like gauzy sheen of optimism in Silicon Valley. You know, there’s like the cartoony logos and the silly names and there’s glass everywhere and the California sun beaming down.
Jakob Kerr	um But at the same time, there’s so much money at stake that all of that sort of optimism is juxtaposed against this undercurrent of ambition and greed and billions and billions of dollars at stake.
Jakob Kerr	And I always just sort of thought in my mind, wow, that could be a really nice tension to play with and an interesting dichotomy in which to set a mystery thriller story.
Brook	Yeah that’s wonderful I love the reference to like cartoony. Like it there there is that feel to it isn’t it?
Jakob Kerr	Oh, for sure. And also, I mean, you know, it’s just it’s the it’s the shiny logos and the silly names. um You know, the the main company in Dead Money is called Journy, J-O-U-R-N-Y. No E because you you can’t spell it normally. That’s against the rules.
Jakob Kerr	But yeah, I remember when I joined Airbnb very early on, ah you know, several of my friends were like, that’s the worst name for a company I’ve ever heard in my life.
Jakob Kerr	And you know iwas kind of hard to disagree. I think Airbnb turned out just fine. but um you know it it it does. Some of the silly names and the logos and stuff contribute to this kind of bubbly feeling that I think sometimes causes people to underestimate the level of power and ambition that, you know, lurks inside the industry. I think people are gradually becoming a little bit more attuned to that.
Jakob Kerr	um But yeah, I always just felt like this is a really nice tension at play. And, you know, I’d I’d be in meetings where it’s just all glass and sun and you have your iced coffee on the table and people are talking about really serious stuff.
Jakob Kerr	And in the back of my mind, I would think, wow, this, you know, there’s there’s a weird tension here. It’d be fun to play with.
Brook	Yeah. Well, your main character, she’s a lawyer. Her name is Mackenzie Clyde, and she’s tenacious and very complex. Did you have a specific inspiration for her character, and how did you approach developing her backstory?
Jakob Kerr	Yeah, I wanted Mackenzie to feel like an insider outsider, right? Someone who is very well versed in the tech industry, immersed in it, but who internally still maintains a certain distance or perspective, right?
Jakob Kerr	um She doesn’t, you know, she she sees the highest echelons of power and wealth um but she doesn’t have access to those things personally, right? She doesn’t have the leverage that a lot of the the power players in the Valley do.
Jakob Kerr	um So I wanted that to be kind of the protagonist’s positioning. And then i really, it was very important to me that As the story went on, and we sort of deepened Mackenzie’s backstory so that you could understand what makes her an outsider. And if she isn’t you know super fond of many of the tech bros that she’s surrounded by, why is she in this industry? What is her backstory that kind of drives her perspective?
Jakob Kerr	What has occurred in her life that makes her so ambitious, right? um So that that was kind of my formulation for her. In terms of points of inspiration, I don’t think there were any that were sort of top of mind while I was writing her, but I do think ah you know a movie like Michael Clayton, where he’s kind of this you know fixer character who’s got sort of has some depth to his personality, um those sort of characters kind of weighed in my mind, I think, even if I wasn’t thinking about them directly.
Brook	Mm-hmm.
Sarah	Well, and and just to build on that, you know, you’re talking about some of the darkness in ah the tech industry, and we see some of that through Mackenzie’s eyes, right, as an outsider, um some of her reactions to some of the some of the things that she sees.
Jakob Kerr	Yeah, I think McKenzie reacts to some things in the tech industry the way most normal people would react.
Brook	Mm-hmm.
Sarah	So, mixing technology and white collar crime with mystery risks coming across as being a little bit boring. There’s either info dumps, talking down to the reader, or talking way over their heads. How did you avoid this in your book? Because I think you do a great job of of avoiding that.
Jakob Kerr	ah Thank you. I really appreciate that. I think what I tried to do was just root everything in the characters, right? Like bring everything down to a human level. um And, you know, I think it’s interesting that most cultural depictions of Silicon Valley, whether it’s, you know, movies or TV shows or books, I think frequently they kind of stop at the beanbag chairs and the quirky founders walking barefoot around Manhattan, right? And it’s totally understandable why you would focus on those because they’re ridiculous and very entertaining, right?
Jakob Kerr	um But they’re just based on my experience within tech, there are so many more layers to the industry. And there’s this silent hierarchy. Mackenzie references it in the book, this kind of silent her hierarchy where money is diffusing everything.
Jakob Kerr	And that you know is always sort of front of mind for people as they operate within San Francisco, within the tech industry. I wanted to kind of dive deeper into those layers. um And in terms of making it feel you know visceral or still entertaining while you’re talking about things like corporate control or you know shareholders or who owns a company and who doesn’t, I tried to just bring it back down to the personal stakes of each character.
Jakob Kerr	And then also really… you know, focus on some of the interesting settings that there are throughout the tech industry beyond just kind of the offices and people on their computers. You’re exactly right. Nobody, I mean, there are some movies or shows or books that do a great job of people just operating in the digital world. But I think I wanted to get it, you know, get McKenzie and the other characters out from behind a screen, put them into some of the crazy places that exist within the industry, right?
Jakob Kerr	You know, courtside at a Warriors game has its own very unique parade of wealth and personality it’ streaming in. um Burning Man, as we referenced before. The weird sort of networking intensity of a tech conference, right?
Jakob Kerr	That’s a very distinctive scent of desperation in my experience. A founder’s home, right? You know, a tech founder’s house looks a little bit different than the average, you know, rich person’s house, right? They they do things in slightly different way.
Jakob Kerr	So I tried to kind of root it in some of the entertaining settings and then, you know, really convey the breadth of characters that exist in the Valley as well, right? It’s, um, because there’s so much money int tech, it’s this magnet for really ambitious people from all over the world. So you have your hippies, you have your tech bros, you have your type-A lawyers, you have your, you know, ah high school dropouts working next to Harvard PhDs shoulder to shoulder on the same project. Right.
Jakob Kerr	So trying to bring in the range of character as well, I hope would just kind of add some depth and entertainment to, you know, a core some core mystery mechanisms that are a little bit heavy on like, you know, oh, financial stuff and and corporate, you know, maneuvering, right?
Jakob Kerr	That stuff can be entertaining if it’s all channeled through characters that you find compelling and that are, that are you know, interesting.
Brook	Absolutely. I’m I’m curious, Jakob, of what your um tech colleagues thought of the book. Like you seem to have a real knack for being able to look at this from the outside and like have a larger perspective. Did your coworkers and colleagues have that same feel? like Could they see the value in in looking at the industry you know this closely?
Jakob Kerr	I think the vast majority of people working in the tech industry understand how ridiculous it can appear, right? um You know, most of my really good friends and close colleagues I worked with at Airbnb, we all understood, you know, this is, this is not real life in many respects. Right. Um, I think we all understood how fortunate we were to be working within an industry that really treated its employees as well as, as it did.
Jakob Kerr	Um, and also we’re able to kind of maintain a healthy perspective from some of the ridiculous over the top stuff that happens. Right. Um, So the reception to the book within the tech industry has been really positive. I also think there’s an element of that, which is everybody just loves to read about themselves, right? You know Narcissism trumps all. So it’s ah that’s that that’s probably a piece of it as well.
Jakob Kerr	But um generally speaking, you know I’m sure there are folks out there who have read Dead Money and maybe taken some affront to how I poke fun at the tech industry. But I haven’t heard from those people because I don’t like talking to those people anyway. And that’s just kind of how it is.
Sarah	We recently recorded an episode about writing twists, and that’s something that your novel is being praised for. Can you share a little bit about your process for plotting a twist that audiences love?
Jakob Kerr	Sure. And kind of three thoughts here immediately spring to mind. One is in terms of organizing the twists or plotting them.
Jakob Kerr	You know, I’ve, I’ve always heard this term for different styles of writers where there are, um, gardeners and there are foragers, right? Um, the gardeners have their plot of land. They decide where everything’s going to go. They put the seeds in and then then they watch it grow.
Jakob Kerr	The foragers wander off into the forest and kind of see what they find. Um I’m very much a gardener. I think that that’s just the way that my brain operates. Um I think every writer, you know, has to take a little bit from each category, but especially for a story with a lot of twists and a lot of layers to it, I felt it was really important to have a robust, solid outline before I started. So, I spent a lot of time working on that.
Jakob Kerr	And you know, definitely deviated from it as I got into the story. I think any gardener writer would tell you there are times when you get into the story and you get to the next thing in your outline and you’re like, oh, that’s terrible. Like, OK, I’ve got to change that. So, you know, it’s not all preplanned.
Jakob Kerr	Um I think the second thing I would say is that regardless of how good your twist is or twists are, you need to start with character. um That’s something that I’ve kind of learned the hard way. No matter how amazing a twist is, it’ll feel hollow if it’s not built on a really deep foundation of character work, right?
Jakob Kerr	um So that’s that’s another thing is, you know you can’t really start with the twists. You have to start with character, put them in these settings, see where they go, and then kind of figure out, you know, how to how how the twists might play with it.
Jakob Kerr	And then the last thing I would say is i think the best twists, the ones that I have admired the most, um you know, I think some examples are novels like Shudder Island or Sharp Objects. um They don’t just change the plot. They really cause the reader to rethink everything that they’ve just read or really kind of emphasize or change the theme and underlying messages of the story, right?
Jakob Kerr	In my mind, the best twists are ones that don’t just kind of ah create like a ah right turn in the plot, but they make me rethink what the entire story is about, right? Like, oh, I thought that this book was about X, Y, and Z. And actually it’s the whole time under my nose, it’s been a story about this instead. um Those to me are always the most fun.
Brook	Well, I want to say that um I think that you definitely achieved that. And this is one of the first times in a really long time that when I finished the book, I started it again. Because what you did at the end, I was like, oh, now I want to watch that. And… um So, you know, I think you did a fantastic job and without giving anything away, obviously, I love the scene where um your characters are talking about the nesting dolls, because I think that’s a really wonderful metaphor for for plotting and, um you know, what you think it is, but there’s layer after layer. So um I just really enjoyed really enjoyed Dead Money.
Jakob Kerr	Thank you. ah Yeah, I appreciate that. And the, the sort of narrative metaphor you just described with the Russian nesting dolls that are kind of hidden inside each other. That’s exactly what I was just talking about with sort of, you know, the best twists are ones that kind of show you that there’s been another story hiding within the one that you’ve been reading, right. And that’s, that’s sort of what I sought to create with Dead Money.
Brook	Well, with Dead Money being your debut novel, will you continue to set stories in Silicon Valley or are you planning to tackle a different industry or theme?
Jakob Kerr	I’m still planning to keep writing about Silicon Valley. I think there’s a lot more rich territory to mine there. um You know, one thing I’ve been thinking about over the last couple years is that I think, you know, movies, books, TV shows, sort of cultural fiction, they tend to follow the money, right? Especially within the thriller or mystery genre, right? So in the 80s, you had, it was the peak of Wall Street, right? And you had all these movies and and books um set within New York, set within Wall Street, set on sort of like this burgeoning financial industry, right?
Jakob Kerr	Then in the 90s, it kind of shifted to big law and you had John Grisham stories and you had these real life ah court cases that were resulting in judgments worth hundreds of millions of dollars. Right. And that’s you know, that’s where kind of the money was flowing. I think over the last few decades, the money has shifted into tech. And I think, you know, that’s now where the stakes are the highest. That’s where the most money is floating around that people can try to grab a piece of.
Jakob Kerr	um And I think we’ll see more stories consequently that are set within that industry. um The other sort of compounding factor there for tech in particular is that, people can just fall into money in tech, right? You don’t have to sort of work your way up the ladder for 20 years as a, you know, a junior banker who then becomes a partner.
Jakob Kerr	You know, people, if they’re in the right place at the right time within tech, they can get just get rich really fast, even if they don’t deserve it. And I think that that just dials up the intensity. Everybody’s sort of aware of that, right? Everybody in tech knows, “hey, you know, maybe my hand isn’t the greatest, but if I play my cards right over the next two years, like I could end up in a really good spot, right? There’s there’s a, i have a chance.” And I think that that just dials up the intensity of everything. So I still find the the setting and the atmosphere to be really compelling. And I hope to write, you know, more stories set within it.
Sarah	That’s so great to hear. Um and and I think you’re right. I think there’s probably a lot that can be taken from it. You know, I think about some of the bigger white collar crime stories of the last ah decade, and a lot of them have come out of um Silicon Valley, right?
Jakob Kerr	For sure. That was one of my inspiration points for Dead Money, honestly, was, you know, I was working within tech and in the mid 2010s, you had this run of companies and founders that were coming under a lot of scrutiny for how they were operating, whether that was Theranos and Elizabeth Holmes or WeWork or Uber.
Jakob Kerr	And the founders of these companies just became, you know, these really polarizing figures. And I remember thinking to myself, you know, I had grown up reading Agatha Christie mysteries and just tons tons and tons of mystery and thriller novels.
Jakob Kerr	And I remember thinking to myself, “you know, if one of these founders was was murdered, there’d be like a million suspects because they’re, you know, everybody’s after them right now.”
Jakob Kerr	And it was kind of like a light bulb went off in my head. I just realized, wow, you know, that’s a good that’s a good kind of concept for mystery because ah they’re in the spotlight, the stakes are high, and there’s a wide range of people who have motivation to to do so you know do something nefarious to them. So and you’re absolutely right. And that was that was a sort of jumping off point for some of my ideas for the book.
Brook	Well, Jakob, thank you so much for joining us today. Could you tell our listeners where they can find you online?
Jakob Kerr	Sure. My personal website, www.Jakobkerr.com. That’s J-A-K-O-B-K-E-R-R.com. I’m also on Instagram, Jakob underscore Kerr.
Jakob Kerr	And yeah, you can find my work pretty much every bookstore out there and Goodreads and all of the internet. So yeah, that’s where to find me.
Sarah	Wonderful. It’s been such a treat to speak to today, Jakob, and I’m looking forward to whatever you release next.
Jakob Kerr	Thank you. The pleasure has been mine. I really appreciate the time.
Brook	And thank you listeners for joining us today on Clued in Mystery. I’m Brook.
Sarah	And I’m Sarah, and we both love mystery.