Brian Bell (00:00.526) Hey everyone, welcome back to the Ignite Podcast. Today we are delighted to have Alana Karen on the mic. She spent 23 years building products and teams inside of Google across search, ads, fiber, and a lot of other things before stepping away to write and speak full time. She's the author of the best-selling Adventures of Women in Tech. I actually have the book right here. thank you, Alana, for sending it. now in its second edition. we're really excited to sit down with her. Thanks for coming on.
Alana Karen (00:27.301) Thank you, thank you for having me.
Brian Bell (00:28.984) Well, I'd love to start with your origin story. Like how do you end up at Google as employee number like thirty or whatever it was?
Alana Karen (00:35.717) Well, it was it was three nineteen. I feel like I always have to clarify. yeah, pretty early. We were in one building. I was like really on more of a artsy history path in college, but to date myself, it was like right when the internet was starting to boom. And I decided to teach myself
Brian Bell (00:38.862) Three nineteen, okay, but still it's very early.
Alana Karen (01:01.615) How to do like webmastery type stuff, how to make web pages. I did it for internships, I did it for school projects, way before my professors knew why I was doing that. And talked my way into my first job being a webmaster at the college I went to, University of Virginia, Wahoo Wa. And
Brian Bell (01:25.966) What is that? Is that what you do? Is that the rah rah rah? What is it?
Alana Karen (01:28.129) Wa that's yes, you you wahoo wa. It's like it's a wahoo. It's fish that can drink like more than its weight. So it's like a very college thing. But yeah, you wahoo wa. anyway, yeah, I mean it kind of just like that combination of like artsiness, but I could do it with my fingers like right in front of me and had been really familiar with computers growing up.
Brian Bell (01:30.765) Hoo.
Alana Karen (01:55.215) based on how I was raised. And so it just ended up all coming together. And then went down the startup path after that first job and my second startup was Google.
Brian Bell (02:11.341) Amazing. Do you looking back? I often think about this because I have kids about to go to college. Did your parents urge you to get any sort of degree or do you have any like regrets there and like to following your interests? 'Cause ki kind of where it led, like I think about this a lot. Do I kind of push my kids towards, you know, hey, it's really good to get a STEM degree or something like that, or just, hey, just major in whatever is interesting to you.
Alana Karen (02:33.419) Yeah.
Alana Karen (02:37.688) grew up without a lot of money and so I think that really it was like the pressure my brother and I put on ourselves to get out of that situation.
Brian Bell (02:49.803) Yeah. Same. I grew up poor too. So I was getting a finance degree so I could understand how money works. That was like my motivation. But nobody told me to do that. Yeah.
Alana Karen (02:52.087) Yeah.
Alana Karen (02:55.616) Exactly. Like you just you know, you wanna make a responsible kid. Give him scarcity. lot of anxiety associated with that, which is not great.
Brian Bell (03:02.945) Yeah. Yeah. yeah. All the stereotype threat of going to high school in the same clothes over and over again and stuff like that. Yeah. I remember all that. Yeah.
Alana Karen (03:11.574) Lot of anxiety. But but I think because of that, you know, there was definitely an intellectual snobbery coming from my parents. they both went to school, pursued masters, my dad got a PhD. And so while there wasn't a lot of money, there was a lot of intellectualism. And so there was that kind of like you you will go to college. Right. Yeah, yeah, yeah.
Brian Bell (03:34.231) Mm. interesting. That is an interesting dichotomy. Yeah. Almost a shunning of money. We don't need money. We have our minds.
Alana Karen (03:45.999) I sh no, not really. They they just weren't they just like literally weren't very good at making money. Like if my brother was here, he would be like, just to be clear. A lot of decisions were made. you know, I'll give an example. Like the my mom was working at a college, which meant we lived in a college campus dormitory growing up.
Brian Bell (03:47.931) Ha.
Brian Bell (03:58.05) Just to be clear, they're really bad with money. Yeah.
Alana Karen (04:15.777) And it wasn't like particularly fancy, but it was it was large and it was it was there, right? And free housing. She didn't make a lot of money, but we did have this free housing. and it wasn't in a great neighborhood. So they sent us to a private school. And then they didn't realize that they should be applying for financial aid. They sent two of us.
To private school over a half hour away for like a good ten years before my brother came home one day and he was like, This family that you think is middle class is on financial aid. Like you We have to like put things back in the grocery store because we don't have enough money. Like, go apply. So they're just like there were there was just stuff and like
You would say maybe it was pride, maybe it was this, but like they were like literally bad at completing taxes. Like they were bad at forms. They were they were honestly just kind of bad at being adults. It w you know, like you meet those like zany professors who can't cross the street, like, you know
Brian Bell (05:23.735) No, my my my wife's parent parents are like that. Yeah. Intellectuals, multiple degrees, k kinda bad with money. Sorry, Papaloid, if you're listening, but Yeah.
Alana Karen (05:26.969) Kinda that vibe.
Alana Karen (05:32.495) Anyway, yeah, yeah, exactly. Sorry, sorry, parents. they got somewhat better as they got older, but like way past helping us. so I think like I don't I don't know. I don't have that, I didn't feel very pushed by them, except like I knew I wanted to college, I wanted to get out, I wanted to be more responsible and like figure my crap out. I think when I look back at college though, I got attracted a little bit too much to like some niche.
Brian Bell (05:41.186) Yeah.
Alana Karen (06:03.146) subjects, you know, some some PhD students pet project. And I do sort of regret that I didn't just go to like the main famous professor class, you know, like just like you know there's a there was a guy teaching civil rights history at University of Virginia, Julian Bond. He was like part of the movement. He was a famous professor and I was like, I learned about the civil rights
I just kinda look back and I'm like, Sometimes you go to the professor everyone says to go to. Just go. Anyway.
Brian Bell (06:39.797) Really advice. Yeah. So if you yeah, if you hear of a class, if you're listening and you're in college and you hear of like an amazing class that you must you must take, probably probably go tick it. Yeah.
Alana Karen (06:48.896) Just take it. Yeah, like don't be all like we'll be boring 'cause I already learned that. No. L listen to the guy tell his in his deep booming voice voice his his beautiful stories.
Brian Bell (07:01.665) Yeah. Well, let's get back to the Google journey. So you said you plan to stay at Google for at least twenty years. Why did you why twenty? Why not fifteen or twenty five or what is that twenty year thing?
Alana Karen (07:09.124) twenty three.
Alana Karen (07:15.028) At the time, that was basically, you know, as as Google got older, there was like no one who could have been there 10 years, and then there was no one who could have been there 15, and then there was no one that could be there 20. And so I was in that first class of people who could even hit 20. And so I think in my head that was kind of the dinger because
There were only like a few people who were realistically gonna hit it before me. I think when I left and you didn't I think there were less than 30 people more tenured than me, and that included Larry. Yeah, I think that included Larry and Sergey. So like it ch you know, like they're only so early you're gonna go. so
Brian Bell (07:54.113) Yeah, by the time you left, I mean, you must have been like you weren't in
Right. That's where the number thirty came from, I think, in my head. I remember reading the background. Yeah.
Right.
Alana Karen (08:12.484) I just at some point it became the round number. I think also in my head I thought age-wise
Like when might you leave? And I had thought in my head at any given point, you know, some someplace in my forties was old enough, someplace in my mid forties was old enough, some place in my late forties was old enough. and at some point I was gonna try to hit 50, but then it just didn't, you know, the way the cookie crumbled, like this mixture of things.
Brian Bell (08:25.845) Yeah.
Brian Bell (08:45.761) Yeah. It's so weird because I I'm having the same thought. I'm I'm in my mid forties now and I'm kind of thinking about retirement already because VC funds are so long that I'm like, okay, if I start another fund, it's really 15 years, you know, maybe twelve before it's really wrapped up. And I'm forty six, right? So I'm thinking, okay, when do I really want to be wrapped? I love what I do. I I can't imagine retiring, but I'm like, what year do I actually want to stop doing all the administrative stuff that I'll I'll need to do in the future?
Alana Karen (09:13.582) Well and I think in this I think this is what a lot of us are sort of thinking about in our forties, going into fifties, is just kind of like what is enough anyway? Like if we were to some degree successful.
How much more or when is enough?
Brian Bell (09:34.187) Yeah. What does another decimal really buy you at this point, right? Yeah. Another comma.
Alana Karen (09:37.57) When is enough enough?
Alana Karen (09:43.693) You know, on the other side, if you're not at a place of stability yet, what would it take to get there? Right? Like how much more energy, appetite, interest, like all of these things do you have for whatever you're doing? I think some people like never want to stop working, but even if you never want to stop working, what does that look like? Does that still look like eighty hours a week? Does that still look like a full time job or
Brian Bell (09:49.601) Right.
Brian Bell (10:12.545) Yeah. I don't think I'll ever stop investing in startups. I I think I'll I could literally be like eighty years old and investing in startups. but I I wouldn't work I wouldn't do it fifty, sixty, seventy hours a week like I'm doing it now, right?
Alana Karen (10:13.795) Anything.
Alana Karen (10:20.236) Right. But do you run your own fund?
Alana Karen (10:26.05) Right. Right. And yeah, so if you're asking me why not thirty, I frankly just was like running out of juice. Like and and right when I was feeling like, ooh, like am I old enough for you to give me that corner office and like just believe that I'm smart and like listen to me, Google decided to be like, well maybe old timers sucked the whole time.
And we were bamboozled and being too easy on everyone. And now it's the AI era. So everyone needs to reprove themselves. And so we were just in like different places. I was like, no, no, no, no, sweetums. Like this is when you trust that I was actually good the whole time. Like, this is not where you decide to retest me. and you know, I think if if there had been something really interesting or new to learn or
Brian Bell (11:07.127) Yeah. I've been I've been here twenty years, right? Yeah.
Brian Bell (11:14.498) Yeah.
Alana Karen (11:22.274) a really new opportunity, but really a lot of my job had become about adulting for the company, right? Like who are we gonna keep? Who is gonna get laid off next round?
Brian Bell (11:35.415) The the people conversations. P people people don't talk about these, or at least I don't hear people talk about them how how brutal the people conversations are internally. Like how political. Like at least it was at Microsoft, right? it was yeah. So brutal.
Alana Karen (11:51.596) Alana Karen (11:55.001) Like I would say that for like the first set of years, it was political just in the way where like everyone wants their thing, but their hearts are in the right like it's just that like you're all going in and you love your person. And so like you're angling and you're this and you're that. And there is some out, you know, there is like who's the favorite of that person? Like, they always get listened to, like, how do I become the favorite? Right. Like there was always a little bit of it.
But then when scarcity set in, you know, post-COVID and the company is trying to make off trade-off decisions so it can invest in AI, then the cutthroat, then the survival came out. Then the like, I will lie about you and say that your team sucks because that will get me more territory. Politics came out. And
Brian Bell (12:27.213) Mm.
Alana Karen (12:52.664) You know, that was not my game. I was
Brian Bell (12:55.213) I had a friend of mine that was, you know, probably not a senior as you, but he he left around that same time. Kind of right post COVID. He said the whole the whole culture shifted and he was just tired of it.
Alana Karen (13:05.892) You know, I think that there there is still it's still one of the better places to work, I think, because there is still this like really nerdy still for the pursuit of the best outcome, the best product. i I'd still think you would walk in from other businesses and be like, that's a weird set of decisions you're making. Like, don't you wanna make money? Like
Brian Bell (13:30.625) Yeah, I talk I and I talk trash about Microsoft. It's still like if I had to take a corporate job and I and make a living, Microsoft's a great place to work. Yeah, it's a great place. Yeah. Yeah.
Alana Karen (13:35.094) Right. Like, don't you like money? Like, there's still so many things like that. But I will say that this like the fear set in and the the real like what happens to our human brains, we go like animal brain and we think everything's a threat, everything's a risk, we act out of fear. Like you really saw that set in in this era where people didn't know who was gonna get fired.
Brian Bell (13:58.382) Mm.
Alana Karen (14:03.556) They didn't know what was gonna get cut. And so the best thing was just to always be
Brian Bell (14:14.593) guard, yeah, you kinda change. Yeah. Yeah. Yeah.
Alana Karen (14:15.338) On guard, yeah, I don't yeah, I don't have a better like on guard and maybe like more than just defensive, like always on the offense. Right, like always angling, always yeah.
Brian Bell (14:23.113) yeah. Watching what you say and how you say it with who you say it with. Yeah. So in twenty nineteen you started actually publishing real performance feedback you received, including comments that stung. Tell us tell us about that.
Alana Karen (14:37.74) Yeah, you know, I've always liked writing. You know, back to my artsy thing. I always liked writing and I was coming up on a a time in my career where I'd just gotten through kind of a crazy year where I'd built a team that I'd inherited, but I went from like ten people to thirty people. At one point they all reported to me before I brought in another director. Just had been kind of a crazy year. And finally I was gonna get it all set up and like I knew I had some breathing room and I was like, ooh, I'd like to write a little bit.
And I put out this article series. I think, I think like sometimes when you're writing, you're just like, where's the material? What do I have a lot that I can work with? And I had all of these years, probably like you, of performance feedback from Google. And so it's just this like really nice base to like kind of go through chronically and say, like, well, at first I wasn't as or chronologically, not chronically, sort chronically.
But go through and say chronologically, like, okay, first I didn't do communication really well. And then it moved into people management. And then it moved into how you lead and strategize. And I just thought, I don't know, maybe it'll be interesting to other people. So that's why I went down it. And I I don't know, some people called me really brave for sharing the performance feedback. I don't know. Like for me, it was sort of like,
I don't know, got this thirteen years ago. Like it's not like you're gonna be like, I'm a bad communicator now. So it never really maybe like doing it later in my career when I had more confidence was the good timing on it. Cause yeah, while it had stung at one point, by the time I was writing about it, I felt very much distanced from it.
Brian Bell (16:26.19) So the that series became the seed for the book. when did you know you wanted to actually write a book on this?
Alana Karen (16:33.762) I think I'd put out that series and I was getting a lot of comments on it that were just sort of like, we never hear these stories. We like, we never hear the struggle or like the underbelly of what it took to build a career. And I looked around, I looked at the books that were posted in both the women in tech category, but just sort of generally. And there is a there isn't, it's not that there isn't.
Books or stories out there.
Brian Bell (17:04.27) Yeah, there was lean lean in was kind of the fur one of the first big ones, I think, right?
Alana Karen (17:08.34) Yeah, exactly. And I think that the issue was that often they were written by people that then people didn't see themselves in. They didn't align with. And like there'd be this joke. I would hear it like actually kind of repeatedly, you know, at a conference or whatever, like I would be talking about this issue and someone would say, you didn't wake up at 5 a.m. to do hot yoga. There was just like this idea of like
The people that we've read about have habits, lifestyles, privileges, possibilities that I never had, I'll never have. And therefore, for better or worse, I have trouble taking their advice. Okay, I have trouble like really thinking it relates to me.
Brian Bell (17:57.327) Yeah, when you're writing from Sheryl Sandberg's, you know, point of view, it's like yeah, you're like you've had a completely different journey for most people. Yeah. Right.
Alana Karen (18:02.404) Listen, I I knew Cheryl, I worked for her at Google. Like I knew she wrote it with the best of intentions. But like it sh the that advice that she gave was really what she would say in the room. Like you would walk in and you would sit on the edge of the room and she would be like, get to the table. Like she really did that. She wasn't making it up. And it was from a place of true of truth and and having seen it work and help people. But still it didn't always you know.
resonate for everyone. So yeah, the idea for the book came to me in sort of a rush, like right around that sort of period where I was publishing articles, but also having these conversations where I just wanted to write something where I interviewed a lot of women across all kinds of types, backgrounds, tech, non tech, ro but roles in tech companies, so that people could see like, you could do it. and yeah, there would be hard days, but you could do it. And I guess I was kind of annoyed too.
Just I felt like there were a lot of stories at the time that were sort of like, you know, news articles with titles like Can Women Be in Tech?
They can be attacked me.
Brian Bell (19:12.462) That's funny. So what tell us about the book. What's what's in it? You know, some of the insights and anything that surprised you in the process of i interviewing so many women and and writing the book?
Alana Karen (19:23.19) Yeah. I mean the first edition that I released in twenty twenty really was focused on these eighty different women I interviewed, their stories with this idea that like you could pick up the book if you were worried about whether you should join tech, if you were already in tech and you needed a feeling of belonging or
ideas about the path forward or just like you needed companionship, right? Like you could pick up this book and there would be something in there that resonated with you because I'd interviewed so many different people. Like you would you would certainly be able to feel like it was achievable for you and get some practical advice. In writing the book, I think two things surprised me. I think one was that
My original plan for it is essentially what you see. The chapter structure that I wrote wrote in the book proposal is exactly what you see. And I think that was really like when you write a book after like almost 20 years of collecting information in your head, like you kind of know what you're doing. And so, or just reassure people, if you have a book idea in your head, like you can do it. Like it's there. You pr trust yourself more than you think you can.
Even if you've never done a book before. I think the second piece that surprised me was
At the time, a lot of the talk had been about how many women we were losing and how hard it was to retain women. A lot of focus on the baby making years, or also the like harassment or toxic environments, etc. And when I interviewed all these women, I mean.
Alana Karen (21:28.16) I didn't find that many women who were planning on leaving. I didn't find a lot of women who were struggling in that way. Right? Like when I asked them what attracted them to tech, they would talk about the opportunity to grow, the opportunity to improve their life situation monetarily or otherwise, the people they got to work with.
feeling like they worked amongst people that got them, kind of their clan, their tribe. and certainly just like monetar like money. and when I was sensing weakness in these women, it was all about those things. Not about the baby making years necessarily. Like you had to plan around them, you would think about them, you would adjust your expectations, right? You'd get support.
Whatever you had to do, it was definitely a whole thought process for them. and not so much about hostilities. They kind of accepted or moved as needed to avoid that. But what was really kind of happening was what we've seen over time was like, is the opportunity there anymore? Is this what I thought it was gonna be? Do I keep just getting moved to different managers? And I don't really
feel like my work matters, right? Like it was that kind of stuff. And I don't know I would say that that totally surprised me because obviously I'd been picking up on it. But I do think it surprised me how little what like the news media was picking up on like why we lose women was really what any of these women were talking about.
Brian Bell (23:19.02) How so?
Alana Karen (23:22.158) I think it's sexy to talk about things like that. And it's less sexy to be like, maybe there's just bad managers and and we don't have a high enough bar for good management. I think it's
Brian Bell (23:33.166) Right.
Brian Bell (23:39.534) Well, everybody's o that's the Peter principle, right? Everybody's always like their at their level of incompetence. I mean, I certainly was when I was at Mike. Like, you're always promoted to like just the edge of your capabilities. Like Yeah.
Alana Karen (23:45.098) Right.
Well, and we know that a lot of truly smart technical independent contributors were made managers because they were tr truly smart technic you know, independent contributions. And so like you picked your highest performers with the idea that they would pass that knowledge on. And you know, maybe if you truly showed zero interest in other humans or hostility, you didn't you didn't get slotted. But like there wasn't
you know, a test for it. And in fact, it was kind of under appreciated or calibrated what the skills of a good manager would be. And and you know, like that that meant that the early people put in management then chose all the next people.
So you kind of end up with endless fun there. Yeah. And I think just also it was the Me Too era around when I was writing in 2020. And so there was just like the general outrage and stories emanating from that period. I think it was really important that those came out, but I think that it also overindexed the news on that type of issue and less so on just like, like.
Twenty years in are these women still getting what they need? Is anyone still getting what they need?
Brian Bell (25:14.55) Mm-hmm. So your new edition. So I don't I don't know how many years we're in between the editions, but it argues a lot of the DEI and work from home programs flopped since twenty twenty. Walk me through kind of why you wrote the second edition and what kind of broke between the two editions.
Alana Karen (25:27.532) Yeah, so I wrote it about
Totally wrote it about five years later. Kind of this idea that I would do a fifth anniversary edition. But I would say that pretty soon after I published the first one, I felt the lack, I felt the gap in what I should have talked about. because I really didn't I like very much focused on the women and their journeys. And I focused less on the systemic issues in
the tech working environment. And so I wasn't really criticizing the systems around us. I just was sort of like, well, here's how you navigate through them and here's how you like, and you know, I would acknowledge them. I didn't ignore them, but I also wasn't really talking about the system very much directly. And, you know, right when I'm publishing this book, we've got the George Floyd murder. We've got the
Other we've got like riots happening because of other systemic injustices, you know, mainly towards black people. But then you get into I mean, we've kind of forgotten about that there's all this Asian hate during COVID, right? Like that's still part of what's happening all around us. It's just sometimes there's stories and sometimes there's not. And in tech, and I think you probably saw this at Microsoft too.
Even if you kind of subtracted that, there was also kind of a system happening of who got promoted and who didn't, who got to leadership roles and who didn't, right? Like who got the salary increases and and why, and like all of these dynamics at play. And I didn't really talk about them. And so coming up on the five-year mark, I already kind of had that in my head. But then you also had.
Alana Karen (27:27.736) The post-COVID layoffs, you had AI, you had just like the overall changing of the tone of these companies towards kind of a harsher, harder world, like, you know, good times are over. Now everybody fights for their jobs, right? Perks reducing, work increasing, right? This like real hard tone shift. And I felt
Brian Bell (27:56.643) You actually called this the hard tech era in the book, I think. Yeah.
Alana Karen (27:59.064) I did, although I have to admit, a New York Times writer whose name is slipping my mind, I credit him in the book for for saying this for the first time. And called him it he called it the hard tech era, partially because of this kind of sh shift in leadership tactics and tone of the companies, but also
Brian Bell (28:10.126) You call this out, yeah.
Alana Karen (28:26.327) the real shift in investment away from software towards hardware to fund AI, right? So like a real like hardware shift, if you will.
Brian Bell (28:35.874) Yeah, the scarcity has shifted down the stack to the electrons and and and atoms. Used it used to be software was the limiting factor, and now software is tenx faster to create. And so that's shifting the dynamics probably internally, right?
Alana Karen (28:39.093) Right. Sacrifice the people by the machines kind of thing.
Alana Karen (28:49.283) Well it also you'll remember it used to be like sorry, I tucked over you. what I was gonna say, it also used to be that like if you asked if you asked a company like who what is your lifeblood, like a tech company, they would say engineers. And that did mean that people who weren't software engineers felt like second class citizens. So there was that problem.
Brian Bell (28:55.169) No, no, me too.
Brian Bell (29:09.356) Right. Software engineers. Yep.
Brian Bell (29:16.534) A little bit, yeah.
Alana Karen (29:18.817) However, the engineers, super special. Now, if you ask them, they might still say that, but it's with an asterisk, which is that they're replacing them. Like they are willing to fire the engineers to buy the machines to hopefully replace them. And that is just a very different vibe. for everybody, right? Like now the second cliff citizens feel even worse.
But also the engineers for the first time, like the entire tone of the company, right? Like the engineers are scared too. And the engineers are fighting for their jobs. And it used to be kind of annoying sometimes as a non-engineer that your engineers were felt so safe and secure and whee, like, no, get things done. You're like, nope, I need you to get it done. but like to have everyone act from a place of fear.
Brian Bell (30:06.158) Yeah, they're coming at eleven o'clock and yeah.
Alana Karen (30:17.262) How do you ever get back that vibe of, we're in it together and like it's the beauty of the products we create? You can't, right? It's a totally different world. Anyway, so long story short.
Brian Bell (30:25.036) Yeah. Well, growth is also a panacea when you're printing cash like like Google was during that its heyday, and it still is, it's still printing cash. but now, like you said, they're spending most of that free cash flow on capital expenditures to build out the the machines, yeah, the AI.
Alana Karen (30:33.034) totally.
Alana Karen (30:42.552) Machines.
Yeah. And so long story short, I just really felt like I needed to write, not just for women, like for anyone picking up this book who's like struggling with this period of time and this abrupt shift. I needed to write this edition because the first book had been incomplete without it anyway. And now there were so many people kind of reckoning with this fairly abrupt shift in how they felt like their value was. But also
Do they even like these companies anymore? Do they believe in what they're doing? Do they believe they're good for the world? Right. Like there was all of this other stuff going on that I think for a lot of people actually felt like emotional, like and kind of heartbreak. And maybe for the first time in their careers.
Brian Bell (31:32.152) Hm. So what's a popular idea about fixing tech culture right now, that you think is wrong?
Alana Karen (31:46.276) That there seems to always be this idea that the purest
Truest best technology comes from
Five to ten people in a room cranking it out twenty four seven.
Brian Bell (32:09.954) Two pizza team team model Amazon, right?
Alana Karen (32:12.696) Right, never sleep. Sleep when you're dead, full hearts in it, no space for anything else. You're like crazy if you have a family to go home to. Like where's your dedication?
Brian Bell (32:32.686) We're all making sacrifices.
Alana Karen (32:35.492) yeah, for the for the purity of it. For the good of like why what do you mean you don't there's no strategy here? Word it for the love, for the belief. and if you see CEOs are really struggling with with that right now. Like they want their cake and eat it too. They want to be able to fire whoever they want, say whatever they say, basically say that they're okay replacing you.
But then they're also like, we can't find good people anymore who just believe. It's just a really weird era. And so the CEOs of large companies are struggling because in their hearts they still believe in the two pizza model and they can't get back to it. And then the small companies are doing it to the best they can do it. But like
It is just kind of flawed. It was just I mean, and you know, since you're an investor, like it works a small percent of the time, just like all things work a small percent of the time. Like, for like the one Google, there were thousands of bros in kitchens not washed, cranking away.
Brian Bell (33:44.75) Yeah, low single digits, yeah.
Alana Karen (33:58.403) Right. And so I I just think the minute times got tough, you liter like I literally saw sat through leadership meetings at Google where they rolled out what the AI team was doing as best practice. And all it was was startup mode. Literally was like, have a small team.
Brian Bell (33:59.597) And dozens of search engines.
Brian Bell (34:23.938) Founder mode.
Alana Karen (34:27.492) Everybody does w everybody does one thing and knows what they're doing. Everyone's in it, dedicated. You don't confuse them with meetings. And I'm like, why am I looking at a at a a slideshow about this? Like, I didn't
Brian Bell (34:41.214) I like that.
Brian Bell (34:47.4) I'm literally in a meeting about the thing. Yeah.
Alana Karen (34:50.072) about the thing. And I did it twenty years ago. Like and it had gaps. Like you burn out. You burn out hard. A huge percentage fails. You're probably
Brian Bell (35:00.322) You're a mercenary anyway, right? You're expendable. Apparently in the in the hard tech era. Yeah.
Alana Karen (35:03.352) You're probably not paying attention to laws, to laws or other things. Right, like there's just some stuff that like is super flawed about that thinking, especially because it worked twenty, thirty years ago when there was a lot less eyes on you and legal laws about what you were doing, and like all legality type things, regulations across countries, like all types of things.
being like it worked then and we lost it as like your answer
Alana Karen (35:39.813) And like some people would say, but it did, right? Like we jammed those people in one building and we got Gemini out. And like I can't argue with it that you pr produced some like you jammed a whole bunch of humans and you made them miserable and a whole bunch of them had to go on health leave as a result. And you got it and you didn't care at the price, and that's fine. Like I I don't know how to argue with you that something you did worked.
But you saying that's the only way, that's the right way There is no other possible way to get to your outcome. I don't know about that.
Brian Bell (36:17.326) Hm. Yeah, I mean Microsoft's built a two trillion dollar company on thirty five hour work weeks.
Alana Karen (36:24.428) Well, some people would argue that that could have been optimized.
Brian Bell (36:28.462) so you said principles only mean something when you hold them at inconvenient times. So is there a moment recently where holding a principal actually costs you something? Or a company something?
Alana Karen (36:42.424) That is from a movie. Yeah, it's a movie quote. and I loved it. Yeah, principle yeah, yeah, you basically like principles are easy to have when you don't have to apply them, basically. I'll I'm trying to think personally. I mean, I do think that there are
Brian Bell (36:55.074) Times are good, yeah. Yeah.
Alana Karen (37:09.316) places in my career where I could have like made more money or
Alana Karen (37:18.98) profited in some way, whether it was monetarily or not, if I sort of had lower
personal standards for myself. Nothing too recently. but you know, I did I never leapt to another sort of sure thing startup that was growing that was gonna, you know, the Facebook is one that like I knew people at and I probably could have made the leap. And I didn't because I just never cared for the business model.
I was basically always the person that was like, yeah, if it started rating women, I'm pretty sure it doesn't get better. You know, like I was just never a believer. And weirdly enough, apparently, I sort of need to be a believer. Like I can't just I think that is one place where the principles got in the way. Like maybe they're
Brian Bell (38:18.606) I literally got on Facebook the other day, which I never do anymore. And, you know, like all the old folks are there, right? All my, you know, parents' generation and stuff, even grandparents' generation. And so I'll get on, see what's going on. And and I literally went to the the timeline. And I mean, it's just random content and ads. And like only one out of ten pieces of content are literally from people like that are friends and family.
Alana Karen (38:26.274) Right. Yeah, yeah, yeah.
Alana Karen (38:40.196) Mm yes, yes.
Yeah. Yeah.
Brian Bell (38:48.096) One out of ten. Like literally, I'm like, Nope, not not interested in that. And I I'm telling the algorithm like, nope, don't show me that. Don't show me that. Don't show me that. And it's this it
Alana Karen (38:57.198) Like, wait a second, we gotta make money off of you. What do you mean?
Brian Bell (39:00.428) Yeah, what are you into right now? You know, have you have you seen this new diet thing, you know? Or like whatever it is, right? It's basically become yeah, it's basically become like like the worst part of like late night commercials. That's like Facebook. I would describe as like like one twenty in the morning random commercials.
Alana Karen (39:02.896) Yeah.
Alana Karen (39:06.456) Whatever it is that it's it's tracked to, yeah.
Alana Karen (39:17.004) Yeah. Yeah.
Alana Karen (39:25.91) Yeah. And I I think like, listen, like these companies have their business models, but I would also argue, and I do in my book, like part of our problem is sort of what capitalism expects. Like we like to blame the tech companies for sacrificing their values or going back on whatever their lofty original visions were or whatever.
And I don't think we often be like, yeah, but you made them report out on a quarterly basis and you expected twenty percent year over year growth or else. And
Brian Bell (40:09.518) Yeah, it's w rule of forty really. So it's forty percent if you are at zero percent profit.
Alana Karen (40:16.164) Well yes. I I think I anchored a twenty percent because Google at growth, it was very clearly twenty percent. But yeah, yes. You you expect you expect that, and at a certain point it is nearly impossible to do and have whatever like meet everybody's moral bar. But certainly even at a certain point, a squinty moral bar bar, right? Like
Brian Bell (40:17.11) Or twenty if you're at twenty percent EBITDA, then twenty percent. Yeah.
Brian Bell (40:23.424) Right. For startups, yeah. Yeah.
Alana Karen (40:45.956) And and then you're like sh sh for shame, for shame. No, like they're reacting, these CEOs are reacting very much to what standard they're held to. And at a certain point, you know, at these larger companies, they are larger than some countries. They're holding a major position in the US economy.
major in the S P, like all of this type of stuff. Like they can't play around, you know, it's all ads now.
Alana Karen (41:26.794) You don't want to pay them to like log into Facebook or do a Google search or do a simple AI query or like whatever it is. You don't want to pay them. So what what are they gonna do? Well, no, I meant I said simple. Do a simple AI search. Yeah. Of course, if you're if you're more and you're leveraging more, and with most of these companies, there's a paid model. If you're a more
Brian Bell (41:39.842) I I I pay for open AI. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah.
Alana Karen (41:54.682) But the vast majority of the public just uses the free products. And then, you know, at a certain point, they're gonna try to squeeze every cent they can out of you. I don't know if you've tried to play games on your phone, but like it is a heavily interrupted enterprise if you don't pay eight bucks or whatever to get your way out of ads. And so at some point you're just kind of like, Well, how what's my time worth? Like
Brian Bell (42:16.066) Right. Yeah.
Alana Karen (42:23.918) And do I have the money to pay for this, right?
Brian Bell (42:25.154) Yeah. I pay f I pay for ad free everything. YouTube red, you know, everything. Just everything's ad free wherever possible.
Alana Karen (42:31.597) Yes. Well and you know, a lot of times you get into these whether we like it or not, like if you if you use a lot of the products you'll you'll buy some kind of bundle that gets you multiple like I don't know, because we have YouTube TV because we have YouTube TV, we get the bundle of things that includes do do do do do. And so like you just have to kind of decide. Amazon Prime comes with all this stuff. Like, do you do you want Amazon music? Doesn't matter, you get it.
Brian Bell (42:44.482) Yeah. Well well I hear I hear MySpace is starting back up.
Brian Bell (43:02.206) they charge extra for that now too. I just noticed
Alana Karen (43:05.22) yeah, maybe I'm just getting like thirty day free notices.
Brian Bell (43:08.48) It used to be ball bundled. Amazon music and Prime video, all that stuff used to come with it. And our credit card we had to switch our credit card 'cause every year like somebody steals it and we have to change it. And so I had to go I was going to watch a prime movie or video and I'm like, wait, it's not included? I have to upgrade to watch this. Like what what? When did that happen?
Alana Karen (43:28.261) Well and also they've done all these deals, I mean, to get into these business models, right? Like s all you know, you want you want like one thing on Paramount Plus. Like they'll show it to you, but then they're like, nine ninety nine more like no
Brian Bell (43:38.796) Yeah. Right. My trick there is I will I'll do the conversion, I'll I'll I'll do the subscription, the ten bucks or whatever, and then I just cancel them immediately.
Alana Karen (43:49.262) As long as you're willing to keep track of it. Absolutely. Like it all comes down to what is it worth? Like going to a movie at a movie theater is X dollars. So like if you wanna see The Martian or whatever when it first comes out, like what what are you willing to pay?
Brian Bell (43:51.532) No, I just cancel it immediately. I sign up and I cancel the like immediately.
Brian Bell (44:06.956) Right. So anyway, your your new materials digging into these AI driven career shifts that we've been talking about help the audience understand what a woman now, like in her tech career, should be optim optimizing for, given how fast the ground is moving right now.
Alana Karen (44:23.939) Yeah. Well I would say a woman or anyone, really. I don't know that this is I don't know that anything I'm gonna say is I don't know. We'll see if I say anything gender specific.
Brian Bell (44:27.724) Yeah. A human in tech.
Alana Karen (44:38.053) There's the obvious shift, which is that a lot of job applications at this point expect a certain level of AI fluency or usage, whether it's central to your role or not. They're expecting the efficiency of that to be baked into what you do. So do you have you spent any time with any of these tools? And now like
They're pretty much everywhere to some degree in software that you might use for something else. So have you looked at what is baked into Canva, for instance, if you're a designer? Have you looked at what's baked into recording studios like this or to script, right? And are you making use of that to make your work more efficient? And are you fluent with that?
Then there's the level lower. Like, do you know what these tools are doing? And do you know how they work and their flaws? And can you do you have a fluency of that to help companies make better decisions about how they're using AI? and what it means for their corpus, their body of information. How are they protecting it? How are they?
leveraging AI to bring them more users potentially all of those kind of things because now like just like there was search engine optimization, there's AI optimization. So there's a whole like enablement piece that now I think also will be a not insignificant amount of opportunity or potentially a person's job.
And then there's the even deeper stuff. Like, is your job replaceable or completely changed by the existence of AI? And are you going on that journey or not? Now, I will say it's really interesting if you look at something like software engineering, because some people I think are really enjoying that AI can maybe take over some of the tedium.
Alana Karen (47:02.552) Of coding certain things or problem solving for certain types of issues or whatnot. Other people are missing that element of puzzle solving, of ooh, let's like figure out what's going on here and let's let's figure out how it really works and make it better. And so I think different people are gonna have different reactions to it, but.
I guess I would just say don't ignore it, right? Like figure out where you stand on it and start to make the adaptations accordingly. because you don't want to have your head in the sand and then get laid off and have no plan B. And I think that's certainly possible now. I think like we're in kind of the seesaw now of this sort of overfired before AI was ready. And so, you know.
But just assume AI will keep improving and assume you have to work according.
Brian Bell (48:04.524) Yeah, and I I think that's what people aren't really prepared for is how good it will get in the next few years. because now it's it's yeah.
Alana Karen (48:10.276) Well, I think it's always hard to tell. Right? Like I think I think for the lay person it is it is hard to tell.
Brian Bell (48:15.5) Well, they just don't think exponentially, right? So they're just, you know, they're thinking like, okay, well, it was this good last year, so next year it'll be a little better and like, no, it's like getting ten X better every year.
Alana Karen (48:26.446) I'll give an example from just yesterday. I was like in my car, like hood up. Rats had chewed through the wiring because it is apparently yummy. have car manufacturers solve that. Like, hey, you could just by the way, plenty of problems to solve around the world that humans have not solved yet. And one of the ones you could solve is
Brian Bell (48:37.123) Mm.
Alana Karen (48:56.128) Is the yummy wiring in cars. and so I'm in there with this special Honda tape. Honda makes it. Only Honda, pretty much, makes this capsicum infused tape so that you're the rack goes in there and it's like, it's spicy. Well, eventually they still chew it. Absolutely. But this is just like we're deterrent, we're in deterrent land right now. And I'm in there and I took a picture.
Brian Bell (48:59.01) Alana Karen (49:26.006) Of what my car looked like. And I said, Hey AI, where should I reinforce with this tape? And it gave me a description, which is essentially what I expected. And then I went back and I said, Can you mock up the photo with where I should do it? Now you and I know.
That was risky. Was it even gonna give me back the same car? Like like was what was gonna go down? And it did. And that is better than last year and and absolutely impossible two years ago. So I do think and by the way, I pay w it's bundled with some I don't I get Gemini paid free. So it is possible if you tried to replicate this on the free version, maybe not, I don't know.
but Gemini Paid gave me a mocked up thing. And I think yeah, people are maybe underestimating
Even like situations like that. And listen, did that replace anyone paid that I would have paid for this? No. Cause I'm cheap. I wouldn't have like rolled back into the store with that tape and had a mechanic do it. But it did replace me clicking around 17 different sites, giving them impressions, maybe clicking on ads. And so, you know.
There's an ease to every example that I think we use AI for and then what it offset that I think maybe we're not truly understanding the magnitude of that shift over time.
Brian Bell (51:16.472) Right. Yeah. Well let's wrap up with some rapid fire questions or wrap up questions. what's something you believed with total conviction back when the first edition came out of your book that you'd now argue against in the second edition?
Alana Karen (51:33.806) think in the first edition I would have said if you want a career in tech, it is a good place for you and you should go for it and just know that there are some
problems she'll have to deal with.
That's still somewhat true.
I just would maybe add a fifth thing that, like, hey, it's weirder and way harder than it was before. And there might be a time where you look around and you actually think there's something better. But when I in 2020, I wouldn't have said, you're gonna find that much better. Like, so if you want it, go for it. And now I'm just a little bit like, ooh, like the companies are.
Cutting versus increasing. And there might not be that exponential opportunity for you that there once was. And there may, in fact, be like, don't marry tech and never look around. Like, keep your eyes open because there might be something in the medical field, which is just way more opportunistic given how medical needs are growing in the US, right? Like something in
Alana Karen (52:57.028) actual physical manufacturing because that can't be replaced, right? Like as easily anyway, yet. So I don't know. I I think that that's a place where now when I talk to people, I just I want them to look broader than just tech tech.
Brian Bell (53:16.822) There's a whole other economy out there. Yeah.
Alana Karen (53:18.68) Well in lots of places now, you know, you go you fast forward twenty years, lots of p jobs now leverage tech no matter where you are. Whereas it used to be you had to come to tech to work on tech. So I think that's evolved anyway.
Brian Bell (53:34.68) What's a what's a question you wish interviewers asked you about your career but never do?
Alana Karen (53:43.716) I don't people ask me so many questions.
Alana Karen (53:50.752) I think that people gloss over maybe how hard it is and like don't ask enough about like
Alana Karen (54:02.264) What were like really awful things no one talks about?
I think you know what I mean. Like they sort of like they focus on the tech or they focus on leadership or funding or like, you know, like like a lot of the and then like you're like, well that's not really what made any of it hard. and so I think maybe we under focus on like what makes I mean even any job, but like certainly these tech jobs so difficult.
Brian Bell (54:36.76) So given everything we talked about with the kind of the hard tech era, trust breaking down in in tech, how do you personally decide whether to trust someone or some company you're gonna work for?
Alana Karen (54:51.544) I think that I like to look at their track record and you know what what have they funded, what have they believed in? Who have they taken risks on? Right. So like their track record both with like business decisions but also talent decisions, right? Is is their full staff?
The guys they shared a suite with in college? Or have they looked around a little? Like it can still be two guys, right? Like you can still have your favorite people, absolutely. But did at some point you go out and look for the best person for this? Did you go out and look for an adult? And I think I've had that for a while. Like,
Ever since my first startup failed, when I joined Google, I was like, they just hired Eric Schmidt. They brought in an adult. Right? Like, I want to see that you made the hard decisions at some point. I think that basically is it, right? Like, what's your track record? And then, you know, once we're working together, do you do what you say? And if you don't, then I'm gonna.
Figure out something else.
Brian Bell (56:16.91) Is there a particular piece of feedback, negative or positive, about you, maybe from your ser your your series on LinkedIn and that you particularly remember or had impact on you?
Alana Karen (56:30.189) Alana Karen (56:33.765) I think I mean all of it obviously did I think that over time the people management feedback, that switch from individual contributor to really figuring out how you're gonna like coach and care about people was something I took like very seriously in my career and probably had the most impact on me. However, I will say the feedback that I got in spots over my career that I should be more ambitious.
has made me I think really reckon with who I am and what I expect out of life. And I think maybe it's interesting if you grow up without a lot of money, what what you think of as a big deal or like what how big you imagine and where you unintentionally sort of set your limits. I think it's made me at least sort of reckon with that part of my character.
even if I don't always pick the most ambitious thing. it makes me like be like, am I not asking enough? Am I not expecting enough? Am I not seeing enough? And I should talk to other people to broaden what I do.
Brian Bell (57:50.712) Yeah. When you're gone, way in the future, hopefully, what's the smallest, most specific thing you hope someone remembers about you?
Alana Karen (58:02.637) The smallest most specific
Alana Karen (58:11.151) think I think something I said that resonated with them really because at first I was thinking, she's hilarious. Which I do think I do think I'm hilarious. but if we're thinking like specific, I just think whatever it is, like that moment, that thing. And I find that it's never and I don't know if you've had this experience in your career, like you'll have a meeting with someone, you'll have thought you're brilliant, you'll be thinking about something else. And they'll come to you later and be like, when you said that it really struck me.
And it's never you don't even remember saying it's not what you thought. And it just goes to show you like different people are gonna take different things away. And so I just hope I hope something I hope it's something specific, not just like, she was nice or whatever. You know, like just something like, remember when she did X. I'd love that.
Brian Bell (58:40.268) And you barely remember saying it, yeah.
Brian Bell (59:00.738) Hmm. Well, really enjoy the conversation. everyone go out by the book, Ventures of Women in Tech. where can folks find you online?
Alana Karen (59:10.185) the books on Amazon or on my website, alanakaren dot com. I'm on LinkedIn. I'm sure you'll put that in the show notes and Instagram and Substack. I have a whole Substack I post you weekly.
Brian Bell (59:22.968) Great. Fantastic. Thanks so much for coming on.
Alana Karen (59:25.839) Thank you for having me.
