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B
Well, I wish that was the case, but we did okay. But at the same time, you know, I think everything that's going on with AI and everything that's going on with employment, with jobs, with careers, I just thought it was too big of a challenge and opportunity not to get back in the arena.
A
All right, so, Shay, for those who don't know, little bit of your origin story. You're a Jersey boy.
B
Jersey guy.
A
I think you were, like, into gaming and engineering. So tell a little bit about, like, what happened in your career. You and I met around when you were starting boxed. That's right. Let's just start about how you, like, got into your work life. What happened next, and just give a quick down and dirty origin story for us.
B
I started my career as. Yeah, as crazy as it sounds now, as an English teacher. So I was. I was a teacher then I ended up becoming a corporate attorney. And then, you know, as the iPhone first came out, a few friends from high school, and I just thought, hey, let's make games for this thing. And we eventually created our own studio, video game studio that was acquired and then after that, did E Commerce at box for almost 10 years. So it's been a real career journey for me.
A
And. And why did you do that? Like. Like you're an English teacher. Like, okay, wait a minute. Like, I'm gonna be a corporate. Because I'm a smart boy from New Jersey, and that's what we do. We're either going to be doctors or lawyers. Like, what was the. What was the lawyer thing?
B
It was one more added kind of tweak to what you just said. And plus, A tiger mom that said, hey, it's time for you to be a doctor or a lawyer or a banker. And I thought, probably going to law school and being a lawyer is probably the only shot I have at any of those three. That trifecta, as much as I joke about it, that's probably over 50% of my motivation was, you know, just to make my parents proud and do what they wanted me to do.
A
Shea, you know that Mark married a tiger mother.
B
Oh, man. Do you know that I'm more of a tiger dad than she is a tiger mom? Oh, man.
A
He has adopted what he needs to adopt of that Chinese tiger mentality. And she's a little bit more. She is a little bit more. I don't know. Do you think that that tiger mom thing is more of an immigrant thing? Because as opposed to, like, I don't know, like, Amanda does not have that vibe. She doesn't have that vibe at all.
B
And her parents were not that way either.
A
So I wonder if it's like, I don't know, like, she has it for herself, but not for Theo.
B
Not for Theo. I'm definitely more the tiger dad for sure.
A
100%. All right, all right. So you go to your corporate attorney. We do Boxed, a really cool e commerce company. You did go public. Did you go public through a. An offering, or did you go public through. Through, like, back door?
B
Oh, we went via spac, and that was probably quite a mistake that we made. You know, I think when we had gone public, it was quite a direct way to get into the public markets and quite a kind of hot way to get in. But by the time we actually went through the process, it. It took longer than a traditional kind of S1 process. More scrutiny. And so, yeah, and you had all the SPAC overhang after you went public. So, you know, I'm not sure if I would do that again, but. But, yeah, you know, we went through one of the SPAC routes.
A
And then what happened after that? How long did you have to stay at Boxed before you could break off and do something? Your next iteration?
B
You know, we were public for several years before we went public. And so I was there until the every last day that we were a public company. And my days kind of. You can imagine, from the days when we first met Jill to the days of being a public company CEO, you know, the responsibilities and just my day to day didn't even look like what it looked like when we met. Certainly didn't look like what the days looked like when I was in the Garage fulfilling our first order. So it was a real, a real evolution.
A
Let's get to Pelgo. Here we are. Tell us a little bit about how this happened for you and what this company does and then we'll go into a little bit more of the AI
B
stuff over the last few years. I was at the, you know, after Box, I ended up at the World Economic Forum for, for almost two years. And one of the folks I met there was a gentleman named Frank d', Souza, now my co founder. But before co founding Pelgo with me, he actually co founded now a big company called Cognizant, which is a big Systems integrator, Fortune 500 company. And we just wanted to do something together. And so we started to really look at the landscape and we try to compare notes on what we both believed were going to happen in the world. And I think, you know, we started, I think it was the fourth or fifth article that we passed back and forth about how AI was going to impact jobs that really got our attention. And so we just thought we're all racing towards this AI future and there's all these AI opportunities and AI tools out there and people making so much money on AI and the shift. But you know, it seemed like an afterthought. It seemed like just folks proselytizing that. Oh yeah, and AI is going to displace hundreds of millions of people from their white collar jobs around the world. I would really think of, okay, where's the next part of the article about what we're doing for those folks? Or how are we kind of creating a sort of a safety net for them? And I couldn't find one. And so we started to ask each other, well, what happens if, let's just say we go to 15% unemployment in the US because of AI who's out there really trying to solve that kind of migrate folks over to more AI first jobs. And we couldn't find too many, too many companies there. And so we thought we had to
A
tackle it, but it's so new. How do you know, when you say AI first, how do you know what that means? In other words, I look at this, I feel like we're in this massive transformation and we're in the of that point process. We're so early on. So, you know, like I read that Harvard Business Review survey that found that all these companies that are not actually hiring, it's not because they're, they're replacing jobs, it's just they, they don't know. They know that, you know, I have 10 people doing the work right now, we're pretty sure there's only going to need to be 5 or 6, but we still need the 10 today. And we don't know which of the, which of the people we should not have. And so it's like the anticipation of AI is, is causing that low hire sense across many of the, of the services industry. But how do you know what's going to be needed?
B
I wish we had five hours and several drinks because I could talk about this for such a long time. I'd say probably the most salient example I can give in answering your question, Jill, is that just look at us today. If you rewind back to the advent of the Internet and you told folks that this thing might take away jobs, I think some folks can squint and say, okay, I can see how that's the case. But then if you said, fast forward many years, there's going to be these things called podcasts and that we're going to record them and that that will be a huge way of distribution where hundreds of millions, if not billions of people around the world every year listen to these things called podcasts. I guess 99% of people would say, I don't believe you, but here we are. And look at the amount of jobs and the amount of jobs that you'd be laughed at in 93 or 94 if you said this was going to be a full time job. It just, we just can't predict it. And I think that's going to happen here. AI is going to destroy jobs, but over time, I think between human ingenuity and human need, there's going to be a lot of jobs created that we don't even know today, or that we couldn't even make up if we sat here for five hours and just wrote down every potential job we think it could create.
A
So what is Pelgo attempting to do?
B
We're trying to bridge that gap. So for example, as folks potentially are displaced both involuntarily and voluntarily, especially if you hone in on the involuntary side of things, what do most folks get these days on the way out of a company? One, you get generally cobra. If you had full time, if you had insurance, you'd probably get insurance via cobra. Two, most likely some sort of severance, especially if you were in a white collar job. And then third, if you're generally, if you're in middle management or above, you get this thing called outplacement service. They help you with your resume, career pathing, someone to Talk to. But that's largely reserved for executives and folks who are more highly paid because some of those services cost thousands of dollars. With LLMs and with the ability to actually provide that type of advice these days via AI, there's no reason why that should cost thousands of dollars and there's no reason why that shouldn't cost a few bucks a month. And everyone transitioning in their career should have access to that. So first and foremost, that's the first product and the first module that we built.
A
And so how do people actually access with what you're doing? Like, what is it? What's going to happen to me, let's say tomorrow and I get kicked to the side of the road by CBS News? Let's say that I understand that, you know, nobody really wants someone like me, a 60 year old woman late in career. What do I need to do and what do you, what's the process like, what's actually going to happen for me?
B
Yeah. First, Joe, this is a quite an implausible example because you know, CBS loves you and we all love you as well. So I'm going to have to really kind of, you know, squint to kind of imagine this, this scenario.
A
Let's stretch the, let's stretch the imagination. It's a little bit, it's quite plausible and possible.
B
So let's, let's just say that did happen. Generally they'll offer you outplacement. And so pelgo, we.
A
Let's say they don't. Let's say they don't. Because I know that CBS doesn't do outplacement. They're all contract workers.
B
They should, I think that would be my first call to say cbs, why would you not offer these folks outplacement? I understand if it's a few hundred bucks, a few thousand dollars that budgetary constraints are a real thing. But why aren't you, if it's, if we offer a service that's simply a few dollars a month, couldn't we do that? And so if the answer was yes, we would offer you an invite to join Bell Go first via text message or email.
A
Okay.
B
Try to get to know you a little bit. We'd first say, hey Joe, there's a lot of paths in front of you. One, do you simply want us to go away? And you're like, listen, I don't know what pelgo is. You should just go away. I never want to hear from you or CBS ever again. Okay, that's fair. That's one path. Second, you had A guest on not too long ago thinking about retiring early. So is it a joke? You know, what does your 401k look like? Is it. You don't have to tell us, but do you want to think about retiring early? That could be a potential path. Solopreneurship, That's a real path for a lot of Americans out there today. So is it starting your own business? Fourth, do you simply want someone to talk to? And last but not least, do you want to re enter the workforce? Once we know that, then we could say, hey Joe, if you want to reenter the workforce or if you want to do any of the other things that I just mentioned, we can help you with that. So whether it's creating an AI that gets past resume filters to surfacing jobs that numerically, statistically you would be a match for. And last but not least, if there's a gap in that match with, with regards to skills, can we upskill you and can we create modules for you to learn in a very personalized way? So essentially that's what Pelgo does.
A
When you think about how you would upscale or just, you know, kind of help people retrain. Let's say I'm in a job. Here I am, I'll just use myself. Here I am, I'm in a job. News. News is going to get disrupted by AI. You know, we don't need as many writers, editors, we need someone to review the AI. What is it that you think people should be doing who are employed right now to make themselves more AI proficient and also to maybe think about like applications to their own jobs today?
B
That's a really interesting question. And things that I even struggle with, given how fast things are moving.
A
Right.
B
My immediate reaction is probably two things. One, simply by actively participating and actively trying out and trialing all the different tools that are coming out on a weekly basis, you don't have to know, you don't be an expert in all of them. But simply by having hands on experience with all the free tools out there probably puts you in the upper half, if not the upper quartile of all your peer set. That itself is just simply just giving it a try. The longer term answer though, and this is also part of the genesis of Pelgo, is that I think folks are going to be in transition more and more. The days in which you had the same job at the same company for the 50 years of your career or the 40 years of your career, I think those are long gone. I actually think in the coming years we'll think of folks who have been in the same industry for 40 plus years as actually quaint as well because of how fast AI and how fast the world is changing. So with that said, I think the capacity or the simple steps of trying to relearn how to learn because after you've been in a job so long you're just like I don't need to learn anything. I know how to do my job and I do it well is probably the longer term, I guess solution to this is that sparking that curiosity again and that adaptability to change I think will be very, very important. So those two things.
A
You know, when Mark and I first started this podcast, we had no idea how many hats we would be wearing. Host, Producer, Editor, Social Media Manager. It was exciting but also intimidating. We really wish that we had had a built in business partner from day one. A partner like Shopify. It's the commerce platform behind millions of businesses worldwide and powers 10% of all E commerce in the US you can build a beautiful online store with hundreds of ready to use templates that match your brand's style and their AI tools help write product descriptions, create headlines, even enhance your product photos. Plus you can run email and social campaigns and manage inventory, payments and analytics all in one place. Start your business today with the industry's best business partner, Shopify and start. Sign up for your $1 per month trial today at shopify.com jillonmoney go to shopify.com jillonmoney that's shopify.com jillonmoney hey gang. I've recently been thinking about how to make my home feel more functional, not just aesthetically pleasing. I love a good design moment, but you know what? Your space has to work for you. That's why I turned to Wayfair. My big purchases there were very bright desk lights so that I could actually do my work work early in the morning before the sun comes up. And then I got this kind of cool poof that my dogs like sitting on while I do my work. And my next task is some new storage solutions for my closet, some shelving, probably even for my garage. And what makes Wayfair easy is being able to filter everything by size, finish, price and style. Find furniture, decor and essentials that fit your unique style and budget. Head to Wayfair.com right now to shop all things home. That's W A Y-F-A-I-R.com Wayfair Every style, every home. All right, let's do a practical example of Mark Telercio, the Greatest executive producer in the whole world who does every so much by hand. So, Mark, get on the mic and let's talk about how you're going to make your life easy. Mark and I get, we have like thousands of emails in our inbox. Okay. Each of those inbound inquiries can be turned into some content for us, right? Sure. So, for example, like on CBS Radio, I am asked to do a. What is it, Mark? 45 second, like question answer. Is that how it goes?
B
45 second question of the day.
A
Question of the day. How can Mark use AI to automate this entire process, which he is doing, basically doing by hand right now? See, Mark, I'm gonna, I wanted to turn this to our advantage.
B
There may only be 10 more months of doing it, so.
A
All right, good point. But so what? Don't you want to free up your 10 months so you can shovel snow more efficiently?
B
You know, it's, it's funny, I, I, I'm wondering if we're still rolling here. This has just become a practical class online.
A
Absolutely. Why shouldn't we use ourselves?
B
Fair enough. You know, Mark, there's incredible tools out there and actually what you're saying is something that AI can really help with in a quite an easy way. And again, I don't think it's there to replace you. As Jill said, there's a lot of things that you're doing as exec producer that are very difficult to replace with AI but not difficult to augment. So herein lies one of the opportunities. So I'm guessing you're using Gmail or I'm guessing you're using some sort of inbox. The easy thing is to actually hook into that inbox and feed all of that into a daily script that actually not only reads the emails, but also prompts the script to say, here are the thousand emails. Segment for them, segment for me. Things that are along the same themes of early retirement versus starting your own business versus should I pay off my mortgage or not? All things that guests very frequently ask. Once it parses it out, you could say how you want it, so do you want it as a simple percentile breakdown? And then beyond that, you could have it prompt you to say, hey, here's a 60% question. Do you want me to reframe it for you so that it can be read easily on the air? That workflow that I just described is actually probably pretty easy to do. And you could probably do it. You probably figured that out in an afternoon just by using just watching simple YouTube videos or any kind of someone more versed in AI could do that for you in probably 30 minutes.
A
Or maybe you just talked to Shay. Mark. So what do you feel about that, Mark? Because Mark is a little bit of not a Luddite. But, you know, we all cling to our old system, so this is why it's interesting to. Hey, gang. You know, subscriptions are one of those things that feels small in the moment, and then suddenly you're wondering why you are paying for all these things that you barely use. That's where Experian subscription cancellation comes in. Experian can take the pain out of canceling subscriptions by handling it for you. Just keep the ones you want, cancel the ones you don't, and put the money back in your pocket instead of spending your time trying to cancel subscriptions, if you even do that. And you know, there are over 200 subscriptions that are cancelable, which means that there are lots of opportunities to clean things up. And it doesn't stop there. You can also save money by letting Experian negotiate the rates on bills you're already paying. They'll keep an eye out for new deals and savings opportunities and negotiate directly with your provider on your behalf. Get started with the Experian app. Now. Results will vary. Not all bills or subscriptions eligible. Savings not guaranteed. Paid membership with connected payment account required. See experian.com for details. Talk about this, because we are all challenged to break out of whatever we're doing. The iPhone comes out, you and your buddies are like, we can make games on an iPhone. Every new technology has this uncertainty, anxiety, and also opportunity. So, Mark, how do you feel when you hear him talk about that?
B
I am not anti AI. I mean, I use it a lot. I use it all the time. And Amanda, my wife, uses it all the time for her job. She's way more well versed in it than I am. You know, I'm not opposed to using it to help me out, but I'm weird like that. Like, I'm a worker. I like having my sense of purpose. I don't want to have something doing everything for me. I also like to get my hands dirty a little bit. Yeah, I don't think that's a unpopular opinion at all, Mark. In a lot of ways, I'm the same way. I think maybe this is maybe a little bit esoteric, but in some ways, you know, we're talking about, like, an AI revolution, AI evolution. But in some ways, like, couldn't you describe what we're going through as, as a society, almost a potential Renaissance in the sense that, you know, if you look back at the original Renaissance, it was folks actually beginning to uplevel themselves or actually studied the arts, studied the humanities and actually do things that they enjoy and to add to society outside of just creating more pixes and axes. And in some ways, if we could free up time for you, if this technology does that, you know, it could be that you get more time to spend on the creative side of the show or creative pursuits outside of the show. And so, sorry, it's a bit of an esoteric thing, but, you know, I was inspired by Jill just mentioning Luddites. And, you know, when you look back, history often rhymes, and in some ways there's certainly things that rhyme this time around as well.
A
I get that people are uptight. I mean, everybody is using this example of, like, the Internet. And I'm not even sure that having. I'm not sure having the Internet made us more efficient or productive. I know that, you know, there are. But it also, like, has become a massive distraction. Right?
B
For sure.
A
I. This, to me, feels way more like having Lotus 1, 2, 3, which is probably when you were born, you had Lotus.
B
No, no, I use Lotus.
A
Right. It's more like that where it's like, oh, my God, I don't have to use a calculator to do this work. And I remember at the time that this was going to be, quote, unquote, the death knell of the whole accounting profession. And it's far from that. Right. So what I think is also very instructive in this moment of uncertainty and in this moment, moment of transition, is to imagine that you cannot game out every single thing that's going to happen, but you do have the ability to come along in the process. You know, you don't have to be the earliest adopter. You weren't. Right. You didn't adopt AI in 2022. But now with this kind of robust change happening and having you say, as Pelgo being there and saying, we'll hold your hand for this, I think that's where the opportunity lies, which is people are scared to do this themselves, Shay. You know, they really are. It's way better to sort of start getting involved with trying to put your arms around it today while you still have a job, rather than waiting till you don't have a job. Right.
B
I couldn't agree more. I couldn't agree more. And for what it's worth, you know, the first word processor I ever used was basically Lotus Notes. And I remember, you know, I thought that was mind blowing because it could actually spell check for me. And here we are. And so. But what you're saying about kind of the societal impact of folks, you know, having feeling a certain, certain amount of trepidation about AI, that's very normal. And in thought of ways, I have to admit that I feel the same way. I think what right now is causing this concern is, is that a bit of the risk to people's jobs and to their daily vocation is rising. Seems like a lot more rapidly. That risk versus the benefit that people are seeing in their daily lives. And I think that's going to be a real race. And in most other races I feel like it's kind of even out the Internet, over 30 years, social media and all this kind of came about. But I think the imbalance that we have to really be mindful of as a society is that that's happened. You just mentioned 2022. I mean, that feels like a generation ago when it comes to AI, but really that was like 36 months ago.
A
I know, that's crazy. That is actually totally crazy. So what, what if someone's listening? What do you think? And they, they have a kid. Okay, here's the thing. I've got a kid who is applying to 900 jobs. You've seen those silly talks, right? Oh, apply to 900 jobs. That's sort of like how I feel about colleges. Like, calm down. It's a lot easier to apply to jobs today than it ever was. How do they kind of get through the AI filter in a way that's meaningful?
B
I think there's one more tactical, I guess, tip I could provide and one more kind of higher level tip. The tactical tip is that if you're not kind of creating your resume with the help of AI so that it can actually get through the. Unfortunately, probably the many, many AI filters out there that are, that are receiving these resumes and filtering through. I'm not opining on whether this is a good trend or not. I'm just simply stating the facts. Most companies are probably using some sort of AI filter because of the thousands, if not tens of thousands of resumes they're getting. If you're not leveraging to your leveraging it to your own benefit, I think you're doing yourself a very big disservice because there's certain things to say on a resume, certain ways to format it so it actually gets through the filter in a much more efficient way. The second one is, I think I mentioned before, it's like simply highlighting and being Able to show off your capacity to learn and your capacity to adapt, I think will be very, very important. Here's a prime example. In engineering, in kind of my world, there's a lot of engineers out there that are finding it more and more difficult to find jobs. On the flip side, there seems to be almost an insatiable demand for what we call forward deployed engineers. And those are engineers that are on site, they solve problems of the client and actually put together sometimes very hacky solutions to make sure that this esoteric AI or this esoteric piece of software actually works for the client and actually works in that company. Because there's, every company has politics, every companies have, have kind of quirky workflows. And so that adaptation has created this new breed of jobs called for deployed engineers. And so what makes an engineer suddenly a Ford deployed engineer? You don't have to go back to school for it. It's a lot of people skills. It's an adaptability to actually learn how to an organization functions and to be able to then adapt to that organization. The software that was previously built suddenly makes you very in demand today. And so that's a real life example today of some of those skills and some of that adaptability that's going to become more and more important in the future.
A
Okay, so I wrote this blog post and I was talking about AI and I said lean into the jobs that rely on skills that AI so far has not been able to replace. Judgment, empathy and adaptability. Those are the three things. Right? And also of course this sort of open. Someone asked me, one of the anchors this morning said like, and also all those blue collar jobs. So what is the challenge in getting through the AI filter to show that you are more like, you know, I find that some of the AI stuff is so lazy. Like, I know I communicate with somebody who uses AI way too much. I just, I know it's like I work with this person and not in cbs, but it's kind of trash. And you can see it, if I can see it as just, you know, lay person, I think that everyone's going to get onto that. So how can you use it but not rely on it?
B
I think it, you know, maybe it's a little bit of what Mark was mentioning before. In terms of human in the loop. As much as we talked about Palgo, I'm not of the opinion that we're all going to sit around and collect mailbox money via ubi. I think humans in general will still want a certain amount of human in the loop. Loop because as a species, we probably trust other folks of the same species to actually be at the controls. And so that human in a loop process, I think will be very, very important. And even to what you're describing for Joe, making sure you're proofreading it. Sometimes the AI stuff that comes out, it just sounds like AI. There's something nuanced about sounding like a human that I think will be very difficult to kind of fully replicate in the future. That judgment. As you mentioned before, there's a lot of things that are inherently human. I'm not saying we'll forever not be able to solve it or replicate it, but at least in the time being, like, it seems like there's still quite a bit of nuance of being a human that will make highly valuable.
A
What other areas do you think this is like this, I don't know, is this going to put travel agents out of business or is it going to be like, hey, here's your itinerary, here's your 12 days in India. And they curate it with certain other stuff like where do you see potential scary loss of jobs on the horizon besides software engineers, obviously?
B
Yeah, you know, in the white collar world, I think any, or actually even in the blue collar world, anything that's highly repetitive is probably not the right industry to target if you're a recent college grad. Right, I'll put it that way. Now, in terms of will that industry go away? I don't think so. I think we're probably still many years, if not decades away from that simply again, you know, I guess pure technologists will say no, it could probably replicate it. But what I'll say is that I don't think you're gonna negate the need for humans to, to want another set of human eyes on something especially high stakes environment.
A
I was talking to somebody who's writing a book and the book is coming out and I said, I know podcast hosts, I here's what I think you better be ready to answer. You should put your manuscript through an AI filter and you should say, what are the 10, 15, 20 best questions to ask based on this manuscript? Because I have a sneaking suspicion that that is going to form a lot of the basis for interviews. So just in prepping, you should imagine that other people are using your content, running it through a filter and coming up with maybe dopey questions, but whatever, like, you have to know they're going to ask those questions. You know what I mean? That to me is also really helpful just understanding that, you know, if someone writes a brief and they're going to get questioned on it. Like, run it through the filter, see what happens. Don't write the brief only with the filter. But, like, know that that's something that is a tool that's being used, right?
B
Totally. I couldn't agree more with that, but I want to. So, Jill, in your daily life, do you feel like it's like, come in for your job or that it can replicate kind of what you do?
A
So what I think it can do is if I am, it's not great right this second of taking the right sources for someone like me. So what'll happen is if I said, give me a tele. Write it, I can say, write a two and a half minute television script based on the Supreme Court decision overturning Trump's tariffs. And I can, I can ask that question, right?
B
Yep.
A
It'll give me some stuff. But the reference material, you have to be very careful to say, like, well, where did that come from? Where did that come from? You know what I mean? Like, you can know that. So, like, do I think that that's possible? Yes. Do I think that the judgment that I bring to it of, like, that's not the best way to ask that question. Here's a better way. That's not the best way to answer that question. Here's how to break through. But it gives you guidelines, there's no doubt. So I am using it a lot more. And you'll be very proud of me that I am actually creating my own LLM for Jill's voice. I've hired somebody to help me harness that, mostly so I can learn. I just have no. I really wanted to. What I did was I first went into like, oh, I'm 60, I'm not going to need to know how to do this. Then I was like, maybe I should learn. And then my friend's kid is very into it and he worked. This is what he does for a living. And so I am paying him to help me develop this, just mostly so I can learn about it, because it's fascinating and it's not answering all the questions the right way, but it's building something. And that I think is interesting.
B
I love hearing what you just said because the inspiration for us to continue along this journey is partially of what you just said. And so we were working with someone, one of our early kind of testers for the platform when we were first building it, with someone who had lost their job and had been out of work for about two years. And actually hearing from them and saying that it sparked this interest and curiosity in them, that there is kind of a bit of hope and that, hey, if I learn this, this could really help whatever job I get next. It could help me not only in the job search, but in the job. Was really exciting to hear. I generally hope that this time next year and many years from now that there's other folks kind of joining us in this mission. That is Pelgo with their own companies of like, how do we make sure that we're helping folks and not just going after this gold rush that is, that is AI.
A
Thanks to Shay for that great interview. And Mark and I really want to express to you guys that we understand how new can be worrisome. So if you're trying to figure out how you're going to create a plan B for your own career, your own job, get in touch with us. Go to jill on money.com and click click the Contact Us button. It's Friday, so of course I want to tell you that our music is composed by Joel Goodman. Mark Tularsio is our executive producer and king of all things web. We're distributed by the lovely folks at Odyssey. We always ask that you do something nice for someone else today. Change your work, change your wealth, change your life. Thank you for listening and we'll talk to you on Monday.
Episode: Career Transitions With the Help of AI
Date: March 6, 2026
Guest: Shea Huang, Founder of Pelgo and former CEO of Boxed
In this episode, Jill Schlesinger speaks with serial entrepreneur Shea Huang about navigating career transitions in an era of rapid AI-driven change. Together, they discuss anxiety about AI replacing jobs, practical strategies for career resilience, and how Shea’s new company, Pelgo, aims to democratize career support and retraining using AI. The conversation blends candid personal stories, humor, actionable advice, and real talk on both challenges and promise of the AI job market revolution.
Origin Story (04:01)
“As crazy as it sounds now, I started my career as an English teacher... then ended up becoming a corporate attorney... Then, with some friends, started a studio making games for the iPhone, which led to being in e-commerce at Boxed for almost 10 years.”
— Shea (04:21)
SPAC Experience (06:18)
Genesis of Pelgo (07:39)
“It seemed like an afterthought... just folks proselytizing that, ‘Oh yeah, and AI is going to displace hundreds of millions of people from their white collar jobs’... okay, where’s the next part about what we’re doing for those folks?”
— Shea (08:20)
“We couldn’t find too many companies there. And so we thought we had to tackle it.”
— Shea (09:12)
Predicting the Future of Work (10:11)
“AI is going to destroy jobs, but over time... there’s going to be a lot of jobs created that we don’t even know today...”
— Shea (10:46)
Product Offering (11:31)
“With LLMs... there’s no reason why that shouldn’t cost a few bucks a month. And everyone transitioning in their career should have access to that.”
— Shea (12:21)
User Journey Example (13:06, 14:03)
“If you want to reenter the workforce... we can help you. Whether it’s creating an AI that gets past resume filters to surfacing jobs... and if there’s a gap in that match, can we upskill you...?”
— Shea (14:44)
Practical Preparation (15:12)
“The simple steps of trying to relearn how to learn... after you’ve been in a job so long, you’re just like, ‘I know how to do my job and I do it well’... Sparking that curiosity again and that adaptability to change will be very, very important.”
— Shea (16:25)
Jill explains the manual work involved in sifting email inquiries and creating radio content; asks how to streamline with AI.
Shea walks through how AI can automate categorization, draft scripts, and prompt content ideas—freeing up time for creative work, not replacing human contribution.
“There’s incredible tools... hook into that inbox, feed into a daily script that not only reads the emails but also prompts the script… you could have it prompt you to say, ‘Here’s a question, do you want me to reframe it for on-air?’... That workflow... is actually pretty easy to do.”
— Shea (20:16)
Why Resistance and Anxiety Happen (24:35, 25:00)
“It’s better to start getting involved with trying to put your arms around it today while you still have a job, rather than waiting till you don’t.”
— Jill (25:56)
Job Seekers’ Tactics (28:01)
“If you’re not leveraging [AI] to your own benefit, you’re doing yourself a very big disservice... I think highlighting your capacity to learn and adapt will be very important.”
— Shea (28:19)
Jill’s Blog Wisdom (30:12)
“Lean into the jobs that rely on skills that AI so far has not been able to replace: judgment, empathy, adaptability.”
— Jill (30:13)
Human-in-the-Loop Importance (31:04)
For job seekers/parents:
For creators (authors, presenters):
AI is moving quickly, but with the right support and mindset, individuals can find hope, curiosity, and opportunity in transition.
“Hearing from [users], that it sparked this interest and curiosity in them... was really exciting to hear. I generally hope that this time next year... there’s other folks joining us in this mission... how do we make sure we’re helping folks and not just going after the gold rush.”
— Shea (35:47)
On unpredictability of the job market
"If you said, fast forward many years, there’s going to be these things called podcasts…99% of people would say, I don’t believe you. But here we are.”
— Shea (10:26)
On AI resume filters
“If you’re not kind of creating your resume with the help of AI so that it can actually get through… that are receiving these resumes and filtering through, I think you're doing yourself a very big disservice.”
— Shea (28:14)
On what AI can’t replace (yet)
“There’s something nuanced about sounding like a human that I think will be very difficult to kind of fully replicate in the future.”
— Shea (31:33)
On human adaptation in the AI era
“Sparking that curiosity again and that adaptability to change I think will be very, very important.”
— Shea (16:25)
For anyone worried about AI upending their career, this episode offers grounded advice and hope. Embrace change by experimenting with AI tools, focus on what makes you uniquely human, and prepare for more frequent transitions. Platforms like Pelgo are being built to hold your hand through uncertainty—and the show’s own story is a perfect case study in adapting, learning, and not being left behind by technological waves.