Smart Money Podcast: Employee Stock Purchase Plans and AI Travel Planning

Welcome to NerdWallet’s Smart Money podcast, where we answer your real-world money questions. In this episode: Explore how AI can help with personalized travel planning, then learn about Employee Stock Purchase Plans.

This Week in Your Money: Travel Nerd Sam Kemmis discusses the surprising benefits of using artificial intelligence for personalized travel planning. He joins hosts Sean Pyles and Liz Weston to share his experiences with AI tools such as ChatGPT and Google's Bard, including tips for guiding AI and validating creative suggestions before committing to a travel itinerary. The Nerds also explore the pros and cons of “mystery travel,” where travelers embark on journeys without a concrete itinerary in order to embrace spontaneity and adventure.

Today’s Money Question: Investing Nerd Andy Rosen joins Sean and Liz to help answer a listener’s question about whether he should participate in his company’s employee stock purchase plan, also known as an ESPP. Andy explains what an ESPP is, why it benefits companies to offer one and tactics for employees to assess whether they should participate. The Nerds also talk about the risks involved, how to plan for related taxes and potential limitations on when employees can trade their stock.

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NerdWallet stories related to this episode:

How to Plan a Trip

ESPP: What to Know About Employee Stock Purchase Plans

You Got a Better Job. Now, How Do You Handle the Benefits?

Have a money question? Text or call us at 901-730-6373. Or you can email us at [email protected]. To hear previous episodes, go to the podcast homepage.

Episode transcript

Sean Pyles: Buying your company's stock at a discount can be a nice way to turn a quick profit, but can it also leave you overexposed to a single company's stock?

Liz Weston: In this episode, we'll talk about whether you can have too much of a good thing.

Sean Pyles: Welcome to NerdWallet's Smart Money Podcast, where you send us your money questions, and we answer them with the help of our genius Nerds. I'm Sean Pyles.

Liz Weston: And I'm Liz Weston.

Sean Pyles: Listener, tell us, what do you want help with financially? Maybe you're sorting through your student loan repayment options or wondering how to earn your new travel credit card's signup bonus. Whatever your question, send it our way.

Liz Weston: Try recording a voice memo on your phone and emailing it to [email protected] or leave us a straight-up voicemail on the Nerd Hotline at 901-730-6373. That's 901-730-NERD. We accept emails and texts too, of course, but we really want to hear your voices.

Sean Pyles: In this episode, I answer a listener's question about whether employee stock purchase plans are a good option for retirement investing. But first, we are yet again calling on our digital overlords, by which I mean artificial intelligence technology, to help us answer a few questions. And this time around, we're talking about how to use AI to plan travel.

Liz Weston: And joining us for this journey is NerdWallet travel writer Sam Kemmis. Welcome back to Smart Money, Sam.

Sam Kemmis: Hey, great to be here.

Sean Pyles: So, Sam, people are using AI for all sorts of things these days. How do you use it for travel?

Sam Kemmis: Yeah. I was playing around with this for an article I was writing and found that it was so useful that I've actually been using it quite a bit. So I use Google's Bard and ChatGPT, and what I've found is, it's really good for providing recommendations that I might not get just by Googling something or by looking in a guidebook or even by asking friends. I can get really, really specific with these chatbots and get really, really specific recommendations.

Sean Pyles: Oh, interesting. So, Sam, what's an example of that?

Sam Kemmis: Yeah, so this was kind of as a joke. I wanted to push ChatGPT to its limits, so I gave it very specific interests that I had for a trip to Japan. And I told it, I'm really into trains, I like being out in nature, I like weird stuff, off the beaten track recommendations, I'm into meditation. I just threw everything about me at it and said, "Come up with a plan for me." And I was really shocked that it didn't just give me a cookie cutter idea.

It gave me a bunch of interesting ideas for visiting Buddhist temples that are off the beaten track, like I had asked, some historic train lines that have these interesting old cars in them, even some really fun cars, like Hello Kitty trains and that sort of thing that you only find in Japan. And then it hit me with this recommendation for a pilgrimage. It's actually a hiking pilgrimage that visits various shrines along this island in southern Japan, which was the perfect recommendation for me. And I haven't done it, but I was blown away with how personalized it could get.

Liz Weston: And did you have a back and forth with it? Were you asking it questions or giving it feedback?

Sam Kemmis: Yeah. That is the game of these things, right? Unlike Google, where you just plug in your question and then hope for the best, it’s a bit of this back and forth like you're talking to a real person. And what I'd find myself doing quite a bit is saying, "OK, that feels a little boring. Do you have anything more interesting or anything more specific to my interests?"

That was a phrase I used quite a bit, reminding it, "Hey, don't just give me travel tips to Japan, but really tailor it to me." And the fun thing is that, once you start doing that, it catches on to what you want. So the more you do it, the less you have to do it for future recommendations in that same chat.

Sean Pyles: That makes sense, because with these AI chatbots, the game is really playing how to get the best prompt to get them to give you the answer that you might want. So being as specific as you can to your interests and what they might be able to get back to you is maybe the best way to go about it.

Sam Kemmis: Yeah, exactly.

Liz Weston: I was using it for a couple of different purposes, one was to try to plan out a trip that we're taking to Austria, and I had the same experience that you did, Sam. The more information and the more dialogue I had with it, the better it did.

But then I tried to get it to actually plan a trip. I wanted to go to five different cities, and I wanted it to plot out the most efficient route via high-speed train from city to city, and it just started making things up. It decided that there was a train from Vienna to Copenhagen, and I said, "No, there's not a train the way you said." "Well, no," and it kept doubling down. It was like, "OK. Well, there's not that train, but you can take this train." And I kept trying to correct it, and it just insisted that I could do this trip, which I really can't do.

Sam Kemmis: Yeah.

Sean Pyles: That makes me wonder whether these services are better at surfacing recommendations rather than planning out the logistics of a trip, because those are really the two important components of any sort of trip. You have to know what you're doing and then how and when you're doing it. And when I was hearing you describe that journey or potential journey in Japan, Sam, my thought was, "Are they building in nap time?" Because that's something I always want to build into my vacations, and I didn't hear that.

Sam Kemmis: Yeah, that's true. Yeah, it didn't give any nap recommendations.

But it's a really good point on the two parts of travel and what these AI chatbots are good for. They're really creative. They're really good at coming up with things that you might not think about, but they can be a little too creative, like you ran into, Liz. And they can get a little overconfident and just make things up and really act like they know what they're talking about when they don't.

So I would, before I say, "Oh, I'm going on this amazing pilgrimage based on what ChatGPT told me,” I want to do some independent research on it to make sure it's a real thing, that it's still available. There's all sorts of potential pitfalls. So use it as an idea partner, but definitely not a travel agent.

Sean Pyles: Yeah. Well, part of the limitation is that, for ChatGPT at least, they only have data through 2021.

Sam Kemmis: Yes, exactly. A lot of it's not up-to-date, and it can seem, because they're so smart, it can feel like they know everything, but it's important to remember that they're working on historical data, so they have no idea what's going on right now. Maybe even in the example of that train, it could be that there was a train line open in 2021, and it no longer is, but they are completely unaware of what's happening currently. So, yeah, it's something very important to remember, especially with countries opening and closing borders, and even roads being open or not, and weather conditions. These are all the types of things that ChatGPT has no idea about.

Liz Weston: Sam, I like to ask my fellow Nerds, including you, for travel tips or even read an old-school guidebook. So how would you rank AI against those resources?

Sam Kemmis: Yeah, I think it's a complement. I think, like I said, it's definitely not a travel agent, but it's more like a guidebook, but what it can do is get really specific. So you might be going to Mexico City and you would look in a guidebook and see what the best restaurants are, but they're just going to be the best restaurants for everyone. And what if you want to say, "Well, yeah, but I'm gluten-free and I don't eat meat"? So AI can start taking that information and saying, "OK, given that you don't eat meat and that you're gluten-free, maybe you want to check out this taco stand, or maybe you want to take a trip to this region, has really good cornmeal," these really specific niche recommendations that you would just never get from a guidebook and maybe not even a friend.

Or let's say you have a family, you could look up family travel tips, but I find that that's really useless 'cause there's a big difference between having a 12-year-old and having a 2-year-old. Those are very different types of families. So you can say, "Hey, I have a 2-year-old and I'm going to Columbia. What the heck can I do?" And ChatGPT can start getting a little more creative there in a way that a guidebook or even a friend who doesn't have a 2-year-old and has never been to Columbia can't really help you out there.

Sean Pyles: Well, when you've used ChatGPT or these other AI services, Sam, have you found that they're missing that nebulous human touch that you want when you're getting recommendations for travel?

Sam Kemmis: Yeah. You'll run into these jarring moments where you're reminded that you're talking to a machine, for sure. And some of that is you'll dump your life story in there, and then it will give you personalized recommendations, but they don't know everything about you. It's hard to put everything that you care about into a prompt. So a friend or even a co-worker is, in some ways, going to know more about your personality than ChatGPT ever will. So, yeah, it's hard to get that really, "Oh, you would love this specifically." ChatGPT's never really going to know that.

Sean Pyles: Right. What I'm thinking of now is, say you have a friend who loves art, but they don't really have the temperament or patience for a really busy museum. Maybe ChatGPT would say, "Oh, go to this museum," but if it's super crowded all the time, you as a friend of this person would know, "Hey, you're probably not actually going to like it. Maybe go super early in the morning or when they're going to close, some time where it's not peak hours."

Sam Kemmis: Yep, totally. ChatGPT kept recommending Disney Japan to me, which anyone who knows me would never do such a thing, so yeah.

Liz Weston: OK, Sam, I'm going to step in here, but DisneySea is the most amazing theme park I've ever been to in my life.

Sam Kemmis: I believe you.

Liz Weston: Maybe you don't want to go with a 2-year-old, definitely, but next time you're in Japan, just drop in, check it out. You really will be amazed.

Sam Kemmis: OK. All right. You see, I'm wrong. You're my friend and you're recommending it to me.

Liz Weston: I am. So, Sam, I've heard that travel companies are also integrating AI into their booking platforms. So what does that look like?

Sam Kemmis: Yeah, there's a few examples of this. One that I've toyed around with a bit is Expedia has added some AI into its app that will let you get recommendations and then save those recommendations in the app. Some other companies, like Booking.com and Airbnb, are saying that they're adding AI trip planning and customer service at some point. Those are rolling out slowly.

Honestly, I would say, at this point, this has all happened so quickly that a lot of these services are very much in the beta mode. I haven't seen anything where I'm like, "Oh, wow, it's so much easier to book my trip using this AI tool." It's more like, "Oh, that's a neat little add-on feature that they put in there." So, yeah, some interesting things out there, but we're very, very far from the point where you're going to get on a chatbot and book your entire trip.

Sean Pyles: Yeah.

Liz Weston: Well, if AI could help, then that would be great, because right now chatbots really, really suck.

Sam Kemmis: Yeah. Oh, certainly. Those customer service chatbots are no fun, so any improvement there would be welcome.

Sean Pyles: OK Now let's talk about what may be the opposite of AI assisted travel planning. We're going to get off the AI track completely now, and Sam, we're going to talk about something you refer to as mystery travel.

With this approach to travel, you have a much looser itinerary. Maybe you know when you're flying into a location and flying home, but what you'll be doing there, where you'll stay, is potentially a mystery. So compared to the hyper planned out AI assisted travel, what do you see as the main draw of this more on-the-fly way of traveling?

Sam Kemmis: Yeah. I spoke with several travelers who had done mystery travel or surprise travel, as some people call it. And a lot of what I heard was that the big appeal was not needing to plan, that there's this paradox here where we spend so much time planning our trips and coming up with every little detail and knowing exactly what we are going to do, and there's something really freeing about just saying, "I have no idea what I'm doing on this trip that I'm leaving for tomorrow. I don't even know where I'm going tomorrow." And it relaxes that part of our brain that just wants to know. And a lot of people said that was extremely appealing.

Sean Pyles: I thought you were going to say terrifying, because that would be terrifying to me.

Sam Kemmis: Yeah. Maybe pushing people out of their comfort zones a little bit. But I do think that there's this bit of adventure that travel is really supposed to be about, that we're supposed to be doing something we've never done and getting a little out of our comfort zone and getting a little lost. And the more that our travel has become Google Maps-ified, we've lost some of that adventure in it. So I think this mystery travel trend is really trying to reclaim some of that. It's just saying, "I'm striking out and who knows where I'll end up?"

Liz Weston: Well, I love travel and adventure, but I also have huge FOMO when it comes to travel. I hate coming home from a trip and discovering there was something really cool that I missed. It was a block away and I didn't see it. And also if you're traveling during busy times, it can be hard to even get into places without reservations. So I get the appeal, but I'm like, "Ah, that's probably not for me."

Sam Kemmis: Yeah, it's definitely not for everyone.

Sean Pyles: Yeah. I mean, I totally feel that. I try to take an approach of radical FOMO acceptance when I travel, because I realized that you can never see everything that a city or a country has to offer. So I like to choose a handful of museums, restaurants that I know I'm going to go to, but then also leave space for impromptu adventures. And like I said at the beginning, I'm always going to be building in nap time to my day, because I need that.

Sam Kemmis: Yeah. What I've learned is that naps are the most important part of traveling for you, Sean.

One piece, one approach that some people have to this mystery travel idea is that they actually do it in friend groups. So they'll just rotate every year who is planning the trip, and then whoever plans it keeps it a mystery to everyone else. So if you have a friend who you trust to build in nap times or to get the reservation at the restaurant that you really want to go to, then you can entrust them with that and lose all the burden of having to do the planning yourself. And then also, if it doesn't work out and you do have FOMO, then you have someone to blame other than yourself.

Sean Pyles: Yes, exactly.

Liz Weston: I love that. Perfect.

Sean Pyles: I will say, my friends who I travel with, we always build in nap time, even if it's what we call phone nap time, where we just sit in silence and catch up on social media. It helps us feel rested. So, anyway, well, Sam, thank you so much for talking with us.

Sam Kemmis: Thank you. It's always great.

Sean Pyles: Before we move on, listener, I have a couple of updates for you. First, I want to thank all of you who took our listener survey over the past few weeks. We are reviewing your really thoughtful feedback now, and I have no doubt that it will help us make the show more useful for all of you. And also, congratulations to Jessica in Colorado and Abemale in Pennsylvania, who won our listener survey sweepstakes. I hope you guys enjoy those Amazon gift cards.

And, finally, I have an exciting announcement. I've made the jump from behind the mic to in front of the camera on new social media channels. You can find me on TikTok and Instagram under the handle seanpyles_nerdwallet.

Liz Weston: Woo-hoo. So, Sean, what's the deal with the channels? So are you finally going to become a personal finance influencer?

Sean Pyles: Maybe, if I'm lucky. Well, Liz, as you know, my favorite part of the job is connecting with listeners, whether I'm listening to voicemails, answering money questions with you, or talking with them live on the podcast. And these new channels are platforms for us to carry on that conversation, get deeper into our relationships with money, and of course, I'll have all of the Nerdy money tips that our listeners have come to expect. And in the end, my goal is to create spaces that genuinely help us all live our best financial lives.

Liz Weston: Ah, that sounds aspirational. And, listeners, you know we've had a few negative things to say about personal finance influencers in the past, but Sean, you can listen to, definitely.

Sean Pyles: Thank you. Thank you. And I do want this to be a genuine space where I bring well-researched information to listeners. There are plenty of people out there who do just say whatever the heck they want and maybe aren't backed up by reporting, the way that we at NerdWallet are. So I would say, listener, follow me on TikTok and Instagram. Again, my handle on both platforms is seanpyles_nerdwallet. I'm going to spell that out for you, S-E-A-N-P-Y-L-E-S, underscore, NerdWallet. And I'll give you guys a minute to pause, follow those accounts.

OK, thank you. That's it for this episode’s This Week in Your Money segment. The money question is up next. Stay with us.

This episode's money question comes from James, who sent us an email. Here it is, as read by NerdWallet writer Spencer Tierney.

Spencer Tierney: Hi, Nerds. I hope you're doing well. I'd love to get some of your thoughts on whether investing with an ESPP is a good option and whether to prioritize that over a Roth IRA or similar investment. So, some background. My name is James. I'm a 30-year-old male, married, and I have a 1½ -year-old. My wife and I make combined $180K a year pretax. I am maxing out the federal amount in my 401(k) due to a generous company match. My wife is not using her 401(k) as of this year, but we are starting to use a Roth IRA for her. There are no debts other than the house, paying less than $2K a month for the mortgage. Thanks, James F.

Sean Pyles: To help us answer James' question on this episode of the podcast, we are joined by Investing Nerd Andy Rosen. Welcome back to Smart Money, Andy.

Andy Rosen: Hi, Sean. Let's just say I am ESP-pecially glad to be back with you today. Sorry.

Sean Pyles: Corny, Andy. Corny.

Andy Rosen: No, I'm not sorry. I'm actually not.

Sean Pyles: Well, happy to have you as always. Well, before we get into our listener's question, a quick disclaimer, we are not financial or investment advisors. All of this information that we are about to discuss is just for general educational and entertainment purposes.

OK, with that out of the way, Andy, investing often requires us to wade into a murky alphabet soup, and ESPPs are no exception. Can you please explain what ESPP stands for and generally what it is?

Andy Rosen: ESPP, it doesn't have anything to do with paranormal activity. It does stand for employee stock purchase plan. So when you participate in an ESPP, what you're doing is you're getting the opportunity to purchase shares of your company that you work for at a discounted price.

Sean Pyles: OK. So it's like a perk for employees of public companies, right?

Andy Rosen: Absolutely, and companies do have a few reasons that they offer them.

Sean Pyles: Please, will you list them?

Andy Rosen: Yeah. So for starters, it's a benefit, right? And why do companies offer benefits? Some are required by law. This one isn't. A company offers a benefit to distinguish itself from another in the eyes of a worker who might have many options when taking a job. For the company, this is also a perk that you can offer without paying for it in cash. So with the discount, an employer may be foregoing a higher price they could get on the open market, but the out-of-pocket expense is lower than if you were just giving a dollar to an employee, right?

Another reason is employees who own stock in a company may feel more aligned with management and potentially they would be willing to work harder or make other sacrifices that could potentially raise the value of their shares.

Sean Pyles: Mm-hmm, 'cause that gives them a different sense of ownership of the company, because they quite literally have the stock. They own that.

Andy Rosen: Right, exactly. If the company does well, your stock would go up, potentially. So you'd feel pretty good about helping the company succeed and maybe less at odds with management or things like that. Of course, it might not solve all those problems, but it can help.

And finally, if a company has a large ESPP, the paycheck deductions that employees use to fund these shares can be a way to raise capital pretty efficiently and automatically, just money coming in.

Sean Pyles: So you've just listed a few reasons why companies offer ESPPs. What's the main draw for employees?

Andy Rosen: Well, it's really the discount, right? Let's say you can buy a stock for 20% less than it's worth in the open market. That gives you a lot of choices, right? You could sell it immediately and lock in a financial gain that would be hard to replicate elsewhere.

If you hold it, you're starting with a cost basis, the cost that you actually paid for it, that's lower than you'd get on the market. So if it goes up, your profit could be higher. If it goes down, your loss could be lower.

And, finally, there's one thing that I think it's really important to note for employees that are going to do this. You're not going to keep all the profit, should you have any. There are taxes associated with ESPPs, including capital gains taxes. So the IRS is always going to be around somewhere when you're talking about buying and selling stock, right?

Sean Pyles: Yeah, so it might be a good idea for someone who is enrolled in an ESPP program to also hire a tax pro to help them sort out what this might mean for them.

Andy Rosen: Right. I mean, presumably your provider that's running the program for your company will give you the forms you need, but you do want to consider what exactly this is going to do to your bottom line.

Sean Pyles: Mm-hmm, OK. Historically, I've been maybe a little too wary of ESPPs, because I've heard that some financial advisors will recommend that their clients don't hold too much stock in the company they work for because the employee is already fairly heavily, quote, unquote, invested in that company because they're spending 40-ish hours a week working for them. So, do ESPPs risk making that problem worse for employees?

Andy Rosen: It's worth thinking about. I mean, if your company suffers some kind of financial calamity, you're already exposed even before you buy any stock. So say you own a bunch of stock in your company and you lose your job. So that's a big piece of your income, and you've got big stock losses on top of that, and you're going to be in a pretty bad mood that day.

And there are other risks, too, that are specific to being employed at a company. So depending on how your ESPP is structured and the specific trading rules that apply to you, you may receive your stock during what's called a blackout period, in which you can't trade it. So that can happen around earnings reports or at the end of a quarter, for instance. And if something happens that would make you want to sell any other stock in any company you don't work for, you might be uniquely limited in what you can do during these very sensitive times.

Sean Pyles: Right. Andy, it occurs to me that one potential opportunity to mitigate overexposure in a company through being enrolled in ESPP program is by taking the money that you would get from selling that stock and then pretty quickly reinvesting that into something like a mutual fund or a robo-advisor account, something else where you can take this money that you already had essentially allocated toward investments and putting it into something else that's not the company that you work for.

Andy Rosen: Right. It's worth thinking about the fact that concentration is risky because, if your stock goes down, a lot of your portfolio goes down. It also has the potential for rewards, right? If a company does really well and you're invested heavily in that company, you'll net more of those gains than you would if you were invested just a little bit in that company and then in a bunch of other companies that didn't do as well.

So, again, it's not necessarily always the most prudent thing to put all your eggs in one basket. That's why they have that idiom. But on the other hand, it depends how you've set up your portfolio and, if you have room, to take a chance on the company you work for. That's what you'd be doing.

Sean Pyles: Right. OK. Well, now let's get to the meat of James' question. On the spectrum of investing priorities, which is of course very individual and subjective, where might ESPPs fall compared with retirement investing accounts like a Roth IRA or even a 401(k)?

Andy Rosen: Well, let's just define this for people. So, if you're using a typical 401(k) or a fund within a retirement account, there's lots of options that you have that are basically funds that are set up specifically to provide you with the income you'll need once you stop working, presuming you fund it correctly. So remember that your company may also be giving you free money in other ways for you to invest. So when your company gives you a match for your 401(k) contributions, you're getting basically free money that's going into investments that are going to hopefully help you down the road.

So if you're trying to think about whether to put money into one or the other, you have to think about how you're set up with retirement, how healthy your savings are. Do you have money that might be better spent shutting off some short-term debt that you have? Because those are going to help you determine whether you can really afford another investing product.

I guess the way I'd think about it, is it doesn't replace any of these things. You need to still have a healthy portfolio and follow the normal principles you'd follow and then decide, can I add something?

Sean Pyles: Yeah. I imagine that a lot of financial advisors would maybe recommend investing more into the 401(k) to at least get the match from your employer, if there is one, and then potentially a Roth IRA, because accounts like this are tax-advantaged and designed to encourage you to invest in them for your retirement. Where ESPPs, like you laid out before, have some potentially complicated tax consequences.

Andy Rosen: Right. I mean, it sounds like the listener is already contributing to their retirement account and is weighing whether to get into an ESPP. If you're not sure if you want to work with an ESPP, you're not sure how it's going to feel to have that kind of concentrated investment, you don't have to invest a lot. If you're interested and not convinced, you can start with a small amount and see how it affects your cash flow. I mean, you've got paycheck deductions, and suddenly whatever, that cable bill became a problem, you can decide, "Does this work for me?" And if you do think that it does, then you can increase it.

But it really depends on your company, your portfolio, and the specifics of your ESPP, because there's a number of ways that these could be set up. And I just think that whatever the listener is thinking about is really going to have to be considered in his own individual circumstances.

Sean Pyles: OK. That makes sense. Andy, thanks so much for sharing your insights. Do you have any final thoughts for our listener or anyone else considering an ESPP?

Andy Rosen: I've always got thoughts, Sean. So I guess what I would say is this is just another calculation of risk and reward, right? The risk being, is your company going to do well? Are you going to have to hold stock you don't want to hold because you bought it just for the discount? The potential rewards are, your company's stock goes up, or you get to cash out that discount, depending on whether you want to hold it or not.

So it's just another way of slicing and dicing risk and reward in your portfolio. Just really think about what your specific needs are going to be.

Sean Pyles: All right, well said. Thank you, again, for talking with me.

Andy Rosen: All right. Thanks, Sean.

Sean Pyles: That is all we have for this episode. Do you have a money question of your own? Turn to the Nerds and call or text us your questions at 901-730-6373. That's 901-730-NERD. You can also email us at [email protected]. Visit nerdwallet.com/podcast for more info on this episode. And remember to follow, rate and review us wherever you're getting this podcast.

This episode was produced by Liz Weston and myself, with help from Tess Vigeland and Meghan Coyle. Chris Davis helped with fact-checking. Kevin Tidmarsh mixed our audio. And a big thank you to the folks on the NerdWallet copy desk for all their help.