The Best One Yet - “Hotline #1”: Investing, job-jumping, salaries, & work-life-imbalance — from your Business Besties Nick & Jack

Episode Date: March 15, 2024

A new monthly-ish Q&A series from The Best One Yet podcast where Nick & Jack answer your voicemails. So sit down (literally) with the voice of pop-business — The ex-Wall Streeters (now besties) answer your questions on investing, on entrepreneurship, work, podcasting, life, and even restaurant recs. Guac is always extra, but this business advice isn’t. Description: Traits to look for in a business partner or co-founderHow Jack funded his open bar with an investmentWhy you *should* job jumpHow to become a student of the stock Nick’s tip on negotiating a salary Choosing what stock to sellCall-in for Nick & Jack to answer your questions - Investing, work, how to launch a company… or what’s the secret ingredient in a cookie crisp?Have a question you want us to cover on a show? Email us a voicemail at [e-mail] — your business Besties gotcha back. Hosted on Acast. See acast.com/privacy for more information.

Guys, one time Nick and I, we had two roommates and it was like a Sunday and someone had the idea that we should take like a steam together. Yes. And so we went to the New York Health and Rackett Club. Oh, 13th Street. It was great. And we went into the steam room thinking it would be a nice detox. But it was so hot in that. It was too hot.

The steam was overwhelming. At a certain point, we couldn't see anything. Visibility was extremely low. And so we all sat there like pretending we're having a good time. At one point, Jack was panting so much. I was looking for a deferbils. But none of us acknowledged the pain. No, no, no.

Discomfort. Like, we're all silently looking for the defibrillator. And then at one point, someone just goes, guys, what a relaxing Sunday afternoon. This is great. Nothing like a good steam on the Sunday. And so it's just goes, it's too hot here, isn't it?

Dave was first to acknowledge the discovery. And the best part was, he apologized. He said, I'm sorry, guys, I got to go. No, we're like, thank God. Thank God. We all got out of it. That's why they called the day of rest. Once Dave left, we all immediately left.

Our buddy Timmy barely survived. I think Timmy called the fire department. That's true. Hey, you've reached Nick and Jack at the T-Boy Hotline. We couldn't get to the phone right now, but you know what to do? Leave a message after the beach. Leave a message. Ask us any question, and we will answer your question live on the T-Boy Hotline podcast.

We'll get back to you. You know what to do. First, a quick word from our sponsor. This is Nick. This is Jack. And today's pod is the best one yet. This is T-Boy Hotline episode one. The T-Boy Hotline.

What are we got, Jack? This is a brand-new podcast series from T-Boy where you are in charge. You submit your questions and Nick and I answer them live on this show. We're going to be talking about your job life, your work-live, your relationships. We're talking about finances, you're investing.

Jack, are you going to share your mango recipe to smoothie? It's a pineapple. Nice try. You failed to test. Trick question. I knew you'd answer it. The ladies, we got a fantastic show for you because you are going to be the show.

We're hoping to put these on. every month, but it depends on you sending us your questions. So if you have a question that comes up during the show, email us at Nickinjackat, T-Boypod.com. And to sprinkle on some context, yeah, Rachel from the T-Boy team, has been listening to all of your voicemails, all of your messages, sorting through them all, whipping them up into a perfect mix. Rachel, our creative director, is handling all the questions today. She's going to be the operator of today's show. She's looking fantastic. We can't even see her. She's not here with

us physically, but she's here spiritually. We can feel the presence. I've been told that people can feel my presence. Rachel, I can't see you, but I'm sure you look fantastic. How you doing? Hey, guys. Hey, Yetis. Happy to be here. We're pumped to have you too, Rachel.

Thanks for going through all the voicemails, all the DMs. What do we got? We got a good mix. The Getty's are killing it in the DMs. There's been a lot of hard questions, a lot of juicy questions. I'm really, really pumped for this episode. A little too pumped for this episode. Rachel, can you hit us up with our first question, please?

What do we got, Rachel? Who is it? Where are they from? Nick and Jack here. We're ready for you. Your first question is from Khalid Al-Kulab in San Diego. I'm in the process of building my startup. And one of my challenges I'm facing is finding the right co-founder. Unfortunately, my best friend isn't an option for this role,

leaving me somewhat at a crossroads. As I am on this search, what should I look for in a business partner? I'm sorry, Collad, that your best friend's not available. Yeah. That is the only co-founder experience I have is with my best friend. Co-foundership is a beautiful thing. So the co-founder I picked, I think, Caled, this story may be instructive, just hearing like, what it is about Nick that makes him a good co-founder?

Looking for a co-founder, what do you look for? What do you look for? I wasn't looking for a Wharton MBA, although I got one. We weren't looking. I was looking for someone who was complimentary, whom I could trust, and who I enjoyed spending time with. Because your co-founder, you're going to spend so much freaking time with. On the complimentary front, Nick was born and raised.

in New York City, like literally in the city. I was born and raised in Vermont. Complimentary. Yeah, not the same. Nick was an Italian, like, foreign exchange student. I was a German foreign exchange student. Complimentary. I was a NICON major, you were a history major.

Complimentary. I went to baseball camp. You went to piano camp. Complimentary. Where's middle C? I worked at a bank after college. Nick did for a second, but then worked at a nonprofit venture capital. Complimentary.

Honestly, we have so many diverse experiences. is me having grown up in Vermont with three brothers. You haven't grown up in New York with a sister. Yeah, it's comfortable. We have different life experiences and it enhances the show, which is wonderful. Like just the right amount of overlap. Like when I first met Jack, first moment, freshman year of college, we walk into the same dorm room, same Seinfeld DVDs.

Well, this speaks to the trust point. We want someone you can trust. That's number two. You want complimentary and then number two is trust. We trust each other because we go back and have shared some really embarrassing experiences with each other. on the co-foundership level, on the trust level, there's also why I love you and well- Oh boy. We've already dropped the love bomb so early in the episode. So there's this concept of here you are versus here I am. There you are versus here I am.

Like a psychology concept. People who are here I am tell you all about themselves. And you walk away from that conversation knowing all about them, right? But there you are people. make you feel like you are the center of the world and you're the happiest person ever. And I have not met anyone in my life who is more of a there you are person than Jack Kramer. Wow. Because Jack will be in a conversation and he'll remember, oh yeah, this person has a daughter who studied abroad in London and loves baguettes. And he will engage that person in that conversation and they will feel so happy about it. Jack will remember these details about your life like you just shared about me that you've forgotten about.

And the next thing you know, you feel so happy. And it's because Jack puts you on a pedestal. And it's this incredible superhero value that Jack is. Well, I'll also embellish details about your life. That's true. Like the piano camp. But that's very on branch. Jack will round up for you and you're not going to stop.

So the third quality, Calad, that I think you need in a great co-founder is enjoying spending time with. Because Nick and I started as a side hustle. like in terms of our business relationship back in 2012 it's 12 years later now we've spent so much time working with each other and since nick was born and raised in new york city he grew up in the mecca of comedy and the number of laughs i've gotten from nick it's just insane i'm going to get a dozen more guaranteed on this episode well jack and i have worked every single day together on something and we have laughed every single day on whatever we were working with so i think in an ideal co-founder, you're going to look for those three things. You might not get all three.

You can't check all three boxes. You want someone who's complimentary in terms of your skills and experiences. Someone who you can trust. Totally. Which you may not have at the beginning. Trust may take time to develop. You gave me my first pair of jeans. I trusted you on that. And third is you need someone who you enjoy spending time with because you're going to spend a ton of time if you're getting into entrepreneurship to build your company. I love that, Trio. Can I add in some quantitative stuff to that? Sure. Okay. Sam Altman. everywhere these days. Yes.

Founder of OpenAI, he started out at Y Combinator where he was investing in a whole bunch of companies. And they did a study on their companies in the Y Combinator Accelerator for startups. And they discovered what the best most successful type of founders were. And you know who they were? Co-founders. Specifically, the most successful startups

were co-founders who met in college. Wow. Because in college, you get those three things. things that you're talking about. You get matched with someone who's your roommate who's complimentary. The school system put us together. Sure, true, true, true. Then you end up building trust because you're in college and you need to take risks together. Yeah, the whole inventory of beer pong stories. Do you laugh more than with the friends who you made in college? No. I know. So co-founders who met in college are the most successful startup founders. Second, by the way, are people who met at a company,

who you worked with. Okay. Co-founders who met at a company because you've kind of had shared experience there. After that is solo entrepreneurs. And then finally, the least successful companies are run by co-founders who don't have any of that stuff. We're bad co-founders. So, Kyle, if you have your best friend as a co-founder, it worked for Nick and me. It doesn't work for everyone. But you want to look for someone who's complimentary to you, someone you enjoy spending time with. And ideally, someone whom you met in college. Maybe you met them in college or at your company or your solopreneur, but don't have a bad co-founder. Okay, by the way, this is kind of a co-opportunity because all the Yetis are out there.

College is looking for a co-founder. Like if any of the Yeties are looking to start a business called, they didn't go to college with them, maybe. But like, this is an opportunity. It's not a dating app. No. But maybe we're a networking app. If anyone is looking for a co-founder, we got one in Calid, who's also looking.

So reach out to us and we'll connect you with Cald. Who knows? This could become a networking connection. That's our meat cute story, by the way. If you are listening and you've got a cool meet cute story with your co-founder, let us know. Hit us up at T-boy pod. Rachel, can we hear the next.

Next question. Next question. What do we got? That first one was fantastic. Second question is from Anonymous. I'm an assistant in the entertainment industry and I just started a new job as a talent rep at a major agency. I'll call it Hollywood Talent.

I took the job out of necessity to pay the bills. A month into the job, my dream company, I'll call it pop pictures, reached out to interview me. My career goal is to be a TV producer and this company makes award-winning TV shows. I've been liking Hollywood talent so I don't want to wear any bridges and it's just a one-year contract. But pop pictures has the prestige and the work that I actually want to do. The pay across both jobs is the same.

Any advice on what I should do with the interview and if I were to get an offer? All right. So this question is basically, I just took a job at one place. Not my dream job. But I have an opportunity at my dream job immediately. Is it okay if I switch jobs so quickly an interview at this place I love? With the risk of, you know, having to tell your current employer, hey, I'm out after just one month. Can I just throw out an answer here?

Absolutely. Absolutely go for. First of all, thank you anonymous for that wonderfully detailed question because I'm sure there's elements of that that resonate with a whole bunch of listeners right now. Absolutely. Absolutely. I agree with Nick. Absolutely. There was a time, you know, I feel like older generations tell us that we should be loyal to our employer. They say job hopping is a stigma.

They say that you're going to be labeled as a job hopper. And that employer to your relationship is like a moral and good thing to do. Those days are overweight. The job hopping stigma is. dead. Okay, for the last three years, we've seen hundreds of thousands of jobs in tech totally get eliminated, even though these tech companies are more profitable than ever. So clearly, they're not worried about loyalty on the employer side. We're just in a different world where I don't think there's an expectation of loyalty. What there is an expectation for

is being forthright and candid and honest. And so if you're going to take this job interview, which we totally recommend you do, there's no downside in that. Do it. Ask a bunch of your questions, figure out if it's really your dream job. And if you decide to take it, be super honest, super candid with the company you're breaking up with and say, this is my dream job. I really hope you can understand and I think they will. By the way, here's another way the whole industry has shifted. Like we were just talking about the job hopping stigma. That was back when a different generation was doing the hiring. True. Right now, the hiring managers, it's not baby boomers and maybe not even Gen X. It's really millennials. And the millennials are

the ones who often got accused of job hopping. But it's now the millennials who are going to sign off on whether you get that job. So that stigma, that's been erased in the hiring decisions too. Yeah. Your career is too important to worry about like the other side. You have to worry about yourself. It's too important to waste at a place that you do not like. My buddy just placed an offer on a home and it got accepted.

And like they're at the point where it's kind of passed no return. His dream house came on the market. And it was just like, oh, he just confirmed. a real estate deal. It hasn't closed yet. Okay. What's your trying to do? He visited the open house of his dream house. He's going to bail on the other deal. He's going to lose his deposit. And, you know, to the anonymous listener who asked the question, the equivalent of losing your deposit is just like, you know, the bad feelings of that moment where you leave the company.

That deposit is going to be a tough conversation. The cost of flexibility. But just like my buddy, you know, is happy to lose the deposit because a house is where you're going to be with your family for the next. X number of years, your future career is too important to worry about the relationship at the company. That isn't even your dream company. Well, here's another valuable lesson from therapy, actually, that applies to both those situations, which is that every decision comes with a cost. Even if it's the right decision, you're probably going to have like a cost with it.

So let's say this person, Anonymous, proceeds with taking the job interview. There is always going to be the risk and the cost that some people are upset at the other firm. But that is the cost of the decision. There's always going to be some kind of cost. Just like the cost of switching houses in this place was the security deposit, financial cost. Like, there's always going to be a cost. If you get worried about there being a cost, it's missing the point. Yeah.

There's always a cost. Is it too much of a cost is the question for you? Not is there a cost. When we were at Robin Hood, I remember I was a little confrontation averse. You're afraid of confrontation. I was afraid of it. No. You were scared.

I wasn't afraid of confrontation. I was just, I'd prefer to avoid it. Yeah. You on the other hand. You on the other hand. I was totally fine. I think you, you, I don't know what it was about you, but you really kind of embraced attention, let's say.

I'm totally fine with tension and being embarrassed. You're totally fine with tension. And I had so many just like meetings with bosses and with colleagues that I was, I had a little pit my stomach for. And I was just like, I can't believe. believe we're still pushing on this. Like, if we just let go, it'd be so much easier. But we didn't let go. Partly because you kept pushing. And I was, I was right there at your side believing and kind of trusting that this is a complimentary. Complementary. And we got through it all. And I'm so

glad we pushed because they were important decisions early on when we arrived at Robin Hood, which was going to determine how Robin Hood snacks, our media company, our baby, was going to be get this new company we just sold to. And like, I learned back in our Robin Hood days early on that tension is not something, you know, confrontation, tension. It's not to be avoided. Yes, there's going to be a little discomfort. But if you can get through that discomfort, you'll have better outcomes on the other side. Also, remember that lesson that Lauren taught us that she shared with this once? About enemies. Not everyone's going to like you. Right. It's okay. Like, it's okay if not everyone loves you. If you're going to be successful,

not everyone is going to love you. Yeah. And if you're prioritizing that everyone loves you, that's going to limit your success. It doesn't mean be a jerk, by the way. Absolutely not. No, no, no. It just means that you have to be okay that some people aren't going to like the decisions you make. For example, switching jobs right after you started one, your manager, that job is probably not going to be happy about it.

But that's one of the costs that comes to the decision. Your new boss at the new dream company will be happy. It's going to love you. It's way better. And I was going to say you could tell the dream job that you had the situation and it's tough for you and maybe they'll even sweeten the deal for you. Oh, good point. To help you get over.

Negotiating. to help you get over the tough breakup conversation you're going to have. No, that's a great point. So you're now saying not only take that job, but leverage it to get an even better opportunity. Yeah, it just started this job here. I mean, don't, you know, don't push it too far. But just be honest and be candid. And a little bit of tension.

It's a little bit. All right. Anonymous, that was such a wonderful question. You love that question. Thank you for illustrating your situation with such detail. Go for it. Oh, by the way, quick reminder, if you're listening and you have a question that one of these questions we're answering now, kind of like triggers it in your head. Submit it now. We have a link

in the episode description where you can submit your question. You can also just email Nick and me at Nick and Jack at T-Boypod.com and your question will be featured in a future T-Boy hotline episode next month. Nick and Jack at T-boypod.com. All right, Rachel, what's the next question? The next question is from Jockel Lang. How do I get passionate about the stock market? I have been dabbling with a few stocks, but I have no clue what I'm doing. I want to be knowledgeable about it, but I'm not sure where to start. I think there's two ways I got passionate about the stock market. One was I invested in companies I loved or had a passion for it, which happened to be Ford

at the beginning. I love that Ford is still a family-owned company. 40% of the stock is held by the Ford family. I thought that was like really cool. And they were like long-term thinking. And I just thought it'd be cool to own a company that I actually admire. There was empathy with the company and with the stock. So invest in some companies you love.

And then this is the most important part. Take some wins. You need to like have some wins. to have some wins in the stock market, buy at a certain price, some of your investments are going to grow in value and then sell. And the difference is your gain and celebrate that. Celebrate that win. And what do you do with it? Because I know exactly the example you're going to give. Buy yourself something. Buy yourself something nice. You owned part of a company. You enjoyed some profits while you were with that company and you sold for a gain.

The way to get excited about the stock market is to recognize that your intuition, your instinct, your research, your work, and a little bit of luck, should be able to be seen in something, whether it's an experience or it's a material object that you end up purchasing that game with. So the first gain I had was Ford. I bought $1,000 of stock and I exited with $1,200 of stock. $200 gain, baby. It was my first one. What did I do?

I treated my buddies to a night of dinner. I thought you could do the Roku one. Oh, that's the next. Okay. So that was a few years later. I was going to share this one about you as I was thinking of it. Go ahead. Well, we're at Jack's wedding and we're hanging out.

And we're like, wow, this person makes a really good nigroney. Where is this bartender from? And then Jack's like, this bartender was hired with the gains from my Roku stock. My in-laws put on a wonderful wedding for us. But we splurged on an extra band and some extra instruments. And a Ben and Jerry's ice cream truck. We had a Ben and Jerry's ice cream truck. So there was a little bit of extra cost.

Courtesy of Roku's 100% jump. Roku was my first early, like, real win, like significant. thousands of dollars paid for my open bar with it. How wonderful was that? No, it was lovely. I still remember the Ben of Jerry. And then my last one was, you know, we had some Robin Hood stock because we sold our company to Robin Hood. When the company IPOed, what did I do with that money? Down payment on my house. How wonderful is that? I have the house I'm in right now because of some stock market gains. Remember, the value that you got from the stock, it doesn't disappear. Like if it's an experience, it lives on in your memory and your happiness. If it's a physical thing, you've transferred that value to

something else. And every time you look at that thing, it'll get you excited that, wow, that was really cool that I invested in a company and now I have that thing because I took a risk and the risk paid off. I think that's how you get excited about the stock market. You take some wins. Another way to get excited about the stock market is you're a student of the stock. Become a student of the stock. Tell me more. Like what? I'm picturing Lulu Lemon. Do you remember when you own Lulu Lemon stock and I ended up buying Lulu Lemon stock with you? We became like, students of the stock. We were going to the stores.

We were seeing how the retail layout was. You were trying on those khaki pants. And I asked for this. I asked for the special dressing room. I said, where's the owner's dressing room? Yeah, because you're an owner of the company. And you're saying, okay, I get the retail experience. I think things look a certain way.

That is informing whether you're holding the stock or not. And then once you're curious about that and you're wearing the clothing, you're discussing with people, then you start looking in the earnings reports. So like, when you're buying your first stocks, the way to get excited about it is experience it, feel it, become a student of the stock. Check out the annual report, which is colorful and informative. Sign up for the email investor reports, like notifications. Turn it into a date.

No, seriously, be a nerd with it. You both wear the Lulu Lemon outfits. You read the Lulu Lemon earrings. It's important. You watch some analysts take down the report. Jackal, hope that was helpful. That's how Nick and I got passionate about the stock market. This is Nick and Jack and I both stolen shares a Lulu Lemon.

Rachel, what's the next question? The next question is from Hannah Hogland and Boko Raton. I'm a master's student and I am wondering where you guys find the little details about companies and the stories you cover. I find myself getting overwhelmed in my own research. So I'm wondering if you have a go-to resource that I might not know about. The headline hammer. Headline hammer. It is every day.

Jack and I wake up. And we just shred through dozens and dozens of resources to put together the daily podcast and narrow it down to the three stories for the perfect mix. But that mix of three stories you hear every day in the pod, it starts with us looking at literally dozens of resources. So Nick and I know dozens of sources for financial information. Let's share our favorites. Okay. Well, we actually, we have a tab in our Google Chrome browsers that Jack and I press. And it opens up literally like 50 tabs of stuff.

And then we go through it for like an hour or two days. One of my favorite sources is tech meme. It's an unbelievable site that curates the top news in the tech industry. So it picks the headline that they think is the best headline for the news stories. So like to do the tweets. Apple today reportedly ended their electric car project. Yeah. So there's going to be the headline from Bloomberg.

Because the Bloomberg guy reported the story. Then they're going to curate all the other good headlines about that story. In case you want it from a different perspective. Then they're going to curate the best tweets from the best thought leaders about that Apple terminating their car story. So you're saying it's like, tech name is like our starting point for tech stories. For text stories. Because then we can branch off into all these potential takeaways. And of course, tech.

it's only the tech industry it covers but the tech industry is where all the wealth creation of the last 10 years has occurred. Jack and I have kind of a liberal arts approach in that we take a wide range. We look at the sources that are like your classics, your go-toes, your Wall Street journals, and New York Times, your Bloomberg's.

But I think this is the interesting stuff, kind of like tech meme. We then get into the niche industry things. Like, you're ready? Three words for you. Ready, Jack? Women's Wear Daily. I love Women's Wear Daily.

I'm like, where did you find the story about Sephora. Yeah, the Sephora story. Jack's like, where did you find this story about Selena Gomez's Sephora sales? I'm like, Women's Wear Daily. One of the sites I check every day is Financial Times because they're British. Right.

And it's important to get a different perspective. What's another favorite source of yours? The editorial section of Women's Wear Daily. Oh, here's another one. Car industry? We want to get deep under that chassis of the car industry. Jalopnik. Jalapnik is a blog that really gives you kind of

unique, hot gearhead takes about the car industry. See, any, if you want to know what Jack and I are doing at 5.30 a.m. in the morning. We're in Women's Wear Daily, Jalapnik, the Wall Street Journal and TechMoon, among others. But Hannah, if you've listened to the show, you know we like to push Control F on an earnings tram. Jimatim at Tibeau style. So the earnings call is where Wall Street asks the CEO, any question they want about the earnings report that was just published.

So the earnings report is a great source of information. The earnings call is like 10 times more information. No one goes into the earnings calls. Like, we love going into these earnings calls. Nick and I will go there and we'll just look for unique words that surprised us. And then check and see if it was mentioned more than once. Jack will call me and be like, did he say raccoon again in the target earnings? I'll be like, Jack, I'm looking.

I see another raccoon reference. No, for instance, Scott's Miracle Growth. They used to be a fertilizer company, lawn care company. Your parents may have used Scott's Miracle Grove to grow their lawn. That's what we always thought the company was. And then we discover the words hydroponics and cannabis. are sprinkled across their earnings transcript. Yeties, you're not seeing this on other news networks,

but Jack and I go into the earnings call, we discovered Scott's Miracle Grow, the lawn company has become a cannabis company. So it's a little bit of an art, and it's a little bit of a science. The science is what TechMere does. The art is the blogs we go to to find the hot takes that no one else is talking about.

Rachel, what's our next question? The next question is a voice memo. I'm going to take my jacket off. Jack is trying to be complimentary right now. It's too complimentary. I'm so weak because I'm so strong. I just want everyone to see it with one fuel layer. So let's hear that voicemail.

Hey, Nick, hey Jack. This is Desmond. I'm considering leaving teaching and would like some advice on converting my salary. For example, if I made $50,000 as a teacher and I get the summers off, how would that translate to a business job where I don't get the summers off? I would definitely appreciate it. an increase, but I don't know how to ask for that. Thanks a lot.

You guys. Keep being great. Negotiation. This is a negotiation question. Go ahead. Share some more. I have some other thoughts, but I'm excited to hear the negotiation. On the negotiation set, I think this is the most underutilized part of a job negotiation.

You ready? The reference. Go on. We always wait for the company that is hiring us, potentially, to ask for a reference check. And those reference checks tend to be a black or white, yes or no, just make. making sure you're not crazy, right? I think job candidates should be proactively offering up references who can provide color, which is what the job hiring manager wants.

If you're the job hiring manager, your perspective is, I want to hire this person who's going to be with the company for a long period of time and succeed. And you also are looking at so many people. So how do you satisfy that job manager proactively offering up, hey, I work for this person for eight years. They can tell you more about me relevant to this job than my mother can. So you're saying instead of waiting for the hiring manager to ask you for references, voluntarily give them.

Give them the references ahead of time. It looks proactive. It lets you control the narrative. It definitely shows confidence. And it's going to provide the color that no one else can provide. And at the rate, I've basically heard no one do this. You're going to stand out. Plus chat chit can be your reference.

Yeah. You're like, just text this number over here. So Desmond, I think when you're considering a career switch from T. to something else. That is a big switch. You should consider, you know, I like kind of like three box frameworks. So for a co-founder, the three boxes were complimentary, trust, and enjoy spending time with them.

Yes, yes and yes. When it comes to a career or a job, I think the three boxes are income, impact, and quality of life. Oh, you could have stuck the landing with another eye word. I know. It's going to eat you up a night. I know you. So on the income, you know, that's clear.

You're going to compare the numbers. Right. I mean, teaching is a high impact career. So if you're moving into the insurance industry, you need to consider what's going to be the change in impact because, you know, that's not compensation, but it is part of how you feel. And part of how happy you are is the impact you feel you're making or not. An unquantifiable value, but a value nonetheless. And then finally, quality of life. As a teacher, you do get the summers off.

And that's wonderful if, you know, if you eventually have kids or if you like to travel in the summertime. So you're going to have to try to quantify that in terms of, I don't know, dollars. You know, an economist would try to take all three of those things, income, impact, and quality of life and like dollarize it so that you can compare apples to apples, the teaching job and the insurance job you're considering. Actually, we have some buddies from business school who would try to turn all three into a number and a variable to come out with one number that's like an NPV that determines whether you should do it or not.

Well, when Nick and I were considering selling the company to Robin Hood, which we did back in 2019, That's where we came up with this three box like career. That's true. We'd use it. Yeah. And we thought to ourselves, okay, I think income wise, this will be great. Like we're getting into Robin Hood pre-IPO. Hopefully the IPO and, you know, the stock that they give us for joining the company grows

in value. That would be amazing. So like income, it was a clear check. Right. Impact, you know, at the time, Robin Hood just introduced no commission training. That was really cool. And we were going to reach all of their customers with our newsletter and our podcast. You know, we believe that our podcast is having a positive impact by informing people and, like, delighting them.

Oh, the impact is like the reason why we do this. Quality of life. Yeah. I don't think we got it at Robinette. We worked so insanely hard. We did. Ridiculous hustle culture that we had to experience at Robbins. We were in the tech industry and the media industry at the same time.

We were running a startup within a startup on a rocket ship. We're producing a newsletter every day, just Nick and me. We're producing a podcast every day, just Nick and me. And then the company we worked at threw tons of. of other projects at us that we had to do. So we did not have quality of life there. We got two out of three boxes when we joined Robin Day. We're back to entrepreneurship.

Still turned out to be, you know, a great move for us. So what I'm trying to say is you don't need to check all three boxes. Yeah. In a perfect world, check all three. But those are the three like parts of a career move you should be thinking about. Income, impact, and quality of life. Can I throw another measurement? Does it start with an eye?

It starts with a B. Bezos. What are you talking about? Okay, a great framework, Jeff Bezos used for why he should start Amazon was the like 50 year framework. He basically said 50 years from now, when I'm retired, am I going to regret having made this switch or not made the switch? And he was like, not all the time. Most of the time you regret not taking that leap. And he was like, I definitely at the age of 80 would have regretted that I didn't try to do Amazon.

So Desmond, does the teaching industry, does it light you up and make you feel amazing? Or is it something that's like, what am I doing here? Like I should be doing something different, something more, I don't know, fast pace or innovative, I don't know, 80-year-old Desmond, what do you wish you'd done? You can, if you like focus for a whole afternoon, picture yourself when you're 80. Jack's going to be probably, I would say, even more athletic than he is right now. This guy's going to be throwing double spirals when he's 80. He's going to be running that piano camera.

Middle C! Desmond, picture yourself. And what would 80-year-old you want you to do? Desmond, good. Good luck with the decision. Let us know how it goes. Maybe we'll give an update to the listeners at the next T-Boy hotline next month. Great to hear your voice, by the way. Thanks for the voicemail. The next question is from Stephen Shapiro in St. Paul, Minnesota. As someone in their mid-20s, I have a healthy mix of stocks, ETFs, mutual funds, etc. Besides having an emergency fund,

most of my savings and investments are in the mentioned brokerage accounts. When I need cash for things like a car, which stocks do I sell? One that have taken a loss or ones that have positive returns. Is there other criteria I should consider? I always fear I am going to sell right before the stock pops off. Doesn't everyone. You know what I'm really guilty of Jack? What? And you know this because you're so much better at me is stock hoarding. You know what I mean? Yeah, I know exactly. I hoard a stock like you know people hoard stuff in their home because they're like, oh, I love that t-shirt from that restaurant I went to in the Florida Keys 40 years ago. So they keep all the t-shirts. Next thing you know they've got a closet full of

100 t-shirts. I see stocks sometimes as physical things that were part of my identity in life, and I keep them in my portfolio like an overflowing closet. And I really have trouble letting go. Like, remember when I owned Luckin Coffee stock? Like five years in, baby. I know. And then they got delisted because of fraudulent accounting. And you hand on to the stock. I still could let go. I'm a stock hoarder. So it's hard for me to sell like those stocks. I also think it's hard for you to accept a loss. Yeah, yeah. That hurts. Also, you know what? Jack, this is genetic because my dad does the same thing.

He still owns Tutsi roll stock. So I think the question of like, should I sell the stocks that are gained versus should I sell the stocks that have lost? I have consulted with like a wealth manager and they've told me it does make a difference because in the long term those are all going to offset. Like you're going to bank your losses and hopefully offset your gains in the long term. I don't think it matters. So don't worry about like the tax consequences. I don't think. It's kind of like the Warren Buffettie thought approach to like not day trading.

You can't time the market with buying it the perfect time and selling it the perfect time. Essentially, don't overthink it. Yeah. And so when it comes to selling the stocks, don't overthink it. Agreed. Yeah. And Warren Buffett would, he like never sells. We covered that on a pot.

Yeah. We literally, we said Warren Buffett. And this is a fact. He bought Coca-Cola and American Express stocks over 20 years ago. Hasn't touched him in the last 20 years. Now, I own a significant chunk of index funds. Must be nice. You do too.

Index funds is, you know, financial people would tell you it's the most, it's the best way to invest. Right, because it's buying a basket of other stocks. It's buying a basket of the entire stock market if you do the S&P 500. And your individual stock picks are just never going to do better than that diversified, like, full stock market situation. So anyway, I don't plan to sell my index funds, like, unless I need the cash, like buy house or something. Or send my kid to college. Index funds are actually a great way to do passive investing with monthly savings. So like if you're trying to jump into the stock market or if you're experiencing the stock market,

a nice habit is to you and if you're living with someone, your partner, your significant other, take a little bit of savings every month. And instead of you could debate which stocks that put it in or like a really great way to avoid conflict is we're going to take our savings and put it in an index fund. But if you must sell stock to like to make a down payment on your car, like in this example. liquidity event. would sell the winners. Yeah. Celebrate the win.

Sell a winner so that you can take a win. Like we just discussed earlier, it's really fun to take a stock market win and transfer those gains into something physical that you'll see every day. Or you can keep hoarding the stocks and painfully let them weigh on your conscious for years. That's an option. How cool would it be if Stephen sells a stock that, you know, has gained 100% and buys a freaking car with that? Oh, Steven should update us on this.

This feels like a shout out at the end of this show. Steven sold is Chipotle and is in Boca, baby. Now a quick word from our sponsor. We're now going to go and do some rapid fire questions. So the first one is what era are you in right now? I'm in the post former dink era. No, former dinkwad era. Is that what we're talking about?

I used to be a dinkwad. You're a dinkwad ass. Well, I have kids now. So I'm not a dinkwad. No, but it's a mindset, Jack. It's a mindset. Your mindset is your mindset. is dink.

Double-income, no kids with the dog and some succulents. Jack, you just flew on spirit. You're going big, baby. Rachel, what's the next question? Okay, I'm living in my almond butter era. I'm just splurged on different flavors. Vanilla, maple, I don't care. I just want to enjoy breakfast.

You've never not been in your almond butter era. That's true. There is a skippy spirit. What's the next question, Rachel? What is something you would tell your 25-year-old self? Stop hoarding stocks. Let go beyond meat. Peloton is not going to take over the world with their connected bikes.

Don't buy the stock. Actually, funny story. When Jack and I first met in college, like the third day I knew him, I don't know, we were like trying to have some fun. So I left a note on his computer saying that. It was from future me to me. I left a note on his computer pretending to be future Jack saying, hey, Jack, watch out. Don't go into the library tonight. something will happen.

Future you, you'll thank me later. So Nick managed to go to both a non-Ivey League college and an Ivy League college somehow. He started with me at Middlebury College and then he transferred to Brown. But those two years at Middlebury that we were roommates together, I witnessed some incredible creative writing from Nick.

I've been witnessing this incredible, humorous creative writing since the start. And you see it every day in the pod. That's the same, the same incredible writing. Incredible, right. That's what we love doing on the show. Forget with the original question. What is something that made you feel old?

Your question about, what would you tell your 25-year-old son? Because I'm really, that was a decade ago. Honestly, honestly, I don't feel old and I don't think you look old or seem old. And neither of it seems old. What I love about us getting to do this job every day is how absolutely on the cutting edge of I've never felt younger. Like, I feel I know more now. about what it's like to be 20 than when I was 20. You know what I mean?

Because we have like this experience of being older and appreciating like the experience that's come with that. But also I think that partially because our job is about identifying and observing trends and changes and shifts and all this. And also like we know ourselves better and just we've kind of had this as we're older. We think more about the world around us. I think we analyze things that 20%. 20-year-old's experience in a way that we just didn't when we were 20.

So I feel like we both seem younger and more vibrant than when we were even 20. It's also a pledge of mine to never let myself become like old and grouchy. Yeah. Like that's the stereotype is that when you get old, you get grumpy, right? Mm-hmm. You know, my dad, for example, like, you know, TikTok, what the hell is TikTok? Twitter, you know, all that stuff. Big dead meme.

Partially because we cover the news every day, but also just because we're in touch with current events, we don't like get annoyed at modern things. We embrace them. Right. Great example. We were just talking about how plant-based may have just been a fad. And we even bought beyond meat stock. We consume the product.

But it may have passed. Yeah, we could have called that trend and said, hey, it was actually a fad and been on the right side of history on it. But it was more enjoyable to test, experience it, try it. Like hope that an innovation becomes a thing, regardless of what happens to it long term. And around the side, I'm not judging it. but appreciating it for trying to sign different. What is a book that's changed your life?

The Brooklyn Bridge. We're staring at a bridge right now, the Bay Bridge. Jack's about to tell me about the suspension lines on this thing. I don't know if it changed my life, but the building of the Brooklyn Bridge. I mean, I could go on it for days about this. It happened in 1869. Yeah. They built a bridge across a 1,600 foot wide river, the East River of New York City.

No one had built anything like it before. The bridge is known for being. wide. It was the tallest structure in New York City or North America when it was built. The tallest. Jackson and eyes will walk around and be like, that's a rivet right there. They built the bridge over the course of 20 years. In the 1860s and 70s, they built the freaking Brooklyn Bridge. I just, I love the human accomplishment that that represents. I love that it was a long-term project that cost a lot of money and cost a lot of time, but has been functioning for 150 years and will continue to be an incredible asset to New York for another 800 years.

That book just, it made me believe in big projects and get excited about our human potential. That book, when you talk with the energy about the Brooklyn Bridge, it makes you open your eyes to all these details around that you take for granted that you, when you put yourself back in this historical context, we're monumental at the time and like changed the course of history, but you kind of just take for granted when you're traveling across it. So the Brooklyn Bridge book I read is like 700 pages. I loved it. But it was pretty long. Ken Burns did a documentary on PBS also about the Brooklyn Bridge if you only want to

spend an hour. There's a TikTok 30-second video on this. I need to make that TikTok. Yeah. I'm in the middle of the book right now. So I'm going to tell you the rest of it. Alchemy, right? Advertising executive who ran Ogilvie.

This thing is so chock-full of thought. perspective that economics misses human behavior in such interesting ways. What we think is economically rational doesn't end up happening because humans are not rational. No, we are not. Okay, great takeaway from the book. We don't value things. We value meaning. Example of this?

I hand you a bag. You're like, whatever, it's just a regular bag. Like, what does this bag matter? But if I tell you that that bag was carried by Marilyn Monroe, you have a very different appreciation for that bag and you'd probably pay a different price for it. Same bag. Nothing's changed about the bag.

All that's changed is that Marilyn Monroe used to hold it. And that's why we don't value things. We value their meaning. I mean, how about, you know, a designer handbag. Exactly. We're buying it for the logo. Yeah. And the status symbol that exudes.

It's all about the feeling. All right. This is our last rapid fire question. What is too early for a meeting? We haven't been very rapid fire in our responses. These are long form. This is the long SATs here. We're terrible on following our own shows.

Turn paper responses. How early is too early for a meeting? Well, 7.30. You know what's a funny thing about this question? It reveals an East-West Coast bias. True. You know? Jack and I have discovered this.

Jack being on the East Coast, me being on the West Coast is, it is amazing to me. Having grown up in New York City and not realize this at this at this time, the whole world revolves around the East Coast. The whole world revolves around the East Coast. It's awesome being on the East Coast.

It's awesome being on the West Coast, having football games start at 10 a.m. Yeah, it's great. You're like, wake up, you're having breakfast and you're, you know, your half time. The Super Bowl is at three. It's incredible. Yeah. And then you, like, go for a run and then you have dinner. Yeah. But also with, like, meetings and work, everything begins before the sun rises.

Like, Jack's crashing my place right now in San Francisco for the week. And remember, we, like, looked out the window. Everyone was going to work at, like, 5 a.m. You could hear the cars getting out of the driveways because everyone in the West Coast is, like, you're a little bit geared toward the East Coast. In other words, 7.30, which is too early for me. on the East Coast is nothing for you. Right. It's like you're up early

to match East Coast time. Yeah. So it's really time zone dependent. And the world revolves around New York. Yeah. Okay. First rule, if your boss sets up a meeting that's too early,

camera off. Camera off. Don't even think about keeping that thing on. Now, didn't say naked, just said camera off. Right? Like, you want to be prepared for any kind of Google Hangouts

malfunction, Zoom issue. Yeah. But you're not keeping the camera on if it's before 9 a.m. And if you get scheduled for a meeting after 6 p.m., camera off, you're phoning into that thing. Take your dog for a walk. Enjoy the outdoors. No one expects you to be behind your computer.

Biggest legacy mistake of the pandemic is that you have to be doing a Zoom-style video meeting all the time. Studies show how exhausting that is just trying to like keep your smile up for the entire meeting. Take a phone call walk. And if we're talking about work-life balance. Hit me, Jack. Where are you going with this?

What was the best thing we did to ease our quality of life at Robin Hood? What was it? What was it? We deleted slack from our phones. Oh my God. This was so funny. Jack and I, like literally one day we said, what happens if we delete slack? From our phones.

From our phones. We thought birds would fall from the sky. We thought time would stop as we know it. Instead, yes. The message was waiting for us when we opened our computer. And no one complained. And we were able to actually disconnect when we closed our computers. And if there was something urgent, guess what?

Our Slack profile had our phone number. People called us. And he called us. So, Yetis, the takeaway for our buddies who may have a 601 p.m. meeting on a Friday, what is it, Jack? Or 749.29 a.m. Delete Slack, turn off the camera, take a walk, and make it a phone call. I just whipped up the takeaways, Jack's time. Okay.

So at this part of the show, we usually do the best fact, yeah. We usually whip up the best fact yet for the Yeties. But for T-Boy Outline, you are hitting us up with the best fact yet. Trivia style. It's the reverse best fact, yeah. So we got this trivia question sent in by a bestie, but it's still the best fact. Push and play. This is from Jack Leonard.

Trivia question for you. What do the 2019 films Knives Out, Joker, and Marriage Story all have in common? Okay, Knives Out obviously involves knives. In marriage story, Adam Driver gets cut by a knife. I feel like we need some kind of like a boy. reception board where we're getting everything together. Like a detective with all the lines connecting the suspects.

What was the third movie? Knives out, a marriage story, and, oh, knife. Joker had knives coming out of his shoes. The Joker. I think there's a knife connection across all three. Do you have any ideas? I... They all involve a plot twist two minutes before the whole thing ends.

That gives it all away. Let's hear the answer. And here's your answer. All three movies feature a song from the late, great, legendary composer Stephen Sondheim. Marriage Story has Being Alive from the Musical Company. Knives Out has Losing My Minds from the Musical Follies. And lastly, Joker has very appropriately send in the clowns from the musical A Little Night Music. I was way off with the Knives.

Besties, Yetis, that was the first episode of T-Boy Hotline. Thanks for calling it to the T-Boy Hotline. I absolutely loved it. We had a blast. Thank you for the wonderful questions, and we hope to do this month like you. You're looking fantastic, by the way. If you have a question for Nick and me, hit us up at Nick and Jack at T-boypod.com. The T-boy Pod hotline.

Email us at Nick and Jack at T-boypod.com. The best hotline yet. Nick and I will see you next month for T-Boy Hotline episode. If you know, you know. So, Nick, did I tell you I had the most challenging airplane flight of my entire life? The one you just did? It was the one from Vermont to Florida. It's impossible to get from Vermont to Florida.

That's impressive because your flight from Florida and San Francisco sounded rough, no internet. And your flight previously back from San Francisco had no window. Yeah, I've been having some troubles. But, so we decided to drive to Boston because it was a direct flight from Boston. Because you've had so many bad flights. Yeah. So that was mistake number one. Okay.

It's a four-hour drive. Yeah, yeah. The Gilligan Island situation. The state number two was deciding to pay for economy parking. What am I doing? You got to upgrade your life. I searched 20 minutes to find the economy parking lot. Then I arrived at the economy parking lot.

Spent 20 minutes looking for a parking spot. Then I parked and spent 20 minutes looking for the shuttle, which I had to take to get back to the terminal. Long story short, first flight I ever missed. And I missed it with two top. Missed my flight. Missed my flight. Missed it with a toddler, a newborn baby,

my wife Alex and an extremely nervous dog who had just taken a Xanax. Well, at that point, you can't... You ready for mistake number three? Yeah. We're flying Spirit Airlines. Now, to their credit, they were wonderful. They told me that there was a flight leaving in just an hour, and they were going to transfer all of our reservations, five souls.

Alex, me, two boys and the dog. Oh, my God. No charge. The dog is zonked out at this point. Yeah. So I missed the check-in time by four minutes for the first flight. So I missed my first flight by four minutes. But you actually could check bags this time.

I'd check bags. And then the next flight was only an hour later. It worked out kind of wonderfully. So getting to the airport was a disaster? The best flight you ever took. Spirit Airlines. So you're flying Spirit again? Yeah, we're flying back on next Tuesday.

There you go. Same flight back to Boston. Good luck. Good for you. Yeah. Guess what? I'm flying on my birthday back. Why do I keep making all these mistakes?

That's a mistake number four. I don't think spirits like in a... Sing a song for you. This is your captain speaking. Before everyone puts into their own rough and unlocked position, can we get a happy birthday for the passenger in 7B? That's my spirit airline story. Yeah.

Well, I'm really happy you survived to tell the tale.