When to Sell Your Stocks, and How to Survive a High-Pressure Job

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1:32Scott Galloway:Welcome to Office Hours with Prop G. This is the part of the show where we answer questions about business, big tech, entrepreneurship, and whatever else is on your mind. If you'd like to submit a question for next time, you can send a voice recording to officehoursofpropgmedia.com. Again, that's officehoursofpropgmedia.com. Or post your question on the Scott Galloway subreddit, and we just might feature it on our next episode. Question number one. Hi, Scott. It's Jim from Connecticut. My question is how much you consider tax consequences when you're weighing selling a stock position or repositioning your portfolio.

2:04Specifically, I have a diversified stock portfolio worth about$3 million with a basis of about$1 million. For all the reasons you talk about on Prof. G and Pivot, I'm extremely nervous about where the world and markets are heading, and I would like to sell a large chunk, if not all of my stocks at this point. For reference, I'm 63 years old, and my stocks represent about 25 % of my overall net worth. I also hold real estate, bonds, and cash. Though my gut is telling me to sell all or a large portion of my stocks, the state and federal capital gains tax of approximately 20 % is holding me back.

2:38How do you factor capital gains in your decisions? Does it dissuade you from selling a stock or repositioning your portfolio? If my gut is telling me to get out, should I bite the bullet and pay the 20 % exit fee on the gains? Appreciate you and your various pods. I'm a big fan and always appreciate your perspective. Thanks, Scott.

2:57Scott Galloway:Thanks for this, Jim. And my thoughts are mostly a function of where I've gotten it wrong. So what you're trying to do here, quite frankly, is time the market. And that's not a good idea because while I would argue the market is fully valued, and I'll come back to that, Nobody knows. And when guys like me are saying the market is fully valued, it has a habit of going up 20 or 40 percent. It's very hard to time the market. And I think you will always want to be in the market. Tax, I spent a lot of time thinking about tax, and I think it's important. And if you hold it, if you have a stock that's gone up and you're planning to sell or you need the cash and you've held it 11 months, you absolutely want to hold it 12 months so you get long term capital gains.

3:37And in general, one of the greatest wealth hacks in history is the ability to buy equities and let them compound tax deferred.

3:46Scott Galloway:And then if you want to do the trick of billionaires, if you need cash to fund your lifestyle, maybe you borrow against those stocks, not more than, say, 20, 30, 40 percent max to fund your lifestyle. And you can get a very good interest rate usually. And it's a margin loan. And then ideally, the stocks keep going up and you get to compound off a higher base. And there's sort of the life hack or the wealth hack of the rich is buy, borrow, and die. And that is you buy your stocks. You never sell them. You borrow against them. And then when you die, you get a step-up basis and you get to sell them or put them into your trust and your kids inherit them and don't have to pay taxes on the gains.

4:26Scott Galloway:So now you said something that really helped. And that is you gave me some color here around your situation. and that is you said you have a stock portfolio worth about 3 million, you're 63 and your stocks represent about 25 % of your overall net worth. So I would argue that you're actually pretty well positioned. It sounds like you're a smart guy. First off, it sounds like you're successful if you have 3 million in stocks and that's 25 % of your overall net worth. You're not only very talented at what you do, but you've been very disciplined and smart and probably started investing early and think about this.

5:02Scott Galloway:And you have leveraged what is the most unreported investing hack. The key lesson I did not learn, and that is the big D, diversification. So having three quarters of your assets and other things that are differentiated, nothing is fully non-correlated. In the 80s, finance professors realized you could get risk-free return by diversification that because of demographics and productivity, on average, the markets go up and to the right over the medium and long-term usually. So rather than taking risk on a concentration of stocks, you know the stocks will most likely, or you don't know, will most likely go up if you have diversification.

5:44Scott Galloway:And so they did the analysis and said on a risk-adjusted level, diversification is just an incredible hack. And it also just psychologically is really important because there's nothing like thinking you're a genius and going all in on a stock, and then three weeks later it gets cut in half and you just hate yourself. So let me talk a little bit about what I'm doing. I think the markets are wildly overvalued right now, but I'm still in the markets. What I do is I make sure I'm diversified. I like you. It sounds like we have kind of a similar investment portfolio. I think I have about, what do I have?

6:14Scott Galloway:I think I have about 20 % of my net worth maybe in stocks. And the reason I don't like to be in stocks or one of the reasons is I like being in private assets because I don't have a mark every day. The scorecard is stressful for me. I'll check my stocks when I get off the podcast today because as long as the data is there, it's like being obsessed with your sleep. At some point, you get so stressed about your sleep number, you have trouble sleeping. So the way your Kevlar, when the markets go down, is diversification. But it sounds like you have done that. And trying to time the market with your stocks is usually very difficult.

6:48Scott Galloway:You always want to be in the markets. Have liquid stocks and some cash to survive six or 12 months. Should shit really get real? But for the most part, I think you always want to be in the markets. And my gut is based on the fact that you've already done what you're supposed to do. And that is you've diversified as long as you're sort of diversified within those stocks. And that is, you know, hopefully it's not in one stock. It's in several and different sectors. But my brother, I would say that you're trying to do something that nobody can do. And that is time the market. If you were saying I'm an employee at Anthropic and 98 % of my net worth is private Anthropic stock, I would say hit the secondary markets and sell as much as you can and take the tax hit and diversify.

7:34Scott Galloway:But that's not you. You're well diversified and it is very difficult to time the markets. And the question is, what do you think you can invest in right now that would potentially outperform the stock market right now, given that you would take a tax hit so you'd have to get an even higher return? And the fact that you're only one quarter in the public market says to me that you should probably, and this is my favorite strategy, do nothing. Thanks for the question. Question number two. Hi, Scott. Mathieu from France here. I've been reading your stuff and listening to you for about five years. I really like what you do, so thank you.

8:16I'm going to be starting a job in investment banking soon, and I'm very happy about the job, but I'm also a bit anxious. I was wondering if you had any advice for the job, or more generally, for high-pressure, long-hours job. Thank you, Scott.

8:35Scott Galloway:Well, congratulations. If you got a job in an investment bank, so we did the same or doing the same thing. I right out of UCLA, I got a job at Morgan Stanley and their analyst program at Fixed Sink Club. And the reason I got it was my roommate my senior year was who I was very competitive with desperately wanted a job in investment banking. I was like, that was his dream. And so I thought if he wants it, I'm going to do it. And I actually got a job with Morgan Stanley. I had no business being in that group of people. I didn't know what investment banking was. I hadn't done especially well in finance.

9:04Scott Galloway:Look, action absorbs anxiety. So what you want to do is you want to control for the things you can control. Whatever division you're going into, start reading up on it. Use AI to understand the deals. Start, you know, if you're in the IPO group, start reading prospectuses. If you're in fixed income, start following the credit markets. Just get very adept at it. And then the reality is just show up 10 minutes before everybody else and leave 10 minutes after. And people say, well, that's a toxic work environment. No, that's just the work environment of investment banks. Essentially, investment banks have this compact with their youth or with their entry-level employees.

9:40Scott Galloway:We own your ass. You're not going to have really much time for relationships, much time for physical fitness, much time for hobbies. You can pretend to have a hobby, but let's be honest, you're not going to have time. You're going to work. You're going to literally work around the clock. But here's the thing. At 22, you can do that. And when I was 22, I had no dogs, no kids. I was living with my mom, and I wanted to make money and get credentialed and set myself up for a future where I would have more economics such that I could spend more time with my dogs and kids. And some people call that a toxic work environment.

10:14Scott Galloway:I used to go in, no joke. I thought, okay, I'm not as well educated as the rest of my peers. And I wasn't, not because UCLA wasn't a great school, but because I got a 2.27 GPA and spent the majority of my time learning lines from Planet of the Apes or making bongs out of common household items. I was very good at that, actually. Did you know you can make a fantastic water bong from a sparklet, one of those big sparklet swatters, also an apple, toilet roll, tin can, there's an aluminum can, there's a lot of things that you can figure out a way to combust marijuana with. Why does that make me happy?

10:50Anyways, so I was insecure about an anxious, but I can control.

10:58Scott Galloway:There's certain things I can control. This is what I decided to control. I used to go in Tuesday morning at 9 a.m., and I would leave at 5 p.m. on Wednesday. I was in great shape. I had learned how to push myself beyond all reasonable limits because I'd been on crew, and I had nothing to go home to. And it also helped me stand out. Maybe I wasn't as smart as the rest of everybody. Maybe I wasn't as well-educated. But I showed I kind of came to play. And I knew I could do it. It just wasn't that hard for me to work through the night. I have that skill or whatever, endurance, what it is. Actually, everyone, almost every 22-year-old has that skill.

11:34Scott Galloway:They just don't believe it. You don't realize your limits until you test them. And one of the unfortunate things about 98 % of us now living in this type of advanced economy is we are never forced to really test our limits. We're comfortable. And the reason we offer comfort is humans will do almost anything to avoid pain. And also the trappings of a modern society is that you don't have to have teeth pulled out without the benefit of Novocaine. So the problem is you never really oftentimes test your limits. Because when you test your limits, what you realize is that your mental and physical limits are well beyond anything you could imagine until you test them.

12:12Scott Galloway:And so I decided to leverage that I knew that and work really hard. and people will claim that the environment I'm talking about is a toxic work environment. I think that term is overused. And that is typically when someone is saying the work environment was toxic, they're saying that it wasn't the work environment I want. Fine, guess what? The compact or the agreement that you're gonna have no life outside of work, you're gonna work your ass off, be exhausted, mentally fatigued. And in exchange for that, there's a chance that by the age of 30, you're gonna be making more money and have more responsibility than your parents did at 50.

12:47Scott Galloway:There are millions of young people who will raise their hand, including me, and do that. And that's an amazing culture. By the way, the culture I just described is the culture of the majority of the really successful growth companies. They're not about balance. That's just not why you're there. And that might not be for you. You may want to go to work for Levi Strauss & Company, which has a very maternal culture. You know, summer Fridays. ways, you know, everyone's encouraged to take time off and back. Great. Have at it. That's a great. There are people, really talented people who are drawn to that culture and want more balance in their lives.

13:26Scott Galloway:Then there's other people like, fuck that. Let me run. I mean, let me really run and make a lot of money. So anyways, my point is action controls anxiety or action absorbs anxiety. Read up on the space you're going into. Realize that the screening process for these companies is very, very rigorous. And you're there for a reason. You are good at what you do. And everybody else that's going in is having the same anxiety you are. Just show up early. Be on time. Look good. Be prepped. Try and be really supportive and friendly with your colleagues and your peers. Try and figure out almost right away with your boss, what is something you could do to save them time every day?

14:12Scott Galloway:Like what is something that would just make their life a little bit easier that they're not thinking of? Take initiative. Don't wait to be asked to do stuff. You know, try on a regular basis, go the extra mile. Attention to detail on investment bank. I sucked at that initially and I realized, and that was a great training for me because it demands it of you. Read everything frontwards and backwards. words, become, if you can, very anal retentive and double check and triple check everything. And that stands out and is kind of mandatory at investment banking and consulting firms on a regular basis.

14:44Scott Galloway:Speaking of toxic work environments, I would pull together every one of my consulting firm, profit brand strategy, and I would show work that had mistakes in it. And I would embarrass people. Is that wrong? Probably. It was also very effective. And I said, everything that leaves this building has to be perfect, has to be perfect. and you need to bring the same vibe to an investment bank. But look, you're there for a reason. You're very, you're obviously very qualified and can do the work. Control what you can control. Show up, be there five minutes early before everyone else, leave after everyone else does.

15:17Scott Galloway:Stay in good shape, eat good nutrition, but realize the next few years are probably about trying to get some launch trajectory. Careers are like projectiles into space. And that is 97 % of the fuel is expectorated trying to get out of the soupy inner atmosphere. It's the same way with your career. It's sad, but the trajectory set in your 20s kind of sets the trajectory for the rest of your career. Is that fair? No. Is it true? Yes. So burn a lot of fuel. Go into it with a bit of a warrior mindset. And I'm not saying that's the right way. It's my way, but it sounds like you've chosen that route by going into investment banking.

15:53Scott Galloway:And there's huge reward and upside. The market is good at figuring out the ROI. If you want to have balance and go somewhere else, fine. You're not going to make as much money or probably have as much opportunity. And that might be right. But clearly, you've decided not to. You're there for a reason. And congratulations. If you're at an investment bank, it means you've done really well. These are some of the most aspirational jobs in the economy. And you are there for a reason, my brother. Thanks for the question. We'll be right back after a quick break.

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19:25Scott Galloway:Welcome back. Question number three comes from a listener who emailed us. Hi PropG team, I'm a cancer survivor. while my prognosis has continued to improve, surviving has come with a significant financial cost. Despite these challenges, I've dedicated my time to supporting my elderly aunts by visiting and helping them personally. However, other family members are now pushing back, suggesting that the right way to help is to hire professional caregivers rather than providing the care of myself. I have been moved by your openness regarding your experience with your mother. My question is, how do you think about this?

19:54Scott Galloway:Is there a right answer between showing up personally versus paying for professional care, especially when financial resources are limited? Thank you for everything you do. Your work means a lot to me. It's a really nice message. And first off, the fact that you're even asking this question means that you're just a good person. I just, the reason why we want relationships is because they're the most rewarding thing to do is to love and to care for other people. And also when you're at your most vulnerable, that ROI is that people are there for you. And it sounds like you are there for your elderly aunts.

20:29Scott Galloway:I'm going to guess this is a woman. Women tend to be better caregivers or more nurturing. That's probably a hate crime. People probably say that, oh, they shouldn't be COs. No, I'm not saying that. I'm just saying typically, typically a lot of the domestic and emotional burden falls on the daughters. It shouldn't, and it should not be normalized. I'm not saying that, but it usually is. Look, there were a few things about when my mom was dying. I was in a different space. I think it sounds like I already have more professional trajectory than you. I was in NYU. My mom raised me on her own. It was just me and her literally against the world.

21:07Scott Galloway:So I took a leave of albums from NYU. I moved into her retirement home. And I lived with her for about eight or nine months. Death is a weirdly weird thing. It's very persnickety. I was told in the first month that this is the weekend she's going to go. And she went. She lived for eight months. It was actually quite a nice time in my life. A strange time in my life. Let's talk about me. During the day, I would manage my mom's health care. You know, when she was diagnosed for the third time with cancer, I said, all right, what do you want? What's your bucket list? And she said, I just want to die at home.

21:38Scott Galloway:And I said, okay, I have some resources and I'm creative. I'll move in with you and we can figure that out. And during the day, I would manage her health care. She had a friend, a wonderful friend, a woman named Carson, who was a rabid alcoholic with a little Scottish terrier. He used to make out with the maintenance workers. I'd come home and she'd be topless making out with a guy with a big patch that said or a big name tag that said Carlos, who was cleaning or blowing the leaves outside of our backyard. Which was the weird thing is it didn't even seem that weird. That environment was such a fucking freak show that when I came home and saw this 78-year-old woman with enormous enhanced breasts shooting up like the fucking Twin Towers and a guy fully clothed in a maintenance uniform making out with her on the couch.