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

Scott Galloway explains why you shouldn't try to time the market, how to survive the punishing culture of a high-pressure job, and how to care for an aging loved one without giving up your own life. Want to be featured in a future episode? Send a voice recording to [email protected], or drop your question in the r/ScottGalloway subreddit. Plus, you can now call or text Scott a question at our new Office Hours hotline: ‪(201) 472-3656‬. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:01Speaker 00

  Megan Rapinoe here. This week on Why Are You Like This? I am talking with comedian Amber Ruffin. We dig into all the twists and the turns of her journey from losing the White House Correspondence Dinner and missing out on SNL to becoming a writer for Seth Meyers and getting her own Peacock TV show. Plus, I'm giving you a behind the curtain look on Rebecca Hunt's documentary about me. Check out the latest episode of Why Are You Like This? Wherever you get podcasts and on YouTube.

• 0:32Speaker 00

  Hey, it's Sue Bird. This week on Bird's Eye View, I'm joined by Jessica Shepherd of the Dallas Wings. Jess and I get into how playing overseas helped her rediscover her love of basketball, why Paige Becker is one of the best teammates she's ever had, and what the Wings need to do to find success in the playoffs. Plus, in Sue's view, I share my thoughts on the 2026 WNBA awards race, including the contest for MVP between this season's front runners, Asia Wilson, Kelsey Mitchell, and yes, rookie Olivia Miles. Check out this week's Bird's Eye View on YouTube and wherever you get your podcasts.

• 1:06Speaker 00

  Hogging seats on a crowded train, not saying, excuse me, watching videos on your phone with no headphones in. Sometimes it feels like we don't know how to act anymore.

• 1:17Speaker 01

  What we have been seeing increasingly is people breaking rules. Why should I play by the rules if nobody else is going to do that for me?

• 1:26Speaker 00

  This week on Explain It To Me, how to mind your manners. New episodes Sundays, wherever you get your podcasts.

• 1:41Scott Galloway?

  Welcome to Office Hours of Prof G. This is the part of the show where we answer your 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 officehoursofprofgmedia.com. Again, that's officehoursofprofgmedia.com. Or post your question on the Scott Galloway subreddit, and we just might feature it on our next episode. Question number one.

• 2:03Speaker 03

  Hi, Scott. It's Jim from Connecticut. My question is, how much you consider task consequences when you're weighing selling a stock position or repositioning your portfolio? Specifically, 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.

• 2:48Speaker 03

  How 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.

• 3:06Scott 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%. It's very hard to time the market, and I think you always want to be in the market. Tax, I spend a lot of time thinking about tax, and I think it's important. And 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 such that you get long-term capital gains. And in general, one of the greatest wealth hacks in history

• 3:51Scott Galloway?

  is the ability to buy equities and let them compound tax-deferred. 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% at 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. 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.

• 4:35Scott 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 have probably started investing early and think about this. And you have leveraged what is the most unreported investing hack.

• 5:18Scott Galloway?

  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 that 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. 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

• 6:02Scott Galloway?

  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 I have a kind of a similar investment portfolio. I think I have about, what do I have? 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's there. It's like being obsessed with your sleep. At some point, you get so stressed about your sleep number, you have trouble sleeping.

• 6:44Scott Galloway?

  So the way you're 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. You always want to be in the markets. Have liquid stocks and some cash to survive six or 12 months should 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, hopefully, it's not in one stock, it's in several in 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.

• 7:28Scott Galloway?

  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. 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 could 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 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.

• 8:12Scott Galloway?

  Question number two.

• 8:14Speaker 04

  Hi, Scott. Mathieu from France here. I've been reading your stuff and listening to you for about five years, and I really like what you do. So thank you.

• 8:25Speaker 04

  I'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.

• 8:44Scott Galloway?

  Well, congratulations. If you got a job in investment banking, so we did the same or are doing the same thing. Right out of UCLA, I got a job at Morgan Stanley in their analyst program at Fix Bank. And the reason I got it was, my roommate my senior year, who I was very competitive with, desperately wanted a job in investment banking. 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. 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.

• 9:29Scott Galloway?

  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, their youth or with their entry level employees. We own your ass. You're, 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, 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

• 10:13Scott Galloway?

  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. I'm, 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's, one of those big sparklet's waters? Also an apple, toilet roll, tin can, or aluminum can. There's a lot of things that you can, you can figure out a way to combust marijuana with.

• 10:58Scott Galloway?

  Why does that make me happy? Anyways, um, so I was not, I, I was insecure about and anxious, but I can control. There's certain things I can control. This is what I decided to control. I used to go in Tuesday morning at 9:00 AM and I would leave at 5:00 PM on Wednesday. I was in great shape. I had learned how to push myself beyond all reasonable limits because I've 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, to work through the night. I'm, I, I have that skill or whatever endurance, what it is. Actually, everyone, almost every 22 year old has that skill.

• 11:43Scott Galloway?

  They just don't believe it. You, 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 teach our, uh, test our limits. We're comfortable. And, 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, without the benefit of Novocain. So the problem is you never really oftentimes test your limits. Cause 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. And so I decided to leverage that I knew that and work really hard.

• 12:26Scott Galloway?

  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, or the agreement that you're going to have no life outside of work, you're going to work your ass off, be exhausted mentally, mentally fatigued. And in exchange for that, there's a chance that by the age of 30, you're going to be making more money and have more responsibility than your parents did at 50. There are millions of young people who will raise their hand, including me, and do that. And that's, 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.

• 13:10Scott Galloway?

  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 and Company, which has a very maternal culture. You know, summer Fridays, you know, everyone's encouraged to, to, 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. 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 this, the space you're going into.

• 13:51Scott Galloway?

  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, 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, with your boss, what is something you could do to save them time every day? Like, what is something that would just make their life a little bit easier than 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.

• 14:34Scott Galloway?

  I, I sucked at that initially and I realized, and that was a great training for me because I, it demands it of you. Read everything frontwards and backwards. 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, you know, toxic work environments. I would pull together everyone in 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.

• 15:19Scott Galloway?

  Control what you can control. Show up, be there five minutes early before everyone else, leave after everyone else does. 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, soupy inner atmosphere. It's the same way with your career. It's sad, but the trajectory set in your twenties 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. Like 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. And there's huge reward or an upside.

• 16:04Scott Galloway?

  All, 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.

• 16:37Scott Galloway?

  Support for the show comes from Superhuman. The pace of modern work can be relentless. You're getting a constant influx of messages from a ton of different apps. You haven't closed all your browser tabs in a year. Everything seems urgent and staying on top of it all feels like an impossible task. Superhuman Go is an AI chat that's always there when you need it. Already aware of what you're doing and doesn't ask you to start from zero. Superhuman Go, from the makers of Grammarly, help you be the best version of yourself at work. It handles the repetitive stuff so you can focus on the work that only you can do. Whether you need to summarize an endless email thread or prep for a meeting that's happening in five minutes, Superhuman Go works inside the tools and sites you already use, your browser, inbox, docs, and your project tools. And its AI chat is available on the side of your browser and it's always ready.

• 17:22Scott Galloway?

  No new tabs, no switching apps, no losing your place. This is AI that works with you, not on top of you, so that you have the time and brain space to solve the problems that matter. Check it out, find out more at superhuman.com.

• 17:40Scott Galloway?

  Support for the show comes from Upwork. Trying to scale your business? At some point, you're probably going to hit a point where you need some help. Sometimes the best way to break through that is bringing in the right talent at the right time. Upwork can help. Upwork is a one stop platform where you can find, hire and pay expert freelancers across more than 125 categories. Whether you need specialized skills for a single project or extra support to keep up with demand, it's easy to connect with experienced professionals, review their work and find the right fit. You can move faster without taking on the commitment of full-time hires. And for businesses that need the very best talent, Upwork Business Plus provides access to the top 1% of freelancers on the platform. AI-powered matching connects you with qualified candidates in under six hours, cutting down the time spent searching.

• 18:23Scott Galloway?

  Upwork also takes care of contracts, payments and other administrative tasks. So you can spend less time managing logistics and more time focused on what's next. Visit upwork.com/profg right now and post your job for free. That's upwork.com/profg to connect with top talent ready to help your business grow. That's U P W O R K dot com slash prof G, upwork.com slash prof G.

• 18:51Scott Galloway?

  Support for the show comes from Vanta. As AI adoption grows, so does your company's security risks and requirements. New frameworks, audits and vendors keep piling on, but your team isn't getting any bigger. Most compliance tools promise automation, but you're really stuck doing all the work by hand, chasing screenshots, validating controls and playing catch up when audit season comes around again. Vanta works differently. The regentic trust platform is built to scale with you, not slow you down. With over 1,400 automated tests across 400 plus integrations, Vanta collects evidence and monitors your controls year round, cutting your audit prep by 82%. Plus, you can access the Vanta agent everywhere you work, whether your team is in Vanta every day or living in tools including Claude or Cursor. Want proof?

• 19:36Scott Galloway?

  Over 16,000 fast growing companies like Ramp, Rider and Harvey save time and resources while scaling fast with Vanta. Learn more at vanta.com/profg and get a thousand dollars off. That's spelled V A N T A dot com slash prof G for a thousand dollars off.

• 20:00Scott Galloway?

  Welcome back. Question number three comes from a listener who emailed us. "Hi, Prop G 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 myself. I have been moved by your openness regarding your experience with your mother. My question is, how do you think about this? 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

• 20:45Scott Galloway?

  means that you're just a good person. I just... The reason why we want relationships is because 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. 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 CEOs." No, I'm not saying that. I'm just saying 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

• 21:29Scott Galloway?

  a few things about when my mom was dying. I was in a different space. I think I... It sounds like I already had 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. So I took a leave of absence 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. She... 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." And

• 22:13Scott Galloway?

  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, I'm like, "Oh, this fits.

• 22:54Scott Galloway?

  This fits." Anyway, she showed up in a canary yellow Corvette, my mom's friend Carson, with a bunch of Johnnie Walker bottles clanking around the back and a Scottish terrier. And she would make us Hot Pockets every night. And I would check in with her, and I love Carson. She passed away about 20 years ago. Rabid alcoholic, addicted to opiates, forgot to get her opiates, heart gave out. Anyways, but there were just certain things. I'll always love Carson, and I tried to be good to her because she showered my mom. And as soon as she heard she was sick, she got in her Corvette and drove to Vegas to Summerlin.

• 23:34Scott Galloway?

  Anyways, my learnings: Care for the caregivers, right? Because it sounds like you're going to have other people involved. Two, have boundaries. This is not your mom or dad. And I think it's very noble what you're doing, but they're your aunts. And I think you want to participate and help, but I think you have an obligation to yourself and to your kids, or future kids, to establish some momentum in your life. I used to leave every Thursday and go stay in Miami because I wanted some semblance of a life. And several times, the nurse would say, "This is probably the weekend she's going to pass." And I would leave anyways because I wanted a semblance of life, and it wouldn't happen. And by the way, on one

• 24:16Scott Galloway?

  of those weekends, I met the woman who I would, 18 months later, have a son with. So I kind of... I hate to say this, and this is going to sound unfeeling, but if you're a young man or woman trying to establish a professional trajectory, I think you stay involved and you help out. But I think your aunts would want you to have your own life. And I don't know the financial situation. I don't know if you're the only person there that's able to do this, but you have an obligation to form your own family, your own life, your own economic security. And I think it sounds to me like the balance has swung a little bit too much. I don't think you should be a long-term caregiver unless that's your

• 24:57Scott Galloway?

  profession for your aunts. And I recognize this may be a difficult situation, and you may be the best person to do it, but I would imagine your aunts want you to develop your own life. So should you be involved? Should you help out? Yes. Should you be a full-time caregiver? I don't think so. And I know that might sound unfeeling, but I think you should be working on and leaning on other family members, including their kids and their siblings and their... to say, "How do we do this?" And I'm willing to participate, but folks, it's going to take a village because I need to get on with my life. So I don't think that's being selfish. And I would imagine, again, that your aunts want that for you. I would need more context on the exact situation. And unfortunately, health care in our nation

• 25:42Scott Galloway?

  is so fucked up that sometimes, you know, it sort of falls downward to the one family member that has the skills and the capability and the resources to do that. But I think you got to figure something out such that you can pursue your own life and establish your own relationships and your own economic security such that you don't need to lean on a niece to take care of you when you... You know, this is coming for all of us. This is coming for all of us. I think this is a conversation with other stakeholders, family members, such that you can participate. You can participate, but you should be entitled to, and they should expect that you have the bandwidth to pursue your own professional

• 26:25Scott Galloway?

  life and your own family over the medium and long term. Let me finish where I started. You're obviously a good person. Caregivers are... What's interesting is they live longer. Supposedly, a hormone gets released, and you live longer because that's essentially this species saying that you're really important. And let's be clear, what you're doing is really important. But it sounds to me like you've given it the office, and you need to think about your own life and developing your own family. Again, thanks for the question. And I just think it's very honorable what you're doing.

• 27:05Scott Galloway?

  That's all for this episode. If you'd like to submit a question, please email a voice recording to [email protected]. Again, that's [email protected]. Or if you prefer to ask on Reddit, just post your question on the Scott Galloway subreddit, and we might feature it in an upcoming episode.

• 27:21Scott Galloway?

  This episode was produced by Jennifer Sanchez and Laura Janer. Kami Rika is our social producer. Brad Williams is our editor. Andrew Burrows is our technical director. Thank you for listening to the Prop G Pod from Prop G Media.