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Scott Galloway
Scott Galloway
Founder; Host of The Prof G Pod; Co-host of Pivot and Prof G Markets, Prof G Media
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Should You Sell Your Stocks Right Now? | Office Hours

📅 Aug 03, 2026 The Prof G Pod – Scott Galloway 22 MIN 160661 VIEWS 11 SEGMENTS · 3 SPEAKERS
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: https://bit.ly/4eDuJ2y. Plus, you can now call or text Scott a question at our new Office Hours hotline: ‪(201) 472-3656‬. Timestamps: 00:00 - In This Episode 00:33 - When to Sell Your Stocks 08:11 - How to Handle a High-Pressure Job 15:57 - Best...

What Scott Galloway said

Written from the verified transcript and checked against it. Every figure links to the moment it was said.

Scott Galloway advised Jim from Connecticut against selling his diversified $3 million stock portfolio to time the market, arguing that while markets are 'wildly overvalued,' timing is nearly impossible and investors should stay invested. He recommended holding stocks for at least 12 months for long-term capital gains, borrowing against them for cash needs (up to 20-40% max), and using the 'buy, borrow, die' strategy for tax efficiency. Galloway noted his own portfolio is about 20% in stocks, preferring private assets to avoid daily mark-to-market stress. For Matio starting in investment banking, Galloway shared his Morgan Stanley experience, advising to 'action absorbs anxiety,' read up on the industry, show up early, leave late, and embrace the intense work culture as a launch trajectory. For a cancer survivor caring for elderly aunts, he recommended not becoming a full-time caregiver, establishing boundaries, and involving other family members to maintain one's own life and career.

Key takeaways

  1. Galloway advises against selling a diversified portfolio to time the market, even when markets are 'wildly overvalued,' because timing is nearly impossible.
  2. He recommends holding stocks for at least 12 months to qualify for long-term capital gains and using margin loans (up to 20-40% of portfolio) for cash needs.
  3. For investment banking, he advises showing up 10 minutes early, leaving 10 minutes late, and reading up on the industry to control anxiety.

Numbers and commitments

FigureWhat it refers toTypeAt
20% Galloway's net worth in stocks metric 0:00
$3 million Jim's stock portfolio value metric 0:32
$1 million Jim's cost basis in stocks metric 0:32
20% Combined state and federal capital gains tax rate metric 0:32
25% Jim's stocks as percentage of net worth metric 1:21
12 months Holding period for long-term capital gains timeline 1:21
20-40% Maximum margin loan against stocks guidance 1:21
2.27 Galloway's UCLA GPA metric 8:32
9:00 a.m. to 5:00 p.m. Wednesday Galloway's Tuesday-to-Wednesday work hours at Morgan Stanley timeline 8:32
8-9 months Time Galloway lived with his mother before her death timeline 8:32

Chapters

  1. 0:00Selling stocks and tax consequences
  2. 1:21Market timing and diversification advice
  3. 8:10Investment banking career advice
  4. 15:51Caring for aging relatives

Questions asked in this interview

1
  1. 0:32If my gut is telling me to get out, should I bite the bullet and pay the 20% exit fee and the gains?
Scott Galloway 0:00 ↗
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. The way your Kevlar when the markets go down is diversification.
Today we talk about when to sell your stocks, how to handle a high-pressure job, and the best way to care for an aging loved one. Question number one.
Jim 0:32 ↗
Hi Scott, it's Jim from Connecticut. My question is, how much do you consider tax consequences when you are 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. 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. 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 and the gains?

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Cite this transcript

APA, MLA, BibTeX
APA

Galloway, S. (2026, August 3). Should You Sell Your Stocks Right Now? | Office Hours [Interview transcript]. The Prof G Pod – Scott Galloway. CEOInterviews.AI. https://ceointerviews.ai/interview/3002815/

MLA

Scott Galloway. "Should You Sell Your Stocks Right Now? | Office Hours." The Prof G Pod – Scott Galloway, 3 Aug. 2026. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/3002815/.

BibTeX 
@misc{galloway2026_3002815,
  author       = {Scott Galloway},
  title        = {Should You Sell Your Stocks Right Now? | Office Hours},
  howpublished = {Interview transcript, The Prof G Pod – Scott Galloway. CEOInterviews.AI},
  year         = {2026},
  month        = {aug},
  url          = {https://ceointerviews.ai/interview/3002815/},
  note         = {Speaker-attributed transcript with timestamps}
}