Podcast Summary: The Prof G Pod with Scott Galloway — Office Hours Episode: How to Think About Stock Options, Healthcare Without Insurance, and Handling Rejection
Date: December 15, 2025
Host: Scott Galloway (Vox Media Podcast Network)

Episode Overview

In this edition of the ProG Pod’s "Office Hours," Scott Galloway answers listener questions centered on business and life decisions: how to evaluate and negotiate stock options as part of a compensation package, the reasoning and practicalities behind paying for healthcare out-of-pocket instead of using insurance, and strategies for handling failure and rejection. The episode blends financial practicality, blunt critiques of American institutions, and personal storytelling, delivered in Scott’s signature irreverent and motivational style.

Segment 1: How to Think About Stock Options

Listener Question (02:06):
A college senior with multiple job offers (including one from an aerospace startup offering incentive stock options — ISOs) seeks advice on how to value and approach equity compensation as an early career professional.

Key Discussion Points and Insights

• Current Income vs. Equity Wealth

  • Young professionals typically spend almost all salary:

    "Generally speaking, 90 to 98% of us will spend everything that comes through our hands, especially as a young person." (03:05)

  • Equity is the path to real wealth:

    "Equity is how you get wealthy." (05:01)

• What Are ISOs?

  • Stock options grant you the right to buy company shares at a set price in the future.
  • ISOs are not taxable when granted, only when exercised or sold.
  • If the company grows and exits at a higher valuation, exercised options can become a lucrative form of compensation.
  • Stock options usually vest over time (commonly four years).

• Valuation and Negotiation

  • Use AI or Google to figure out real-time value of your options:

    "Go to AI and type in the name of the company, the evaluation of the last funding round, how many options you've been given on how many shares at what strike price..." (05:47)

  • Consider negotiating not for more salary but for a larger option grant:

    "Employers are really receptive to the notion that 'I don't want more current income, I want more options because I want to be an owner here.'" (07:12)

  • Option growth is tax-deferred, unlike salary which is taxed immediately, allowing for better compounding.

• Final Advice for Young Professionals

  • Do your own research, value your options against your salary, and negotiate.
  • Transparency is a strong negotiating tactic:

    "'Love the company, want to start here. Can you see your way clear to increasing my options package as I want to be an owner, I really believe in this company.'" (07:04)

• Memorable Mentoring Moment

  "This is the mother of all good opportunities. You should feel really good about yourself... Everybody wants to be you young man. So congratulations and well done." (08:02)

Segment 2: Healthcare Without Insurance

Listener Question (09:05):
A listener asks about Scott’s choice to pay out-of-pocket for medical expenses rather than carry traditional health insurance and how that works in practice.

Key Discussion Points and Insights

• System Critique

  • The US system is centered on profit, not health:

    "Healthcare isn't about making Americans healthier. It's about making the owners of the stock of that healthcare company wealthier." (09:19)

  • Insurance is described as "one of the biggest scams in history" because of its administrative overhead and profit extraction.

    "For every hundred dollars you give to insurance...45% goes to profits and administration. Meaning...you're gonna get about $55 back in reimbursements." (10:18)

• On Going Without Insurance

  • Scott’s perspective is informed by financial privilege:

    "I'm in a position to do this because I'm bulletproof. What do I mean by that? Anything could happen to me from a health perspective, and I can afford it." (11:31)

  • For the already wealthy, skipping insurance may make sense due to systemic inefficiencies and persistent out-of-pocket costs even when insured.

• Personal Experience

  • "Concierge medicine": paying $60,000/year for elite service (on-call doctor, at-home meds, comprehensive scans):

    "If I text my doctor, he texts me back within two minutes; I am getting an absolutely different level of care." (12:04)

  • Even with traditional insurance, Scott found he was paying large premiums and still fighting with insurers.

• Ethical and Policy Perspective

  • Healthcare should be a right; the cost-benefit in America is poor:

    "We pay more for a shittier product. Unless, again, see above, you're in the top 10%." (12:41)

  • Advocates for lowering Medicare eligibility and socializing more of medicine:

    "All roads around economic responsibility and deficit reduction lead to one place, and that is reduction and attacking the healthcare industrial complex." (12:55) "If people want to call me a communist or socialist, fine, fine. Yeah, those nations...it doesn't mean you're also going to go bankrupt." (13:09)

• Broader Social Commentary

  • The system strips dignity:

    "Too many Americans are having their dignity taken from them because of the monetization of our healthcare system." (13:28)

Segment 3: Handling Rejection and Failure

Listener Question (16:56):
A Reddit user asks for tangible steps to mourn rejection and recover, referencing Scott's oft-repeated advice: "mourn and get back up."

Key Discussion Points and Insights

• Enduring Rejection as a Skill

  • Perseverance through rejection is central to success:

    "The only thing that people you admire, unless they were smart enough to be born rich, have in common is they've endured a shit ton of no's to get to great yeses." (17:40)

  • Scott details his own experiences:
    • Rejected from 8/9 business schools, "pitched 300, got 294 no’s" when fundraising.

• Ways to Mourn and Move On

  • Accept and normalize rejection:

    "Get used to them. A lot of approaches, send a lot of emails, try and get a lot of meetings, ask a lot, and when you get the no, realize you're gonna be fine." (18:20)

  • Give yourself a "statute of limitations" for mourning (e.g., a week after job loss, then get back in the game).
  • Talking about grief openly is therapeutic; action helps counteract anxiety:

    "What helped me was talking about it. I didn't do therapy, but I talked to a lot of people about grief and I became very open about it and that helped." (19:32) "I love the notion of action absorbs anxiety." (20:37)

• Practical Tips

  • If stuck, seek help (therapy, social connection).
  • Apply for jobs, network aggressively:

    "Every day you're sending out emails and updating your CV and trying to get coffees with people...you'll feel better about yourself." (20:46)

  • Social connections are crucial for landing jobs:

    "70% of the time the person who ultimately gets the offer is someone who has an internal advocate. So being social is really, really important." (21:17)

• Personal Reflection

  • After his mother's death, Galloway was himself paralyzed with grief for years, ultimately overcoming it through openness and action.
  • Galloway emphasizes he is not a therapist; this advice is from personal experience.

• Memorable Quotes

  "If you never develop calluses, you can't lift heavy weights." (18:58)
  "I've probably pitched...300. I think I've gotten 294 no's." (17:57)
  "Be aggressive, get off your heels and onto your toes." (21:29)

Notable Quotes

• "Equity is how you get wealthy." — Scott Galloway (05:01)
• "Health insurance, just keep in mind, you're getting 55 cents on the dollar." — Scott Galloway (11:55)
• "Too many Americans are having their dignity taken from them because of the monetization of our healthcare system." — Scott Galloway (13:28)
• "If you never develop calluses, you can't lift heavy weights." — Scott Galloway (18:58)
• "Action absorbs anxiety." — Scott Galloway (20:37)
• "Be aggressive, get off your heels and onto your toes." — Scott Galloway (21:29)

Timestamps for Key Segments

• 02:06 — Stock Options: How to Value, Negotiate, and Leverage Equity Offers
• 09:05 — Healthcare Without Insurance: Costs, Privilege, Systemic Critique
• 16:56 — Handling Rejection: Strategies to Mourn, Recover, and Move Forward
• 05:01, 07:12, 13:28, 18:58, 20:37, 21:29 — Most Memorable Quotes

In Scott’s Tone: Direct, Blunt, Encouraging

Scott’s responses fuse business savvy with emotional intelligence, using humor, tough love, and clear examples. He frequently references the realities of capitalism, privilege, and systemic inefficiency, while centering individual agency and resourcefulness.

For more listener questions or to submit your own, reach out to Office Hours at officehours@profgmedia.com or post on the Scott Galloway subreddit.