Pivot – "Personal Investment Strategies, Effective Public Policies and Should We Tax AI?"

Podcast: Pivot
Host: Kara Swisher & Scott Galloway (New York Magazine)
Date: December 19, 2025

Episode Overview

This end-of-year listener mailbag episode features Kara Swisher and Scott Galloway fielding bold, thought-provoking questions from their audience. The central themes: the implications of taxing AI, transformative public policies, and candid discussions about personal wealth, parenting after loss, and how the hosts actually live and invest. As ever, the discussion is rich with their trademark banter, irreverent honesty, and incisive insight.

Key Discussion Points & Insights

1. Should We Tax AI and Companies Using AI?

[01:56–05:18]

• Listener Question: As AI threatens jobs, should governments tax AI or the companies utilizing it to offset impacts on displaced workers—or is that just taxing the rich by another name?

• Kara Swisher references Bill Gates’ previous calls to tax robots as workers. She admits, “I hadn't really thought about it about AI,” inviting Scott’s policy-focused take.

• Scott Galloway argues against industry-specific taxation:

  “The moment you start taxing specific industries, you weaponize special interest groups to come to their defense. …Is Microsoft an AI company?”

  “I want to go back to Reagan era taxation. …I would like to see an elimination of the capital gains tax deduction and raise those rates to current income and restore a progressive tax structure…. I think taxes need to go up.”

  — Scott Galloway [02:55–03:55]

• He advocates for an across-the-board approach: boosting capital gains rates, instituting a federal Alternative Minimum Tax (AMT) for ultra-high earners, and focusing on closing loopholes rather than targeting AI or other sectors.

  “We focus too much on tax rates, not on the tax code. …There's no reason why someone working for money should be taxed at a higher rate than someone… making money from investments.” — Scott Galloway [04:40]

• Kara adds: “Gosh, Lynn, what a great question. …There's going to have to be some mitigation,” underscoring the need to rethink workplace taxation and support for displaced workers.

2. One Public Policy to Solve the Most Problems

[05:47–07:33]

• Question from Liam (High School Senior): If you could implement one policy to address America’s biggest structural problems, what would it be?

• Kara’s choice:

  “$25 minimum wage. …If people get paid more, they'll spend more. It creates a better economy…. It creates people that can do a living wage.” — Kara Swisher [06:12–06:22]

  • Runner-up: Rapid expansion of affordable housing.

• Scott’s answer:

  “If I could overturn Citizens United, I would. …A lot of our problems stem from the weaponization of Washington by corporate interest and corporate money.” — Scott Galloway [06:46–07:08]

  • Runners-up: Mandatory national service, universal child care, and gradually lowering Medicare age for near-universal coverage.

• Both hosts agree that meaningful, structural reforms—not “band-aid solutions”—are critical and deeply overdue.

3. Personal Money Philosophies and Investment Strategies

[11:24–18:53]

• Listener Eric: Asks about Kara and Scott’s spending/saving/investing habits.

Kara’s Approach:

• “I don't think about money a lot. That's my problem. I'm not interested in it. And I make a lot of money. …I save a lot. I have a lot of savings, and I diversify. I'm sort of your basic bitch of investing. I have bonds… quite a bit of real estate… a basket of stocks… very diversified. I have a lot of cash right now.… I have way too much cash compared to what I need. But I like to have it.” — Kara Swisher [11:39–13:12]
• Major spending: Children (education, savings), some travel, modest lifestyle. “I'm more frugal than Scott.”

Scott’s Approach:

• “One of my addictions is money.… I continue to be too focused on it to the detriment of my mental health. …I spend between three and four hundred thousand dollars a month. I own homes all over the world. I have a plane.…” — Scott Galloway [14:03–15:02]
• Ethos: “We don't own money, we rent it.” Anything saved above his “number” goes to philanthropy. “My net worth has not increased in eight years. …there's no reason anybody needs to be a billionaire.”
• Investment lens: “I bought homes in all of those places except for Dubai… pretend Jeff Bezos is going to buy this home because the world is going to produce thousands of billionaires over the next 20 years.”
• Notable honesty:

  “Money is something I think a lot about because I didn't have a lot of it growing up. It's still a very big issue in my life.” — Scott Galloway [18:06]

Notable Exchange:

• “You live well, not opulently is the way I would describe it.” — Scott to Kara [18:50]

4. Parenting After Loss: Advice and Reflections

[18:53–24:32]

• Lisa asks: As a widow, how do you keep a lost parent’s memory alive for kids? What did your own parents do right or wrong (Kara, after losing her father; Scott, raised by a single mother)?

Kara:

• “She [my mother] lost contact with my dad’s parents… She threw away a lot of pictures… I think she should have spent a lot more time talking about him… Make sure your kids know their relatives on your dad’s side and his friends.” — Kara Swisher [20:56–21:59]
• Kara names her son after her father and keeps his photos and letters visible.

Scott:

• Shares an emotional memory of his mother teaching him to drive and surprising him with a car, giving him confidence and affirmation.

  “If you tell your kids every day they have value, they start to believe you.” — Scott Galloway [22:59–23:03]

• Practical advice:

  “If you reverse engineer a young man’s problems to a single point of failure, it’s when he loses a male role model. ...especially important that you get men involved in your son’s life.” — Scott Galloway [23:13–24:10]

• “While boys are physically stronger, they’re emotionally and neurologically much weaker than girls.”

• Kara adds: “Let [kids] talk about [the lost parent] every day.… That’s critically important.”

5. If You Had All the Money in the World, What Would You Do—and Why Aren’t You Doing It?

[28:55–31:28]

• Paul asks: If you had unlimited money, what would you spend your time on now—and why not now?

• Scott:

  “I'm doing it. Money plays. I'm doing exactly what I want to be doing every day.” — Scott Galloway [29:17–29:51]

  • Would double down on restoring American values and getting Democrats elected.

• Kara:

  “I’d take a bunch of money and solidify a progressive—not like hateful to conservatives—but… values that are about fairness and equity.”
  “I’d do the Mackenzie Scott [the billionaire philanthropist]—just suddenly show up with money and not be heard from again. …I would also create universal daycare.” — Kara Swisher [30:06–31:25]

6. Behind-the-Scenes of the Pivot Live Tour

[31:39–34:40]

• Listener Brian: What happens backstage—any drama, wild parties?

• Kara:

  “No, we actually talk to each other....It's really quite civil. And then afterwards, we just go. We leave...Not tiring, but we just move on.” — Kara Swisher [32:19–33:03]

• Scott:

  “It was basically get up, get to the airport,…I would try and grab a workout… FaceTime my kids, and then start prepping for the show. …I drank less that seven days than I have in a long time. There was just no room for partying or alcohol.” — Scott Galloway [33:03–33:45]

• Both recount favorite moments (DC, LA) and the emotional, bonding nature of touring together.

7. Tattoo Suggestions—A Pivot Tradition

[37:05–39:39]

• Kara reads out fan-submitted tattoo ideas themed around Scott—including:

  • “A roll of toilet paper with an S”
  • “Penis with his name embedded (‘SC’ on one cheek, ‘TT’ on another, ‘O’ as the asshole)”
  • “A barcode that, when scanned, says ‘the problem with Scott is…’”

• Scott suggests:

  “Just in case of emergency call Scott.”
  “A fortune cookie. And the fortune reads you will tolerate someone named Scott today.”
  “A tombstone that says rest in peace. Scott’s sanity taken by Kara.”

• This sign-off segment lets their famously spiky rapport shine.

Notable Quotes & Memorable Moments

• On Progressive Taxation:
  “There's no reason why someone working for money should be taxed at a higher rate than someone… making money from investments.”
  — Scott Galloway [04:40]

• On Parenting After Loss:
  “If you tell your kids every day they have value, they start to believe you.”
  — Scott Galloway [23:03]

• On Living Well:
  “You live well, not opulently is the way I would describe it.”
  — Scott Galloway to Kara Swisher [18:50]

• On Spending Wealth:
  “We don’t own money, we rent it. …Hoarding money is a virus.”
  — Scott Galloway [14:03–16:04]

• On Having Enough:
  “I don't also—let me point out, my mom was a spendthrift, and it upset me… I was like, I'm always gonna have enough money.”
  — Kara Swisher [18:53]

Timestamps for Major Segments

• [01:56] — Taxing AI and the future of work
• [05:47] — The one public policy fix (minimum wage, Citizens United)
• [11:24] — Discussing personal finance, saving, investing
• [18:53] — Advice for parenting after loss
• [28:55] — The “all the money in the world” question
• [31:39] — Behind-the-scenes of the Pivot tour
• [37:05] — Listener tattoo suggestions—lighthearted sign-off

Tone & Dynamic

Swisher and Galloway’s exchanges are witty, frank, and brimming with the “bicker and banter” that makes Pivot distinct. They move from serious analysis to self-deprecating humor and deeply personal reflection—retaining sharp insight without ever losing their conversational edge.

This listener-driven episode exemplifies the best of Pivot: sharp analysis, bold opinions, and genuine candor—whether talking about billionaires, healthcare, or the tattoos they’d (maybe) get for each other.