Investing in politically fraught opportunities

Paul Auslander, President of SeaBridge Private Wealth, a division of SeaBridge Investment Advisors LLC joins the Chuck Toddcast for a wide-ranging conversation about the intersection of money, markets, and the current political moment. Auslander walks through how the political climate now factors directly into financial planning projections, noting that European indices doubled the S&P's performance last year as capital flows shift overseas, and that a growing number of wealthy clients are hedging by moving money out of the United States. He offers candid takes on the issues keeping investors up at night: the inevitability of Social Security cuts (though he argues simply pushing retirement age from 67 to 69 would stabilize the fund), the likely future of Social Security privatization, crypto's evolution from a technological revolution into a special interest that bought its own policy outcomes, and whether there's money to be made off bad Trump policies that are likely to be reversed. Auslander also explains why the bond market is a better barometer of economic health than the stock market, why private equity is sitting on mountains of sidelined capital, and why he remains cautiously bullish on 2026 — largely because AI is only in the "second inning" and massive disruption is still ahead.

The conversation also ventures into territory financial planners don't usually discuss publicly. Auslander addresses whether the wealthy are worried the "pitchforks are coming for them," pointing to economic anxiety driving a spike in gun sales and a pop culture landscape that increasingly portrays corporations and the ultra-rich as villains. He breaks down the rise of family offices — private wealth management firms for the ultra-wealthy that take a long-term investment view — and explains why companies increasingly choose to stay private thanks to nearly unlimited private capital, rather than face the scrutiny of public markets. They also dig into the generational divide between investing and gambling, the casino-like nature of prediction markets, and the burden that post-Lehman Brothers insurance and regulatory requirements have placed on small businesses and regional banks that had nothing to do with the 2008 financial crisis. Auslander closes with a pointed message: that Fed independence and the rule of law are paramount to economic stability, and that centrism — not ideological extremism — remains the best way to run the country.

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Timeline:

(Timestamps may vary based on advertisements)

00:00 Paul Auslander joins the Chuck ToddCast

01:30 Paul’s origin story

02:45 Financial planning was mostly done by insurance companies in 70’s

03:30 Northerners move to FL for taxes & weather, but FL is pushing it socially

06:00 Fiduciary responsibility is the line of demarcation in financial planning

07:00 Factoring the political climate into financial planning projections

08:30 European index doubled the performance of the S&P last year

09:30 Tax policy is generally the biggest concern for investors

12:00 A cut to social security payments is bound to happen

13:00 If you push retirement from 67 to 69 the SS fund becomes healthy

15:15 Social security privatization likely to happen in the future

17:15 Money to be made off bad Trump policies that are likely to go away?

18:15 Crypto became a special interest & bought support for pro crypto policy

20:00 Crypto is a revolution that predates Trump & will outlast him

21:30 Lesson to be learned from rise then collapse in price of silver?

22:30 Central banks are buying silver, gold and assets

24:00 How many people are hedging by moving money out of the U.S.?

24:45 Europe is spending big money on arms & infrastructure

26:00 Definition of a “Family Office”

28:30 Family office investments are increasingly popular & take the long view

30:00 Are the investors/wealthy worried the pitchforks are coming for them?

31:30 Economic anxiety driving a spike in gun sales

33:00 Pop culture portrays corporations & wealthy as the villains

34:30 Private equity has a lot of money on the sideline, looking for investments

37:30 The burden of insurance requirements on small business

40:00 Small & regional banks paying for the sins of Lehman Brothers

41:00 Companies stay private due to near unlimited private capital 

41:45 Do young people like investing… or do they just like gambling?

42:45 Thoughts on prediction markets?

44:00 There’s a casino like approach to certain markets

45:15 If the house flips, you could see money get withdrawn from markets

46:30 How do Trump’s relationships with world leaders affect projections?

47:45 The bond market is more indicative of economic health than stock market

48:45 Uncertainty will impact earnings

49:15 Why are you feeling bullish on 2026?

51:30 AI is only in the 2nd inning. Disruption is coming

54:30 Thom Tillis sounds like a different man now that he’s retiring

55:30 Centrism seems like the best way to run the country

57:30 AI won’t be replacing financial advisors anytime soon

59:45 What’s one question you want every presidential candidate to answer?

1:00:15 Fed independence and rule of law are paramount

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