Daniel Crosby explains why investors can lose money in winning funds and how to build a portfolio they can actually hold. Picking the right investment is only part of the challenge; staying with it through discomfort is where behavior can overwhelm the plan.

In this episode of Excess Returns, psychologist and Orion Chief Behavioral Officer Daniel Crosby joins Matt Zeigler to discuss the new paperback edition of The Behavioral Investor. Daniel shares the story of a fund that returned over 18% annually for a decade while its average investor lost money, then explains how safety, stability, and success portfolios can help align investment decisions with human psychology. They also explore gambling apps, the limits of risk questionnaires, social media feedback loops, and the human side of financial advice in an AI-driven world.

Topics covered:

- Why a fund's returns can look very different from the returns its investors earn

- Building safety, stability, and success buckets around different financial needs

- The differences between risk tolerance, risk capacity, and risk composure

- Why knowing what to do does not guarantee doing it during a drawdown

- Daniel Crosby's case for rules, diversification, and meaningful benchmark differences

- How sports betting and prediction markets blur the distinction between investing and gambling

- Why recent market experience can create unrealistic expectations about future returns

- Education, environment, and encouragement as tools for changing investor behavior

- How algorithms reinforce market biases and why excitement can signal a blind spot

- Where AI can free financial advisors to spend more time on human relationships

The Behavioral Investor - paperback edition:https://link.amazon/B00hgkHGG

Daniel Crosby on X:

https://x.com/danielcrosby

Orion Behavioral Finance:

https://orion.com/behavioral-finance

Research discussed:

The heat of the moment: the effect of sexual arousal on sexual decision making

https://onlinelibrary.wiley.com/doi/abs/10.1002/bdm.501

Chapters:

00:00 Daniel Crosby and The Behavioral Investor

04:51 Why winning funds can have losing investors

11:46 Risk tolerance, capacity, and composure

17:38 Stability portfolios and rules-based stock selection

23:06 Investing, gambling, and prediction markets

27:27 Recency bias and unrealistic return expectations

31:30 Addictive apps and changing investor behavior

35:48 Investor distractions and the media diet

40:51 Investment excitement, humility, and AI

45:00 What music reveals about consistency and experimentation

49:29 Where to find Daniel Crosby and the book

Learn more about the Excess Returns podcast network:

https://excessreturns.co

No information discussed in this podcast should be construed as investment advice. Securities discussed may be held by the hosts and guests, their firms or their clients.

Ted Mortonson of Baird explains why conviction in the AI boom doesn't mean buying every dip in tech stocks.

He joins Jack Forehand and Justin Carbonneau to explain what experienced technology investors watch before putting money back to work—and why he still sees AI as the most powerful technology cycle of his career.

The discussion moves from lessons of the dot-com bust to the companies Ted believes can capture AI's profits. They explore the importance of free cash flow, the financing demands of the data center buildout, and how large IPOs could force portfolio managers to sell existing holdings. Ted also shares his views on Apple, Meta, Nvidia, Tesla, and SpaceX, before closing with lessons from his service as a naval aviator.

Topics covered:

- Why Ted Mortonson's institutional clients aren't rushing to buy the semiconductor dip

- What past tech cycles teach about taking profits, preserving capital, and waiting for selling to settle

- Why Ted Mortonson sees a stronger long-term AI opportunity than the dot-com cycle

- How geopolitics, energy costs, regulation, and investor sentiment shape technology investing

- Why free cash flow, engineering resources, and manufacturing scale matter for AI beneficiaries

- Financing the infrastructure buildout before enterprise adoption delivers returns

- How large IPOs and circular financing can create risks for existing shareholders

- Ted Mortonson's concerns about Apple and his outlook for Meta, Tesla, and SpaceX

- Optical networking, advanced chip architectures, and high-bandwidth memory

- Navy lessons on decisions under uncertainty, teamwork, and integrity

Chapters:

00:00 Ted Mortonson on the risks facing tech investors

05:42 Market sentiment and why his clients aren't buying yet

12:00 Dot-com lessons and the danger of buying every dip

16:17 Why Ted sees a different AI cycle

23:06 Which companies could capture AI's profits?

27:38 Regulation and financing the AI buildout

35:10 Can the market absorb massive AI IPOs?

39:30 Circular financing and the Tesla-SpaceX thesis

46:06 Apple, Meta, and competing AI strategies

54:19 SpaceX, advanced chips, and memory technology

58:26 Lessons from serving as a naval aviator

01:03:35 Closing thoughts

Ted Mortonson at Baird:

https://www.rwbaird.com/corporations-and-institutions/institutional-equities-research/team/ted-mortonson/

Learn more about the Excess Returns podcast network:

https://excessreturns.co

No information discussed in this podcast should be construed as investment advice. Securities discussed may be held by the hosts and guests, their firms or their clients.

Brian Portnoy of Shaping Wealth explores why experienced investors build very different portfolios—and what that means for your own money.

In How I Invest My Money Volume Two, 25 new contributors explain how they invest their personal wealth. Brian joins Matt Zeigler to discuss what those stories reveal about the gap between an optimal portfolio on paper and one you can actually live with.

From large cash reserves and paid-off mortgages to investments in their own businesses, their choices reflect family needs, career risk, and priorities that a model can struggle to capture.

The conversation also explores why low-cost index funds don't settle every investing question, how financial professionals think about bonds and alternatives, and what it means to compound relationships, knowledge, and opportunities alongside money.

How I Invest My Money Volume Two:
https://link.amazon/B0aVpNlfS

Topics covered:

• Why knowing how markets work doesn't produce one right portfolio for everyone
• What Ben Hunt and other contributors reveal about investing beyond a brokerage account
• Connecting personal goals to asset allocation and risk tolerance
• Why business ownership and household needs change the role of stocks and bonds
• Why financial professionals may deliberately hold substantial cash reserves
• The difference between spreadsheet optimization and a portfolio you can stick with
• Paying off a mortgage, feeling secure, and accepting the opportunity cost
• The complexity and illiquidity that can come with alternative investments
• Matt Zeigler's approach to compounding human, intellectual, social, and financial capital
• Brian Portnoy's experience editing the book with his son Zach and sharing opportunities across generations

Chapters:

00:00 How finance professionals invest their own money
05:35 Why investing extends beyond index funds
12:20 Connecting financial goals to portfolio choices
18:32 Why investors choose different stock and bond allocations
25:05 Cash reserves, career risk, and peace of mind
34:55 Paying off a mortgage: security versus opportunity cost
40:11 Alternatives, complexity, and the investment industry
44:40 Matt Zeigler on investing in more than money
52:22 Brian Portnoy on family, opportunity, and working with his son

Shaping Wealth:
https://www.shapingwealth.com

Follow Brian Portnoy on X:
https://x.com/bportnoy_

Learn more about the Excess Returns podcast network:
https://excessreturns.co

No information discussed in this podcast should be construed as investment advice. Securities discussed may be held by the hosts and guests, their firms or their clients.