In this episode of Excess Returns, we welcome back Tobias Carlisle — author, host of Value After Hours, and manager of the Acquirers Funds. Toby shares his candid perspective on market valuations, value investing’s long struggle, and why he still believes mean reversion will eventually swing back in favor of small caps and value stocks. We also dive into AI, global markets, the Fed, housing, and where investors might find opportunity outside today’s expensive U.S. mega-caps.

• Market valuations: why today’s market may be more expensive than 1929, 2000, or 2020

• The pitfalls of relying on single-year P/E ratios and better long-term valuation measures

• The divergence between the “Magnificent 10” and the rest of the market

• Small caps, mid caps, and value: where Toby sees opportunity despite an earnings recession

• AI as both a transformative force and a potential bubble-like capital cycle

• U.S. vs. international markets: structural advantages of American capitalism and where China is catching up

• The Fed, interest rates, inflation, and how they really matter for value investors

• Housing affordability and demographics as headwinds for the U.S. economy

• Why Toby believes the “value vs. growth jaws” will eventually close

00:00 – Are markets more expensive than 1929 and 2000?
04:00 – Breaking down valuation charts: S&P, Russell, and mid/small caps
10:00 – Why single-year P/Es mislead investors
14:00 – Lessons from past bubbles: Nifty 50, dot-com era, and now
19:00 – Large vs. small: the longest run for growth in history
24:00 – AI’s impact: transformative technology or capital cycle trap?
32:00 – Toby’s personal experience with AI (and why it disappoints him so far)
33:00 – U.S. advantages vs. international markets and China’s rise
41:00 – Are today’s U.S. valuations justified?
45:00 – The Fed, interest rates, and speculation
46:00 – Housing affordability and demographics as headwinds
55:00 – Should value investors care about macro?
59:00 – Closing question: Toby’s contrarian belief on value vs. growth

In this episode, we sit down with Leigh Drogen of StarKiller Capital, alongside guest co-host Kai Wu, for a deep dive into crypto investing strategies, momentum in digital assets, and market-neutral DeFi yield opportunities. Leigh shares his perspective on where we are in the crypto evolution, the parallels with past technology cycles, and how to survive and advance in one of the most volatile asset classes in the world. From time-series and cross-sectional momentum to the economics of yield farming, this is a comprehensive look at building systematic strategies in digital assets.

Topics Covered:

• The parallels between Web1 → Web2 and today’s crypto transition

• Why the “fat protocol” thesis is giving way to the “fat app” era

• The role of Bitcoin vs. Ethereum in the next stage of crypto adoption

• The “survive and advance” investing philosophy

• Time-series momentum and cross-sectional momentum in crypto

• How VC behavior is changing momentum dynamics

• Sector-level momentum and narrowing lookback periods

• StarKiller’s approach to asset selection and quality screens

• Building a market-neutral DeFi yield strategy

• Bootstrapping network effects and early liquidity provisioning

• Diligence, counterparty risk, and managing protocol risk

• The competitive landscape and where the biggest edges remain in crypto

Timestamps:
00:00 – Crypto’s infrastructure milestones and evolution
02:53 – The “fat protocol” vs. “fat app” thesis
08:09 – Bitcoin’s role vs. Ethereum’s potential
14:20 – “Survive and advance” and limiting drawdowns
19:20 – Time-series vs. cross-sectional momentum
23:00 – VC selling behavior and regime change in momentum
31:47 – Sector-level momentum trends
36:13 – Shorter lookback periods and market speed
39:56 – StarKiller’s investable universe and filtering process
48:00 – Designing a market-neutral DeFi yield strategy
52:56 – Rewards farming and bootstrapping network effects
58:00 – Market-making vaults and APR opportunities
01:00:10 – Managing counterparty and protocol risk
01:04:02 – Has crypto alpha become more competitive?
01:07:41 – One lesson for the average investor

How Aswath Damodaran Manages His Own Portfolio | Show Us Your Portfolio

In this episode of our Show Us Your Portfolio series, we go inside the personal investing approach of Aswath Damodaran — the “Dean of Valuation.” Known for his expertise in corporate valuation, Aswath rarely discusses how he manages his own money. We cover his philosophy, asset allocation, position sizing rules, lifecycle diversification, and the lessons he’s learned from decades of investing his own wealth.

What you’ll learn in this episode:

• The core mission that drives Aswath’s investing decisions

• How he thinks about risk, concentration, and position sizing

• Why he avoids bonds and focuses on equity appreciation

• His approach to strategic vs. tactical investing

• The role of lifecycle diversification in portfolio construction

• How he decides when to buy and sell individual stocks

• Why luck plays such a big role in investing results

• His views on international exposure, dividends, gold, crypto, and alternative assets

• Personal spending habits and what he values most outside of investing

Timestamps:
00:00 – Investing’s end game: preserve and grow wealth
03:25 – How life stage changes investment approach
07:41 – Thoughts on the 60/40 portfolio
08:47 – Why he holds no bonds
10:12 – The power of compounding
12:25 – Separating portfolio from income needs
15:02 – Strategic vs. tactical investing
18:00 – Managing concentration risk and trimming winners
20:30 – Market concentration & the Mag 7
25:31 – How he buys and sells stocks
32:46 – Hit rate and lessons from decades of investing
37:26 – Lifecycle diversification
41:00 – U.S. vs. international investing
43:22 – Dividend investing
45:35 – Gold, crypto, and alternative assets
53:15 – What he drives and his ESG take
54:39 – Spending for joy
56:00 – Key investing advice for individuals
57:37 – Life outside markets & creative thinking time