Podcast Summary

The Investor With Joel Palathinkal

Guest: Wen Shiau (Founder and Managing Partner, Cypress Capital Group)
Date: September 11, 2025

Overview

This episode features Wen Shiau, founder of Cypress Capital Group—a single family office focused on real estate, macro trading, and software-centric venture investing (non-crypto). Wen brings a wealth of experience, having started in institutional fixed income, overseeing Asia-Pacific trading at major investment banks, and now leading private equity real estate funds targeting US tech-centric cities. The conversation delves into asset allocation for family offices, global and US market selection, constructing resilient real estate portfolios, approaches to venture investing, the role of AI, and philosophies on generating excess returns.

Key Discussion Points and Insights

Wen Shiau’s Background and Family Influences (02:41)

• Wen traces his roots to New Jersey, attended Cornell (math and computer science), and began his career at Bell Labs (speech synthesis/R&D).
  • “Back in the dinosaur age I was a theoretical AI major within computer science. And we certainly didn't have the compute power to do what we do now.” (02:57, Wen)
• Career pivoted to Wall Street as a mortgage-backed securities trader at First Boston (later Credit Suisse) with a global stint (New York, Hong Kong, Tokyo), co-heading Asia-Pacific sales and trading.
• In 2006, transitioned to full-time investing in Northern California for proximity to technology and Asia, launching his family office and real estate private equity funds.

Defining “Good” Investing and Portfolio Construction (07:03)

• Multi-Asset Strategy: Joel prompts: how do you determine if a multi-asset family office portfolio is “good” when blending public/private investments?
• Sharpe Ratio as Anchor: Wen stresses using Sharpe ratio (risk-adjusted returns) across all asset classes, including real estate—not just public markets.
  • “What you want is the highest absolute return with the lowest volatility… the best measurement we have is the Sharpe ratio.” (08:55, Wen)
• Diversification and Conviction: One plus one should yield three; deploying capital only where the “why” behind each asset, geography, and currency is validated through top-down analysis.

Real Estate: Allocation, Geography, and Asset Classes (09:57 & 13:08)

• Global vs. US Focus: Wen once believed Asia, especially China, would outperform, but data (The Economist) shows US equities (S&P 500) outperformed globally over the last 40 years.
  • “Over the last 40 years the US was number 1...even beat the Hang Seng Index...crushed Europe…” (15:07, Wen)
• Competitive Moats: US dominance attributed to rule of law, openness to immigrants, and vibrant tech ecosystems.
  • “It isn't just America and Americans, it's our system that is exceptional and that has allowed capital to grow.” (16:06, Wen)
• Within the US: Wen advocates for investing in economic centers where new wealth is being created (not just where it exists), e.g., Silicon Valley and New York.
  • “Dirt goes up in value when the wealth is being created, new wealth is created. Not where rich people are.” (18:05, Wen)
• Strong-get-stronger Thesis: Despite narratives about migration, 65% of VC dollars are now concentrated in NY and Silicon Valley, up from 40% in 2000.
  • “These economic centers do not weaken. They get stronger. And it’s called an ecosystem.” (20:15, Wen)

Practical Real Estate Criteria & Downside Protection (21:20 & 28:54)

• Repeatability and Specialization: Wen distinguishes between one-off wins and scalable, sustainable investments—advocating for deep focus in key markets, not scattershot investing.
  • “Can you do 100 more of those in that location? That’s the difference between a one-off and investment management.” (22:01, Wen)
• Market Liquidity and Safety: Neighborhoods must have depth/breadth—easy entry/exit, safety, and middle-class vibrancy.
  • “When you are seeing joggers in the morning, when you’re seeing baby strollers...that’s investable.” (32:15, Wen)
• Affordable Luxury Segment: Focus on properties in the top 5–10% of the buyer pool, not ultra-high-end or distressed sectors.
• Co-ops: Deemed “uninvestable” for lack of true ownership and liquidity. (30:39, Joel/Wen)
• Downside Risk: Even in shocks (e.g., 2007-10), tier-one markets like Palo Alto saw ~20% drops vs. 70% in Vegas.

Public Policy, Supply Constraints & Opportunity (35:10 & 37:15)

• Regulation as Moat: Markets where it’s hard to add supply (e.g., NY, CA) deliver excess returns—not because of incentives, but due to persistent undersupply.
  • “Where it is hard to provide supply is exactly where I’m going to get paid an excess return.” (38:23, Wen)
• Public-Private Partnership: Wen calls for realistic policies partnering with credible developers to boost tax base and neighborhood quality.
• Contrasts with Austin, TX: Easy permit/supply led to 25–30% price declines in 2025; by contrast, constrained markets keep prices high.

Approaches to Venture Capital & Software Investing (43:24)

• When Returns Occur: Most value in tech is realized after companies go public; risk-adjusted returns for early-stage venture are often poor.
  • “...most of the value of these companies are created after they go public...the risk adjusted returns for venture is actually not very good.” (44:14, Wen referencing Freeberg)
• Why Invest in Venture? Wen values the insight into technology trends more than outsized returns.
  • “I invest in venture because I want an edge in insights into the technology...that insight helps me with my public market investments.” (46:06, Wen)
• Direct vs. Fund: Specialists with edge/unique perspective are preferred; repeatability and depth in funds or direct investments matter.
• Software Stickiness: Preference for B2B SaaS where the platform is deeply embedded, has user data, and switching costs are high.
  • “If you own the software and you own their data, you got a captive audience. Look at Microsoft...with the software and the data you will have.” (48:19, Wen)
• Traits of Stickiness: Data centralization, complexity of migration, integrated analytics—example: Bloomberg Terminal, Stripe, Palantir.

The Transformational Role of AI (51:23 & 52:37)

• AI Dominance: AI is a winner-takes-all space; every hyperscaler is “all in.”
  • “AI...it’s an all in thing. Either you own it and you’re the winner. And the winner takes all...There’s one Facebook, there’s one Google search…” (52:39, Wen)
• It’s a Never-Ending Race: “The only thing that matters is does China or the US win the AI race? And like Jensen Wong said, this race…doesn't have a finish line.” (53:44, Wen)
• Finding Bottlenecks: Current focus: where in the AI stack is the bottleneck—energy/cooling for data centers, etc.

New York and Silicon Valley: Enduring Global Capitals (55:25)

• Bi-Coastal Dominance: Continued concentration—New York as the sole financial capital, both cities dominating tech and capital flows.
  • “There is no way. The only financial capital in the world of New York is not a place you would want to avoid.” (55:25, Wen)

Notable Quotes & Memorable Moments

• On Being a Contrarian:

  “If you want to generate excess returns, and we all do, you must be a contrarian because you cannot follow the herd...But you must be right. Because sometimes the crowd is right and you are contrarian and you happen to be wrong.”
  — Wen Shiau (57:07)

• On Sharpe Ratio:

  “What you want is the highest absolute return with the lowest volatility...what asset class gives you the highest Sharpe ratio?”
  — Wen Shiau (08:55)

• On Choosing US Markets:

  “The US was number 1...even beat the Hang Seng Index...crushed Europe at the end...”
  — Wen Shiau (15:07) “It’s not just America and Americans, it’s our system that is exceptional.”
  — Wen Shiau (16:06)

• On Real Estate Repeatability:

  “The thing that you want to do as an investor is, is it repeatable? ...Can you do 100 more of those in that location? That’s the difference between a one-off...versus I can repeat this.”
  — Wen Shiau (22:01)

• On Stickiness of Software:

  “If you own the software and you own their data, you got a captive audience. ...With the software and the data you will have.”
  — Wen Shiau (48:19)

• On AI’s Central Role:

  “AI...it’s an all in thing. Either you own it and you’re the winner. And the winner takes all.”
  — Wen Shiau (52:39)

• On Risk Sizing & Federer's Lesson:

  “You’re only going to win 55% on average of all your investments. So how do you turn a 55% slightly winning percentage into a huge win...When it’s a high conviction trade, don’t put a dollar into it, put a hundred dollars into it.”
  — Wen Shiau (59:30)

Timestamps for Important Segments

• Wen’s Early Life/Career: 02:41–06:50
• Portfolio Theory & Sharpe Ratio: 07:03–09:56
• Top-Down Real Estate Analysis: 09:57–13:08
• US Market Outperformance: 13:08–16:32
• Why Tech Hubs Get Stronger: 19:09–20:15
• Repeatability in Real Estate: 21:20–23:25
• Downside Risk Management: 24:11–25:48
• Investing in Neighborhoods: 28:54–34:10
• Impact of Policy on Supply: 35:09–39:51
• Venture vs. Public Market Value Creation: 43:24–44:42
• Value of Tech Insight from Venture: 46:06–47:14
• Software Stickiness: 48:19–49:27
• AI’s Market Dynamics: 52:37–54:03
• Advice for Investors—Contrarianism & Sizing: 57:07–59:35

Key Takeaways

• Sharpe Ratio applies across all asset classes, even alternatives like real estate.
• Concentrate where new wealth is being created, focus on repeatable, scalable strategies.
• Deep market knowledge, specialization, and contrarian views—when correct—drive excess returns.
• AI and software remain central to future wealth creation; seek bottlenecks and sustainable moats.
• Market depth, supply limits, and neighborhood vibrancy are crucial real estate factors.
• New York and Silicon Valley’s dominance is intensifying, not receding, despite popular narratives.

For further details on topics, refer to timestamps. This summary is designed to capture essential themes, expert insights, and actionable advice for investors or allocators who missed the episode.