What if the biggest edge in portfolio construction isn’t picking better assets but structuring a portfolio you can actually stick with through cycles? In this episode, I sit down with Chaya Slain, President and CIO at Virtera Partners LLC, to unpack how families can access institutional-quality investing without building a full family office. Chaya explains why alternatives are often the true driver of outperformance, how trend following can reshape risk and return, and why behavioral discipline matters more than perfect asset selection.

Disclaimer: The information discussed in this podcast is for informational and educational purposes only and should not be considered investment advice or a recommendation or offer to buy or sell any security. Nothing discussed in this podcast should be construed as creating an advisory relationship with any listener.

Highlights:

• Why building a traditional family office is inefficient below $100M to $1B in assets
• The real challenge in alternatives is access, diligence, and fee structure, not just sourcing
• How FOMO drives overexposure to “hot” private deals without understanding price
• Trend following explained simply and why it thrives during market dislocations
• Historical performance: how combining trend and equities improves returns and reduces drawdowns
• Why bonds may fail as protection and what can replace them in modern portfolios
• Behavioral investing: why structure and discipline outperform individual decision-making
• Lower middle market private equity: less competition, better entry prices, and multiple expansion potential
• Venture capital challenges: access, long time horizons, and wide dispersion of returns
• How misaligned incentives and layered fees can quietly erode returns

Guest Bio:

Chaya Slain is the President and CIO at Virtera Partners LLC, an investment firm focused on helping families access institutional-quality alternative investments. She previously worked at a leading family office where she identified gaps in access to private markets for sub-billion-dollar portfolios. Chaya specializes in portfolio construction, manager selection, and integrating strategies like trend following to improve long-term risk-adjusted outcomes.

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We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Chaya Slain:

LinkedIn:https://www.linkedin.com/in/chaya-slain/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, an

(0:00) Introduction (1:05) Importance and challenges of alternative and private investments (2:30) Issues with over-indexing on trendy investments (4:35) Recommended strategies for family offices (7:29) Trend following: explanation, benefits, and role in crises (16:15) Historical performance of trend following (20:05) Trend following vs. traditional portfolios (24:44) Levered treasuries and portfolio construction (25:18) Principal agent problems in large capital pools (26:26) Monthly rebalancing and emotional challenges in trend following (29:17) Strategic ignorance and structural alpha (32:07) Opportunities in lower middle market private equity (34:53) Caution and approach in venture capital investing (38:01) Persistence in venture capital performance (41:11) Advice to younger self on entrepreneurial capital (42:52) Closing remarks