How Jonathan uses AI operationally

What changes when wealth stops being about building and starts being about preserving? In this episode, I sit down with Jonathan Dane, CIO and Founder of Defiant Capital, to explore how family offices think about portfolio construction after a major liquidity event. Drawing on his experience at Goldman Sachs and Jefferies, Jonathan explains why independent advice matters and how families navigate the transition from wealth creation to long-term preservation.

Highlights:

• Why large banks struggle to deliver fully independent advice
• The key psychological differences between Gen 1 and Gen 2 wealth
• Estate planning moves entrepreneurs should make years before a liquidity event
• Why gifting shares early can save millions in future estate taxes
• How portfolio construction changes once wealth becomes generational
• Why billion-dollar family offices are typically majority alternatives
• The critical importance of liquidity management before committing to private funds
• Why overcommitting to private equity can force families into bad financing decisions
• The growing frustration with long-dated venture funds and low DPI
• Why lower middle market private equity offers structural inefficiencies
• The operational alpha opportunity in Rust Belt manufacturing businesses
• How independent sponsors should demonstrate real skin in the game
• The biggest mistake $50–$500M families make: over-diversifying into too many managers
• Why AI should enhance diligence workflows but never replace human judgment

Guest Bio:

Jonathan Dane is the Chief Investment Officer of Defiant Capital, where he advises entrepreneurial families and multigenerational wealth on portfolio construction, liquidity management, estate integration, and alternative investments. He previously worked at Goldman Sachs and Jefferies, advising ultra-high-net-worth and institutional clients, and now focuses particularly on lower middle market private equity and operational value creation.

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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.

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

Stay Connected with Jonathan Dane:

LinkedIn: https://www.linkedin.com/in/jonathandane/

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, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why the Sell Side Gives Conflicted Advice (2:03) Why First-Generation Wealth Invests Differently (6:22) The Estate Planning Moves Entrepreneurs Miss (9:02) What Changes Once a Family Passes $50M (10:42) How Billion-Dollar Family Offices Build Portfolios (15:55) Building a Portfolio for a Newly Liquid $1B Family (19:20) Why Families Are Pushing Back on 15-Year Venture Funds (25:12) Why Lower Middle Market Private Equity Works (29:08) Independent Sponsors vs Traditional PE Funds (30:47) The #1 Portfolio Mistake Families Make