About this episode
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.
Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.
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 lear
