In the inaugural Family Office Roundtable at VC10X, host Prashant sits down with Ronald Diamond, Founder & Chairman of Diamond Wealth, and Wendy Craft, CEO of Elle Family Office, for a candid conversation on what's really happening inside family offices today.

From AI tools that are already replacing analysts, to the private equity liquidity crisis, to the $124 trillion wealth transfer heading to the next generation.

⭐ Sponsored by Podcast10x - Podcasting agency for VCs - https://podcast10x.com

What we cover:

- How AI is transforming deal flow, due diligence & the analyst role

- Where family offices are allocating right now — and what's broken in private equity

- Why after-tax returns are the only number that matters

- The rise of ETFs and tax-loss harvesting as game changers for families

- SFO vs. MFO — and why 85-90% of family offices shouldn't exist

- Next gen wealth transfer & why most families are failing at it

- The role of family office capital in solving real-world problems

Timestamps:

(00:00) - Introduction: The Future of Family Offices

(01:26) - Welcoming Guests: Ronald Diamond & Wendy Craft

(02:18) - The Role of AI in Family Offices

(03:40) - A Cautious Approach to AI Investment

(04:52) - How AI is Disrupting Due Diligence

(07:43) - Replacing Analysts with AI to Cut Costs

(09:42) - AI Efficiency vs. The Need for Human Oversight

(11:17) - Case Study: How Large Families Use AI for Efficiency

(13:12) - Can AI Handle Proactive Deal Sourcing?

(14:16) - The Importance of Human Networks in Deal Flow

(15:58) - Portfolio Construction: Public vs. Private Markets

(17:52) - The Problem with Private Equity's Long Lock-up Periods

(19:57) - Contrasting Private Equity with the Family Office Model

(22:30) - The Tax Angle: Liquidity vs. Long-Term Investment

(24:10) - The Growing Focus on After-Tax Returns

(27:00) - The Emergence of ETFs for Tax Efficiency

(29:13) - Venture Capital Investing Styles for Family Offices

(31:28) - Why Inexperienced Family Offices Should Outsource VC

(34:26) - The Rise of OCIOs for Next-Generation Wealth Management

(35:54) - The Future: Outsourcing to MFOs and OCIOs

(38:22) - MFOs vs. OCIOs: What's the Difference?

(41:28) - Educating and Including the Next Generation

(44:20) - How the Next Generation's Investment Interests Differ

(45:00) - The Philanthropic Potential of Family Offices

(48:01) - Youth's Belief in AI to Solve Societal Issues

(49:23) - The Negative Impact of Technology on Mental Health

(54:55) - Portfolio Hedges: Gold, Silver, and Bitcoin

(56:31) - The Evolution of Cryptocurrency as an Asset Class

(58:13) - Skepticism and Risks in the Crypto Market

(01:02:43) - Interest in Gold, Silver, and Critical Minerals

(01:03:23) - Parting Advice for Family Offices

(01:03:54) - Ron's Advice: Run it Like a Business or Outsource

(01:04:56) - Wendy's Advice: The Efficiency of MFOs for Most Families

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Guests:

🔹 Ronald Diamond — Founder & Chairman, Diamond Wealth | Syndicate of 100+ Family Offices ($250M–$30B)

🔹 Wendy Craft — CEO, Elle Family Office | Atlanta, GA

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LINKS

Wendy Craft - https://www.linkedin.com/in/wendy-craft-7281176

Ronald Diamond - https://www.linkedin.com/in/ronalddiamond

Prashant Choubey - ⁠https://www.linkedin.com/in/choubeysahab⁠

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Family Office Roundtable 2026 - $124 Trillion Wealth Transfer, AI, & Private Markets

VC10X - Investing, Venture Capital, Asset Management, Private Equity, Family Office