Family Office Roundtable 2026

The conversation opened where every conversation seems to open right now: artificial intelligence. Both Ron and Wendy had real-world observations — not just predictions.

Ron spotlighted Opto, a platform co-founded by Joe Lonsdale (Palantir, Addepar) and Jacob Miller. He called it unlike anything he had seen before. The platform allows a family office to set precise investment criteria — geography, EBITDA range, sector, ESG filters — and filters every incoming deal against those parameters automatically. Work that would take a junior analyst one to two weeks gets done in seconds.

Wendy confirmed the trend on the ground: several family offices in her Sunbelt network have already eliminated their analyst roles entirely, replacing them with AI programs shared among trusted peers. The cost comparison is stark — $25–50K for AI versus $150–200K or more for a full-time analyst, before you factor in benefits, insurance, and 401(k).

The consensus: AI will not replace the senior decision-maker. Someone like Wendy will always need to pull the trigger, catch hallucinations, and apply judgment. But the layer of people reporting to Wendy? That's shrinking fast.

Wendy also shared a striking example from an Invesco seminar that brought together the Campbell and Walton families: their live AI systems now only escalate to a human when confidence falls below 95%, having effectively eliminated about 20,000 of data entry roles while saving the company from going bankrupt.

Family offices are moving away from public markets and toward private ones — a trend both guests see accelerating.

Ron's view: it's increasingly hard to generate alpha in public equities. Index funds are the sensible default. The real opportunity lies in private equity, venture capital, real estate, credit, and special situations, where companies are staying private longer and alpha is being created before an IPO.

Wendy added important texture. The private equity model has changed — fund timelines that used to run five to seven years now routinely stretch to eight years plus four one-year continuations, sometimes totaling twelve years. Families aren't institutional investors. They have college tuitions, mortgages, and liquidity needs. The result: a growing appetite for private structures that offer earlier distributions and shorter lockups (two to three years rather than ten).

[Note - Wendy is a SFO manager, every family has different preferences for assets, liquidity requirements, timeframes, etc]

Both also noted that tech has stopped being a bucket and become a layer that runs through every other asset class — real estate, infrastructure, healthcare, you name it.

This was one of the sharper points of the conversation. When an institution is up 20%, a family office might only see 12% after taxes — and in high-tax states like New York or California, that can erode further to 6–7%. The pre-tax pitch is noise.

Key trends they're watching:

Wendy was blunt: if a deal requires filing returns in twelve states, she won't do it. The compliance cost alone kills the math.

With $124 trillion moving from baby boomers to the next generation, the question of how to prepare the next generation is existential — and most family offices are failing at it.

Ron's sobering stat: only 25% of family offices survive to the second generation, 10% to the third, and 5% to the fourth. Part of the problem is that the wealth creator — whether they built a perfume company or a widget business — isn't necessarily a skilled investor, and often doesn't build the infrastructure to outlast themselves.

Wendy's approach with the family she serves: financial education every single day, weekly meetings with next-gen members on financial terminology, trading simulations via platforms like TradingView. The family brings one of their daughters to every conference and seats them on next-gen panels. Her observation: at most family office conferences, there are zero actual next-gens in the room. You can't prepare them for stewardship while excluding them from the conversation.

Ron also noted a values shift: younger inheritors screen investments for labor practices, environmental impact, and social responsibility in ways their parents never did. Impact investing didn't come from the top down — it came from the next gen up.

One of the most practically useful parts of the conversation was the frank advice on when not to run a single-family office.

Ron's position: 85–90% of existing family offices shouldn't exist. Many are driven by ego. The economic breakeven is roughly $500 million in investable assets. Below that, an MFO almost always makes more sense — lower cost, better talent access, and more flexibility.

Wendy's framework for choosing an MFO:

The one legitimate reason to build a single family office: privacy. If the concentration of outside professionals handling your affairs creates unacceptable confidentiality risk, a dedicated SFO may be worth the cost. Otherwise, a well-chosen MFO offers better outcomes for most families.

The conversation broadened into territory that doesn't often get discussed at family office conferences.

Ron made the case that family offices, run with the discipline of a venture firm, may be better positioned to solve major societal problems than governments or traditional nonprofits. He pointed to Michael Milken's funding of prostate cancer research, Eric Lefkofsky's founding of Tempus (now a public multi-billion dollar oncology company) to find treatments for his wife's breast cancer, and Bill Gates's outsized role in the COVID response as examples of capital with a long time horizon and mission-driven focus driving breakthroughs.

But he was equally candid about the risks. Elon Musk's estimate that 25–50% of entry-level white collar jobs could be eliminated by AI is, in Ron's words, "a little scary." He cited Jonathan Haidt's The Anxious Generation on the mental health crisis among 18–25 year olds traced to smartphone and social media use, and called for more countries to follow Australia's lead in restricting social media access for minors.

Wendy introduced the concept of the "dark enlightenment" — a current of thought, well-known among Gen Z, that AI will eventually solve wealth disparity, healthcare inequality, and other structural problems. She noted that next-gen family members are already thinking through how to align their investment and philanthropic activity with that vision.

Connect with:

Wendy Craft, Ronald Diamond, and Prashant Choubey

Want to dive deeper? Listen to the full episode to get all the insights.