Jonathan Dane, Founder and President of Defiant Capital Group, recently joined David Weisburd on How I Invest – one of the leading podcasts at the intersection of private markets and family office wealth. The conversation covered what a sound family office investment strategy actually looks like: from why big banks structurally cannot give independent advice, to how the wealthiest first-generation founders construct their portfolios after selling a business.
Use the links below to listen/watch to the full episode:
➡️ Listen on Apple Podcasts / Spotify
➡️ Watch on Youtube
The Problem With Big Banks (And Why It’s Structural)
The issue isn’t that the people at large institutions are bad. It’s that the business model is broken.
- When custody, advice, and product manufacturing all live under one roof, conflicts are baked in by design, not by accident
- Advisors who are incentivized by proprietary product sales cannot give you fully objective advice, no matter what the disclosure says
- Fee waivers tied to specific products are not a gift – they’re a signal
Defiant Capital Group was built differently – we don’t manufacture anything so that we can always deliver unbiased, fiduciary advice. That means we can evaluate the entire universe and choose what actually fits.
The $50 Million Inflection Point in Family Office Strategy
Not all wealth management looks the same. There’s a meaningful threshold around $50M where the game fundamentally changes.
Below $50M: The focus is on generating returns, finding deals, and building toward liquidity. Scrappy investing, concentrated positions, and growth orientation dominate.
Above $50M: The conversation shifts to legacy, governance, and generational durability. Now the questions are:
- What does the family office structure look like?
- Which trust holds which asset?
- How does the investment plan tie into the estate plan?
- Who controls what, and for how long?
If you’re approaching that threshold and you’re not already asking these questions, you’re late.
How the Wealthiest Families Build Their Investment Strategy
At the billion-dollar level, portfolio construction looks nothing like a typical brokerage account. Key principles we discussed during the interview:
- Liquidity first. Before anything else, map out cash flow needs and capital call obligations. Overcommitting to private funds without a liquidity plan is one of the most common, and most damaging, mistakes we see.
- Alternatives dominate. Well over 50% of the portfolio sits in alts across private equity, real assets, and venture. And importantly, each sleeve serves a distinct role.
- Tax-aware investing isn’t optional. Half the managers in the alt space have never had to think about taxable investors. But for most families, net-of-tax, net-of-fee returns are the only number that matters. If a manager can’t show you how they’re thinking about your K-1, that tells you everything.
- Build around strengths. The best post-liquidity portfolios are shaped around where a family has genuine expertise and conviction, not around what a fund wholesaler is pitching.
Where We’re Investing Today: Lower Middle Market PE and Alternatives
In the interview Jonathan shared his conviction views on the private markets landscape:
- Lower middle market private equity remains the most attractive inefficiency in the alt space. Mega funds can’t write $30–40M equity checks. That creates real opportunity, especially in Rust Belt manufacturing, distribution, and industrial businesses where operational value is waiting to be unlocked.
- Co-investment matters more than ever. The 15-year venture lockup question is real. Families want to see DPI, not paper marks. Co-invest rights alongside trusted managers are how you address that.
- Independent sponsors with skin in the game can be exceptional partners. But make sure they’re putting their own capital in and treating the deal like their life’s work.
Our Philosophy, In Plain Language
It’s only helpful if it helps. That’s the standard we hold ourselves to at Defiant. Every analysis, every call, every recommendation has to clear that bar.
We start with what a family actually needs and not with what’s on our shelf.
