Epiisode 46: Building a $25M+ Minimum Family Office for First-Gen Entrepreneurs

What does it take to build a family office with a $25M minimum and serve first-generation entrepreneurs navigating complex wealth? This episode breaks it down.
In this episode of Sterling Insights, Roger sits down with Chad Willardson, founder of Pacific Capital and advisor to ultra-high-net-worth founders. Together, they explore how to serve first-gen entrepreneurs with complex financial lives, sharing valuable insights and practical tips for advisors and families alike. Chad draws from his extensive experience building a boutique family office to discuss client fit, private investments, multi-generational planning, and how to say no—even to $100M prospects, offering actionable advice for those working with high-net-worth individuals. This episode is a must-listen for financial advisors, family office professionals, and entrepreneurial families, providing both knowledge and tools to navigate this important subject.
Key Takeaways:
● 💼 Know Your Ideal Client: Why Chad only serves first-gen founders with $25M+ and how he defines perfect-fit clients.
● 🧠 Be the Peer, Not Just the Planner: How being an entrepreneur himself makes Chad more effective as an advisor.
● 📊 Private Deals Are Everywhere: How his team evaluates hundreds of private investment opportunities each year for clients.
● 🧒 Smart, Not Spoiled: Why teaching kids about money early is essential—and how not to ruin the next generation.
● 🛩️ Lifestyle Decisions Matter: What to consider when clients ask, “Should I buy a jet?”
Quotes from Chad Willardson:
● "I’m more of a peer to my clients than just their advisor."
● "You don’t have to do business with people who aren’t a good personal fit."
● "Making money easy doesn’t make someone good with money."
🔗 Conclusion:
Serving ultra-wealthy entrepreneurs isn’t just about investing—it’s about simplifying their lives, protecting their time, and helping them think clearly in high-stakes moments.
Connect with Chad:
Website: http://chadwillardson.com/
Connect with Roger:
Website: https://www.sterlingfoundations.com
Facebook: https://www.facebook.com/sterlingfoundations/
Twitter: https://x.com/SterlingFndMgt?mx=2
LinkedIn: https://www.linkedin.com/company/sterling-foundation-management-llc/
Learn more about your ad choices. Visit megaphone.fm/adchoices