In our latest Ask an Expert session, I had the chance to speak with Sara Hobbs of Forecastle Financial, a Personal CFO who works directly with high-net-worth households.

We talked about what it means to be a Personal CFO and how Sara’s role includes much more than bookkeeping. She acts as a strategic advisor, looking at cash flow, lifestyle planning, and reporting, with a level of insight and care that is rare in the private service world. What stood out was how she values relationships and trust. She is genuinely wants to help people manage the financial side of their lives with clarity and confidence.

The questions from our community were smart and very relatable. We covered things like working without a formal budget, being held responsible for overspending without visibility, and trying to create financial structure when there is none. This is where Sara comes in; she acts as a bridge between estate staff, family offices, accountants, and principals, especially when that communication is not flowing smoothly.

We addressed technical pain points, including how to manage petty cash, track receipts, streamline vendor payments, and create reporting that is clear without overwhelming a principal. Sara shared a few tools such as Keeper, Monarch Money, and bill.com. She agreed there is a need for something tailored to how estates function.

What I appreciated most was Sara’s openness. She was there to listen, learn, and offer real help. By the end of the session, it was clear we had started a valuable conversation. There is a need for better systems, more training, and practical resources in estate finance. Sara is already thinking about how to build those with us.

This conversation was a starting point and we look forward to continuing the discussion and creating new programs to aid in financial literacy for Estate Managers.