“How-To” – Finance & Cash Flow Talking About Money—And Making It Work for the Business and the Family

“How-To” 🛠️💰 — Finance & Cash Flow: Talking About Money—and Making It Work for the Business and the Family 📊🏡

How To’s for the Family Business
A series of practical conversations about the real work of running a family business—how you lead, communicate, and make decisions along the way.

Each conversation focuses on a different part of the work—how your business grows, how your people experience it, how decisions get made, and how things actually run day to day.

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Money is one of the hardest things to talk about in a family business—especially when expectations aren’t fully shared or have built up over time. You may already be feeling the pressure in small ways—unclear expectations, decisions put off, or conversations that don’t quite happen. Often, it’s not just what’s said about money, but what’s assumed—and left unspoken—that creates the most tension.

This conversation includes practical ways to strengthen cash flow while also making it easier to have clearer, more direct conversations about money. We’ll look at common patterns that create pressure—like inconsistent billing, unclear expectations, or avoiding difficult decisions—and how to address them in a steady, workable way.

There will also be space to talk about what fairness looks like across roles, generations, and ownership structures, and how to put simple agreements in place that reduce friction over time.

The goal is not to turn you into a financial expert, but to help you create more clarity and alignment around money—so it supports both the business and the relationships behind it.

Speakers: Jacques Santucci, Opus Consulting (Moderator); Byron Skaggs, Infinite Ping, Inc.; Carrie Yardley, Yardley Esq. PLLC and TBD

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Midday Conversations

Continue the conversation (online) with Live Zoom Videocast:  12 noon – 1 p.m.

Short online conversations that continue the How To Series, offering practical ways to go a bit deeper on specific topics.

Sponsored by: The Breakwater Group at Morgan Stanley and Mainebiz

• Using lean strategies to improve clarity and reduce strain (Clarity & Efficiency)

– Wednesday, January 13, 2027

Speaker: Priscilla Hansen Mahoney, Blazing Trails Coaching

Sometimes the pressure in a business comes less from big problems and more from unclear processes, constant workarounds, and too much resting on too few people. Continuing our conversation on finance and cash flow, this Midday Conversation explores how Lean strategies can create more clarity, reduce friction, and support healthier day-to-day operations—without losing the human side of the business. Through practical examples and simple tools, Priscilla Mahoney will share ways family businesses can improve communication, reduce operational strain, and build systems that better support both people and performance.

• Understanding loan covenants as your business grows (Debt & Documentation)

– Thursday, January 28, 2027

Speaker(s):  TBD from Camden National Bank

As businesses grow, loan documentation often becomes longer and more complex—and not always easy to understand or talk about. This conversation continues our discussion around money, clarity, and shared expectations by helping leaders better understand loan covenants, financial reporting requirements, and the kinds of loan agreements that can shape future decisions. We’ll focus on practical understanding, not financial expertise.