If you’re ready to turn chaos into clarity and finally take control of your law firm’s money—this year’s Climb to Cash retreat in Aruba (March 16–21, 2026) is where that transformation begins.
This isn’t your typical retreat. It’s a financial strategy lab, wrapped in ocean views and clarity-building sessions, where law firm owners come to stop surviving and start scaling—profitably.
In this preview, I’m sharing three of the core strategies we’ll walk through live at the retreat. If you’re on the fence about joining us, this is your chance to see what real implementation looks like—and why so many lawyers leave Climb to Cash saying, “This changed everything.”
Strategy 1: The CEO’s Cash Flow Command Center
Most law firm owners have no idea how much profit they’ll actually keep next year.
That ends here.
We kick off the retreat by reviewing your real P&L numbers and using tools like FathomHQ, Excel, and AI forecasting prompts to help you:
- Identify revenue gaps,
- Trim excess expenses,
- And build a 2026 financial forecast that adds $500K+ to your bottom line.
Every firm leaves with a custom profit roadmap, supported by real numbers and AI-enhanced insights. Whether you’re a spreadsheet beginner or a data nerd, this session brings your numbers to life.

Takeaway: A complete 2026 forecast based on your actual data—not vibes.
Strategy 2: Your Dream Team Org Chart (Yes, It’s Finally Time)
You can’t scale chaos. And if your paralegal is doing intake, billing, and client communication—let’s be honest, you’re not growing…you’re surviving.
In this workshop, we’ll guide you through:
- The 57 Hats law firm hiring model,
- A full org chart exercise to determine which roles are essential for growth,
- And an AI-supported roadmap that shows who to hire next and how to measure their profit impact.
Whether you’re a solo or managing a team of 10+, you’ll leave with a visual blueprint of what your firm structure needs to look like to grow without breaking.

Takeaway: A hiring plan based on strategy—not panic.
Strategy 3: Automation & Workflows That Buy Back Your Time
You’ve heard the buzz about AI. But how do you actually use it to make your firm run smoother?
At Climb to Cash, we’ll walk you through:
- The exact client workflows you should automate (think: intake, follow-ups, retainer letters),
- How to prompt ChatGPT to build automations for platforms like Clio, Lawmatics, or MyCase,
- And how to reclaim 10+ hours a week by letting your systems handle the stuff you hate.
No tech expertise required. We give you plug-and-play tools, guided prompts, and even worksheets to map your “workflow recipes” live.

Takeaway: A set of custom workflows that reduce stress, increase conversion, and scale with you.
Why Aruba?
We’re not just here to teach—you’ll build and implement your 2026 financial plan in real time, while soaking up Caribbean sun with fellow law firm owners who are just as committed as you.
We chose Aruba because it represents clarity. Open skies, open minds. From curated sessions to beachfront group dinners, we blend business breakthroughs with deep rest so you leave recharged—and ready to lead.
Ready to Scale with Strategy?
We keep this event intentionally small so you get direct access to our team. This isn’t a “note-taking” event. You’ll walk away with:
- Your 2026 profit forecast done,
- A custom hiring and leadership plan,
- An AI-powered workflow and marketing blueprint,
- And a system to finally start paying yourself first.
Seats are already filling—and ticket selling ends soon.