Built by planners. Designed for people who want clarity.
Ready Aim Retire was created by two lifelong retirement planning enthusiasts who believe something simple but powerful.
Start Planning for FreePeople make better decisions when they truly understand their own plan.
Not just the outcome - but the why behind it.
Our Story
It started with a simple question:
"Why is this so hard?"
In 2010, long before modern retirement tools became readily available, Greg Simmons built the first version of a retirement planning system for his own use.
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Spreadsheets were fragile and hard to maintain - Professional-grade software was powerful, but inaccessible
- Most tools answered "Will this work?" without helping people understand why
Like many thoughtful planners, he found that:
So Greg did what engineers and planners often do: He built something better.
That original system focused on clarity, flexibility, and seeing the full picture over time - not just producing a single answer.
A New Chapter
From personal tool to global platform
In 2025, Greg teamed up with Ross Williams to reimagine and rebuild the platform from the ground up - this time with a much bigger goal:
- Take control of their financial future
- Understand their tradeoffs
- Build confidence in their decisions
- Stay engaged with their plan over time
To make sophisticated retirement planning accessible to DIY planners everywhere. Together, they created Ready Aim Retire - a modern, intuitive retirement planning tool designed for people who want to:
Whether you're years from retirement or already living it.
Meet our founders
Ross Williams
Educator. Advocate. Plain-English communicator.
Ross has built his career helping thousands of individuals navigate the complexities of retirement planning. He is deeply passionate about financial literacy and believes that people should never feel intimidated by the tools meant to help them.
Ross brings a user-first mindset to Ready Aim Retire - ensuring that the platform speaks plain English, stays practical, and always serves the person using it.
Greg Simmons
Builder. Systems thinker. Retirement modeler.
Greg has spent decades thinking deeply about how money, time, and uncertainty interact over a lifetime. He brings a long history of building thoughtful financial models and a belief that good tools should reveal insight, not hide it.
His work has always focused on accuracy, transparency, and helping people see the full arc of their financial lives - not just short-term projections.
Why We Built Ready Aim Retire
We believe:
- Financial literacy is empowering
- Understanding beats outsourcing blind trust
- Visualization builds confidence
- And retirement planning is too important to leave to guesswork
Ready Aim Retire exists to give people the tools, insight, and confidence to actively participate in their own journey toward financial independence and freedom.
Not by promising certainty - But by helping you understand your path.
Our Mission
Helping people see their future - and plan it with confidence
Our mission is to promote financial literacy and provide powerful yet approachable tools that allow individuals to:
- Understand their retirement timeline
- Explore meaningful 'what-if' scenarios
- Make informed, confident decisions
- Adapt as life changes
We don’t believe in one-size-fits-all plans. We believe in informed choices.
The Bottom Line
Ready Aim Retire was built for you - the thoughtful, engaged planner who wants clarity, control, and confidence in the years ahead.
If you care enough to plan, you deserve tools that turn your plan into reality.