The Out Loud with AI Series
A practical book series for thinking through money, investing, and retirement — with AI as your thinking partner.
Coming Soon
Available Now
Available Now
About the Series
The Out Loud with AI series helps you think through each stage with more clarity and less pressure.
How the Books Work
Step 1
Read a real story
Each chapter opens with a real situation — someone facing a decision that probably sounds familiar.
Step 2
Think through the tradeoffs
See how decisions actually play out. Separate what matters from what doesn't.
Step 3
Continue with AI
Use guided prompts to explore your own situation. AI helps you think. You stay in control.
Books in the Series
You don't have to start at the beginning. Start with the decision that's actually in front of you.
Book 1 · Available Now
Less Noise. Better Investing Decisions.
You don't need to predict the market or find the perfect investment. You need an investing approach you understand — one that fits your goals, your timeline, and your ability to live with risk. This book helps you get there.
Book 2 · Available Now
Less Noise. Better Retirement Decisions.
Retirement is not one decision. It's a series of decisions about money, time, work, family, housing, healthcare, and what you want the next part of life to look like. This book helps you work through them — one at a time, with AI alongside.
Book 2 · Canadian Edition
Less Noise. Better Retirement Decisions.
Built for Canadian retirement — CPP, OAS, RRSP, TFSA, and more. Also covers cross-border situations for Canadians who have lived or worked in the US.
Book 3 · Coming Soon
Less Noise. Better Money Decisions.
Everyday money decisions — spending, saving, borrowing, planning — are rarely just about money. They're about priorities, tradeoffs, and what you're actually trying to build. This book helps you make those choices on purpose.
Who This Series Is For
You keep putting it off
You know you should make a decision, but something keeps getting in the way.
Information overwhelms you
Financial advice leaves you feeling more confused, not less.
You want to think, not be told
You'd rather understand the tradeoffs than just follow a rule.
You learn through stories
Real examples land better than formulas and frameworks.
You want to use AI thoughtfully
You're curious about AI but want to stay in the driver's seat.
You want to own your decisions
You want choices you can explain, defend, and actually live with.
You don't need to be a financial expert.
You just need a decision worth thinking through.
About the Author
Anna Kwan is an author and former product leader with more than 20 years of experience helping people make sense of complicated choices — in banking, online investing, financial services, and tech.
She is not a financial advisor. She comes to this work as someone who has watched thoughtful, capable people feel overwhelmed by decisions they were perfectly able to make — and wanted to do something about that.
She lives in Bellevue, Washington, with her family and a house full of dogs.
You don't need the perfect answer. You need a clearer way to think through the next decision.
Explore the Books →