About Rewind Portfolio

Most retirement plans are judged by a line on a chart. The line is accurate, but it leaves out the part that matters most: what it is like to live through those years month by month, watching the news and your balance at the same time.

Rewind Portfolio exists to show that part. We take a real plan, set it at the start of a real stretch of history, and walk it forward one month at a time. Each month pairs what was happening in the world with what the portfolio did, so the viewer can feel what that time was like as well as see the numbers.

The films are documentary in tone. They show what happened, in order, and let the viewer draw their own conclusions. They never tell anyone what to buy, sell, or do.

I'm 58, and for a long time I wasn't sure I could retire. I put all of our information into Boldin, a do-it-yourself retirement planning tool, then hired Boldin's advisor team to review the plan and make sure I was reading it correctly. The plan came back with a success rate in the high 80s, and the advisor walked me through it in detail, explaining why she felt we were ready to retire now.

I still wasn't comfortable, and I couldn't say why. I had a mental block about drawing money out of our retirement portfolio instead of putting it in.

We've always been told you retire at 65. Stopping earlier felt like going against the norm, and I kept asking myself whether I was being irresponsible. Underneath it was fear of the unknown. What trouble lay ahead? Would we have enough money? And if the stock market tanked, how would we get through it?

I'm a quant developer, so I wrote an algorithm that simulates the three-bucket retirement withdrawal strategy and backtested it through the last seven financial crises, as far back as my data would go. The numbers were good: over those twenty years the portfolio grew, even with the monthly withdrawals. But the graph also showed a 35 percent drawdown. On a chart, that's a single data point. Living through it is something else, and I wanted to live through it. How could I go back in time?

Every morning with my coffee, I uploaded the next stretch of the backtest logs to Claude so it knew what my portfolio was doing. Then I asked what was happening in the markets and in politics that was moving it. It was better than any television show. I didn't just see it; I felt it: the headlines, the anger and frustration, the fear, the injustice, the effect on people's lives. I walked through all twenty years, came out the far side of seven crises with more than I started with, and saw my retirement portfolio in a new light.

It gave me the confidence to retire, and it's why this product exists. I want to share it with you. I hope you get out of it what I got.

Will Berger

Rewind Portfolio is built by Quant Makers LLC. Boldin is an independent planning service and is not affiliated with Rewind Portfolio.