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 inside those months, watching the news and the 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 the time as well as see the numbers.

The films are documentary in tone. They tell 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 whether I could retire. I put all of our information into Boldin, a DIY retirement and financial planning software, then hired their financial advisor team to review the plan and make sure I was seeing it properly. The plan came back with a chance of success in the high eighties, and the advisor told me we were looking good.

I still didn't feel comfortable, and I couldn't say why. I just had a mental block about starting to withdraw from our retirement portfolio instead of depositing into it. I could not get comfortable with it.

I'm a quant developer, so I built a quant algorithm that simulates the three-bucket withdrawal retirement strategy and ran backtests through the last seven financial crises, as far back as my data would allow. The numbers were good. Over the next twenty years the portfolio grew, even with the monthly withdrawals. But the graph also showed a 35 percent drawdown. That is a data point on a chart. Experiencing it is something very different, and I wanted to experience it. How could I transport myself back in time?

For one month, every morning with my coffee, I uploaded one month of the backtest logs to Claude so it knew what my portfolio was doing, and asked what was happening in the financial markets and in politics that was affecting it. It was fascinating, better than watching a television show. I didn't just see it, I felt it: the headlines, what people were feeling, the anger, the frustration, the effect on people's lives, the injustice, the fear. I walked through all twenty years, came out the far side of seven crises with more than I started with, and saw my whole retirement portfolio in a new light.

It gave me the confidence to retire, and it gave birth to this product. I want to share it with you. I hope you get out of it what I did.

Will Berger

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