Ep54: Bill Winterberg – Losses Mean No Chance for Money to Compound

Listen on

Apple | Overcast Stitcher | Spotify | Other

Guest profile

Bill Winterberg is the founder of FPPad, a technology publication and business consulting firm to financial services organizations.  Bill produced the FPPad Fintech Flash Briefing and was the host of FPPad Bits and Bytes, video broadcast and email newsletter covering technology news and information for financial professionals. He provided technology commentaries for the Journal of Financial Planning and was the monthly technology columnist for Morningstar Advisor.  InvestmentNews recognized Bill as a 40 Under 40 Honoree for his influence in the industry, and he was named to the 2013 IA 25 list of the most influential people in the profession. Before entering financial services, Bill was a software engineer for Hewlett Packard and LeapFrog Toys. On a personal note, he lives in Atlanta, GA with his wife and nine-year-old son.

Listen to Bill as he shares his worst investment ever story purchasing a manufactured home that he and his wife bought out of a loan, the events that made them decide to sell the property, the tedious selling process they’ve experienced, and the ballooning interest loans that they had to settle while trying to let go of the property. Don’t miss out this truly relevant story of decision making and learn from the consequences that Bill made.


It doesn’t even necessarily need to be whether or not this investment has gone bad or is still good, but some or many times, circumstances happen in your life that you cannot predict.”

Bill Winterberg


Topics Covered:

01:23 – Bill’s personal and professional experience  

05:14 – Bill shares how he purchased a home in San Francisco and how it ended up as a bad investment after a life-changing situation

18:21 – Lessons learned by our guest

20:36 – Andrew shares his three takeaways from this story: knowledge in your investment, criticality in timing, and the concept of inches and seconds

23:24 – Highlighting the compounding effect of money

26:21 – Andrew wraps up the show with remarkable teachings from the book “Your Money or Your Life”

27:41 – Encouraging last words from Bill: “Take what you learned from our discussion today and apply it not just to an anecdotal story like what you just heard, but apply it to your opportunities today and your opportunities in the future.”

Main Takeaways:

Lesson 1: “Try your best not to underestimate the value of flexibility, and liquidity is important in there too.”– Bill Winterberg

Lesson 2: “We were not wise to the fact that there was this language in the location of the house that restricted that flexibility. It took us two years to sell. It’s that liquidity and not having any offers to buy for two years.”– Bill Winterberg

Lesson 3: “The real benefits of compounding don’t come to us until 20 or 30 years later.” – Andrew Stotz

Lesson 3: “A common thing that people say (in investing in the stock market) is to make mistakes while you’re young because you can recover from them. But what I say, in the world of finance don’t make your mistakes when you’re young because the compounding impact of those financial mistakes is enormous.” – Andrew Stotz

Lesson 4: “That book (Your Money or Your Life) taught me that, ultimately, is when we’re spending, we’re spending our energy and what I learned from that book is to live deeply below your means. And I believe that that challenged me throughout my whole life to see if I could live deeply below my means.” – Andrew Stotz


Connect with Bill Winterberg:

Andrew’s books

Andrew’s online programs

Connect with Andrew Stotz:

About the show & host, Andrew Stotz

Welcome to My Worst Investment Ever podcast hosted by Your Worst Podcast Host, Andrew Stotz, where you will hear stories of loss to keep you winning. In our community, we know that to win in investing you must take the risk, but to win big, you’ve got to reduce it.

Your Worst Podcast Host, Andrew Stotz, Ph.D., CFA, is also the CEO of A. Stotz Investment Research and A. Stotz Academy, which helps people create, grow, measure, and protect their wealth.

Leave a Comment