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Jon Stein: 'Free Trading Is Actually Going to Cost You'

The Betterment founder and CEO on evolving beyond robo-advice, client behavior during the recent market swoon, and deterring harmful trading activity.

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Our guest this week is Jonathan Stein, the founder and chief executive of Betterment. Stein founded Betterment in 2008 as an automated, goals-based investing service, and it's currently the largest of the independent robo-advisors. Betterment offers two main services--Betterment Digital, which is a pure robo-advisor, and Betterment Premium, which offers clients ongoing financial planning guidance from a Certified Financial Planner. Stein began his career consulting with banks and brokerage firms on risk and products. He's a graduate of Harvard University and Columbia Business School and holds the Chartered Financial Analyst designation.


Jonathan Stein bio

"Betterment: Jon Stein," How I Built This with Guy Raz, Oct. 26, 2018. 

"Jonathan Stein Built Betterment to Help Investors Make Better Decisions," by Bruce Rogers,, Jan. 18, 2018.

The Coronavirus and Investor Behavior

"Thoughts on the Volatile Market," by Jon Stein,, March 19, 2020.

"COVID-19's Impact on Investor Sentiment,", May 6, 2020.

"How Betterment's Customers Are Behaving Amid the Volatility," by Caleb Silver,, April 10, 2020. 

"Betterment Halted Trade Amid Brexit Panic--Here's Why," by Anora Mahmudova, MarketWatch, July 1, 2016. 

"Coronavirus Turmoil, Free Trades Draw Newbies Into Stock Market," by Alexander Osipovich and Caitlin McCabe, The Wall Street Journal, April 29, 2020. 

"Americans Are Hoarding Cash: Savings Rate Hits Its Highest Level Since 1981," by Paul R. La Monica,, April 30, 2020. 

Betterment's Offerings and Investment Process

Betterment Digital vs. Premium 

Betterment's Cash Analysis Methodology 

"Are Robo-Advisors Better Than Target-Date Funds?," by Arielle O'Shea, NerdWallet. 

Betterment for Business

"How Tax Impact Preview Works to Help Avoid Surprises," by Boris Khentov,, Oct. 29, 2014. 

"ETF Selection for Portfolio Construction: A Methodology," by Adam Grealish,, Aug. 27, 2014. 

"Value Investing: Research on the Risk and Return," by Adam Grealish,, Oct. 25, 2016.

Future of Advice

"The Fiduciary Rule Should Be Fully Implemented," by Jon Stein,, June 8, 2017.

"Will New SEC Regulations Change Anything for Retail Investors?" by Theresa W. Carey,, June 8, 2019.  

"The Future of Advice: Jon Stein, Betterment," March 6, 2017. 

Betterment Paints It Black in Robo-Retail," by Oisin Breen,, Aug. 5, 2019.