How to Money · Monday, June 29, 2026
A listener named Matt questions the best strategy for his Employee Stock Purchase Plan (ESPP), which offers a 15% discount and a look-back provision. He believes a quick sale offers a guaranteed return but is unsure about tax implications and diversification.
“My question is it seems like from the research I'm doing that doing a quick sale of the ESPP is a no brainer that I get a I think it's like a seventeen percent return on investment no matter what, and that assumes that the stock does not perform well between now and the purchase states.”
“It doesn't seem like the tax implications of this are anything to be worried about, So I'm just curious what your thoughts are. What else do I need to consider or should I utilize a ESPP and just hold the stock.”
“I think it's important to note that I do believe in my company stock. I think I'm in a good industry and a good company with great growth projections. But I just don't like having all of my eggs in one basket or one stock.”
“So I'd rather get the guaranteed ROI cash that, out sell it, and potentially consider putting that money into a well diversified index fine or RETF.”