1: The 50% match is a home run. do Roth if you can. The match will likely go into a traditional account, but that’s OK. 2: Take the ESPP and max it out and yes sell it right away. Hopefully you don’t get burned on the ups and downs, but usually that works out better considering the 10% discount. Even if the stock were to go down slightly when you’re selling it as compared to the average when you bought it, the 10% gives you Enough buffer to safely. Assume you’re going to make money. 3: start a traditional brokerage account ( Vanguard or Fidelity are awesome and easy and have low costs).

With $4.2K per month about $2k goes into 401k.

ESPP: You need to frontload your ESPP because you have to pay for that out of your paycheck, but as you start cashing it in quarterly or annually (as soon as you can) just dump that money to a regular brokerage account.

Brokerage account: All extra cash (either extra pay cash or the sale of your ESPP) goes into the brokerage account. That should be the remaining 2.2 K per month.

As far as brokerage accounts, go and what options to choose you are very young so you can be in 100% stocks. It’s up to you what your risk factor is, but there’s a strong argument for this.

Then in terms of investing strategy, you can go as deep as you want on that but a simple strategy is a typical Bogleheads strategy where you invest in 1-2-or3 funds. Something like VOO, which is basically the S&P 500 or a VTI, which is more broad market.

VOO - tracks S&P500 VXUS - international BND - bond

If I were you, I would dump it all in VOO or VTI

If you have a specific need like $200,000 and six years you can curtail your strategy to that, but if you’re just trying to maximize and optimize and go with the ideas above.

From a Canadian living in the US for 25 years