Today, I Repaid My Student Loan. Should I Start Investing in Startups?

I would look into the rule of 9's when thinking about contributing to retirement.

There are a number of people who retire by 40 or earlier, look into early retirement extreme or Mr. Money Mustache. By wisely saving your money in Roth IRA's/IRA's, Brokerage account, rental income properties, you could retire very soon.

A rule of thumb, if you save 75% of your income, you can retire safely at your current standard of living in 7 years. Something to think about when thinking you may die before you get to retire.

There was another post here a few days ago about how to reduce the amount it cost to live, one gentleman is able to comfortably live off of $200/month. If your expenses are so low, image what your life could be like? Work 20 hours a week on your own SaaS project. You will be able to bootstrap a startup and hire employees to take the work load off of you significantly, making a living would be even easier then it is now, and much more exciting.

I would say look at how you want to live when your 40, and head that direction. If you want to be living on a boat, off the anchor, traveling where-ever sail will take you, then you may want to start putting money away in both retirement accounts and brokerage accounts. If you want to be working at the same company you are now, renting in the valley, I would invest that money into yourself, take classes and certifications to boost your resume.

What is your risk tolerance?

That is the very first question you need to ask yourself. If you decide that in the future you won't need virtually instant access to your funds, then you could.

Realize that until investors are chomping at the bit for a share of a company, it isn't very liquid.