It will be virtually impossible for you to be involved in their IPO. You can contact your brokerage and see if you can be involved but usually there is either a restriction based on how much money you have in your brokerage account or how many transactions you have participated in. As a new investor they are likely just going to say no.

That said, if you can wait until just past the IPO you will be able to purchase shares just like any other symbol.

Do you have an investment account and associated financial advisor? If so you can can ask them if there are shares available for you. During the initial "road show" where the people bringing the company to market visit various banks, those banks will "subscribe" to buy a number of shares at the IPO price. If you bank was one of the ones subscribed you may be able to request some of the shares.

If your bank is not participating, you can simply put in a market order to buy shares on the first day. That isn't particularly smart because if the shares are in a lot of demand the tend to "pop" up in value before sinking again. So for example I watched the Facebook IPO but didn't actually buy any until it dropped down to $18[1] (which was below the IPO price).

The important thing to remember is that if the company is going to be successful, there will be lots of room to grow after the IPO, and if it isn't there will be plenty of opportunities to buy the stock below the IPO price. There is a tremendous amount of activity right around the IPO as the new and old investors sort out their opinion of the value of the company. Its often better to wait a month or two to get a look at how the company is doing before deciding to invest or not.

[1] I then sold half when it hit $36 and the rest when it hit $54.

I would assume it's too late for Twilio, but the next time this happens, there are many companies now that arrange secondary sales where employees can sell some shares so they can use the money to buy a house, car, fund a college education for their child, etc. It is not a liquid investment like a publicly tradable security, but this is a solid option in many cases where you are unlikely to be able to participate in the IPO without connections or a large bank account balance.

You probably can't. The IPO price is what's being shopped around to private institutional investors via the underwriting bank. You can get in early in public trading, however, though that's historically at a higher price.

While I'm not sure starting with IPOs is the best idea for a novice, I recommend questtrade for a cheap canadian brokerage. Here's how you'd do it with them:

https://community.questrade.com/b/diy_investing/archive/2016...

Most brokerages have set aside IPO shares once they have the underwriting all settled in. Contact your brokerage and they will be able to give you more information. They might have certain terms and conditions, such as minimum buy ins, etc.

Consider applying for a job with Twilio.