High-yield ASX dividend shares can be very useful because they send shareholders a rewarding amount of passive income each year. If we're invested in them enough, they could provide a second income.

How good would it be to have a portfolio that paid a quarter of our annual work earnings or even half? That's what I'm looking to get to eventually.

There are a few different names I own in my portfolio that pay me high dividends. While WAM Microcap Limited (ASX: WMI) is my biggest holding with a high dividend yield, I also believe the below two names could pay a lot of dividend income in the coming years.

MFF Capital Investments Ltd (ASX: MFF)

MFF built up a reputation as a listed investment company (LIC) that invests in global shares. It has added an operational element to its business after announcing the acquisition of a relatively small fund manager called Montaka. I like this move because it adds more very capable investors to the MFF investment team.

The business has been steadily increasing its dividend over the last several years and has provided guidance that it intends to grow its half-yearly dividend to 8 cents per share. This translates into an annualised grossed-up (including franking credits) dividend yield of 5.3%.

Its success for the foreseeable future will be based on the performance of its major US share holdings, including Alphabet, Amazon, Visa, American Express, Meta Platforms, Bank of America, Home Depot, and Microsoft. Those businesses seem to have promising outlooks, in my view.

I like the diversification this ASX dividend share offers Aussies and the sizeable dividend yield.

Overall, I think it's a useful position in my portfolio to help me build a second income.

Bailador Technology Investments Ltd (ASX: BTI)

Bailador is a company that invests in small technology businesses.

The high-yield ASX dividend share usually looks for companies that generate repeat revenue, have attractive unit economics, a large addressable market, the potential to grow internationally, and are at the growth stage of their journey, requiring investment.

The businesses inside Bailador are some of the most promising around their size; they just need to deliver on their potential. Some names include Siteminder Ltd (ASX: SDR), Access Telehealth, Rosterfy, DASH and Updoc.

Bailador aims to pay an annualised dividend yield of 4% of its pre-tax net tangible assets (NTA). However, the business is trading at an approximate 30% discount to its NTA as at 31 October 2024. That means the actual dividend yield is 5.8%, or 8.3%, when grossed up for franking credits, which can help build a second income.

That's a solid starting yield, in my opinion, and we can invest at a large NTA discount, which I think is appealing. However, this ASX dividend share is only a small part of my portfolio.