Twitter (NYSE:TWTR) has been a bit of a conundrum for investors. It's a major part of popular culture and has become a platform for everyone to express their opinions concisely, from the president of the United States to comedians, actors, and pretty much every famous person.

The social media site, however, has struggled to turn its audience into revenue. It arguably has a more important place in society than its income reflects, and it has struggled to compete with Facebook, which has dominated social media across the multiple platforms it owns.

Twitter might someday prove to be a strong investment, but that's not the case yet for anyone who invested in its IPO. The company closed its first day of trading on Nov. 7, 2013, at $44.90 a share. In the years since then, it briefly traded above $70, but more recently, it has struggled, closing at $30.55 a share on Dec. 12, 2019.

A text bubble containing two birds.

Twitter has a monetization problem. Image source: Getty Images.

You're in the red

While Twitter did exceed its IPO price earlier in 2019, it has dipped in the latter part of the year. If you bought shares at the Day One close -- $44.90 -- $5,000 would have bought you 111.35 shares. Those same shares would be worth $3,402 as of Dec. 12.

That's a very disappointing return for a company that seems to have managed to become a cornerstone of social media. In many ways, the company's lagging stock price does not appear to reflect its results.

Twitter grew its monetizable daily active users (MDAU) to 145 million in the third quarter. That's a 17% increase, the company's biggest user growth in two years. Revenue also increased in Q3, jumping 9% to $824 million.

The stock price might be struggling because while Twitter is growing, it does not always have a positive reputation. That's partly due to the political divide in the U.S. and partly due to how the company polices the content on its platform. That's something Twitter addressed in its Q3 letter to shareholders:

We continued to make progress on health. In Q3 we gave people more control over their conversations on Twitter with the launch of author-moderated replies in the U.S., Canada, and Japan, and we improved our ability to proactively identify and remove abusive content, with more than 50% of the Tweets removed for abusive content in Q3 taken down without a bystander or first-person report.

That's a start, but the company faces a major challenge in protecting free speech and offering a place users feel good about visiting. Twitter is divisive, and that's not an easy sell to advertisers.

Is Twitter a good investment?

Twitter has managed to become a social media stalwart. That's impressive given the number of companies like MySpace, Friendster, and many others that had a moment and then flamed out.

Establishing a long-term user base that continues to grow gives the company a foundation to build on. That's a start, but Twitter has a lot of work to do when it comes to consumer perception, which impacts its ability to monetize. Advertisers don't want to spend money on a brand people use but don't always feel good about. Changing that is a massive uphill battle for the company -- one that's made harder by President Donald Trump's polarizing use of the platform.

What makes Twitter popular -- its mostly no-holds-barred content -- is also what turns off advertisers. That's a major challenge when it comes to growing revenue that the company has not proven able to solve.

This article represents the opinion of the writer, who may disagree with the “official” recommendation position of a Motley Fool premium advisory service. We’re motley! Questioning an investing thesis -- even one of our own -- helps us all think critically about investing and make decisions that help us become smarter, happier, and richer.