As well as Reddit and Condé Nast, the group owns the Ironman long-distance race group and is the largest shareholder in Warner Bros Discover and telecoms giant Charter.

Until 1998, the group owned the Random House book publisher.

Samuel Jr, known as Si, commissioned Donald Trump’s The Art Of The Deal in the 1980s.

Advance spun out Reddit as a separate company in 2011 but it is still poised to make a huge profit on its investment.

Reddit began an investor roadshow on Monday and is likely to adjust its expected share price as it responds to investors’ feedback.

The flotation will be one of the biggest of the year so far and is being closely watched as a test of investors’ appetite for new listings.

Other major investors include Chinese internet giant Tencent, which owns an 11 per cent stake, and Sam Altman, the chief executive of ChatGPT’s developer, OpenAI.

Altman, who led a 2014 funding round, owns 8.7 per cent of Reddit. This is worth up to $US413 million based on Monday’s pricing range.

Reddit could raise as much as $US748 million in the New York Stock Exchange listing, making it the biggest social media flotation since Pinterest’s stock exchange debut in 2019.

However, even at the optimistic end of its valuation range, it will be worth far less than the $US10 billion at which the company raised funds in 2021, the peak of a tech investment boom.

Reddit has around 73 million daily users who join communities known as “subreddits”, dedicated to their favourite sports teams, local city or hobbies.

It is famous for features such as “ask me anything” events where celebrities respond to users’ questions, and its system of upvotes and downvotes, which determine what comments appear at the top of discussions.

In 2021, its Wall Street Bets community was the centre of the “meme stock” trading craze that sent the share prices of companies such as GameStop soaring and led to claims of an investing revolution.

The number of users has grown by 27 per cent over the last year, while revenue climbed by 21 per cent to $US804 million, almost all of it from advertising.

Reddit has also recently been boosted by changes to Google’s search algorithm that have prioritised authentic material over spam web pages.

However, the company faces a string of questions and concerns that may deter prospective investors. Eighteen years into its existence, the company has never turned an annual profit and lost $US90.8m last year.

This is despite the company outsourcing a significant amount of work to volunteer “moderators”, who police various subreddits and determine their rules.

Reddit is also known for its often unruly and opinionated user base, which has repeatedly landed the company in trouble.

Its management tied itself in knots for years over a subreddit devoted to Donald Trump that became a hotbed of conspiracy theories.

In its early days, Reddit was also notorious for containing non-consensual explicit images and harbouring racist communities.

The flotation will be one of the biggest of the year so far and is being closely watched as a test of investors’ appetite for new listings.

The company has since purged its worst elements but can still find itself hostage to users’ whims.

Last year, thousands of subreddits became inaccessible to the public in a revolt against plans to start charging for access to large amounts of Reddit data.

Loading

The artificial intelligence revolution has created a new opportunity.

It has struck a $US60 million a year deal with Google, under which the search giant will use Reddit’s valuable data to train its AI systems.

But to be a success, it will have to overcome the scepticism of its users.

Comments about Reddit’s stock market listing on the Wall Street Bets subreddit have been overwhelmingly negative, flooded with posts seeking advice on how to bet against the company.

The Telegraph, London

The Business Briefing newsletter delivers major stories, exclusive coverage and expert opinion. Sign up to get it every weekday morning.