President Donald Trump wasn’t always the commander-in-chief; prior to having engaged in a political career which has seen him become the 45^th and 47^th president of the United States in serving non-consecutive terms, Trump was known as a businessman — and later, media personality — who partook in a variety of different entrepreneurial ventures.

Trump’s Economy: Why Millennials Love It and Boomers Don’t

Read Next: 10 Used Cars That Will Last Longer Than an Average New Vehicle

If you’d backed those publicly traded ventures in the 1980s, how would your investments be faring today?

Launched to much fanfare in 1995, Trump took Trump Hotels and Casino Resorts public, attracting $140 million in stock purchases from investors betting big on the well-known real estate tycoon.

However, with Trump at the helm, holdings went from a single Atlantic City Casino to quickly snatching up debt-burdened Taj Mahal and a third Atlantic City casino, both previously owned by the now-president himself.

A number of personal loans borrowed from the company followed suit, according to a Forbes report, and eventually, the company lost $647 million from 1995 through 2004, when it declared bankruptcy.

Learn More: How Paychecks Would Look in Each State If Trump Dropped Federal Income Tax

Following the initial 2004 bankruptcy, Trump Hotels and Casino Resorts was renamed as Trump Entertainment Resorts.

And while Trump was paid $2 million per year despite stepping down as CEO (after receiving an approximately $50 million for services and rents rendered during his tenure as chief over Trump Hotels and Casino Resorts), that company lost $189 million in 2007 and a further $232 million in 2008.

On Feb. 13, 2009, Trump as well as his daughter, Ivanka Trump — installed on the board in 2007 — resigned their posts. On Feb. 17, Trump Entertainment Resorts declared bankruptcy.

Today, Trump Entertainment Resorts exists as a fractional penny stock with negligible value, meaning that investors who did not sell their shares earlier would be essentially left with no value.

Trump Media & Technology Group remains in play, however, with majority ownership resting in the hands of the president. The company is most notably involved with Trump’s Truth Social social media platform, although in recent days it has been dedicated to building a substantial Bitcoin treasury reserve.

According to Benzinga, the SEC recently gave the nod of approval for Trump Media to expand upon these plans with a slated $2.3 billion capital investment, coming from more than 50 institutional investors.