Mark Cuban has had quite the successful run in the tech industry, successfully starting and selling businesses at the opportune time and using his profits to invest in the next big thing.

Thus far, the entrepreneur and tech expert has been hesitant to mark Bitcoin and cryptocurrency as that “big thing.” Over the years, Cuban has come around on the concept somewhat but—despite the recent announcement that his Dallas Mavericks will accept cryptocurrency as payment for tickets next year—has maintained a level of skepticism.

At SXSW in March 2014, Cuban told USA Today that bitcoin had a purpose—but it wouldn’t be to replace money. At the annual entertainment festival, Cuban declared that bitcoin was “great as an encryption technology,” but not as a currency.

“As a transport mechanism, an accounting digital transport mechanism, it’s unique and has a great opportunity in the future,” Cuban he said. “I think it’s got no shot as a long term digital currency.”

At the time of Cuban’s comments, bitcoin was enjoying a bit of a boon. The cryptocurrency was recovering quickly from a sudden drop that cost it more than one-third of its total value and appeared to be climbing back up to the $700 range, which at the time would have been near its peak value.

The days that followed Cuban’s comments quickly wiped up the recently recovered value. Within a matter of weeks, bitcoin was back below $500 and wouldn’t recover for the better part of two months.

Cuban again spoke on the topic of cryptocurrency in the fall of 2014, when he told Entrepreneur that he was wavering on bitcoin. “Nope, I haven’t invested in bitcoin yet,” Cuban told the publication. “I go up and down on it.”

At the time, Cuban said that if he ever did buy into bitcoin, it would be “more as fun” than as an actual investment. “It’s almost like buying and selling baseball cards, but there’s definitely risk involved if you’re looking at it to be a long-term currency,” he said, though he left open the possibility of adding the cryptocurrency to his profile at some point in the future.

Cuban’s comments again came just before the bitcoin market started a slide. Valued at around the $400 range at the time, bitcoin dropped below that threshold and largely remained there, at times even dipping into the low $200 range for days at a time.

Cuban remained largely mum on bitcoin until the currency started to talk off in 2017. Over the course of the year, the cryptocurrency grew exponentially, jumping from a value of under $1,000 at the start of the year and peaking at just short of $20,000 by December.

In June of last year as bitcoin was climbing toward the $3,000 threshold, Cuban cautioned potential investors about jumping in on the bandwagon. He fired off a series of tweets that suggested folks temper their expectations for the cryptocurrency.

“Anyone anywhere can buy a stock,” Cuban wrote . “[C]rypto is like gold. More religion than asset. Except of course gold makes nice jewelry.” He told his followers at the time that he wasn’t questioning the value of Bitcoin but was questioning the “valuation” and said , “I think it’s in a bubble. I just don’t know when or how much it corrects.”

Cuban suggested that when everyone is “bragging about how easy they are making [money],” that it indicates there is a bubble happening.

While those who are more bullish on bitcoin have often dismissed the notion of a bubble, the growth of the cryptocurrency did stagnate in the weeks following Cuban’s comments. After hitting $3,000, the cryptocurrency dropped nearly $500 and hovered in the $2,500 range for the better part of the month.

Despite his trepidations about bitcoin and cryptocurrency in general, by the end of June, Cuban was set to partake in an initial coin offering (ICO) for an esports betting platform called Unikrn. At the time, Cuban acknowledged the approach was approaching unknown territory. He told CoinDesk at the time, "High risk. High reward."

Markets didn’t have much movement despite Cuban’s newfound involvement in cryptocurrency, but it appeared at the time that Cuban was willing to view cryptocurrency as a risky investment that could produce high returns.

Cuban went as far as to suggest in a video for Vanity Fair that bitcoin and Ethereum could be valid parts of a person’s investment portfolio—though the apparent endorsement came with some caveats.

First, Cuban noted that cryptocurrency is a high-risk investment. “It’s like collecting art, it’s like collecting baseball cards, it’s like collecting shoes. Something is worth what someone else will pay for it,” he said.

Still, the Dallas Mavericks owner was open to the idea of using cryptocurrencies as a volatile investment vehicle. “If you’re a true adventurer and you really want to throw the Hail Mary, you might take 10 percent and put it in Bitcoin or Ethereum,” he said. Cuban also cautioned, “If you do that, you’ve got to pretend you’ve already lost your money.”

At the time the video dropped, Bitcoin was in the midst of it massive climb to close the year. It had already shot up to well above the $5,000 mark and, shortly after Cuban’s comments, broke the $6,000 barrier and continued climbing to $7,000 by the following week. A person who invested in bitcoin the day the video with Cuban was released could have experienced a 230 percent return on investment by the time bitcoin reached its peak.

In December, as Bitcoin was reaching record highs and passing the $10,000 mark, Cuban again gave the okay to invest in cryptocurrency as long as it is done in moderation and viewed as a total risk.

In an interview with Money , Cuban said bitcoin is “still very much a gamble,” and noted, “it could go to $15,000 or zero and maybe both on the same day.” He also said he owned some Bitcoin and Ethereum—though risks become much more palatable with a net worth in the $3 billion range.

Just days after Cuban’s comments, bitcoin experienced its craziest climb yet, jumping from around $12,000 to above $18,000 in just two days. The cryptocurrency experienced a slight correction after that, but returned to its climb and hit its record high of $19,783 just two weeks after Cuban gave his take.

Showing just have far Cuban has come on bitcoin and cryptocurrency, he announced earlier this week that his Dallas Mavericks will accept bitcoin and Ethereum as a method to pay for tickets starting next season. Even if the tech investor doesn’t fully believe in cryptocurrency, he’s clearly willing to try to profit off it—an approach that likely helped him become such a success in the first place.