[7] After graduating from Middlebury, between 2000 and 2004, Arison moved to Washington D.C. to pursue a career in politics, founding a think tank focused on building democracy in his home country of Georgia.

"[12] In 2014, Arison secured a $23.8 million investment, primarily from chief investors DFJ and Highland Capital Partners, as well as SV Angel and Great Oaks VC, along with individuals like Lars Rasmussen of Google Maps and Hans Robertson of Meraki.

The investment's purpose was to expand the company's services beyond Silicon Valley and Los Angeles to compete with market leaders like Carmax and Craigslist.

"[13] Between 2017 & 2018 BMW iVentures, Alliance Ventures, and Lithia Motors participated in multiple rounds of investment (Series C & D) which brought together $178 million in equity and debt.

[17] In May 2016, when Donald Trump was criticized for his policies by businesspeople in Silicon Valley, Arison was included, saying, "We all very strongly believe in immigration and bringing very skilled, awesome people to the U.S. and welcoming them.

[21] In 2020, Arison also publicly supported the CARES Act, considering it "a huge win for small business owners" during the coronavirus pandemic.

[25] On October of 2022, Arison faced backlash for Tweets that resurfaced where he showed support for conservative politicians who have diminished rights of the LGBTQ+ community such as Donald Trump and Virginia Governor Glenn Youngkin.