Joe Ricketts let it be known that he wanted his children to establish themselves through their own hard work and would not be allowed to join TD Ameritrade until they reached the age of 30.

After acquiring the Tribune, Zell announced that he would sell the Cubs and related entities including Wrigley Field and a 25% share of SportsNet Chicago.

[16][18] Under bankruptcy protection, the sale of the Cubs and the 25% interest in SportsNet Chicago would raise needed funds for the ailing Tribune company.

Later, Tom and his brother Pete lived in an apartment over the "Sports Corner" at Addison and Sheffield, across the street from Wrigley Field.

In 2014, the nearly $1 billion renovation project of Wrigley Field and the collateral land finally broke ground after winning city approval.

[25] On Opening Day of the 2017 season, with Cubs fans celebrating its first in a century role as the defending world champions of baseball, the Ricketts family delivered The Park at Wrigley.

Chairman Tom Ricketts, president of business operations Crane Kenney, Chicago Mayor Rahm Emanuel, numerous elected officials, neighbors and community leaders cut the ribbon at the Park at Wrigley.

[26] On March 30, the Ricketts family opened their first hotel, located on Clark Street, across from the front entrance of Wrigley Field.

[5] Ricketts spent one summer early in life working at TD Ameritrade, giving customers stock quotes over the phone.

[5] Ricketts is credited with pioneering the idea of using the Internet and other technologies to help companies sell their investment-grade bonds directly to retail investors, as opposed to limiting sales only to institutions.

[32] Forbes describes the company as a "technologically-oriented investment bank focused exclusively on the underwriting and distribution of fixed income products to individual investors.

"[5] In February 2021, Incapital announced it was merging with 280 CapMarkets to create a new fintech, InspereX, with a mission of "improving fixed income distribution and trading for all market participants.