How Baseball Prepared Derek Jeter for Business | The Deal

Intro (00:00:00)

• Alex Rodriguez has known Derek Jeter for almost 30 years.
• Rodriguez describes Jeter as undefeated and a mystery.
• Jeter's experience in New York is of interest to Rodriguez.
• Jeter set his sights on business after baseball early on.

How Derek and Alex met (00:01:00)

• Rodriguez and Jeter first met when they were 18 and 17 respectively.
• They met at Mark Light stadium during a game between the University of Michigan and the University of Miami.
• Jeter had already signed with the Yankees while Rodriguez was in the upcoming draft and had signed with the University of Miami.
• Rodriguez and Jeter had spoken on the phone prior to meeting.
• Back then, young athletes did not have social media to follow each other.
• Rodriguez was impressed by Jeter's accomplishments despite playing in a shorter season in Kalamazoo.

Derek's Early Days with the Yankees (00:03:16)

• Derek Jeter, a former professional baseball player, played for the New York Yankees and later became a successful businessman.
• Drafted by the Yankees in 1992, Jeter had signed a scholarship to attend the University of Michigan but chose to play for the Yankees after they agreed to pay for his college education.
• Jeter joined the Yankees in 1995, during a period when the team had not won a World Series since 1978, and the expectations for the team were high due to its past success.
• Despite the pressure, Jeter and his teammates focused on keeping their jobs and staying in the major leagues rather than feeling overwhelmed by the expectations.

Playing in New York & Arbitration (00:07:45)

• Derek Jeter and Alex Rodriguez discussed their early careers in baseball and their thoughts on the sport's popularity in the 1990s.
• Jeter believed baseball was the most popular sport in the country at the time due to its widespread participation and accessibility.
• Jeter and Rodriguez agreed that the success of big-market teams like the New York Yankees, Boston Red Sox, Los Angeles Dodgers, and Chicago Cubs is beneficial for baseball's overall health.
• During arbitration, Jeter gained insight into the business side of baseball and how others perceived his performance, which helped him develop a thicker skin for future contract negotiations.

George Steinbrenner (00:12:15)

• Derek Jeter and Alex Rodriguez had long-term deals with the New York Yankees, which allowed them to negotiate successfully with the team.
• George Steinbrenner, the owner of the Yankees, was a demanding and passionate leader who expected excellence from his players and the team.
• Jeter and Steinbrenner had a close relationship, with Jeter providing valuable input on various matters, including player personnel decisions.
• Jeter learned valuable lessons from his teammate Luis Sojo, who emphasized the importance of always striving for two outs, taking risks, and having fun while working hard.

Alex Comes to New York to Play Third Base (00:17:18)

• Alex Rodriguez (A-Rod) and Derek Jeter were keeping in touch and playing against each other during the nineties.
• When A-Rod signed with the New York Yankees, he agreed to play as a third baseman, despite being a shortstop.
• A-Rod never asked to play shortstop and was committed to playing third base.
• Tom Hicks, the owner of the Texas Rangers, needed to move some contracts due to financial issues and traded A-Rod.
• A-Rod suggested the Red Sox, Angels, and Mets as potential teams.
• A-Rod was interested in joining the Mets because he grew up watching Magic Johnson and Larry Bird and wanted to be in New York with Derek Jeter.
• The Red Sox deal fell apart at the last minute.
• At the MVP dinner, Yankees General Manager Brian Cashman suggested that A-Rod move to third base, and A-Rod agreed after having three vodka cocktails.
• The deal happened quickly within 10 days.

2009 World Series Championship (00:19:41)

• Winning the 2009 World Series was a lot of hard work and relief for Derek Jeter and his teammates.
• Jeter felt validated and thankful for achieving his dream of winning a championship.
• The team did not want to be remembered as lucky for winning four championships in their first five years and then not winning again.
• The constant reminder of not winning in New York created a desire to win again.
• New York is a hotspot for business and entertainment.
• Winning in New York elevates everyone involved.
• Playing at Yankee Stadium is like performing in a Broadway play, with brighter lights and celebrity attention.
• Celebrities show up to watch the Yankees play because they win.

Derek's thoughts on media (00:23:00)

• Derek Jeter reflects on his career and the opportunity he had to play in New York City, the biggest market in the world, while maintaining a relatively private personal life.
• He mentions his struggles with the media and how he learned from Derek Jeter's advice to "make contact" and "not tell them anything."
• Jeter explains his belief in keeping his private life separate from his public persona and career, as he felt it could lead to unwanted attention and distractions.
• He understood that he didn't need the media to do his job and that his performance on the field would speak for itself.
• Jeter had a policy of addressing issues once and then moving on, avoiding further discussion that could prolong the story.

Derek joins Jordan Brand (00:25:31)

• Derek Jeter joined Jordan Brand and received valuable advice from Michael Jordan.
• Jeter regrets not listening to Jordan's advice, which negatively impacted him.
• Jeter gained a deeper appreciation for Derek Jeter's greatness as a person after his playing career.
• Jeter wanted conversations at the stadium to be focused on the game.
• Jeter first met Michael Jordan in 1994 during the Arizona fall league.
• Jeter developed a close relationship with Jordan, who became a mentor and big brother to him.
• Jordan and Magic Johnson were among the first athletes to successfully transition their on-court abilities into business success.
• Jeter was invited by Jordan to join the Jordan Brand as the first baseball player.
• Jeter didn't perceive it as a risk to join Jordan Brand due to Jordan's reputation and the cool factor associated with him.

Derek's decision to retire (00:28:55)

• Derek Jeter decided to retire from baseball after breaking his ankle twice and missing the previous year.
• He wanted to have one more healthy season and announced his retirement before the season started to avoid constant questions from teammates and the media.
• After 20 years in New York, Jeter felt physically and mentally exhausted and ready to move on from his baseball career.

Business after baseball (00:30:35)

• Jeter started preparing for his post-playing career years in advance, driven by a fear of being unprepared.
• He gained experience in various aspects of running an organization, including contract negotiations, marketing, philanthropy, and player development.
• Jeter launched The Players Tribune, a company focused on athlete empowerment, shortly after his retirement.

Derek's reflection on the Miami Marlins (00:32:00)

• Derek Jeter's experience as a player prepared him for the challenges of being the CEO and owner of the Miami Marlins.
• The most difficult aspect of being CEO was exercising patience while waiting for his efforts to turn the organization around to yield results.
• Jeter focused on building trust with his employees and players by spending time getting to know them and understanding their roles. He also prioritized diversity in his front office, providing opportunities to deserving individuals.
• Jeter learned from his mistakes and is confident in his ability to succeed in future endeavors, regardless of the market size.
• Jeter is open to returning to baseball but only if he has a controlling ownership stake.
• Jeter enjoys investing and meeting new people with great ideas. When considering investment opportunities, he prioritizes investing in people he knows and trusts who are passionate about their work.

35:25.Investment philosophy (00:37:36)

• Derek Jeter joined the commentary team for the World Series because he loves baseball and wanted to help promote the sport.
• Jeter believes baseball has lagged behind other sports in terms of rule changes and entertainment value but credits recent rule changes for helping to bring about a rebound in the sport's popularity.
• Jeter is enjoying his new role as a commentator and is committed to improving his skills.
• Jeter and Alex Rodriguez have a history but have put it behind them and are now working together successfully.

Derek's future & legacy (00:44:07)

• Derek Jeter's only concern is being remembered as a Yankee.
• He wants to be remembered as a good teammate and a winner.
• Jeter emphasizes the importance of being present for his family and supporting his children's passions.