Podcast Summary: The Dan Le Batard Show with Stugotz Episode: South Beach Sessions - Jon Lovett
Release Date: May 1, 2025

Introduction

In this insightful episode of South Beach Sessions, hosts Dan Le Batard and Stugotz engage in a profound conversation with Tommy Vietor and Jon Lovett. The discussion delves into Tommy's multifaceted career, his transition from mathematics and politics to media and comedy, the founding and growth of Crooked Media, and the personal challenges he has navigated along the way.

Tommy Vietor’s Early Years and Academic Pursuits

Tommy Vietor begins by reflecting on his academic background, emphasizing his deep connection with mathematics and its influence on his critical thinking skills.

• Mathematics and Critical Thinking:
  [02:21] Tommy shares, “With math, you can't fake it, and you almost can't get it. You either get it or you don't.” He credits mathematics with making him a "more critical and precise thinker."

• Struggles with Society's Approach to Math Education:
  [05:25] Tommy criticizes the traditional math curriculum, stating, “Every school is getting it wrong.” He advocates for a more engaging and enjoyable approach to teaching math, believing it would lead to a smarter and more satisfied society.

Transition to Politics and Media

Tommy recounts his journey from academia to the political arena, highlighting the serendipitous nature of his career path.

• Venturing into Politics:
  [07:13] After graduating from Williams College, Tommy moved to New York, juggling odd jobs while exploring interests in stand-up comedy and politics. His involvement with the Kerry campaign in 2004 marked his initial foray into the political world.

• Becoming a Speechwriter:
  [08:46] Tommy describes how writing jokes for Hillary Clinton led to a junior speechwriter position. He reflects on the rapid shift from deciding against law school to embracing a career in political speechwriting.

From Speechwriting to Media Entrepreneurship

Tommy details his pivotal decision to leave politics for media and comedy, culminating in the creation of Crooked Media.

• Risk and Opportunity:
  [14:03] Transitioning from a stable job as a speechwriter for Obama, Tommy took a significant risk by moving to Los Angeles to pursue comedy writing without a clear plan. He shares, “I had to get out before I turned 30,” highlighting the urgency behind his career shift.

• Early Media Projects:
  [15:48] Upon arriving in LA, Tommy quickly engaged in media projects, including developing the pilot for 1600 Penn. Despite initial overwhelm and challenges, he successfully navigated the complexities of TV writing.

• Founding Crooked Media:
  [27:08] In the aftermath of Donald Trump's election, Tommy and his colleagues felt compelled to create a proactive media platform. Crooked Media was born out of a desire to support democracy and engage actively rather than passively observing political shifts.

  • Mission and Values:
    [28:04] Tommy articulates Crooked Media’s mission: “We believe democracy is under attack right now. We are a pro-democracy media company, unabashed in that point of view.”

  • Lean Startup Approach:
    [49:26] Emphasizing financial prudence, Tommy explains, “We never had to take investment, which meant we never had debt or shareholders breathing down our neck.” This approach allowed Crooked Media to grow organically and maintain control over its mission and values.

Challenges of Scaling and Maintaining Friendships

As Crooked Media expanded, Tommy discusses the complexities of maintaining personal relationships and company culture.

• Balancing Friendship and Business:
  [54:19] Tommy acknowledges the challenges of working closely with friends, noting, “If you spend all day working with somebody, you've seen them all day, it's different.” He emphasizes the importance of open communication and trust to navigate these dynamics.

• Managing Rapid Growth:
  [58:05] Scaling the company from a small team to over 100 employees introduced new operational challenges. Tommy highlights the difficulty in maintaining the company's voice and ensuring consistent quality across a growing number of shows and platforms.

• Unionization Efforts:
  [73:31] The podcast touches on negotiating unionization, a testament to Crooked Media’s evolution and commitment to employee welfare. Tommy reflects on the importance of building a collaborative and trusting culture during rapid expansion.

Personal Reflections and Mental Health

Tommy opens up about his personal struggles and growth, offering a candid look into the mental toll of his career transitions.

• Dealing with Insecurity and Validation:
  [07:13] Tommy admits that his early career decisions were driven by insecurity and a desire for external validation. Over time, he learned to align his career choices more closely with his passions rather than seeking approval.

• Impact of the Pandemic:
  [39:38] The pandemic served as a turning point for Tommy, prompting significant personal changes. He shares his experience with depression and how it led him to prioritize what he wanted to be doing over what he wanted to be.

• Balancing a Noisy Mind:
  [34:34] Tommy describes himself as having a "noisy mind," which fuels his curiosity and diverse career path but also presents challenges in maintaining focus and managing personal well-being.

Maintaining Company Identity and Vision

Tommy discusses strategies for preserving Crooked Media’s mission amid growth and diversification.

• Ensuring Consistency and Creativity:
  [60:28] As the company expanded, Tommy emphasized the importance of maintaining a consistent voice while also allowing creative input from new talent. He believes in balancing conformity with consistency to uphold the company's core values.

• Hiring and Building Teams:
  [52:18] Tommy takes pride in Crooked Media’s hiring process, noting, “I've read a ton of material, and that was a group of people they’ve all gone on to be incredibly successful.” This selective process has been key to assembling a talented and cohesive team.

Conclusion

Tommy Vietor’s journey from a math enthusiast and political speechwriter to a media entrepreneur encapsulates the essence of adaptability and resilience. Through founding Crooked Media, he has leveraged his diverse skill set to create a platform dedicated to pro-democracy values, all while navigating the complexities of personal growth and professional scaling. His candid reflections on mental health and the challenges of maintaining personal relationships within a growing company offer valuable insights into the human side of entrepreneurship.

Notable Quotes:

• "With math, you can't fake it, and you almost can't get it. You either get it or you don't." — Tommy Vietor ([02:21])
• "We believe democracy is under attack right now. We are a pro-democracy media company, unabashed in that point of view." — Tommy Vietor ([28:04])
• "Anger is my motivation. I'm not a hope guy, I'm an anger guy." — Tommy Vietor ([31:00])

This comprehensive summary encapsulates the depth of the conversation, highlighting Tommy Vietor's professional trajectory, personal challenges, and the foundational values of Crooked Media. It provides listeners with a clear understanding of the key discussions and insights shared during the episode.