The Best of SBS: Pod Save America's Jon Lovett & Tommy Vietor

Key Takeaways

Jon Lovett's career evolved from comedy and speechwriting to media entrepreneurship, driven by a need for validation.
Crooked Media was founded post-2016 election to create a pro-democracy, activist-oriented media platform.
Effective speechwriting requires broad competency, political understanding, and the ability to synthesize viewpoints.
Founding a media company with friends brought challenges in management and balancing personal and professional roles.
Personal growth, self-acceptance, and external support are crucial for overcoming insecurities and managing a 'noisy mind'.
Balancing demanding political and media careers with family life presents significant challenges and requires strong support systems.
Addressing societal issues like gun violence, climate change, and fertility struggles shapes perspectives on parenthood and advocacy.
Discomfort with traditional management and a desire to speak freely motivated a shift from established media to independent ventures.

Jon Lovett withdrew from the University of Chicago Law School due to a lack of genuine desire to attend, citing a haphazard and intuitive choice.
His early career, including stand-up comedy and political volunteer work, led to speechwriting for Hillary Clinton.
Lovett attributed past insecurity and pursuit of external validation to his upbringing in a career-driven Long Island environment.
A career path driven by the need for validation led to easy pursuit of activities where competence was recognized, avoiding alternative directions.

Leveraging experience writing comedy for President Obama's White House Correspondents' Dinners provided credibility for a blind script deal in Los Angeles.
Speechwriting demands broad competency, including political understanding, writing skills, synthesizing inputs, and adopting another's voice.
Shortly after moving to Los Angeles, a White House-themed show pitch developed with Josh Gadd and Jason Weiner was picked up by NBC, leading to rapid pilot production.
Lovett admits to feeling like an imposter at 24 as a speechwriter for Hillary Clinton and later navigating a new field in Los Angeles.

The founding of Crooked Media was a major career risk post-2016 election, stemming from a desire to not return to previous jobs.
The company was formed with an urgent feeling to create a pro-democracy media entity, intertwining activism with media, and avoiding dishonest propaganda.
With some financial flexibility, the founders had about six months to develop Crooked Media, aiming for active participation over passive observation in democracy.
One guest stated anger, not hope, as a primary motivator, finding it led to bravery and more interesting work, and critiqued the punditry shift from participation to observation.

A guest reflected on their 'noisy mind' as a source of curiosity, driving a varied career in math, politics, television, and media.
The guest acknowledged a price paid for this curiosity, citing difficulty in maintaining focus that impacted a television pilot project.
The discussion touched on the desire for a more serene experience with one's own thoughts and career path.
The guest expressed gratitude for their current role, where comedy, writing, and political speechwriting experience coalesce, despite acknowledged stress.

External relationships and support systems are critical for personal growth and self-kindness, especially in overcoming insecurities and blind spots.
One guest found that a relationship and therapy helped address persistent body image issues and self-loathing.
Losing weight with medication does not eliminate self-criticism, suggesting it helps but doesn't solve underlying issues.
A guest estimated a potential net reduction in overall self-criticism if body image criticism is lowered by 50%.

A guest questioned whether the drive to juggle multiple responsibilities at Crooked Media allows for emotional gratitude, suggesting it could be unhealthy or arrogant.
The preference is for feelings of responsibility towards the team and ensuring work validates others, rather than focusing on personal achievement.
Joy is found in executing tasks well and contributing to a shared, positive work environment.
The discussion clarified that the concern was about a mindset leading to unhealthy self-reflection, differentiating it from ego versus gratitude in work.

Tommy Vietor's journey into politics led to a White House role in national security and foreign policy after an internship attempt for Ted Kennedy.
Running a media company with friends is a 'different thing' than focusing solely on politics, with management becoming a full-time job with around 50 employees.
The urgency to go 'all in' with Crooked Media full-time in early 2017 was driven by the 2016 US Presidential election outcome and the belief their work was too important for a hobby.
The goal for Crooked Media was to use humor, inspiration, and facts to empower people to act on issues, countering cynicism that benefits demagogues.

A guest described their positive experience on the National Security Council, noting a dedicated team of non-political, career officials who served selflessly.
The host reflected on the crucial support of his wife in making significant career changes, including leaving ESPN and starting a business.
One guest's decision to co-found Crooked Media was initially viewed as unconventional by his wife and others.
Familial reactions to career choices highlighted personal sacrifices, with one guest's father disapproving of a writing career over engineering.

One guest's wife was a reason he left his White House role in 2013, as he felt unable to focus on their relationship.
Balancing demanding work with family life is difficult, especially the desire to leave work on time to see a young child, contrasting with long hours in past political jobs.
Initial fears about audience retention for Crooked Media included subscriber counts dropping to zero after the 2016 election and ongoing imposter syndrome.
The decision to create Crooked Media stemmed from guilt about leaving politics during a critical time and a desire to improve discourse.

One speaker's focus has been racial equality and basic human decency, leading to political labels and criticism despite a non-partisan view.
Guests expressed fears about the future, citing gun violence, mass shootings, and climate change as significant concerns impacting their desire to raise children in America.
A guest described a shift in perspective after the birth of his daughter, moving from apprehension about infants to cherishing time with his child.
The guests publicly shared struggles with miscarriage and fertility, including the stillbirth of a daughter, to destigmatize these issues and foster empathy.