Podcast Summary: "The Onion’s Owner on Satire, Infowars, Defending Democracy & Trump"

Podcast Information:

• Title: On with Kara Swisher
• Host: Kara Swisher, Vox Media
• Episode Title: The Onion’s Owner on Satire, Infowars, Defending Democracy & Trump
• Release Date: April 7, 2025

In this compelling episode of On with Kara Swisher, Kara engages in an in-depth conversation with Jeff Lawson, the owner of The Onion, co-founder and former CEO of Twilio, and co-founder of Democracy First, a political action committee (PAC) dedicated to supporting democratic candidates across party lines. The discussion delves into Lawson's entrepreneurial journey, his motivations behind acquiring The Onion, his efforts in defending democracy, and his perspectives on the current political and media landscape.

1. Jeff Lawson's Entrepreneurial Journey

Early Ventures and Twilio: Jeff Lawson recounts his early entrepreneurial endeavors, including his first startup, Versity, which aimed to digitize lecture notes—a precursor to modern online note-sharing platforms. Reflecting on this venture, Lawson shares:

"We could have had any domain name we wanted… Number four free. Which then later turned into versity.com, but it was this excuse to start playing with the Internet." (03:45)

Despite initial success and raising venture capital, Versity eventually succumbed to competition and market challenges, teaching Lawson invaluable lessons about the volatile nature of startups.

Transitioning to Twilio in 2008, Lawson describes how the company became a frontrunner in cloud communications, positioning itself as essential infrastructure for developers to integrate communication features into their applications. He credits timing and luck for Twilio's meteoric rise, especially during the mobile boom.

Twilio's Success and Departure: Twilio reached a valuation peak of approximately $70 billion during the pandemic. However, internal conflicts with activist investors led to Lawson stepping down as CEO and board member in January 2024. Reflecting on his departure, Lawson admits:

"It was wartime. You know, when an activist is at the gates, that for a board is wartime… And I wasn't doing that. And as a result, we had this moment where push came to shove…" (08:03)

This experience reshaped his approach to leadership and governance within startups.

2. Current Endeavors: Founder's Garage and Democracy First PAC

Founder's Garage: Post-Twilio, Lawson established Founder's Garage, a mentorship hub for early-stage startups. Partnering with notable entities like Bessemer, Y Combinator, and OpenAI, Founder's Garage provides aspiring entrepreneurs with guidance and resources without the immediate pressure to launch new ventures.

"I just was like, can I do this? That was kind of fun… Surrounding myself with interesting people doing interesting things… that's a much better way to spend my days." (11:12)

Democracy First PAC: In response to growing threats to democratic norms, Lawson co-founded Democracy First in 2022. The PAC focuses on supporting candidates committed to upholding democracy, particularly at the state and local levels where election integrity is most vulnerable. Discussing the PAC’s mission, Lawson emphasizes:

"We're gonna work really hard in a bipartisan way just to make sure that the people who believe in rule of law are gonna sit in these seats when the election comes around." (16:59)

Lawson highlights the challenges posed by external influences and big-money campaigns, advocating for grassroots efforts to preserve democratic institutions.

3. Influence of Big Money in Politics

Big Money and Election Integrity: Lawson critically examines the impact of wealthy individuals like Elon Musk on political races, particularly referencing the Wisconsin Supreme Court case where Musk’s substantial financial support for Susan Crawford was ultimately unsuccessful. He reflects:

"What's happening is people don’t want to be thought of as just pawns that can be bought for a price… enough people believe that this is just, it's not what America's about." (19:56)

He argues that such overt financial interventions are politically toxic and undermine the foundational principles of democracy:

"Politically toxic, yes." (19:55)

Consequences for Business Leaders: Lawson discusses the dilemma faced by tech CEOs who feel pressured to align with political figures, potentially compromising their company's values and integrity. He underscores the tension between fiduciary responsibilities to shareholders and personal civic duties.

4. Acquisition of The Onion

Reasons for Buying The Onion: Initially approached as a humorous match in proportional market caps compared to other media acquisitions like Bezos’s Washington Post, Lawson’s acquisition of The Onion evolved into a mission to save the satirical publication from private equity's cash-extraction approach.

"The reason for buying… it's saving the Onion because it was in a death spiral." (37:10)

Shift to a Membership Model: Under Lawson’s ownership, The Onion transitioned from ad-driven revenue to a subscription-based model, focusing on quality content and reader engagement. He notes:

"Almost entirely now… subscription revenue from memberships." (43:01)

This strategic pivot aims to ensure financial sustainability while preserving the publication’s comedic integrity.

5. The Role of Satire in Democracy

Satire as a Truth-Telling Mechanism: Lawson champions satire as a powerful tool for societal reflection and truth-telling. He explains:

"Satire is for the truth. You wrap the truth in this pill, in this pill pack, and now someone can… you get it inside of people’s head." (40:35)

The Onion serves as a satirical mirror, reflecting and critiquing political and social dynamics in a manner that pure journalism often cannot.

Attempt to Acquire Infowars: In a bold move, Lawson attempted to purchase Alex Jones’s Infowars at a bankruptcy auction, intending to transform it into a satirical platform. However, the bid was rejected by a federal bankruptcy judge. Discussing this endeavor, Lawson states:

"We did it because, as a stunt… The Infowars brand because it stands for exactly like the worst of the Internet." (47:27)

This attempt underscores his commitment to countering misinformation through humor and satire.

6. University of Michigan and DEI Initiatives

Challenges with DEI Programs: Lawson addresses the controversies surrounding Diversity, Equity, and Inclusion (DEI) initiatives at universities, particularly the University of Michigan. He reflects on the difficulties in implementing equity-focused programs without alienating allies:

"Equity means someone gets something and I don't get something or vice versa… that's where it gets really complicated." (54:14)

He advocates for a more inclusive approach that emphasizes diversity and inclusion without overcomplicating equity, aiming to maintain broad support across different demographics.

Strategy for Managing DEI During Political Upheaval: In light of political pressures and potential funding cuts threatening DEI programs, Lawson suggests:

"It would be okay to admit that equity is a really hard concept for a society to get right… Diversity, inclusion. Diversity, inclusion. Diversity, inclusion. Diversity." (54:14)

He emphasizes the importance of refining DEI strategies to foster genuine inclusion without triggering backlash.

7. Conclusion and Future Outlook

Protecting Satire in a Polarized Climate: As the conversation wraps up, Lawson expresses commitment to defending The Onion against potential threats, including hypothetical scenarios where the publication might be targeted under authoritarian regimes:

"We have a job to do, which is to cut through and deliver truth as best we can to people… We have to do this… that's our calling." (60:25)

He underscores the essential role of satire in maintaining a resilient and reflective society, committed to upholding democratic values through humor and critical commentary.

Notable Quotes with Timestamps:

• Jeff Lawson on Starting a Company:

  "I'm gonna start a company in order to just have an excuse to go play with this new thing called the Internet." (04:47)

• Lawson Reflecting on Twilio Departure:

  "I had every title imaginable to avoid this outcome. So somehow I screwed up." (09:37)

• On Twilio's Role:

  "Twilio is infrastructure that software developers use to embed communications ins, the apps that you have on your phones and use on the web." (09:48)

• On Big Money Influencing Elections:

  "If we need to develop new properties that are going to be relevant to today's generation… Infowars… represents that the worst of the Internet." (47:17)

• On The Onion's Mission:

  "We are not resistance media. We just need to call out bullshit when we see bullshit." (40:58)

Final Thoughts: This episode provides a multifaceted exploration of Jeff Lawson's perspectives on entrepreneurship, media ownership, political influence, and the role of satire in modern democracy. His insights offer valuable reflections on navigating the complexities of maintaining democratic integrity and fostering meaningful societal discourse in an increasingly polarized world.