The Pitfalls of Mistaking Digital Ads for Digital Organizing
For nearly a decade, many progressives have operated under a faulty assumption: that running digital ads and short-term voter engagement campaigns on social media would organically translate into long-term political influence. On paper, the notion sounded logical: meet voters where they spend their time online, run sharply targeted ads, and drive up voter registration or turnout. In practice, however, these efforts often ended up funneling millions of dollars into Big Tech platforms. Those very platforms, in turn, sometimes funneled profits toward political donations benefiting conservative candidates or padded the compensation packages of executives, many of whom maintained cozy relationships with right-wing donors.
This cycle was, and remains, self-defeating. Progressives poured resources into Silicon Valley ad buys, and Silicon Valley CEOs maintained or extended their influence by donating to conservative politicians. Despite all these ad campaigns, they rarely built the kind of long-term, relationship-based community necessary to shift public opinion. Meanwhile, the media landscape evolved: while progressives were busy perfecting 30-second spots, the right was pioneering a relentless, long-form approach to content that resonates with millions of viewers, particularly young and male audiences.
The Rise of Long-Form Influencers and Podcasters
One of the most striking observations the progressive left has made since Donald Trump was sworn in for his second term is how dramatically our media ecosystem has shifted toward digital influencers, particularly podcasters and YouTubers with massive, male-dominated followings. But for young men like myself, this is not necessarily shocking. What used to be written off as “alternative” media, fringe talk shows, gaming streams, and edgy comedy channels now seem not only mainstream but are being pushed upon young men in their algorithms and have become pivotal in deciding political outcomes. This reality should be unsettling and clarifying for progressive organizations. It’s unsettling because the urgent, progressive vision many of us champion gets drowned out by hours of unfiltered conversation, where conservative or even alt-right ideologies slip in under the guise of casual banter. We can no longer pretend traditional 30-second ads and sporadic mobilizations will suffice. The right has embedded itself in these digital communities, day in and day out, and that’s a form of deep base-building we’ve mostly failed to replicate.
The data underscores the magnitude of this shift. Earlier this year, Bloomberg published a comprehensive analysis of nine popular YouTube and podcast channels that collectively interviewed Donald Trump before the 2024 election. Researchers dissected 2,000 videos and nearly 1,300 footage hours for recurring themes. Their findings were staggering: each channel skewed roughly 80% male, with frequent discussions on border security, inflation, transgender athletes, election integrity, and the “war” on masculinity. Trump’s appearances alone racked up about 113.6 million YouTube views. By contrast, Vice President Kamala Harris pursued a parallel podcast strategy, also speaking about election issues, but tallied only about 6.8 million total YouTube views. That’s a difference of more than 100 million, a gap too large to dismiss as a mere curiosity. It reveals a fundamental failure: progressives still aren’t inserting themselves consistently and authentically into the massive digital subcultures that shape public opinion.
Platform algorithms on YouTube, Twitch, and TikTok often push viewers deeper into related content once they show an interest in these conservative or anti-establishment narratives. This “rabbit hole” effect can intensify exposure to more extreme ideologies, turning casual viewers into committed followers. Recognizing how automated recommendations amplify right-wing messaging is key to understanding the scale of this recruitment machine.

Right-Wing Influencers: From Comedy to Culture War
It’s not just that the right dominates social media; they’ve mastered the art of transforming edgy commentary, gaming streams, and comedic banter into potent political messaging. Conservative hosts weave jokes about “woke culture” and “Big Pharma” seamlessly into calls to vote Republican. They foster parasocial relationships with listeners who spend hours each week tuning in, cultivating an “us vs. them” identity that can overpower any progressive message squeezed into a 30-second ad.
Recent data compiled by Bloomberg underscores that these messages aren’t just random, off-the-cuff remarks:
37% of top-performing conservative videos (over 1 million views) explicitly mentioned voting or elections.
50% cast doubt on the integrity of the democratic process.
33% talked about war, framing Trump as a “peacekeeper.”
29% disparaged transgender identity, especially around minors and sports.
Gaming subcultures, eSports tournaments, and Discord servers now host vast communities that are young and predominantly male—prime targets for conservative commentators. These influencers don’t just talk about gaming; they embed themselves in these spaces daily, seamlessly blending strategy tips or comedic banter with right-wing talking points. That ongoing presence fosters a sense of camaraderie that traditional campaign ads can rarely achieve.
This mixture of cultural commentary and politicized tropes stokes anxiety about economic decline, masculinity, or “overreaching” social progress. It then provides a neat solution: “Vote with us, stand against this tide.” Viewers aren’t just backing a set of policies; they’re joining a community. The casual, conversational style of podcasting further cement these bonds, making the audience feel personally connected to the host and the broader movement.
Through humor, memes, and offhand remarks, conservative voices normalize their viewpoints as part of everyday entertainment. By framing issues as fun, edgy, or countercultural—rather than overtly political—they lower the barrier to acceptance. This blend of pop culture and ideology makes it easy for audiences to internalize conservative beliefs without feeling they’ve made a drastic shift.
Conservative personalities, however, don’t stop at podcast monologues or social media chatter. They create expansive digital ecosystems designed to funnel online audiences into offline events, reinforcing and growing their base. Charlie Kirk’s Turning Point USA (TPUSA) epitomizes this hybrid approach. The organization boasts more than 3,500 high school and college chapters, positioning itself as a “fun,” irreverent outlet for “American ideals.” These chapters serve as on-the-ground hubs where conservative activism can flourish, turning enthusiastic members into micro-influencers who extend the online conversation into their everyday social circles.
Simultaneously, TPUSA has launched multiple original shows, building the brand of figures like Candace Owens, who supply a steady stream of content and keep viewers engaged well beyond election cycles. In tandem, large-scale events and conferences like the Young Women’s Leadership Summit, America Fest, and the Student Action Summit offer face-to-face connections. Attendees and speakers generate hours of viral video clips, fueling further online engagement and solidifying the organization’s digital footprint.
Beyond high-profile figures, many smaller conservative groups and far-right communities flourish on Reddit, “alt” social sites, and Discord servers tied to pop culture. Each micro-community reinforces the others through shared events, memes, and interlinked chat groups. This decentralized web can be just as potent in sustaining long-term loyalty and driving grassroots activism.
In essence, TPUSA’s model demonstrates the power of intertwining irreverent digital messaging with tangible, real-world community-building. Memes and podcasts alone can capture short-term attention, but the combination of these mediums with in-person chapters and national events creates a robust pipeline for recruiting and retaining conservative activists. It’s a strategy that has proven difficult for progressives to match, given the left’s tendency to invest heavily in short bursts of digital advertising rather than sustained, multi-platform organizing.
Below is a snapshot of some of the most influential creators across various social platforms, illustrating the tremendous reach right-leaning figures have cultivated. The size of their followings highlights just how effectively conservative content penetrates these digital subcultures, especially among younger, more male-dominated audiences. Meanwhile, the left’s footprint remains comparatively smaller, underscoring a critical gap in sustained progressive engagement.

The “Newsom vs. Charlie Kirk” Podcast Example
A recent high-profile crossover illustrates these dynamics perfectly. Charlie Kirk, the conservative commentator, appeared as a guest on Governor Gavin Newsom’s newly launched podcast, This is Gavin Newsom. Their conversation, which touched on policy debates and social issues, was later clipped and shared by both sides. Newsom posted some of the highlights to his own TikTok account, where they collectively drew around 1.2 million views by March 9, 2025. Meanwhile, Kirk’s channel carved out roughly 15 different excerpts from the same interview, tallying more than 22 million views, before even counting the secondary wave of right-wing outlets that re-posted and reframed the content.
Though the discussion was wide-ranging, conservative media almost unanimously spun it as further evidence of “liberal mismanagement.” The sheer difference in reach, 1.2 million versus 22 million, spotlights how effectively right-wing platforms amplify their own narratives, creating an echo chamber that dwarfs the reach of many progressive efforts.
In a startling twist, Newsom used his platform to criticize a key position within his own party, the acceptance of transgender athletes in women’s sports, calling it “deeply unfair.” A New York Times/Ipsos poll from early January showed that 79 percent of respondents do not believe transgender female athletes should be allowed to compete in women’s sports. Even among Democrats, 67 percent opposed it, compared to 94 percent of Republicans and 64 percent of independents, based on a survey of 2,128 people with a margin of error of plus or minus 2.6 percentage points. Although this data indicates limited support for transgender inclusion across the broader electorate, this has been a huge issue for many of the grassroots organizing groups around the country working to protect and expand Trans inclusion and equity. Abandoning the issue so openly appears aimed at reaching the vast right-wing audience that conservative media and digital influencers have cultivated. With the 2028 presidential race looming and growing speculation that he will run, this shift is likely a preview of similar rhetorical pivots we’ll see from other Democratic hopefuls, especially as they navigate a digital landscape still shaped by conservative platforms. By taking this stance, Newsom risks sacrificing a core progressive constituency to a media ecosystem eager to exploit any sign of weakness or division within the left.
How the Left Can Compete
These insights bring us back to the left’s prevalent misunderstanding of “digital organizing.” Much of it has been glorified advertising, with money thrown at tech giants that eventually donate to the political opposition. That’s simply not the intentional, relationship-driven work required to build robust communities and shift worldviews.
By contrast, the right has excelled at forging irreverent, relatable communities anchored in humor and cultural commentary, then layering in political messaging. They operate year-round, not just in the months before an election. This slow but steady approach primes their audiences well before progressives show up with last-minute ads. In many ways, the right is playing chess, while the left often resorts to checkers.
Many viewers start out watching gaming or comedy streams for pure entertainment but gradually get exposed to conservative talking points, forming a subtle “recruitment pipeline.” Over time, casual jokes or memes can evolve into firm political stances, culminating in deeper advocacy and activism. Recognizing this progression explains how a hobby can become a gateway to long-term ideological alignment.
The good news is that we have all the ingredients to build compelling, culturally resonant brands, and they don’t have to reinvent the wheel. We can learn from the right’s blueprint of fusing entertainment, community-building, and politics into a year-round endeavor rather than a seasonal ad blitz. Instead of pouring funds into short-lived social media campaigns, we should focus on cultivating creators, platforms, and real-world convenings that embed progressive values into people’s everyday interests and routines.
Invest in Progressive Influencers and Content Creators
The first step is to systematically fund and nurture a new generation of progressive content creators, much like how the right supports voices who speak directly to gaming, fitness, financial, or lifestyle audiences. Research on digital subcultures shows that influencers who produce consistent, authentic content can rapidly foster trust and loyalty among niche audiences. Rather than relying on one-off, polished political ads, progressives should provide grants, sponsorships, or production resources to emerging creators, enabling them to make high-quality podcasts, YouTube series, and live streams. Crucially, supporting these influencers does not mean trying to micromanage their messaging or turn them into mouthpieces for a particular campaign. If they simply become another branch of a political brand, especially one with existing baggage, their credibility suffers. Instead, progressive funders must respect the creators’ independence, allowing them the creative freedom to shape organic, culturally relevant dialogue.
By providing aligned influencers with stable funding and the training to develop technical skills and sustainable revenue models, they can focus on shaping cultural and political dialogues in creative, often humorous, and decidedly human ways instead of scrambling for commercial sponsorships that might compromise authenticity.
In doing so, creators can spend their energy on innovative storytelling that builds real communities, rather than constantly seeking out brand deals. This approach ultimately fosters genuine, values-driven engagement that extends far beyond election cycles and into the core of how people consume media and form political opinions.
Build and Sustain Niche, Micro-Communities
Beyond supporting influencers, progressives should foster smaller, dedicated communities across platforms, Discord servers, Twitch chat rooms, and local meetups for people who share a passion for anything from sci-fi to sports. Numerous studies of online behavior, including those by the Pew Research Center, highlight that people are more receptive to political content when it’s integrated into topics they already care about. These micro-communities can evolve organically as members form genuine bonds, discuss pressing issues, and recruit new participants who share their interests. Over time, these groups become powerful echo chambers for progressive values, generating influence that extends far beyond sporadic campaign seasons.
Combine Online Spaces with Real-World Convenings
Even in our digitally driven era, face-to-face interaction remains a key catalyst for genuine community-building, especially for young people who lost formative social connections during the pandemic. While conservative groups have succeeded in blending campus tours, conferences, and daily online content, progressives lag behind when it comes to large-scale events that bring together students and grassroots activists. Despite some national gatherings for political staff, there is a striking absence of mass convenings for young activists and community leaders who want to connect with each other beyond the screen. Organizing local meetups, cultural festivals, or university events can fill that void, transforming online interactions into tangible, in-person relationships. Filming panel discussions, debates, or even casual hangouts and posting highlights on TikTok, YouTube, or Instagram Stories then creates a feedback loop, amplifying both the digital and real-world impact. By weaving these two spheres together, progressives can tap into the desire for belonging that many young people currently seek and build a more enduring, community-based movement in the process.
Produce Consistent Long-Form Content
To counter the right’s dominance in podcasts and extended YouTube interviews, progressive campaigns, and content hubs must prioritize depth, nuance, and regularity. Audiences are increasingly drawn to longer discussions that combine cultural commentary with policy insights. This format fosters stronger emotional ties between hosts and listeners, enabling podcasters and streamers to delve deeper into issues like income inequality, healthcare, and climate change—topics often too complex for 30-second ads. By releasing episodes or live streams on a predictable schedule, progressive channels can keep supporters engaged year-round, allowing for incremental shifts in public opinion rather than last-minute persuasion attempts during election season.
A Word on Costs
It’s important to underscore that building a robust digital media presence and fostering genuine community engagement is not cheap. The right invests heavily in production budgets, staffing, event planning, and the cultivation of influencer networks, and progressives must do the same if they hope to compete. Grassroots activism alone, while vital, cannot match the financial power needed to consistently create high-quality content, pay creators a living wage, and host large-scale events. If progressive donors, foundations, and political organizations genuinely want to shift the digital landscape, they have to commit significant resources over the long haul and target them toward sustainable community-building, not just headline-grabbing campaigns. Only with sustained, strategic funding can progressives build the robust, interconnected media ecosystem required to change cultural perceptions and drive lasting political impact.
Yet it’s not just about spending more money; it’s also about spending it wisely. Bad investments include pouring huge sums into superficial ads with no long-term follow-up, funding “one-and-done” digital pilot projects that lack a clear path for growth, sinking dollars into platforms whose profits flow back to the opposition, or giving money to charismatic leaders with the right words but no vision or plan for implementation. Equally counterproductive is focusing solely on impressions, clicks, or views rather than forging meaningful connections. A viral video might generate millions of views, but without sustained engagement and a defined strategy to convert viewers into active supporters, the effort ends up as a fleeting blip.
To avoid these pitfalls, progressive donors and organizations need a clear sense of what “success” means in the context of digital organizing, media ecosystems, and influencers. That success should be measured not merely by immediate reach but by how well an initiative builds real-world relationships, nurtures community, and moves audiences toward deeper involvement, volunteering, donating, and actions. This requires ongoing support and a willingness to experiment, refine tactics, and invest in the infrastructure, training, mentorship, and platform development that enables creators and communities to grow sustainably. Only with this level of commitment and strategic foresight can progressives build a powerful media ecosystem capable of shifting narratives and driving lasting political impact.
Closing
Ultimately, the debate around digital politics isn’t just about tweaking ad strategies; it’s about how we cultivate entire online communities that shape worldviews far beyond a single election cycle. The right has demonstrated, through relentless content creation and in-person organizing, that changing hearts and minds requires embedding yourself in people’s daily lives and cultural interests. Meanwhile, progressives have too often settled for short-term digital advertising, hoping that clever targeting alone would drive political transformation. Yet, as the data repeatedly shows, pouring millions of dollars into ad campaigns on Big Tech platforms seldom produces lasting impact and may even bolster opponents who benefit from corporate donations.
If progressives truly want to compete, they must take a page from the right’s playbook, forging irreverent, year-round digital brands that translate into meaningful offline engagement. That will demand time, creativity, and, yes, significant financial investment. There is no cheap shortcut in the race to shape public opinion. However, when progressives systematically fund authentic content creators, nurture micro-communities, and design events that generate viral online moments, they create a self-sustaining ecosystem, one that can capture the cultural imagination of diverse audiences. It is only by embracing such a holistic, relationship-focused approach that the left can stop mistaking flashy ads for true organizing and finally build the long-term momentum needed to reshape America’s political landscape.
Absolutely incredible article. Thank you for this!
https://open.substack.com/pub/sharonlawrence/p/elections-advice-to-democrats-communications?utm_source=share&utm_medium=android&r=a5esd
I'm been screaming about this for months. Above us my strategy.