Who is Jesse Middleton?

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Jesse Middleton: Building Startups and Community with Authenticity in the NYC Tech Scene

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Jesse Middleton is a General Partner at Flybridge and co-founder of WeWork Labs, where he focuses on backing early-stage companies that challenge the status quo. With deep roots in New York’s startup ecosystem, he’s helped build and support over fifty ventures, particularly those innovating in the future of work and collaboration. His investment philosophy emphasizes founder-market fit, not just financial metrics. Jesse sees startups as people-first vehicles for transformation.

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More than just an investor, Jesse is a recognized community architect in the NYC tech scene. He actively supports initiatives like Tech:NYC and Next Wave NYC, aiming to make entrepreneurship more inclusive and sustainable. Whether advising founders or hosting meetups, Jesse fosters environments where creativity, support, and vulnerability are valued as much as traction. His presence is both local in action and global in outlook.

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What makes Jesse stand out is his openness about the personal side of building—he frequently shares candid reflections on sobriety, parenting, and growth. For him, personal evolution is as important as professional success. His social content mixes startup strategy with emotional honesty, creating a rare blend of founder empathy and business savvy. That balance resonates deeply with entrepreneurs navigating similar highs and lows.

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Jesse’s influence continues to grow across platforms where founders, operators, and investors alike seek authentic voices. He’s built a reputation not by broadcasting from a pedestal, but by standing eye-level with the community he helps shape. As a result, his voice carries not just credibility, but genuine trust—a trait increasingly rare in the venture capital world.

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An Influencer Active on Social Media

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Jesse Middleton maintains a multi-platform presence, with a strong lead on LinkedIn and complementary activity on X (Twitter), where he mixes community highlights, startup commentary, and personal insights.

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Jesse Middleton's Social Media Strategy Analysis

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LinkedIn: Founder-Centric Advice with a Personal Pulse

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On LinkedIn, Jesse Middleton shares a thoughtful blend of startup strategy, personal storytelling, and NYC tech advocacy. His posts feel more like honest conversations than professional broadcasts, resonating strongly with early-stage founders and community builders. Whether he's sharing a lighthearted birthday reflection or comparing New York and San Francisco startup ecosystems, Jesse’s tone is always relatable and real. It’s clear he writes not just to be seen—but to connect.

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He publishes regularly—about 21 posts per month—balancing tactical insights (e.g., capital efficiency, founder dynamics) with heartfelt moments on sobriety, fatherhood, or self-awareness. This consistency builds trust while showcasing depth beyond spreadsheets and pitch decks. One post explaining “why NYC > SF” broke down buyer proximity, time zones, and talent diversity, proving his knack for clarity in complexity. His writing is direct, smart, and emotionally intelligent.

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His posts are often short-form text, sometimes supplemented with photos, and always carry a distinct, first-person tone. He doesn’t rely on buzzwords or recycled content—instead, he shows up with his own voice. And when he does reference others, it’s to lift them up—whether they’re co-founders, portfolio companies, or other voices in the ecosystem. This makes him a central node in NYC’s startup storytelling fabric.

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Jesse’s LinkedIn content performs consistently well, with an average of 86 engagements and 16.3K views per post. His 0.4% engagement rate is strong for a founder-focused audience, and his growth of +2.92% indicates that his authentic approach is drawing in like-minded professionals. With daily posts around 10 AM, he’s reliably present without oversaturating, offering high-signal content that’s both strategic and soulful.

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• Username: @jmiddleton
• Influence Score: 92.5/100
• Followers: 21.7K
• Activity: 21 posts/month
• Engagement Rate: 0.4%
• Growth: +2.92% (621 new followers/month)
• Average Engagement: 86
• Average Views: 16.3K
• Posting Habits: Daily at 10 AM EST

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X (Twitter): NYC Snapshots and Real-Time Founder Energy

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On X (formerly Twitter), Jesse operates under the handle @srcasm, offering a more spontaneous, visual-first take on his life and work. His tweets include photos from NYC streets, panels at NYSE, and interactions with startup founders. This content gives followers a real-time pulse of the city’s innovation culture, as seen through the lens of someone deeply embedded in it. The posts are short, candid, and visually engaging.

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He’s less tactical on X and more cultural, using the platform to celebrate community wins and share startup wisdom in motion. A recent post on Jungle’s product removing credential bottlenecks generated 3.7K views, showing his ability to drive engagement even in niche discussions. He doesn’t tweet for metrics—he tweets to document, highlight, and observe. The result is a feed that feels like a founder's journal crossed with a street photo essay.

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While his engagement rate is low (0.06%), the platform serves a different purpose: building intimacy and immediacy. Jesse’s audience on X follows him for bite-sized updates on tech, events, and New York moments that would never make it into a formal blog or post. His voice here is sharper, sometimes playful, and more focused on community than commentary. He’s not trying to dominate conversations—he’s adding his lens to them.

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Despite modest numbers (12.3K followers, 6.4 tweets per week), Jesse’s Twitter presence complements his LinkedIn strategy, acting as a sandbox for observations and real-world snapshots. His posting habits mirror LinkedIn—daily at 10AM—keeping a consistent rhythm across platforms. For followers seeking an unfiltered look at startup life, @srcasm offers a window into the spaces, people, and quirks that power Jesse’s day-to-day.

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• Username: @srcasm
• Influence Score: 67.9/100
• Followers: 12.3K
• Activity: 6.4 tweets/week
• Engagement Rate: 0.06%
• Growth: 0%
• Average Engagement: 7
• Average Views: 669
• Posting Habits: Daily at 10 AM EST

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Jesse Middleton's Social Media Influence Summary

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With a Favikon influence score of 5/5 and 6,623 points, Jesse ranks in the top 1% on LinkedIn in the U.S. (#675) and top 6% among U.S. Venture Capital influencers (#169). He may not be the loudest voice in venture, but his quiet consistency and community-first approach earn him high trust and retention among his network.

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Learn more about the Favikon Methodology here

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Content Strategy: Where Startup Lessons Meet Human Stories

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Jesse’s content strategy is refreshingly personal—never overly polished or theoretical. He shares founder psychology, NYC startup dynamics, and life moments that reflect on professional identity. His “turning 39” post isn’t just a birthday message—it’s a lesson in perspective, maturity, and founder empathy. He also frequently uplifts others, whether it’s showcasing portfolio companies or spotlighting NYC-based founders.

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Reachability and Partnerships

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Jesse Middleton’s platform is well-suited for startups, early-stage funds, and tech community brands. With an audience made up of builders, creators, and ecosystem advocates, he’s likely to accept partnerships that align with his values of wellness, collaboration, and long-term thinking.

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His high brand safety and consistent engagement make him ideal for educational content, product launches, or ecosystem amplifications. Especially effective would be partnerships tied to NYC-based initiatives or mental health in tech. His trust-based style means brands would benefit from authentic, values-aligned promotion, not transactional visibility.

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Conclusion: Jesse Middleton Is Venture Capital with a Heart

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Jesse Middleton isn’t just building companies—he’s building connection. Through consistent storytelling, vulnerable insights, and platform authenticity, he’s carved out a unique space in the VC world. For founders and brands alike, he offers more than capital or clicks: he offers clarity, connection, and community.

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