✍️ Outsider Ink: Kevin O'Connor Rewind, The Map of Innovation, Sparking New York's Tech Ecosystem

Outsider Ink is a bi-weekly newsletter from Outsider Inc.

The latest edition of Outsider Inc. welcomed Kevin O’Connor, the co-founder and CEO of DoubleClick—a digital advertising platform that helped launch the commercial internet in the late-1990s and was acquired by Google for $3.1B in 2007. DoubleClick is also credited with sparking New York City's now-thriving tech ecosystem. After relocating to Santa Barbara, Kevin went on to found Graphiq, a data aggregation and vertical search engine that became a critical component of Amazon’s Alexa platform. Kevin has also been a first-check investor in multiple companies that went on to produce billions in exit value, including Procore Technologies, where he continues to serve on the company’s board. Today, he's backing enterprise software entrepreneurs outside Silicon Valley through his firm ScOp Venture Capital. Over the years, Kevin has consistently bet early on non-obvious people, places, and ideas. This is a great episode. Tune in now ⤵️.

Listen: Spotify, Apple Podcasts, Amazon Music, YouTube

Follow: LinkedIn, Instagram, X, TikTok

The Map of Innovation

In 2003, Kevin published The Map of Innovation: Creating Something out of Nothing, a practical framework for building high-growth startups by cultivating a mindset of curiosity, experimentation, and urgency. Drawing from his entrepreneurial journey, he breaks down how ideas are generated, how they evolve into products, and what it takes to turn those products into successful companies. The book is structured as both a memoir and a guide, weaving personal stories with actionable lessons aimed at founders, operators, and anyone seeking to solve problems through innovation.

One of the book’s core insights is that innovation isn’t about having a perfect plan—it’s about identifying unmet needs, testing relentlessly, and moving fast while others hesitate. Kevin emphasizes that great ideas often start out as bad ideas until they’re refined through friction and feedback. He introduces tools like the “Innovation Matrix” to help entrepreneurs assess opportunity spaces and spot overlooked niches. Another key theme is the importance of culture—how to hire curious people, foster urgency, and eliminate fear of failure. Rather than glorifying genius or vision, Kevin centers the role of process and discipline in achieving breakout outcomes.

What I appreciate most about The Map of Innovation is its grounding in honesty. Kevin doesn’t romanticize entrepreneurship; he demystifies it. The book stands out from others in the genre because it’s not trying to impress—it’s trying to teach. His tone is direct, funny, and always focused on what actually works. It is a refreshing reminder that innovation is less about inspiration and more about iteration, persistence, and pattern recognition. It’s a book I recommend to any early-stage founder.

Sparking New York's Tech Ecosystem

DoubleClick played a foundational role in catalyzing the now-thriving New York City tech startup ecosystem in the late-1990s and early-2000s. As one of the first major tech success stories to emerge from the city, DoubleClick's IPO and $3.1B acquisition by Google put New York on the map for venture-backed tech startups. The company not only demonstrated the viability of internet advertising as a business model but also as a proof point that New York could host billion-dollar tech enterprises, paving the way for investor interest and entrepreneurial ambition in the region.

DoubleClick also helped spawn a new generation of founders in New York City’s tech ecosystem. According to Endeavor research, as of 2014, more than 20 companies were founded by DoubleClick alumni, including major startups like Gilt Groupe, AppNexus, and Right Media. These founders leveraged the operational experience, network connectivity, and access to capital they had developed during their tenure at DoubleClick. This phenomenon, often referred to as entrepreneurial recycling or the multiplier effect, created a ripple across the tech community, making DoubleClick one of the most important nodes in New York City’s startup genealogy.

The DoubleClick diaspora also seeded the broader ecosystem through mentorship, angel investing, and leadership roles in emerging startups. Many former employees went on to become venture capitalists or startup executives, creating a virtuous cycle of talent and capital in New York’s growing tech scene. The legacy of DoubleClick is not just its exit, but the institutional knowledge and network it disseminated across the city—a playbook that continues to shape NYC’s entrepreneurial fabric today.

Episode Highlights

Below are some of my favorite moments during the episode. Here, Kevin describes an encounter with media mogul Michael Bloomberg in the mid-to-late 1990s. Although Bloomberg, the company, of course ultimately embraced the online model, the story highlights how entrenched industries can initially resist rapidly-evolving innovation:

And second, Kevin comments on how founder entitlement can lead to poor company outcomes. Instead, founders should focus on the role they are playing and the value they’re adding to the company. Critically, these can—and often should—evolve over time. Founders should not resist this natural evolution and understand that the needs of the company may exceed their experience set.

I was deeply inspired by my conversation with Kevin. What stands out to me most about Kevin is his clarity of thought, radical candor, and deep conviction in outsiders—whether it’s where they’re from, how they think, or how long it takes. To me, Kevin's lasting imprint is not just about his impressive accomplishments—it's also about the people and ecosystems he empowered to build after him.

Up Next

Tune in next week when we’re joined by Brad Feld, co-founder and general partner of Foundry Group, an early-stage venture capital firm in Boulder, Colorado, and co-founder and board director of Techstars, the world’s largest and most geographically distributed pre-seed investor. Brad has a legendary reputation in the worlds of tech startups and venture capital, not just for his substantial accomplishments as an entrepreneur and investor, but for his unique approach to leadership and generosity—expressed through an impressive collection of writing, mentoring, and philanthropy. Brad is also a dear friend and mentor to me, so I’m especially excited to share this one with our listeners. Our conversation centered around Brad’s philosophy and approach to life and business, rather than a re-hash of all he’s accomplished. This is a special episode that you won’t want to miss. Tune in next week.