*Fred Wilson, Union Square Ventures

PJ Parson, Northzone and Spotify

🎙️ Episode Guide — PJ Parson (Northzone) Welcome to my series on OG NY Tech Celebrating 30 years of the New York tech ecosystem, from 1995 to now. PJ Parson is a partner at Northzone, best known for backing Spotify when it expanded to New York in 2012. But his path to venture capital wasn’t linear—it ran through small-town Sweden, jazz musicianship, tour guiding in Italy, ski resorts in France, McKinsey, fish farming, and eventually private equity. His story is about how unconventional experiences shaped his ability to see opportunity, manage chaos, and eventually help build New York’s second wave of tech. This conversation is about the hidden arcs behind venture capital: not just finance, but music, culture, resilience, and the willingness to reinvent yourself. SECTION I — ORIGINS AND EARLY ADVENTURES 00:00 – Small town Sweden to Dayton, Ohio PJ describes growing up in Sweden, then spending a formative exchange year in Dayton, Ohio. The contrast opened his eyes to the wider world. 00:42 – Three gap years of adventure Instead of rushing to university, PJ spent three years as a tour guide in Italy and ski guide in France. What began as playing music for tourists turned into managing excursions and eventually running large resorts with hundreds of guests per week. 03:00 – Learning history by necessity Thrown into leading tours of Rome, Florence, and Pisa, PJ immersed himself in Renaissance and Roman history—discovering a love of learning outside the classroom. SECTION II — UNIVERSITY AND DISCIPLINE 07:30 – Stockholm School of Economics After years of adventure, PJ enrolled at Sweden’s top business school. His vision deficiency exempted him from military service, but the maturity gained from his gap years helped him thrive academically. 09:00 – Trial by fire in microeconomics A professor failed him twice before finally passing him on the third attempt, teaching him the value of rigor and persistence. SECTION III — MCKINSEY: SURVIVAL AND STRUCTURE 11:00 – Entering consulting almost by accident PJ applied for a McKinsey internship with little knowledge of consulting. His charisma and conceptual thinking got him in, despite average grades. 17:00 – “You’re a mis-hire” After just one project, McKinsey tried to fire him. PJ pushed back, arguing for another chance—and survived. He stayed five years, learning the discipline of structure, detail, and execution. SECTION IV — PRIVATE EQUITY AND FISH FARMING 20:00 – Leaving McKinsey for private equity In 1993, PJ joined one of Sweden’s early private equity firms. But he quickly found the work too removed from real operations. 22:00 – Becoming a fish CEO Sent to fix a struggling fish distribution company, PJ became CEO. He turned around the business by slashing working capital, introducing just-in-time methods, and building simple internet-based systems in the mid-1990s. 25:00 – Buying the company for $1 When the firm gave up, PJ took over the company himself—proving his ability to lead a turnaround. SECTION V — LESSONS BEFORE VENTURE 27:00 – From chaos to clarity Running ski resorts, surviving McKinsey, and saving a fish company all taught PJ the same lesson: leadership is about managing complexity, staying calm in chaos, and finding leverage in systems. 29:00 – Toward venture capital These experiences set the stage for his later career in private equity and eventually Northzone—where he would back Spotify and help shape New York’s tech scene. CLOSING — THE ARC OF PJ PARSON PJ’s story shows that venture capital isn’t just about finance. It’s about lived experience: music, travel, management under pressure, and the ability to reinvent yourself. From Swedish jazz roots to Spotify in New York, his path reflects the eclectic, global, and resilient spirit that defines the New York tech ecosystem.

Kevin Ryan, Alleycorp + MongoDB ++ Doubleclick, Dilbert

>updated with vibier sound!< WELCOME TO MY SERIES ON OG NY TECH Celebrating 30 years of the New York tech ecosystem, from 1995 to now. Kevin Ryan joined DoubleClick in 1996, just months after it was founded—and helped turn it into the most important New York technology company of the internet era. From there, he went on to co-found or incubate a generation of defining NYC companies: MongoDB, Business Insider, Gilt Groupe, and dozens more through AlleyCorp. This conversation is about how New York tech actually formed: not in garages, not via hype cycles, but through media, advertising, distribution, discipline—and people who stayed when it got ugly. 🎙️ EPISODE CHAPTERS — KEVIN RYAN DoubleClick, the Internet Crash, and Building New York’s Second Tech Act SECTION I — BEFORE “NEW YORK TECH” EXISTED 00:00 – Books, tapes, and recording everything The conversation opens not with startups, but with New York itself—books about the city, recording devices, and the instinct to document moments that don’t yet feel historic. A fitting entry point for someone who repeatedly found himself early to structural change. 03:00 – From Europe to Yale to Wall Street A childhood split between Rome, Geneva, and Ohio. Yale economics and art history. Investment banking. Business school at INSEAD. Disney Paris during the launch of Euro Disney—scaling from 1,000 to 20,000 employees in under two years. Operations before tech. Execution before mythology. SECTION II — MEDIA, CARTOONS, AND THE PRE-BROWSER INTERNET 07:30 – Running Dilbert… before browsers existed At United Media (a division of E.W. Scripps), Kevin builds one of the earliest commercial websites—for Dilbert and other syndicated content—before Netscape, before Mosaic adoption, before “the web” meant anything to most people. 09:30 – Why this mattered Syndication economics are collapsing. Newspapers are consolidating. The internet quietly offers a way to bypass gatekeepers and go direct to audiences—if anyone can figure out how to monetize it. 11:30 – The first banner ads Ads are hard-coded. Prices are invented on the spot. Netscape and IBM buy week-long placements. Measurement barely exists. But something clicks: distribution plus software beats content alone. SECTION III — 1995–1996: SILICON ALLEY, BARELY 15:30 – How small it really was In 1995 New York internet events fit in a room. Everyone knows everyone. Media companies flirt with AOL, Prodigy, and Pathfinder. Most incumbents wait for “the next internet.” 16:30 – The innovator’s dilemma, live Kevin proposes building a real internet division inside United Media. Leadership declines—too small, too uncertain, too reminiscent of the CD-ROM bust. A textbook example, unfolding in real time. SECTION IV — DOUBLECLICK: THE RIGHT ABSTRACTION 18:00 – Meeting the founders Kevin meets Dwight Merriman and Kevin O’Connor—recent arrivals from Atlanta with a radical idea: dynamic ad serving. Smarter, measurable, programmable advertising. 19:30 – Knowing what you don’t know Kevin immediately understands the business importance—and immediately knows he can’t build it himself. The partnership works because the abstraction is right and the roles are clear. 21:00 – From CFO to President to CEO Joined in mid-1996 as CFO. Becomes President within months. Later CEO. The company grows from 10 people to 2,000 in four years. IPO in 1998—just 24 months after founding. SECTION V — THE BOOM, THEN THE COLLAPSE 24:30 – 1998–2000: Peak Silicon Alley DoubleClick becomes New York’s most valuable tech company. Tens of billions in valuation. The center of gravity for online advertising globally. 25:30 – The crash everyone misremembers In 2000–2001, 70% of DoubleClick’s customers go bankrupt. Competitors give away product to survive. Markets panic. Kevin’s contrarian take: The market wasn’t wrong in 2000—it was wrong in 2001. Buying the leaders at the peak would still have paid off long-term. 28:30 – Survival math Half the staff is laid off. Businesses are sold. But ad volume keeps doubling. Product quality compounds. Competitors die. The “fat get thin; the thin die.” SECTION VI — WHY HE STAYED 31:00 – The CEO decision Kevin becomes CEO as conditions worsen—not improve. Morale is low. The job is brutal. But the fundamentals are undeniable: internet advertising isn’t going away. 33:00 – Looking past the stock price If you ignore the ticker and look only at usage, share, and technical advantage, the outcome is obvious. That conviction carries the company through. SECTION VII — LEAVING, THEN STARTING AGAIN 35:00 – Exiting DoubleClick After nine years, DoubleClick is sold to private equity (and later to Google). Kevin leaves—not out of failure, but boredom. Ad tech is solved. 36:00 – AlleyCorp: Incubation as craft From 2005 to 2008, Kevin and Dwight incubate six companies at once, investing their own capital, acting as chair and technical backstop. 37:30 – The hits * MongoDB — open source, enterprise software, ten-year overnight success * Business Insider — hiring Henry Blodget, betting on redemption and velocity * Gilt Groupe — fashion, logistics, and scale at internet speed Also: Panther, ShopWiki, Music Nation—some wins, some misses. The math still works. SECTION VIII — MONGODB AND THE NEW YORK ENTERPRISE MYTH 44:00 – “You can’t build enterprise software in NYC” MongoDB disproves it. Slowly. Painfully. No revenue for years. Then compounding takes over. 46:00 – The long curve After 10+ years, MongoDB goes public at ~$100M revenue. The vast majority of value is created after year eleven. 47:30 – What people get wrong New York doesn’t lack technical talent. It lacks patience myths. Enterprise outcomes reward persistence more than hype. SECTION IX — FROM BUILDER TO PLATFORM 50:00 – After 2013 AlleyCorp evolves from pure incubation to investing at scale. One LP becomes many. Fifteen to twenty investments per year. Fewer incubations. More pattern recognition. 52:00 – Having good ideas Good ideas aren’t brainstorms. They’re friction noticed repeatedly: Business news that doesn’t update. Wedding registries that sell plates instead of experiences. Databases that don’t match modern data. CLOSING — THE ACTUAL ARC OF NEW YORK TECH 54:00 – What this story really shows New York tech didn’t emerge from imitation. It emerged from media, ads, logistics, finance, and people willing to stay through down cycles. 55:00 – The hidden continuity From Dilbert on pre-browser internet to MongoDB at $30B+, this is one continuous story—not reinvention, but accumulation.

Howard Morgan, First Round and BCap

Welcome to my series on OG NY Tech -- celebrating 30 years of NY tech ecosystem, from 1995 to now. Howard Morgan started as an engineer and professor in the early computing days, and ended up building three (four? five?) huge and import investment groups. Renaissance... Idealab... and listen for more on the early computing gods through to Bitcoin and AI. 🎙️ EPISODE CHAPTERS — HOWARD MORGAN Computers Before PCs, Venture Before “Venture,” and the Hidden Origins of Quant Finance SECTION I — THE LONG ARC: FROM MAINFRAMES TO THE INTERNET 00:00 – Recording everything Louis Armstrong’s house in Queens, tape recorders running 24/7, and the idea that capturing everything matters—an unexpected entry point into a life spent documenting and building the future.  02:00 – Why keep doing this? Why founders and investors in their 70s, 80s, and 90s keep starting new firms: curiosity, youth by proximity, and the refusal to stop building.  04:00 – 1995 is arbitrary (but useful) Why the mid-1990s are a convenient marker for New York tech—even though the real story starts decades earlier.  06:30 – Browsers before browsers Early web commercialization: Mosaic, Spyglass, Quarterdeck, browser history, and the moment when the web quietly crossed from research to product.  SECTION II — BECOMING A COMPUTER SCIENTIST (1960S–1970S) 07:30 – City College, 1962 Discovering computers via a desk-sized machine with punch tape—and deciding, very early, to go all-in.  09:00 – Dick Hamming’s intervention A Bell Labs legend redirects a physics student toward computers, operations research, and what would become modern computing.  10:30 – Speedrunning academia Three years of high school, three years of college, three years to a PhD—becoming the youngest assistant professor at Cornell.  11:30 – The first computer-printed PhD thesis Punch cards, justified text, and convincing the university that this was the future.  12:30 – Making computers less stupid Early spell-checking, syntax correction, semantic error handling—and the belief that computers should fix mistakes, not punish users.  SECTION III — THE OFFICE OF THE FUTURE (BEFORE IT WAS OBVIOUS) 14:00 – Databases, UX, and email (1970s) Large databases measured by the ton, early email, and building user-friendly systems long before “UX” was a term.  16:00 – Windows before Windows Multi-window systems, color vs. black-and-white debates with Alan Kay, and building what Xerox PARC would later popularize.  18:00 – Personal computers as an experiment DARPA hands out minicomputers to see what researchers will do—and accidentally invents networked personal computing.  19:00 – The wine list incident Creating one of the earliest online interest groups—and being told to shut it down before Congress notices.  SECTION IV — FROM RESEARCH TO VENTURE (LATE 1970S–1980S) 21:00 – First taste of company-building Commercializing Unix, meeting Jim Simons, and realizing that investing—not academia—might be the real lever.  23:00 – Jim Simons before Renaissance How a math professor accumulates capital, discovers computing’s power in markets, and dreams of a money-making machine.  25:00 – Founding Renaissance (1982) Splitting time between quant trading and venture investing—before either category really existed.  27:00 – Early deep tech investing Encryption hardware, LCD panels, Unix tools, QA software—companies that look like modern “deep tech” decades early.  SECTION V — QUANT CHANGES EVERYTHING 31:00 – The great split Venture returns at ~25% IRR, quant at ~38%—and the decision to spin venture out of Renaissance.  33:00 – Medallion Fund mythology Capacity limits, extreme fees, internal-only capital, and quietly becoming the most successful hedge fund in history.  35:00 – The quant ecosystem forms D.E. Shaw, Two Sigma, AQR—time series, statistics, and data replace “market intuition.”  38:00 – Alternative data before it had a name Clickstream analysis, URL bars, and predicting Amazon revenue before earnings calls.  SECTION VI — IDEALAB AND THE INTERNET BOOM 42:00 – Why Idealab mattered Company-creation as a system: projects before companies, cheap experimentation, and speed as advantage.  44:00 – The 2000 peak Raising $1B+ at a $9B valuation, surviving the crash, and why Idealab outlasted its peers.  46:00 – Citysearch, GoTo, Overture Search, local discovery, and the foundations of modern internet advertising.  SECTION VII — NEW YORK TECH COMES INTO FOCUS 48:00 – Returning to New York From Philly and California back to NYC—just as New York tech finally coheres as a scene.  49:00 – New York New Media Association Meetups, early angels, and the connective tissue that becomes the New York startup ecosystem.  50:00 – Deals you miss, deals you hit DoubleClick envy, Half.com’s sale to eBay, and why timing always beats intelligence.  CLOSING — PERSPECTIVE FROM THE LONG VIEW 52:00 – Seeing it all (except the iPhone) Why most of the future was visible decades early—and why consumer mobile computing still surprised everyone.  54:00 – The hidden history of New York tech Before startups were cool, before venture had a name, before quant was dominant—New York was already shaping the future.

*Fred Wilson, Union Square Ventures

>updated with vibier sound!< Welcome to my series on OG NY Tech -- celebrating 30 years of NY tech ecosystem, from 1995 to now. Fred Wilson's USV is kind of a 'nuff said, to borrow NYC comic book language. Hear the very early days and listen past through into the epilogue to hear Fred on music scenes and the process of discovery. 🎙️ EPISODE CHAPTERS SECTION I — THE CORE INTERVIEW: BUILDING NEW YORK TECH (1990S → NOW) 00:00 – Opening & framing OG New York tech Why this conversation exists: 30 years of New York tech, the OGNY moment, and why Fred Wilson’s career offers a uniquely New York lens on venture, media, and culture.  03:00 – Fred’s origin story (engineering → venture) Growing up everywhere, landing in New York, fleeing engineering, and discovering venture capital as the overlap between money and technology.  07:30 – Venture capital before the internet What 1980s venture actually looked like: PCs, networking, and a financial world that barely knew what to do with software.  10:30 – The 1995 New York “New Media” scene Journalists, artists, media kids, and early internet builders collide—AOL, CD-ROMs, web artists, and why New York’s tech scene grew out of culture, not semiconductors.  13:00 – Starting Flatiron Partners Leaving Euclid, early internet bets, and the unlikely move that gave Flatiron real firepower: institutional backing from Chase and SoftBank before the bubble mentality fully arrived.  18:00 – “You’re investing in a website?” A defining venture lesson: the best investments often sound ridiculous at first. Why laughter and disbelief are leading indicators of outsized returns.  21:00 – Three core investing principles Contrarian ideas people hate, founders driven by obsession rather than business plans, and why it’s often a mistake to monetize too early.  26:00 – Missionary founders (Etsy, Duolingo) Accidental entrepreneurs, aesthetic conviction, and building scale before business models—why belief comes before revenue.  30:00 – New York culture as an investing advantage Why art, music, and creative subcultures shaped investments like Etsy, Kickstarter, and SoundCloud—and why Silicon Valley logic didn’t fully apply.  34:00 – Blogging, influence, and burnout The rise of AVC: daily writing, community, learning in public—and why politics and online toxicity eventually broke the spell.  47:00 – Big funds vs. artisanal venture A candid reassessment: mega-funds may have “won,” even if small, craft-driven venture remains more personally meaningful.  52:00 – Cult classic vs. blockbuster Impact, legacy, and why some investors (and companies) choose influence over maximum scale.  SECTION II — EPILOGUE: MUSIC, TASTE, AND DISCOVERY (PRE-GAME CHAT) 55:00 – Music as a life pattern Classic rock, indie, and the joy of discovering what’s next rather than replaying the canon.  57:00 – Being early, not right Why showing up to small shows, supporting emerging artists, and sharing discoveries mirrors great investing behavior.  59:00 – Taste as practice Curiosity, openness, and cultural participation—not optimization—as the quiet through-line connecting music fandom, blogging, and venture capital.

Alan Patricof, APAX, Greycroft and Primetime

Welcome to my series on OG NY Tech -- celebrating 30 years of NY tech ecosystem, from 1995 to now. Alan Patricof's been at it since he graduated from Columbia Business School just a couple years apart from Warren Buffett. And you might as well think of him in that same legend league, in Alan's case for Venture Capital. We start from the very early days and go right through today. 🎙️ EPISODE CHAPTERS — ALAN PATRICOF Inventing Venture Capital in New York, Then Walking Away (Repeatedly) SECTION I — THE CORE INTERVIEW: A 70-YEAR VIEW OF VENTURE 00:00 – A living timeline Setting the frame: Alan Patricof at 91, still working, still curious—why this is less an interview than an oral history of American venture capital.  03:00 – Pounding the pavement (1950s Wall Street) No recruiters, no security desks: walking every building on Wall Street, floor by floor, asking for a job. How finance careers started before finance careers existed.  05:30 – Learning investing the slow way Investment counseling, portfolio construction, and why balanced, family-office style investing shaped everything that came later.  07:30 – Development capital before “venture” Real estate, bridges, electronics, finance companies—proto-venture investing before the word venture capital meant anything.  10:30 – Family offices and private deals Discovering the overlooked power of private company investing while everyone else focused on public stocks—and why this felt more human.  13:00 – Becoming a board member at 34 New York Magazine, Datascope, Lin Broadcasting: early board roles, founder relationships, and the addictive pull of building instead of trading.  15:30 – What separates great founders The pivot instinct: knowing when to abandon the original market and redirect a product without abandoning conviction.  18:00 – “You invest in the jockey” Why founder psychology matters more than ideas, and why you can’t actually diagnose this until you’re already in business together.  SECTION II — INVENTING VENTURE CAPITAL (1968–1980S) 20:00 – Starting Patricof & Co. Nine family offices, a tiny first fund, and the realization that venture could be a service business as much as a capital business.  22:00 – Warburg, Pincus, and the early peers The handful of firms inventing venture in parallel—and how indistinct the lines were between VC, merchant banking, and private equity.  24:00 – Surviving the 1970s Why venture almost died: inflation, stagnation, and the need to do M&A work just to keep the lights on.  26:00 – Going international before it was fashionable London, Paris, New York—building venture infrastructure in Europe when the concept barely translated (literally “capital risk”).  27:30 – The birth of Apax Unifying global activities under one name and accidentally creating one of the world’s largest private equity platforms.  SECTION III — ICONIC DEALS BEFORE TECH WAS “TECH” 29:00 – Apple, almost casually A phone call, a small allocation, a $315k check—and a reminder that early venture often felt mundane in the moment.  31:30 – Why nobody held forever Ten-year funds, capital recycling, and why paper fortunes usually stayed theoretical.  33:00 – Beating the bushes for deals Fifteen deals a year, maybe one investment—finding companies meant showing up physically, not scrolling inboxes.  35:00 – Office Depot and firm-building Delegation, partnership, and why building institutions matters more than personal deal mythology.  37:00 – AOL’s forgotten origin Online games, modems, bankruptcy, and the pivot from play to communication that reshaped the internet.  40:00 – Doing the messy work Hands-on restructuring, capital engineering, and why early venture often looked more like salvage than storytelling.  SECTION IV — WALKING AWAY (AND STARTING AGAIN) 44:00 – Why Apax stopped feeling like venture Scale, later-stage gravity, and the quiet moment when a firm becomes something else.  46:00 – A detour into global development World Bank, IFC, Trickle Up, and applying venture logic to poverty, SMEs, and economic development.  48:00 – Founding Greycroft Writing “no private equity” into the mission, timing the internet perfectly, and building another major platform from scratch.  50:00 – Venmo, Huffington Post, and the Web 2.0 wave Media, payments, identity, and why New York finally started producing global tech brands.  52:00 – PrimeTime Partners Aging, longevity, and investing with personal urgency—spotting demographic inevitability before it became fashionable.  SECTION V — NEW YORK, FINALLY 54:00 – Why New York couldn’t win earlier Crime, cost, culture, and why founders simply didn’t want to live here in the 70s and 80s.  56:00 – Media as New York’s wedge Audible, publishing, advertising, and why content and distribution cracked the door before infrastructure followed.  58:00 – The tipping point From DoubleClick to Datadog: why everyone now needs a New York presence—and why this time feels durable.  CLOSING — PERSPECTIVE FROM REPETITION 01:00:00 – The rare skill Not spotting waves once, but having the courage to leave institutions when they stop matching your values—and doing it again.