WWDC

The Operator Who Rejects Consistency and Embraces Volatility David von Rosen is not your typical passive check-writer. The founder of Lottoland and property powerhouse 25 Degrees operates on a philosophy that prioritizes volatility over steady-state predictability. While many venture capitalists seek to de-risk their portfolios through diversification, von Rosen doubles down on high-conviction, high-ownership stakes. He argues that having a "gut feel" for innovation is far more valuable than a rigid playbook that limits an investor to a single sector. By focusing on fewer companies with higher equity positions—often 20% to 50%—he ensures that his operational "superpower" of creativity and strategy actually moves the needle. His approach to business is fundamentally anti-imitative. He finds the prospect of copying existing products boring, instead seeking out technologies or business models that have no precedent. This mindset has led him through disparate industries including gambling, fintech, energy, and luxury real estate. For von Rosen, the consistent factor isn't the industry, but the presence of a disruptive facet that allows for a massive payback on calculated risks. Hiring Generalists and Scaling via Motivation When it comes to building teams, von Rosen abandons the traditional obsession with credentials and deep industry experience. He has found success in hiring "hungry" individuals from entirely different sectors—even suggesting a dentist could make a brilliant CMO if they possess the right drive. This strategy prevents "tunnel vision" within a company, bringing in fresh perspectives that hasn't been dulled by years of the same industry-standard thinking. He looks for generalists, particularly young talent whose motivation can overcome significant hurdles. In his view, a CV is secondary to the person's ability to listen and their inherent fire for the venture. This focus on character over content allows his companies to remain agile and creative, traits he values more than formal education or specific technical backgrounds. This lean towards generalists allows him to deploy talent across his varied portfolio, ensuring that the "operator" spirit remains central to every business he backs. The Lottoland Playbook: Derivatives as Market Disruptors One of the most compelling examples of von Rosen's first-principles thinking is the birth of Lottoland. Noticing that the lottery industry was a series of closed, state-managed monopolies, he saw a problem: a German citizen couldn't play for a massive Powerball jackpot in the US. The regulatory walls were massive, but instead of trying to dismantle them, he built a synthetic workaround. By creating a "bet on a lottery" rather than selling a physical ticket, he bypassed international lottery restrictions. This derivative model allowed customers to select numbers and receive the exact same payout as the official lottery, backed by the bookmaker's own risk management and insurance structures. It transformed a stagnant, monopolized industry into a global digital playground. This breakthrough reinforces his core belief that you must "go where the market is" and adjust your idea flexibly until it fits the demand, rather than trying to force a product through an impenetrable wall. Why Dubai is the 1920s America of the Middle East Von Rosen is a vocal advocate for Dubai, describing it as a city with a "future-oriented soul" that attracts the world's most aggressive talent. He dismisses the common criticism that the city lacks heritage, arguing that Dubai has traded the morality of the past for a long-term approach to innovation and growth. To him, the city represents a unique melting pot where capital meets high-density talent, creating a self-fulfilling prophecy of success. He compares the current energy in the Middle East to the United States in the 1920s—a period of massive deregulation and opportunity. The lack of bureaucratic friction, combined with world-class lifestyle investments, makes it a magnet for entrepreneurs who are tired of the stagnant, past-focused economies of Europe. For von Rosen, Dubai isn't just a tax haven; it’s a strategic hub for those who want to think big, fast, and without the baggage of traditional heritage. The Steve Jobs Endorsement That Nearly Bankrupted a Brand Perhaps the most legendary story in von Rosen's career involves his former fashion label, Von Rosen. In 2010, the high-end brand was struggling to find a market for its expensive, logo-free garments. On a whim, fueled by a bottle of wine, von Rosen and a colleague decided to send their signature black turtleneck to Steve Jobs at Apple HQ. They didn't expect much more than a secretary possibly keeping the package, but weeks later, they received an order for three more sweaters—purchased on Jobs' personal credit card. In 2011, during the WWDC keynote where Steve Jobs introduced iCloud, he was wearing the Von Rosen turtleneck. The light reflected off a small metallic icon on the garment, sparking a global frenzy on TechCrunch and social media. Within hours, the brand was sold out worldwide. Despite this massive breakthrough, von Rosen eventually had to close the brand, a reminder that even the most spectacular marketing moments require a sustainable operational foundation. However, the legacy lives on: the brand is famously mentioned in the official Steve Jobs biography by Walter Isaacson as one of the few brands the Apple founder actually liked and wore. Fear Calibration and the Future of Defense Tech Looking forward, von Rosen is placing significant bets on Tytan Technologies, a German startup specializing in cost-effective counter-drone systems. He views defense tech as a sector destined for unicorn valuations given the current global geopolitical climate. His interest in this space mirrors his personal fascination with risk and fear management. He cites Alex Honnold, the world-renowned free solo climber, as an inspiration for how to perceive fear differently. Von Rosen believes that as entrepreneurs age, they often become more risk-averse, which he views as a biological error. He argues that as time grows shorter, one should actually take bigger, crazier risks. Whether it's investing in suicide-mission drone technology or betting on unregulated markets, his focus remains on the high-adrenaline, high-return ventures that make a founder feel truly alive. The goal is never just to maintain; it is to find the next punch in the face, get up, and win bigger.