Investing Through Complexity “We talk about clarity of purpose and simplicity and focus. And we think that the most important thing in the investment business is to keep everything absolutely as simple as you possibly can. We think complexity is the biggest barrier to high performance in the investment business. And so we design around complexity.” — Reece Duca Reece Duca’s words capture a fundamental principle in investing: simplicity, clarity, and focus often lead to better decisions and better results. The most common advice passed from one generation of investors to the next is to avoid unnecessary complexity—to stay within your circle of competence, to favor what’s obvious, to design around complexity wherever possible. Yet some of the most successful investors of our time have done precisely the opposite. What if the best opportunities live in what Bill Gurley calls 'the messy middle'—where network effects create winner-take-all dynamics, where feedback loops amplify small advantages into insurmountable moats, where power laws mean the best investment isn't just better, but 10,000x better? What if the key to clarity isn't in avoiding complexity, but in understanding and navigating it with the right lens? This collection brings together five investors who’ve done just that: Bill Gurley of Benchmark, Nick Sleep and Qais Zakaria of Nomad, James Anderson of Baillie Gifford, the team at Dynamo, and Bill Miller of Legg Mason. Though their styles differ, they share a common intellectual foundation—one informed by the Santa Fe Institute and the study of complex adaptive systems. What makes these five especially interesting is not just their exposure to complexity science, but how differently they apply it. Gurley translates systems thinking into frameworks for understanding defensibility and disruption. Nomad approaches investing with philosophical clarity, using humor and metaphors to ground complex ideas. Anderson writes with the patience of a long-view optimist, finding simplicity in narratives of technological evolution. Dynamo draws from on-the-ground experience in emerging markets, offering a systems lens to environments most investors oversimplify. And Bill Miller, perhaps the most openly intellectual of the group, fuses behavioral finance, philosophy, and probability into market commentary that resists easy classification. These ideas weren't just intellectually satisfying—they generated billions in returns. Increasing Returns (Brian Arthur): Bill Gurley drew on SFI’s work on increasing returns and network effects to build conviction in Uber. He led Uber’s Series A in 2011 at a $60M valuation. Today, Uber’s market cap is over $200bn. Bill’s investment generated a reported $7bn+ for Benchmark. Scaling Laws (Geoffrey West): Nomad applied scaling laws and power law distributions to his long-term thesis on Amazon. Sleep and Zakaria first mentioned Amazon in their 2004 annual letter, and began buying its stock aggressively in 2005 at $30/share (market cap ~$15bn). After wounding down Nomad, Amazon was one of just three stocks Sleep owned. Today, Amazon trades at $222/share ($4,440/share; they conducted a 20:1 split in 2022) and has a market cap of $2.36tn. Innovation Rates (Jessica Trancik): James Anderson used SFI-inspired work around exponential change and energy innovation rates to underwrite Tesla well before it was consensus. Anderson first bought Tesla shares in 2013, when they were trading at $6/share (~$10bn market cap). Today, Tesla’s market cap is ~$1tn, and James’ investment generated a reported ~$30bn for Baillie Gifford. James has often credited SFI’s ideas with fundamentally driving every significant investment he’s made, including Amazon, Nvidia, Facebook, Tencent, and Alibaba. Complex Adaptive Systems (John Holland): Dynamo leaned on systems thinking to spot Mercado Libre’s potential in fragmented Latin American markets. They first laid out their thinking around markets being complex adaptive systems in a 2007 letter, the same year they invested in Mercado Libre’s IPO at ~16/share (although they quickly sold when the stock price doubled in just a few days). They re-initiated a position, at size, in 2016 at $166/share (~$8bn market cap). Today, the company trades at $2,500/share ($125bn market cap). Complexity Science (Murray Gell-Mann): Bill Miller used a broad range of core complexity ideas such as emergence (Stuart Kauffman), networks of exchange, and computational complexity to understand Bitcoin as an emergent monetary system. Bill first purchased Bitcoin in 2015 when it was trading at ~$200/BTC. Today, Bitcoin is trading at $110,000/BTC. Bill has also credited SFI with inspiring his investments in Dell and Apple in 1995, Amazon in 1999 (Legg Mason became the second largest holder of Amazon, only behind Jeff Bezos), and Google at its IPO in 2004 (market cap at the time was $23bn; today it is $2.2tn). All five investors work from a similar foundation, yet their expressions are highly distinct. That’s what complexity does: it permits multiple valid paths to insight. As Andy Benoit observed, “Most geniuses—especially those who lead others—prosper not by deconstructing intricate complexities but by exploiting unrecognized simplicities.” These investors do both. They move through complexity to arrive at a simplicity that is hard-earned, not superficial. Read these compilations not as investment literature but as a masterclass in applied thinking. They offer a glimpse into how frameworks from complexity science can yield practical insights—not only for picking stocks, but for understanding how the world works. They remind us that while investing may be “simple, but not easy,” it can be deeply coherent. Duca is right—complexity is indeed a barrier. But with the right lens, it becomes a moat. Those willing to cross it may find a clarity that, from the outside, looks like brilliance or luck. Sometimes, the best investors design around complexity. Other times, they walk straight through it. Below, you’ll find short introductions to five investors who chose to invest through complexity, along with compilations of their collected writings. We’ve chosen to present these works as long-form bodies of thought to highlight how their philosophies evolved over time — and how the ideas of the Santa Fe Institute helped shape both their frameworks and their investment decisions.