Ankush Gera: Taking a different approach to AI investing

In an environment focused on hype cycles and lofty valuations, Ankush Gera has built a reputation for thinking differently.As the founder of Monsoon, Junglee, and Kunai, Ankush Gera has translated his experience in scaling businesses to a focus on investment. Having scaled these businesses to over 1,500 employees and 9 figures in revenues before exiting, he is now navigating what he believes to be a $10-100 trillion shift driven by AI.How operator experience shapes investment strategyGera doesn’t approach investment from a speculative standpoint, but based on a practical understanding of what it takes to scale a business. Having been an operator, he knows that it is equally important to evaluate how leadership teams under pressure as it is to determine product moat. Investment, in Gera’s eyes, is an exercise in risk management; rather than chasing upsides.“When you’ve built companies, scaled teams, gone through exits, and been tested repeatedly in the process, you develop a fundamentally different lens on risk and return,” Gera stated. With a perspective that considers not just vision, but hiring, capital efficiency, timing, and team dynamics, Gera holds to his understanding of what a successful business looks like. When a product is in the hands of a team he can’t trust under pressure, he expects that the business will lose value quickly. This kind of pattern recognition, he argues, is hard to replicate without having built a business of one’s own.Building a unique investment philosophyAlthough Gera knows what it takes to scale, no investor can fully understand all the unique dimensions of a business and how they scale with time. For this reason, Gera has adopted a “full body yes” principle. If something checks every box logically but doesn’t feel right, he passes. If something feels right, even if it’s unconventional, he leans in.Beyond what he feels about a given business, Gera says he looks for a sense of balance: “I tend to focus on larger checks in growth-stage opportunities where the return profiles are conservative, but the probability of capital loss is lower, and the path to these returns is materially faster than a high-risk, possible 100-1000x seed opportunity.Like many other investors, Gera’s interests are largely directed toward Silicon Valley. However, he acknowledges opportunities in emerging markets like India and Latin America. He views their typical combination of scale and lower-entry valuations as a compelling method for generating both returns and edge. Lessons learned and independence of thinkingBefore Gera evaluated businesses based on their individual balance, he relied too much on consensus. He recalls how he met the founders of Canva while kiteboarding in Maui and made introductions to investors in San Francisco. Although he spent time getting to know them, he and those investors passed on their proposition. At the time, he didn’t have enough liquidity or conviction to act alone. Gera realizes now that an investment in Canva would have been a 4,000-6,000x return.Today, Gera evaluates founders based on a combination of eccentricity, integrity, and humility. He wants to see extreme ownership, based not in pedigree but in skill. He recognizes that the best founders lead with empathy and also take full responsibility for their outcomes. He had seen these traits in himself, but wasn’t ready to recognize it in others during his early investing career. “The lesson wasn’t regret–it was independence of thinking,” he said. “I relied too much on consensus.”Why AI, robotics, and infrastructure stand outGera believes that the biggest winners in the market aren’t the flashiest players, but those who build the infrastructure. As AI, robotics, and other cutting-edge technologies work to build their own foundational layers, Gera’s eye is on those companies that want to provide the core utilities. It seems clear to him that these sectors are driving the market; the question is who will come out on top.“I framed my AI thesis around a simple question: ‘If I had today’s experience and capital during the early internet era, where would I have invested?’ This led to investments into model companies like Anthropic, picks and shovels like ScaleAI, compute with Groq, space and data with Starcloud, and developer tools like Replit. Infrastructure compounds. Applications churn. That’s at the root of how I invest into the sector.”Honing in on AI thesisMost enterprises are already building their platforms on the models set forward by companies like Anthropic and OpenAI. Businesses like Groq provide compute and chips, those like Crusoe develop data infrastructure, and those like Cursor and Replit offer developer tools. Gera argues that since other businesses are building on these companies as foundations, they could have the advantage moving forward.“At the time I invested in Anthropic, many people believed that OpenAI had too much of a lead,” Gera recalled. “But that was a bet on the team, and what I had heard of their integrity and vision. Similarly, Groq was a bet that a credible challenger could emerge in AI compute, and that even partial success could create significant value.”Concerns surrounding the AI application layerAlthough Gera is confident in the momentum of the foundational AI companies and AI technology as a whole, he seems less excited about the application layer. As underlying models improve, innovation is constantly being reset, and LLMs are eating up the moat of entire companies with one feature release. On top of that, this space is crowded and fast-moving, making it difficult to navigate and pick winners with certainty.“There will absolutely be winners in the application layer,” Gera said. “But from a risk-adjusted perspective, I find the foundational layers, infrastructure, and the picks and shovels more attractive.”Placing an emphasis on liquidity and risk managementIn environments where competition, regulation, and macroeconomic factors are constantly shifting, paper valuations tend to hold less weight. Companies that seem to be moving on an unstoppable trajectory can be set back by a shift in the foundations. Gera has seen this reality repeatedly, even within his own operating experience. For this reason, it is important to know when to take some chips off the table.“If you’re sitting on a 20x return within a year on an investment, taking partial liquidity and redeploying that capital is a viable strategy, “Gera stated. “But when markets are hot, even sophisticated investors succumb to avarice and ignore risks. I think about investing not just in terms of upside, but in terms of off-ramps and redeployment.”Diversification as an intentional investment strategyTechnologies like AI are impacting countless industries, including healthcare, space, defense, robotics, and more. Within each of these sectors, the technology and the companies developing it behave differently, and therefore come with distinct risk profiles. Gera has invested in several of these spaces, but asserts the importance of diversifying with intention, as opposed to chasing diversification for its own sake.Gera likes to compare Anthropic, Devoted Health, Figure AI, and Saronic; each operates in a completely different environment and has competitors within those environments. Each is subject to the unique risks of the industry, and must be evaluated within context without ignoring the broader AI innovation landscape.“Diversifying purely for the sake of it,” Gera argues, “is like taking a child who excels at math and forcing them to spend equal time on a subject they’re not naturally strong in. I’d rather double down in areas where I have conviction.”What investors are still getting wrongIn the realm of investing, it’s easy to get caught in the momentum. When paper valuations are rising and confidence is running high, many investors ignore subtle shifts in liquidity and ignore the need for off-ramps. If the market goes right, an investor should know whether they are actually able to realize gains on the opportunity.“At the end of the day,” Gera explained, “this is a long game. You’re going to be wrong, a lot. The goal isn’t to avoid that, it’s to stay in the game long enough, with enough discipline, to compound the wins.”Advice to those entering the investment spaceFinding success as an investor is hardly guaranteed, and this is something that Gera knows well. There is no shortage of legitimate opportunities out there on the open market, but there are many hundreds more that should be ignored. Personal strategy comes with experience, especially the kind of first-hand understanding that leaders like Gera claim. Knowing what makes a business scale matters.More generally, Gera advises that prospective investors focus on deal filtration more than deal flow. With this approach, it is important to pay attention to the terms of capital and position for the long game. Investors will lose money on their ventures; that’s just a part of the market. One’s goal should be to keep learning and refining strategies until something clicks into place.Investing involves risk, and your investment may lose value. Past performance gives no indication of future results. These statements do not constitute and cannot replace investment advice.VentureBeat newsroom and editorial staff were not involved in the creation of this content.

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