Room to Run

In this episode, Robert examines how foreign influence campaigns may be attempting to slow America's AI infrastructure buildout by amplifying fears around data centers, while arguing that the long-term AI investment thesis remains intact. He explains why leadership is broadening beyond AI hardware into sectors like healthcare, financials, and select small caps, viewing the rotation as a health...

In this episode, Robert challenges the popular belief that high-profile IPOs signal the end of a bull market, arguing that history shows they are often a sign of strong liquidity rather than an imminent market top. He breaks down the conditions that have historically ended major bull markets, explains why he believes today's environment differs from past bubbles, and shares his current outlook on...

In this episode, Robert discusses an emerging investment theme that caught his attention after conversations with prominent technology and finance leaders: quantum computing and the cybersecurity challenges it could create. He explores the concept of "Q Day," why advances in quantum technology may eventually force governments and businesses to rethink digital security, and where investors may find...

In this episode, Robert argues that investors can acknowledge parts of the AI boom look excessive while still participating profitably. He discusses why some AI-related stocks may experience sharp pullbacks, but notes that current market conditions still look far different from the final stages of historic bubbles. He revisits his framework of owning long-term AI "toll roads" while tacti...

Are we in the middle of one of the greatest bull markets of our lifetime? In this episode, Robert Ross zooms out from the daily noise around earnings, Fed meetings, wars, tariffs, oil shocks, and market volatility to explain his “100-year market cycle” framework. Since the Great Depression, stocks have moved through long secular bull and bear markets, with each major bull cycle powered by a new wa...

In this episode, Robert explores the difference between companies building lasting AI moats versus those simply benefiting from temporary demand surges during the current boom. Using historical parallels, he explains how investors can think about “toll road” businesses versus “shovel sellers,” and why that distinction matters for long-term positioning. He also discusses how he’s approaching AI exp...

In this episode, Robert breaks down a pivotal week for the AI trade, where strong earnings and real revenue growth challenged many bearish narratives. He explains what these results signal about the current cycle, why market reactions matter more than opinions, and how he’s thinking about positioning after such a powerful move. He also touches on where opportunities may still exist, how to interpr...

In this episode, Robert challenges the idea that today’s market mirrors past bubbles and explains why the current AI cycle may be earlier than most believe. He breaks down the shift from heavy spending to real usage, why that distinction matters, and how it’s shaping his investment approach. He also covers how he’s thinking about opportunities within the AI ecosystem, the difference between broad...

In this episode, Robert breaks down the recent “lockout rally” and what it means for investors who were positioned defensively. He explains why markets often move in ways that frustrate the majority, and how staying disciplined through volatility can make all the difference. He dives into what could come next, including the role of market breadth, rotation, and upcoming earnings, while sharing how...

In this episode, Robert explains why market reactions matter more than headlines, especially during volatile periods. He breaks down how recent price action may be signaling a shift beneath the surface, even as negative news continues to dominate the narrative. He highlights key areas showing relative strength, how he’s thinking about potential leadership going forward, and why resilience during p...

In this episode, Robert breaks down how his investing approach has evolved over time and why the most effective strategies are often a blend rather than a single style. He explains how understanding your own temperament is key to building a process that actually works, and why discipline, patience, and adaptability matter more than labels. He also shares how he’s navigating the current market, the...

In this episode, Robert breaks down how his investing approach has evolved over time and why the most effective strategies are often a blend rather than a single style. He explains how understanding your own temperament is key to building a process that actually works, and why discipline, patience, and adaptability matter more than labels. He also shares how he’s navigating the current market, the...

In this episode, Robert gets candid about being wrong and why that’s not only normal in investing, but necessary. He breaks down how recent shifts in policy, inflation, and geopolitics in Iran have changed the landscape, and what that means for positioning right now. The focus is on what actually matters: managing risk, staying disciplined, and knowing when not to press. He also shares how he’s th...

In this episode, Robert explores the concept of the “wisdom of crowds” and how market price action can reveal more than the constant stream of alarming headlines investors see every day. He explains why the market’s resilience in the face of geopolitical tension, inflation fears, and technology-sector volatility may be sending an important signal about underlying demand for stocks. Robert discusse...

In this episode, Robert explains why markets often behave very differently from the emotional headlines surrounding major geopolitical events. Using historical context and current market signals, he breaks down how investors should think about volatility driven by war, oil shocks, and sudden spikes in fear. He discusses the key macro variables markets actually care about during crises, how to inte...

In this episode, Robert breaks down the psychological trap investors fall into during tight, frustrating markets and why trying to “fix” drawdowns with bigger position sizes often makes things worse. He explains how coiled spring market environments tend to resolve, why price action matters more than headlines, and what could realistically spark the next major move in stocks. The discussion also d...

In this episode, Robert draws a striking comparison between today’s AI-driven market and the early days of the internet boom, exploring why rotations into “safe” stocks often happen before the most explosive phase of a bull run. He explains how to think about pullbacks in high-growth sectors, what historically signals a true market top, and why patience can outperform panic during volatile stretch...

In this episode, Robert breaks down the myth that early Bitcoin investors simply “got lucky” and explains why surviving extreme volatility is the real price of outsized returns. He unpacks what recent crypto capitulation signals about leverage, sentiment, and long-term opportunity, and shares how he approaches multi-year positioning during historic drawdowns. The conversation also dives into the c...

In this episode, Robert breaks down why the most exciting trades are often the most dangerous and how extreme leverage can quietly turn short-term wins into long-term disasters. He explains why good trading is usually boring, how risk structure matters more than intelligence, and what habits help investors survive volatile markets without blowing up their accounts. Robert also discusses how he thi...

In this episode, Robert explains why having a short memory is one of the most important skills an investor can develop and how learning to move on from losses can unlock better long term results. He shares how discipline, position sizing, and a repeatable process matter more than any single trade, and why missed opportunities are not a reason to stop pulling the trigger. Robert also explores where...

In this episode, Robert explains why successful investing is not about prediction but about probabilities, positioning, and risk management. He breaks down how probabilistic thinking shapes portfolio decisions, why being wrong is inevitable, and how asymmetric risk reward setups allow investors to win over time without needing certainty. Robert then discusses where he currently sees favorable odds...

In this episode, Robert explores the real fear that drives most investing mistakes and why avoiding losses at all costs often leads to underperformance. He reframes risk through the lens of capital preservation, explains how process matters more than prediction, and walks through how narrative, fundamentals, and technicals come together when identifying high upside opportunities. Robert also answe...

In this episode, Robert looks past the headlines to explain why the sudden shift in Venezuela is more than a geopolitical shock and could have meaningful implications for inflation, interest rates, and market leadership. He breaks down how changes in global energy supply affect bond yields, Fed policy expectations, and the outlook for small caps, hard assets, and cyclical sectors. Robert also answ...

In this episode, Robert explains why the most important Fed move this week was not the rate cut everyone was debating, but a quieter shift that could reshape market liquidity. He walks through what renewed bond buying signals for monetary policy, why liquidity matters more than most macro headlines, and how this ties into the broader stimulus narrative taking shape. Robert also explores what this...

In this episode, Robert breaks down the coming shift in U.S. monetary policy and why markets may be underestimating how dramatic the next Fed era could become. He explores the implications of Kevin Hassett emerging as the likely successor to Jerome Powell, what an easier-for-longer playbook would mean for interest rates, liquidity, the dollar, and risk assets, and why small caps could become the n...