O'Leary: Chaos, AI, and Policy Shifts Fuel Entrepreneurial Success

Kevin O'Leary, the Shark Tank star and entrepreneur, asserted that statistical evidence confirms the best time to launch a business is during chaotic economic environments. In a recent interview with Politico, O'Leary cited historical precedents such as trade wars, periods of high interest rates, and real-estate market corrections as scenarios where entrepreneurs have thrived. "Every time the American economy is going through some kind of a correction is a fantastic time to be an entrepreneur," he stated, emphasizing the need for adaptability and strategic pivoting in turbulent times Kevin O’Leary says the best time to start a business is during chaos^[1]. This perspective aligns with data from the U.S. Census Bureau, which noted a surge in business applications during the pandemic, despite initial setbacks from lockdowns. August 2025 saw a 0.5% month-over-month increase in business applications, continuing a recovery trend amid earlier volatility linked to Trump-era tariffs Kevin O’Leary says the best time to start a business is during chaos^[1].

O'Leary also highlighted the transformative role of artificial intelligence (AI) in bolstering productivity and reducing costs across industries. He cited examples such as homebuilders leveraging AI for capital allocation and automakers navigating reduced tariffs through trade agreements. Deals with the European Union, Japan, and South Korea have cut auto tariffs to 15% from 25%, while also securing billions in U.S. investments. O'Leary argued that entrepreneurs should prioritize policy-driven opportunities during economic uncertainty, stating, "You want to find something that has completely been dislocated and invest in that because of the policy changes" Kevin O’Leary says the best time to start a business is during chaos^[1].

The entrepreneur also critiqued Trump administration policies that could hinder startup growth. These include interference with Federal Reserve independence and the proposed $100,000 H-1B visa fee, which he warned would disproportionately affect startups reliant on foreign talent. O'Leary noted that startups hiring AI engineers from abroad gain a competitive edge in the global talent race, advocating for H-1B adjustments that apply only to large corporations capable of absorbing such costs Kevin O’Leary says the best time to start a business is during chaos^[1].

The U.S. startup ecosystem remains under pressure, with 2024 marking a 25.6% increase in closures compared to 2023, according to Carta data. While O'Leary's optimism contrasts with the current climate, his emphasis on leveraging disruption and policy shifts offers a counterpoint to the challenges faced by founders. The interplay between macroeconomic factors-such as interest rates and regulatory changes-and entrepreneurial resilience continues to shape the startup landscape, with AI and strategic policy navigation emerging as key tools for success.