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Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
In this masterclass episode, Bradley Tusk—veteran political strategist behind Bloomberg's mayoral campaign and Uber's regulatory victories—reveals the psychology of political influence and startup lobbying. Tusk shares his framework for navigating highly regulated industries, from his early work legalizing ride-sharing (00:25) to building the crypto lobby's $40 million election strategy (24:18). He explores the fundamental truth that every politician makes decisions based solely on winning the next election (03:07), and demonstrates how savvy entrepreneurs can turn regulatory challenges into competitive advantages through grassroots mobilization, strategic narrative building, and understanding the political ROI that drives every policy decision.
Former campaign manager for Michael Bloomberg's mayoral campaign in NYC and early political strategist for Uber. Author of The Fixer and founder of Tusk Ventures, a venture capital fund specializing in highly regulated industries. He has successfully lobbied for companies like FanDuel, Coinbase, and Lemonade, with over $300M AUM across three funds.
Host of the How I Invest podcast, interviewing ambitious professionals and industry experts. He brings decades of curiosity about the intersection of politics and startups to his conversations with leaders who shape policy and business.
Every policy output is the result of a political input—politicians make decisions solely based on winning their next election. (03:07) Understanding this fundamental rule transforms how you approach any regulatory challenge. Whether you're lobbying for Uber or advocating for school meals, show politicians that supporting your cause will help them win or that opposing it could cost them votes. This isn't cynical; it's strategic reality that lets you align your business goals with their political incentives.
When Uber faced legislation that would shut them down in Washington DC, they mobilized 50,000 customers to contact city council members within a week. (01:25) The result? Not only did the hostile bill die, but Uber's own legislation passed 9-0, including support from the original bill's sponsor. This grassroots strategy consistently outperformed traditional lobbying because politicians fear losing thousands of constituent votes more than missing one company's campaign contribution.
Always create a stack ranking of jurisdictions from easiest to hardest wins based on current laws, political opponents, and available allies. (19:23) Begin where you can establish precedent and build momentum, then work toward tougher markets as your company gains resources and success. This approach lets you demonstrate that others have adopted your innovation safely, making harder battles winnable through social proof and proven track records.
Just because you went to Stanford or got Y Combinator backing doesn't mean you understand politics. (15:14) Founders who believe their impressive resumes automatically grant political influence become immediate investment red flags. Travis Kalanick succeeded with Uber partly because he recognized his political limitations and let experts handle regulatory strategy. Arrogance in unfamiliar domains—like funding a $4 million religion app without market understanding—leads to expensive disasters.
Some companies like Lemonade need regulatory approval before launching (insurance licenses), while others like FanDuel can operate in gray areas until political backlash forces legal clarification. (20:25) Map out what government permissions your business model requires and when in your product lifecycle they become critical. Budget reserves for political challenges because rapid growth inevitably threatens entrenched interests who will use their superior political relationships to fight back.