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How I Invest with David Weisburd
How I Invest with David Weisburd•August 20, 2025

E202: The Startup Lobbying Playbook w/Bradley Tusk

Here's a two-sentence description for the episode: Bradley Tusk, a political strategist turned venture capitalist, shares his insights on how startups can successfully navigate regulatory challenges by understanding politicians' motivations and mobilizing public support. Through examples like Uber and his work in various industries, Tusk explains the importance of crafting a compelling narrative that demonstrates how a startup's innovation can benefit society and advance public policy.
Startup Founders
Venture Capital
Political Philosophy
Tech Policy & Ethics
Government Surveillance & Privacy
Elon Musk
Bradley Tusk
Travis Kalanick

Summary Sections

  • Podcast Summary
  • Speakers
  • Key Takeaways
  • Compelling StoriesPremium
  • Strategies & FrameworksPremium
  • Thought-Provoking QuotesPremium
  • Statistics & Facts
  • Additional ContextPremium
  • Key Takeaways TablePlus
  • Critical AnalysisPlus
  • Similar StrategiesPlus
  • Books & Articles MentionedPlus
  • Products, Tools & Software MentionedPlus
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Podcast Summary

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.

Speakers

Bradley Tusk

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.

David Senra (Host)

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.

Key Takeaways

Master the Political Psychology Behind Every Decision

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.

Deploy Customer Armies as Your Secret Weapon

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.

Start with Wins, Then Scale the Mountain

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.

Know What You Don't Know—Or Fail Spectacularly

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.

Understand Your Regulatory Timeline Before You Need It

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.

Compelling Stories

Available with a Premium subscription

Strategies & Frameworks

Available with a Premium subscription

Thought-Provoking Quotes

Available with a Premium subscription

Statistics & Facts

  1. 50,000 Uber customers in Washington DC contacted their city council members within one week in 2012, leading to legislation passing 9-0, including support from the sponsor of the anti-Uber bill. (01:25)
  2. Over 13,000,000 kids in the United States still don't get enough food at home and need meals at school. (08:37)
  3. Crypto industry raised and deployed hundreds of millions of dollars in the 2024 election, including $40,000,000 in Ohio's Senate race alone, with their strategic investment potentially having billions in value by influencing other politicians' behavior. (24:18)

Additional Context

Available with a Premium subscription

Key Takeaways Table

Available with a Plus subscription

Critical Analysis

Available with a Plus subscription

Similar Strategies

Available with a Plus subscription

Books & Articles Mentioned

Available with a Plus subscription

Products, Tools & Software Mentioned

Available with a Plus subscription

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