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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 2-sentence description for the episode: Bradley Tusk, a political strategist turned venture capitalist, shares his insights on how startups can effectively navigate regulatory challenges by understanding politicians' motivations and leveraging customer support. Drawing from his experiences with companies like Uber and FanDuel, Tusk discusses the nuanced art of political lobbying, emphasizing the importance of aligning a startup's goals with a politician's electoral interests.
Creator Economy
Startup Founders
Tech Policy & Ethics
Bradley Tusk
Travis Kalanick
Michael Bloomberg
Uber
Coinbase

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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Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.

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Podcast Summary

In this powerful episode, Bradley Tusk reveals the hidden mechanics of startup lobbying after his legendary work getting Uber legalized across America. Drawing from high-stakes campaigns spanning Bloomberg's mayoral run to crypto's 2024 election dominance, Tusk breaks down his battle-tested framework for navigating regulatory warfare—from mobilizing customer armies (01:20) to understanding that every politician's decision revolves around winning the next election (02:59). He shares hard-won insights on when startups should engage politically, how crypto achieved unprecedented lobbying success with strategic $40 million investments (24:18), and his ambitious mobile voting project aimed at fundamentally reshaping democracy through technology.

Speakers

Bradley Tusk

Former deputy governor of Illinois and campaign manager for Michael Bloomberg's successful mayoral campaigns. Founded Tusk Strategies, a political consulting firm, and Tusk Ventures, investing $300M in highly regulated startups like Uber, FanDuel, and Coinbase while solving their regulatory challenges.

David Weisburd (Host)

Venture capitalist and host of How I Invest podcast. Based on his questions and approach, he brings experience from government work at city, state, and federal levels to his conversations with industry leaders.

Key Takeaways

Turn Customers Into Your Political Army

When regulators threaten your business, mobilize your users as constituents. Uber sent a message to 50,000 DC customers, who then contacted city council members within a week. (01:36) This grassroots pressure not only killed the anti-Uber bill but passed their own legislation 9-0. Politicians fear losing voters more than losing campaign contributions—your passionate customers are your strongest political asset.

Master the Political ROI Calculation

Every politician makes decisions solely based on winning their next election. (03:07) Show them how supporting your initiative helps them get reelected or how opposing it could cost them votes. Map out which constituents care about your issue and can vote in their district. If you can't demonstrate clear political benefit or risk, you become irrelevant to them.

Deploy the "Make Them Heroes" Strategy

Rather than waiting for politicians to decide, publicly thank them for supporting your cause before they've committed. (13:17) In New York's universal school meals campaign, they ran ads immediately crediting politicians for their support, making it politically costly to reverse course. This creates emotional investment and a template where your outcome becomes inevitable.

Start Small, Build Precedent, Scale Up

Create a stack ranking of jurisdictions from easiest to hardest based on political landscape, opposition strength, and regulatory complexity. (19:23) Win early battles in friendly markets to establish precedent and prove your model works, then leverage that success to tackle harder markets as your resources and credibility grow. Points on the board create momentum.

Know Your Regulatory Timeline and Stakes

Map when you need government approval in your product lifecycle—some companies like Lemonade needed insurance licenses on day one, while FanDuel operated in gray areas until regulatory backlash hit at Series E. (20:45) Understand the consequences of non-compliance: impounded cars are manageable, but SEC violations mean prison time. Budget and plan accordingly based on your specific risk profile.

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 DC reached out to city council members within a week in 2012, leading to a 9-0 vote (including the original bill sponsor against Uber) to pass Uber-friendly legislation. (01:31)
  2. Over 13 million kids in the US still don't get enough food at home and need it at school, yet political ROI calculations often prevent universal school meal funding despite popular support. (08:37)
  3. Crypto industry raised and deployed hundreds of millions of dollars in the 2024 election, including $40 million in Ohio's Senate race, creating a multiplier effect where other politicians changed behavior to avoid similar targeting. (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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