About this episode
I had the chance to speak with Bradley Tusk, the legendary political strategist turned venture capitalist. He started in politics—running Michael Bloomberg’s mayoral campaign and serving as Deputy Governor of Illinois—before becoming the fixer behind startups like Uber, FanDuel, Lemonade, and Coinbase. Now, he runs Tusk Holdings, where he invests in—and fights for—startups navigating regulation. We talked about his unique investing playbook, how to outmaneuver entrenched interests, what founders misunderstand about politics, and why he’s betting $20 million of his own money on mobile voting. I had the chance to speak with Bradley Tusk, the legendary political strategist turned venture capitalist. He started in politics—running Michael Bloomberg’s mayoral campaign and serving as Deputy Governor of Illinois—before becoming the fixer behind startups like Uber, FanDuel, Lemonade, and Coinbase. Now, he runs Tusk Holdings, where he invests in—and fights for—startups navigating regulation. We talked about his unique investing playbook, how to outmaneuver entrenched interests, what founders misunderstand about politics, and why he’s betting $20 million of his own money on mobile voting. -- Highlights: Why he believes every policy output is a political input How he helped Uber win political battles across the U.S. What makes politicians tick—and how to move them Why crypto had a breakthrough 2024 election cycle How Tusk Ventures invests in highly regulated industries The origin story of the Mobile Voting Project When startups should start lobbying—and how to do it effectively The one investment he regrets (and what it taught him) -- Guest Bio: Bradley Tusk is the founder and CEO of Tusk Holdings, which includes Tusk Ventures, Tusk Strategies, and the Tusk Philanthropies foundation. He was formerly Deputy Governor of Illinois and campaign manager for Michael Bloomberg’s 2009 mayoral race. He helped Uber navigate early political battles, taking equity as payment—and then repeated that playbook with FanDuel, Lemonade, Coinbase, and others. He is also the author of The Fixer and Vote With Your Phone, and the founder of the Mobile Voting Project. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement -- Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Bradley Tusk: https://www.linkedin.com/in/btusk/ Links Tusk Holdings: https://www.tuskholdings.com/ -- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Introduction (0:44) Strategies for Uber's expansion and political challenges (6:26) Michael Bloomberg's approach and political ROI examples (10:35) Modern lobbying and startup political influence (19:52) Timing for startups to engage in lobbying (22:19) Success and impact of the crypto lobby in elections (25:14) Elon Musk's potential political influence (30:04) Bradley Tusk's mobile voting project and its impact (35:20) Tusk Ventures' investment approach and regulatory appeal (39:51) Perspectives on opposing lobbies and venture capital (42:06) Lessons from investing and politics (43:23) Closing remarks