William Hockey: How I Founded Plaid; The Ultimate Cold Email Tip; Hiring Lessons | 20VC #955

Will Hockey is the Co-Founder and Co-CEO @ Column, the only nationally chartered bank built to enable developers and builders to create new financial products. Before co-founding Column, Will was the Co-Founder, President, and CTO @ Plaid, a world-leading data network and payments platform. In 2020, Visa attempted to acquire Plaid for $5.3BN, however, this was blocked due to regulatory issues and the company went on to raise at a reported $13.4BN valuation just 9 months later. Additionally, Will is on the board of Scale.ai. Timestamps: 0:00 Journey Into Startups 2:04 Why do many fintech companies work outside the regulatory system? 3:28 What are you running from and towards? 5:04 Do startups still build for the long term? 6:38 What does high performance mean to you? 8:02 Relationship to Ego 11:06 Relationship to Money 12:15 Changes in Leadership Style 13:37 Plaid vs Column 15:40 Lessons on Hiring 19:33 When is building slowly advantageous? 23:45 How did you structure your personal portfolio? 25:14 Are CEOs the best resource allocators? 25:50 How do you imbue patience with your team? 27:17 What does Column do? 35:45 US Financial System as a Protocol 40:20 What country has the best financial system? 42:02 How would you change the US financial system? 44:47 What happens to Coinbase next? 45:50 The Next Ten Years of Fintech 50:49 Apple is the Original Vertical Specialist 52:46 What books do you recommend? 53:18 Cold Emails Work 54:00 Biggest Strength and Weakness 54:48 Founding Company with Wife 58:28 What would you most like to change about venture? 59:33 The Next Five Years for William Hockey In Today’s Episode with Will Hockey We Discuss: 1.) The Founding of $13.4BN Plaid: How did Will make his way into the world of startups and come to found Plaid with Zach? If we are all a function of our histories, what is Will running from? What is he running toward? What does Will know now that he wishes he had known when he started Plaid? 2.) Will Hockey: The Makings of a Decacorn Founder: What does the term “high performance” mean to Will? How has this changed over time? Having had such a successful time building Plaid to $13.4BN, how does Will assess his own relationship to risk and his relationship to money? How does Will approach his own personal portfolio planning? Equity, debt, real-estate? How does Will optimize his own personal wealth? Column is his second time founding a company, what did Will decide to take from Plaid that worked well? What did he decide he would not do having seen it work badly at Plaid? 3.) The Building of Truly Great Teams: Why does Will believe that companies can be built so much slower than people think? How does Will determine the decisions that have to be made fast vs those with time? How does Will ensure the same size of urgency and speed within his team without this time or funding pressure? What have been Will’s single biggest lessons when it comes to people acquisition and retention? 4.) Fintech: The Next 10 Years: How will the next 10 years look different from the last in fintech? What changes will be better? What will be worse? What is Will worried about? What is he excited about? What does Will mean when he says, “the US financial system can function like a protocol”? What does Will believe are some of the core myths of the US financial system? Why does Will believe the current financial system can and will fix a lot of what crypto is trying to solve? What barriers will prevent this from happening? Items Mentioned in Today’s Episode: Will’s Favourite Book: The World for Sale: Money, Power and the Traders Who Barter the Earth’s Resources, Merchants of Grain: The Power and Profits of the Five Giant Companies at the Center of the World’s Food Supply Subscribe to the Podcast: https://www.thetwentyminutevc.com/william-hockey/ Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow Kyle Harrison on Twitter: https://twitter.com/williamhockey Follow 20VC on Instagram: https://www.instagram.com/20vc_reels Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok #WilliamHockey #fintech #ColumnBank #HarryStebbings #20VC