Ankur Nagpal: Selling Teachable For $250 Million & Revealing Secret Tax Strategies

The Dealroom with Shamus Madan

Ankur Nagpal shares his entrepreneurial journey, from making his first million through Facebook applications to founding Teachable. He discusses the evolution of Teachable, scaling its revenue, and navigating its acquisition. Ankur offers advice for college students on networking and for founders feeling stuck. Post-acquisition, he delves into his new ventures, Ocho and Carry, and running a venture fund. The episode explores key tax strategies for founders, including Peter Thiel's Roth IRA strategy, and balancing CEO responsibilities with personal values. Ankur reflects on the best advice received, the importance of family connections, and offers wisdom to his 18-year-old self.

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(0:00) Ankur Nagpal's journey to a million dollars through Facebook applications (0:32) Peter Thiel's tax strategy with founder shares in PayPal (2:46) Advice for college students and networking with industry leaders (5:29) Founding Teachable and its evolution (9:32) Building and scaling personal use products (10:11) Steps to scale Teachable's monthly recurring revenue and reverse engineering growth (16:37) Advice for founders feeling stuck and unique courses on Teachable (20:08) Teachable's acquisition offer and negotiation insights (25:13) Post-acquisition transition and new ventures (28:42) Investing and running a venture fund post-Teachable (30:02) Building new startups: Ocho and Carry (34:05) Key tax strategies for founders and real-life examples (37:53) Peter Thiel's Roth IRA strategy (39:45) Balancing CEO responsibilities and personal values (41:33) Best advice received and the importance of family connections (45:03) Advice to 18-year-old self and life reflections (46:10) Closing remarks and sponsor mention