Quit and join that risky tech startup? A guide to learning, earning & minimizing regret at startups

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Should you quit or job? What skills do you want to acquire? How do you evaluate how much you’ll actually earn? If you’re great at what you do, it turns out that the only kind of risk is not taking risk at all. This is my quick guide on how to think through different opportunities that come your way. Learning early on is more important, but earning is absolutely something you need to focus on mid-career.

I’m Garry Tan, venture capitalist and founder at Initialized Capital. We were earliest investors in billion dollar startups like Coinbase and Instacart. I’m doing my own one man YouTube channel with no staff or crew — I’m going for raw and unfiltered, not perfect.

Please like this video and subscribe to my channel if you want to see more videos like this!

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Date: September 9, 2020

34 thoughts on “Quit and join that risky tech startup? A guide to learning, earning & minimizing regret at startups

  1. Gary, thanks alot for making me realise I had been getting too secure under the comfort zone of job at MNC. Looking back at my life, realised that's not what I want to be. The commando inside me had been continuously demoting to reach the level of Police. Time to wake up, gear up and put commando to some action

  2. Super insightful video Gary 🙏🏼 how would you weigh each of the factors: interesting problems, learning and earning components into the decision (as in would you recommend overindexing on one over the other?). Also, for the equity calculations you showed, how would dilution impact the numbers/what’s a standard dilution % for future funding rounds when you’re say a series D/E startup which is already valued at $5B?

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