If you need to do something hard start by committing to it for just 30 minutes. You can do almost anything for 30 minutes no matter how difficult it is. This is the advice that Natalie Gray got from her college professor, pushing her to finish a 3 year graduate degree in just 1 year. She later applied that advice to teaching herself how to be a designer, marketer, sales expert, and product leader. She’s now the Co-founder and Head of Product at Cover, a startup that recently raised $27 million to change the way people get insurance.
While Cover has grown very rapidly in its first four years – getting accepted into YCombinator on a prototype, getting rapid early customer traction, attracting investors, and tripling in size to 124 employees in just the last year – Natalie’s story to getting to this point was anything but a straight line.
In this episode we talk about the various career shifts that led her to teaming up with her current co-founders on a completely different business and how working on that business for two years, and then together at Shopify after being acquired, ultimately lead them to recognize a massive opportunity in insurance while on a weekend hack session at a cabin with the team.