495: The Science Behind Taking Risks (and Why They Definitely Pay Off)

2021-08-15

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It often seems like the most successful people are the ones who take the most risks. There’s no surprise that at one point, billionaire entrepreneurs were given the choice to either stay where they stood or leap for something greater. This is something that today’s guest, Sukhinder Singh Cassidy, understands. She’s helped lead some of the biggest companies around like J Crew, Stitch Fix, TripAdvisor, and Urban Outfitters (just to name a few).The one thing that Sukhinder has found throughout her years i...

It often seems like the most successful people are the ones who take the most risks. There’s no surprise that at one point, billionaire entrepreneurs were given the choice to either stay where they stood or leap for something greater. This is something that today’s guest, Sukhinder Singh Cassidy, understands. She’s helped lead some of the biggest companies around like J Crew, Stitch Fix, TripAdvisor, and Urban Outfitters (just to name a few).

The one thing that Sukhinder has found throughout her years in Silicon Valley and through writing her new book, Choose Possibility, is that groundbreaking leaders don’t just take one big risk, they take several small ones. This works for real estate investors too. If you’ve just gotten into real estate investing education, the first step for you isn’t to go out and buy a house, it’s to join a meetup, contact an agent, or even join the BiggerPockets forums. These are what Sukhinder calls the “minimum viable choice”. Don’t worry about doing everything, just do something!

Sukhinder gives some great advice on leadership for those in executive business roles, plus how to find talent in this increasingly competitive market. If you’re just starting in your career, take Sukhinder’s advice and do great work for great people, the rest will fall into place.

In This Episode We Cover:

How Sukhinder’s love of entrepreneurship began

“Coconut events” vs. “subway events” (and how you can plan for both)

Embracing uncertainty and calculating your risks

Starting in Silicon Valley and building a strong reputation

Choosing to make the “minimum viable choice” whenever possible

How to know whether you’re managing others or having others manage you

What leaders and business owners can do to attract the best talent

And So Much More!

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