How to Make a Scary Decision

Growth often requires doing something a little dangerous. Here, six entrepreneurs share the calculus behind their biggest risks.

- Illustration by Tommy Parker

1/ Go with what you know.

After a year in business, we broke even without spending much on advertising. So I looked at the media landscape. The digital and paid social spaces were saturated by DTCS.TV and print would be hard to break through. But radio was a channel I'd had great experiences building brand equity on. So we went all in. I remortgaged my house five times, but by the end of our second year, we had grown 10 times. -SCOTT TANNEN, cofounder and CEO, Boll & Branch

2/ Trust your vision.

When I was 21, I raised capital to build a six-story mega hostel in Eastern Europe. Days before we broke ground, the Russian ruble crashed. Suddenly we had 30% of the $3 million budget in investor commitments and a 25-plus-year lease with my name on it. I was terrified. But I signed personal guarantees left and right, promising to pay everyone in future profits. It became one of the most profitable youth hostels in that part of the world.