Six Founders on the Scariest Business Decisions They Ever Made Growth often requires doing something a little dangerous. These entrepreneurs share the calculus behind their biggest risks.
By Entrepreneur Staff Edited by Frances Dodds
This story appears in the March 2022 issue of Entrepreneur. Subscribe »
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 megahostel 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." — Dan Mishin, founder and CEO, June Homes
Related: How to Harness the Power of Macro Decision-Making
3. Know what makes you needed.
"The scariest business decision I ever made was pivoting from my first startup, which grew 20 times in less than three months, to pursue FameBit. What gave me courage was that FameBit was born of a real problem I experienced at my first startup. I was confident that others were experiencing this problem, too. Having a unique insight that others aren't seeing feels like a superpower. FameBit was acquired by Google in 2016 and became YouTube's branded content arm." — Agnes Kozera, cofounder, Podcorn
4. Break big moves into smaller steps.
"When I started at one of the nation's largest pizza brands, we received capital to build an e-commerce platform for all of the United Kingdom franchisees. Getting it right was critical to building credibility and trust. I found courage by reminding myself to start small with a system that learns quickly. The only way to make big scary decisions is by breaking the problem down into small and testable hypotheses. Mistakes are inevitable. The key is being able to reverse and fix them." — Helen Vaid, CEO, Foundry
5. Ask what benefits your customer.
"We spent more than a year developing our AC unit. When it was finally ready for user testing, it wasn't as easy to install as we had hoped. We faced a conundrum: Do we redo the design and risk our launch date? Or do we push forward with something less than ideal? We realized we cared too much about customer experience. The redesign was risky, scary, and anxiety-inducing, but over a year after the launch, Wirecutter called our AC the "easiest we've ever installed.'" — Mike Mayer, cofounder and CEO, Windmill
Related: 6 Founders on When to Accept 'No,' and When to Persevere
6. Focus on your purpose.
"One of the scariest decisions we ever made was suing the Metropolitan Transportation Authority [for stopping us from advertising on public transit]. Our purpose is to help people integrate sexual pleasure into their well-being, and to grow, we needed to put that message out there. When we realized suing the MTA could engage the conversation in a really cool, kind of legal, systematic way — which completely aligned with Dame's purpose — I knew it was the right decision." — Alexandra Fine, founder and CEO, Dame
